Matshoshi Matsafu

November ends with a fantastic conversation with Matshoshi Matsafu, and let me tell you…she has lived. Lived, I tell ya! She currently works as a senior UX designer at Microsoft on their Flipgrid product, but that’s only the tip of the iceberg when it comes to what she does and what she’s experienced.

Matshoshi talked about growing up in South Africa and attending college in Johannesburg, relocating to South Korea to teach for a few years, and about her most recent move to Minneapolis and how life has unfolded in the years since then. She also spoke about being a Black creative in flux (and how to embrace it), the joys of embracing being a generalist, and shared what keeps her motivated and inspired as a creative. According to Matshoshi, being a Black creative is a myriad of things. So why not explore them all?

Transcript

Full Transcript

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

Matshoshi Matsafu:
So my name is Matshoshi Kholofelo Matsafu. I am originally from South Africa. I’ve been based in the US for almost five years, six months and a couple of days. I am currently working as a Senior UX Designer for Flipgrid, which is a subsidiary of Microsoft. Essentially it is like a video exchange software where it became really popular during this pandemic because it was really useful in the education field. Yeah, I work in tech. I create digital artwork from time to time. I illustrate, and I’m into music, into a lot of things that just like equal creativity. I guess that would be the sum of me. Yeah.

Maurice Cherry:
Okay. I was going to ask you about Flipgrid because I had not heard of it before. So I’m guessing this is a company that Microsoft acquired. And you work on the team?

Matshoshi Matsafu:
Yes, yes. So it was acquired actually not too long ago. Essentially we make a really robust video editing camera and software that’s available online predominantly for students and educators now, but it’s expanding. What I love about it is that I get to work directly with real educators. We’ll get into this a little bit later, but I spend some time doing ESL teaching myself. There was always a need for tools to help students that aren’t necessarily comfortable speaking out loud in front of a classroom forever, or giving them prompts and creative ways to elicit a response. This is one of the things that I get to build on a day to day. That’s what really is exciting.

Maurice Cherry:
Yeah. I could see how something like that would be really useful, especially with so many classrooms over the past, God, two years now, geez. Like adapting because of the pandemic and things like that. But also not just schools. We’ve done some work in the past with the Smithsonian,. I know that do or they tend to have curriculum for schools like summer programs and things like that. I could see where they could even use something like that because especially in terms of curriculum, a lot of schools will look to museums and such for field trips and things like that. But when you can’t travel to the museum for a field trip, then how are you supposed to get that same I guess, cultural exchange? So I could see how Flipgrid might be super useful for something like that.

Matshoshi Matsafu:
It certainly is. I’m really glad that you went into that because looking at some of the very surprising use cases that have come about, it’s exactly that. It’s families connecting with each other when being divided because of COVID, sending each other video messages on a private secure platform. It’s teachers obviously connecting with their students. It’s book clubs and choirs and auditions for plays that are happening on this platform because it’s a way to be able to ruminate about what you want to create, but not have so much pressure to have it be completely perfect and still be able to express your creativity. So I think that’s kind of why I love it.

Maurice Cherry:
Okay. So how has 2021 overall been for you?

Matshoshi Matsafu:
I can say there’s a definite shift in terms of my feeling of not being tossed into the wild like 2020 was.

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
I think the acclimation that has happened, whether it be from a mental health perspective or from an understanding how I work and what works and what doesn’t. Like a lot of people, the introspection helped a lot. It has definitely been a year of revelation for me as to what’s important. How do I want to spend my time? What do I think is worthy of my attention and what relationships do I need to foster? How do I hold myself not so much accountable, but how do I grow in a non pressurized and from a perspective of love standpoint?

Maurice Cherry:
You’re located in Minneapolis, which last year was such a nexus point for so many things happening just in this country around police brutality and protests and things of that nature. How was it being in the city during that time?

Matshoshi Matsafu:
It was incredibly wild because little bit of history, I grew up in the dredges, like the end or not quite end of Apartheid date in South Africa. So when I saw the tanks patrolling the streets, it just drew me right back to memories of growing up in a policed state.

Maurice Cherry:
Wow.

Matshoshi Matsafu:
Where white people were trying to kill us. They were holding AK-47s. There were tanks patrolling the areas that we were essentially forced to live in. We call them townships. If you speak to a lot of South Africans, kind of like if you speak to a lot of indigenous and black people here, there’s been a a reclamation of areas that we were sent to die, essentially. By calling them townships or the hood and not actually calling them what they are, which was essentially a concentration camp.

Maurice Cherry:
Wow.

Matshoshi Matsafu:
We are a resilient people. All I remember is seeing those riots and understanding what is driving people is not about actually the incident that occurred, that was just the tipping point. This iceberg has been building. Like everywhere else in the world, I was really in turmoil about the conversations that were being had and the ones that were being avoided. There was so much focus on the masses of people, black and brown bodies showing up and demanding to be heard.

Matshoshi Matsafu:
But there was very little talk about what would lead to folks to be so desperate, and so disenfranchised, and so broken to have to break up our own resources. It doesn’t just come from nowhere. Thinking about, looking at … We need to talk about colonization, we need to talk about settlement. We need to talk about the remnants of capitalism. We need to talk about all of these things that show up in these ways.

Matshoshi Matsafu:
It’s incredible to me that a lot of those things were not being talked about. So it was hard for me because I had a little bit of PTSD, not a little, a lot. I was afraid to go outside some days because I couldn’t reconcile seeing tanks and young kids, younger than me in uniforms holding rifles, ready to do what.

Maurice Cherry:
Wow. I can only imagine how much of an eerie parallel that had to be to see that as an adult, and then to remember how that was in a totally different country as a child, like, oh my god.

Matshoshi Matsafu:
Right. The only thing that’s different in the world is that some regions, things got given names. Ours was called Apartheid. In Europe, they called it the Holocaust. Here, it’s loosely called slavery. But the remnants of all of that are ever present. That was the most sobering thought.

Matshoshi Matsafu:
But on the flip side of that though, because I always try not to dwindle in the maelstrom, is that whenever there’s destruction, creativity booms. So walking through a ghost town where things are boarded up, but people have reclaimed those boards and created some of the most incredible public art that I’ve seen in all the places that I’ve lived.

Matshoshi Matsafu:
That was a wild experience, people expressing pain through art, like visceral, tangible arts and the dichotomy of emotion that comes as you’re walking through a street, knowing that at any point, a crowd could come rushing through, breaking windows. But then immediately after, folks will be boarding up and painting. Those are such extremes.

Maurice Cherry:
Yeah. Goodness. Geez. It almost feels weird to try to pivot back to talking about what you do for work after focusing on that. But I mean, I think what you bring up and certainly from your unique vantage point of, like you said, having lived through a very similar type of situation as a child, one thing that really struck me during the pandemic last year was how many people I talked with for this show.

Maurice Cherry:
Us, Even in these conversations like you and I are having, trying to reconcile what it is to be black and work during this sort of time and have to compartmentalize the issues that are happening in our society, and what’s going on outside of our windows, while also expecting to show up to our and be productive, and still hit your numbers or whatever you have to do for work. Oh goodness.

Matshoshi Matsafu:
Yeah.

Maurice Cherry:
Wow.

Matshoshi Matsafu:
It was wild. In as much as it feels like it was a total alien experience, I think every single person who was just really in tune, it felt like you’re having an outer body experience because you are looking at the world going up in turmoil. But at the same time you’re facing yourself, like truly having the time alone with yourself to really figure some things out.

Matshoshi Matsafu:
One of those things is reclaiming your time even from work, which I think I saw a lot of evidence of, being black and creatives really standing up for, “You know what, you’re not entitled to have 18 hours of my day. You’re entitled to have this many hours of my day, and I’m entitled to have this many hours. I’m going to pour love into myself,” however that looks like that was certainly something that came up a lot.

Matshoshi Matsafu:
I was appreciative of seeing that too because you just don’t know how many of us are functioning on empty. We never take time off. We always have to work harder than everybody else. We have to explain things and be the cultural competency solution in most of our jobs. Having to do all of that labor without getting paid for it, even though most of us do have a so-called equity, diversity and inclusion department in our workforces or workplaces, they don’t infiltrate the every day. The day to day, when you get on a call immediately after the Floyd incident, and somebody makes a joke about murder as a icebreaker. Like how? Navigating those and having to have that conversation with your manager and having to not teach all of these white people that that’s not the right thing to do.

Maurice Cherry:
Yeah. So I guess I’ll try in some way to pivot this back to work, but not in a complete way. But what do you do to separate yourself from work when that sort of stuff happens?

Matshoshi Matsafu:
Well, black Twitter has been very helpful. The reason is that without black creatives, all of the social media platforms would’ve been dry. The amount of effort that people have put into creating humor out of nothing or making really think pieces just an equipped, like one tweet that makes you really reevaluate things or laugh so much that you can forget for a little bit of time has been helpful.

Matshoshi Matsafu:
Also because of building new language and ways to talk about things that are quite heavy, but there’s a lightheartedness to it, right? The memes that keep coming up across the board, that has been one way to help. Of course, other things include being very intentional about mental health practices, simple things, taking breaks, going for walks, engaging with people that I love, my friends, my family, and also pouring time into things that make me happy. They may not necessarily be hobbies per se, but just things that make me happy. That’s it really.

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
I try to keep it as simple as possible because sometimes also trying too hard is trying too hard, you know?

Maurice Cherry:
No, that’s very true.

Matshoshi Matsafu:
It’s very stressful.

Maurice Cherry:
Yeah. Around that time last year, I was actually unemployed. I had gotten laid off from my job right before Memorial day. I was feeling this sort of a different kind of tension because at that time, I’d say the summer, at least June through August was really the first time in my professional career that I had any sort of a break. That I didn’t have to feel I needed to rush out and get a job or something like that. Like you have down periods between jobs and stuff like that. I would always feel like, “Oh, I got to go find something else.” But I was fortunate that I got enough of a severance and had enough savings that when I got laid off, I was like, “Oh, I’m good for about like four or five months. So I’m just not going to do anything.”

Maurice Cherry:
For me, it was so odd to reconcile this time of rest with this huge time of unrest happening out in the world, and in a way almost feeling guilt for taking a break and not getting out in the streets and what have you. I don’t want to say I rationalized it, but I don’t know. Have you seen the Tony Morrison documentary, The Pieces I Am? I think that’s what it’s called.

Matshoshi Matsafu:
Mm-hmm (affirmative), mm-hmm (affirmative).

Maurice Cherry:
She has a part in the documentary where she talks about her role or what she felt her role was in the Civil Rights Movement. She was saying that I can’t go out and be on the streets. I can’t do that, go out and march and things.

Maurice Cherry:
She’s like, “But what I can do is like publish a writing to get it to a bigger audience. I can support the writers and the poets. I can help fight in a different way.” So I guess even in a small way through this podcast, I felt like, “Oh well, as long as I’m sharing this out still with people, then I won’t feel so guilty or guilty at all about …” I don’t want to say taking up arms because it sounds like I’m joining a militia. But I wouldn’t feel like, “Oh, I’m not out there, you know, marching the streets with a sign or anything.” It was such a weird, weird time because really, I mean, I’ve been a working professional for so long. But I’ve never really had that time where I could just have a break for several months and not worry about what the next thing was that was coming.

Matshoshi Matsafu:
Yeah. That whole existence was some of the most trying. Because for myself personally, I had the added layer of being an immigrant in this country. So I was having such a push and pull in my mind. It was like, “Oh, when my country was going through its liberation, similar things happened.” People on the streets, other countries came and stood up. People were in the crowds, and bodies were out there. But what it means for a black body to be out there is a whole different thing here.

Matshoshi Matsafu:
When I was talking to different types, different groups of folks, those who were adamant about physically being present and also sometimes that came with judgment too, right? That if you’re not in the streets, then you’re not really participating. You’re not really standing for anything. I think that needs to be to, Tony Morrison’s point, that needs to be taken to question because we all have our different roles to play.

Matshoshi Matsafu:
Right? So I think we need to really talk about expanding what resistance looks like from a more holistic view. From yes, we have bodies in the forefront. Yes, we have intellectuals that kind of theorize. Yes, we have business people that are like, “Okay, how do we change these structures?” Yes, we have money people even like, okay, so capitalism is not working. How do we think about something different? How do we build equitable society? Not just in the moment, but what happens after that?

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
That’s where I think design comes in. That’s why I’m excited to be a designer because even in the smallest things that I’m building, those things play a part.

Maurice Cherry:
Yeah, absolutely. I want to go more into your background. I know you mentioned earlier being from South Africa. Tell me about what it was like growing up there. I mean, you mentioned the apartheid. But what do you really remember from your childhood aside from that?

Matshoshi Matsafu:
I mean, my gosh. It’s kind of a Willy Wonka experience. Right? There’s moments of extreme insurmountable joy and awe because of the creativity of black people, the music and art expressed. I think the first time I encountered design was in the township. Most people grew up in what are called like Shanty houses, which are made out of tin, aluminum bars or even asbestos at some point. It’s one room, there’s no electricity, toilets outside, everything.

Matshoshi Matsafu:
But the creativity to make one room feel like a home, that is invention. I remember there was a neighbor that I used to visit who took the covering of of a can, just like a can of … There was a brand called Lucky Star. It’s Sardines essentially. But the graphic art on the label was so striking because we were in that era of just poster designs, so really bright colors and just beautiful typography.

Matshoshi Matsafu:
They spent however long gathering those labels and made wallpaper out of them. When you look at that, and I look at that, and I look at what is called, so-called modern design. I can see that that could easily be in a pop art museum because that’s the kind of art that it was. Or it could be likened to mid-century modern repetition wallpaper too. So I feel design came through just because of necessity. Design is the answer to anguish and pain. Design and art and creativity is the answer. So it was everywhere. I was lucky enough to notice.

Maurice Cherry:
Now being around it as much as you have, when did you decide that this was what you wanted to study? This is what you wanted to go to school for?

Matshoshi Matsafu:
I initially wanted to be a fine artist. I remember in high school, one of my memories is my mom made the decision to send me to what we then called multiracial schools, which meant there was a handful of black kids in a white school, which was interesting. But I really loved my high school because it was in the middle of a forest. I was in boarding school. It was designed like a little European village, I suppose. The classrooms had a lot of natural light, which is not common here. All of the classrooms look like prison industrial complexes.

Matshoshi Matsafu:
One thing I remember is painting. I would paint for hours. I would be covered in paint from 7:00 AM in the morning until 6:00 PM when I had to go back to the hostel. Eventually, when I was head of hostel I had the keys to the hostel. I don’t know why I was lucky enough to be in a really nurturing environment. My teachers believed in me. I would be painting well into the night, and they trusted me.

Matshoshi Matsafu:
That’s odd. It’s unheard of. As a black girl in a white school painting these massive three-by-six pieces, and being free to do so, that’s one of my best memories. From then, I thought, “Okay, I’m going to pursue a career in fine art.” But reality hit when I left school and things were not good. I got accepted into one of the biggest, best art institutions in South Africa, but I couldn’t afford to go. So I found a design school down the road from me. I literally took all of my paintings, my huge portfolio in public transport, and walked up a hill or two, and arrived at the administrator’s office with my ill-fitting clothes and a hat over my head, and sweating, and being like, “I do arts. I think I can do design too, if you give me a chance.”

Maurice Cherry:
Now this school, that was Vega School, is that correct?

Matshoshi Matsafu:
Yes. Yes. I spoke directly to the head of department at the time. His name is Gordon Cook. He’s an eccentric white man, not typical, very much future thinking. He saw me, I’m sure when he saw me, he was like, “Oh my goodness. What? What is this?” I was disheveled and I had this big portfolio case of art pieces. He looked at my stuff. He was like, “Okay, we’re going to give you an entrance exam.” I wrote the paper.

