Anthony D. Mays

It’s no secret that the tech industry has weathered the last few years better than a lot of others, and many people are trying to ditch their current jobs and start their careers in tech for big opportunities (and even bigger salaries). But working for companies like Google and Microsoft take more than just talent — it takes the helpful hands and heart of this week’s guest, Anthony D. Mays. As the founder of tech career coaching firm Morgan Latimer Consulting, Anthony uses his 20 years of experience as a software engineer and developer to help his clients to ace tech interviews and get real results.

We start our conversation with a quick check-in, and he talks about starting his firm and finding a good work life balance. He spoke about growing up in Compton and learning BASIC on a VTech PreComputer 1000, studying computer science at UC Irvine, and shared how looking for growth opportunities, and his faith in God, helped him succeed throughout his career. So if you’re looking to work in tech, then Anthony is just the person to make that happen!

Transcript

Full Transcript

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

Anthony D. Mays:
Sure. I’m Anthony D. Mays. I’m a former software engineer at Google, and I am presently founder and career coach at Morgan Latimer Consulting.

Maurice Cherry:
How has 2022 been going so far?

Anthony D. Mays:
It’s been an adventure for sure. I left Google on February 1st of this year and I have dived head first into full-time entrepreneurship. Whatever I thought it was going to be, it seems like it’s just a bit different than that, but it’s been for the good and for the best.

Maurice Cherry:
Oh, wow. Congratulations on making the leap.

Anthony D. Mays:
Yeah, thanks. It’s been quite a ride. And I thought that my time at Google was an adventure and a ride, and it just seems like entrepreneurship has made that escalate. It has escalated that ride even faster. I feel like I don’t have guardrails either, so I’m really holding on to my seat, my family and I.

Maurice Cherry:
Let’s talk about your firm. Again, it’s called Morgan Latimer Consulting. For folks who might be interested, that comes from Garrett A. Morgan and Lewis Latimer. Right?

Anthony D. Mays:
Yes. Yup. Garrett A. Morgan, Lewis Latimer, two of my favorite inventors from Black history. They were innovators during a time when it was neither expected for them to be innovators. They weren’t encouraged to be innovators. No one was willing to carve out room. There was no DEI program. There was only racism, discrimination, slavery, things of that nature. But they weathered all of that in order to innovate in this space. And because of the innovations and their contributions to society, we live in the world that we live in today and benefit from the privileges and technology that we enjoy.

Anthony D. Mays:
And so, with my firm, my aim is to renew, I think, an understanding or to introduce an understanding that Black people being innovators in the tech space isn’t anything new. We’ve been doing it. And similarly, other underrepresented groups, the same can be said for them as well. And I want to help connect that next generation of talent, wherever they come from, no matter who they are, whether you’re underrepresented or well-represented, connect that generation of talent to the companies and organizations that are interested in leveraging and harnessing that talent.

Anthony D. Mays:
So I work directly with candidates, but I also consult for companies and help them to understand their hiring processes, their practices, through the lens of someone who’s come from a different background and provide just that insight and wisdom.

Maurice Cherry:
What inspired you to start your own firm like that?

Anthony D. Mays:
I’ve always been attuned to this idea that entrepreneurship is important, especially in America. And when I was in middle school, I attended a very special charter school that was funded by none other than the National Football League. And as part of that middle school experience, I was exposed to entrepreneurship and this idea that I could go and start a business and begin an enterprise and take the risk and dive in. And so, I felt like that sowed the seeds for me to be thinking about entrepreneurship and independence and just making my own moves.

Anthony D. Mays:
I only kind of realize this now, but my career journey has always been set up for this. I think one of the reasons why I wanted to work at a variety of places, spend time doing professional consulting, and then ultimately get to Google is just to establish the credentials and build a network that would allow me to strike out on my own one day and try to carve a different path towards the success that I was looking for.

Anthony D. Mays:
Yeah. So hindsight 2020, I can see where everything all fit together, but it wasn’t immediately clear even when I got into business, when I got into the working world, that my path might take me to entrepreneurship 20 years later. But I’m glad to be here.

Maurice Cherry:
Yeah. It’s having that kind of social proof, I guess, as you might think about it with working for these other places and then striking out on your own. I think it helps with clients certainly to know that, “Oh, well, you know what you’re talking about in terms of the work that you’re doing.” And there’s some level of vetting in place because you’ve managed to have these other experiences first before starting your own thing.

