Rudy Manning

Agencies play a critical role in ensuring that the next generation of creatives reflects the world we live in, and Rudy Manning takes that responsibility very seriously. As the co-founder and chief creative officer of Pastilla Inc., he is dedicated to not only providing services for a diverse range of clients, but also for making opportunities to get more people of color working in the design.

Rudy starts off talking more about Pastilla, and showing the ins and outs of what it takes to operate an agency. He also spoke about growing up in Panama and Germany before coming to the U.S., shared some stories of his early days designing DVD magazines, and how the combination of these experiences brought him to founding his own creative agency. Rudy also talked about teaching the next generation of designers at ArtCenter, being board president at Art Division, and gave some great advice for anyone looking to start their own agency one day. Rudy’s passion for all things design and his drive to help uplift others truly makes him a design leader worth following!

Interview Transcript

Maurice Cherry:
All right, so tell us who you are and what you do.

Rudy Manning:
My name is Rudy Manning and I am a creative director. My title is the Chief Creative Officer for an agency that I started about 18 years ago or 19 years ago now, called Pastilla based out of Pasadena or Los Angeles, California.

Maurice Cherry:
Wow, that’s pretty good. So you’re coming up on 20 years of that.

Rudy Manning:
Yeah, yeah, I know. We’re getting excited. We put a big event together for everybody who’s been a part of this journey. So yeah, it’s a big milestone.

Maurice Cherry:
Yeah. It feels like the milestones sneak up on you. You’re so busy sometimes in the work and doing it that you look up and you’re like, “Wait a minute, I’ve been doing this for 20 years?”

Rudy Manning:
Yeah, I’m telling you, it goes by… When you’re in it, sometimes it feels like it’s treading along, but then you look back and you’re like, wow, awesome. Yeah. Super grateful to still be in business and have it continue to thrive. So super excited.

Maurice Cherry:
How has 2023 been going so far?

Rudy Manning:
Really, really good. There was a lot of things shifted in the agency about five years ago. I merged with another agency that was one of our partners. They were doing a lot of development for us and probably for most of the time at the agency, up to that point, they were the main development partner for anything we did that was digital base. We decided after a long relationship to just come together, it just made sense. And that really shifted the trajectory of the agency the past five years. We’ve matured, we’ve grown substantially in that time. Really, really just have a little bit more of a focus.

2023 is, I think, really excited because, although a lot of things in the economy are uncertain, I feel like we’ve done some pretty smart things that have kept us afloat and kept us strong. Definitely the kind of work that we do in those years of the pandemic really ended up helping out for us because we’re a creative branding agency, really branding led, but we do a lot of digital products. So obviously there was a lot of investment in things digital. So that really helped out and now we’re positioned for a very steady growth of 2023. So, so far so good.

Maurice Cherry:
Now, were there any big goals that you wanted to accomplish this year?

Rudy Manning:
Well, last year one of the big goals we had was growth. I’m going to go a little bit into agency talk. This might go a little bit deep, but I think if somebody’s out there listening and has an agency, I think this is really important. Every year is different. Sometimes it’s like revenue, sometimes it’s profit, sometimes it might be people. There’s the goal, growing. And last year it was a lot about refining the team, making sure that the people who we had were working well together. Not only just processes, but the personalities and the right roles and the right balance of folks that really can help continue to lead and build the company and service our clients.

So that was a really huge goal and we owe huge testament to a lot of people in our agency, but definitely our HR team and we really refined a team. At the end we started off the year now knowing that the staff that we have is solid, they’re working together, a really well oiled machine and I feel like we’ve achieved that last year and this year now it’s becoming about really working. I’m calling the title for this year, nurture the details, which is about going a little deeper into the relationships that we have with our clients and not just servicing them, but really understanding their needs from a full 360 to be able to deliver as much value as we can. Not necessarily growth from growing clients, but growing the clients that we have currently.

So that’s really what I’m focused on for this year, and so far so good. We’ve already in the first two months have been able to do that pretty well. So I’m looking to continue to foster that in the team. And from the creative, the same thing. Being able to push the creative further and further, be able to deliver the best at every single thing that the client sees and making sure that they continue to stay with us, continue to come back and continue to see us as a strong partner to be able to service them in other things that maybe they didn’t even think we can help them with.

Maurice Cherry:
Well, let’s jump more into talking about Pastilla. You’re the co-founder and chief creative officer. You’ve already given a little bit of background about the team and the services and stuff. What really sets Pastilla apart from other agencies?

Rudy Manning:
It’s funny, when I was in school, in design school, I graduated and a lot of people during that time were like, “Oh, I’m going to jump into web. I’m going to work in motion. I’m going to work in print.” But really at that time, you had to know a little bit of everything, but I really liked having to cross-discipline position and I was working everything from packaging to environmental to doing film titles, commercials, apps, even back in 2003, 2004. I’ve always been in this cross sector of creative where it didn’t matter what discipline it was.

Now, that’s been really fun. A really, really exciting 20 years. I’ve learned a lot. It wasn’t easy because you do have to, to continue to sell, there is a certain pattern and you want agencies or you want clients to have that one thing that they think about you. And when you’re working and building the agency, it’s really tough to figure that out because you’re just taking things as it comes. And especially if I’m the kind of person that’s excited about a lot of different things, it’s been tough. It was really tough, I would say the first 12, 13 years. We were doing motion one year and the next year we’re doing the launch campaign for Microsoft Surface Tablet in 2012 or ’13. So very, very different projects, but exciting nonetheless. But made it difficult because when you tell the story of who your agency is, you really want to have the repeat factor. Even if it’s a different story and positioning, you do want to have this focus. So that was tough.

Around that time, 2013, I decided what we really do well and what I really like to do the most out of everything we did was branding and really looking at every client that came to us from a branding perspective, whether it was a brand new client where it’s a brand new company where you’re doing strategy, naming, identity system, and then executing that, which makes sense because we had that full service. That was something that finally, I would say at that time, we were able to start really honing down who we are as a branding agency. But at the same time, what made it interesting is we also had a deep understanding of how to put that company or that brand in action. So how it applies in digital, how it applies in motion, how it applies in print, and being able to do the full picture after we do the identity system.

It took a long time to do that and to get to that point, but I feel like that was one huge defining point at refining who we are, that made us stand out, at least let’s say in 2013 to 2016 or so. Then, I would say around that time, 2016, I started feeling like I wanted to do work that mattered a little bit more. Not that any of the work that we did didn’t matter, but something was in me that felt like I want to be able to be a part of the communication and deliver creative to projects and initiatives that had some kind of social impact through some different situations.

I ended up learning a little bit about the government work and how to approach it. It took a very long time, but I really got interested in being able to service the same kind of level of high end creative, the same kind of level of thinking and focus that we give to the private sector clients, but give it to more civic, public or nonprofit clients. And I would say it was specifically public sector. So we won one project, for the city of Pasadena we did a anti-tobacco campaign. That went really, really well and that’s when I got the bug of like, “Wow, I really like this idea of designing for the people directly, designing for communities.”

And now looking at eight years later or so, just last year rebranded… Well, this year, we actually just finished rebranding a city, the identity, the strategy and we’re going to continue to serve them. It was a really amazing experience to be able to put all that we’ve learned this first 18 years into branding a city. One of the reasons they picked us was because we weren’t a typical public sector type of agency. They said it right in the first town hall that they had. They chose us because we were not the typical public agency that spoke government and so forth. They felt like we were a little bit more on the ground and had a fresh perspective. We commend them for that as well because I know that often we lose because there’s other agencies that know how to speak that.

So I would say we have this well-rounded full service agency that’s branding focused, most of our clients come through us for that. And that we’re civic minded, civic social impact minded. We do things in sustainability and so forth. And sometimes some private sector clients come to us because of that. We also have that passion for doing work that matters and that directly affects people and communities.

Maurice Cherry:
I would have to imagine that city branding project was a lot of fun. When you think about the scope of what that entails, it’s not just, “Oh, we’re going to make a logo and a style guide.” There’s so much that has to go into that level of branding because a city is more than just a company, it’s more than just a brand. It’s not a society but I say that to say that the scope of something like that is immense.

Rudy Manning:
Yeah, absolutely. We underestimated some parts of it. The discovery and the research that we had to do, especially because we’re not based in the city. It was the city of Corona and we’re maybe about an hour away from them. One of the comments in the beginning when they first introduced us to the city council was like, “Oh, why didn’t you guys go with a company that was in the city of Corona, or from the city?” We had to invest a lot of time into proving that an outsider, an agency that comes can have a fresh perspective, can do just as good if not a better job than somebody who’s really close to the city.

So the discovery and the strategy was a lot of work, a lot of workshops, a lot of meetings, a lot of popups that we had to do to get engagement and really validate the messaging and the final outcome of the identity.

Maurice Cherry:
It’s tough to get right, because so many people that are in a city, it’s not just business, it’s not just commerce, it’s everyday citizens. It’s so so hard to get right. I guess the reason I’m speaking about this so passionately is because I’m in Atlanta and we were known for a spectacularly bad city branding campaign back in the early to mid 2000s. I happened to be working in the city, working in tourism. So I got to see it unfold from the inside about how bad it was. But yeah, we were known for a spectacularly bad branding campaign called Brand Atlanta. I was working in the city in tourism at the time, and just seeing it unfold from the inside was horrible because you could tell that the people that were putting this together, and I think they got a local agency to do it, but what can happen, and I think you probably know this too, is that the client can get so held up in what their vision of it should be, that it’s hard for the agency to do the necessary research and work that needs to happen in order to really provide good work.

And so basically we just had all these suits that were in our tourism board. There were like, “Atlanta is this,” and as someone who… I’m not from Atlanta, but I’ve lived in Atlanta, I’m from the South. I was like, “Atlanta is so much more than these things that you think it is.” They thought Atlanta was the zoo and the baseball team and all the very family friendly, squeaky clean sort of stuff. But I’m like, “Atlanta is also hip hop and strip clubs, it’s all of that. And you’re trying to sanitize this vision of what the city is, because at the time they were trying to get more conferences to come to the city, which was the main point of them doing the rebrand is to make the city seem more appealing.

They did it. They rolled it out. We had, I think it happened at a Falcons game where they did the whole Brand Atlanta rollout. They had the symphony and they wrote this song. They had this song that was written with T.I. and Usher and it was all horrible. People hated it. It was so bad. It was so bad. There are very little, if any traces of it still around in the city because they quickly covered it up after it went out. So city branding is tough. It’s so tough to get right.

Rudy Manning:
That would be our worst nightmare. And actually, there’s one project that we had pitched a couple years ago. I can’t name the university, but we came in very close to winning it. We ended up losing it to another company who had a lot of experience in higher ed. One of the main things I pitched that got us very close is I said, “This is not a logo identity we’re doing. We’re really doing a political campaign in a sense. We have to approach everything we do to get people, the students, the instructors, to believe in the direction before we even go in that direction. So we have to really understand what it is that the students and the faculty need and what do they believe to then be able to communicate an identity system.”

But what happened is at some point it seemed like they jumped the gun. We didn’t get it. Three years later, they end up reaching back to us saying, “This was a horrible experience what happened to us, everybody hated the logo. There was political nightmare, PR nightmare, communication nightmare in the school.” And obviously it was too late at that point, but they’re like, “Definitely we should have gone by you.” There’s literally an email saying, “We regret going with this other agency. We should have gone by you because the direction that you were pitching was exactly what we needed.”

One of the ideas was the students at the school, the graphic design students, they need to be a part of this identity for the school. They need to have their hands in it in some kind of way. All of that just really gets people to feel that this came from within. It has to feel like that with anything like that. If not, it’s really, really hard. So I don’t know. It’s crazy.

Maurice Cherry:
Yeah.

Rudy Manning:
[inaudible 00:18:34]

Maurice Cherry:
When new projects come in with you sitting at the head of the company, do you get to work hands-on with them?

Rudy Manning:
I do. We’re about 35 or so people with some contractors definitely goes up to maybe even close to 50. The design team, we’re pretty nimble. So I’m the creative director. We have an art director and we have a few graphic designers and UX designers and so forth. But I still am, as the acting creative director, at least maybe for the next couple years, I am potentially looking to bring in a creative director.

So that means that basically I don’t design, but I review. I give critiques. I give from either my art director or my lead designers, senior designers. They will go and do the work themselves and then come back, present to me. I give them feedback, I give my thoughts. They present to me, I give them feedback on how to present, what kinds of things to say. And every now and then I’ll have to present. But seldom, less and less. I think my team’s gotten to the point where they’re pretty good at understanding my vision and so forth.

Sometimes in the beginning I set some parameters, I would say, around the direction of where we should go based off the strategy or whatever it may be. But often they’ll come to me with some ideas and then I’ll take those ideas and give them some feedback on refining them, even if it’s just general higher level concepts.

Maurice Cherry:
So you’re not, like you said, working hands on but you’re still pretty close to the project in that you get to see it unfold, kind of step by step.

Rudy Manning:
Yeah, exactly. Exactly. I do a lot of other things. My partner now rents most of the operations, but I’m still really responsible for a lot of the business development, the relationship of our clients and overseeing all the accounts, not just from the creative, but managing the entire perspective of the direction of that client.

Maurice Cherry:
What does a regular day look like for you?

Rudy Manning:
Lot of calls. I think these days, we’ve had an office for probably the first 15 years of our company and just after we merged with Kremsa, is the name of the company that we merged with. Just after that, we decided, you know what? Let’s go remote for a little bit. We were trying to figure out how the two companies were going to come together. We did that for about a year, year and a half. We started looking for an office. Then the pandemic hit. So it was frustrating for me working remote, but I literally learned to adapt. We all have adapted pretty well for it. Sometimes we obviously meet, and I say that because one of the drawbacks now is on a lot of meetings because we have to force those kind of interactions between people. So that means my days are pretty booked up with calls.

I would probably say I spend about at least five to six hours a day on calls. I would say half of it is internal things, whether it be operational meetings or looking at something we’re doing internally to market ourselves or project stuff, account managers presenting to me where we’re at with the client, the margins, what new projects are coming along and so forth. So I do that and then probably 10, 20% of the day might be some creative meeting that I have with the team where they’re presenting some ideas or so forth. But most of it’s operational business meetings. Yeah, I would say that’s basically my whole entire day.

Maurice Cherry:
Yeah. Business development’s important though, because you got to bring them in, you got to bring the client work in.

Rudy Manning:
Yeah, absolutely. It’s always been something I’ve done forever, just naturally, it’s been something that I’ve always just somehow understood. So it’s the thing that probably, from a financial point of view, that’s the biggest value right now that I bring to the company is the business development. Most of the projects come through something of my relationship or some doing of our content or so forth. Yeah.

Maurice Cherry:
Is it tough balancing the creative and the business sides of running an agency?

Rudy Manning:
It is, and it’s getting harder and harder because I talk about how we’re now remote and how many hours I’m on calls, because so much of it is that higher level strategic thinking of the business, the client, operations, who do we need to hire? What’s happening with this hire? Do we need to bring in another person for this? Hey, there’s an issue with this client, this is what we need to do, or here’s some cool things that we can do or new projects, pitches, proposals. All of that really takes up most of my time.

So staying creative is really, really important for me. I try to do that as much as I can. I sort of time box it. So one of the things, we just moved into a new house a year and a half ago, two years ago. So I’ve had a lot of fun just doing interior design and designing the space and just remodeling the house and not just hands on, but the actual design part of it. So I’ve had a lot of fun doing that and bringing my design into that. It’s been something I’ve been enjoying. At least right now, that’s definitely a way I’m getting my creative output. Also teaching is really great as well. Hearing students work and giving feedback at that level as well, that also feeds me tremendously.

Maurice Cherry:
Yeah. I want to talk more about your teaching later, but before we get to that, I want to learn more about you. I want to learn about how you got to where you are now, where you’re running an agency and you’ve got it staffed with all these designers and things like that. So tell me about where you grew up. Are you originally from California?

Rudy Manning:
No, actually I’m Panameno. I was born in Panama. Yeah, I came here. We immigrated with my parents here when I was seven or eight years old. We came here. My dad joined the Army. He thought this is probably the best way for us to make a living for him and provide for us. Immediately after that, I would say about a year after we moved here, he got shipped to Germany. So I was basically, that’s where I learned English was in Germany.

Maurice Cherry:
Interesting.

Rudy Manning:
I only spoke Spanish, so I was there for about almost four years, I think. Then we came back to United States when I was 11. We were basically in Los Angeles, and then we moved to Rialto. So basically from 11, 12 up, I’ve been in Southern California area. I went to high school in Redlands. After my mom and dad divorced, my mom moved towards that area and that’s where actually I ended up meeting somebody who gave me a little bit of a hint about me wanting to maybe study graphic design at the high school. So I went to Redlands High School and then from there I graduated, went to Cal Poly Pomona for a couple years, and then ended up transferring to ArtCenter, which is what brought me to Pasadena.

Maurice Cherry:
Now, back before you went to Cal Poly Pomona and everything, as you were traveling between these different countries as a kid and then eventually settling in California, did you always have an interest in design and creativity and stuff like that?

Rudy Manning:
I think it was mainly just drawing. I loved to draw since I was a little kid. My brother as well. We both used to just draw together, and he’s a graphic designer too. My dad studied architecture for a little bit in Panama, but he’s always drawn and painted his whole life. We have a pretty artistic family. So my dad, since we were little, always was drawing and we’d copy his drawings and he’d go one by one and then we’d follow what he was doing. We’d do that all the time, in front of the TV. We’d sit down and he’d be talking, he’d be showing us what to do. Did that for many years and my mom, a little bit after, my mom and dad divorced, my mom started a business. So then got to see that part of it. She’s been really successful at it.

So got to see the benefits of owning your own company and your own business and what kind of freedom that gives you, and the satisfaction and seeing her in it, that drove that part of it as well. So I think those two things combined is what got me the framework of thinking of building an agency.

I would say, I remember I stopped drawing at 11 or 12 years old. I don’t know why.I think I just ended up playing baseball. My focus was different and I was just playing baseball all the time. And then one day, I don’t know why, I just remember, I was 14 and I was just like, “You know what? Let me draw a baseball player.” That’s what I loved. And I remember I drew Orel Hershiser. I had it in my art class and I took it to school. I remember that feeling of everybody like, “Oh my gosh, you drew this? How did you…” That reaction, you kind of had a similar background as an artist, you’re like, man, there’s this feedback that you get that’s a little bit of this high. I’ll never forget that. So I just kept on drawing and then that went to painting, and then I was just taking art and painting classes. And eventually that took over my passion for baseball, and that’s all I wanted to do, was draw on paint sports figures.

I wanted to be like Leroy Neiman, who’s a very famous sports fine artist painter. And then until I was in one of my art classes, I think I was a junior or something, it was a student in there who was a really good artist who was going to graduate. And I asked him, “Hey, what are you going to do after school?” And he’s like, “Oh, I’m going to go to PCC, Pasadena City College, and then I’m going to transfer to ArtCenter and study graphic design.” I’m like, “Oh, what’s that?” And he’s like, “It’s like doing things for MTV.” And I remember going, “Dang.” That was the days of MTV, MTV, the real MTV. And I was like, “That is amazing. Graphics for MTV.” I didn’t even know the word graphics actually. I just thought art for TV that people could see. So I remember that, and that always stuck with me.

So when I graduated, I was just looking for a school that had graphic design, which wasn’t that many. And Cal Poly ended up being one of those schools. So that’s where I dove into graphic design for the first time there.

Maurice Cherry:
How was your time at Cal Poly Pomona?

Rudy Manning:
It was interesting because I think in high school I was pretty kept in. I didn’t do a lot of stuff. I feel like when I got to Cal Poly, I was in the dorms and I just got this freedom of like, “Oh my gosh, I’m on myself.” So I went down that, it was a lot of fun, but it was like I probably didn’t know what to do with all of that energy. So one thing is I would say my focus wasn’t there as it should be those first couple years. I want to say, despite that, I struggled a bit with graphic design there. For whatever reason, I didn’t make the connection.

There was a lettering class I remember. The lettering class that we had, it was all about craftsmanship. You had to draw, let’s say the letter E with Prisma color, and it was like a five-inch height type and you have to draw it so it literally looks like it’s printed. It was very difficult that class for me, not because I couldn’t do it, I could do it, but I didn’t have the patience. I wanted to design. I wanted to draw. I remember the instructor saying, “If you get a C or under in this class, I highly suggest you don’t continue in graphic design, ’cause graphic design is really tough.” And I remember as, not to say fine artist, tough as well, but in terms of, I think what he was saying is, “You really have to love this to really continue in this direction.” It was one of the first classes in graphic design you were suppose to take.

So towards the whole class, I was just like, I’m struggling. I think I’m going to get a C. The final project was you get to draw something and use letter form and typography and visuals together. So I got to do this book cover. I remember I did a Malcolm X book cover and you put it up to class, the final, and everybody was just looking at this project, looking at my project, and the teacher was like, “Who did this?” It was the first time out of the whole entire term that I felt any kind of positivity in that class. All the time, it was just like… I remember going, “What’s happening?” And so I walked out of class and the instructor, said, “Hey, I know I said you shouldn’t be in graphic design, or if you get a C or lower, I think you’re going to get a C.” I’m like, “Yeah, I know.” And he’s like, “Well, I think you should stay in graphic design though.” So I was like, “Oh, huh, okay.” I walked away, still struggled, still was a tough time in the other classes.

Somebody had told me, “Hey, you got to take a class at ArtCenter. You’d be really good at it.” I’m like, “I don’t know what you see, because I’m struggling in every graphic design.” I did great in the painting classes. Those are the ones I really loved. So I took a night class. She ended up just convincing me, and I was nervous because I thought, man, back then I thought ArtCenter’s this sort of mecca. I took a night class, like an extension class while I was still at Cal Poly.

The first day you go and you present your ideas for a logo. I was just drawing and sketching and concepting stuff, put it up. I knew the moment the teacher started talking, the first, not even to my project, another student, I thought this, I’m in love. I literally felt like this is what I want to do for the rest of my life. And I just never took another class at Cal Poly. Again, Cal Poly, this was early on in Cal Poly for their graphic design. So they really were working things and some amazing designers came out of this. So that was just me at that time. But I just fell in love with graphic design at ArtCenter. I eventually finished my foundation at Cal Poly. Then I got a full scholarship actually after a couple classes I took at ArtCenter. I built my portfolio, some from Cal Poly, some from the ArtCenter, and I got a full scholarship, a James Irvine scholarship.

That was it. Kind of changed my life. The only hiccup during that time is a girl that I had been dating ended up getting pregnant. So I ended up having a child pretty early on. So I was starting ArtCenter while learning to be a father at the same time. So that’s another story.

Maurice Cherry:
Wow.