Matshoshi Matsafu:
The last question I answered, and I thought, “Oh my gosh, they’re never going to accept me. I don’t know what I’m trying.” Then they accepted to me. So I ended up doing design and multimedia at the time, which was the introduction to digital, which is interesting, like user interface design, and also animation, and of course communications, and just graphic design. So that’s how I started. I haven’t looked back since.

Maurice Cherry:
Wow.

Matshoshi Matsafu:
Yeah.

Maurice Cherry:
So once you graduated from there, what was your early career like in Johannesburg? Did you feel like the school had really prepared you to go out there in the working world?

Matshoshi Matsafu:
In a sense, yes, because when I was working, there was definitely a push to have more black creatives. So I found myself in a network of just really great black creatives. We all grew up in similar ways. But some of course more extreme than others. It was just really great. Because you’ve got to remember that my country has multiple, I’m going to use the word “tribes” loosely, but multiple cultures too.

Matshoshi Matsafu:
Because of the separations, some of them were just melded all together. So if you can imagine being in a brainstorming session with people from multiple cultures, but we’re all in the same country, all speaking different languages, and just throwing all of ourselves into it. The texture of what came out of those years is amazing. Sometimes I look at that work and I’m like, “Wow. South, Africa’s just a incredible place in terms of creativity, because it’s such a vibrant with different cultures.” So yeah, that’s kind of what stood out. My first job, I was making those really, really terrible user interfaces for phone recharge cards. I don’t know if you all ever had that service here where you prepay for like $30 worth of money to put on your phone so you can call people.

Maurice Cherry:
I remember though. Oh my god, this was back in … I’m showing my age here. This was like back in the early, like late 90s, early two 2000s, I remember those. Because I got my first cell phone in 1999. God. I’m really dating myself here. I got my first cell phone in 1999. I remember having to buy cards to put minutes on it. It was from a-

Matshoshi Matsafu:
Exactly. Yes.

Maurice Cherry:
Yeah. It was from a provider. It was from Powertel, which is now out T-Mobile. But I had to buy cards and then put like 500 minutes on it or something like that.

Matshoshi Matsafu:
Yes. So those little machines that you would buy your minutes from. The buttons were all embossed and made in Photoshop. Terrible. Like minute fills. Yep, that was me.

Maurice Cherry:
Well, somebody had to do that. Somebody had to do that work.

Matshoshi Matsafu:
It was terrible. Then, I mean, the cell phone companies were coming up. So I’d be making little animated banners on the sites that would just live there. Then I worked for a production, like digital print production, which it wasn’t creative work, but I think it just taught me the basics in how to work quickly, print stuff and B2B stuff.

Matshoshi Matsafu:
Then I worked in a network BBDO, subsidiary of like the larger network agency, the global agency. That was really, really fun. I was paired with a copywriter. We were one of the few fully black creative teams, like all women creative teams. We got to work on some really fun campaigns, local ones, but also some international brands. Yeah. Then I remember the turning point when I decided to leave advertising. I loved the advertising world. I learned a lot. I was in charge of people who had been in the industry for so many years. I was like, “I’m making ads and you’re older than me? But you have to listen to what I have to say? Oh my god, this is so scary.”

Matshoshi Matsafu:
It was just so fun. Very exhilarating. Then I decided to leave home because of a number of things, but also primarily because I felt like the advertising industry back home, this is hard, was kind of masquerading as being for black people, as in using black imagery and our colloquialism, like our style, our dress, our lingo, our music, and selling us these things. But in real life, it wasn’t really reflected for most people. One of the so-called marketing research sessions we did was with a group of aunties. I would call them aunties. Most of them, single mothers and caring for multiple people in the household because our culture is as such, is that you’re not an island.

Matshoshi Matsafu:
So they’d be caring for multiple kids. So why it disturbed me is that the company I was working for wanted us to encourage this demographic to use what would’ve been their 12th check in December, which they would usually use to stock up on supplies for the following year because people aren’t rich. You buy extra bags of flour, and you send them out to the village or to the neighboring family. You share, and that’s the way we were all able to survive. So we were trying to encourage these aunties to spend that money on a cellphone contract. I was like, “No. I’m not doing this. I can’t do this. I can’t do this anymore.”

Maurice Cherry:
Yeah. It’s interesting you mentioned that about advertising. So I live in Atlanta. The part of Atlanta I live in is, I want to say it’s the black part of town, but like most of Atlanta’s the black part of town. But the neighborhood that I’m in the west end, is I’ll say one of the lower income areas of the city. It’s a historic neighborhood. Morehouse College is here, Spelman College. Like it’s well known in terms of just black history and whatnot.

Maurice Cherry:
But I do see a lot of the advertising that’s done around here, and it’s always for like prepaid cell phones and things of that nature. For things that don’t really better the community in any sort of way, it’s just like, “Hey, you just got paid. Give us your money.”

Matshoshi Matsafu:
Exactly.

Maurice Cherry:
Not even for well-meaning whole things. It’s like, give us your money so you can buy some shoes. Give us some money so you can buy a combo meal or something like that.

Matshoshi Matsafu:
Exactly.

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
It felt sickening at some point to know that we’re putting things out there that actually catch people’s souls because that’s what we are meant, what we’re trained to do as communicators, as media makers, as creatives is find a nugget that makes people feel that connectivity to being human and exploit, use, expound upon, whichever one you want to use and sell them a product. That felt really disgusting to me. So I left.

Matshoshi Matsafu:
I also just kind of wanted to experience life. I originally wanted to go to Korea to go in … No. I originally wanted to go to Japan, to apprentice with a calligraphy master and eventually become the second black samurai. That’s what I wanted to do. Okay. Because Yasuke is one of my heroes. I was like, “Okay, well, I’m 24. I don’t really have any reason to just stay in one place. I really love of Japan and Japanese culture.”

Matshoshi Matsafu:
I consume Manga and Manhwa and everything. So I wanted to go there. But I applied in Korea as well. Korea got back quicker. I knew that I didn’t have the resources to just travel. I knew that I’d have to work. Teaching English felt like an easy way because I’m really good with languages too. Then I didn’t mind kids. So I was like, “All right. So if I teach English, I can save up money. I can travel. I can build some character, learn about different things. Maybe I’ll still figure out how to be a samurai.”

Maurice Cherry:
I mean. Matshoshi, the samurai, it has a nice ring to it.

Matshoshi Matsafu:
Right? That’s what I thought. I thought. Everything. I was going to have my braids. It was going to be so cool.

Maurice Cherry:
So you decide to leave Johannesburg, leave South Africa, go to South Korea. I’m sure it was a big culture shock. But what ways did I guess … So many questions. One, how was it a culture shock for you? Two, like when you think back to that time, what really sticks out to you the most?

Matshoshi Matsafu:
The funny thing is that I think moving here was more of a culture shock for me than moving to Korea.

Maurice Cherry:
Okay.

Matshoshi Matsafu:
Yes. The reason being is culturally, I think indigenous cultures, we tend to have similar social structures in the sense that you never address your elders by their first name. You defer. There’s a different type of way of speaking, which is more formal or informal. That was familiar to me. There were things like gestures to show reverence for older people. You don’t just hand somebody something without supporting your arm. It was universal.

Matshoshi Matsafu:
All of these things were apparent even before I learned the language. So those things felt familiar. Also our families tend to stay together. Your grandparents raise you or have a part in raising you. You grow up not just as a nuclear family. The idea of all for one, one for all, we share resources. There’s even a word in Korean called chong, which is the direct and same meaning as a word in one of my language called Ubuntu. Ubuntu and chong, loosely translated, mean the spirit of humanity. That we are beholden to as humans and should respect and impart upon each other. That’s powerful to me.

Maurice Cherry:
Interesting that moving from South Africa to Korea was not that big a shock, but moving … Yeah. I could see how moving to the us would be a big, it’s definitely a huge change for that especially depending on the part of the country that you’re in. Because even what you’re describing in terms of that familial structure, I’m from the like deep south, from Alabama. In a way, it’s sort of similar to that.

Maurice Cherry:
The town I grew up in, Selma, is a very insular town. So even as you’re describing that family structure and reverence of elders and things like that, that’s still very much a thing. Now, it might be different in other parts of the country. Actually I know it’s different in other parts of the country. But yeah, even depending on where you would move here and settle in, it is totally, totally different.

Matshoshi Matsafu:
I mean, there were the obvious things, right? There were reactions to my skin color, obviously. We’ll get into the not so nice things about that. There were reactions to my hair. There were to my perfume because when I had moved there, black people, I don’t know anybody who doesn’t use Cocoa butter or Shea butter. That’s just what it is. There at the time, it was difficult to find things that we were accustomed to, like lotion that doesn’t have whitening agent in it, or deodorant. I had to import some stuff because it was just not commonly used. So there were so many reactions, reactions to my hair obviously.

Matshoshi Matsafu:
I remember one day standing at a bus stop. I felt something tugging at the back of my braids. I was like, “What the hell is going on?” I turn around, and there’s these two really small grannies, and their faces are all wrinkled, like crinkle paper. They’re playing with my hair. Then I have this moment of, “Don’t touch my hair.”

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
At the same time, I’m looking at their expressions. I had learned a little bit of Korean then. I understood what they were saying. They were saying A, that my hair was beautiful and that it looked so familiar to a style that their ancient Koreans used to do as well because they also used to braid hair. Right? Braids were something that royalty used to have. So they were talking about that. I decided to focus on that aspect of the conversation.

Matshoshi Matsafu:
Even though it was a teaching moment, like, “Next time, please ask.” It was also a humbling moment for me to have grannies that are 70, 80 years old being fascinated with my hair, and not from a judgemental perspective. That’s the beauty I drew from those moments. But when there was full out racism, oh man. Whoo. I had direct jobs declined because I’m black. People were not shy to say.

Maurice Cherry:
Oh wow.

Matshoshi Matsafu:
Very clearly, “We need you to speak in an American accent in order to have this job.” We had to send photos in with our resume. The moment they got my photos, they would just say, “No, sorry. You’re not what the school wants to represent itself by.” In other words, you’re not blonde, white haired and blue eyed. Yeah. There were some serious racial offenses. But as you know, those are all over the world, if you’re walking around in a black body.

Maurice Cherry:
This is true. But I would imagine, even more so in such a homogenous country like South Korea or in Japan or something like that. It’s definitely a lot worse because what it does … I mean, it’s one thing for it to be racism, but similar to how it is. Well, maybe not so similar to how it is in the United States. It just impedes how far you can go in society. It keeps you, the racism keeps you down literally at a level where it’s preventing employment and any like social rise in that way.

Matshoshi Matsafu:
Right. But at the same time, it was a balance of, yes, I’m being racially profiled, and these things are happening. I’m not able to make a living in some. There were some spots where it was really bad. I was like, “Oh my gosh, if I don’t get another contract, I don’t know what I’m going to do.” But then at the same time, because teaching wasn’t the only thing I was doing there, I was performing music. I was doing like graphic design and design stuff, freelance and production assistant on some films, and things like that, because I never stopped being a creative. In those areas, because of what I looked like. I had so many opportunities. I was a wedding singer.

Maurice Cherry:
Oh wow.

Matshoshi Matsafu:
Because everybody had this idea of a black soul woman in a red dress, just like belting out these love songs from the fifties and jazz. I was like, all right, I’ll play that role. Sure.

Maurice Cherry:
That is amazing.

Matshoshi Matsafu:
Oh my gosh. There was aspects of living in Korea that was so fun. I got perform on stages. I got to do weddings. I got to be in a couple of movies and ads. I got to sing in K-pop songs. It was the truth, and purely because of being black and because of the consumption of black culture. So I have to sit with myself and reconcile some of the really negative feelings around that. But for the most part, I was just like, “Okay. At least in the granded scheme of my life, I can say I once did this.”

Maurice Cherry:
Yeah, no, absolutely. I mean, those are the kind of memories you keep with you for a lifetime, just great stories too, to tell, to get to know people and things like that.

Matshoshi Matsafu:
Yeah.

Maurice Cherry:
So in 2016 you ended up relocating here to the United States, in Minneapolis. How was it, making that change?

Matshoshi Matsafu:
It was brutal. It was brutal. I wasn’t even based in Minneapolis first. I was based in Duluth College. Duluth, it’s a college town, but it’s also an old town. So not a lot of people around my age. It was in the middle of winter. I’d never experienced a winter here.

Maurice Cherry:
Oh wow. You went to one of the coldest parts of the country in the winter. My goodness.

Matshoshi Matsafu:
It was brutal, but it was I think a character building exercise for sure. I don’t think I’ve ever felt more homesick than in those years. Especially considering the political climate too, being in a small town in an almost reddish state, and being highly aware of how many or how few black people there were in the vicinity was very jarring for me.

Maurice Cherry:
Did it ever get that cold in Korea?

Matshoshi Matsafu:
Oh yeah. I mean, it did get cold. I think the Minnesota cold hits different though because of all the other things. Right? Yeah.

Maurice Cherry:
Yeah. No, I feel you. Yeah, totally. Also you came, because if you came in the winter of 2016, I mean, that was just such a contentious time in this country because we had the change in leadership from Obama to the president whose name I shall not mention. All of that combined, did you feel like at the time, that you had made the wrong choice?

Matshoshi Matsafu:
Absolutely. I had so many moments of … I was like, “Why would I choose this? Why, why, why?” But I also know that life has peaks and valleys. If anybody grew up the way that we grew up with all the things that we’ve seen, this is nothing. In the grander scheme of things, there’s growth to be had here. That’s why I think I’m still in the city, is that I feel like the city is a place for treading water and refining, refining.

Matshoshi Matsafu:
This is a place where I refined. Okay. I want to work in tech. But what do I actually want to do in terms of my career? Is my career serving my purpose, innate purpose or is it something that I do for money? Do I feel like the surroundings or the circumstance determine my happiness? I’ve had to be very, very, very active and intentional about answering those questions for myself because it would’ve been really, a much harder time, if not. Yeah.

Maurice Cherry:
Yeah. How has the Minneapolis like creative community been for you? I mean, it sounds like wherever you’ve managed to go or wherever you’ve managed to be, you’ve tapped into some creative community, whether it’s in Johannesburg. In Korea, you mentioned being a wedding singer and all this stuff. Have you found like similar creative opportunities or communities like that in Minneapolis?

Matshoshi Matsafu:
When I’m being intentional about it, yes. This is except for the past two years.

Maurice Cherry:
Right, right. Because of the pandemic. Yeah.

Matshoshi Matsafu:
Right. The thing that I appreciate about here is that even though it was very difficult to find black, brown communities, there are things that show up, like events. If you’re active, you can figure it out. I mean, I had, at some point been planning my month’s activities in advance to go to book launches or independent films or live sketch, anything that would put me in proximity to creativity and art ,like visiting galleries or talks or going to photographer’s exhibition, something, anything. When you do that, then it is very possible to find a bunch of creative people. Right now, I’ve been attending a lot of virtual things and slowly getting into communities. There’s pockets of really interesting things that are happening in the city because oddly enough, there’s tons of funding for the arts, like tons of funding for the arts.

Matshoshi Matsafu:
So when you really go out there, you realize that it may not necessarily be completely futurist yet. But there’s an underbelly of building here that’s really exciting. Black people owning co-ops, black people owning artist collectives and exhibition spaces, black people putting on shows and music and theater and everything. You’re just like, “Wow, this is actually really great. I never expected it here.” I would always be going to Chicago and New York, around LA to find those. But more and more, I think people are actually staying in Minneapolis and deciding to build it here rather than seek it elsewhere.