Anthony D. Mays:
Yeah. That’s absolutely right.

Maurice Cherry:
So one thing that you do with your clients, you sort of help them gain the confidence to work in tech, and these are people that either have an interest in tech or maybe might be early career or mid-career, I’m assuming, and you do a lot of prep with them for coding interviews. Tell me about that process, because I’ve heard that Google specifically, their coding interviews can be pretty unusual.

Anthony D. Mays:
Yeah, absolutely. And I think it’s important to really call out that word, confidence, because I think that my job as a coach or my unique contribution is really helping someone to see themselves in the role based upon their experience and their willingness to put in the work.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
And a lot of people can study on their own. There’s tons of resources out there. There’s academies and boot camps and free courses and all that stuff. But there’s this recognition that taking all that stuff in alone may not be enough for some people. And not only that, but there’s these additional challenges and burdens that you may have, especially if you’re from an underrepresented background, where you may not have a network of people who can help you to connect your own life and experience and your own journey to the tech space.

Anthony D. Mays:
And so, what I aim to do is to talk about that and to help people understand how to have the right framework and preparation so that you can begin building that confidence and know that you’re the right person for the job. And that takes a little more effort. That takes me really getting to know my clients. It takes exercising them, paying attention to their problem-solving, making them think through their own problem-solving, arming them with the right frameworks of thinking, so that as you’re tackling different kinds of interviews, you know what you need to do and when you need to do it. And I talk to my clients a lot about building something called muscle memory. It’s the same kind of thing that athletes rely on in professional sports.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
People see them playing the game, but they don’t see them spending the hours of doing repetitive motions and different kinds of exercises to get prepared. They’re able to have confidence at game-time playing at the highest level in front of millions of people because they have that muscle memory. And so, part of what I seek to teach to my candidates and help them develop is that muscle memory so that they can go into an interview knowing that they have a great chance and not hindered by doubt and fear and uncertainty and those kinds of things that often stop very talented people from being successful.

Maurice Cherry:
So you’re kind of like part consultant, part psychiatrist in a way, because you’re kind of helping them to build that internal confidence so, like you said, they see themselves in the role, and I think that is super important. I mean, I’ve worked at a couple of tech startups and I’ve been in the position to hire, and one thing that has been a big thing over the past few years has been inclusive language for job listings.

Maurice Cherry:
And it’s now even a thing to put in job listings, particularly for tech and design positions, to say like, “Even if you don’t have all of these requirements, you should apply anyway,” or “If you only have 50%, apply anyway,” which I think is a way to kind of help people to see themselves in the role because, oftentimes, you may look at the job listing and look at all those different bullet points, and instead of seeing where you’re strong, you see where you’re weak, like, “Well, I don’t have this. Well, I don’t have this many years experience,” and then you end up not applying when, in actuality, what you need to have is the confidence to say, “Well, I’m strong in these things, so I’m going to apply just to kind of see what happens.”

Anthony D. Mays:
Right. And I also want to help you look at that same job description and maybe realize that it’s not for you, that this isn’t going to help you achieve your goals. There’s a lot of people who come to me because they want to crack those top tech companies, those FAANG companies, the Googles, the Amazons, the Microsoft, et cetera, et cetera.

Anthony D. Mays:
And sometimes, I’ve got to look at them and say, “Based upon the goals that you just shared with me, you don’t really need to crack a FAANG company. What you actually need is to consider this startup or maybe think about something mid-tier. Maybe not even a tech company. Maybe you just need to get your foot in the door, and instead of looking at a tech company, you need to look at a non-tech company that has an IT department but also has the framework and infrastructure to help you grow and develop the skills.”

Anthony D. Mays:
So depending upon where you are, you may not understand how to correctly map your specific goals to the opportunities that are out there. If you come away from a conversation with me realizing, “I wanted to do this thing, but I realized that that’s actually not the best fit. Maybe I need to think about entrepreneurship,” then I’m like, “All right. Great. Fantastic. I’ve saved you some time. I’ve saved you some trouble.”

Anthony D. Mays:
And I think that, especially as an entrepreneur now, I realize that my own path was about making it to a place like Google and operating at that level. That’s not everybody’s path. Some people don’t need to pursue that journey. That was my journey. That may not be your journey. And there has to be that conversation. There has to be somebody asking those questions, because I think right now, especially in the tech interviewing, tech prep career coaching space, everybody wants to get you to a FAANG company. They’re pointing you in that direction. They’re talking about those salaries and all that stuff. But you’re not really serving candidates well because you’re selling them this dream and this bill of goods that isn’t going to be helpful for them.