Rudy Manning:
Definitely all came all at once, but definitely matured me and I think eventually was all for the good, of course.

Maurice Cherry:
Well, I’ve heard from a lot of folks on this show that sometimes when they go into school having a lot of this artistic ability and love, sometimes the school can almost effectively snuff it out of them through the professors or the courses or anything like that. So it’s good that you still had that spark and decided to continue it by going somewhere else that was probably more focused in the direction that you needed to go, which of course now, based on where you’re at right now, that was a good direction to take.

Rudy Manning:
Yeah, yeah, absolutely. Absolutely. It’s crazy. You never know. Those little moments. I remember thinking like, “Oh gosh, the classes are at night and this and that.” But yeah, I loved those classes. I wanted to spend all my time in the ArtCenter at night classes then. So, yeah.

Maurice Cherry:
Now you’ve graduated, you’re out there as a working designer. What was your early career before you started Pastilla?

Rudy Manning:
As I mentioned during school, I definitely like to get my hands in everything that was design. I think it’s one of the reasons I mentioned earlier, I like even just interior design. I have a passion for anything that is where you’re taking these elements of your artistic being and putting into some physical space or visual space or designing a city. So I definitely can see how all those things combining works together. And I did the same thing at school. And so when I graduated, I wanted to work somewhere that didn’t want to push me into one direction. I didn’t want to work in an agency that only had me do print, only doing web, or only doing motion. So the best place was a company then called… I had a couple different companies, but I think towards the end it was called Quick Band Networks or DVD Mags, which was you basically are designing a DVD magazine is what they call it.

So every month you would get a subscription of a DVD. One of them was short films. You get one DVD of short films, another one was music. So you get to have these music videos and all this content on these DVDs. I got to design basically the editorial, but the interactive part. So I got to do the identity of each of the magazines. I got to do the interactive part of the DVD. I got to do the animation of the DVD. I got to do the ads. So that to me was perfect. I got to get my hands in all of that. That’s really where I started for the first couple of years. I started freelancing a little bit after that. And that took me to Nokia for about four years. I worked there really as a freelancer.

I had a feeling at that time that at some point I’m going to start my own company just because I really enjoyed working with my own clients. So in between that, I took freelance projects at night and weekends, and I really enjoyed having full control of like, I’m presenting to the client, I’m giving them my vision, and I’m able to directly connect with them to be able to persuade them of the concept that I think is right. Rather than, here’s a bunch of ideas, now you have somebody else pitching it for you. So I really love that. So I thought, I’m going to start my own studio. But I needed to build up enough momentum as a freelancer.

So I really freelanced for about six years. Then when I was at Nokia, I said it was a time of my life, I got divorced in my late 20s and I thought might be a good time for me to do this now for a lot of different reasons. So I told Nokia, “I’m going to start my own company. If you guys would like to hire more of me, I’d be happy to take the work and continue as my own company.” And so Nokia was my first client. So I’m super thankful for that. For the first couple years, a lot of the work we did was Nokia. And so that was the first momentum of Pastilla, which was then called Pastilla Studio.

Maurice Cherry:
That’s amazing. You must have made some really great relationships at Nokia in order for them to entrust you with that. Say, I’m going to go out on my own. And they’re like, “Okay, great. We’ll still toss some work your way.”

Rudy Manning:
Yeah, definitely. I worked really hard for them, was really great people, a lot of them, some of them I knew from ArtCenter. I got to meet people from all over the world there and really was a time where technology was in a bit of transition. Imagine that was like 2000, a couple years before that. The iPhone definitely hadn’t come out. But before that, Google had just come out a couple years before that. It’s really early on. So I think I came with that diverse background of motion, interactive and print, and being able to cross-discipline. I think that really, the design director, Gerardo, liked that so I was able to really use my diverse background and experiences to Nokia and help the team out for those four years. So yeah, we did some great work.

Maurice Cherry:
Honestly, coming with those skills at a time when as soon as you said DVD magazines, I was like, oh, I already know when this happened. This is turn of the century or turn the millennium, whatever, like ’99, 2000. I remember those DVD magazines vividly. But yeah, coming with all those skills at a time when technology and design and the web were growing at this rapid pace, the stuff that you were doing didn’t really even exist 10 years ago. The advent of the personal computer and the internet becoming something that was no longer bound to DVDs or CDs that you get in the mail. The fact that things were growing at this rapid pace and you’re coming in with all these skills, especially at a time when companies are trying to decide, “How do I become a part of this new thing? How do I have a website? How do I take orders online or do all this stuff?” And you show up to the scene well-equipped like, “Hey, I’ve got the skills if you got the work.” Sounds good.

Rudy Manning:
Yep, exactly. Exactly, exactly. It was a really fun time.

Maurice Cherry:
And now while you were building Pastilla, it sounds like there were other ventures that you were doing as well, right? You did some work with an app, you founded a film company, I guess. Tell me about those other ventures.

Rudy Manning:
Obviously from let’s say 2004, those first 10 years were extremely busy for me. Continues to be anytime you’re a business owner. But those first 10 years I was basically raising my kids. I have a boy and a girl from my first marriage. And so I was raising the kids while starting this company essentially. We have 50-50 custody. So they got to share that experience. So those first 10 years was extremely busy. I would say around 2014 maybe, 2013, a friend came to me about an idea that he had for a startup, and he wanted me to look at it and see if I was interested in being his partner. He presented to me, did this whole pitch. And basically what it was is, to be honest, it’s not that different than what Instagram Reels is, what TikTok is now. The only company that was doing something sort of similar was musically that ended up becoming TikTok back then.

But even then it was very different, the UX. So basically at the end, what it was is you select video clips from your phone and it strings a video edited to music together. The thing that it did a little different was it took the music patterns and did the edit based on the pattern of the music, the rhythm, the beats per minute. There were 5 second ones, 15, 20, 30 I think it was. And so we built the app, we started it, we got some funding.

I learned a lot. Number one, I was able to use all of the tools and experience that I have learned, not just from owning an agency, but also working with clients as well. So it was really great. But it was tough. It was tough because it was at a time where we saw Instagram really starting to, I hate to say it, but just copy what everybody else was doing, so see what’s happening. And so like, “Oh, I like discovery. I like how Snapchat’s doing. Okay. Yeah. All right, let’s do this.” And then they bought the music catalog of Universal then.

And that’s where, okay, this is going to be really tough to… Even though the technology was different and interesting, it was not going to be able to compete because it had to be a platform. So it was more like a tool and a feature. So after I would say couple years, we got some awards and things out of it and definitely some really good recognition. But we decided to close that. Around that time, I got married in 2014, so we’ve been married about nine years. And my wife is actually a filmmaker. She has always wanted to be a director. And during that time, she was building her career. So she started making brand films. She’s an amazing storyteller. It was perfect because obviously I had done motion, I had been part of doing BFX for films and so forth.

So we started… It’s her thing. This is what she runs to this day now. It’s been maybe five years, but we took some of the experience that I had in motion and put it into what now it’s actually called Fe Films, Fe Brand Films or Fe Films. So she does brand films, she does motion graphics work, but really the thrust is she’s looking to have it be a full-fledged feature film company. So she’s doing some short films and some narrative work on that. She’s got a couple scripts that have been optioned and she’s been working with. So that’s, when you saw Fe Brand Films, that’s what it is. All of the motion parts that were Pastilla or most of it got diverted into Fe Films now.

Maurice Cherry:
And now also you’re board president of Art Division. Can you tell me a bit about that?

Rudy Manning:
Yeah. About two, three years ago, let me back up a little bit from that because, say about 10 years ago I had this thought and I had mentioned to my wife, “Wow, our studios are empty on Saturdays and Sundays. Wouldn’t be amazing to go out and bus students from the different areas in Los Angeles and different groups and be able to teach kids graphic design?” I’ve always had a passion for kids. And at that point I had just started teaching as well. So I thought, yeah, this could be really interesting to do. And so I had it in the back of my head, but with everything else, this was really busy and I never really was able to put the gas on that.

And then about two, three years ago, somebody recommended me, introduced me to Art Division, which was a school in Rampart District of Los Angeles that was teaching fine arts, visual arts to kids specifically in that area, primarily of Latino immigrants. Me speaking Spanish, being Latino, I felt like, I wanted to get to know a little bit more about the school. So went in, heard a little bit about it. Definitely saw some potential for me from my background coming from teaching at ArtCenter. Also, some of the things I have been thinking about in the past and learning from what they’re doing, seeing if that could be something I can learn from and be a part of something that was really giving kids who have graduated high school, have amazing art talent, be able to give them the ability for another chance to develop a career in arts. And then me maybe be a part of introducing design to their curriculum.

So after six months of being on the board, I was selected as the board president. And for the past year and a half, that’s been my role. What I’ve been doing is slowly trying to find ways to include graphic design into the curriculum. And we hope, hopefully by this fall, we have at least a couple classes that we start to teach. We’re developing that right now. We’ve done some graphic design workshops where kids have come in to hear a little bit about who I am. I’m also looking to introduce some of the designers from Pastilla also potentially to even go there and do some teaching and so forth and be able to give back to these kids. Because some of them, they’re artists, they have a passion for art and design, but who knows? That art background could end up becoming a design passion and graphic design passion and can end up having a career. It’s really tough and really expensive to go to school these days, especially art school. So giving them some of these opportunities I think could be really interesting. So I’m looking forward to how this develops.

Maurice Cherry:
Now along with this community work, which by the way sounds amazing. I would love to have been a part of a program like that when I was a kid. But you’re also an instructor at ArtCenter College of Design where you went to college. You’ve taught there now for almost nine years. Tell me a bit about what you teach.

Rudy Manning:
Yeah. I started teaching in the product design department, which is industrial design, we call industrial design, product design at ArtCenter. I was brought in to teach graphic design to the product design students essentially. And then that turned into me teaching the students, there was a class that helped the product design students or industrial design students how to brand themselves as they get ready to graduate, how do they position who they are and so forth. Those first classes, I would say that first year, year and a half, which for me to just get my feet wet and see do I like teaching period, how can I fit into my schedule? Does it work for me? And what are we getting out of it myself personally? And also am I being able to deliver and be good at it?

I loved it. I really, really liked doing it. I got as much out of the students as they get as much out of me. It’s definitely a very symbiotic relationship and I think that really helps my perspective in how I teach. And so I taught in that department and immediately obviously, I wanted to teach in the graphic design department. I was a natural inkling. It’s kind of tough to jump into teaching, especially ArtCenter because you have some of the top designers in the world and artists in the world teaching there and everybody wants to teach there. So I ended up getting asked to teach a branding class. They knew the work and stuff that I did. So I started teaching what now, the bulk of those years, up until maybe last year, I was teaching what was called Transmedia, which is basically a branding class that looks at what I mentioned, the cross sector of how branding and identity systems get implemented into and go into action when it comes to digital, motion, space, environmental.

So that was my class and I absolutely loved teaching, it was called Communication Design Five, Branding for Trans Media, I think. I did that for about six, seven years. I took a pause on that class. I was teaching two classes a week while I was still running the agency, still with this transition of the two new companies. Well, last summer I took a pause for two terms because teaching remotely and being remote as an agency was taking a toll on me. The classes at ArtCenter are about five hours. So if I was teaching two classes, that’s two days that I’m on class for five hours on screen. And then as I mentioned, my work is screen time stuff. So I ended up feeling after six, seven years, I don’t know if I have enough bandwidth.

Things started opening up obviously in the fall, but I started now with Art Division and my focus on there, I’m started to rethink a little bit of my long-term strategy in teaching and am I going to continue teaching at ArtCenter? So currently, I’m still teaching now. I’m back to teaching in the masters program, a branding futures class, which is I’m teaching with another instructor about strategies of future casting, how brands could future cast either their audience, either the business models, any kind of future strategic thinking of a brand. So I’m teaching that class now and I’m going to be teaching one more during the summer. But I think that after that I’ll be taking a pause for a while to do some art work and thinking with Art Division and put my time into that.

Maurice Cherry:
Look, you got to fill up your own cup first. It sounds like with everything you’re doing with Pastilla of course, and then also with teaching, you can get depleted very quickly.

Rudy Manning:
Yeah, definitely. Definitely. It all kind of works together in a way. So it is definitely a lot to juggle, but it all works for the greater good, really, ultimately also of Pastilla because when I do things for Art Division, not only am I helping feed ourselves, but we also tell that story of how we’re involved in Art Division when we work with some of our other clients. So that’s really a important part, shows that our agency isn’t just working directly with clients that have social impact, but we are actually volunteering our time as well.

And then for ArtCenter, the same thing. I’ve learned so much from teaching, communicating your thoughts of visuals. I’m sure you know this, it’s very, very underestimated how difficult it is to be able to say, communicate in words what something should be visually. I don’t think we think too much about that, but it’s extremely hard and it’s definitely an art to that. I learned a lot of that through teaching and different personalities of creatives and designers and so forth that I think has also helped Pastilla. And also just teaching at ArtCenter as my brand, my personal brand has definitely just validates the agency, validates me and so forth. So it all works together in my head for a bigger vision.

Maurice Cherry:
Well, no, it makes sense. It all feeds into each other. I don’t mean this in a bad way, but the work you’re doing teaching, of course, that informs how you talk to clients or how you present the business to clients. But then you also say, “We’re not just an agency, we also give back to the community.” And so that is where Art Division comes in, where you’re saying, “I’m doing this to help out students that are interested in design or kids that are interested in design.” So it does all feed into each other, but I think what it does overall is it shows just how passionate you are about design, just outside of a client-vendor relationship. This is your lifeblood. You live and breathe this stuff.

Rudy Manning:
Exactly. Love that. That’s exactly it. Yep.

Maurice Cherry:
What do your students teach you?

Rudy Manning:
Patience. I think, number one, it absolutely keeps me on the cusp of the, I hate to say design trends, but how culture is affecting design. How each generation takes what we’ve done and reinvents it, takes what they see in their environment and mixes it up to have this new creative aesthetic and how that continues to evolve. Absolutely, I always want to make sure that I am not blinded by my past or my history of what I always thought the design aesthetic was. I always want to feel like I’m at the edge of what’s happening, if not what’s also how things are changing and looking even ahead of that. So the students definitely keep me on my toes when it comes to that.

Second is understanding different design, creative mindsets or personalities. Different students take feedback completely different. And how you have to be very agile and nimble in how you communicate things. It could be how direct you are. It could be how open you are about a direction. Some students are really great at giving, they need very prescriptive directions on something and they need to develop that. They need to know things aren’t going to be so prescriptive. You need to connect the dots yourself, but you still have to be somewhat prescriptive. And then other students, if you’re too prescriptive, they literally will get stuck and confused because they don’t really understand exactly what you’re saying. And there’s everything in between.

So being able to read, pick up on how a student is reading you quickly, that’s really important, and being able to adjust your communication style. And that’s the same for our design team in-house and also clients as well. Communicating to clients, like you mentioned, we’re all creative to some point and when we’re communicating visuals, I take those little tools that I’ve learned in communicating to the students and I borrow those things to communicate to clients as well when I need to.

Maurice Cherry:
Now, you are at a really unique vantage point, I feel. One, you’re an agency owner with Pastilla, you’re also an instructor, so you’re teaching the next generation of designers. How has being a design instructor informed how you approach Pastilla?

Rudy Manning:
It’s funny because we ended up changing the name of Pastilla from Pastilla Studio and in 2012 to Pasta Institute. It was supposed to be this sort of cheeky way to institutionalize something that isn’t really institutional and formalize it when it really isn’t formal. It was a very small studio then still. But there was something that made it feel like it’s established, but then at the end you’re kind of like, no, they’re a very buttoned down agency. So the one thing is that it was funny because the kind of person that I was and the designers that I would get, was naturally sort of a mentor and people would say, it’s kind of like a school where I saw designers really grow when they came to work at Pastilla and go and do amazing things, even after Pastilla.

And so that teaching part, I think was a part of Pastilla from the beginning, just naturally, I guess, maybe it just came from me or maybe just because I had to. Because I needed help and I needed freelancing and I had different people from different points of view, and that’s just my communication style. So that institute, I remember that now, it’s just Pastilla, obviously. We simplified it, but that part is still there. And for I would say a good eight years, every quarter at least, we had a different intern. I wanted to make sure that the designers that we have respect the interns and part of the work is that they do have to mentor. I’m mentoring as a creative director, the student, and also our design team that’s also working with the mentors is also teaching.

Teaching, it’s absolutely critical to any leadership. You can’t have a leader, not be a good teacher. You have to have somebody that can have that empathy of understanding that how to communicate to do something is an important part of being a leader and that not everybody takes or understands the same words or receives the same kind of communication the same way. And I think that’s an important part of being a good leader. And I felt like that’s an important part of Pastilla. And the creative team, the account team, the management team, and I try to continue to infuse that. Sometimes probably, I would say maybe the designers are like, “Oh my gosh, there’s too much work. I’m teaching and designing.” But I think in the long run, they’re going to see that this is some important tools that they learned.

So in short, before I was teaching at ArtCenter, I think we had that part embedded into our culture, that teaching impact or that element. Then I started teaching, that just got elevated, and then I just literally created with Pastilla, I would just have internship programs. So the students would come from ArtCenter. They’d intern at Pastilla for three months, continue getting taught there.

Maurice Cherry:
Now you mentioned with the education work you’re doing with ArtCenter, that part of what you’re teaching is about future strategic thinking. From your perspective, what do you think agencies can do moving forward to ensure that the future of creatives reflect this world that we’re in right now? Of course we hear a lot about diversity and inclusion. There’s always going to be some new bleeding edge tech, which right now is what AI, Chat GPT, et cetera. How can agencies start to move forward, making sure that this next generation of designers, creators, et cetera, really reflect the world that we’re communicating and creating for?

Rudy Manning:
I think one of the things, along the line of teaching, I feel like at least that was a feeling when I was in school, was that if you don’t come with a absolutely impeccable portfolio, you cannot work at some of these big larger agencies. This was the case. Thankfully, I went to ArtCenter, I had that experience, I had that portfolio at that time. But not everybody gets those opportunities. Not everybody finds those paths. Maybe they might have the opportunity, but they somehow didn’t have that one person that said, “Hey, take a class here,” or whatever. There’s lots of amazing schools in the world, in the country. But I feel that a lot of it starts in looking, when you’re interviewing somebody, agencies and design companies need to look farther deep into who that person is that they’re interviewing, way past their physical, where they’re at, at that moment with their portfolio.

Because for us to start developing or having the agencies and creative agencies, digital agencies, every kind of agency, reflect the real world, the designers that we have, the copywriters, the creative directors, the animators, the programmers reflect the world that we actually live in. We have to know that not everybody is getting the opportunities that everybody who’s working currently in the agency’s got, period. And to do that, we have to take some risk and we have to take initiative. I think the number one thing is to open our eyes to giving opportunities to people who are not at that moment fully polished to be working at that company. And there’s portfolio schools, there’s lots of different ways that somebody can advance themselves, but most of it is about the work. But you can get that experience sometimes working at an agency. If you have just a little bit of the excitement, the passion, the energy, and that natural creative tendency, even without having a finished portfolio, if you’re given the opportunity at an agency, you can develop that portfolio quick.

I know it’s not easy. It is not easy, and it’s expensive because the design teams, everything we do is labor. So things will take longer, the people. But I think in the long run, we have to give people the opportunities to, especially underserved, people of color when they come knocking at our doors as an agency and you see their work, you see where they’re at, not turn them down or away just because their portfolio isn’t fully finished. There is space for them to grow. And those, sadly, a lot of the opportunities that come are because of that network. And I understand, you get portfolios come at you 24-7, but every now and then I’ll get one and I’m like, huh. Their portfolio is not fully fleshed out. And they don’t have the ArtCenter, art school, art design, design portfolio, but there’s something in their personality, something in their CV, something in their work, one project, it could be that can show some kind of interesting perspective that you could look at. And if we’re looking closer, we’re able to maybe find some talent that just hasn’t had the opportunity.

I’ve seen that with Pastilla. One of our top designers that we have, I would say one of the top designers we’ve ever had at Pastilla didn’t go to art school like that. He went to a two-year school, it wasn’t a really fully flushed out program, didn’t have that kind of portfolio at all. We gave him that opportunity and he’s an amazing designer. So I think agencies need to be open to giving more experiences like that. That’s what I hope to do with Art Division is take that with the designers that go there, is find those ones that have that passion, be able to connect them. If the student wants to be connected, connect them to some of these other agencies. Just a simple, “Hey, check out this person’s work. I thought this. I thought this was interesting.” And giving them an opportunity.

Maurice Cherry:
I highly agree with what you’re saying. I was just talking to a colleague of mine, Ricardo Roberts. He has a agency in New York called Bien, B-I-E-N. They do an apprenticeship type program where they bring in designers, maybe they’re junior designers or maybe they don’t have a fully polished portfolio, but they help to give them that experience that they need in order to then get out there and really work, whether that’s with agencies, whether that’s directly with brands in house, more of those types of opportunities need to be available.

I agree with you, as I’ve talked to folks here on the show that have worked in advertising and such, agencies can be pretty stuck in their ways about the type of people that they want and the type of experience that they have to have. They have to have followed almost a particular script in order to just get in the door. This is even at smaller boutique agencies. So it definitely sounds like that whole world needs a bit of a paradigm shift, I think.

Rudy Manning:
Yeah, no, absolutely. I love that. I would love to hear more about his program. I think formalizing something like that is awesome.

Maurice Cherry:
I will connect the two of you after this interview. I will most certainly do that.

Rudy Manning:
Yeah. That’s awesome.

Maurice Cherry:
How do you stay creative and inspired in your work? With everything that you’re doing, I feel like you have a lot of input coming at you.

Rudy Manning:
I’ve always been a pretty curious person and I hope that I continue to be until my last days because I feel like that is the thing that hopefully will keep me up to speed on everything that is design at that moment. I would say design’s going to be completely different the next 30, 40 years. And I hope to know what’s happening and not be like, I would always say when I was in school with some of the older instructors, everything that we were doing was like, “Ah, everything looks the same.” And it’s like now I see some designers say the same thing to people in their early 20s. We have to understand things evolve, things change, and I want to be able to have that understanding. So staying curious and questioning and being, like I mentioned earlier, teaching and having young designers is a really important part of understanding that, how things evolve.

And so that definitely always keeps me fresh. I always have that curiosity of what is new, what is next, definitely keeps me fresh and excited. Right now obviously, everything happening with AI is really, really interesting to me. It’s something that we’ve always known is coming and we’ve seen it coming. And now tools are just more in front of us and the potential to be now in design where we’re going to see a total evolution of, and even fast forward of how we think and how we can be more hyper-focused in the creative and not so much of the doing. How we create is going to change as well. Even how to take simple things like a logo, what does that mean now in AI? Can a logo be so dynamic that it’s absolutely never static? Can a company have a logo where every customer has their own version because it’s that dynamic? Asking these questions I think are going to be super interesting. So always being on top of what’s happening, combining that with my experiences in the past, taking that in, I think that excites me.