Maurice Cherry:
We just had on the show a few weeks back, someone that’s in Minnesota. Terresa Moses, she’s an educator at the University of Minnesota. She also has a design studio called Blackbird Revoke. I’ve had other folks on the show, I think in the past, that have been in and around Minnesota. Of course, as I mentioned to you, I know some people there just personally. So I’ve always heard like great things about the community there. I’m glad you were able to really sort of tap into that, to hopefully make it feel … I don’t want to say like home, but at least feel like it’s a place where you can be.

Matshoshi Matsafu:
Yeah, absolutely. I actually know Terresa.

Maurice Cherry:
Oh really? Okay. All right. Nice. Tell her I said hello.

Matshoshi Matsafu:
Oh yeah. I will go tell.

Maurice Cherry:
You mentioned to me that you wanted to talk about how to embrace being a black creative influx. I’m sure that a lot of folks in our audience want to know how to embrace that, especially during the midst of this very uncertain, weird time that we’ve been now in for about two years. Can you like expand on that?

Matshoshi Matsafu:
So when I think about that, it’s essentially how in this time of what it means to be a black body working in corporate world, especially in a creative profession, our creativity is very closely linked to our identity. Now you’re working with your identity, and your identity is now your work. So you have to really think about like, how do I separate? How do I accept that my emotions, my state of being, my home life, all of these things, the fact that I’m in a black body is going to influence my work, whether I like it or not? The expectations that are put on us to be at the forefront of creating new isms, and memes, and things, and media can, I think, lead to a little bit of an identity crisis.

Matshoshi Matsafu:
I’m saying this out loud because I’ve certainly felt that way sometimes, and embracing the fact that A, you don’t have to be one thing. That’s been the biggest thing for me is that yes, the messaging around find your passion, gear your emotion and your focus and your work towards that passion. Then it’ll turn around for you. Hopefully, be equitable.

Matshoshi Matsafu:
Yes. But also we are multifaceted intersectional beings. Right? Half of the time, all of the way that we are around working and being productive and showing that we are worth anything is very Western. Being in one lane is a very, very just constrictive way of being. Part of me kind of realigning myself with my cultural learnings and what feels true to myself has been this, having grace for myself to say, “Okay. So I’m an illustrator, but I’m also a singer, but I’m also a writer, but I’m also a great arter. I’m also a really great technologist.I am also a great philosopher.” These are all the things that I am and more, and I can be good at all of them. I can be good at all of them. I don’t need to be good at all of them at the same rate at all, all the time. But I can certainly not squeeze myself into one lane feeling like that’s it; and if I don’t do that, then I’m not worth anything.

Maurice Cherry:
So what is it that sort of keeps you motivated and inspired these days, like knowing that?

Matshoshi Matsafu:
The funny thing is I inadvertently surround myself, maybe not even physically, but I somehow manage to find people that when we connect, we remind each other of our natural frequency of joy. Whether that be just a conversation or exchanging a message or something, just to reset and remind and inspire. Right? That’s what keeps me going. I have a friend of mine that like a ton of my friends, we don’t maybe not even speak to each other for six months at a time. But when we do speak, it was just like, “Oh, I remember what it feels like to be really happy existing in this time right now.”

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
That’s it. Then on a more practical sense is not stopping the things you know bring you joy on a practical day to day level. Things like journaling doodling without purpose, not thinking of the final product, whatever it may be taking pictures, cooking, doing something that removes you from being in front of the screen all day. Right?

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
Don’t stop doing those things and don’t stop documenting because when you feel like there’s absolutely nothing left, then you have a whole archive of things to remind yourself that you are more than your work. You are more than productivity, and that you are an actual massive being.

Maurice Cherry:
Yeah. I feel like that a collective thing that a lot of people have started to really discover within themselves this year. We hear all this talk in the news about the great resignation and people casting away. Casting away the jobs that they may have once had under pre pandemic life and doing their own thing. I know so many people over the past two years that have ditched their jobs just to become quote-unquote “content creators”.

Maurice Cherry:
That’s a very broad term, but they’re doing stuff on YouTube. They’re doing stuff on TikTok. They’re podcasting. They’re doing any number of things that are not what they were doing beforehand because they realized as society shut down and things got stripped away, they realized what’s really important. For many of them, it was not the jobs they were doing. So they had to tap into who they were and find out how they could become more of that authentic self and really lean into that.

Matshoshi Matsafu:
Right. Then also balancing the pressure of even if it’s okay to be multiple things, it’s also okay to be one thing. I think we have this pendulum swing that keeps the happening where it’s like stick in your lane or be a complete hustler and have five different, six different hustles going on at the same time. But some people aren’t built that way. The true thing is to really take the time to know yourself and understand how you built and go with that. It doesn’t have to look like anybody else’s thing.

Maurice Cherry:
Absolutely. Do you feel like you’re living your life’s purpose now or do you think you’re still searching for that?

Matshoshi Matsafu:
I think that’s a constant search. I the think if I ever assumed that I know or that I have found, then my ignorance is really set in deep, personally. If I don’t continue searching, refining, pivoting, learning, becoming new, then I personally feel that I’m denying the very nature of existence. Our cells change on a daily basis. You’re not the same yesterday as you are today. Our personalities, our minds are constantly evolving. So for me, that means that everything should be constantly moving. Will I find some lanes that I’m comfortable in? Sure. But to say that it’s found, I don’t think so. I don’t think that’s a bad thing.

Maurice Cherry:
I remember, I think this probably went around a couple of years ago about how the body cells replace themselves every seven to 10 years. So in many ways, you’re literally physical not the same person that you were because your body is always in a state of change.

Matshoshi Matsafu:
Exactly.

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
Right.

Maurice Cherry:
To that end, and I mentioned this because you had touched on this a little bit before we started recording. But where do you see yourself in the next five years? Is it staying in Minneapolis? What do you want to do or where do you want to be in the next five years?

Matshoshi Matsafu:
I know for a fact that I’m building my life to be as such that I don’t need to call one place home. I want to be three months in one country, three months in another country, in another city and another, and be comfortable in all those places because I know that that’s what I need, to be a structured nomad, I suppose. Because that’s fun for me. I love learning. I love being immersed in different cultures. I love languages. I love building and designing from that perspective of having multiple sources of influx. That makes me excited.

Matshoshi Matsafu:
So that’s one of the things I’m building my life as such to make that easy for me, whether that means also delving into real estate and understanding how that works, so that I can have another passive income that’s actively happening. So I can facilitate my being able to move around, whether that’s increasing my technical knowledge and skill. I mean, I can definitely work from home from anywhere in the world. But the more proficient I become in my particular field right now or the things that I’m able to do, whether it be the illustration or the UX or design, getting even better at that. So that it’s easy for me to move around, and I’m not encumbered by one contract.

Matshoshi Matsafu:
I think I also definitely want to pursue some business aspirations that I’ve had that have been lurking around. Yeah. So that’s it. I want to be in a state where I can live anywhere in the world for three months at a time, unencumbered, be working whichever way it is. Whether it’s through my own business or through contracts, and to be exploring and learning about different cultures, and also being able to spend a lot more time with my family because I don’t like this, what’s been happening for the past two years and not being able to hold my mom. I need to be able to give my mom a hug, and my brothers. It’s intense. Yeah.

Maurice Cherry:
I just got to see my mom this summer back in July. I mean, it came unfortunately at a tragic time because my grandmother had passed away suddenly. That was the first time I got to hug her was after that happened. Oh my god. Yeah. I know exactly what you mean. I know because I live in Atlanta. My folks live in Alabama. People will ask me like, “Oh, why don’t you do what you do in New York or in San Francisco,” or da, da, da, or whatever. I’m like, “Look, I got to be close to home.” Even if it’s just a state over, that’s close enough. I can’t go too far out like that. I would love to, maybe one day, but yeah. Sorry. That brought up something that was not … I was not expected to go there. Oh my god. No, no, no.

Matshoshi Matsafu:
It’s real though. It’s real.

Maurice Cherry:
It’s real though. Yeah.

Matshoshi Matsafu:
When you feel it in your chest and in your throat, and you realize that such a simple thing … Right now, there’s not even any words for it.

Maurice Cherry:
Yeah.

Matshoshi Matsafu:
Yeah. I mean I want to travel with my mom. That’s the next thing I want to … This is strange. I don’t know why old people like cruise ships, but it’s fine.

Maurice Cherry:
Look, oh my god. My mom, my mom wants to go on an Alaskan whaling cruise or something like that.

Matshoshi Matsafu:
Exactly. Oh my goodness.

Maurice Cherry:
I’m like, “You’ll be by yourself, lady. I’m not doing that.”

Matshoshi Matsafu:
I’m so shook. I’m like, “What? Okay. That’s what we’re going to do.” So yeah. Yeah. I want to build a life where I can fully take care of myself and my mom, and my family. Just be like, “All right, we’re going to be on a cruise ship for the next couple of months.” Because that’s what you want to do. Let’s do it.

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

Matshoshi Matsafu:
So everything is under my first name Matshoshi on the Grams and Twitter. That’s M-A-T-S-H-O-S-H-I. Also my website is Matshoshi.com. You can see all of my design work, and my forays into creative experiments there. So yeah, that’s where I am. Sometimes I’m vocal online, but most times I’m not because I live in the moment. That’s just the way I function. So if you catch an illustration or a thought here and there, cool. But I mean, I’m there.

Maurice Cherry:
All right. Sounds good. Well, Matshoshi Matsafu, thank you so much for coming on the show. One, really for just sharing your perspective of working in the world and creativity in different countries and stuff. But just sharing your story, sharing the deep thought that you have behind your work and around, your artistic practices and everything.

Maurice Cherry:
I mean, I’m kind of getting a little tongue tied. This was such a really good interview because we didn’t really talk about your work that much. But I’m glad that you were able to really just talk about who you were and showing how being a black, creative is not just the work that you do. It encompasses so many different things. I really feel you embody that. So thank you so much for coming on the show. I appreciate it.

Matshoshi Matsafu:
I appreciate the opportunity to chat with you. It was a wonderful experience. 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.

Terell Cobb

Back in the day, the path to becoming a designer might have meant attending an expensive art school, interning at a design studio or an ad agency, and then working your way up the corporate ladder. But this week’s guest, Terell Cobb, illustrates how you can become a successful designer by carving your own path!

Our conversation begins with a look at Terell’s work at Microsoft, and he talks about his day-to-day schedule, working with his team of designers and researchers, and gives a peek into Black Designers of Microsoft and how they work as a group. Terell also spoke about how his athletic career as a football player taught him about design, and shared with me some mentors who have helped him become the designer he is today. With his drive and ambition, Terell Cobb is definitely someone to keep your eye on for the future!

Transcript

Full Transcript

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

Terell Cobb:
My name is Terrell Cobb. I am a design lead over at Microsoft as part of the Digital Transformation Studios.

Maurice Cherry:
Digital Transformation Studios, that sounds super lofty. And I’m sure we’re going to get into that. But before we do, how has 2021 been for you so far? How have things been going?

Terell Cobb:
2021 has been a great ride for me. I believe that last year during the pandemic, it was learning how to be more self-sufficient at home and also taking care of a fam all while taking care of myself as well. And I think within 2021, I’ve gained the appreciation of changing states and moving, and then also starting to center life around just taking care of me and also taking care of the family. It’s been a good ride so far.

Maurice Cherry:
Nice. Also you moved to Texas this year then.

Terell Cobb:
When Microsoft had the opportunity for flex work, I took advantage of that and got an opportunity to come back to the Dallas area and get to some familiarity and also just enjoy the atmosphere that we’re in right now. Sorry to rub that into Pacific Northwest folks.

Maurice Cherry:
I was going to ask what’s changed for you last year, but clearly location’s been a big part of that.

Terell Cobb:
Yeah. And the sun, and being able to see the sun.

Maurice Cherry:
Nice. Being a design lead at Microsoft over the platform that you mentioned, can you tell me about that? What all does that entail?

Terell Cobb:
The Digital Transformation Studios is conglomerate of several spaces within that Microsoft. One of those spaces in which I work in is the business applications group. Business applications group are the parts of the business that actually build applications for large enterprise customers. And being able to sit in that part of the arena of Microsoft, it allows me to see how businesses are, specifically using supply chain and provide certain intelligent solutions to that supply chain space.

Maurice Cherry:
What does your team make up look like?

Terell Cobb:
My team today is made up of a couple of designers and also a researcher. However, one of the things that we kind of anchor to within Microsoft is being able to go with an A1 Microsoft mindset. So I also consider my engineers and PMs as part of my tetra or my team as well. I have an amazing group of people that I get to build amazing things with on a daily basis.

Maurice Cherry:
I feel like that’s been a fairly new development within companies to have a researcher on the design team, as it relates to what you’re doing, how does that work?

Terell Cobb:
I appreciate research so much. I believe I’m one of the biggest advocates for research and also content design. But specifically research, I believe that they’re the silver lining of experiences and if we don’t have their heartbeat of what the experience should be, we’re building in the wrong direction and that could be expensive over time.

Maurice Cherry:
I can see how certainly if you feel like you’re going in one direction and internally, you might think that’s a good a thing and then your users are using it and it’s something completely different. They’re not responsive to it or receptive to it like you want to and you have to go back to the drawing board.

Terell Cobb:
Exactly. I think just being southern and being from the south, you hear those proverbs like it’s wrong to run 100 miles per hour in the wrong way. You would want to go in the right way so that you’re not making further mistakes. Start of the project, they’re essential to the midpoint of the project and they’re essential to the delivery part of the project.

Maurice Cherry:
Walk me through what a typical day looks like for you.

Terell Cobb:
A typical day for me these days are just a bunch of new negotiating. It’s either negotiating confidence of how much confidence a user is going to be exposed to by the options or things that we’re building. It’s also the negotiation of time of how much should the team be leveraged against a certain initiative? What are we talking about six months from now? What are we planning for a year from now? How do we engage the team itself? And I think recently, really taking a step back away from just design as a delivery, as a process, to more of enjoying the process of actually designing and the delivery will get there, but actually taking the time to enjoy the process of discovery, going into definition, going into actually defining from the research and actually delivering something that’s powerful.

Maurice Cherry:
And I’d imagine in that process, you’re also working in sprints and making sure everyone’s up to speed in other parts of the company or maybe other parts of your team, because you mentioned engineers as well that you’re working with.

Terell Cobb:
Indeed. It’s a healthy balance of speed and quality. And I know not a lot of other designers out there have to deal with most of that. But being at a large enterprise company like Microsoft, there’s nothing new under the sun and you have to bring in your best pudding on what that solution could be next, if that makes any sense.

Maurice Cherry:
No, that makes a lot of sense. Now, also at Microsoft, you’re the co-founder of an employee resource group there called Black Designers At Microsoft, which is for black designers at Microsoft. Tell me how that whole thing came about.

Terell Cobb:
Yeah. So the amazing story behind that is that I came into Microsoft and previously started other groups like Dallas Black UX. And also while I was at Capital One, worked with a couple of folks to kind of co-found the Black and Design Employee Resource Group there. When I got to Microsoft, it was more of, hey, I’m just going to focus on my career and a climb. I’m going to leave the Employee Resource Group to the side. I’m going to just stay focused and do this. First day walking in, I meet another black designer and she basically says to me, [Cherryanne 00:09:37] Porter from Houston basically says to me that, “Hey, I’ve never worked with a black designer before you are my first black designer that I’ve ever worked with before.”

Maurice Cherry:
Wow.

Terell Cobb:
And that was the inkling of, okay, here we go. We’re about to do it again.