Anthony D. Mays:
I care about my clients and the people that I work with because I think that there’s tons of transformative opportunity out there and available, but you need somebody to come alongside with you to educate you on how to best put a plan in place, helps you get to where you’re trying to go.

Maurice Cherry:
I’ve started seeing companies, even the big ones like the Microsofts and stuff, they’re doing outreach on TikTok. I probably spend too much time on TikTok. But there’s a lot of people on TikTok that are really like, “I want to find the high-paying, six-figure tech jobs. How do you find those jobs?” Because there will be people that have those jobs that are on TikTok, and they’re saying, “These are the perks that I get. I get free lunch here. This is my ride to the office.” And they sort of paint this very idealistic picture of what it means to be in tech through these kinds of perks.

Maurice Cherry:
And I’ll never forget… I interviewed Kristy Tillman. She’s been on the show twice, but Kristy now works at Netflix, and I’ll never forget how she told me to look at perks at companies as filters that just because something may look good in that way, it could also be something that’s used to filter people out. So I do see a lot of… I guess you could almost call it propaganda where people are really painting this very idealistic picture of what it looks like to work in tech in these fancy offices, and you get a free MacBook Pro and all this, but not really showing them what it means, not just to work in tech from day to day, but even the process, like you said, to interview to be a part of a company like that, because it might not even be that they need to be there. They probably just need to start out somewhere smaller maybe.

Anthony D. Mays:
Yeah. No, absolutely. And here’s the deal: You want success and you want the paycheck and all that stuff. You get that by being good at what you do. You get that by being excellent at your craft. And that has more to do with you and how you move and how you develop than it does on the place that you work. And certainly, when you’re working at a company, there’s an expectation that they’re going to play some part in your development, in your growth, and in your assessment, and provide useful feedback, and all those things.

Anthony D. Mays:
But ultimately, you’ve got to take your career and your craft and your responsibility and put in the time and work to be effective and to really be thoughtful about how to make the right plan to get you to where you’re trying to go. And so, I think that a lot of people are looking for shortcuts and they’re trying to circumvent the process, and it’s important that I remind people that there aren’t shortcuts to this. It’s just the same hard work. It’s the same hard work that my ancestors poured into being who they were and accomplishing the things that they accomplished, not letting excuses or things of that nature get in the way. And because of that, they were able to do what they were able to do. And they faced a lot of unfairness. They faced a ton of unfairness.

Maurice Cherry:
Yeah.

Anthony D. Mays:
And just like we face, to certain degrees, unfairness in today’s processes, some of that just comes from natural imperfection. We’re not perfect at what we do as companies or as individuals and applicants. So there’s that, but then there’s also these other biases and even discrimination or racism, to some lesser extent, that we’ve got to combat. And I sometimes struggle with the approaches that I take because I’m very focused on the individual regardless of the surrounding circumstances.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
But the circumstances, those could use some changing as well, and it’s important. And that’s why I want to tackle this from both sides of the bridge. I want to help clients and candidates to understand what they need to do, but I also want to talk to companies and say, “There are some things that you need to change because the talent is ready. It’s not a pipeline issue. It’s a you issue. You need to change what you’re doing and the pipeline will come. The people will come. You just haven’t built a room for them.”

Maurice Cherry:
Yeah. That’s a really good point, to let the companies know that sometimes, there’s things that they’re doing wrong or things that they may be doing, even just in the language in job listings, the way they’ve talked about perks, et cetera, that might set them up in a bad light. It’s funny, speaking about startups and things like this, startups can be a really good place to cut your teeth on working in tech. But they have their own issues too, particularly depending on the scale of where the company is at, and even with diversity and inclusion.

Maurice Cherry:
At least I’ve started to see, on the startup level, it’s becoming less and less of a factor than it has been at larger companies. I don’t know if that’s just because of time or DEI fatigue or whatever. But I remember in the early 2010s when those reports started coming out about Google and Facebook and such about their single-digit workforce numbers for Black employees and what does that mean, and stuff like that.

Anthony D. Mays:
Right. Right.

Maurice Cherry:
And I feel like those companies have started over the years to improve that, certainly. Startups are under no obligation to do that. I just know from working at a couple of them. They do not care.