Maurice Cherry:
What advice would you give for aspiring creative professionals out there? They’re heard your story in this interview. They see everything that you’re doing in the community. What advice would you have for them?

Rudy Manning:
Wanting to be, let’s say, own a design agency or just jumping into graphic design?

Maurice Cherry:
We’ll say wanting to own an agency because I feel like a lot of folks that I speak with now are definitely leaning towards more entrepreneurial efforts. Even folks in-house are trying to strike out on their own. So yeah, approach it that way.

Rudy Manning:
I would say, number one, you need to be extremely patient. We hear that. We know like, “Oh yeah, you got to be patient. Things come to those who wait.” But it really does. In that patience, you’re going to have a lot of times where you feel like you can’t continue. I remember the first 10 years when I started Pastilla, there was about three moments that I thought… Okay, I remember the first time was in the financial crisis. I thought, “Okay, crap, this really sucks. I don’t like this feeling. I don’t like this uncertainty. I don’t like this weight that’s on me.” And I thought, “If I make it through this and something like this happens again, I can’t continue.” And then four or five years later, boom, another blip and you’re like, “Crap. Dang it. No, I’m going to continue, but you know what? This is it. After this one, that’s it.” Then you get one more, boom.

And what’s crazy is that over time, you learn that those blips, those bumps, you just learn how to deal with them. You’re smarter behind dealing with them. It’s not that the blips go away, you just aren’t scared of them at all. You’ve faced everything and every single time you’re a better entrepreneur, you’re a better planner, you’re more strategic. You know how to handle the downturns. That tends to scare away people. I know because I had those thoughts and I thought like, “That’s it.” But every single time you have to have that faith of, “You know what? I’ve got to believe in myself. I think I can do it. I love this.” You have to love this design industry. You got to love what you do. You got to love your clients and who you work with, and being creative, that definitely has to drive everything because if not, you could just be a banker or investment banker or something because there’s other ways to make money.

But this definitely is a combination of a lifestyle. And yeah, obviously there’s financial reward with it as well, but it definitely isn’t easy. Then I would say consistency. It’s not a sprint, it’s definitely a marathon. And there’s I would say in that marathon, there’s a bunch of small sprints. It’s one sprint and then you go into one phase and you got a marathon, marathon, marathon, another sprint. But it’s the consistency, the compounding effect of all of those moments of sprinting and marathoning and sitting and waiting and moving that all compile together for the good.

I would say in terms of, I think probably the biggest thing is people always ask, “How do you get clients?” And things like that. I think for me, one of the things that I learned early on, and I learned this as a freelancer, and this might seem super simple, but to this day, it’s probably the main thing that continues to feed our business, which is show people the work that you do. You finish a project, show it to people, tell the story. In the beginning, one on ones. I remember I was freelancing. I’d finish a project and then I’d have seven or people that I wanted to share that work with. And I’d say, “Hey John, how’s it going? I haven’t seen you for a while. We should have lunch, da da da. Are you still working at blah, blah, blah? I just finished this project. It’s down around where you live. It’s a new identity. It was a lot of fun, da da da.” That’s it. It was like a PDF or jpg in the email.

That was the first five, seven years of that I continued to freelance work that then got to start the company. And to this day, that’s exactly what I do. Now, it’s more formalized. And we do more of them. It’s not just projects, it’s articles, it’s stories. It’s the same thing everybody does. But I was doing it very early on where I didn’t really have anything to say other than sharing my work. And it was very intentional and very sincere as well. Because this business is about relationships. It’s a lot about relationships.

So you treat people good, you do really good work. You do everything you can to make sure the client’s happy and that will pay for itself. And from there, you share the work with those people, they’re going to tell other people about that, about you. And that continues to build more and more and more.

Maurice Cherry:
Where do you see yourself in the next five years? What do you want that next chapter of your story to be?

Rudy Manning:
The past five years, we’ve grown exponentially. I feel that things are a lot more, I would say self-running, automated. The agency and the team is much more structured than it ever was. There’s some positive and negatives to that. The positive part is that it’s less weight on me. The positive part is that we can grow necessarily, not directly with me having to be on the ground every single second. There’s things that are built that can continue to feed the company on its own even without me. So those are the good things.

The downside is that there’s a lot of weight, or the downside I would say is that I do less creative than I did before, and I do more strategic thinking of the company. There’s been great things and I have to continue doing that. And I know in the next five years with that growth that’s happened, we have had some interest in people acquiring us, purchasing us. But I think we’ve contemplated a lot of those things in the past, especially last year and we continue to. But I think this kind of growth in the next, I would say five to seven years, is probably going to continue.

But what we’re going to do is, it’s a hard question because I think we’re in the middle of pivoting a little bit, but I would say potentially doubling or tripling in size to then have a bigger creative team, to serve more of the same kind of clients that we do, that we have right now. And where I feel, and that by note means we’re going to be a hundred million dollar agency or anything like that, but that’s going to be able to scale us to the point where I don’t have to do the kind of operationalizing, the strategic business work that I do on a day-to-day. I think that’s the goal. Where I then focus my time is on more of the relationship parts of the company, my relationships and how to continue to foster that and less being on the ground for the business right now.

To do that, we’re probably going to find maybe more partners to do that growth or maybe do some larger hires. We have to see. There’s some different strategies we have and options we have to do that. But I think double, triple in size than where we are now and me being less of those… Let’s say if we had another talk, Maurice, like in five, six years, I’m not telling you that I’m on a call six, seven hours a day, maybe three. And then the rest of the time I’m maybe meeting people or maybe more involved in Art Division or have some other nonprofit that’s maybe a part of not Pastilla or part of Art Division that is involved in the same kind of topics that we’re talking about, bringing art and design to youth to create more opportunities. Something like that.

Maurice Cherry:
Well, just to wrap things up here, where can our audience find out more information about you, about Pastilla, about your work? Where can they find that online?

Rudy Manning:
Our agency’s website is pastilla.co, so pastilla.co, P-A-S-T-I-L-L-A .co. You can also find our agency on Instagram. And our Instagram is, it’s Pastilla, P-A-S-T-I-L-L-A, Agency, A-G-E-N-C-Y. That’s her Instagram. And my Instagram also is Rudy, R-U-D-Y, M, V, so upside down A, V-N-N-I-N-G. So again, Rudy, R-U-D-Y, M-V-N-N-I-N-G. You can find me there as well. Yeah, those are my main channels. I’m also on LinkedIn. You probably just search me there. I don’t know what the exact profile name is there, but probably search Rudy Manning, you could find me on LinkedIn as well.

Maurice Cherry:
Yeah, we’ll find it. We’ll link it all down in the show notes. Rudy Manning, thank you so much for coming on the show. I think it’s definitely evident from your story, from the work you do out in the community, your education work, Pastilla, like I alluded to earlier in the interview, it’s clear you live and breathe design, but outside of that you have this sort of fiery passion to give back to the community and to also push the industry forward.

I think you’re doing it at a pace and a rate and a breadth that is inspiring for me to see. I hope it’s inspiring for our audience as well, for them to see what more can they do to try to really advance and push things forward. So thank you so much for coming on the show. I appreciate it.

Rudy Manning:
That’s awesome, Maurice. Thank you. Thank you so much for having me. Appreciate it. Awesome podcast. So thank you so much for having me again.

Sponsored by Brevity & Wit

Brevity & Wit

Brevity & Wit is a strategy and design firm committed to designing a more inclusive and equitable world. They are always looking to expand their roster of freelance design consultants in the U.S., particularly brand strategists, copywriters, graphic designers and Web developers.

If you know how to deliver excellent creative work reliably, and enjoy the autonomy of a virtual-based, freelance life (with no non-competes), check them out at brevityandwit.com.

Sponsored by Hover

Hover

Building your online brand has never been more important and that begins with your domain name. Show the online community who you are and what you’re passionate about with Hover. With over 400+ domain name extensions to choose from, including all the classics and fun niche extensions, Hover is the only domain provider we use and trust.

Ready to get started? Go to hover.com/revisionpath and get 10% off your first purchase.

Sean DallasKidd

If you have aspirations of being an agency owner one day, then you might get some great insight from this week’s guest, Sean DallasKidd. Sean is the co-founder and chief creative officer of DemonstratexDDW, and he uses his decades of experience to help brands define their story and communicate with their audiences.

Sean told me more about his new role, sharing what it looks like to run an agency from the C-suite and help it stand out from the competition. We also delved into Sean’s background, where he spoke about attending SCAD, getting into the publishing world, and how his shift to agencies helped prepare him for his current leadership responsibilities. Getting comfortable with being uncomfortable has been the secret to Sean’s success, and it’s definitely paid off! (Big thanks to George McCalman for the introduction!)

Interview Transcript

Maurice Cherry:
All right, so tell us who you are and what you do.

Sean DallasKidd:
Hello, my name is Sean DallasKidd. I’m partner, chief creative officer at DemonstratexDDW. I would say what I do is make brands culturally relevant, and that takes place from brand development, naming, brand architecture systems over to go-to-market strategies. So really trying to create programs and experiences that resonate within culture, drive talkability with media and can be shared digitally and socially.

Maurice Cherry:
How are things going so far this year for you?

Sean DallasKidd:
This is a very interesting year. We’ve got lots of tensions in the US, globally, and so I think this year has been another year of quick adaption to socioeconomic sort of movement that’s happening around lots of new technologies that are turning on and a lot of disruption. So it’s a very interesting year to roll up your sleeves, learn a little bit more, and I’d say get creative.

Maurice Cherry:
Is there anything major that you really want to accomplish this year?

Sean DallasKidd:
Let’s see. This year, I think the main goals for me probably start with AI literacy from a sort of personal and business growth perspective, also want to take care of my people. I think as we’ve kind of seen on channels like LinkedIn, being able to create a business that can sustain over time, that puts its employees and its culture first, that’s one of my sort of big goals. And then obviously, working with brand partners that want to do very interesting, fun, provocative work.

Maurice Cherry:
Any sort of personal goals though for this year?

Sean DallasKidd:
Personal goals, to see more of the world. I’ve been historically a big traveler and the other thing that I love is food. So the over the course of the pandemic, have definitely been leaning more into traveling via my mouth and stomach. And so, this year I would like to actually get out into the world and see what’s happening in different countries and regions in the US.

Maurice Cherry:
Let’s talk more about DemonstratexDDW. As you mentioned, you’re president and chief creative officer there, pretty recently as of last year, right?

Sean DallasKidd:
Correct, correct, correct. What’s really interesting with DemonstratexDDW is last year we announced the acquisition of Deutsch Design Works, DDW, which is a 27-year-old branding agency that was based in Sausalito. And so, what we did was acquire the agency for the brand building capabilities that they had, and we thought it was a great fit because Demonstrate focuses on go-to-market strategies and campaigns and programs, and so this gave us the opportunity to not only bring brands to life and market, but really start with the fundamentals, which you often find missing when you’re working with brands. So what are some of the cultural artifacts built into the brand DNA, the purpose, how do you find actions, and so we felt as though being able to help set the bar and the tone at the upfront and being able to pull that into a market will do nothing but good things for our brand partners that we work with.

Maurice Cherry:
What does a typical day look like for you?

Sean DallasKidd:
Ooh, let’s see. Phigital, it’s physical and digital. So Zoom meetings, hybrid meetings, writing some design, and then the most fun part of being a business owner is Excel spreadsheets of things. That’s one of the sort of growth spaces when you become more of an executive creative person is getting right with the Google Sheets.

Maurice Cherry:
Now, was it a big shift moving from partner to president once this acquisition happened?

Sean DallasKidd:
I would say it was different, but it’s been an accumulation of experiences over time. I think that my history starting in publishing, moving into earned media, moving into advertising has become a brick by brick process. The transition didn’t or hasn’t to date been as dramatic of a shift because I have a network to help support and educate me on components and parts I might not be as familiar with on day one. So I would say the transition wasn’t crazy, not to say it’s not crazy. You get what I’m saying?

Maurice Cherry:
Yeah. I mean, I would imagine whenever there’s a acquisition or things like that, you’re bringing more people in, of course, you’re merging company cultures, so there’s always going to be, I think, some clashing or things just as that acquisition tries to reach equilibrium.

Sean DallasKidd:
Exactly. You always have different ways and means, ways of working, different kinds of processes, lead times, you have different billing cycles, all sorts of stuff that you have to work out. I would say the best case scenario in any merger is a mullet. It’s business in the front and a rock show in the back because you’re trying to figure out how to get one set of systems to work with another without clashing in any sort of crazy way. But luckily for us, we’ve been able to make it through that stage and I think we’re starting to get into stride right now which is great.

Maurice Cherry:
And now you mentioned that part of your typical day still has some design in it. Are you still available to get hands on working with clients and with campaigns?

Sean DallasKidd:
Yes, yes. I feel as though I’ve always had, you would say, a problem with people who guard themselves off in the ivory tower, right? And so, one of the things I always tell our employees is that you want to have lived experience before you can recommend a strategy to someone, and in order to stay current, you have to do. So even if a design direction that I might develop doesn’t get picked, it helps me stay current on tools, timelines, amount of resources, different design trends so that when I’m talking to brand partners, I’m using language and referencing things that are happening now and not when I did it back in the day, 5, 10, 15 years ago.

Maurice Cherry:
I had an agency owner on here a few years back, I’m not going to call out who it was, but for folks who listen to the show, they’ll probably remember when this happened, but this person was mentioning that they have an agency and was talking about how they were the only Black agency owner that they knew and that. He’s like, “I don’t know about any other Black agency owners.” And I was like, “Well, that’s not true. I’m pretty sure there’s others out there because I’ve had them on the show.” But have you noticed during your career in advertising many other Black agency owners?

Sean DallasKidd:
I’ve definitely kept an eye out on it, but I will say it’s hard when your head’s down managing the work and the business to take the time to do the proper recon and outreach to folks. It’s a bit of a balancing of time and energy, but I definitely have seen the spark and the growth in that space. I know a couple of folks myself that have some small studios and then there’s some folks that I’ll look out to and see what they’re doing in the New York area that are really tearing it up which is great.

Maurice Cherry:
Yeah, I mean, they’re out there. It’s certainly like you said, they’re at all sizes. Whether it’s small studios, big agencies, et cetera, we’re out there, but it’s about visibility as well too.

Sean DallasKidd:
Yeah, I would say it’s visibility, and then there is, I would say, the system of agency and connection. And so, I think that… What’s a good way to phrase it? The hurdles for growing an agency to the point to where you get visibility is tricky when you’re not a part of the club to start. I could be a great designer, but do I have the connections to be considered or backing to be considered for some of these medium size, large term clients is a different story, right?

There’s a procurement process as you start to grow your agency and payment terms that shift, and do you have the financial backing and resources or credit to be able to invest that manpower into going through one of those processes for the chance to win the business, and then can you float the business in a way that can deal with payment terms of a larger client on a bigger scale, right? You might move from payment terms of I’ll do a project and things get paid out 15, 30 days, 40 days to 90 days to 180 days as you get bigger and bigger clients, and so you see there’s different hurdles in order to be able to even get a bite at the apple that you have. I think that’s one of the tensions that you face as a Black agency owner historically which is why I think that’s one of the reasons why you have a lot less of them with that level of visibility.

Maurice Cherry:
There’s clients out there that are paying net 180?

Sean DallasKidd:
Yes, there are. There was, forgot what the brand was and I won’t even mention it, but it was a CPG brand, consumer packaged good brand that got called out on Adweek and in the industry because I think they wanted their payment terms to be a year.

Maurice Cherry:
Oh, come on. A year?

Sean DallasKidd:
A year. And so, when you talk about diversity, equity, inclusivity, you can have a very talented agency, just call it a graphic design branding agency, and you have a staff of five to seven people, you’re doing really good work, and normally you’re getting paid in 30 day terms. Now that bigger client might be like, “Oh, I’ll want to work with you,” but then they give you a term payment of, well, instead of you getting paid a month later, you’re going to get paid six months later. How’s that diversity and equity model going at scale at that point with these small shops? And so, those become some of the bigger systemic issues, I would say.

Maurice Cherry:
I mean, you’re right, the balancing act of making sure that your clients and your cash flow is terrorist or at least coming in at a point where it appears to be consistent cash flow, especially when you’re paying employees, that’s tough. But net 365, that’s wild. Wow.

Sean DallasKidd:
Yeah, that’s [inaudible 00:15:31].

Maurice Cherry:
What do you think makes DemonstratexDDW stand out from the competition?

Sean DallasKidd:
I would say the way in which we stand out from the competition is we take a culture-forward lens with the work that we do. What we really try to do is drive this term we call talkability amongst target audiences that we’re looking to drive brand awareness, consideration, or conversion with. We also focus on brand or business objectives, number one. We start there, and as an integrated agency, we do, like I said, brand, naming brand architecture, packaging, but we also do integrated communication. So that’s paid media, earned media, social, digital content strategy, traditional above the line advertising. And so, what we look at are all the different levers of communication to drive those business objectives and then based off the audiences that they’re trying to engage with, what’s true to the brand, and timeliness as well as budget, what’s the right mix to help drive that messaging home to help spark conversation overall.

That really stems from, again, that background that I’ve had of being in earned media, being in traditional advertising and being in publishing, and at each step always seeing that for some of these integrated programs or brand initiatives, the PR team is not in step with what the advertising is doing and the advertising team isn’t in step with what the PR team is doing. As we look at this crazy new communications landscape, it’s kind of like it’s better to look at it holistically and then go based off these sets of truths, what is our best route into the market, looking at all the different components and parts we have access to across paid, earned, shared, and owned channels.

Maurice Cherry:
Now, not to give away any trade secrets or anything that you’ve got cooking at DemonstratexDDW, but what do you think are some of the biggest opportunities in the creative industry right now?

Sean DallasKidd:
Well, for me, I definitely would say AI is the biggest opportunity. I know people are frightened about it, ChatGPT and everything else that’s happening, but I feel as though with any new technology there’s definitely going to be category leaders, new roles that come into the market, and so becoming literate in what AI is and can offer and how you can work with it is the biggest opportunity. Actually, in my mind, Web3 is AI because if you think about being able to become an expert prompter, a creative prompt strategist to work with an AI machine so that it can find information that can then be fact checked to create more nuanced, quickly adaptable copy or design territories for you to explore, I think that’s a really interesting job opportunity. There’s some cultural anthropology that you can mix in with it.

I think there’s a lot there because it helps you tie in not only sort of brand DNA, but it helps pull in to design trends that could be pulled live or recalibrated and personalized for specific audiences. I think it could be a very compelling tool, but at the same time, the literacy is important because you got to know what the trade off is, right? I think we all ran into social as consumers of it, not realizing that the trade off was us and privacy and our data. And so, everyone is excited to use things like ChatGPT right now, but one of the things for me is what’s the terms and conditions? Are they going to get a piece of it?

You go and say, “Oh, great, I’m going do a Super Bowl ad using ChatGPT.” Will they have some sort of way on the backend to identify that this copy or this concept came from that, and then they want points? So I think we need to really understand what the technology can do and also who’s making the technology because whoever’s making the technology is creating a certain lens on where the technology starts to look for information.

Maurice Cherry:
Now we’re recording this the Friday before the Super Bowl, and I bet you there’s going to be a Super Bowl ad that has some kind of ChatGPT, I don’t know, punchline or something in it. I feel like it’s got to be in there somewhere.

Sean DallasKidd:
Oh yeah, yeah. I would definitely say. There are agencies that are losing sleep right now because three weeks ago everyone was hot to trot with ChatGPT and Ryan Reynolds did a ChatGPT ad, and everything they’ve been working on in the last year just got thrown out the window and they’re going to do something so that they’re timely and can make a splash of some kind.

Maurice Cherry:
Well, I mean, you know what we won’t see during the Super Bowl? Crypto ads. I remember those from last year, and boy, have the times changed.

Sean DallasKidd:
It’s funny. To your earlier question of staying in the work, the reason why you have to stay in the work is because you don’t want to give bad strategic advice to a brand partner. The easy trap for someone my age that got into social at the MySpace and early iteration of it and kind of settled, gave up on Facebook, does Instagram primarily to not stay current, right, to not check out TikTok and BeReal, and some of these sort of crypto based social channels and some of these niche social channels, you fall into the trap of recommending old and then you become irrelevant, right?

Maurice Cherry:
Mm-hmm.

Sean DallasKidd:
And so, agency is all around the fight for relevancy, and I think the separator for us is knowing the nuance between relevancy for demo that everyone typically goes after 18 and 34 and nuance around the psychographic drivers and different folks because share of wallet goes from anywhere from a 10-year-old up to octatarian. People have needs, and the nuance comes from understanding what’s going to be that right audience that you need to tap into. So you have to stay current.

Maurice Cherry:
Oh, absolutely. Now we’ll get more into your approach and your work a little bit later, but for now, let’s get into your background. You’re in San Francisco now, but you’re originally from D.C., is that right?

Sean DallasKidd:
Correct. Southeast D.C.

Maurice Cherry:
Tell me about growing up there.

Sean DallasKidd:
Well, let’s say the D.C. today is not the D.C. of the years I grew up. I grew up in ’80s in Reaganomic D.C. It was definitely a lot rougher around the edges in Southeast where I was. But I would say one of the things that always kept me curious and creative, I always loved to draw as a kid and since, and I was also a latchkey kid, so I chose to take advantage of latch keydom, if that’s a word, to take advantage of all the free museums and zoos and public transportation you had as a minor. I’d spend my summers going down to the National Mall, going over to the Smithsonian or Museum of Art, Portraiture Gallery, all that kind of stuff, and so that’s really what sparked and maintained my interest in creativity.

When I went to high school, I was lucky enough to get into an architecture program. So I actually started doing that in 9th, 10th grade, actually drawing plans and really had a great teacher. His name was Mr. Fotos. He was think of angry Santa Claus with a Greek accent. He taught us everything and was just an amazing teacher, and that allowed me to go to SCAD, Savannah College of Art and Design for architecture actually. I think I started on the sophomore year as a freshman just because of my portfolio and what I learned, and then got into graphic design and illustration along the way.