Maurice Cherry:
You’re like the Grand Theft Auto meme , you’re like, “Oh, shit here we go again.”

Terell Cobb:
Here we go. It then intensified by both of us being on the same team and actually going to orientation. And when we went to orientation, we saw on the screen another black designer that was a part of the studio. We were like, “Wait a second, where is she?” And this is Zoe and she’s been inside of the studio, but pretty much could not find her. And then low and behold, the next all hands we meet with each other and we’re like, “Huh, okay. There has to be more of us. Where are we?” I think along with that and just how big the company is, along with some of the understanding of designers being disenfranchised from not even being inside of the world of design from a black designer standpoint, we took that as an opportunity to build something ourselves inside of Microsoft and grow the talent that’s internal but then also attract talent that’s external to the company as well.

Maurice Cherry:
That sort of feeds into what I was going to ask. What sorts of things is the group doing internally and in the larger community, but recruitment sounds like a big part at least of that external, I guess, outreach of the group. Is that right?

Terell Cobb:
Indeed. I think if we look at just some of the general grounding of the group itself, it’s based in on not just looking at one form of design. That’s one of the biggest differences there. It’s not just a UX designer and you’re a part of the group. It’s more so of design with the capital D as it’s reference from our fearless leader, Jonah Sterling, it is design, it’s research, it’s producers, it’s data science, motion designers, audio designers, front end development, illustration. All of these people are a part of the group and the key points there is getting into the intentional community to influence diversity. Influencing diversity internal to therefore make it external, just creating that ripple so that we can continue to build from the inside out and doing that, it was growing the community itself by creating teams channel in safe places along with the opportunity to do share outs, hackathons right now anybody in the group can kind of spin up a opportunity for someone to have a quick review and they can basically get started and you’ll have multiple people join in to give them feedback.

Terell Cobb:
And it’s different because you’re getting feedback from friends in that sense. I could tell you, “No, bro, that’s not going to make it. That may not make it bro, or I like that, that’s going to be amazing.” And it’ll be a little bit different because it feels that it’s coming from that place that we get most of our things from that feels safe for us. Continuing to drive that type of community was important to us and doing it internally through the community piece, but then also reaching out to external to the community and going after middle schools and high schools and also HBCUs. Last year we had a couple of events where we actually partnered with some of the HBCUs out there to kind of expose the craft of design to them.

Maurice Cherry:
Interesting. When I was in an HBCU some twenties years ago, one of the first company, one of the first tech companies I interviewed with was Microsoft. And actually, I mean, I think I’ve told this story on the podcast before I’m well outside of college now, so I can sort of tell the story, how I scan my way in there. But essentially I was a math major in college and my whole thing was I was part of this program that was sponsored by NASA, my scholarship and everything. And so the goal was like, oh, well, when you graduate college, you’re going to work for one of these NASA facilities. I had interned at two NASA facilities. So in my mind, I’m thinking, boom career set when I graduate NASA. 911 happens.

Maurice Cherry:
And when that happened, the funding for my program got pulled and it went towards Homeland Security. And so this whole guarantee of, oh, well you’re going to work for NASA when you graduate completely gone. I’m like, damn, I got to find a way to … I don’t know what I’m going to do when I graduate because I was working at the high museum selling tickets for $8.70, not making real kind of money and really had no prospects of career stuff. But I had sort of gotten in really good with the computer science department, with the secretary there, shout out to Mrs. Banks. I don’t know if she is even still there or not, but got in really good with her, started hanging out in the computer lab and stuff, started hanging out in her office and that got me access to this interview book.

Maurice Cherry:
And the interview book was basically juniors and seniors that were interviewing with all these companies and all you had to do was just kind of slip your resume in, put your name down. And I was like, “I’m just going to slip my resume in there and write my name in it.” And I interviewed with real player to show you how long ago that was, that went nowhere.

Maurice Cherry:
And then I interviewed with Microsoft and I remember, God, I don’t remember the woman’s name, who I interviewed with, but it was a black woman interview with her and she gave me one interview question. She was like, design an alarm clock for a blind person. And she slid over a sheet of paper and a pen. And I was like, just walk me through your process. And I’m like, “Oh, okay.” So I was talking through, oh, we should do this. And it should vibrate and maybe have sound and all this kind of … She was like, okay, all right, great. And she took it and she put it in a folder, shook my hand. And that was it. That was the interview. I was like, “That’s it.” Apparently it was good enough because they flew me out to Seattle to do an interview with Microsoft and they had it in this sort of almost an elimination style.

Maurice Cherry:
I don’t know if the interviews are like this now, but you do the first interview and if you pass the first one, you go to the second one. If you pass the second one, you go to the third one. And this was all day for an internship. I remember because this started at maybe 8:00 AM and it was getting until around maybe 7:00 PM. I was tired. And I forget what the question was, it was something about notepad and right to left text or something. And I think it was at that point that they realized, oh, wait a minute, you’re not a computer science major are you? Because it was some programming stuff and I was like, I don’t know. I don’t know how to do this and I didn’t get the internship, but I remember vividly being on the campus and everything and when I think of companies that have sort of given me a chance in college, like Microsoft was that one company.

Maurice Cherry:
The fact that you all are still doing HBCU research now some 20 something years later is a testament to the fact that you all have put skin in the game and that it’s not just, oh, we need to look for a diversity. Where should we look? Why do I look at black colleges? You all have been doing this now for a long time.

Terell Cobb:
Indeed. It’s incredibly rewarding not just to win by yourself, but it’s also incredibly rewarding to see others win and see that spark in a high school as I, that, wait a second, I can become a designer. I could be a researcher, I can work at Microsoft is like, yeah. Actually, one of the previous workshops with CodeHouse, shout out to CodeHouse in Atlanta who brought in 29 students from Morehouse and Spelman at the time. And we ran through just roughly about a six hour to seven hour workshop with design. And you can kind of see the amazing minds that are there and applying design thinking to those amazing minds, our leaders coming behind us are going to be crazy good. And I think that is the reward that most of us get from that because there’s a great chance that, hey, we will be working with these leaders later on in life. It’s extremely rewarding.

Maurice Cherry:
And I would say the fact that you mentioned high schoolers and middle schoolers, you’re going past just reaching them while they’re in college. You’re getting them at a really pivotal age when they can make a decision on where do I want to go in terms of, I want to say my career, I really think it’s unfair to sort of burden an 18 year old with that anyway. But the fact that you’re showing them that this is an option because now social media and technology is ubiquitous. When I was a teenager in the nineties, there was Game Boy, there was Tomagotchi, there were Super Nintendo. It was all consumer electronic sort of stuff. Certainly no smartphones or anything like that. But now you can show them you can be more than just a consumer or a user. You can be a creator. You can be someone that makes this stuff and to show them that at such a pivotal young age, at middle school and high school is really something.

Terell Cobb:
That is so key. I mean, and even if they choose not to become a designer, we still win because we just taught them design thinking. So now from that point on, they have that emotional intelligence or that critical thinking mass to take with them to the next adventure. And I think that’s part of the reward back to us as well.

Maurice Cherry:
Absolutely. Now, let’s kind of switch gears here a little bit. You mentioned being in Texas, is that where you also grew up?

Terell Cobb:
No, actually I grew up in South Florida in a small town called Boynton Beach, which is roughly about 40 minutes north of Miami.

Maurice Cherry:
Okay. Growing up there, were you exposed a lot to design and everything?

Terell Cobb:
Not at all. I like to tell the story this way, that growing up in Boynton and also just South Florida in general, you’re growing up in a football arena. And there’s not much else to do outside of football. You got the notoriety that you had from football. There’s countless of times of pretty much kids starting playing football at four years old. And you could see those kids training and practicing with parachutes at four or five, just trying to get faster and trying to get better there. It’s still to this day, I believe the, South Florida is leading in the most NFL prospects within the country. And it’s not by chance. It’s just simply because of the arena of how important football is in those areas. Because of that, that had gave me an opportunity to be exposed to being a football player, but just doing it a little differently.

Terell Cobb:
I still had some of the tenacity of being on the D line and knowing how to use my hands and knowing how to be fast and running 707s with different people. But I also found a unique ability of me actually setting up the field. I love the aspect of walking each five yards and putting a cone or a shoe or a hat down to say that this was a first down or this was a yard marker. Or this was going to be the goal line, even down to cones. I’ll never look at orange cones the same ever in my life, because I would take these orange cones and you would create different patterns a pentagon, a triangle, a square, a circle, depending on the pattern that’s on the ground, that’s where your feet or your toes would interact with in order to beat the drill.

Terell Cobb:
I got really good at setting up these cones. I really started to understand well, wait a second, I’m good at this. I can also draw a little bit, where is this leading me? I just said no, don’t worry about it. I’m good. I’m going to just put that to the side and continue all with life as is. But the opportunity presented itself when I got into college once leaving the Boynton area. But I appreciate the hardships of Boynton because it taught me the lessons that were needed to be a champion on the things that came to me afterwards.

Maurice Cherry:
I know what you mean about sort of growing up in that crucible of football. I mean, I’m from South Alabama, well, South central, Alabama, and it’s either Alabama or Auburn. One of the two. I know what it is about … And I remember, there were like those Pop Warner football leagues and stuff like that. And I wanted to be, and my mom was like, “No, you’re not doing that.” But I remember there would be six-year-old, seven-year-olds in pads tackling. I remember that vividly exactly about growing up that whole thing about just really getting into football.

Terell Cobb:
Exactly. I mean, that’s exactly it, but I think this is how I attribute back how football taught me design because being one of those four-year-olds out there with the helmet that can’t hardly hold myself up, but making tackles, it’s not just the football field, it’s the people, it’s the cars around the football field. It’s the atmosphere of the lights being on at a certain time. It’s the concession stands as part of food trucks before food trucks were food trucks. It was all of that atmosphere that kind of gave me a sense of how not knowing at that time, but how designed was working or things were designed around me.

Maurice Cherry:
I was in the margin band too in middle school and high school. Every Friday night, it’s a whole production. It’s a whole production. The whole thing. Absolutely. Given that football kind of taught you design in that way, that’s also why you ended up studying it I would imagine in college and you went to Washburn University.

Terell Cobb:
Well, the interesting thing, I went to Washburn University but I think prior to Washburn University, I like to tell the story this way that I earned my way to the middle of Kansas at a junior college called Butler County Community College by not getting great grades in high school. That also earned me the opportunity to see a deer for the first time, see a cow for the first time, didn’t know turkeys could fly found that out.

Maurice Cherry:
And they’re mean, they’re very mean bird, probably because we eat them every year.

Terell Cobb:
It was so interesting to have that culture shock from being from the city and brick and hardship and going into country immediately. The school itself was a college, a cemetery, a Walmart and an oil field. The rest was just the school. It was a stark reality of, hey, if you want to excel in life, there are some things that you will have to do. And that stark reality basically helped me understand what the direction I wanted to go into next. And so as part of the Juco experience, you get an opportunity for teams from across the country to come in and actually draft you or actually pick you up or recruit you from that location. It’s actually high school part two. And during that process, the school Washburn drove about maybe three to four hours down the road in Kansas and actually picked me up and took me to the campus.

Terell Cobb:
And it was one of those moments where you step in and look around like, man, this is nice. I think I could do this. And it was slow and it feel like academia that you saw in the movies for my aspect. And I think that’s what drew me to it because I saw a calmness or a piece around it. And I think heading there starting out, it wasn’t immediately designed. It was jumping directly into psychology. And I thought for sure that I was going to be a psychologist actually getting up to somewhat of my senior year in psychology classes and actually stopping and actually working as security as part of the design as part of the work study football job, making sure that people log off the Mac lab, I guess, I got the opportunity to play on the computers from every once in a while. And the classes that were more of the later classes were the illustrator, the photoshop. I’m going to date myself now, flash multimedia or SWiSH Max classes.

Maurice Cherry:
Oh my God. SWiSH. Oh my God, you took it back. You really took it back with SWiSH.

Terell Cobb:
Being able to see those classes actually happen gave me an opportunity to be like, “Wait a second, they’re doing what I was doing, but drawing, but they’re making stuff move. They’re making their drawings move.” How is that happening though? Wait a second, and think after talking with the professor that night, I actually went in the next day and changed my major to art and then started to go down this path of being the football player, leaving practice with an easel, running across the football field with an easel and all of my art materials and running into the art lab and of course sitting in the corner because pretty much I’m just leaving football practice and fresh hour, but still just leaving football practice, four hours of practice.

Terell Cobb:
I dealt with that dynamic for two more years and it was incredibly beneficial for me just simply because it started to introduce me into graphic design. I was always exposed to graphic design on via bubble letters, airbrush tees, just drawing certain things for certain people, but just didn’t know that it was actual profession behind it. And being able to make that correlation there kind of sparked my career into the design world.

Maurice Cherry:
Getting that exposure to it, knowing that this is something it’s an option that you can take because prior to that design was something that you just sort of consumed, like you mentioned in these sort of bubble letters and stuff like that. But now knowing, oh wait, I can do that too. I can make that. I mean, even that whole setup about leaving football practice and going to our class with a easel, sounds like a feel good holiday movie or something. I mean, if you ever want to transcribe that to a story, I bet Hallmark can pick it up. That sounds pretty dope.

Terell Cobb:
I may have to do that. That’s a good idea. I receive that.

Maurice Cherry:
What were those early days post-college in terms of your career, you’ve graduated now, you were majoring in graphic design. What was next after that?

Terell Cobb:
It was the real world posting its first challenge to me. I think that first challenge to me was getting into an internship. Well, as a football player, you’re spending 40 hours a week on football. So you’re not able to kind of go and market yourself to other agencies and say, hey, I’m a designer. I could do these things. It just wasn’t acceptable or it wasn’t available for you. But in my case, the real world slap that was put in front of me was in order to work my internship, which I finally got at a local ad agencies, Joan Youths And Partners there in Topeka, Kansas, I was only able to do that into on Fridays from roughly 8:00 AM to 3:00 PM. In order to be able to do that, I’m finished with school, but of course I have to make money somehow.

Terell Cobb:
I hustled my way into talking to a Topeka Youth Project, a local small school that taught kids that were 15 to 21 jobs and life skill readiness. It was my job to go out to the local fast food restaurants, the local libraries, anybody who had a job for 18 and actually become a business representative and pitch the school to that company to say, hey, I know you manager, and I know this kid that I just taught this class, you guys sound like you’ll be a great match. You should probably hire this kid. Getting the kid hired, that was the first indication of negotiation and stakeholder agreements. Knowing how to actually have those conversations. While doing that, I was only able to work. I believe it was 28 hours a week or 25 hours a week with that company. In order to do that as a business representative, I bargain to say, hey, let me help you with your website and your logo as well.

Terell Cobb:
I’ll do your website and your logo, and I’ll also be your business representative. I was doing that. A normal day for me post college, and this is how bad I really wanted to be in this world of design. I worked from 8:00 AM to roughly about 3:00 PM, Monday through Wednesday at the Topeka Youth Project. On Tuesday through Thursday, I was working overnight shift at FedEx, unloading trucks. Pretty much from roughly about 3:00 AM to 7:00 AM. And then in between the Thursday to Friday, I was also unloading packages to Target and basically being a Target shelf, stocker. All so that I can get the internship completed and also get the first level of experience out of the way.

Terell Cobb:
Now, I’m not saying that most design now coming out of college, don’t have to worry about those types of stories and those types of hustles but it was just a slightly different for me being in a small town and just wanting to make this work so bad and not wanting to go back home and say hey, I didn’t do it, I didn’t make it. That was the start of hard work makes something out of you. But then also hard work creates the character that you need as you continue to progress.

Maurice Cherry:
You were hustling.