Anthony D. Mays:
It really depends because… I agree with you that when it comes to the larger companies, there’s an interest to change, but in many respects, it’s almost too little, too late to make the kind of change that you need to make as quickly as you want to. Right?

Anthony D. Mays:
So for some of these larger companies that have been around for 20 years, 40 years, 50 years, whatever that may be, you’re talking about a deeply ingrained culture. There’s a lot of rot that you have to get rid of first before you can even start talking about doing the right things, very carefully guarding that small little flame, that little spark that turns into a fire that then leads to change. So there’s a lot of momentum that you’ve got to slow down if you’re a big company so that you can begin shifting gears.

Anthony D. Mays:
But when you’re a startup, you are in a better position because you’re new, because you have the opportunity to learn from those mistakes and, from the very beginning, think about the right things to do. My latest client right now, I just signed with Karat as a tech advisor for their Brilliant Black Minds program. And what I love about Karat is that from the beginning, they’ve made this very early commitment to increasing the number of Black engineers in the business and really thinking through how they can play a role in that. You can go visit their website and read the statement and the thinking and the resource that they’ve done.

Anthony D. Mays:
I love that they’re small enough and nimble enough to really tackle this problem at a speed that other companies can’t do. And I think that there are similar startups that have that opportunity. And to your earlier point, there are some startups that really did get this wrong in a big way. Most notably, I remember learning about the mess at Uber, and I know that they went through some strides to turn over a new leaf. And from what I understand, things are better, much better than they were back in those days.

Anthony D. Mays:
But you could see that where… When some of today’s startups started making those mistakes, they got called out on it a whole lot faster. It’s a lot harder for those companies to grow and develop without having that scrutiny, whereas 10 years ago, nobody really cared. 15 years ago, 20 years ago, nobody cared. You could do whatever you wanted.

Maurice Cherry:
Yeah.

Anthony D. Mays:
So I think that for those in the audience or for job seekers or candidates who are looking for companies who may have stronger commitments, who may be making better progress, looking at those smaller firms, those startups, those growth phase companies, that might be the better play if that’s something that you care deeply about.

Maurice Cherry:
Okay. I agree. I agree and I disagree. I mean, I’m disagreeing from my own personal experiences, but I do agree that there are some startups out there that are doing it, particularly because you’re starting to see a lot of POC-owned, Black-owned startups. So of course, they have diversity and inclusion in mind because they started it. So that’s something that’s important to them. So I get where you’re coming from. Absolutely. What is a typical day like for you? I know you just said you kind of struck out on your own, but have you started to achieve a work-life balance with the firm?

Anthony D. Mays:
No, I wish. Every day is different, and that’s been great and it’s been challenging at the same time. I woke up today and I was like, “What am I going to do? I know I got to do a podcast, but other than that, what else am I going to do? Should I go put some meetings on the calendar? Should I work on a thing?” And so, I would like to say that I’m a lot more intentional and wise in terms of how I’m planning my time. But each day has been a little bit different, and I find myself in infrastructure-building mode a lot.

Anthony D. Mays:
So I think as I work through some of these beginning things as a new entrepreneur, I’ll get more of the consistency and the regularity out of my routine. But right now, I’m still, I think, figuring it out. I’m trying to be patient with that as well. I don’t want to rush into completely filling up my schedule with things. I want to make sure that everything that I’m committing to is intentional and thought out and is going to serve, in some way, the mission that I’m pursuing.

Anthony D. Mays:
Yeah. From that perspective, it’s been fun. And the other part of this too is that my wife is the co-owner of Morgan Latimer Consulting. So I’m working here at home and my wife is a key partner with me in this effort, largely working behind the scenes. But I’m also getting the kids involved too and having conversations out loud and in the open as they’re doing school.

Anthony D. Mays:
And so, it’s been interesting to expose the whole family to entrepreneurship and to this lifestyle and to be open and honest with my kids about the challenges and opportunities. And so, I think what happens more than that is, I’ll find a learning opportunity in the middle of the day and put everything on pause and talk to my wife or talk to my kids about what I’m thinking and where things can go and even getting their advice and input, and that’s been a lot of fun.

Maurice Cherry:
A true family business. I like that.

Anthony D. Mays:
Yeah. Absolutely. The only other challenge that I’m contending with right now is just needing to travel a little bit more as things thaw out with regards to the pandemic and travel resumes. Now I’m needing to be in more places crossing the country. And so, I try to look for opportunities to bring my family with me so that they can experience that part of it as well.