But the lesson he taught me, and I guess this has always been ingrained in me, he said, “If you’re going to be a great architect, you need to be able to design from the building down to the spoon.” And so, that was one of those sorts of thinking of where it’s not just about the whole, the big idea. It’s down to the details and the nuance, right? And so, that’s just been a philosophy that I’ve carried with me which helps you dig a little bit deeper to kind of understand how people move through spaces, or how people engage with an experience or a design, or how a message needs to be flexible to be able to sit in an internal communications program and be explained so that your workforce is on board, and how it can help inspire creative outputs out in the real world, whether it’s on the side of a bus or some sort of 4D, 3D billboard, or if it’s an augmented reality experience. So really being able to be transmedia and understanding does this thing have scale and flexibility.

Maurice Cherry:
What made you choose SCAD?

Sean DallasKidd:
Well, the city, downtown Savannah is beautiful. It’s hot in the summer, but I would say I loved the architecture there. The teachers are cool, the programs are really interesting, and for me, as you look at the, I would say the standard East Coast go-to design schools, the Pratts, the RISDs there was less… Well, I’ll just say, it was a less sense of entitlement and bourgeoisie in Savannah.

Maurice Cherry:
Okay. Okay.

Sean DallasKidd:
I felt like I could actually learn things and experiment versus do things the way the teacher did them.

Maurice Cherry:
Gotcha.

Sean DallasKidd:
I kind of saw a bit of that trap as I was looking at some of the different schools of… I think for anyone that’s taking a life drawing class or something like that, you definitely have those teachers that are like, “This is the way to do it,” and it happens to be the way that they do it. And so, I definitely wanted a place where it seemed like I could be more collaborative with different departments as well, and so SCAD just really stood out in that way.

Maurice Cherry:
Gotcha. I gotcha. Yeah, you were in college, I think we were in college right around the same time. You started in like the late ’90s, like ’99?

Sean DallasKidd:
Yep, yep, yep.

Maurice Cherry:
Graduated in ’03?

Sean DallasKidd:
Yep. [inaudible 00:27:33].

Maurice Cherry:
Yep. Same here. Same here. Tell me what you remember from that time.

Sean DallasKidd:
Ooh. Well, when you say that, the first thing that comes to my mind was 9/11, just because I remember that moment very specifically. I was an RA at SCAD and woke up to one of the towers falling.

Maurice Cherry:
Wow.

Sean DallasKidd:
That was just a trip of a day, and the ripple effects of that are felt today. This is why we take our shoes off at airports, right?

Maurice Cherry:
Mm-hmm. Yeah.

Sean DallasKidd:
So 20-something years later. But beyond that, I would say some of the things that really were interesting to me at the time was the evolution in music. I remember there’s a funny moment when I was walking around River Street or that sort of downtown area in Savannah, and I saw a bus outside for this band called OutKast, and I went, “I wonder what they’re all about.” Little did I know that the OutKast was coming to us all, right?

Maurice Cherry:
Yeah.

Sean DallasKidd:
It’s the same sort of time when the Gorillaz made their first album which is just a mix of every kind of genre possible with layered animation for this sort of virtual band, and they’re still making amazing music now. And so, it was just a really, I think, funky time because it was this age, similar to now, of transition, right? So when you’re a designer, a couple years prior, everyone was using hand tools to do typography and all that sort of stuff, and we were there at that moment when it was like, “Okay, so we’re getting into Pork Express and we’re doing Adobe,” and you’re learning these new programs. Now in hindsight, you know those teachers barely knew those programs too because it was so new.

And so, you’re getting into the age of digital publishing in the middle of this sort of like what’s happening in the world because everything, America’s the safe space and now this thing happened, and everyone’s unified for six months. It was just a wild time. Then you’ve got this technological boom happening, and then you get sped out into this world where a couple years later, an iPhone pops out. It’s a very reminiscent, minus the pandemic part, what’s happening today. It was just chaos.

Maurice Cherry:
I mean, you really had to be around during that time to realize the gargantuan amount of technological advancements that have happened from 2000 to now. I mean, you talk about iPhone, but then just a whole bunch of other technologies and stuff, even the way that we do design online. I mean, back then design was slicing up a table in Dreamweaver and posting that on the web. Now it’s all browser with layouts and flexbox and all that sort of stuff, not to mention other service side technologies and stuff.

I mean, I was in college in ’99. I had started as a computer science major, computer science, computer engineering because I wanted to be a web designer. I had cut my teeth in high school in the computer lab at my mom’s job because she taught at a college. I cut my teeth reverse engineering websites, and I made something on GeoCities, and my mom was like, “Why you putting our address on the internet?” I was like, “We live in rural Alabama. Nobody knows who we are.” But I went to school, went to Morehouse, majoring in computer science thinking that was web design, right?

Sean DallasKidd:
Well, it was. I mean, I remember I had to do HTML coding because I was taking some program classes, and for people who don’t know, there’s a program called BASIC and Pascal.

Maurice Cherry:
Oh yeah, yeah.

Sean DallasKidd:
C++. I was taking all those. The internet back in the day was code. ,And then you’d upload images and like you said, you’re doing slices and all that, and now you’ve got… But what was cool about that is lacking today, it feels like to me, is that there was all this experimentation, right? You’d have these Easter eggs on the side, you’re like, “[inaudible 00:31:50] scroll left or right, up or down. Am I navigating through this weird wormhole?” Whereas now everything’s on these sort of modular boxes, and so there’s shades of vanilla essentially, and then however powerful your imagery is, but people are also picking up the same sort of trends on en masse at this point, which is one of the sort of fears or outputs that might become AI down the line is Marvel movie number 856.

Maurice Cherry:
Right.

Sean DallasKidd:
But I think back then there was a great experimentation and we were all sort of learning and playing around, and I think that was probably part of the happiness people were experiencing originally with sort of the Web3, NFT space, right?

Maurice Cherry:
Mm-hmm.

Sean DallasKidd:
It kind of had that same energy. It had some wrinkles to it. It had a little bit of dirt in the fingernails of we’re figuring it out and we’re going to make art and it’s going to be awesome and we’ve got our own closed loop, and then [inaudible 00:33:00].

Maurice Cherry:
I attended a metaverse conference in the metaverse. Was that last year? I think it was last year. It was last year I’m thinking about it, yeah. I attended a metaverse conference in the metaverse, and one of the sessions this guy was talking about digital real estate, and he’s like, “Yeah, we have this digital world and you can buy these plots of digital land.” Somebody during the presentation bought a $10,000 plot of land that only exists in the metaverse, and it made me think of, do you remember The Million Dollar Homepage?

Sean DallasKidd:
No.

Maurice Cherry:
The Million Dollar Homepage was basically, it’s probably still online, to be completely honest, but it’s basically you bought pixels on this homepage. Say you had a 88 x 31 ad tile or something, you could buy the area of that 88 x 31, and it’s like a dollar per pixel and put an ad up there. People were just buying spaces and putting up all kinds of stuff on there, and that’s what it felt like. It’s like this digital real estate that doesn’t really exist, but you’re kind of buying into it for the hopes of it becoming something in the future which I guess is like real real estate.

Sean DallasKidd:
It’s so funny to me, the whole digital real estate now. Whatever it starts to morph into in five, 10 years will be what it is, and everyone will come back to this podcast episode and laugh at me for saying it, but the reason why real estate exists and has value in real life is because we live on one planet. It’s literally a finite resource, right? This is where we breathe, hopefully, and have food and light and all this sort of other great stuff. And so, there’s X amount of space for X amount of people, and there are prime pieces on it.

In a virtual world, much like if we didn’t have to worry about time or eating or breathing, we live in this vastly, huge universe like in the real world. The digital world is the same thing where it’s like it’s infinitely large. There’s, in actuality, no real prime real estate because you can own one square inch and have it feel like a million square inches or you can just go to a different section of virtual town and make your own thing. Yeah, the real estate part is quite interesting in terms of how they attain it or how they attribute an X, Y, Z coordinate to it. It’s not a place.

Right, right. Yeah, in a way, it just sort of felt like it was kind of just like you’re buying a plot in a subdivision because it only exists in that particular metaversal world that we happen to be in, because the metaverse is many different worlds. It’s not, as you’re sort of saying how earth is one finite resource, the metaverse is a whole bunch of stuff.
Yeah.

Maurice Cherry:
Yeah.

Sean DallasKidd:
Yeah, I could literally make my own planet in the metaverse, in my own solar system in the metaverse. So why do I need to buy a 50 pixel by 800 pixel piece of property across the street from Snoop Dogg’s one place?

Maurice Cherry:
Right. And Sean, he paid $10,000 for it, and the guy was wearing an NFT suit or something, and he kept showing off like, “I can show off my NFTs on my suit.” I was like, “This is giving me a headache. I don’t even know what to make of this.”

Sean DallasKidd:
That’s probably a slam. I think there’s always what’s presented on the surface and then what’s happening on the back end and part [inaudible 00:36:48], “Hmm, did you really buy that? Was that a plan?” Like, okay.

Maurice Cherry:
Yeah. Those early days, in the 2000s, as you mentioned, on the web, it was really sort of experimental with publishing and stuff. Now after you graduated, tell me about your early career because you got into media and publishing afterwards, right?

Sean DallasKidd:
Correct. Yeah, so I had a couple of gigs prior, but I would say my professional career really kickstarted in the publishing world. I worked for Future Publishing, Ziff Davis, and Maker Media. I started over at Ziff Davis and now Ziff Davis was really about video game magazines. I was working on their PC focused gaming magazine and then started getting really curious. I’ve always been, I would say, hardworking and curious, sort of always looking to push my edges. And so, I was proactive about reaching out to other publisher or other magazines if they needed help designing pages. And so, I was very proactive and worked with Electronic Gaming Monthly or PlayStation Magazine or Xbox Magazine and all these things just so I can get more experience quicker.

Then I transitioned over to Future, which is like the sort of, they were essentially Coca-Cola and Pepsi as holders, and so they had the reverse version of everything. While I was at Future, I started their custom content division, and so that was working directly with brands to develop branded, independent magazines, websites, apps, podcasts for folks like Best Buy or NVIDIA, brands like Paul Reed Smith Guitars, did a crocheting magazine, all sorts of stuff. And so, that helped do a couple of things of giving me a brief and a business objective for the brands we did partner with, and then gave me the license to concept and develop an entire magazine, for example, that would service those needs and what those sections would be and sort of design language that would go into that, not only that printed piece, but the digital footprint as well.

And so, it was a really great time because at that moment we were making the transition, the death of print was happening, as I said at the time, and so not only were we doing magazines, but it allowed me to do websites, it allowed me to do apps because the iPad had come out. And so, we were looking at how do you translate brand DNA into a digital platform space, which was a really interesting moment that I would call back to the sort of tensions that are happening today. It was really weird because people had this sort of cognitive dissidents between this magazine I’m holding is the brand. And it’s like, no, the brand is the brand, what your brand stands for and your tone and how you sort of approach things and it happens to be a magazine, but it can also be a website, it can also be a podcast, it can also be an iPad app or a tablet app.

You can start to see the split of people that didn’t want to adopt or learn, and then the people who leaned into it, and I’m always been the one that just leans into the chaos because it never looks as crazy on the inside as it does on the outside, and that’s where all the opportunity is. And so, that was a really great moment to go and take that experience over to Maker, because instead of working on multiple brands, this was making one brand that had the business, Maker Media, it had the printed magazines, Craft Magazine and Make Magazine. It then had a body of different websites and then it also had Maker Fair.

And so, now you’re looking at how do you take a brand and have it stretch out into these various forms because they found themselves there and then create order around it and really sort of bring it home so that it could grow and thrive in the midst of the quote, unquote, “death of print.” It’s still around. It’s still doing very well because I think part of it was learning that your brand, believing and knowing that the brand is bigger than the mass at the end of the day or has the ability to be.

Maurice Cherry:
Now, was it kind of a shift to go from working in these publishing companies to going in-house, working with agencies? You also have worked with JWT, worked for FleishmanHillard, now you’re at DemonstratexDDW. Was it a big shift making that change?

Sean DallasKidd:
Yeah, I mean, the days are different. It was interesting. I feel like I had a soft entry, I’ll call it soft, because before going into fully external agencies, I worked in-house at Discovery Communications. They did Discovery Channel, Learning Channel, Animal Planet, and so I was helping with the Investigation Discovery launch and show launches there as well as Velocity Network, and so that was the agency inside. You had to develop a pitch concept, pitch it to the marketing team or the showrunner and come up with marketing campaigns that way. And so, that was a good segue before going fully agency because FleishmanHillard is one of the big global PR agencies, so was J Walter Thompson which is now Wunderman Thompson, and so one’s Omnicom, a sort of agency holding company.

I guess I always did this. I went from Pepsi to Coke or Coke to Pepsi, and so went over to J Walter Thompson and did the same thing, but I think the transition at Discovery really helped out because it gave me insight and understanding on what are the different outputs that come in advertising, what the digital lens, what are people looking for in terms of making commercials or campaign programs. It started to really give me the language and became a good test bed for me in that transition.

Fleishman gave me, I would say, my PhD in quickly pivoting your mind. I worked not only nationally but sort of globally as well. And so, I worked on everything from sort of data security to consumer goods to FinTech to healthcare, you name it. And so, I would get briefs that range from internal communications programs, crisis management programs, general awareness programs, and really focused on creative and content strategy while I was there. At nine o’clock in the morning, you’re talking about the future of electronic payments in developing countries. In the afternoon, you’re talking about the future of medicine. And so, your brain has to be able to pivot because you’re going to be in a room with a bunch of C-suite executives talking about and really having to understand the background information and sort of ways in which culture was moving.

Maurice Cherry:
Now, from this point where you’re at in your career, what does the future of agencies look like?

Sean DallasKidd:
I would say that the future of agency is going to have to be personal. I think that interesting part, and this is why I think AI literacy is so important right now is it gives smaller, medium-sized agencies an opportunity to scale up outputs if done properly, if integrated properly into your workflows. I think that because we’re going to have so many different digital touchpoints that are super niche, you’re going to have to get very personal and personalized in your messaging. I think that the physical interaction and experience is going to be highly coveted, and people are going to appreciate that a lot more because no matter how amazing that virtual experience is, people still need, just have a genetic need to engage with other people and smell the same thing, be in the same room in a very real way. That’s not to say that in 20 years there’ll be some matrix version of that reality, but until then I do think that people getting together and engaging with each other is going to be super important, but I do think those will be more curated, more selective kinds of engagement points with folks.

Maurice Cherry:
Yeah, I think there’s been so much talk about data-driven outcomes and seeing what the data says and all that, but at the end of the day, you’re still dealing with people. I mean, even with this AI stuff, I see so many videos on TikTok and YouTube about people telling you how to craft the perfect prompts for GPT and all this sort of stuff, and I think what it’s still boils down to is that at the end of the day humans are still the entry point.

Sean DallasKidd:
Well, you’re still going to be the decision-maker at the end of the day.

Maurice Cherry:
Right, right.

Sean DallasKidd:
If you are essentially at a 12th grade level and GPTed your way into life and you find yourself there as a 26-year-old, really do the math on that. You started out and you GPTed your way from 18 to 26, the wheels are going to fall out from under you because at a certain point you’re going to be in a room and you need to be able to answer the questions and defend the solution to someone else, and if you don’t know your stuff, because you’ve been essentially the parrot for this fishnet of an answer that your AI gave you, the trust won’t be there. That’s what all the access and the ability to repeat opportunity comes from earning, cultivating trust over time, and that’s a human thing. And so, if you get to the point to where you are pointless, then you won’t as a person have any need to be in the room with people. And so, I don’t know if I lost the point on that one, but I do think that’s a bit of-

Maurice Cherry:
No, no, no, I think you’re spot on.

Sean DallasKidd:
Yeah, it’s a balance.

Maurice Cherry:
Yeah. What have been some of the most important lessons you’ve learned in your career?

Sean DallasKidd:
Being comfortable, getting uncomfortable is the most important lesson I’ve learned in my career. I’ve touched on it over the course of our conversation, but being proactive when transition happens, jumping into the chaos, because I firmly believe that’s where the opportunity lies, and when that new messy space opens, if you’re over there first, you get to make mistakes on a small scale, right? Imagine putting out a bad tweet when Twitter just started or putting up a lame Instagram post when Instagram first started. That’s the best time to do it. You can learn how the audience interacts on the channel and get feedback and get better. You do not want to be doing that high wire act in the middle of the Super Bowl for the first time.

Getting into that space, understanding the language, understanding the nuance and the flow of energy there gets you smart on it because people will eventually come there because that’s where all the changes, that’s where all the new is, that’s where all sort of cultural influencers are being born and sparking new kinds of innovations. Eventually everyone’s going to get there. So always being comfortable with getting uncomfortable is hard, it’s uncomfortable, but I think the reward there is the most fruitful for a long-term career as a creative, not as somebody.

I think you’ve probably seen this over the years, there’s lots of people who used to be a designer, used to be a creative, used to be in marketing, and the difference is not just some of the systemic stuff, but it’s staying relevant, right? In order to stay relevant in today, you need to be smarter than what’s happening today, which means you need to be ahead of the curve a little bit, and that’s a hard thing to keep up with. You got to be the Lil Wayne of the industry. He’s been doing it since he was 12, so he just stays up there. And so, you got to be the Lil Wayne of whatever you’re doing in life.

Maurice Cherry:
I still remember Lil Wayne from those CDs in the ’90s, No Limit and everything.

Sean DallasKidd:
Yeah.

Maurice Cherry:
Yeah.

Sean DallasKidd:
And Cash Money.

Maurice Cherry:
Cash Money.

Sean DallasKidd:
Yeah.

Maurice Cherry:
What is it that keeps you motivated and inspired? Because I can imagine this is not an easy thing to sustain, this kind of thing with being comfortable with being uncomfortable because you’re sort of always kind of jolted out of balance in a way, I would imagine.

Sean DallasKidd:
I mean, to be very straightforward with it, family keeps me motivated. I have a kiddo and she is a spark of joy, and so that situation keeps me motivated to keep wanting to do better from just a sort of fundamental lizard brain section of my mind. Creating room and space and opportunity for her and creating, I’ve seen my dad do that so I can do it and I can one-up him, right? Having that yard stick in front of you I think is a great driver.

Then I would say for me another motivator is just I am curious and I feel like my brain is creatively broken. It’s like a faucet that doesn’t turn off. You hear the conversations with people going through these dry periods, and I’m not trying to toot my own horn or anything there, but it’s like my brain just does not shut up with things it wants to do or think about or see. I think that comes from living that, trying to have a more balanced life of… And you ask me the question, what are some of the hobbies and things that you like to do that kind of spark you, those are the sustaining breaths that help keep passion and curiosity going.

And so, when you cultivate or try to cultivate a life where Monday is not a dreadful day, Monday is just Monday, and now the dreadful part of the day is, well, now people are going to expect me to respond to an email because it’s not the weekend. But at the end of the day, I’m writing or designing or talking to people or trying a product or trying this or going to an event. I’m like, “That’s dope.” It’s a good thing and it just takes effort to stay on the ball, but I think that just comes with it.

Maurice Cherry:
Now, who are some of the people that have helped you reach this point in your career?

Sean DallasKidd:
I would like to think myself for… No, I was like, I couldn’t remember that new [inaudible 00:53:25] quote. I’d like to thank myself for the hard work. But honestly, I think it’s a bit of that, just you got to know your center and you got to know your truth and you got to play to your strengths and you got to build up your weaknesses. I’ve been blessed in meeting very kind people that have cracked the door open and given me opportunity. That comes again from the fact that proving or being in that sort of energy state where you are proactively looking to grow. I’m more willing to open the door to someone that I see that’s working hard and looking to grow and looking to be challenged than someone that’s sitting on their laurels. Luckily, the people I’ve engaged with were willing to open the door.

Then I have a great network of friends and colleagues to be able to bounce ideas off of, hear what they’re going through, take lessons from that, and make connections and references. You can’t do everything by yourself. It’s one of the sort of points that I always teach. I always stress to my daughter, she wants to become the next Hayao Miyazaki. And I go, “That’s awesome, and Hayao Miyazaki not only is a great drawer and a writer and all that sort of stuff, but he also has studio space that he has to pay mortgage on and employees, and so he has a CFO and he is got da, da, da, da, da. He is got to work about licensing deals and everything else.” So it’s like you got to have a good network as well and make those connections.

Maurice Cherry:
Where do you see yourself in the next five years? What kind of work do you want to be doing?

Sean DallasKidd:
Man, on my bucket list, I want to do some shit in space. I really want to do something in space.

Maurice Cherry:
Okay.

Sean DallasKidd:
I’m going to put that energy out on this podcast. If somebody knows someone in any country that’s doing something in space in the next five years, it would be great. I think that would just be a trip. I don’t want to go underwater. I don’t want to go into any of that deep sea stuff, but space would be kind of just like I feel like that would be a mind-altering, crazy thing and inspirational thing to do. Something dealing with logistics. Doesn’t that sound cool? I’m working on an interplanetary logistics program, or I’m like, this new bougie hotel that’s in low earth orbit, and so I’ve got to do a promotional campaign or video or collaboration thing. That just sounds dope to me. So that’s what I want to do.

Maurice Cherry:
I interned with NASA for two years when I was in college. So it’s funny because we were talking about college and you mentioned 9/11. 9/11 was one of a turning point for me too because the program that I was in, the way they had it set up, it was based off of Ronald E. McNair who was in the Challenger explosion, and so his family put together a foundation, whatever. So I was a McNair scholar at Morehouse, and the part of the NASA thing was that you interned at NASA for two years and then afterwards you basically had your pick of any NASA facility to work for. So I was like, I had done my first one in California, did my second one in Alabama, and I thought I was all set, until 9/11 happened, and then the funding shifted towards the creation of this new department called the Department of Homeland Security.

Sean DallasKidd:
[inaudible 00:57:22].

Maurice Cherry:
Yeah, and they were like, “Yeah.” I remember they called us all into the office and they were like, “Yeah, the seniors will still be able to go forward to work at NASA facilities,” and I was a junior at the time, but they were like, “the rest of y’all, you’re on your own.” I was like, “Oh man.” I say all of that to say that I think now, certainly 20-plus years in the future from when I graduated, there’s probably more opportunities for designers to work with NASA and space than there were back then. I think back then it was still pretty, I don’t want to say confined to academia, but you’ve got even people on TikTok who are budding astrophysicists that are doing stuff that has to deal with space and everything. I feel like it’s possible.

Sean DallasKidd:
Well, yeah, I mean, definitely think it’s possible. My mom actually used to work for NASA. She’s a mathematician, and I think the terms they used to use back in the day though for people like my mom was data analysts.

Maurice Cherry:
Ah, yeah.

Sean DallasKidd:
Give them a data analyst title versus a data scientist title, save yourself a hundred thousand dollars, and they’ll hide those fingers in the back somewhere. I do think that the opportunity today is a lot more open, but the work, it’ll be curious to see how willing people are to do the work because you always see do the work as the hashtag, but the sort of underlying effort, sustained effort of doing the work is the great equalizer in a lot of ways. You will get tired and then you’ve got to get that seventh and eighth wind at the end of the day.