Terell Cobb:
It had to happen.

Maurice Cherry:
That reminds me a lot of, there’s another guest we had on the show several, several years ago, his name is Ben [Lindo 00:32:19]. He’s a industrial engineer out of, I think he’s out of Philly or Pittsburgh, one of the two, but he was mentioning how he would do design school. He was doing design school and it was UPS driver at the same time. And would come to class in his UPS uniform and the teacher would always have something to say and that kind of thing but he made it work. I mean, when you’re out there on your own, you have to hustle to make that happen. You have to make those sacrifices, those compromises. And it sounds like you really, really hustled to make that happen. Props to you.

Terell Cobb:
Exactly. And I think it benefited me a lot just because I was exposed to so many different conversations, so many levels of small talk. Many levels of strategy. I knew that I can unload a semi truck of boxes from FedEx in under 56 minutes, holding that record doing that. But I also do the pattern of, if I unload the boxes too fast on the belt it could stop the belt and then pretty much that makes the day longer for other people that are behind me. It’s just so many lessons that are there through that first year out of college.

Maurice Cherry:
I mean, it really teaches you the value of hard work too. I mean, I think it’s one thing, if you’re going to school and you manage to land that super cushy gig right out of school, and it’s not too hard, but not too easy. It’s kind of Goldilocks kind of situation but I mean, it’s another thing when you get out and you really have to hustle to carve your way into a position or to get to a point where you’re going to be you hopefully setting yourself up for the future in a good way.

Terell Cobb:
Exactly. I think, just being the first of the family to go to college, first of the family to graduate college, you knew and understood you are your help. It wasn’t something else that you can wait on, you were your help. You were ascending this next avenue in arena so that you can then help your family on the back end of it.

Maurice Cherry:
Yeah. Like you said, it’s that thing where you don’t want to go back home defeated. You don’t want to go back home like, oh, I couldn’t make it. That also pushes you and drives you to succeed as well, that feeling.

Terell Cobb:
Yes.

Maurice Cherry:
So you worked for a number of companies between being in Kansas, being in Florida, being in Texas, worked for a lot of places. When you look back at your career, now that you’re at Microsoft, do you feel like there was a particular moment or a particular job or anything where you felt like you had leveled up?

Terell Cobb:
I think it was the first opportunity to leave South Florida in working in the banking industry down there at the credit union where I started to see the shift from design as more so as a graphic or tangible color or button style to design as a product experience element moving forward. And I think that was the transition from working in South Florida at the credit union to getting a first big break at working for Barclays Bank here in the Dallas, Texas area. One of the mentors that I had at the local ad agency who saw the drive of what I was doing actually called me up from the South Florida area like, “Hey, you want to try this out?” It’s like, “Well, no, I’m pretty good. I’m building websites. I’m doing club flyers. I’m good.” I’m around my family, but not too close because I don’t want them to get on my nerves, but pretty much I’m close enough so I can go hug them and come back.

Terell Cobb:
But it really was at that point in which I saw the level kind of change because it went from me being just a single designer/webmaster slash business representative at that local credit union, continuing that trend to not just being a slash, but being a focused disciplined designer. And that was coming into that first level of product design at Barclays there with that company.

Maurice Cherry:
Now also prior to Microsoft, you worked for two other pretty large companies, you worked at Capital One, you also worked at FedEx. Was it a big sort of culture shift going from those two companies? One’s logistics, one’s banking. Going from that to a strict tech company? Was that a big shift?

Terell Cobb:
I mean, the amazing part of my pathway is that each one of those companies had a different element that I’m using today in firms of my leadership and moving forward. Within Capital One in the FinTech arena, you’re constantly thinking about how could you do things as a group? It’s all about innovation, how to be … And I greatly appreciate just being there in that arena because Capital One didn’t consider itself to be a bank. It happened to be, as they say, a tech company that so happens to be a bank. And that opportunity of being with instant innovation all the time and blue sky thinking and being able to stop projects from releasing and saying like, “Hey, wait a second. Was that innovative enough? Are we really proud of this thing.” To the introduction of service design and the introduction of critical thinking and the folks from Adio coming in and merging into that as well.

Terell Cobb:
Capital one taught me somewhat of the college of product thinking and design external to school, external to that other layer of just design as a button color or movement. Capital One gave me the piece of grounding then moving into FedEx it was like, “Wait a second, I’ve learned all these things. I can put these things to use. Do you want to see them?” And they’re like, “Now we’re a little bit more safe here.”

Terell Cobb:
We’re just a bit more safe. But I think the logistics side of FedEx taught me the technical aspect of what an engineer actually has to do in order for packages to arrive at a certain time. Understanding, and I’ll never forget this quote, from one of the engineers he basically said to me, “Terrell, how do you build a tank?” And I was like, “What do you mean? Military builds, tanks? Send a request to the military, they build a tank.” And he was like, “No, if you had to build a tank yourself, how would you start?” And then I think this is similar to your clock challenge here, where an engineer thinking about a tank is going to be the larger items first and then start going into the cogs of the tank and building the cogs to get back out to the larger things, having a base building in, and then starting building out the shell of the tank and the color of the tank, none of that matters to them.

Terell Cobb:
And that gave me the perspective of how an engineer thinks versus a PM thinks versus a designer thinks. Wrapping all of that around and kind of turning the corner here and going back to where I’m at at Microsoft, it was the critical thinking and also being able to take chances at Capital One, also along with the technical understanding and saying, “Hey, I can’t go build this tank without these particular cogs. They’re important to somebody they’re important to the experience. And then they’re also important to the team that’s building it.” So how do I become a technical designer/team player and then entering into one of the largest tech companies in the world, it’s how do you mash up all of that experience into something and make sure that you can speak the engineering language, you can speak the PM language and you also provide the quality and also the confidence within a customer using this product moving forward. Hopefully I’m answering that question in the best way.

Maurice Cherry:
No, that makes a lot of sense. I mean I think that you always want to think about how you can transfer skills when you’re going from one really big, I think, type of company to another one. And granted all of these do have tech sort of at their core in some way, you’re just using that tech to solve different problems.

Terell Cobb:
I think doing that and also keeping the duality of going back to football, no man left behind or no person left behind and going back and sitting having lunch with the engineers, sitting next to them and saying, “Hey, show me what you did because that was kind of dope. How did you do that.” Spending the time to get to know your teammates, getting the time to actually make this analogy football there’s 93 plays to a game. How many times have you talked to your coworkers in a week? How could you start to understand what they’re going through? How could you start to extend to your team and actually give them the same type of comradery that they’re looking for because you are spending a lot of time with that person. Just anchoring back those principles inside of the duality of also having the technical chops to talk workshop, if you needed to.

Maurice Cherry:
Yeah. And one other interesting thing, and you sort of talked about this, I think a little bit at the top of the interview was that you’ve also, maybe not at each of these companies, but certainly you did this at Capital One and now Microsoft, you started these black ERGs. Was it important for you to sort of build that community as you started? How did that manifest itself?

Terell Cobb:
It was incredibly important to see other people like me within the design world. I think like most designers starting out, you’re constantly looking for mentorship and sometimes you have to be the mentor as you rising yourself and you’re providing advice to people, however, you are looking for some advice yourself. And I think within the different groups, it was the opportunity to not only see people that look like you doing amazing things and being able to connect with them and saying or resonating against saying, “Hey, I’ve gone through that as well or I have had this conversation as well,” to more of just that comradery of, have you had an ethics conversation about this design? What did they say about this ethics conversation and being able to just talk shop with them in that way? I think the pleasure that I have within all of these groups is they’re all unique and all based on just different stories of how they got started.

Terell Cobb:
I think within the Capital One space, there were roughly about six of us that stood up at an all hands and were like, hey, I see you. I see you. And it was like, “Well, maybe we should stay in touch.” And then it went from, maybe we should stay in touch to maybe we should have meetings to maybe we should influence more recruiting and to maybe we should have somewhat of a council or somewhat of a type of event. And then with the Capital One piece, it was then like, how do I extend that outside of the company because I can’t just do it from Capital One. How do I also extend inside of the Dallas area? So then it was working with the Bobby Lloyds, the Michael [Tingling 00:44:03], the Labora Willis, the Adrian [inaudible 00:44:06] to kind of expand just create a ripple here in the Dallas area but then also move around to the Houston area.

Terell Cobb:
Just trying our best to create events and also create community for us here. And I think that just followed me just going into the Black Designer space at, at Microsoft because it was so welcomed by other people in that community too. And also the aspect of being able to create something that you know 20 years from now will still be there is something that I get chills over just simply thinking like, hey, that group is going to be amazing because we set it up in that way and they have their heart in the right place.

Maurice Cherry:
When you think back throughout your career, you mentioned mentorship. Who have been some of the mentors that have really helped you out in your career?

Terell Cobb:
Oh, wow. I think there’s some really awesome people out there. I say, some folks like Ty Griffin comes to mind, then there’s, people who were helping that didn’t even know that they were helping, that were just more friendships, right? Like the Tim Allens out there, the Danley Davis is out there. The folks like Dr. [Oco 00:45:30] who was pretty much the person who kind of helped me shift from saying I’m just going to work in a hospital to, hey, I’m going to go to college. I’d say those people along with the Pastor Hicks in Topeka Kansas, the Lisa Carters that are out there and all the football coaches associated with it. Those are some of the people that kind of gave me the drive, but also instilled that I cannot just keep this to myself. I have to also throw the rope back for somebody else or leave a breadcrumb for somebody else behind me so that how I can help them would be beneficial to the future.

Maurice Cherry:
In recent years, what would you say has been, and the biggest lesson that you’ve learned about yourself?

Terell Cobb:
I would say that I’ve learned that I am incredibly a nerd when it comes to setting things up and being deeply in process. I read some of the similar books throughout the week. I have my coffee and sit on the stoop and actually bask in the sun, but also just that appreciation of designing the little things. And I think this recent trip that I just took to Denmark for a designed workshop there kind of reminded me as I saw enabled person, actually leave the train with with a wand who was basically visually impaired, actually get off the train, stumble on the little ground stubbles and pretty much make their way like a boss to the escalator without any help. It was a reminder to me of, somebody thought in process of this person leaving the train in this way, somebody thought about the doorknobs that’s in front of me. Somebody thought about the angles that in front of me, what are the processes that I’m creating for people behind me as well.

Maurice Cherry:
How do you define success now?

Terell Cobb:
I define success a little differently from other people. And I say that just to say that I look at success as an opportunity to succeed. As long as you have that opportunity, I don’t believe that you fail. I believe that you learn. And if you have that opportunity, you started in part of that success you’ve already … To start is success.

Maurice Cherry:
I like that. Because oftentimes really, it’s just that first step that you have to make.

Terell Cobb:
Exactly. You have the thought and you have a couple of seconds to go about that thought or a couple of minutes or that first step. I think we’re a little bit hard on ourselves sometimes and I think just to start in itself is success.

Maurice Cherry:
What would you like the next chapter of your story to be?

Terell Cobb:
I have this grand dream of creating pillars of design practices across the country and their anchor inside of some of the experiences that I’ve had over in the past of the different tech companies or the different businesses that I worked for. But I think mostly the desire to have those communities or those practices is kind of related back to just one in the lead break grounds. My desire is to work on the next 20 years now. There’s an amazing book out there Called What The Forecast. And I look at it almost every week because it kind of puts these brain like exercises in front of you that says it’s five years from now. I am doing this, I’m driving this. I am living here. And it goes from five years to 15 years to 20 years. And I’m constantly thinking about those 20 years just because if you don’t start on it, it’ll just sneak up on you.

Terell Cobb:
That’s my next step here. Just continuing on that path of thinking about those next 20 years. And I have breakfast with some amazing guys, almost every other weekend. And we joke and say, well, we’re talking about our 85 year old self and what our 85 year old self is eating. What could we do now to help our 85 year old self? Are we at 85 and we’re riding motorcycles to eat for breakfast? Are we pulling up in our wheelchairs? Do we have scooters? How mobile do we want to be when we get to that age? I’m constantly thinking about the future in normal yet intriguing terms of life now.

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

Terell Cobb:
Yeah. So if anyone wants to find me on LinkedIn, definitely reach out to me. If I can’t get back to you, I promise you, I will find somebody that can get back to you. Terrell Cobb, T-E-R-E-L-L C-O-B-B on LinkedIn. If you want to follow me on Instagram, it’s a vintage_424. I’m always there. And those are some of the main channels right now where people can find me.

Maurice Cherry:
All right. Sounds good. Well, Terrell Cobb, I want to thank you so much for coming on the show. One for just giving a peak behind the curtain as to what it is that you do at Microsoft and even how you’ve helped to create community not just inside of Microsoft or designers there, black designers there, but also the help out in the community as well, but really sort of showing the fact that perseverance really the way. There’s so many paths into design, there’s so many ways to be a success or to do anything really in this industry. And I think what your story really illustrates is that there’s no one single way to do things. There’s no one way to be a success. And so hopefully people will get a chance to hear your story and we’ll take that to heart. Thank you so much for coming on the show. I appreciate it.

Terell Cobb:
This was incredible. Thank you so much, Maurice, I really appreciate it.

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Miles Anderson

When I first chatted with Miles Anderson, he said that he’s “just a normal guy who works hard.” But then I heard his story and the growth in his career and well…Miles is no normal guy — he’s extraordinary!

Miles talked about his recent move to Seattle in the midst of the COVID-19 pandemic, starting on the Xbox team at Microsoft, and how he’s getting along during this time. He also spoke about his time at IBM and how it helped him grow as a designer, the power of self-education in tech, and what he would do in his career if failure wasn’t an option. Miles is finally getting the recognition he deserves, and I’m glad to have him on the show to share what he’s doing with you all!

Sponsor

Facebook Design is a proud sponsor of Revision Path. The Facebook Design community is designing for human needs at unprecedented scale. Across Facebook’s family of apps and new product platforms, multi-disciplinary teams come together to create, build and shape communication experiences in service of the essential, universal human need for connection. To learn more, please visit facebook.design.

Nick Caldwell

Nick Caldwell is passionate about inspiring people to get into technology. As chief product officer of Looker, he oversees the company’s product, engineering and design teams, and also serves as one of the public faces of the company. (And that face is all smiles — Looker was acquired in 2019 by Google for $2.6 billion!) What does life look like on the other side of such a big buy? Well you’ll just have to listen and find out!

Nick talked about how his dad’s Tandy 1000 sparked his love of programming, what it was like attending MIT and interning at NASA, and even went into his years at Microsoft and Reddit before joining Looker. From here, the conversation turned towards the state of the Valley, and how he sees opportunities out there from his point of view. Nick also shared what success looks like for him at this stage of his career, and talked about how he gives back to the next generation of Black technologists. It’s really an honor to share Nick’s story with you all!

Links

Transcript

Full Transcript

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

Nick Caldwell:
Hey, I’m Nick Caldwell, Chief Product Officer at Looker.

Maurice Cherry:
So talk to me about your work at Looker. I’m curious, what is an average day like for you there?

Nick Caldwell:
Oh, complex question. I’m a Chief Product Officer, so that means I’m responsible for product engineering and design. I also have the security team, which I’m responsible for. My average day is honestly really hard to predict. But I can tell you what I aspire for it to be is that I’ve enabled all the people who work for me to get their best jobs done without my help.

Nick Caldwell:
That is to say, if I’m doing my job correctly, all of my team members know exactly what they’re supposed to be doing to contribute to the overall strategy, and then I don’t have to jump in and bother them about it. They can do it themselves.

Nick Caldwell:
But what that leaves for me is, in the instances when my team can’t do that execution without my help, I get to jump in, get people unblocked, help solve problems. And I guess, the position I’m in, only the really juiciest most difficult problems bubble up to me.