Maurice Cherry:
Nice. Speaking about family, let’s switch gears here a little bit. You grew up in Compton. I know that because it’s on the hat that you have in all your photos.

Anthony D. Mays:
Well, I could be faking it. I could be-

Maurice Cherry:
No, I don’t think you’re faking it. I don’t know anyone that would fake and… Well, let me not tell that lie. I do know people that would fake and say they’re from the hood. Let me not say that.

Anthony D. Mays:
Right.

Maurice Cherry:
But you’re from L.A. You live in L.A. Tell me, growing up in Compton, was tech a part of your childhood?

Anthony D. Mays:
Yeah, it was, amazingly enough. And that may come across as unexpected for some of your listeners. But growing up in a poor place, in a place like Compton that was renowned for things like gang violence, drugs, poverty, all that stuff, now, well, it turns out that having rich people in the area means that we receive some investment and support from very notable people. And I think it was Magic Johnson who, in the early ’90s, donated a non-trivial sum of money to my elementary school. As a result, we got a basketball court, but also a computer lab.

Maurice Cherry:
Hmm.

Anthony D. Mays:
And it was in that computer lab when I was in the second grade that I had the opportunity to use a computer for the first time. And it profoundly changed my life because that’s when I realized that computers were cool and this might be something that I want to keep doing, whether I get paid for it or not. And so, I remember asking my parents for a computer and they said no, and I didn’t understand at the time that computers were $5,000 or more to get something decent. But my foster parents, as well as my birth mom, they both bought me toy computers, which were super cool. And when I was about eight years old, I used one of those toy computers to teach myself how to code.

Maurice Cherry:
Mmm.

Anthony D. Mays:
And I remember, at the time, I was being bullied for a variety of reasons. And so, I became somewhat of an introvert out of necessity and would pour focus and time and attention into computers and programming. And I just remember feeling this sense of empowerment and agency and control using computers that I didn’t have in other aspects of my life. I failed to mention this, and it’s pretty much common knowledge now, but I grew up as a foster kid after my first grade teacher or kindergarten teacher had found signs of physical abuse.

Anthony D. Mays:
And so, losing your whole family and being moved out of your home is a very transformative and traumatic experience for someone who’s four years old. And I found that interacting with technology allowed me to reclaim control and power and just to have a space to be me and to be a creative thinker and an innovative thinker. I wasn’t building apps and all this stuff, but it was enough to whet my appetite and get me engaged, and I would just continue to pursue computers throughout middle school and throughout high school where I was fortunate in both cases to meet mentors who saw that early love and decided to invest time into developing my knowledge around technology and the internet.

Maurice Cherry:
Hmm. Something you mentioned there, I think, we have in common in terms of growing up in… I don’t want to say small towns. I don’t know how large Compton is, but certainly growing up in towns with dubious reputations.

Anthony D. Mays:
Yeah.

Maurice Cherry:
I’m from Selma, as most people-

Anthony D. Mays:
Hey.

Maurice Cherry:
… know from the show, from Selma, Alabama. Kind of like the first generation out from Bloody Sunday. And so, now Selma is like a pit stop on every politician’s tour throughout the country. They stop in, they go to Brown Chapel AME, they walk across the bridge, yada yada yada. They do all that stuff. But because of that general perennial attention on the city, you do have people that will come in and there’s like an influx of cash to one of the local schools or… You know what I mean? So we had a computer lab in high school, which is how I learned about the internet. That was my first foray with Netscape Navigator 1.0.

Anthony D. Mays:
Oh, wow. Let’s get it. Yes. Yeah. I’m right there with you, brother. We learned that the same time.

Maurice Cherry:
Yeah. That was in my… I was in, I think, ninth or tenth grade when they installed the computer lab and got to see what the internet was like back then. But even as you mentioned learning and teaching yourself how to code with these toy computers, I’m super curious, what was the computers that you were using?

Anthony D. Mays:
Yeah. So the one that I used specifically to learn coding was called the PreComputer 1000.

Maurice Cherry:
Get out! Oh, I’m sorry. Go ahead.

Anthony D. Mays:
Oh, yeah.

Maurice Cherry:
No, no, no. No, keep going. Sorry. Sorry. I had that same computer. I had that same… The blue one with the handle?