Maurice Cherry:
Look at you. Your mom was a hidden figure. Look at that.

Sean DallasKidd:
Yeah, it was weird. It’s funny, I’ve got these old photos and stuff of her on some airplane thing.

Maurice Cherry:
Really?

Sean DallasKidd:
Well, the thing about D.C. is back when I was there in the ’80s, it’s like a bunch of little Black ladies that run all the sort of inner operations of the government at a certain point because they were all the secretaries and they were working in, they were the data analyst or this kind of thing, and they were just working in the back.

Maurice Cherry:
Wow.

Sean DallasKidd:
Yeah.

Maurice Cherry:
Well, just to kind of wrap things up here, where can our audience find out more information about you, about your work, and everything? Where can they find that online?

Sean DallasKidd:
I am so Google-able at this point in time. You can literally type my name in, but you can follow me at kidisgoat, K-I-D is goat, G-O-A-T. You can look at the company, we are demonstrate.com or you can look at ddw.com if you’re interested in branding work. But that’s where you can find me. Look me up, I’m out there.

Maurice Cherry:
All right, sounds good. Sean DallasKidd, I want to thank you so, so, so much for coming on the show. I really think that your authenticity and the passion that you have for your work really shines through. I mean, even just from your early days of getting into publishing with the work that you’re doing now for Demonstrate, I like what you said about having to be in the work so you kind of stay one step ahead. It’s that sort of thinking that certainly I think is going to take all of us as creatives far, but certainly it’s been such a boon for your career and for your life, and I’m really excited to see the Sean DallasKidd project in low earth orbit one day. I think it’s going to happen.

Sean DallasKidd:
Thank you so much.

Maurice Cherry:
So thank you so much. Yeah, thank you so much for coming on the show. I appreciate it.

Sean DallasKidd:
All right, thank you.

Donate to Selma Tornado Relief

United Way of Central Alabama, Inc.

We are raising money for Selma Tornado Relief through United Way of Central Alabama to help serve victims of the tornado that tore through Selma, Alabama on Thursday, January 12th. Donate now, or text SELMA to 62644. Send us proof of your donation, and we will match it 100% (up to the first $1,000 donated).

Thank you for helping fund Selma’s recovery!

Sponsored by Hover

Hover

Building your online brand has never been more important and that begins with your domain name. Show the online community who you are and what you’re passionate about with Hover. With over 400+ domain name extensions to choose from, including all the classics and fun niche extensions, Hover is the only domain provider we use and trust.

Ready to get started? Go to hover.com/revisionpath and get 10% off your first purchase.

Jeffrey Henderson

Being confident with your creativity will take you far as a designer, and this week’s guest is a perfect example of that. Jeffrey Henderson is the founder of AndThem, an NYC-based creative collective that focuses on building creativity and business within Black and brown communities.

We started off talking about plans for the summer, and then Jeffrey spoke about his innovative agency model and how he uses it to help give back to the next generation of creatives. We also talked about his 15+ year career as a footwear designer for Nike, Yeezy, and Cole Haan, and how he brings that knowledge to his current work with creating his own footwear designs. Thank you Jeffrey for being a shining example of what it means to use your talent to bring the world to your feet — literally!

Transcript

Full Transcript

Maurice Cherry:
All right. So tell us who you are and what you do.

Jeffrey Henderson:
So I’m Jeffrey Alan Henderson I’m a creative based in Harlem, New York, team of about 10. We take on, everything from product design to content creation.

Maurice Cherry:
How’s the year been going so far?

Jeffrey Henderson:
Oh, the year’s actually been pretty good. And we actually had a nice growth year. Not in terms of state business, business has always been pretty standard even when we went through trials and tribulations of COVID. But I think I brought in some young folks for the first time and made it official kind of last year. And so we had some growing pains in terms of people just learning how to be creatives in sort of corporate settings and non corporate setting. That was very new to a lot of us. And having an agency built like that this year has been a, I think, an extension of that. But now that everything’s opening, the team is definitely more seasoned, so a lot more exciting because of the things I know we can take on. So it’s been pretty good.

Maurice Cherry:
I’m pretty sure people listening can hear the birds in the background. So, it sounds like you’re hit like some idealist spot right now, which is good, which is good. I think after the year. After, after the year, I think all of us have had a little bit of a mother nature’s is gladly welcome at this point. Do you have any plans for the summer with the agency?

Jeffrey Henderson:
Oh, this summer where we’re trying to get back together during, I guess January of this year, we had pretty much all 10 folks in Harlem, essentially, about five of them stayed in, we have a studio here and apartment that we actually rent out as an Airbnb, but when we don’t, it’s actually our studio. So everybody was sort of working together. And that was, I guess, when the world was still kind of closed. And so we’re going to try to do a little bit out of that again, since we can’t really travel to the places we need to travel to get work done, we’re going to just come back to New York, settle down and keep growing.

Maurice Cherry:
Now with And Them and sort of the changes that have happened over the past year. I mean, you said business has been pretty steady, and I know that you do a number of different services. Can you just talk a little bit about what And Them is and how did you come up with the name And Them?

Jeffrey Henderson:
And Them comes from when I was a Nike employee in Japan. I had a lot of free time in the mornings where I would have to work with the team that was in the U S. And so during those phone calls every now and again, I’d have an hour in between and there was a creative by the name of Kevin Carroll who’d just left Nike, he’d written a book, Rules of the Red Rubber Ball. So he became sort of internet famous at that point, hired a team, he had about six people doing everything from PR to creative, strategy. He had been working with them for about three, four months and it just wasn’t clicking. He ended up calling, I think, myself, Jason Mayden who’s now at Fear of God Athletics, D’Wayne Edwards who runs PENSOLE. And he’s like can you like, just sit on these meetings and help me out, but I don’t want to threaten my team. He started introducing us as you know, was just Jeff and him. It was just D’Wayne and him kind of nonchalantly. And so the joke was, we just became an them like this [inaudible 00:06:00].

Jeffrey Henderson:
I just kept it. Kept the name because it also represented the fact that when we work with, whether it’s Yeezy or FC Harlem or local restaurant around the corner, we’re not trying to showcase our brand we’re trying to showcase your brand. We were doing something with Revision Path, it would be Revision Path and them. It’s just us trying to help out folks who sort of need, I think, a boost. I live right down the street from Harlem Hospital so there’s always a siren now and then.

Jeffrey Henderson:
In the last year we definitely picked things up because what really happened was this is probably three years ago now I was working on a project, launching Everlane’s new footwear line that they put out the tread. And while I’m working on it, Michael Price with the CEO, he keep asking me like, how do you do X, Y, Z?

Jeffrey Henderson:
And I’d be like, oh, you just call this person. And it’s like, I just saw him asking questions. And he kept looking at me like you have all these people, why don’t you set up an agency? And I was like, yeah, nah, that’s too much responsibility. Like I did all that. Like at Nike you have a report. Like it was all just too much. But a year later it was like, okay, all these people who, and it sort of came by, honestly, in that people who were working on teams individually, when I got there, they just sort of were like, yo, can I do a project with you , you have anymore? So I just kind of brought them with me. So they kind of became my and them. So I just, if we want to call it, I’d be like, yo, why don’t you sit on this call and won’t you take this and if there’s money left on the table, we’ll split it. So that’s sort of just evolved to the fact that I just had a few really talented young folk who probably weren’t either seasoned in corporate or had already tried corporate and was like some just wasn’t feeling right about it so they were like, I’d rather hang out with you, work on projects. So I became normal. So we’ll be doing a lot of product design and graphic design. And then one of my best friends, creative director, who he taught himself to be sort of art director holding the camera. He was doing, working at a not-for-profit basically counseling kids and got a camera. And we were coaching his basketball team together and he said, you know, my dream is I want to shoot the NBA in the Olympics. And he’s like, that’s my longterm dream. That’s what, that’s what I want to do in life. Three years later, he ended up doing that. Like, it was all sort of like this whirlwind of like, he worked for the Nyx, he shot for FIBA in Brazil, the Olympic basketball games, like, oh, I should’ve made my dream a little bigger than that. And so he sort of come on with his team. So all together, we tackle soup to nuts, anything from product creation, manufacturing to content creation. So that’s kind of where we are and what we do.

Maurice Cherry:
It sounds like it all kind of came together pretty easily. I mean, since you had already this network of people and you had creatives that were drawn to you because of your work, it sounds like it didn’t take much to kind of build a team.

Jeffrey Henderson:
I think it really goes back to one of the things that happened In my old Nike days, it was very much this thought of you kind of were put on a track or plan to be a design manager or design director. A lot of times people would be put in design manager roles so they could kind of learn the procedures, the processes, the operations part, so that when they became a design director, they at least know what those things were as we started looking at bigger picture in terms of product creation. So I kind of took a big tune to what the operation side was. I was, I think, I learned from some really great people who just knew how to grow and manage people because I needed a lot of that because I was literally making up as I went, I didn’t have a design degree. So anybody who could help me, I was in their office, left and, trying to figure out how I screwed up. I just took those lessons and while I was working on the creative side, building all those other kind of tools and components taught me how to get the most out of people and how to help them get the most out of themselves. When I ended up in random spots, I wasn’t just worried about is the color right, is the engineering proper is the functionality working, is the design modern. It was also how you doing as a person? Are you doing the right thing? And so it really like became, I didn’t realize it was that obvious until this young woman, Lauren Divine who’s great material designers, [inaudible 00:10:18] This is probably the early days we were over in some broken down office building And I was probably in and out of LA for maybe a year and then one day, I guess I didn’t show up for three months cause I was either doing something else I didn’t didn’t need to be there and I got there, she came and gave me a big hug and she’s like, finally, you’re back our manager I was like, your what? I was over here, drawing shoes what do you mean? She’s like, no, no, no, we need like this set up and this meeting organized and this, that and the other, and this is what you do. I was like, okay, honestly, didn’t sign up for that, but the reality was I did sign up for that. I mean, I just became a mentor to a few people who just sort of needed the ins and outs every now and again, it wasn’t like I was their manager manager, but I was, I don’t know, helpful in helping them get things straight when they needed it.

Jeffrey Henderson:
Especially if you weren’t in a traditional corporate environment where people were set to be your manager or mentor. So that sort of turned into an easier way to then run this sort of organization that we just pick projects and started out really me just no one, some people who were like, yo, you want to do this project? Yeah, I got nothing better to do, but I mean, it’s real. Like I ended up falling in love with things that I know nothing about just because it’s different. Like we have a project now with a friend of mine, she’s CEO at this wellness brand, wellness and beauty called ASA there and it’s all about circularity, sustainability and reality is like, I walked to the conversation, going to look, I’m not like a big sustainability dude, that’s not my thing thing. I kind of know about it and I’m more interested in it because I have learned over the last, I think two years, how much it affects black and brown communities first.

Jeffrey Henderson:
And so I have a little bit of interest in it, but I can’t say it’s like, I wake up everyday like, oh, I care about this. But ever since being in this project, like now I’m like forced to like, oh, this is real and I’m going to the grocery store I see tons of plastic and I’m like, oh, how do I fix, how do I help? How do I like live here to these compensations? So it just becomes a, I don’t know, we find ourselves in new conversations that are helpful because I think it’s, it helps us to become creative, but it also lends we have a skillset that we were using somewhere else that now we can apply it to something that we all care about.

Maurice Cherry:
I think that’s, especially when you have a, a collective like that that’s, what’s important is that you’re able to bring your expertise and the mind trust of the people that you’re working with to a project or to a brand it’s not necessarily that you’ve done it before, but the collective knowledge is enough where you can go into the project and still know what needs to be done.

Jeffrey Henderson:
I think that’s very true. I think our, I don’t know, collective unit is hard enough. I don’t know questions, concerns. We’re not people. I think some of the more senior folks on our team, like we’ve heard it before. It’s very enlightening that we have sort of like these 22 year olds who chime in knowing that look, I don’t know everything, but here’s what I’m thinking and it sort of like it brightens up our eyes to go, oh, never would have occurred to the old crowd in the room as to think about things like that because like we’re not digital natives or we’re not focusing in certain places. We don’t go to certain parties. We don’t hang out in certain worlds and I think they ended up bringing something new to the table while absorbing what we offer them so when they get to touch base and go, oh, let’s see what Lowy Frames is like a place that does fine art restoration and gilded frames. That is a new conversation for all of us. But the young folk, they don’t realize it’s new to us they just, everything is new to them. It’s kind of eyeopening to watch them grow.

Maurice Cherry:
And you know, and one thing that is really important to note here for people that are listening too, is that , these are young creatives and you’re giving them the ample space to make these sorts of decisions or determinations or comments or observations. It sounds like in a safe environment, if they say something that may not go over well with the client or something, they’re not immediately asked, I would imagine like it’s sort of a, they have a space to, to fail, which I think as a young creative is probably important to have because there can be so much out sort of like outdo pressure placed on black and brown creatives to kind of be brilliant right out the gate and not make mistakes.

Jeffrey Henderson:
I think it is sort of, I mean, the conversation we were having before we got on here about the, I think understanding of what it means to be black in any corporate environment to be brown in any corporate environment, the idea that this is like a second culture, a second language that you have to bring to the table and learn, I think often the idea of assimilation or the idea of fitting in or not making people uncomfortable. Like it was so ingrained and in the reality is I think I was trying to be part of that in the nineties, I was just, wasn’t really good at it because I was trying to go, okay, I know your music I noticed that. And I really didn’t because I really wasn’t listening to it. But I think there’s this innate need to sort of like, see if you could fit in and our group is like, we don’t really have that as much as like, you need to know this part of the culture in order to do the job. If you don’t, don’t sweat it. I mean, if you make a mistake as you’re going through, because it’s all different and it’s all new, pay attention. And I think that’s the part where I, from all my failures of walking into situations and not knowing my first days, going from Nike to cohort where it was like, I wasn’t making sports shoes and that’s all I knew to oh, now we’re making a small number. Like Nike, the minimum you could do in a shoe with like 30,000 pairs of shoes, I got the cohort and I was like, oh, we did 30,000 pair. They were like, we’ll like, I’ll be celebrating with 30,000 pair it’s just a different mindset. I didn’t know. And I think I kind of have this, I’m happy to open my mouth and sound dumb 10 times out of 10, just because let’s get it out the way cause I don’t want any assumptions of me walking out the room, not really knowing, I think having my team, watching me say stupid things all the time and I do it for almost for their entertainment. I still call it tic-tac, I still talk about things, old guy, just so they know, I’m not afraid to sound stupid in the meeting and you should be okay because as long as you know, which is supposed to know and you do your homework, you’ll be good. And I think that’s, it’s really, uplifting to see these young black and brown folk be able to hold their weight and going to conversations as well as watching whoever the client is kind of go, oh, y’all know what y’all doing. Like yes we do. That’s all good.

Maurice Cherry:
I mean, I think that’s, I mean, honestly just for me as, a designer, as a self-taught designer, that’s just even great to hear. I mean, I’ve had other studio owners and such that have been on the show and I’ve even talked to like just studio owners through AIGA and other design organizations and it’s true. Sometimes if there is a leading creative at the head, like you would be with, with And Them, there’s almost this need for them to come off as the creative expert. Like they have to be the captain of the ship and you are the captain of your ship, but at least what you’re showing is that you’ve built enough camaraderie with your crew. So you all can come together and work on things and it’s not just you dispatching people to do work. You know what I mean?

Jeffrey Henderson:
No, it’s definitely I think, and you talked about it, getting people to come in and do podcasts I think there’s, on top of being black or brown in the industry, I think the conversation around being a creative also comes with a certain expectation. You may actually be an introvert or you might actually just get put in boxes and the sales team and marketing team be like, oh, well don’t talk to them till you want to have something creative and cool. But then when to drag the cool out of them. And I think to me, that’s what kind of puts folks in a box they’re afraid to talk there’s like a lot of this, that and the third. And I think I was lucky enough to be placed in environments where I like for real in the last two years, that’s when my friends laugh all the time. I don’t want to be on podcasts, I don’t want to talk, I never want to hear myself talk, but it’s just what it is. But I also know that folks are like, I learned something from you can you do that more often? It’s like, all right. It’s just easier if I can’t call everybody on the phone so here’s the podcast and I’m just going to ramble on, I think for hours at a time. But I think the idea that someone can offer you an opportunity to stand up in a meeting and give your options. And I was at Nike and I do believe I should have been like not fired, but somebody should have, could have reprimanded me over and over but they were like, yo, this is, this is how you grow and these are the bullets you take, you just come in and like, say something.

Jeffrey Henderson:
And I think there was quite a few people like who were Nike like, oh, didn’t say it but I kind of felt that like, oh, like Jeff’s getting run cause he’s black. Or he used to go in there. Like I could be completely wrong, but yo, that’s how I felt like thinking that. But I also know some people were like, yo he’s in the room cause he was bringing something different and all y’all had the same skillset so even if it’s not what you think is the right answer, we’re going to let them go and if it doesn’t work cool, but if it does work, it’s going to work in a much different way than you guys. And I think I was given enough room, like the fact that I went in to quit when I was at Nike, because I was feeling like this wasn’t going the right place and they sent me to basically run for [inaudible 00:19:29] in Japan. And I was like, okay, it was wild. But I think that it’s a case where there were the right people in the right rooms who were talking about this a lot, like the difference between mentorship and sponsorship and I’m kind of back in mentor mode, but I think having the idea and notion, I started understanding once I got at a higher clip at Nike that I didn’t have to be somebody who’s mental, I just need to go into rooms and be like, why aren’t you highlighting this person’s work. And basically looking at people like they were wrong, if they didn’t, I didn’t know whether they were doing good work or not I was just asking them and if they feel guilty about it, that should probably tell them something.

Jeffrey Henderson:
But I think that level of sponsorship became important and even though the mentoring was there, but I think having, and I know people who did that for me, it was either told them he asked her or I sort of knew, or I know that I would get no, no, no, no, no, then it get quiet for about a month and then next thing, Hey, we think you should do this opportunity. When somebody says something, clearly somebody says something so that I think is a part that seeing more of that from folks in or outside of corporate work, it’s just kind of important.

Maurice Cherry:
Now, And Them does a lot of different things. It’s hard to, I guess sort of pinpoint exactly what you do. Like if you go to the website for example, and click on FAQ it’s questions that sort of allude to the services that you could provide, like developing products, designing products, shooting actions, shooting commercial, shooting style, making logos, these are all services that we can do as long as you’re asking the question on what is it that we can do for you for your project.

Jeffrey Henderson:
Yo, I love you. You do all your homework. So reality is our main strengths, if we have people who help build Nike product, Yeezy product, Everlane, especially footwear, that’s our main bag. Then I kind of went out of my way, when projects and apparel came out, I was like, I need people who know how to do this. And I just saw that I literally went on LinkedIn and was like black and brown people who do apparel, please check here. The funniest joke about a member of our team, Shauna K is I was in the line at FedEx on 125th, and in walks behind me, Dapper Dan’s assistant Ashley. I look at her, she looks at me and she’s like, what do you want Jeff? I was just looking at her, like I wanted some, I was like, I need a black woman and she was like, I know who you need.

Jeffrey Henderson:
We didn’t discuss exactly what I meant by that. That could have gone a thousand different ways. But I was like, I want a black woman creative who is just starting out because we need to round out this team and we didn’t have that on a team. And she was like, you need to meet Shauna K, just finish FIT, she’s looking for work, getting a bone that was probably on a Friday. Miss Shauna came on a Tuesday, W]we had our first meeting to work on a Friday. That’s how quickly it went. But I think that’s the part where we knew we had product creation folks. I wanted more folks to kind of round that out. Then John Lopez on his side, again, shooting the Olympics, work for the NYX’s he’s dragging me around like, I just rented this $70,000 camera for a day Jeff let’s go out and have some fun, like, okay, I don’t know what that means. So being able to do those big, specific things were important, but we had both worked at meaningful places. Then we brought in Brie La Bossier who is sort of like, keeps us all saying as a kind of design manager, project manager, kind of everything. So what ends up happening people like, can you do this, can you do that and it’s like, well, I remember when I first left Cole high, I was sort of like free to do anything. I was like, I am not designing shoes ever again. That was my thing I wanted to do since high school, I was going to design shoes. So I had a good 15 year ride of doing that. I was like, yo, I’m going to do everything else I’m done to wear shoes, like start my new life.

Jeffrey Henderson:
Like I’m going to do branding, graphics, marketing, whatever it is, I’m not going to do shoes anymore. Two months after that, I was on a plane to go do Yeezy, it was just ingrained in me. But in those two months I started writing more. I started this random e-comm site with a bunch of my friends just to sell t-shirts, basically to ourselves, called Good Things. I was learning how econ works. I was learning a little bit about SEO and digital and all these other pieces that just started to round out. As I started getting deeper into conversations, I was like, oh, once you get through that first layer, you kind of know enough to be dangerous. Then we thought I’d taken on projects. And like our learning path really came with working with kind of nonprofits and small businesses because I didn’t know how to make a website or do anything.

Jeffrey Henderson:
But there was a restaurant that I ate at pretty much, three times a month, 4 times a month. He was like, yo, I need a website. Okay. Let’s build it. Let’s figure out what that looks like. Let’s figure out all the pieces behind it. And so working with people to kind of figure out and small businesses and nonprofits to kind of learn at least the lingo, how it works, sort of brought us to the stage of, oh, now with our knowledge of, anything from Nike to the New York NYX and NBA and Yeezy, oh, okay. We can start taking this to more people in different ways and definitely either being the conversation we were having before, intentionally this is going to be a black and brown group of people working on stuff. And so you can hire us intentionally cause you want black and brown.

Jeffrey Henderson:
You can hire us intentionally because you want a diversity where you’re just hiring us because we are good, we don’t really care. We’re going to come in and it’s going to have like we jokingly laugh, we had to do a photo shoot and we’re like, who knows somebody, wait. Like we can’t just because it was for a brand. It was this wasn’t a, like we’re trying to cross over, it was like, it was literally for a brand that has, I mean, all the founders are white and it’s like, yo, we don’t want them to look like they’re doing black face by, oh, everybody in their ad is black, a brown, like this should be pretty diverse. But in order to be diverse we can through some white folks in there, like we look across the room like who do we know? But it was this funny game of like, we don’t know, no white folks, but.

Maurice Cherry:
I just have to pause there. That is, to me, that is hilarious because the inverse of that probably happens in every creative studio at least once a week. Yeah.