Nick Caldwell:
And then beyond running the team in that way. The other cool thing you get to do as the Chief Product Officer is you get to be kind of a public representative for the company. So I spent a lot of time talking to customers. Just before recording this podcast, I was doing an interview with a news publication to talk about our upcoming release, Looker Seven. Just generally finding ways to represent the company publicly, not just by talking about the product but also by bringing my own personality to the mix. It is a really fun part of the job.

Maurice Cherry:
So it sounds like, one, you help with the vision being the representative of the company, but then also ensuring that the people under you can manage and do strategy and actually contribute to the overall product.

Nick Caldwell:
Yeah, for sure. We’re scaling. Looker is a fast growing company. I guess I should mention, we just got acquired by Google, and that’s kind of a testament to how well the business is going. But as we scale, we have to think about how does our organization handle more people who work for us?How do we handle the much larger volumes of customers that we’re going to have? For me that means thinking about, obviously the product, what we’re building, but in some sense, I also have to treat the organization like a product as well. It has needs that grow and develop over time as well.

Nick Caldwell:
So, trying to figure out where our next generation of leaders is going to be, trying to empower them with all the same sort of skills and techniques that I would want to apply myself. But I can’t be everywhere, so we’ve got to have that next generation of leaders come into play. And leadership development and that sort of class of problem is really fun. I enjoy coaching folks, mentoring them and then seeing them go up notches in their career. And I’ve been fortunate, for the past few jobs I’ve had, to be in positions where I am doing a lot of that scaling and growth and people development, and get to see the fruits of that bare out in successful products. And also just seeing people get further along in their careers.

Nick Caldwell:
Yeah, it’s fun. I enjoy that part of my job quite a bit.

Maurice Cherry:
Yeah. As I was doing my research, I was looking up the acquisition, $2.6 billion.

Nick Caldwell:
Yeah.

Maurice Cherry:
Wow.

Nick Caldwell:
Not bad. Not bad for a boy from PG County. Yeah, we’re doing pretty-

Maurice Cherry:
I know all that money didn’t go to you, of course. It went to the company, but I’m curious, how did that acquisition change your life?

Nick Caldwell:
There’s a couple of different ways to answer it. I’ll give you the corporate answer. I think you want the real answer. The corporate answer is the corporate answer is we’re going to be … Sorry, the deal hasn’t actually closed down. I think it will probably close by the time this podcast airs, but what it means from the product perspective is we’re going to be able to accelerate all of the product functionality we want to build. We’ll have access to greater resources. Google plus Looker enables us to really fully deliver on the vision that we have for the overall product.

Nick Caldwell:
But I think you’re talking about from a personal perspective. From a personal perspective, what’s happened is this opens a whole new class of problems/opportunities for me, largely around the fact that, yeah, to be blunt, we’ve got a lot more money. It was just the most first world problem to have because it’s making me think about responsibilities that I have, back to the community or to my family. It puts me in a position to have a much greater impact than I thought I could ever have, even just a year ago.

Nick Caldwell:
Earlier, I was talking about my desire and strong passion on leadership development. Well, now I’m in a position where maybe I can take some of my good fortune and reapply that to nonprofit efforts or more larger scale ways to develop leaders. I didn’t talk about this earlier, but one of the things I’m doing on the on the side now is my wife and I have started a nonprofit, which is focused on getting more people of color into technical executive leadership positions.

Nick Caldwell:
I guess even before that, I was spending increasing amounts of time with a nonprofit called /dev/color, which is around getting junior engineers of color into higher level positions within their company.

Nick Caldwell:
So starting to think a lot less about securing the bag and a lot more about legacy and what it means to help develop the next generation of leaders. And I think anyone who’s been given privilege, at least in part, has to think about how they can use that privilege to help lever up other people. So I spend a lot of time thinking about that right now. I don’t know if I have the right answer to it, but I certainly have an opportunity to make an impact in a way that goes well beyond building products, and into making it easier for the next generation of engineering leaders of color, making it easy for them to succeed. So I want to try and do that.

Nick Caldwell:
Where we’re getting moving on it. I aspire to make a difference here and I just feel fortunate to be in a position to be able to have this as a problem.

Maurice Cherry:
How did you get started on Looker?

Nick Caldwell:
It’s not too complicated. I was VP of engineering at Reddit and I had been there for a couple of years, and I was starting to think about what my next opportunity would be. As you know, in the Bay area, your typical tenure at any company is around two years. Startups move really quick. So I’d started to look around.

Nick Caldwell:
Looker, the CEO, a guy named Frank Bien, he needed someone to help them scale the product and engineering organizations. And then additionally Looker has what’s called business intelligence product. And I’m in my previous roles at Microsoft, I actually built one of the world’s dominant BI products.

Nick Caldwell:
So it was just very, very fortunate in terms of timing, it all came together. I was right in the mindset of exploring new opportunities, and Looker needed someone with almost my exact expertise to come in and help them scale up. So running product engineering design for a fast growing, modern approach to BI was just the right place at the right time.

Nick Caldwell:
I think three months after we joined, we started to think about potentially IPOing, and then eventually we got acquired. So I really chose the right horse to bet on.

Maurice Cherry:
What is the hardest part about what you do?

Nick Caldwell:
The hardest part about my job is that there’s a large number of what you call stakeholders. There’s a lot of people who depend on my organization to be successful. So if you think about what product and engineering do, we are trying to build the best possible product for our customers at any given moment. But how do we know what the best possible product to build is?

Nick Caldwell:
Well, we have to get inputs from all sorts of different sources. Existing customers, future customers, those customers can be differentiated by size, region, all sorts of different dimensions.

Nick Caldwell:
We have our customer support team who wants us to focus on existing the existing product and making sure that the known bugs are addressed rapidly. We’ve got input from our field sales teams, who we’re discovering new requirements and new functionality. And then, I shouldn’t leave out, it’s important to treat your engineering organization as a customer as well. So they want us to, of course invest in better developer productivity tools, paying down technical debt, innovation projects that they may have discovered.

Nick Caldwell:
All of this is the challenge. And synthesizing all of this is the challenge. And it’s my role to build an organization that can take all of this input, translate it into the best possible product roadmap or set of investments that we need to make as an organization. And not just the roadmap, but we didn’t have to go and build the organization, hire the right people, make sure that we have the right managers and line everyone up. All the skills that we have at our disposal are lined up to best meet these very, very difficult product challenges.

Nick Caldwell:
So in a nutshell, synthesizing all of that is the toughest part of my job because there’s so many inputs, they change all the time. And the thing that we do to meet this demand is we build an organization. That organization is constructed with people, and every person has different motivations, things that they want to accomplish with their careers, different things that excite them and things that they want to learn. All of that has to come together in the right way for us to build a successfully operating product organization. So it’s complicated.

Maurice Cherry:
I can imagine, first of all, I think just with the acquisition, that changes the game for every single person that works at Looker because now you are part of this much larger, much more well known company. Of course there’s more money, but then there’s also, I would imagine like a merging of cultures, that probably come into play. Is that right?

Nick Caldwell:
Yeah. We haven’t merged yet. We’re still waiting to integrate, but it’s one of the things that we do talk about as a potential concern. But the nice thing about the Looker plus Google union is we see a lot of good cultural overlap.

Nick Caldwell:
Looker’s headquarters is in Santa Cruz, so we want to make sure we don’t want to lose that. I don’t know if you’ve ever been to Santa Cruz, but Santa Cruz is kind of a beach town. It’s a very laid back and chilled place. We don’t want to lose that kind of cultural element that makes Looker feel relaxed and so forth.

Nick Caldwell:
At the same time, we’re pretty excited about, I don’t want to say Google propeller hatism, but they do give out propeller head hats to every new employee. But there’s a certain amount of excitement that we have around the Google technical culture and how we can integrate some of their more forward looking products, like BigQuery and so forth. How we can more directly work with those products and integrate them into Looker’s product roadmap?

Nick Caldwell:
So we’re pretty excited about it. From a culture perspective, I think we have a really solid understanding of what makes Looker great and successful, and then we want to take the best of that and bring it with us to Google.

Maurice Cherry:
Very nice. So you mentioned being a boy from PG County. What was it like growing up there?

Nick Caldwell:
I don’t know if your audience knows where PG County is. PG County is in Maryland-

Maurice Cherry:
It’s black people. They know.

Nick Caldwell:
Awesome. Yeah, PG County is like 95, 98% black County in the Southeast of DC. Growing up there, on the one hand it’s super comforting. You’re in the community. It feels very welcoming in that sense.

Nick Caldwell:
But I think the downside of that is … What’s a way to put it? Opportunities are not equally distributed. Talent, I think, and potential is equally distributed. But opportunities are not equal distributed. So, if you grew up on the East coast or in Maryland, I think if you’re going to stay in that area, you’re largely going to be thinking about government jobs, things of that nature. I kind of very early on in life realized tech would be a great way to go, if you wanted to think about A, being a part of forward looking trends, and B, making money.

Nick Caldwell:
I very early on tried to think of ways that I could achieve these goals, and it became clear to me that, because opportunities are not equally distributed, that I would have to find a way to get out of PG County and go somewhere else, if I wanted to achieve my maximum potential. And I think I realized that pretty early on. I can’t remember the exact moment, but it’s something that is kind of born out to be true.

Nick Caldwell:
When I wanted to get the best possible education to set myself up for future success, I realized that it wasn’t going to be University of Maryland or UNBC, it was going to be, I’m going to try to swing from the fences, and I really wanted to get into a school like MIT or Harvard. Early on, I decided that was going to be the goal.

Nick Caldwell:
And then from there, it kind of followed. I just kept setting this kind of personal mission to go wherever the best opportunities were, and try and take the best advantage of them. And that’s played out for, I guess most of my life.

Maurice Cherry:
Sounds like tech was maybe like a big part of your growing up, like you were exposed to it at an early age. Is that correct?

Nick Caldwell:
Yeah. I think when I was a, I must have been a toddler. I was like three, four-ish. My dad brought home a Tandy 1000. These were one of the very earliest types of computer. And my dad was doing casework. He was a a lawyer and he went from doing that on paper by hand to Tandy 1000 personal computer. So I used to sit on his lap and he would let me kind of punch into the keyboard. I’m surprised I didn’t break anything.

Nick Caldwell:
But yeah, he got me kind of early games to play on it. And over time, I just got fascinated with this thing. By the time I was aged 10, I was for sure hooked on video games. I was playing PC games. And he bought me a book called Learn C Plus Plus in 12 Easy Lessons. Which was a lie, you can’t learn C Plus Plus in 12 easy lessons.

Nick Caldwell:
And I really just dug into that. I decided that, that was going to be the thing I spent my summer learning. And by the end of the summer, I’d taught myself C Plus Plus and I used that knowledge to start my own bulletin board system. I don’t know if you remember these things, but pre-internet, you could set up your own little bulletin board systems and start your own community.

Nick Caldwell:
And I started coding extensions for that, like little video games and things like that. I was already hooked and I started to see, as a part of doing this bulletin board system that the world was so much bigger than PG County. People from across the country would like call into this bulletin board system, leave messages on it or upload files. And it gave me an opportunity to talk to people from different walks of life and different age groups, different jobs. It was kind of like I got early access to all of the potential that the internet could have. And the key realization to all this, to me was like, this is going to be a huge later on. I should learn as much as I can about how to code so I can be a part of it.

Nick Caldwell:
Unfortunately, I dropped all my other hobbies. So, I went from like your typical eighties kid, playing outside every day, riding your bike around the neighborhood. I went from doing all that to just coding and working on software plugins almost instantly.

Nick Caldwell:
So, I just immediately fell in love with it. There’s just something cool about, you write software and you know, you hit run on it and the computer is doing something like in a program fashion that you told it to do that. It’s just always been fascinating.

Nick Caldwell:
And the other thing which is really important, this sparked a desire to me. I really started to get hardcore academic at this point in my life. And so it wasn’t just fascination with computers, it led to better academics. It led to me going to another school in Maryland which had better a computer science program, which ultimately ended up leading me to go to MIT.

Nick Caldwell:
So it had kind of a very foundational role in my life. Being so excited about computers at this early age set me up with a great foundation for future career.

Maurice Cherry:
Wow. Did you have your family support you in all of this? Because I would imagine starting out with this, and I guess I might be projecting a little bit, because this sounds so similar to me growing up.

Nick Caldwell:
Yeah.

Maurice Cherry:
we didn’t have a Tandy 1000, my older brother had he had a Vtech Laser 50 computer. It was sort of like the size of a standard 10 key keyboard now. It has a one line dot matrix screen on it, and you could basically program. And I learned basic. In the library, they only had one computer book and it was on basic. I need to find that book. But it was like a green book that taught you how to program in basic. And the Laser 50 came with all these little peripherals like a cassette, like a disc drive, but it’s a cassette, you know?

Nick Caldwell:
Yeah.

Maurice Cherry:
It had a little tiny dot matrix printer that you could expand memory and do all this sort of stuff with it.

Maurice Cherry:
And I remember just learning how to code on basic with that thing, and then graduating from that to like the Apple 2E in school. We were learning how to do that and work with doss and all that sort of stuff.

Maurice Cherry:
My mom probably hated it. She wanted me to be doing other stuff, like getting out there and, “Oh, you should be going outside”, like you say, riding bikes and stuff like that.

Maurice Cherry:
And I was like, “No, I want to program. I want to go to the computer lab”. How was your family? Would they support you in all this?

Nick Caldwell:
It was odd. My family is great in the sense that they tried to expose me to a lot of different things. My dad, jazz music, chess club, painting. They would encourage me to do all sorts of things. And programming was one where it was so clear and that it stuck with me, that I really wanted to stay with it, because I dropped all these other hobbies.

Nick Caldwell:
So they actually leaned into it with me. I think what I remember is once I expressed that I was interested in it, not only did my dad continue to take me to the bookstore … The first book I got was learn C Plus Plus. I think the next book I got, which was stunning to me at the time, it was like a $250 book on how to code video games. So that was the second or third programming book I ever bought. So I was learning how to do assembly language within about four or five months of deciding that this was interesting. And my dad was putting a lot of money into it. I was like, “Wow, 250 bucks”. Oh, and also my mother like found out-

Nick Caldwell:
I think part of this was… Oh and also my mother found summer programs for me to go to where you could…A part of it would be like coding camps and things like that.

Maurice Cherry:
Mm-hmm (affirmative).

Nick Caldwell:
And to get to those things, they were not in PeeGee County. We had to drive like two counties over to participate in those things. I was fortunate that they A. recognized that I was excited about this and they were willing to tolerate my near total fixation on it. So I was really fortunate in that. But yeah, I did have a few times where my mom did show up and just kicked me out of the house and saying: Hey you need to go stop staring at the screen and go biking. That did happen one or two times, but largely speaking, they were super supportive.

Maurice Cherry:
Let’s talk about MIT. You went there for undergrad. What was it like there?

Nick Caldwell:
MIT is pretty brutal. I actually, to be honest, I don’t recommend most people go to it. People ask me about that a lot now because I think MIT has a great reputation as a school. You will learn a lot, you will learn how to work. It is an extremely difficult school though. And for me, it was kind of doubly difficult because it’s not a very diverse school. So I was coming from PeeGee County, Maryland, which again PeeGee, my hometown is like 95% Black. Boston is none of that. Cambridge is none of that. So it was honestly like a major whiplash for me. To go up there and kind of be isolated from the community and then simultaneously… Like No one goes to MIT… When you were in high school, in order to get into MIT, you have to be pretty smart. So I was like yeah, I was a pretty smart guy in high school. You know, you build up a little bit of ego and so forth that lasts maybe three hours into MIT. I’m not exaggerating.