Anthony D. Mays:
That’s the blue one with the handle. Absolutely.

Maurice Cherry:
Okay. Okay. Okay. Okay. Go ahead. Go ahead. Go ahead.

Anthony D. Mays:
So I’ll tell you a funny story real quick. I would talk about that computer when I would go to schools during my time at Google and all this stuff, and I had lost the computer. I didn’t have… I don’t know what happened with it. Things get lost, as they do, over decades. And one day, this Christmas present was sitting on my desk and I opened it up, and it’s a PreComputer 1000. A co-worker had bought me a PreComputer 1000 off of eBay or something because they knew that I had grown up on that computer and they knew-

Maurice Cherry:
Wow.

Anthony D. Mays:
… how passionate I was about sharing technology with the young people. And so, I would take that computer with me on tours and flip the switch where you’d hear the little (singing). And I would take out the big old fat D batteries on the back and say,-

Maurice Cherry:
Oh man.

Anthony D. Mays:
… “This is it.” That’s what I had. And one of the reasons why I’m passionate about supporting underrepresented people in tech specifically is because out of scarcity comes innovation.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
Out of scarcity and challenge and struggle comes some of the best ideas and some of the greatest opportunities to do things that haven’t been done before. And for me, growing up under the scarce conditions of the hood and with the family that I often describe as middle-class poor, that led to me doing things like teaching myself how to code and learning about the internet and all these other kinds of things. For an industry that’s looking for talent that knows how to build technology under those kinds of circumstances, what better place to look than the hoods and ghettos of America?

Maurice Cherry:
Yeah.

Anthony D. Mays:
Why spend all of this time going overseas looking for that kind of talent when we have our own neglected neighborhoods in the backyards of America?

Maurice Cherry:
Yeah. Listen, these kids don’t know how good they got it now. When you have to teach-

Anthony D. Mays:
They really don’t.

Maurice Cherry:
… yourself how to code on a one-line dot-matrix screen…

Anthony D. Mays:
That’s right.

Maurice Cherry:
I mean, come on. So my older brother had… And this is when I was younger. I probably might have been about seven or eight or something. He had a… It was also a VTech, but it was a Laser 50.

Anthony D. Mays:
Mmm.

Maurice Cherry:
And so, the Laser 50 is about the size of a standard, regular keyboard that you would get now, but it had a one-line dot-matrix screen at the very top and you would use that to code. And I remember… The Laser 50 was particularly interesting because it had all these peripherals you could get for it. You could get a tiny dot-matrix printer. You could get a tiny-

Anthony D. Mays:
Oh, wow.

Maurice Cherry:
… storage thing. And storage back then were cassettes, because you didn’t have flash drives. You didn’t have…

Anthony D. Mays:
Yup.

Maurice Cherry:
I mean, you had floppy disks, but you certainly didn’t have… But it was a cassette. And so, I would often be mistakenly putting data, like taping over somebody’s radio mix, because it used this…

Anthony D. Mays:
Oh, no. Not the radio mix.

Maurice Cherry:
Trying to explain to someone that like, “Yeah. We use cassettes for music and for data storage.” They’re like, “What? I don’t get that.” But yeah, I had a PreComputer 1000. I think I was in probably fourth or fifth grade. I remember that spiral-bound flip notebook. I taught myself how to type on that thing.

Anthony D. Mays:
There it is.

Maurice Cherry:
I taught myself music on that thing. I’m sure my mom wanted to launch it into space because I was making all kinds of noise on that thing. Yeah. And it’s funny, you mentioned getting one off of eBay. Someone gifted one to you. I got one off eBay also-

Anthony D. Mays:
Hey, there it is.

Maurice Cherry:
… a few years ago. I got a Laser 50 and I got a PreComputer 1000 just to have them as artifacts of like, “This is how I got into technology.”

Anthony D. Mays:
Yeah. And I wish that I had the opportunity to meet the product managers or project managers who worked on that because it would be so great to just give them a personal thank you for thinking about a product like this. Again, to your earlier point, I’m hard on this generation of technologists that are coming up because, as you said, they don’t realize how good they have it. And I do understand that there’s a challenge. There’s so much information that it can be hard to pick through what’s reliable and useful from that, which isn’t.

Anthony D. Mays:
But I had to go to a library that had books that were five, 10 years old out of date, trying to teach myself coding and programming, just kind of growing in that. That was a tough challenge, and that was… It was enough to make me give up programming until I got out of high school when I would go get my first job as a developer.