Jeffrey Henderson:
So we are like the exact opposite. And one of the things that’s like amazing is we had a basketball shoot and this happens pretty much with every client, especially in color. And some say it like, and they even say a day one, or they say it, at least when they get to a photo shoot a week or product on the table is that one of the models came out. We had a shoot that was supposed to go from 2:00 PM to 6:00 PM in the park. We had some gears set up or got to shoot when it got dark. We all showed up one time at two o’clock we’re getting shots in and eight o’clock it was pitch dark. This was fall. That was probably like nine o’clock. We’re still out there still shooting good night shots. One of the models, like he was leaving on a bike.

Jeffrey Henderson:
He was like, yo. And I had to record him saying, he’s like, yo, like I’ve been in shoots before. And sometimes it’s your homeboy and it’s cool. We all hang out in the end product is like, okay. Sometimes I’m at like these professional shoots and it’s all good, we all know each other and we’re good but you know, in and I’m out cause work to do. He was like, this was like the party with real work. He was like, y’all onto something. And it’s that vibe that again, we’re doing things like in ways cause we don’t know any better. We’ll do it professionally, we’ll have the call sheets up, we’ll have all the emails and testing codes, all the protocol, new we’ll look up at Brie because she’s worked at like startups and stuff.

Jeffrey Henderson:
You will look up and Brie, because she’s worked at like startups and set up organization, things like, oh, you got to sign your paperwork. They don’t do the insurance. You want to showing up. At the same time, we’ll be out there enjoying each other’s company in a way that’s relaxed and a barbecue sort of atmosphere, which a lot of folks look at, like, I don’t know, but then what ends up happening? Like we laugh, cause it’s like the young crew, they’re like, yo, they go get an internship somewhere else. And they’re like, this is not we doing over here. And I’m like, okay, well we get some more projects and we can tackle some more work for you. So we’re doing something to have a little fun, but it’s definitely, it’s definitely the other side of the coin in terms of it’s just black and brown and it’s kind of what it looks like.

Maurice Cherry:
I mean what it really sort of boils down to, I think is two things. One you’re introducing to these creatives, at sort of the beginning stages of their career, a new possibility for what work can be, which is, or for what creative work can be, which is that it’s infused with play. We’ve had a lot of people on the show that are in the advertising industry and such, and they always talk about the long hours and the shoots and none of it sounds fun. They’re able to be creative, but it doesn’t sound like they’re really enjoying the job, you know? I think the second thing is that you’re inviting in this new tradition of this is what creative work can look like. So you’re saying yes, you can do this and also it can be fun. It doesn’t have to be stuffy or bureaucratic or anything like that. Yes, there are certain protocols that have to get done, but the magic and the environment that you’re able create is how you get your best work.

Jeffrey Henderson:
This was probably midway through dependent. It was maybe three months in and the team was feeling a certain way cause we had just, well, we had set up, I was looking for a full studio for us to work out of. This was probably end of 2019. Because I wasn’t finding exactly the space I wanted I sort of was feeling a little grumpy about it, at the same time I was working with the spot on 118th Milbank Children’s Aid Society. And it’s a afterschool program set up in Harlem basketball courts and swimming pools kind of have everything. When Zion Williamson lost his shoe, he did it on the algebra courts of Milbank, but it also has these classrooms, they actually have a onsite nursing office. So it’s pretty well-developed. And so the classrooms needed a little update. So I went to the folks there I’m like, look, tell you what, instead of me paying for a regular lease, I’m just going to update one of these classrooms.

Jeffrey Henderson:
And we’re going to work here in the mornings until two, when kids show up. Would that work and they, before I could even finish, they’re like done show up whenever. So we put some big screen TVs in, we put some tables, chairs, we were getting prepared, then COVID hit. So we kind of got locked out like everybody else. So the team was still in a certain way cause they had gone to two or three meetings and would just get to know each other and they were liking the vibe, but we shut it down from soon. Brie, our project manager, also runs a community kind of center for creatives. So she was like, we gonna have book club. So Saturday mornings from nine to 11, like one Saturday morning, Saturday mornings, we started meeting and having book clubs. What was happening was there were elements that were going over the young folks head just in terms of here’s things you ought to know whether it was in design or government or sales or e-commerce, whatever things that need to be had, or we need to discuss we’d discuss it.

Jeffrey Henderson:
And so she set up these meetings and buy a book. It was more like here’s an article to read or a the Netflix video to watch. And so we discuss it and three or four in, I was like, we’re taking away from their Saturdays. I was like, maybe we should turn it down a little. So we took a week off. They complained like nobody’s business. And were like, yo, why are we doing book club? Okay. And some of this was because everybody was sort of quarantined. Everybody was locked away. And so I thought, okay, we’ll do this bit because everybody’s locked away. Once we all get to go out and see the world, we’ll slow it down, did not stop. It just became this thing that everybody did together had conversations that were sort of like, this is serious and this is a safe space.

Jeffrey Henderson:
By then, we all got to know each other. So we give each other grief like nonstop, but it’s sort of a safe space for creatives to kind of, we show our work on Wednesday, Wednesday afternoon. That’s when we talked about work, work, work. But on Saturdays, and it’s not mandatory. Some people want a squad, like they’re like, no, I don’t need that. Cool. But the other half they show up religiously and the other place they go, well, let me see what the topic is. And then I’ll drop off. There was definitely this added piece of like, there’s just a conversation that, especially for creatives, especially for black and brown folks, being able to, I think, chop it up in that that sense is special. I mean, you kind of have to make space for that.

Maurice Cherry:
I liked it. There’s a section it’s not on the And Them side. I think it’s on the good thing site. That’s called book club where you sort of have some writings and things. I want to talk about that later. And I know we spent a lot of time talking about And Them, but let’s kind of shift the focus here because really this interview is about you. You’re originally from Ohio. So where you grew up, what was it like there?

Jeffrey Henderson:
That’s funny cause my wife and I laugh about this all the time is that my, wife went to stolen. So it’s a big deal. She’s from Philly. She went to Spelman. So she definitely talks about HBCU and what it meant. And it was never like my sister went to Wilberforce, going to HBCU was never anything that felt like I needed to do because, and I credit, this is like, we’re looking at 30 year anniversary. Or what is it? Yeah, 30. I graduated from high school, 30 years ago and 91. And I graduated with, out of the hundred kids in my class. It was 96, black folk, just black. Like one side of Baden was, is black, black, black, black, black, like just all black. And so, and I would joke with people like, I didn’t know, white people until I got to college, like literally, like I knew white people from the folks that went to our school weren’t that many or I saw them on TV.

Jeffrey Henderson:
So I would joke like white people were kind of imaginary. Like, it wasn’t a real thing. I learned about cultural and all that, it just didn’t really exist. And I never met anybody who was really like that. And so there’s a certain confidence that I had of being… Only having to worry about my culture. And so when I got to college, when I got to Purdue, it was very much like, oh, here’s another culture. I was like, okay, cool. But now I just care about engineering. Like, all I want to do is get into design and Nike and I’m supposed to study this so I’ve never worried about embracing anything of them, I’m just going to focus on school. And so after two years of that, I actually, at the one year I was like, yeah, I’m done would be in the middle of nowhere. Let’s go have some fun.

Jeffrey Henderson:
So I moved to Atlanta, nothing but black folk. And so that became a thing. And I think when I left and went to Nike, it was a strange sort of weird balance of me trying to figure out what was, what, and I honestly try to, and I don’t even know how to put it, I was trying to fit in, but I guess I wasn’t really trying that hard cause like everybody I knew was basketball, sports, marketing, brand Jordan. Like it was just all the black and brown people like it was. And I kind of hung out with whoever, but that’s just where I’ve found myself, other people who, I don’t even know if it was like, I found them as much as they were like, yo, we’re doing these things. You want to come hang out. And they were the normal things, like whatever, if it’s a barbecue or whatever.

Jeffrey Henderson:
And it was like, cool. I don’t know that I went out of my way, but it was this confidence that none of us really settled in until I moved to Harlem like three years ago. And when I got to Harlem, I was like, yo, this feels just like, they know how this feels just like being in Atlanta. And one of the things that kind of brought it up. So we did this project with the Apollo and it was about sneakers. And about education and someone had, was like we have to tell people why we’re doing something at the Apollo around sneakers. And I was like, no, we don’t, we don’t have to tell anybody. Like, if you ask somebody about sneakers and they’re black, the culture kind of says, they’re going to tell you something about it. They will tell you they couldn’t afford something.

Jeffrey Henderson:
And they going to tell you that knew somebody who had it. They going to tell you their own personal story, but we don’t have to have a conversation about why. Cause you’re the Apollo like is blackity black, black, black, black, like it’s just there. And I think that part, going back to Jefferson township, they know high aware, like our Italian immigrant history teacher went out of his way to make sure we understood that Lincoln didn’t free the slaves because he liked black people. He went out of his way to make sure like, nah, like this is what you need to hear. And that was just a school we grew up in. So like when I got to other places, like really that’s what y’all are. Whether they were black schools, white schools, like we learned it a hundred percent the way I think is discussed now. It was never a question for me or any of my friends going up.

Jeffrey Henderson:
I would say it’s a wild ride for me. It was the best place to be from, a little too small for me. Definitely getting out to the rest of the world was meaningful, but I would not replace. Oh, by the way, they know how it has its own sort of history with crime, drugs, sneakers, and everything else to where the most prominent sneaker mall in all of America was the little mall on the west side of Dayton that had the best foot locker sales, period. When I got to Nike, sales people were like, Salem mall. They did a lot of business. If you track east St. Louis, Dayton, Ohio or Memphis, it’s where underground railroad, there were a lot of stops, three major ones. So it’s why Wilberforce the central state are there. It was a lot of black folk who work there. When drug money started coming and drugs started working their way north, those were the same three places that folks stopped. They know how it kind of grew, music and drugs. It was a big thing especially in the late seventies, early eighties.

Maurice Cherry:
We had one other person on the show from Dayton. hannah Beachler she was episode 300 back in 2019. You said that initially you kind of like said it really quickly. I was like, wait a minute, what else do I know I’m going to show has been from Dayton. Cause I remember at least one or two other people. But her specifically, I remember because of that episode, but were your parents really supportive of you going into design? I’m curious, you know, you said before, if you ask any black person about sneakers are kind of, they’re going to kind of already have a cultural connection to it. So I won’t ask you that specifically, but were your parents kind of behind you going this route with your career?

Jeffrey Henderson:
In no way, shape or form based on this. My mother was a teacher and the reality is she didn’t care what I did as long as I tried my best and did my best, she was a person who, no matter what it was, she put that art on the refrigerator because you did it and you worked really hard and she was a middle school teacher. So she kind of had that in her, you can do whatever you want. I believe in you, yada, yada, yada, to the point where you almost didn’t believe whether she meant it or not. Cause she said it like everyday at all times, but you always had someone who was in your corner. So I think my mother wanted it to happen because I wanted it to happen. But you have to realize like this was 1991, sneakers weren’t a real thing.

Jeffrey Henderson:
And it was sort of a side conversation to the point where it wasn’t till I got to Cole Haan where the question is why does Nike own Cole Haan? Because it wasn’t making any money for Nike, the brand. And it was because an ADA still Knight knew that the industry common thought was if you wanted to make money and sneakers, you had to sell brown shoes, sneakers didn’t make money. And so he bought Cole Haan in order to make money. Well, fast forward, he and a few other people made sneakers like the regular topic. So sneakers weren’t a real thing and the reality is my father, who I didn’t have like the best relationship with, he didn’t say anything, he watched because I was getting this engineering degree from some prestigious schools and I had a co-op, I had an internship with AT&T and he was like, oh, Jeff is set.

Jeffrey Henderson:
So he didn’t say a word. He just let me be yada, yada yada. And so I graduated with a degree in engineering with three years of internships with AT&T. And at that time AT&T was one of the biggest design engineering companies in the U.S. And I did not pursue going to AT&T. I took a job doing blueprints in Beaverton, Oregon, and my father didn’t say a word. He didn’t say a word. The only reason I know, I mean, I know he didn’t say a word, but maybe three and a half- four years later, my parents come out to Oregon. I think by that time we had maybe had like a first kid Draymond was like a year old and they’re watching Draymond. So I come home after work and my father had come to, I don’t know if you know anything about that campus, but the Michael Jordan building is, that it’s not center of campus, but it’s middle of campus.

Jeffrey Henderson:
And right next to it is this track under the trees and there’s basketball courts right next door. And so my father ran track for university of Michigan. So I was like, you can go work out and on the track, just pull up the car and tell the guard you’re there. And no one will care. And so I guess he did that. And then when I get home, after that day, my mother’s laughing and I was like, what’s so funny. It’s your father finally gets it. And I was like, what do you mean? He gets it now? He had never said anything to me. He never complained about me working at Nike, nothing. I would sit there and shoot.

Maurice Cherry:
that’s probably why he wasn’t complaining.

Jeffrey Henderson:
I mean, he, I kind of saw it, but again, he was like, my son has an engineering degree, took his first job blueprints at Nike. And then he got a job drawing, kids, shoes at Nike, and now he’s doing basketball shoes in that, he just, it just seemed add up in his mind of what engineering degree and get like a real job in his mind, which was, being from Ohio, you can go work at a car company and do like, what are you doing out here in the Pacific Northwest? And I guess he started talking to other runners who on the track and my father was a runner and I didn’t care anything for that. So he was bonding with the people on the truck. Oh yeah. My son works over in design, like over, like in that building. Now we all know at this point, like designers at Nike are treated like they can walk on water. So when he started saying, my son works over in design, two things happened.

Jeffrey Henderson:
One, I was one of four, I don’t know, black designers in Nike, all men. So they either knew who I was or they were just Ooh, your sons at the time. And so they started talking to him and he started realizing, oh, maybe this is a thing. And so he started asking him what they do. And they were riding up, rattling off things like I just signed a deal for the NBA or I did this and all that, big that he actually understood. And at that point, that’s when he was like, oh, now because my father and I didn’t have the tightest relationships, he never said anything to me for or against. But from that point on, I knew that at least he knew that this wasn’t a mistake that I had made. He knew that like, oh, this was something that was real. So then he wore the shoes with a little more pride. Meanwhile, my brothers are walking around like, oh yeah, that’s yours. My brother designer. It didn’t matter what shoe it was. My brother did that. You know, my brother, my brother, he did everything pretty much. He did that.

Maurice Cherry:
Tell me what it was like living in Atlanta when you went to Georgia tech, because you went, you lived in Atlanta during, I think it’s peak Atlanta. It is Freaknik. It’s the Olympics and I think also the burgeoning hip hop scene there with so-so Def and stuff. What was it like being in Atlanta during that time?

Jeffrey Henderson:
So I as the biggest nerd who didn’t care, just [crosstalk 00:42:56] . I’m merely to go, I’m coming down here. I’m going to find a wife. It’s chocolate city. We’re all good hanging out. And I hung out hard for three years. As the biggest nerd, not even cool whatsoever. And it was everything you just named. It was pre Olympics. Everybody was gassed up. It was… What is it? My buddy’s roommate was a bouncer at the gold club and magic city. So we would just go sit at the bar with no money, just try and pretend like we fit in like, knowing we had zero money and we just sit at the bar and order water.

Maurice Cherry:
That can still happen today in Atlanta.

Jeffrey Henderson:
And we go in cause I get bored or whatever, and it’s like nothing but rich folk in here and its like, wow, and we would just leave after like 10 minutes. We were just like, making sure everything was good. But that was the level of everybody was sort of chilling. And yeah, we went back to Atlanta maybe three years after like, yes, not the same, my boys, were still living in like, it’s different now, but it was one of those. We were also in college. There’s nothing that will compare like as an adult to those three years when we were in college with no real responsibilities, other than staying alive and making sure you took some classes. Between going to school in Atlanta and moving to Tokyo was an ex-pat life is good. But those were big time.

Maurice Cherry:
I feel you, man. Last week, actually this past weekend, I was talking to my best friend from college. So I went to Morehouse here. He and I were just talking cause his 40th birthday was last week. And my 40th birthday was a couple of months ago. And we were reminiscing on the past. We were looking at old pictures from back then and stuff. It was wild. So I was in the AUC, right near the turn of the century. I came in 99, 99 going into 2000 and stuff. And I worked for this website. I worked for this website called College Club. That was sort of a precursor to Facebook and I was one of the campus representatives. So what that entailed was that you went around and you basically captured campus life. We had these big Sony Marika, digital cameras that you had to put a three and a quarter inch floppy disc into and take pictures and stuff.

Maurice Cherry:
So we were just looking at old pictures and stuff like that from the past, like, man, it’s such a trip how Atlanta has changed since then, because yeah, when you’re here in college, I mean, and I don’t know if it was like this at Georgia tech, but certainly at Morehouse in the AUC, the clubs would send charter buses to the campus to pick you up, take you to the club, you go and do whatever you want at the club and they’ll bring you right back to campus. So you, ain’t got to worry about trying to catch Marta, trying to catch a cab or trying to bum a ride from, from somebody to get back.

Jeffrey Henderson:
And that’s come down during [inaudible 00:45:49] and they’d be like, oh, this is amazing. And I was like, no, this is terrible. Everybody’s life is traffic jam. And it’s all these people from everywhere, hanging out and it’s like, yo, I can go on a random Tuesday to Fitz Plaza and it’d be bought out like, we’re good. And it’s just the mall, like it’s just the mall.

Maurice Cherry:
So I missed that Atlanta.

Jeffrey Henderson:
I mean, I can’t tell you whether it’s changed. All I know is I’m old now

Maurice Cherry:
Oh, it’s changed. It’s changed ain’t that shame. So, I mean, there, there might still be that same liveness depending on what the event is, and this is probably pre pandemic, but now we’re probably in the gunshots. There’ll probably be some kind of violence that breaks out. So it’s yeah, it’s definitely not the same.

Jeffrey Henderson:
Harlem is tying to trying to figure out where it’s going to be in that level. Which again, when I moved here it was like, oh, I’m not sure. We’ll figure it out. Yada, yada, yada. What I really loved about being in Atlanta and I think it was a combination of the immigrant culture that was there that I didn’t know was going to be there. The Atlanta population that was like, it was Atlanta. And then it was the rest of Georgia. And if you don’t know, if you just moved it, you don’t know the immigrant population, I lived off of Buford highway.

Maurice Cherry:
Oh wow. Okay. Okay. All right. Yeah.

Jeffrey Henderson:
The food was amazing. And so, that had sort of, like, if you don’t know Atlanta, those things don’t mean anything to you. Harlem is kind of the same way. And so being able to pick up those pieces of going from oh yeah, I miss it. And I didn’t really realize it until I got to Harlem and started walking around. I was like, yo, this feels like swats. I feel like there’s a mall here that’s Greenberg. I feel like there’s something here and I think that goes to the creative conversations that I’m having unapologetically. It’s kind of black folk. And then I encourage what designers, Sarah she’s from Columbia. And I’m like, yo, bring Columbia to the projects that we work on, please just bring them all in there. I want to see that. I want to feel like your home is there because folks kind of want that from a creative vision at this point. And if they don’t, I don’t know what to do with them. Like maybe they’re my clients.

Maurice Cherry:
Yeah. So what I’m hearing is correct me if I’m wrong here, because I’m coming up to a question with this, but you grew up in Dayton, you went to Purdue, which is right across the way in Indiana and you come down to Atlanta and then after that, you’re sort of in Tokyo, what were you searching for during that time

Jeffrey Henderson:
Being in Tokyo or?

Maurice Cherry:
Talking about like the entire journey? Was there a feeling that you were chasing or what was your drive throughout that period of time?

Jeffrey Henderson:
It’s this unadulterated push for something different, something new. There was a Twitter post a while ago with like when somebody go invent some new animals. Cause I want some new meats. I’m tired of eating the same meats and I’m kind of like that guy of growing up. Like I always wanted the new music, but I thought everybody else did. And then as I got older, I still wanted the new music. I wanted the new shoe. And it’s like, this is definitely like a knee of all things. Like I see somebody wearing a pair of shoes that I have. I’m like, yep. I got to put those shoes away. Everybody’s on this Jordan one thing. And I’m like, oh, I just put those away. I can’t walk out the house and it’s not because I’m a sneaker dude is because I just feel a certain way.

Jeffrey Henderson:
So going to Purdue, middle of nowhere, west Lafayette, they had what I thought I wanted, but it was also something different. Tokyo was like, yo, this is the wildest place on earth in terms of the visuals and the culture and the class and the people, language, everything was like, yo, I want to do this. And then I got done doing. I was like, yeah, we’re good. Let’s go to the next place. It just became this constant hunt for something new, which I still kind of have. But I think as I’ve gotten older, the combination of new plus know, I just like home, I like walking out the house, totally feeling like I’m at home and think all those other times it was me going what’s the next thing? When I got to Nike, the first thing I said was, I think this was a conversation with tinker.

Jeffrey Henderson:
And he was like, what do you want to do? And my first words were not basketball. Cause I grew up playing basketball. I knew basketball. It was just a second social life for me. And I was like, I want to do soccer. I want to do something I have no business doing so I can be in a whole nother world to see something totally new and meet new people or sweat up or the kids, the first place they told me the basketball, but even then I was trying to do something that I don’t know. I drove everybody crazy because I was trying to do something different. And I think what’s interesting is that question also pretty much pegs was my creative kind of processes was like. It was interesting cause Nike figured that out before I did. And so to fast-forward through all the headaches of my first five, six years at Nike, before I got to Japan was what they taught me was that if you put me in a functioning business where everything is great design is great and everything’s working, I will jack it up basically.

Jeffrey Henderson:
Cause I asked all the questions, why are we doing this? Why aren’t we doing it? What else could we be doing? Almost getting just to the point of start over. And so they figured out, yo, let’s go to places we know should be big, that need changing. But the people there aren’t ready to change it. So basically I became one of the people that Nike would throw into a situation that needed to be changed, but they didn’t know how to get the people in the business changing. And so I always say my first conversation of solving any problem is why? Why are we here? What are we supposed to be doing? What problem are we trying to solve? If we don’t get to the original why then we’re just putting band-aids on things. Just cover it out and go about, let it go to the next day.

Jeffrey Henderson:
And so I have this underlying question knowing at me like, yo, it could be better. It could be like better, better. It could be really better. So let’s get to the wire matter. And so I think going to new places, whether it was going to Purdue or going to Georgia tech or going to Beaverton or going to Tokyo or coming to New York City, it was always like, yo, I want to get to something new with something different. Then eventually it came to like, I’m ready to chill now. I get me. And so how can I provide opportunities for my young team? And I tell them all the time, I don’t want you here. I want you to go to your Japan. I want you to go to your mind. I want you to go to your, whatever that might be. And then you can come back if this is the right place, but go see the world. Cause it’ll make you stronger and give you new points of view that you won’t get if you just stay home.

Maurice Cherry:
What’s something about footwear or just footwear design that the average consumer doesn’t understand?