Nick Caldwell:
I remember the first day at MIT, they pair you up with the other first year students, right? You’d go out to lunch with them and things like that. So the first few hours of my MIT experience was: I went to go hang out with my group and when I sit down at the lunch table and I’m waiting for people show up. A little kid shows up. He sits down and a few other people show up. And we were all are kind of wondering why the little kid was there. So we asked him, Oh Hey, is your brother here or are you waiting for somebody? He was like, Oh no, I’m a first year too. I’m like, Dude, how old are you? He’s like, Oh I am 12. [crosstalk 00:24:20] That’s when it kind of hits you that like no matter how smart you think you, you weren’t, here’s a 12 year old who is probably a genius. He ended up being… A Few years later, he was teaching one of the classes and it was wild. It really forces you into a different mindset, which is no longer can kind of coast through any challenges. The challenges are going to be really hard and it gets you into a kind of a mentality that whatever life throws at you, you’ll have to come up with a plan and work your way through it.

Nick Caldwell:
So in that sense, MIT was formative for me. There’s really not been any challenge that I’ve faced professionally that has come close to what I dealt with as a black student, going to MIT, going from PeeGee County to Boston and then putting up with that very, very rigorous difficult curriculum. But at the same time it just set me up to be able to take on any sort of challenge. If you look at my career after that, I mean I take big swings at things and largely speaking of have been able to pick my way through and find success. So I’ll stop there.

Nick Caldwell:
So how did the NASA internship come up?

Nick Caldwell:
Oh, that’s funny that you mentioned that. So, like I was saying earlier in Maryland, you know a large number of people out there end up working at government institutes. So when I was in high school, because I could code, I had and because I had good academic record, we had the opportunity to do kind of an intern program as part of our high school curriculum. So I think this was junior year, I was able to take time off of regular school and go work with a governmental institution. I’ve loved the space program since a young age. I mean I think anyone from our generation probably would tell you how fascinating to watch shuttle launches and stuff. It used to be a huge deal.

Nick Caldwell:
So when the opportunity came around, it was like NASA or NSA or the FDA. I think those are the three ones that I could go to. And of course I jumped at NASA. I ended up working there as an intern for three years and working on satellite parts. Now the problem with working at a government institution like NASA is it takes a long time for that stuff to ship. Nowadays, if you’re in tech like people complain about like, Oh, don’t do waterfall. What they think waterfall is. It takes like three months to plan something that’s nothing at NASA. I mean I was there for three years working on this satellite, high energy solar spectral imager. I believe it didn’t actually launch until three years later and then it exploded when it launched. They had to redo it. So I think the from a total project length, I think it was more than eight to 10 years. So I really enjoyed being exposed to that early on because one, again, I got to learn more coding. When I was at NASA, I got to do a combination of Visual Basic, Assembly. I got to learn very how to code for very specialized pieces of hardware, which was really fun. But it also taught me that working in a government Institute was not what I wanted to do for my career. I like to be entrepreneurial. I have to be fast paced and thought to myself like maybe the answer to that, what I really want to do isn’t at this NASA job no matter how cool I thought it would be, I’ve got to keep looking. So that kind of planted the early seeds of I want to do something entrepreneurial. Like I didn’t get to sow those seeds for a very long time, but that’s kind of where it started.

Maurice Cherry:
Just hear you talk about this. I’m trying not to make these parallels myself. but like, so this is probably about, I don’t know, maybe 11th or 12th grade. I just wanted to like get out of my small, so I’m from Alabama, I’m from Selma, Alabama. And it’s funny you mentioned that about like spacing growing up because space camps in Alabama, it’s in Huntsville because we have a, Oh sorry. We have an nice facility and normal, which is near Huntsville where the space camp is and so never got to go to space camp. But space was always something that was kind of around, I felt like based on where I was going in terms of my education, like working for the government was going to kind of be the goal. So right around 11th or 12th grade I was really looking at like what are places that I would like want to intern and work at. NASA was one of them, CIA and FBI or what I was looking at like I want it to be a clandestine service agent.

Maurice Cherry:
I laugh at it now, but because I was good in math and it was sort of the thing that my, one of my teachers was trying to push me into, like you can really do this and you know, that sort of stuff.

Nick Caldwell:
yeah.

Maurice Cherry:
And so you mentioned The Challenger and I’m actually a Ronald McNair scholar, Ronald McNair, one of the astronauts on Challenger. And so that’s how I ended up going to Morehouse. I got a McNair scholarship and then that’s sort of fed into the NASA internship. The program that we worked on. The first year I interned, I was at aims, which is out in Moffett field, which is a near mountain view kind of South of San Francisco in the Bay. And I worked on these a Sofia projects, it’s a seven 47 that they cut a hole in on the side and they put in a huge like gyroscopic telescope.

Maurice Cherry:
Sofia stands for a stratospheric observatory for infrared astronomy. So the plane like orbits the earth and like observes like magnetic fields and comets and all that sort of stuff. And so my internship was with Ames at the SOFIA Science Center. We were doing stuff like that. We were working with robotics. It was so cool. It was the coolest shit I have ever done in life. I kid you not. And I was also working with like HTML and stuff. Like I got the program, the robotics education homepage and we were teaching K through 12 students how to do programming with robotics using Lego Mindstorm kits. I’m like, this is the coolest shit ever done ever. And I go back to school and you know, studying and whatnot. And then my next internship was at Marshall Space flight Center in Huntsville and I was doing something a little different. I was working more with human… What was it called?

Nick Caldwell:
A human computer.

Maurice Cherry:
No human factors engineering. Oh that was where I saw like my first 3D printer. That was where I saw… Cause like they 3D prints nose the cone on the space shuttle because it burns up on reentry. So they use this, this hexagonal like printing filament called Markcore. And like they print out, they showed me how they print out the nose cone and so I got to work with like human factors engineering and stuff like that. Still is some of the coolest shit I had ever done and I really want it to continue on that path. And then 911 happened and they pulled, the government pulled the funding for my scholarship program and I was like fuck. I don’t have anything else lined up? So I’m curious though, when you talked about like the entrepreneurial thing, once you graduated from MIT, like what was your next step?

Nick Caldwell:
I had a lot of students debt. So I want to start with this. Cause a lot of people ask me specifically like, Hey man, if you graduate from MIT, you should have gone to work for Google or Facebook. So I want to frame the timing of my graduation. Put it all in context. Google. I mean they were basically still a startup when I graduated. Facebook did not even exist or Mark Zuckerberg was still at Harvard and I had huge amounts of student debt. I really wanted to A. Be intact. The be finds the shortest possible path to like a successful, lucrative tech job. I want to pay back those loans, set myself up for success. Maybe go back to my hometown and be the big hero, help my mom pay some bills or something like that. Microsoft at that time was the biggest tech company and I decided I wanted to work there. They had a group called the natural interactive services division. It’s just a fancy way of saying they work on machine learning and natural language processing, which I had become like fascinated with during my time at MIT. I was doing machine learning on during an era when it was definitely not considered cool. I remember my advisor actually told me not to pursue machine learning is that it was a dead end. You know, it took a while.

Maurice Cherry:
My advisor told me the same thing about the web. He said it was a fad. If you want to study this, you should change your major. So I did. Cause I started out computer science and changed the math.

Nick Caldwell:
Who is going to do this HTML stuff? I mean I ended up choosing Microsoft and it wasn’t an entrepreneurial decision. I think during my time at Microsoft I tried to bend the experience that way. I’ve joined teams that did lots of internal kind of new projects and new startups. I tried to find ways to express my passion for doing new things with new technology and taking on those big sorts of challenges within the broader ecosystem of Microsoft, which was obviously a very well established business. But if you, trace my career through there, started in a team that was doing like very, very forward looking [inaudible 00:33:58] and NLP tech and then they carry through to to multiple different other teams and was able to carve out like a very successful career.

Maurice Cherry:
Nice and you were there for a long time?

Nick Caldwell:
Yes.

Maurice Cherry:
15 years over 15 years. A little over 15 years.

Nick Caldwell:
I like the emphasis you put on that. Like a long wow time.

Maurice Cherry:
It is a long time. You started in what, like 2004, 2005 or something like that?

Nick Caldwell:
My first internship there was 2001 I think.

Maurice Cherry:
That’s a long time.

Nick Caldwell:
Yeah, man.

Maurice Cherry:
Well I mean I say that because you know, of course the industry has changed so much from year to year. I mean even if you think of those early times in the 2000s to now. It’s like night and day. And to be at the same place, especially a company like Microsoft that we know where Microsoft’s reputation was back then and then of course it, I don’t want to say it’s gotten maligned, but I would say like between like 06 and 2013 people were like: Yeah, we’ll look at Apple. Now Microsoft has started to sort of have this great resurge. It’s not just the gaming but like also with Windows 10 and with you know, devices and stuff like that. So to be at a company that long and to see it through all of that, that’s a rarity in this industry.

Nick Caldwell:
Let me shortcut, because I know we want to give people advice. I mean I definitely tell people not to stay at one place for 15 years nowadays. But in my defense I was just having a really good time. Externally Microsoft was dealing with all of these sort of challenges with governmental regulation and so forth, but for me in my role, like I was just popping between really, really fun projects. My first project was I got to own the spellchecker for all the Microsoft products. That thing shipped to more than a billion people. I mean like impact, right. You know, then I got to do a bunch of machine learning and NLP projects as a part of Microsoft exchange and SharePoint like one of the cool things about it was you could ship something and it could go out to you know, millions and millions and millions of people and you could really have big impact.

Nick Caldwell:
And Microsoft also has something that early on to be blunted it had a very safe sort of understandable career path. Like you know, any big company that got like really well established job ladders and you can kind of like, particularly if you’re a video gamer that’s like, Oh, a ladder goals, achievements, I’m going to play that game and see how far up I can get it. So at Microsoft the game is like everyone wants to work their way up to a ladder level called partner. Right? So a partner is like considered you I guess you win the career game. So I, for a large part of my career I had this mentality that like your career was directly tied to your job title or the number of people who report it to you. And I had gotten into this mindset and you know in a big company like Microsoft, they actually do set it up so that you can if you value success in that way you can drive career in that way.

Nick Caldwell:
And I was doing like doing that quite well. I ended up becoming a general manager at Microsoft, I think after 12 years. I hit that partner goal after around 12 years, which if for folks who work at Microsoft, like going from like new employee to partner or general manager and 12 years is extremely rapid pace. I think the only person I’m aware of who did it faster was a guy named Scott Guffey who’s currently the senior vice president of all of Azure. So I was having a really good time. It was long story short and I got to work on a product called power BI ended up being like the fastest growing Microsoft product in 2016 so I was having an amazing time, but I did kind of eventually realize that although I was having a great time working on new products inside a big company is not actually entrepreneurship.

Nick Caldwell:
I started to slowly realize this over time. Part of it was when I was getting toward the, I guess the last, the final few years of my career at Microsoft, I had decided to go get an MBA cause I love formal education. It’s just the way that I like to absorb content and learn. Formal education forces you to be in a place and a time to learn things. And sometimes I need that discipline if I want to learn. So I decided to get an MBA and I decided I wanted to learn about entrepreneurship. So I started to fly down to Berkeley Haas school of business on the weekends to take my MBA classes and I started to get exposed to people outside of the Microsoft bubble outside of the Seattle bubble. People who were could tell me about all of the cool things that were happening in Silicon Valley.

Nick Caldwell:
And I was like, Oh wow. Like I used to not take this part of the world as seriously as I should have because I thought like, Hey, Microsoft is shaped can’t it company and you know, I can spend my whole career here and be happy. But as I started to get exposed to all these other people and companies and ideas, I realized just so much more opportunity out there if I’m willing to take on a little bit more risk and get a little bit more uncomfortable and maybe trap, pursue a career that isn’t just popping up job ladders and has maybe about taking a few horizontal moves or maybe have a smaller team with bigger impact because you know what I can deliver to the company matters more. So I started to think about my role in companies and how I want him to navigate my career radically differently.

Nick Caldwell:
After that, that MBA, and then I think within six months of graduating the MBA, I had a meeting with my corporate vice president at Microsoft and was like, Hey, I think it’s, I think it’s time for me to go. I want to go, I want to go really be part of this startup ecosystem. And he’s like, where are you going to go? And I was like, well my, my friend works at Reddit and he says they’re looking for a VP of engineering guy like laughed in my face. It’s like, you’re going to go to Reddit. What’s that? So, but I really wanted to, I mean I think at that time Reddit was a series B startup. They really needed someone to help them scale the engineering team. And I was like, I’ve done this before. I’ve worked at, I’ve run big teams at Microsoft. I’d bet my skillset would be really, really valuable to this team. I bet I could have a huge impact, even though it’s a smaller team, that the impact that I could have would be much, much bigger in effect, all of the Reddit global audience, which is hundreds of millions of people. So I started to get really excited about that.

Maurice Cherry:
And I mean you….You kind of joined Reddit in 2016 right? Like latest 2016.

Nick Caldwell:
Yeah.

Maurice Cherry:
This was at a time when like the company maybe didn’t have the best reputation.

Nick Caldwell:
I mean you’ve said it very politely. Yes.

Maurice Cherry:
I mean to put it in context with people who are listening. This is near the time Trump got elected and there was a lot of stuff going on around Reddit in terms of just violent hate speech and things of that nature. Did you think about these things when you thought about going to Reddit or were you just kind of strictly looking at like, this is a startup, I want to do something more entrepreneurial. This is a good place to go for that?

Nick Caldwell:
No, I did consider it because, going back to what I said earlier I early on in my tech career, if you will, I was running bulletin board systems. So I understand the challenges that come with building online communities. It’s just something, I was doing pre-internet. So when I looked at what the challenges are with Reddit, sorry, I kind of looked at that more like, I see the value here and the reason that they’re trying to hire me is because they also recognize these problems and they need someone to help. And the pieces that I can help with have to do more with engineering and so forth. But alongside me, they were hiring all new product people. They were gearing up to really take this sort of challenge seriously. I don’t know if you recall this, but the first week I had the job at Reddit, we actually went to a conference, excuse me, we went to the exec team, all went together to a conference called tech inclusion.

Nick Caldwell:
It’s a conference that used to be run by Wayne Sutton.

Maurice Cherry:
Wayne Sutton, yes I know Wayne.

Nick Caldwell:
Yeah. No he is an awesome dude. But the very first week we were there, the whole exact team went and did an hour long, let’s talk about how Reddit is going to address problems on the site, including things like hate speech, including like wanting more diversity on the platform. So we were taking it really head on. So I knew all those problems were there, but in all of my interaction with the exact team, all I got was like the authentic desire to try and, make things better. It was like, well I can be a part of solving that. It was super fun. I mean that whole experience, I mean getting to scale their engineering team, getting to, I think you would agree that the reputation of the site is now a lot different in the sense that they have invested heavily and cleaning up a lot of the toxic communities and the infrastructure for doing that as alignment to scale more rapidly. You know, I feel really about the work that the team did there as well as the culture that we built inside the company. I mean we had one of the most diverse I probably the most, actually I’ll make a stronger claim. That was the most diverse company I’ve gotten to work at in my professional career. I was really proud of being a part of building that.

Speaker 1:
When you look at your career now, you look back at it, currently at Looker, slash Google, Reddit, Microsoft, etc. What is Silicon Valley like for you at this stage in your career?

Nick Caldwell:
At this stage in my career, Silicon Valley is just unlimited opportunity. I wished I had moved out here sooner. Silicon Valley, it is interesting the more… I’ve only been here three years if you just wall clock time.