Anthony D. Mays:
I remember feeling so frustrated because I would pick up these old books and I would try to apply what I was learning, but I didn’t understand it all the way and I didn’t have someone that I could lean on to explain. I remember this one time in middle school where I typed out this whole program. I must have spent a couple hours just typing out this whole program into Notepad on Windows.

Maurice Cherry:
Whoo! That takes me back.

Anthony D. Mays:
Yeah. And so, I saved… I just saved this text document as an exe thinking, “Well, all I have to do is just save it and then change the extension to exe and I should be able to double-click and run it.” And I spent an hour just trying to get that to work and it wouldn’t work, and I was so frustrated because I didn’t understand that you needed a compiler in between that’ll produce the actual program. And so, I remember those kinds of moments.

Anthony D. Mays:
And then I think about the fact that my son can watch a YouTube video now that tells him exactly what tools to install and how to make it all work and have all the sample code and then he could put that up on GitHub and all this other stuff. And so, I reflect on that and I try to… I have to kind of take a step back and just not yell at people, not get gangsta at them.

Maurice Cherry:
Yeah.

Anthony D. Mays:
What do you mean? What are you talking about? You ain’t got no struggle. What are you talking about you can’t do this? What are you talking about you don’t have information?

Maurice Cherry:
Yeah.

Anthony D. Mays:
Get over it.

Maurice Cherry:
Oh man. I remember we… Our public library had one book on BASIC. It was like this green and white book. And I mean, I check that thing out every two weeks till the cover came off, taped the cover back on. And because Selma is like a… It’s a small town. It’s like 20,000 people maybe.

Anthony D. Mays:
Yeah.

Maurice Cherry:
No mall or anything. So the nearest bookstore was 50-plus miles away in Montgomery. So if I was like, “Oh, I want to go get a book,” that’s a whole trip. That’s a field trip, pretty much.

Anthony D. Mays:
Right.

Maurice Cherry:
Oh God, I think I got my first HTML book, I might have been in high school or something, but I remember getting it at the Montgomery Mall because we were at some trip in Montgomery and I got it. But there’s… Also during that time, I spent a lot of time in the computer lab by myself. My mom worked at a college. And so, I had access to Windows computers. And I just spent so much time looking at source code, writing stuff down, trying to figure out how it all worked, because I could only do it at the computer lab. I would do that and then have to go home and write a paper on a typewriter.

Anthony D. Mays:
Yeah. Right. Right. Right.

Maurice Cherry:
Because I could only use the computer either at high school or I could use it at my mom’s work at the college. I didn’t get my own personal computer until I went off to college in ’99. But yeah, kids, they don’t know how good they got it. I’m saying kids in a general pejorative sense, but just like, people that are learning technology now, there’s so much at your fingertips. It’s astonishing.

Anthony D. Mays:
I mean, and that’s the thing is… One of the things I try to impress on this generation is the importance of making things and building things and being public about that.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
So as you’re learning and as you’re growing, assemble that gallery, assemble that portfolio, and make it external and use social media to your advantage. These are things I didn’t learn till later on, but it was partly because of those reasons that I was able to even get the attention of a Google in the first place. And I think that… I ponder what my path in tech might have looked like had I had the tools that I had. And another part of this too, because having a son and daughter, my son is 15, my daughter is 12, I look at them and I realize that they just don’t have the same gumption. They don’t have the same motivation that I did, my drive and my wife’s drive.

Anthony D. Mays:
We came from a place where you had to find a pathway to success. You needed the struggle. You needed to overcome a lot and be intentional about figuring out where you wanted to go to avoid all the little traps that come with growing up in the hood. And so, we were sufficiently motivated to take advantage of every possible resource we could find and get our hands on to succeed. My kids benefit from a great deal of privilege. And without much effort at all, they have access to tons of information and tons of resources, but not necessarily having that drive.

Anthony D. Mays:
And I think that there’s time for them to develop that and to grow on that. There’s a sense in which I want them to just enjoy ingesting knowledge and doing it carefully, but just being slow. They don’t need to build an empire now. But I’ve got to push them a little bit to put in the work to really realize what they have so that they are being producers and not just consumers of technology.

Maurice Cherry:
Mmm. I want to go back to… You mentioned, in high school, you had this aptitude for technology after learning about it so much. And then for college, you went to UC Irvine. Tell me about that time. What was it like there?