Jeffrey Henderson:
It’s funny. We just had a conversation about why I do shoes and it’s always this funny business thing is that I [inaudible 00:52:46] . I will measure people from the ground up. They’d be like, what shoes you got on? And it’s not always the measurement that people think, oh, you have expensive. Like, no, no, I can kind of take you. My stereotype is nothing based on anything else you have other than look, I see what shoes you have on right now and how you’re wearing them. And I’m going to make some calls about you whether I’m right or wrong. And I think that is probably been one of the best articles I always point to for people is Tressie, McMillan, cat, and room for Zuora. I can’t remember the exact title. Cause every time I look it up, I get lost.

Jeffrey Henderson:
It’s the reason poor people can’t afford to dress poor. And it talks about how the world expects you to, if you go into apply for a job that’s like at Walmart that pays nothing. If you’re black, you have to dress better than the job. You have to show up with something that you just have to otherwise, you’re not really right. That’s something that other folks don’t have to worry about. And I think to some degree that’s been sort of ingrained into my thinking, stems from Dayton, Ohio, like, this is kind of what I see. And I think working on shoes, whether it was one of the things we approached it easy with, it was like, it should be like the most democratic shoe that anybody can wear with colors that don’t distract or compliment or fight or cause fear. And then the project like I’m doing now like…

Jeffrey Henderson:
I don’t cause fear. The project I’m doing now, for personal, 99 products, it’s a basic running shoe that is meant for anybody to pull it off. Whether you’re a teacher, either student, or head of the class, in the back of the class, it’s for everybody. I think that sort of thinking goes into product that most people write off or they don’t even think about, they just go, “oh, I’ll just buy whatever shoe and I’ll wear it.” Maybe 15 years ago, you could have said that about most of America with cars; that their car really represented what they were doing or where they would going. They put a lot of effort and energy into the point where people stopped caring about cars so much.

Jeffrey Henderson:
It’d be like, “oh, I’ll just get a used car.” That still says something, it means something that people would put a lot of energy into cars. Today, people still put a lot of energy into the shoes they wear, even when they play them down.”Oh, you know, this is just like throwaway shit.” I laugh because people say, oh, I don’t really care what kind of shoes I wear.” I was like, “okay, then why don’t you wear some bright red clown shoes?” And they go, “well, that’s stupid.” I go, “oh, so you do care.” You do have a uniform. You do have an opinion of what you wear, so it’s not that you don’t care.

Jeffrey Henderson:
It’s just that you don’t care to keep up with the people who you think care too much about Smith. So I think in the design process, it’s sort of identifying what people want for function, want to say about themselves and how it fits into their overall wardrobe. Shoes is something else, that you may wear a different shirt every day in a different pair of pants every day. But you might wear the same shoes every day. That’s going to say something about you, like your haircut. It’s going to say something about you and you choose to be there. When you’re designing for people, you kind of have to want to be on their person, like every day, because that’s what they might use it for.

Maurice Cherry:
So earlier you were talking about how you were working for Nike and you were sending home shoes to your dad, shoes to your brothers, how your brothers were saying, “oh yeah, my brother designed this shoe.” All these different kinds of shoes. Can you name some of the shoes you have designed? Some of the more well-known footwear designs that you’ve done?

Jeffrey Henderson:
The big ones are probably the Yeezy three 50 V2, to go on the Grand Max Plus 2009, those are probably the bigger ones. Then there’s 1,000,000,001 other shoes that made it or didn’t make it. The shoes that I’ve made that sold 10 times more that were like the shoes called the Nike Basketball Air Glide. Not to be confused with the Zoom Glide that came out 15 years later, but the basketball Glide was a $55 white leather basketball shoe that sold for three years more than anybody could count, just because it was at a price point. It’s interesting, I think less about those shoes. People always go, “you’re missing the lead, like talk about those shoes.”

Jeffrey Henderson:
And it’s more like, “nah,” I’m more. And maybe it’s because I’m old, I’m more interested in the people who I’ve helped become designers for them about their path and remembering when they didn’t know any better, just like I didn’t know any better and Ray Butts and Andre Doxy.”You need to work on this, and you need to work on that.” They took me under their wing and made sure I did the right thing. That’s my biggest high, I probably did that for my mother, but it’s more about the folks who I could teach and seeing what they do with it. And also them calling me back, I remember when somebody at Denver was like, “yo, I used to be mad at you when you told me to do things and now I’ve got an intern and I’m like, yo, I’m so sorry.”

Jeffrey Henderson:
It just comes full circle at some point.

Maurice Cherry:
So after Nike, you went to Cole Haan for a couple of years, but you said Nike had bought Cole Haan, correct?

Jeffrey Henderson:
Nike bought Cole Haan in 88 and then they sold Cole Haan in 2013.

Maurice Cherry:
Okay. Was it a big shift design-wise going from athletic footwear to a wider range of footwear that Cole Haan would offer?

Jeffrey Henderson:
I wanted it to be. It’s crazy because I went from Japan to Nike running, which was probably the biggest leap I made in terms of learning skill set of being in design and design leadership. Then I did sportswear for not even a year before, we just need to get out of Oregon and go to New York city and with Cole Haan. I was so excited to get the Cole Haan and learn more about dress shoes, and how the last word and how you all the technical benefits and leathers. And like that was like, it was a whole thing. I was going through women’s dress shoes. Like this is again me chasing something like new and different, like, so one day and probably a week in Mark Parker shows up and I had just probably no more than like a month before that we had presented like a line that kind of for at least five years changed, like the direction Nike sportswear that was received really well.

Jeffrey Henderson:
We got high fives, lots of praise, yada, yada, yada. And he was in that meeting. It was like, this is really good. So about two weeks of me being at Cole Haan and I was just visiting for like a month, I was like, yo, I’m going to learn all this figure out what’s going on. It’s going to be good. Parker shows up. And he comes into like, I had this makeshift office and I had like all these pictures plastered on the wall of like Tom Ford and Gucci and churches, like wind tips. And I was trying to learn like dress shoes. And he was like, what’s this? And I’m like, yo, I’m trying to learn like dress shoes. This is new to me. Like I’m excited. He was like, yeah, yeah, that’s cool. Why don’t you do what you did in sportswear? And I looked at him like, okay.

Jeffrey Henderson:
And I knew exactly what he meant. He was like, I need you to do something different that like learn dress shoes. And he meant I should learn dress shoes. And he was also like, don’t show up and give me a wing to show up and give me something different. And so immediately we did the lunar ran light in kind of an hour because it was a marketing guy and a engineering guy were like, “yo, what if we did this? And I was like, yeah, we, I did loner for like three years in running and sportswear. Like we can do this in 10 minutes.

Jeffrey Henderson:
And so me learning everything about dress shoes and fashion, in the three years, it was all good, but it was literally like let’s do something to their credit. Everybody was right, because it became the hallmark shoe, it was the coolest shoe for all of three months. And then it just became every IT, lawyer, everybody who wanted to wear a sneaker group had to wear a dress. You wear that shoe to this day. Right. It’s still like, oh no, it’s not the coolest shoe in the world. But it’s definitely something that I don’t know. Every insurance guy has a pair.

Maurice Cherry:
How have you seen footwear design change over your career?

Jeffrey Henderson:
What’s been both. Probably. It’s kind of annoying to like some overhead to solve for where design is. One way, you go to this design school, you learned these rules, you make something and you draw it, you go into the factory and you build it. Now, to me, it’s really encouraging to watch folks who basically just Photoshop some colors together and throw some shoes together. And like it equates to, they may take the Jordan One and flip it in colors. That’s new. And the purist will be like, well, that’s not design it. Just the color. And I’m like, yeah, but at the end of the day, if somebody puts it on and gets value out of it and they feel a certain way, I think that’s valuable. Even if the shoe was already designed and someone added their own touch to it.

Jeffrey Henderson:
So I don’t necessarily think negatively about it. I do know that if you want somebody to make a new shoe, you probably should pay someone who knows how to make new shoes. But also I’ve seen plenty of designers and it was true at Nike people who would draw the most amazing shoe. And then they were colors that were terrible, like completely unwearable. And you’d be like, “yeah, yeah. Just, just send that over to my guy over here, let her do it. Let, let her put some materials on it.” You did your job, you made an amazingly functional, beautiful, physical thing. Now let somebody else add the color and whatever else that makes it wearable. And that’s a whole other job. That’s a whole other skillset that just because you drew a shoe, doesn’t mean you’ve actually had that skillset. So I think seeing that become a more regular part of the industry of people being elevated, I think is very worthwhile.

Maurice Cherry:
Now you’ve done work with Allbirds before and there’s a lot of these kinds of, I thought they came about in the last few years, a lot of these minimalists kind of shoe designs, there’s Allbirds, Greats, Vesey. There’s probably a dozen or so of them. What do you think about those kinds of shoe companies?

Jeffrey Henderson:
I love the energy they bring in, my work with Allbirds is literally, they kind of thought they might want to do something. So they hired me for one small project and I was like, you guys will be big. Can I hang out with you on it? They said “We don’t want that much. We don’t want that bigger relationship.”

Maurice Cherry:
Oh wow! Okay.

Jeffrey Henderson:
I don’t need to do that. Well, and it was one of those to their credit. I think they focused on doing something that no one in the industry thought was the right thing to do. If you ask everybody in the industry, “Hey, would you make a wool shoe?” The first thing I got is it gets dirty. It gets like, don’t do that. Dave leaned in heavy and the way they did it through DTC through a community built on starting with Silicon valley and working his way to wall street.

Jeffrey Henderson:
I think they chose a community that traditional sneaker folks didn’t have an idea about. I think to the credit of a lot of those companies, a lot of them have been people who follow in those footsteps, no pun intended to do the same thing as with like, I loved like what great submission was like, just to bring something that was quality and simple. I think they may have lost track of that along the way. I think you do, you try to run with the sneakerheads, like you get lost in like the energy and the same and the cool kid and they stock X and all the other stuff, instead of just like, it’s a business, make a dish that people want. And I think there’s credit in doing that without having to follow.

Jeffrey Henderson:
I think a lot of the brands that are making stuff now, I kind of liked them. They also give people the benefit of they can walk out their house without having the same shoe. If you walk up, do you want me to house with a pair of SES on and no, one’s going to be like, oh, y’all got the same shoe. And if you do, there’s a bonding moment. But if you tried to bond with everybody who had on a pair of air max, you wouldn’t go that far.

Maurice Cherry:
Okay. I can see that. I think one thing with those sorts of shoes, I don’t know if they are sitting in warehouses or if they’re made to order. But of course, I think with the rise of these are certainly an increased public perception of easy to obtain footwear that wouldn’t necessarily be through Adidas or Nike or something like that.I’ve seen shoes on Instagram that were clearly just, I don’t know if it’s a drop shipping sort of thing, but you’ll see some shoes on Instagram. They clearly are just parts glued onto a sock that they’re selling as a shoe. And you think, “oh, this might be good in these sort of still shots,” but then you actually get the shoes and they smell like industrial strength adhesive and you have to air out your apartment that may have happened to me. I’m not saying it did or didn’t, but [crosstalk 01:05:30] that may or may not have happened. I plead the fifth, it’s my show. But, I think what it does is that at least democratizes the aspect of footwear design, where you have these independent companies designing shoes that are also able to appeal to people that are different from before, the bigger brands that are well-known for designing shoes, like a Nike or Adidas.

Jeffrey Henderson:
And it forces the bigger brands to innovate when they really may not have had the catalyst to do so. I would equate what Allbirds did for sneakers is exactly what Tesla did for electric vehicles. Toilet had been sitting on electric vehicles forever and they weren’t trying to make it the cool kid car. It was just an electric vehicle. We make it so what, and Tesla was like, no, we make the electric vehicle. And I think there’s going to be the evolution of anything else, you’re going to find some companies that make something that’s not all that great. And hey, if you’re going to go out there and try everything, you got to be willing to be like, if you’re the one who’s not going on the open, you’re trying every restaurant. Sometimes you go fast in here, your food, but if you’re the person who wants to be that person, who’s like, yeah. Before anybody else sees it, I’m going to try it. You may stumble upon the next thing. I’m curious, what are you wearing? What is your go-to shoe at this point?

Maurice Cherry:
My oh Jesus, oh boy. It does get personal because I hate shoe shopping. I absolutely hate it. It is up there with going to the dentist. It’s shopping for shoes. I do not like it. [crosstalk 01:07:06] I have sort of wide Flintstone, ish feet. And so as a kid, going with my mom to the store to get shoes was always a hassle because one of my feet is decidedly about a half size, bigger than the other one. And also because my feet are wide, most shoes that come in like a medium are way too small for me. Like I can’t even get my foot in it. So I’d have to get a larger size because that would then kind of widen the width of the shoe a bit. But then now I’ve got all this like floppy toe room at the end. And my mom’s like, just put a sock in it, like just stuff a sock in it.

Maurice Cherry:
So it doesn’t get the crease or whatever. But then that [crosstalk 01:07:50] hurts while you’re walking and you’re trying to run. It’s a, it’s a whole thing. So I’m not a big, [crosstalk 01:07:56] I’m not a, I’m not a big shoe shopping person. It wasn’t until I know that was well into adulthood that I saw a podiatrist and actually got like my feet measured and all this sort of stuff. And I had been wearing the wrong size for well over a decade, wrong size shoe. [crosstalk 01:08:13].

Maurice Cherry:
I wear about a size 10 extra, extra, extra, extra wide, like a 10 40. And usually what I was getting was, and I mean, you know, growing up, of course it would change as my foot change. But like right now I usually rock about an 11 is pretty good. But like if one was an 11 and the other was an 11 and a half, that would be perfect because even on the other foot, which is bigger, it’s still like very constricting and most wide shoes are hideous. You’re a footwear designer. Even talking about this, the desire for like medium shoes. I mean, the sky is the limit. You get to watch shoes and everything looks like orthopedic shoes. Why is that?

Jeffrey Henderson:
So there’s a little bit of like the bell curve. And so quite typically the design goes to, and you’ll notice that most things, when they’re in a smaller size, they can be more cute, more appealing. And so,

Maurice Cherry:
Yeah, they’re dope. Like I can, like, you can get them in different colors and they look nice and then you get to the wide shoes. And it’s just like, it’s like what I call the PE teachers, which are the monarchs from Nike. Like that’s all you get. [crosstalk 01:09:27] I know, I know that’s probably,

Jeffrey Henderson:
That’d be the cool kid shoe.

Jeffrey Henderson:
But a lot of it is definitely built on again. If you’re making your money in one area, a lot of brands don’t then spend a lot of time in other areas. And so you get some brands who may find that’s a niche customer. So my guess is you bought more than your fair share of New Balance.

Maurice Cherry:
Oh my God. Yes. How did you know you’re reading my mind? Yes. There was a time in my twenties where I had not a lot of different colorways of New Balance, but the new balance, not the nine nineties, those were ones I ended up getting before. But like the, I forget the number. It’s like new balance five somethings. I had those in probably every color.

Jeffrey Henderson:
And it kind of becomes your uniform and it’s time to, okay. But then when is that? What ends up happening? Two things happen. Everybody who has that same point is wearing the same thing. And then you get lumped in a box.

Maurice Cherry:
Yes.

Jeffrey Henderson:
And then it’s one of those, oh, you have wide feet. So you have to wear new balance and then there’s not enough, let’s do something different. [crosstalk 01:10:37] And so you have to refine the brands that sort of, I don’t know, care, or we’ll show you something different and it’s not easy.

Maurice Cherry:
Yeah. It’s the new balance Five, seven fours. I had them in so many different color ways. Cause they, I mean, and on 11 they still fit. They still were pretty wide, but I had those for a long time and yeah, there was that association, which is actually why I stopped wearing them. Well, that in my podiatrist was like, you need to stop wearing these. They’re not doing any favors, like stop wear these shoes. Yeah.

Jeffrey Henderson:
So it was funny as it was a podcast or was a clubhouse and my friend Simone runs it and she had the president of Rihanna’s brand owner [crosstalk 01:11:18] and hear her talk about inclusivity and design that what Rihanna wanted. She was like, look, there were two things that quickly and easily made, making intimate wear for a diverse population of women. Important one was really easy. And that was just shades of nude. Like just what colors you chose. She was like, that was really easy. Every brain could flip that switch immediately and go from like two shades of nude to 20 shades of nude because there are different colors of people. And she was like, that was actually, it’s more of like a decision you have to make. And then it’s a supply chain thing and some operational, the blah, blah, blah. It’s pretty easy. The really difficult one is when it comes to physical shape and sizing, because one, you have to have people in the building who can relate and understand.

Jeffrey Henderson:
She was like, not everybody in intimates is the same size 16. Sometimes you’re 16 up top. Sometimes you’re 16 on bottom. Like it’s just different shapes. And if you can’t have a real conversation about it, cause the right diversity is in the room is not in the room. Then you just end up making, like, we just took the same thing and made it bigger. And then you don’t write answers and then you get what she put it. You’ve been with skinny people think that people want, and she was like, it’s not that blunt, but you also get what skinny people think super skinny people want. And she used those words. She was sort of getting like, yo, like it just doesn’t help. And they don’t know. So until you bring people in the room who have wider feet or like our last version of the, and that was one of the things Rihanna said is like, no, when you make the larger sizes, it better be just as beautiful when a person is when you make the medium size.

Jeffrey Henderson:
Like that’s just what it should, what should be done. And so when we were making the next versions of the point, I had a lot of flat, cause I know a few football players who were like a size 15 and I shoe only went up to a 14 and it was like, Jeff, Jeff, Jeff. Yeah. Like what are you doing this next batch? And it costs money. Like we had to make molds, we’ve gone up to a size 17 with these things shoes and we’ll try to go up more, but like it costs money to get there and you need people to actually support like, so I sent you a link, you’ll see it, the jokes, John. But that shoe comes in like four E in terms of width [crosstalk 01:13:34] so there, and you’ll try more and it’ll be different. And whether is your cup of tea or not? The idea is that when you wear them, you’ll notice some wind here and you’ll see like, oh, it doesn’t have to look hideous. It doesn’t have to look [inaudible 01:13:50] And it’s kind of, okay. So I think design can bring that to people, especially in shoes.

Maurice Cherry:
Yeah, So, so to answer your earlier question about what I’m rocking. So I do have kind of my two that I tend to sort of vary between one is like a, all black, like Reebok walking shoe. I don’t know what the name of it is, but it has like this air bubble in the sole. So like it’s very bouncing. Like I wanted some just like straight up like black minimalists sneakers that I could just throw on with anything. And then I do have a pair of monarchs and I actually had to stop wearing because the cushioning was too much. Like it was like, my foot was in like a spaceship and it’s funny. Cause I remember when I first got those shoes, I would get so many compliments on them and I’m like, thanks. And I didn’t know if it was for real, cause I honestly got them because they came in a wide with my podiatrist’s had recommended it.

Maurice Cherry:
And when I first put it on, I was like, oh, so this is what it feels like to walk without foot pain. Like now the shoe actually like, but I still have that one for every now and then, but I just bought three pairs of shoes recently.

Maurice Cherry:
I don’t know if this is because I got the vaccine and I feel like I need to go out in the world, but I got three new pairs of shoes recently and they’re different in different ways. So one is a Fila shoe.

Jeffrey Henderson:
Okay.

Maurice Cherry:
It’s the Oakmont mid and my, my podiatrist, I recommended it cause it had a thick sole and he’s like, you kind of need more of like a, almost like a boot type of shoe as opposed to maybe like a low sneaker type or something. And so I have those and those are great. Those are ass-kicking shoes. Like I love those shoes. And then I got a pair of Hoka, Bondi seven. I just got those a couple of days ago actually. And I might send them back. They’re too bouncy. They feel like I’m wearing moons shoes. Like if I needed to jump and reach high things, I would probably keep them. But like I’m walking and I’m like, whoa, like I’m literally, like I literally have a spring in my step is what it feels like

Jeffrey Henderson:
It’s meant to be. It’s meant to do that. So it’s good in terms of the functionality. It’s not the functionality you’re looking for.

Maurice Cherry:
Yeah. And then I got another like honestly I got a card in the mail from DSW that was like $25 off a shoe. I’m like, let me just get some more like knock around shoes. And I got some Sketchers, like slip ons there, the ultra flex 2.0 Mercon slip on sneaker and they’re okay. But like one of the shoes fits and the other one is too small because it’s not wide enough for the other foot so I can still wear them. But they’re just like, they’re okay. And I mean, after the discount, they were like 25 bucks. So I’m like, yeah, this is, this is just something I can just throw on and like check the mail or something like that.

Jeffrey Henderson:
So we’re going to get you into some Johns. You’re going be to, you know, say nothing but good things. We gonna see you on the gram And then you had to give all praise if you like it. And if you don’t, you never heard of it. So its all good.

Maurice Cherry:
Ill Put a link to this in the show notes so people can see it. Like I’m looking at it now, the Jackson YC, John, they come in like this lemon ice, yellow, like ch like classroom, chalk yellow, which is an interesting color way. I like it.

Jeffrey Henderson:
They also come in gray suede, I think there’s a gray suede

Maurice Cherry:
Oh yeah, I see I’m scrolling down. I see now

Jeffrey Henderson:
Scroll down.

Maurice Cherry:
The yellow was interesting though!

Jeffrey Henderson:
And that was based on, so my brother, his kidneys started failing his feet, started swelling and he needed wider shoes. And so I put them in some Birkenstocks, which he was good with, but he needed like some actual real shoes to get around in. Cause he’s in Ohio and it was winter. And so I was working with his brand in China and they made the shoe for seniors. The name of the brand is Zulee’s and so, and the shoe was like, I don’t know, it’s kind of the way they created. It was very much like old people shoes.` It’s like, it just had this diet to this sort of function first and it just didn’t look cool. And I was like, yo, can we make these in first suede? And then can we make them in like some monotone colors that I don’t know, you think you like, look good?

Jeffrey Henderson:
And they were like, well, that’s not what old people want. I was like, well, how do you know? Like, and they were like, all right. So they blessed us with some pairs just to try out. [crosstalk 01:18:04] And people were like, yo, I can look good. Like, and we kept getting hit with, I don’t want to wear them out. And it was like,

Maurice Cherry:
oh, interesting.

Jeffrey Henderson:
Because they were all suede. And they were like, I don’t want to get them dirty. Cause they look so nice. It was like, like stop wearing the shoes that you hate because you can get them dirty and wear these. And it was interesting because we made our conservative desks that, you know, we’ll make them in gray and we’ll make them in yellow thinking that, you know what? People will want the gray because that’s normal. But you know, we’ll get some daring people to wear the yellow and it kept going back. Like I think we sold out of the yellows in most sizes. So you have your side, it’ll be lucky. But for the most part we have grays left cause people wanted like they wanted to stand out in the way that wasn’t like clown, but also they didn’t want to look like I am the old person I am. And I think that, again, it goes to, wasn’t so much about the design, the design should work, but sometimes it’s color and materials [crosstalk 01:19:00] that kind of plays into how people feel.