Speaker 1:
Okay.

Nick Caldwell:
So I’m still learning about all of the different facets of how Silicon Valley works. And I’m by no means an expert. But one thing I have realized over the past, year or two, is that there is more opportunity and more money to fund ideas here than in any part of the world by far. It is an engine for connecting investment capital with bright, ambitious people. Now that’s all fine and good. The negative side of that, the thing that.

Nick Caldwell:
Now, that’s all fine and good. The negative side of that, the thing that as a person from P.G. County that I’m starting to realize is that, the opportunities are not equally distributed. So, although this is a place that is just phenomenal, there’s no better place in the world for investment, changing the future, yadda, yadda, yadaa, that opportunity is not available as equitably as it should be. And I’m trying to find ways to help with that problem. Part of it is, can we find ways to get more underrepresented people; people of color into tech positions. So, I do see a lot of progress on that dimension here in the Bay area. There’s so many bootcamps’ and if you talk to startups in increasingly large companies, they’re seeking out new ways to bring diverse candidates into the top of their hiring funnels.

Nick Caldwell:
I see a lot of progress happening there. But, I still think that much of the wealth opportunity sits high in higher levels of career growth. Right? So, executive levels in particular. So, one thing that I’m spending a lot of time on now is trying to think through, how do we get people who are in middle or late career, people of color into executive roles. One thing I guess you didn’t ask me about Reddit was how do I even discover that opportunity? Access to executive recruiting networks, is something that I had discov- to discover effectively through word of mouth. I kind of got lucky. If I hadn’t had that luck, I don’t know if I would have ever been able to leave Microsoft, get introduced to the right people and start exploring different executive opportunities. So I’m going to try and make that easier for the next generation.

Nick Caldwell:
I think that having access to the right people, in the right network, is one of the largest inhibitors for people of color, to get to the next level of growth. And I want to try and invest in creating those networks. So next, I think I told you this, but next week I’m actually going to host an event where we connect. I invited a little more than a hundred people of color, mid and late career, who want to learn about how to get into tech exec roles. We’re going to have them and then we’re going to have a panel with more than six different executive recruiters and people of color who have made it into exec. roles and just talk about the paths and the right ways to network, the right ways to position yourself for those opportunities. How the interviews work differently than normal tech interviews.

Nick Caldwell:
I just want to spread that knowledge, as far and wide as I can into the community, to make it easier for the next, the next generation. Cause for me I had to discover all this stuff the hard way. I don’t think it needs to be that hard if we just share information.

Maurice Cherry:
Yeah. How do you define success now?

Nick Caldwell:
Early on I defined success as, trying to make money. You know, I’ve talked about that student loan thing. The middle of my career, I think I defined success is as, having freedom; the ability to work where I show wanted to on the projects that I wanted to with the people that I wanted to. And then, I think now, I’m switching into a mode where I define success as legacy. What am I leaving behind, and will I be remembered for having made an important difference, not just from a product perspective cause products come and go, but will I leave a positive impression on the next generation of, of people of color in tech? I think that’s where I’m landing, so I’ll, I’ll stop there.

Maurice Cherry:
Okay. How do you sort of navigate the expectations that others might have about you? I would imagine, being at this stage in your career, and you’re doing all of this kind of outreach to the community, like you’re saying… How do you manage those expectations that folks have?

Nick Caldwell:
Yeah, I was going to say, what do you mean? Is this a trick question? Did you have some expectations?

Maurice Cherry:
No… Do I have any expectations?

Nick Caldwell:
I’m curious what you know.

Maurice Cherry:
I mean look, I’ve talked to a lot of people on this show, right? I never know how people are going to react. Some people I will ask and they’re like, I don’t want to talk about x, y, z. I don’t want to be classified, as a black blank, you know, whatever their title is or what have you. I was just curious because I know I’ve talked to people that are at, you know, sort of different levels of their career. Certainly ones that are at very high levels, and it seems like from the larger community, there’s a big expectation of, I don’t know whether it’s benevolence of helping out or reaching out, reaching out or reaching back or what have you. Are those things that you even think about?

Nick Caldwell:
I don’t think the larger community puts this sort of expectation or pressure on me. It’s something that’s like intrinsic to me. I’ve been a manager for a long time. I think, I could claim I was pretty good one. And one thing that I think makes for good managers is you, you care about other people. That the best managers I’ve ever worked for, have tried to understand where I’m trying to go with my career and my life and they’re trying to line up the right opportunities, and the intersection of that is kind of the sweet spot. My personal goals and desires line up with what the business wants. We end up in the best possible place. So for me as a person who’s been doing that for a long time, as a lifelong manager, it’s just something that comes natural.

Nick Caldwell:
I really want to try and lift up others. So I look for opportunities to do that, and I get a lot of satisfaction out of it. But the community itself, it doesn’t, it’s not like people are kicking my door and I’m like, “Hey Nick, like because you’re in this position, you’ve got to give back”. That hasn’t happened. It’s really just more of a natural outcoming for the things that I want to do. And I, I feel like I’m very privileged in the sense that, I have access to knowledge, experiences and networks that I can make it more easily available to, to the next generation. So I guess that’s my answer. I don’t feel pressure for it. I get a lot of satisfaction out of it.

Maurice Cherry:
Okay. All right. If you could go back and talk to young Nick, like fresh out of MIT degree, what advice would you give him?

Nick Caldwell:
Young Nick, was not the Nick you’re talking to now. I have a lot of, takes a while to recover from MIT. So I guess the first, the first thing I would say is MIT related, which is, I graduated thinking technology, could solve all problems and technology is amazing, but it turns out people solve all problems and you can’t code your way to success. It’s a combination of code, working with people, and that is how you solve problems. So I would say, young Nick, spend more time understanding how the broader business you’re in works beyond development. Talk to PMs, talk to the testers, talk to sales, marketing, talk to all the people that it takes to bring an organization together, to build something. And it’s not just coding. I think chart your own course. I think, I learned this a couple of years in, but the best opportunities just don’t show up.

Nick Caldwell:
The best opportunities come from, you being proactive and sometimes that means you just going out into the organization and saying, “Hey, is there any place I can help,” or “What are the big initiatives and where should I try and plug in?”. Sometimes it comes from, it does come from luck, but that luck, at least in my experience, is a result of having delivered good product and done good work and network. Right? So I would tell my young self,”Spend more time, trying to, create the environment where good opportunities will come to you; not just doing good work and expecting your manager to reward you for it. But networking and understanding the broader business context so that you could, so you can understand where your time should just be spent”.

Nick Caldwell:
Actually, let me talk about one that’s probably the most important because you were making fun of me for working at Microsoft for 15 years. That’s probably the biggest thing I would say, which is, a lot of people talk about “Imposter Syndrome”. Imposter syndrome is like, “Hey, you know, I’m doing really good at, at my job, but I don’t believe I’m doing it. Like I lack of self confidence maybe I feel like I’m faking it”. So I hear a lot of people talk about imposter syndrome, but I think there’s like a bigger problem that affects people of color, underrepresented folks. And that’s what I call, “Just happy to be here syndrome” which is, for the longest time coming from P.G. County and going and having your first job be like a six figure paycheck. Right. That’s a pretty big freaking difference. That’s a big Delta. So for many, many years of my career I was like, well I’m just happy to be here because I’m making this amount of money and my alternative would be going back to P.G. county or something like that. I had that in my head. Just happened to be here.

Nick Caldwell:
So, no matter what my bosses would ask me for if they wanted me to come over the weekend, something in the back of my head was saying, you, you’re just fortunate to be even in this situation. And I didn’t realize until far too late, that you don’t have to just be happy to be there. It’s the fact that you’ve made it into tech and that you’ve had any success, your knowledge, skills and abilities are what you have to offer and they have their own intrinsic value and that is what your managers and your company is rewarding you for. So they should be happy to have you. If you show in any sort of skill and results, increasingly, your company should be happy to have you.

Nick Caldwell:
I think that holds a lot of people back, who are under-represented. They maybe had a big transformation in their lives, going from, where, for me it was P.G. County to Seattle and making so much more money, making more money than anyone in my family had made. But, what that blinds you from is, particularly in tech, if you’re always just happy to be here, you’re going to be blinded to all of the new opportunities that are around you. And in tech, as far as I can tell, there’s no ceiling. There’s no job I’ve gotten in tech where I didn’t like pop my head up, look around for five minutes and there wasn’t even a bigger opportunity just right over the hill. Even today, I’m chief product officer at a multibillion dollar company that just got acquired and I can tell you, there’s much, much bigger things out there that I could even be doing it.

Nick Caldwell:
There’s no end to it in tech. There’s so much opportunity. But, when I talk to people like myself, I suffered through this as well, who are new to their careers and they’re maybe not as confident of themselves or understand that they have this intrinsic value. They will pass up opportunities or, or let fear dictate like what their decisions are, and they will just be happy to have gotten the job at all. And I think the faster you can kind of get self confidence and get out of the mentality, the more you can control your own destiny, start making your own career decisions and really navigating all of the opportunities that are sitting here in tech, because they’re enormous. It’s much for the person who’s listening to this, and you just landed your first six figure job, the opportunities to go beyond that, are there. You can do much better. I, trust me, so don’t get locked into this, “Just happy to be here syndrome”.

Maurice Cherry:
Wow, that’s powerful. I really, I really, really liked that message. What’s something that you’re really proud of that’s not on your resume?

Nick Caldwell:
This is not explicitly on my resume and I, and the reason I can’t talk about it publicly is because we’re not supposed to share these sorts of impact numbers publicly, but when I was at Reddit, one of the things I was most proud of, I alluded to it earlier, was the impact that we had on our diversity in the engineering organization. We moved the number of women in engineering, the number of people of color in engineering there by double digit figures in a very, very short amount of time. So, for me being able to have that sort of tangible impact,, at a place that like has a reputation like I don’t know, you know Reddit has a reputation for not being the most diverse website, at least it did at the time I joined. But being able to come in and have that kind of sort of substantial impact, move the numbers in a real way, not just platitudes, and do it fairly quickly felt really, really good.

Nick Caldwell:
It’s not something we’d get to talk about in public a lot because I think Reddit has a policy about sharing the specifics on the diversity numbers, but they’re quite good internally. I think the, on a related note, many of the people that worked for me at Reddit and many of the people who I mentor during that timeframe, have since gone on to get executive level jobs. I guess the thing I am very proud of at this stage of my life, is just seeing that my time and energy that I put into people, allows them to get to the next level and achieve whatever goals that they have in mind. That, I am broadly speaking proud when that occurs. I know it’s an odd way to be selfish, but I guess selfishly, I like to know that I helped other people. I guess that’s a way to put it.

Maurice Cherry:
Where do you see yourself in the next five years? It’s 2025, what are you working on?

Nick Caldwell:
I think, I’m going to be at Google for a while. We just got acquired, so I mean I, I’m excited about what we’re going to do with Looker plus Google. So I think for a product perspective that is pretty straight forward. But I think my ambitions are increasingly, expanding beyond product. I think, there’s kind of two other avenues that I’m exploring now. By the way, my wife also, is at Slacks and we both had startup exits last year. Silicon Valley standard for having a startup exit as you start to look at angel investing and you start to think about venture capital. So on one angle of what I’d like to see myself doing in five years is, I would like to have been first check to several startups founded by black starters that have, well black founders that have successfully exited. So over the last year, I think I wrote three checks to black founders last year. So, hopefully in five years we’ll see them being successful. Shout out to Morocco. I love you guys.

Nick Caldwell:
The second thing that I’m thinking a lot about is how we can contribute to the next generation of people of color in leadership positions. So, I’ve been working on training programs and opportunities to try and give the next generation of exec talent, access to the same sort of things I was fortunate to have, that really set me a part of my career. So I was at Microsoft, I got access to proto executive training and it also had lots of training on it through my MBA program.

Nick Caldwell:
I’d like to see if there’s ways we can make those sorts of trainings accessible to the next generation of executive leaders, because to be blunt, not everyone should have to go through the level of difficulty that it took me to get those opportunities. I want to shorten the gap between the very, very large and existent, up and coming generation of potential leaders. I want to shorten the gap between them and available opportunities and I think that’s going to come through training and networking and just shining a light on the fact that there are all these folks who are just on deck, ready to take a swing.

Maurice Cherry:
Where can our audience find out more about you and about your work and everything online?

Nick Caldwell:
Yeah. If you want to follow me on Twitter, I think that’s the way most people find me nowadays. So follow me @Nickcald, Nickcald. If you’re interested in learning about engineering management or product philosophy, I’ve got a ton of stuff that I’ve been writing on medium so you can just Google that and otherwise I don’t. Don’t be shy. If you would like some advice. A lot of people just reach out to me on LinkedIn. I respond to almost everything, but I know a lot of people want to get coffee so I’ll tell you right now so I can’t have that much coffee. Like man, I would be wired nonstop, but I will always, always, if you, if you write me a thoughtful question, 99% of the time I take the time out of my day and try and give you an answer. So those are all the ways you can reach me.

Maurice Cherry:
Awesome. Well Nick Caldwell, I want to thank you so much for coming on the show. I really had, no idea how this conversation would go. I knew that as I was doing my research, I was like, “Oh we have some things in common”. Like, I interned at NASA. I was looking at the time. I’m like, I felt like we were kind of right, doing things like right at the same timeframes and everything.

Maurice Cherry:
But, hearing you talk about not just you interning at NASA, but the work that you’ve done with Microsoft, the work you’re currently doing at Looker, and really how you look at giving back to the community, in ways that I think will help set up the next generation of tech executives etc. I think is something which hopefully our audience can and learn from and get inspired by, to see ways that they can create a more equitable future. A theme that I’m running with for the year, how do we use our talents and basically the places where we’re at to kind of make a better future. And I feel like you’re doing it. Like you’re, you’re doing it, you’re making it happen.

Nick Caldwell:
I’m trying man. I actually know that you mentioned this. I’ll just put one more thing out there cause you asked, “What advice could you ask me? What advice could I give to a younger version of me?”. I want to give advice to the older versions of me out there, because there’s a lot of folks who I’ve come to meet that are maybe sitting on the fence and they don’t know if it’s okay to try and give back or, or try and do kind of social good. There’s a lot of people who are in the generation ahead of us, and they’re out there wondering if they should help. Now’s the time to do it.

Nick Caldwell:
There’s, there’s never been more attention and focus on equity and diversity than now. And the numbers are starting to move. So if you’re from kind of that older generation and you’re, you’ve already made it and you’re on the fence about whether or not, you should try and invest in this, do it now. Like this is the time to come out and like help the next generation. We need more heroes out there and I know you’re out there. I know that there’s multiple people who come from the generation before me, who can have an impact in the up and coming generation. So please, I’m begging you. Just go do that.

Maurice Cherry:
All right. Well again, Nick Caldwell, thank you for coming on the show, man. I really appreciate it.

Nick Caldwell:
Yeah, thanks for having me. I had a great time.



Submissions for Volume 2 of the design anthology RECOGNIZE open on March 1! For more information, visit recognize.design!

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Timothy Bardlavens has accomplished a lot since he started designing professionally five years ago. His design journey has taken him from coast to coast, and now he’s at Microsoft helping lead product innovation and UX while also heading up the culture team to foster greater inclusion throughout the company. And he is just getting started!

We talked about how Microsoft has changed over the years, and he shared how he started with humble beginnings in South Carolina and worked his way up to one of the largest tech companies in the world. We also discussed the role of design organizations for designers of color, and we talked about Timothy’s Medium article on leaving AIGA. Timothy’s big goal is to impact the culture, and at the rate he’s going, he’s well on his way to making that happen!


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