Maurice Cherry:
It is an appropriate amount of swag. Like I’m looking at the photos, like there’s this one where this dude is getting into like a rag top convertible and like his, the color of the car and his shoes are pretty much the same. I’m like, that’s kind of dope. And he’s cause he’s wearing a black jacket. It has on yellow shoes. And then you see like the black rag top in the yellow paint, like okay. Bet. All right, cool. Well, we will definitely talk about that after we stop recording. Cause I would definitely be in the market for these look, these look great. And it’s interesting that there’s this personal story behind the design too. What I get, you know, from just talking with you and learning about your history and everything is that eventually you always bring it back to the work, which I think is something that is indicative of people that really have a passion behind what it is that they do.

Maurice Cherry:
Like even with the name of your studio being “And Them” like you’re taking the onus and the focus like off of you, it’s really about how the work is being received in the world and how people are using it. Which I think is super, not just, I think super important, but also super inspirational for people to see, because I think especially for younger designers there.

Maurice Cherry:
can be this, want to kind of do the biggest flashiest stuff all the time. Or like, like that’s the stuff that they want to do that they feel like may point out the thing in their career or like put them on the map or something like that. And really if the work that you’re able to do is like really changing people’s lives and affected them. That’s hopefully just as, as good as a takeaway from the work that you do.

Jeffrey Henderson:
No, I think that’s well said. I think even the work that you’re doing, like you talked about, like it took you a number of podcasts and a number of like folks in the outside, like co-sign for credibility to be there with other people. But the reality is you are going to do it because you thought it needed to be there. And I think that’s very important. So people don’t understand that sometimes people won’t come out to you first show people won’t come out and see like the first game you play in cars may not be great. But if you know why you’re there and you keep working on your craft, you get better.

Jeffrey Henderson:
And that’d be great, but if you know why you’re there and you keep working on your craft and you get better, I think it then pays off, and it doesn’t always have to be, “Did I have the biggest show on the planet?” Sometimes it’s just about, “Did I do really good work and were people happy?”

Jeffrey Henderson:
So, no, it’s definitely whenever we can use our skills to make friends and family happier, and when they bring us new friends and family that we can work with, we’re happy to use our skillset to make other lives better.

Jeffrey Henderson:
I don’t know that we technically announced it. I guess they announced it. We’re working with this Reinvention Lab out of Texas, this group out of Teach for America to kind of… We ran a shoe contest, and they got to actually find organizations within their group to design shoes and they got to work on it.

Jeffrey Henderson:
And what’s interesting is there’s going to be a winner, and we’re actually going to sell some of the shoes that they made. And they were like, “Oh yeah, we don’t care if we won any more.” Just going through the presentation process, how designers look at things, how they have conversations about things… Just the design process was new to them. And that helped them understand what they bring to education and what they bring to laying out curriculum, which I sort of, I don’t know, I hang out with Chris Emdin, whose HipHopEd, and the way he talks about pedagogy. Those are things that I take internally as normal, but they had to go through this class. They had to do this competition to take in and be like, “Oh, design thinking is not just for designers. It helps us.” And so that was really gratifying to see. Or even just our approach and our process could bring, I don’t know, something to other people.

Maurice Cherry:
And speaking of school, I mean, you’re on the advisory board for a school in New York, the Business of Sports School. And most recently you became a board member at Knoll. For you, what’s the importance of sitting on boards like this?

Jeffrey Henderson:
It’s… Another thing that I sort of got dragged into, and some of it’s because I’m old, I hang around old people and they are on boards and they say, “You’d be good at this.” I didn’t really know what a board did or what it meant. Now that I’m on two, I can sort of surmise that it’s definitely one of the, for most businesses, the biggest form of sponsorship you can get. Because as much as mentorship and execution are good, if the people who are sort of guiding the people who are in charge understand the entire, I think, operation and process, the better it is for the people who are doing work and the more diverse of an angle you get. And so at BOSS, this a sports school, it was…

Jeffrey Henderson:
And one of my best friends on the board, we were having this discussion around college visits. And so BOSS is a school in Hell’s Kitchen, most of the kids come from the Bronx and Harlem. In terms of who could attend, they’re changing up a little bit how who gets into the school, but it’s definitely an open enrollment. It’s not based on higher test scores and they don’t pick who they get into the school. It’s just kind of an open free-for-all in terms of kids that get to the school.

Jeffrey Henderson:
So it’s not built on kids who are automatically going to Harvard who have family history and education and college background. And so one of the things that they’ve promoted, I think for good reason, is they want to make sure that kids have an understanding of what college is, and so they go on college tours. And so the college tours were happening around junior year, and I said, “No, it’s too late.”

Jeffrey Henderson:
And my friend Marie, who works for SMY, her son at the same time… I think both of our sons were in college, were in high school and around junior year at the same time. And she chimed in and was like, “No, you have to understand. My son, this is the biggest time of his life. He’s visiting all these colleges. And it’s really important. It’s shaping who they are.” And I was like, “Yeah, but your son has heard about college since he was five years old. Some of these kids, none of their family is going or has gone to college. And so this is a new concept. They’re expecting them to go work. Some of these kids, their family is wondering why they’re finishing high school, literally wondering why they’re finishing high school, when they could go work and put food on the table. It’s a different conversation. So can we please take them freshman year, even just to one college campus? Normalize the idea of college in their brains before they’re taking an ACT, before they’re taking a prep test. Can we do that?”

Jeffrey Henderson:
And what’s funny is she saw that, and she was like, “Oh.” And because this was happening at the board level, this is well before the teachers had to choose where they were spending money or where they were scheduling time, and so offering a more diversity of voice, at a school like that, I think was powerful. But there’s quite a bit of diversity on that board. When I got to Knoll, there wasn’t that much of diversity of thought on the board. And it was interesting, because when it first came up, I was like, “Are you inviting me on the board because I’m Black?” And they were like, “Well, that’s helpful.” And I was like, “Oh [crosstalk 01:26:00].

Jeffrey Henderson:
And I was like, “Well, are you inviting me on the board because I’m creative?” And they were like, “Yeah, it’s a design company, and we don’t have creative people on the board. There’s a misstep there.” And I was like, “Oh.”

Jeffrey Henderson:
And then later on, someone was like, “Yeah, scary enough. You’re also young.” I was like, “Oh, I haven’t been young in a while.” But I was the youngest person on the board. And I think, again, being able to have diverse levels of thought at a board level where it’s really only about sponsorship, it’s really about giving direction to the real leaders and responsible folks who run something, being able to give them a sounding board and holding them to task on, “Are you getting the most out of your people? And by the most, are you just even listening and can you hear their voices?”

Jeffrey Henderson:
And I think when boards start to diversify, I think… And I mean, the same is true in C-suite. I have a whole thing about, “I love all my friends who are D and I experts at every company, but you wouldn’t need them so much if the C-suite was diverse. You’d have other problems to fix because then those folks would make sure that there was a diverse hiring thing.” Maybe not all the time, but there’d be more folks to sort of like, “Let’s get after diversity in bigger ways.” And I think to me, the board level helps usher and push along those movements. So I’m very, very happy that folks sort of tapped me on the shoulder. One, I didn’t look like the average board person. I also went in saying I wasn’t going to act like the normal board person. And I think they were actually quite excited that I wouldn’t be. So I was blessed to end up in conversations that they wanted me there, as opposed to they felt like their hands were tied about having me.

Maurice Cherry:
So I mentioned before we started recording that I had done my research. I read through a lot of articles that you had written up on the GwoodThin.gs blog, and they’re also syndicated on Medium.

Jeffrey Henderson:
I apologize for [crosstalk 01:27:58].

Maurice Cherry:
No, no. I actually want to talk about that. What does writing do for you as a designer?

Jeffrey Henderson:
Writing is probably, and this plays into, I don’t know, the background of introversion of I stumble across my words. If I’m having a conversation, I’m one of those people who goes, “Oh, I wish I would have thought about that when we’re talking” because I can’t think on my feet like that. And so being able to write, a skill that my sister made sure I… She saw that I had a little bit of a talent. My sister’s 13 years older than me. So she saw I had a little talent and made sure my teachers knew and forced me to write more and more when I was in high school. And that just became a way for me to, almost in a journal way, sort of write down what my thoughts were when I knew I couldn’t finish them in other ways, or I really didn’t feel comfortable talking to other people.

Jeffrey Henderson:
And also allowed me to… And when you get old and have kids, you sort of see that, well, your kids aren’t always listening to you. And I, for sure, didn’t always listen to my parents or my elders, but if you write it down and leave it so that when they’re ready to take any of the information, it’s there for them. And so for me to write it down like this… And people bring up some of those Medium posts all the time like, “Oh, I read such and such.” I don’t even remember writing it. It’s from 2016. And I might’ve just copied and pasted it from a Tumblr post from 2012. But it’s more of my journal, this was kind of going on or a thought that popped up in my head that I may have wanted… or someone asked a question that I wanted to answer for that person, but also wanted to answer for multiple people.

Jeffrey Henderson:
So being able to write, to me… And it’s funny because people often talk like, “Oh, you write the same way you talk.” And it’s like, “Well, that should be the same way with everybody, I would think.” And so I don’t use complete sentences, and I’ll stop in the middle of a sentence and just go into the next thing because it’s really just my thought… And my kids hate it. They’ll read and be like, “You have no focus.” Because they took real writing classes and I’m like, [crosstalk 01:29:57]. “You’re smarter than me because I can send you to a school that you can be smarter than me, so leave me alone.”

Jeffrey Henderson:
But for me, it’s sort of this unfiltered way of throwing down whatever is in my head. And I might evolve six months past whatever I wrote, but my journal is sort of me documenting my thoughts so that if it’s helpful to somebody at a time, it’s good. And also there might be hope that there’s some things that I’m sort of fighting against or don’t want that one day it’ll be sort of useless because they’ll be like, “Oh, yeah, we don’t have those problems anymore. We’ve moved onto new problems.” But hopefully that becomes the case.

Maurice Cherry:
Well, I have to say I could not stop reading. I think you’re a fantastic writer. I think you should keep it up.

Jeffrey Henderson:
Thank you. No one knows that I’m paying you in shoes to say that, right? Okay. Okay.

Maurice Cherry:
Look, I was going to say that before the shoes. No, I’m kidding. I’m kidding. No seriously, though, I mean, as I read through it, I think it’s important not just as you’re talking about to push your thoughts down, but as you also said, for other people to see, and not just your kids, but for other designers to stumble upon, “This is what it’s like for an agency owner when they’re working on projects,” or, “How do you think about the work that you do in your creative process?” That kind of stuff tends to not really get shared, certainly not from other black designers in that way.

Jeffrey Henderson:
I was listening to, I think one of the interviews you had before, and I think you brought up that you could throw something in a Tweet and how deep does it go, but how long does it actually stick? It kind of gets lost in the universe.

Maurice Cherry:
Yeah.

Jeffrey Henderson:
And I think when you actually write a book, there’s a little bit more staying power. And I think those long reads that challenge you to follow a story that imparts information, I think, are very powerful. And I think there’s also just… Some people would rather have the 300-page book about a topic and some people want a TikTok version of the same thing. And I think everything’s not for everyone. So how I communicate may not be for everybody. I apologize that you had to read through all those, but for some people they enjoy reading them and some people are like, “Yeah, I read the first three lines, and I was good. Way to go.” And that’s okay. [crosstalk 01:32:05].

Maurice Cherry:
No, I read through all of them because some of them you’re talking about different projects that you’ve worked on. There was one even about the recent board appointment that you had mentioned. So it was just good to sort of see it, see how you perceive the world through your eyes and your words and how that all… Because for someone like me, I wouldn’t know what that’s like, but to read your words on it, it’s like, “Oh, so that’s what it’s like.” Just to kind of see that perspective is important.

Jeffrey Henderson:
And it’s really powerful when you don’t have enough voices in jobs from people who look like you who might be able to say things and sound like you, not only for you to hear and go, “Oh, okay. This is what it’s like when I get there.” But also I think I wrote one article about of the nicest guys I know on the planet. He posted on his Instagram a photo of the Nike design offsite. It was a picture of all the Nike designers and pretty much all white folk with… You can pick out the three or four people who aren’t white.

Maurice Cherry:
Mm-hmm (affirmative).

Jeffrey Henderson:
And when I saw that, I had anxiety just looking at the picture. Because I remember going to those offsites going like, “This is weird,” and not knowing who to tell or who to say it to except for people who were there.

Jeffrey Henderson:
And we were all kind of looking at each other like, “Yeah. But it is what it is.” Someone just posted the phrase, “It is what it is” on Twitter. And I was sort of like, “That’s a very dark expression for Black folk because it’s almost like you’re giving up, like a loss of hope.” But “it is what it is.” It’s not what I think other people might think it means. It’s definitely like, “We’re done here. There’s nothing we can do. It is what it is.”

Jeffrey Henderson:
And I think changing that at Nike became something so many of us focused on that, I don’t know… I don’t know if we were able to put a dent in it as much as we wanted to, but it definitely some days felt it is what it is.

Jeffrey Henderson:
And that picture brought out all that anxiety. And I told him. I was like, “Yo, are you okay? I’m going to actually use the article. I’m going to write your name and say what a good dude you are but also explain this is the truth.” And it’s funny how many people who reached out to me after, on both sides who were like, “Yo, I thought this and I didn’t know how to feel, and I didn’t know what to say.” Depending on, like, on each side, which is kind of interesting. And there were some people were like, “Yo, you never acted this way when you were there.” And it’s like, “Maybe I did and you didn’t notice.”

Maurice Cherry:
Yeah.

Jeffrey Henderson:
Or, “Maybe when you knew me, I was going with ‘it is what it is.’ So what’s the point in telling you about it?”

Maurice Cherry:
Yeah.

Jeffrey Henderson:
So writing is a way to sort of, I don’t know, let people see what it really was, even if you couldn’t do it in real time.

Maurice Cherry:
Mm-hmm (affirmative). I think it can also sort of serve as a mirror back to you, particularly in terms of colloquial language. You have one post on here called Who All Gone Be There, which is so common, I think, for any person of color they’re going somewhere that’s mixed company.

Jeffrey Henderson:
[crosstalk 01:35:12] talking about.

Maurice Cherry:
Yeah. You’re like, “Who all gone be there? I need to know what I’m stepping into,” or something like that. Or even there’ll be posts that are named after song titles. There’s one called Shook Ones or something like that. Or even one where you’re breaking down the cost of a shoe, you know, or the materials and everything that go into it because people will, I think, certainly with the inflated sneaker economy now, people will look at a shoe and wonder why it costs that much, but not thinking of everything that has to go into it with research and materials and all that sort of stuff.

Jeffrey Henderson:
Right. And what’s funny is, I think… And I watch what’s happened in the last 20 years with journalism is that, I don’t know, maybe 20 years ago there would be, especially sports journalists, I think that’s kind of where it started with like, “Oh, this is the hip hop journalist, and he speaks in a vernacular that connects to the people and uses hip hop slang,” and yada, yada, yada. It’s one of those. Or “Y’all just letting him write and just write what he would write to his friends.” And so for me, I think that connection point of calling it Shook Ones is not… I’m not trying to connect with you. I’m not apologizing. It’s just like, “You know where it’s from. I know where it’s from. So that’s how we communicate. That’s how communication works. I don’t know any Billy Joel songs to impart to you how I’m feeling about it, so I can’t do that. And if I could, then I would connect with… Are there Billy Joel people listening?” No shade to Billy Joel, but that’s sort of… I’m just talking the way I talk in the group chats with folk.

Maurice Cherry:
Yeah,

Jeffrey Henderson:
So it’s sort of… And I think that was… And writing helped me… I talk about this a lot. I grew up swearing like nobody’s business, and I don’t know if we cool. We know what you like. I could swear left or right. Writing helps me like, “All right, let’s change some of those words. Sometimes it bes what it bes.”

Maurice Cherry:
Yeah. And to your point, it also, you know, even, I think, as it reflected through the makeup of your team, it shows them that being able to express themselves authentically doesn’t make them any less of a professional.

Jeffrey Henderson:
You know what’s wild is… And I talk about this a lot with folks who are of my age group, who are in this weird late forties, early fifties, where we sort of went through a history of trying to code switch. And like I said, I don’t know if I’m necessarily good at it. I think I tried it enough, but I don’t know that anybody bought it. But the idea that young folks don’t care to code switch.

Maurice Cherry:
Yeah.

Jeffrey Henderson:
They just show up how they show up and talking to folks who are my age. It’s like, “Yo, don’t get caught out there code switching because the young folks would call you out on it and they ain’t listening. They don’t have time for you to be worrying about what you got a bonnet on at the airport. It’s just not [crosstalk 01:38:08].

Jeffrey Henderson:
It should just be you every day. And it’s difficult because we came from an age group where we were taught when you show up, you’re in their space. You need to respect [crosstalk 01:38:18].

Maurice Cherry:
Yeah, respectability politics.

Jeffrey Henderson:
Exactly. And it’s sort of… I was lucky enough to… And I say this all the time. I have amazing credit only because when I got my Discover Card in college, it was like, “Yo, you can either pay this much or you can pay this little bit and all these other numbers about what you pay for the next six months.” And I was like, “I’m too lazy to do that. I’m just going to pay the big number.” So I never had debt because I just paid the big number. So it’s not because I was smart and knew, “Ooh, I want to get good credit.” It was I just don’t want to deal with the headache.

Jeffrey Henderson:
Same is true about… I was just like, “I don’t want to wear a tie to work ever. I don’t want one of those jobs. I’m not going to go work there. I just want to wear sneakers to work.” I just chose that, not knowing it was going to be… I didn’t choose this because it would make me money. I didn’t choose it because it would provide me money to buy a house and not have to assimilate so much. I did it because I just liked sneakers and I liked the culture. And I think young folks are more and more for the technology to exist, they get to do the same. They’re just trying to figure out what it all means because they’re being told by older people, “Oh, it’s adulthood time. So now you have to follow in line and you’ve got to wear your hair a certain way.” And they’re like, “No, thank you. But [crosstalk 01:39:33].” So I think it’s cool that people can be who they’re going to be and old people like me get to help them do that.

Maurice Cherry:
Where do you see yourself in the next five years? What kind of work do you want to be doing?

Jeffrey Henderson:
Yo, this drives me and everyone else crazy that I want to be able to just walk down the street and not have to go anywhere and everything comes to Harlem because we made it possible. I went from, I don’t know, doing product design a few years back to ad and content creation. And now I’m missing a call right now about NFTs, which I had no idea about, but, “Okay, let’s go learn about NFTs and the process and the drops and all this other stuff.” And it’s one of those… I think the strategy mindset, the creative mindset, and a little bit of, I think, luck along the way of having some wins, folks invite us to parties, whether it’s just me or my entire team. I think people trusting my team as they get better. And the team’s starting to have their own sort of mentees below them to kind of grow the business for all of us.

Jeffrey Henderson:
And even if they go run and create their own agency, it’s all good. I kind of want this fun growth to keep, I think… I used to say making stuff was cool, and now I’m to the point where making stuff has taken a different personality, given my thoughts on sustainability. And sometimes it’s not making stuff is the answer, but figuring out how…

Jeffrey Henderson:
My biggest thing in terms of conversations in the last probably three months has been on housing justice here in New York City. And I think that’s not the standard conversation for maybe a creative, but I think the thought process and the connections and the ideation that myself and my team, the folks I hang out with and bring to the table just, I don’t know, open up the vision on some of those things. And I think that’s what I mean when I say putting things… And I’ve always said this. If you can create, I don’t know, some systemic change in Harlem and Atlanta and Oakland, in places like Detroit, I think if that starts to stick and ownership becomes a big piece of it, I think there’s some conversations that are really going to be had.

Jeffrey Henderson:
And then their less talking about, “Oh, well, I don’t know if we’ll give them a chance, but we’re good. We did this. We’re good.” And I think that’s where I’d want to be. Even if it’s not me, I’m just hanging around people who are doing those things. That’s my five years from now.

Maurice Cherry:
Well just to wrap things up here, where can our audience find out more about you and about your work online?

Jeffrey Henderson:
So definitely come hang out… For the most part, if you want to find out about all the fun we’re having, find us at GoodThin.gs, G-O-O-D-T-H-I-N.gs. I’m sure it’ll be in the bio and byline. That’s where we have our fun. That’s where we give back to the community. That’s where we show how we hang out. You want to book us for business? Definitely come to andthem.com. We keep it professional. You can write us checks and we’re all good. Ready to do stuff. And then definitely, I don’t know, we’re making some shoes. We’re doing apparel next. You can see NinetyNineProducts and Jackson YC. my guy [Royce 01:42:42] is doing Silk City. We got a few hustles going on, some fun. So please, you don’t have to read all the reading [inaudible 01:42:49] is doing. Greatly appreciate it, but you can come check out and see some of the creative stuff we’re doing.

Maurice Cherry:
It’s good reading, y’all. Don’t listen to him. It’s good reading. Jeffrey Henderson, thank you so much for coming on the show. I think, you know, from hearing your story, from looking at your work and, again, even from the research that I’ve done, to me, there is a certain deep sense of thoughtfulness that you bring to your work that perhaps I don’t know if you even recognize how thoughtful it is in terms of doing work for the community and making sure that you’re creating this nurturing space for young creatives and everything. I think it’s something that more of us need to see in the industry. We need to see, of course, I think just more Black agency owners, but also more Black agency owners that are kind of bucking the trend or changing the paradigm or showing that it’s okay to be thoughtful and do great work like this and not have to stick to, you know, any sort of archaic or a draconian style of running a business, that you can do great work and have fun and it can be a nurturing space.

Maurice Cherry:
And I definitely see that care and thoughtfulness that you bring to your work, and I’m appreciative of it. I’m sure that folks listening think that way as well. So thank you so much for coming on the show. I appreciate it.

Jeffrey Henderson:
Thank you so much. I’m glad to be on that list of hundreds of people who you bring in, I think. Visibility too. I love what you’re doing. So however I can be a part of this, I’m happy to help. Thank you.

Sponsored by Brevity & Wit

Brevity & Wit

Brevity & Wit is a strategy and design firm committed to designing a more inclusive and equitable world.

We accomplish this through graphic design, presentations and workshops around I-D-E-A: inclusion, diversity, equity, and accessibility.

If you’re curious to learn how to combine a passion for I-D-E-A with design, check us out at brevityandwit.com.

Brevity & Wit — creative excellence without the grind.