Anthony D. Mays:
That was an interesting and difficult time for me personally, and I don’t mean difficult just in terms of challenging. Yeah, it was challenging, as education should be, but there was also this aspect where I think I had to deal with difficulty that maybe other people didn’t have to experience. The first thing is that I didn’t see a lot of people who look like me and who came from where I came from in classes with me learning about computer science.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
I looked at the population of students that I was surrounded by in the computer science program versus in other places of the university and would sometimes think to myself, “Am I in the wrong major? Is this really a pathway and a world built for me?”

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
And I had to struggle through that. I didn’t have the best study habits. Well, let me put it another way. I was a lazy bum when it came to school. I think part of it was that I didn’t understand how I learned and how I would best ingest information. And so, that was one thing. But the other part of it was that, in school, I had to conserve energy a lot. I wasn’t one of those kinds of people that could just go to school and focus on my studies. I also had to work. I had to earn income to make sure that… And I had scholarships, but I didn’t have a full ride.

Anthony D. Mays:
And so, there was a lot of context switching between being devoted to school, but then also making sure that I’m taking care of bills and other concerns associated with being an adult on your own. And so, I think in the craziest time of college, I would go to school at UC Irvine. I would drive to downtown L.A., which took about an hour and a half, to go work part-time on my job. And then I would sometimes come back to school, which was another hour, finish off classes, and then drive 30 minutes home. And that was a real grind for, ooh, a couple of years throughout my college education.

Anthony D. Mays:
When I talk about providing the perspective of someone who’s underrepresented, there are a lot of people who want to get into tech who have very challenging life circumstances, where they struggle just to either support themselves or their family or whatever that may be, and they’re trying to get their leg up and study and learn all these things, and it’s a challenge. But by God’s grace, even in college, I had a lot of good support and that I had summer internships through the INROADS program. That was fantastic and really helped to root my education.

Anthony D. Mays:
And then during the year, I had the opportunity to work for City National Bank to work as a developer in real life. And so, in addition to what I was getting in the classroom, I was also, in some respects, playing that out in the working world. And so, it was good to have that reinforcement there. And there were a community of folks that I could lean on and talk to. I think there was a good community of Black folks on campus.

Anthony D. Mays:
I did other strategic things. I took gospel choir three times in college. I don’t even know if I got credit for the last time I took it because I think there was a limit, but I would take gospel choir because I grew up in the church and I grew up as a gospel music musician from the time that I was, I don’t know, nine years old, 10 years old, and I’ve been playing every Sunday at church ever since then. So gospel choir in college was a safe space for me, if I can use that phrase, for me to just be around something familiar and around something that really encouraged and gave me hope. So it was great.

Anthony D. Mays:
And ultimately, I left the University of California, Irvine with a 2.87 GPA on the five-year plan. I had gone to a charter school for high school as well and had great education opportunities. I really should have gotten out of college in three years because I came in with college credits. It took me five. And I reflect on how challenging that was and how that experience impacted how I saw myself as a professional after I graduated, because I didn’t have a lot of confidence when I graduated high school, even though I would go on and get a job and all that stuff. I certainly didn’t see myself as big tech material, as Google material. Just walking across the stage with a diploma was a generational accomplishment, if you know what I mean.

Maurice Cherry:
Yeah.

Anthony D. Mays:
And so, when you’re coming from the perspective of survival, any success is big success. And so, it didn’t take very much for me to feel satisfied and accomplished after graduating college. And I had no idea the amount of headroom I had to work with in my career. If I would’ve known then what I know today, I think that would’ve drastically changed my career trajectory and path. I didn’t have those examples. I didn’t have that network of people that I could look to and say, “Hey, I want to be like this person.” I see that they kind of have a path like mine’s and they’ve had some struggles and they’re able to do what they’re doing. I might be able to do the same thing. Let me apply myself. Let me work even harder. Let me take advantage of these opportunities that I was too scared to take advantage of.

Anthony D. Mays:
And I think that’s why I’m so public about my own journey, my own trials, and really kind of getting in the face of other folks who might be like me or might have come from where I’ve come from to let them know that I am that living example of what they can accomplish if they’re willing to take the risks and to step out on faith, as it were, and really own their journey, their path, their growth, and their development.

Maurice Cherry:
Well, once you graduated from UC Irvine, what was your early career like?

Anthony D. Mays:
Yeah. So I transitioned from being an intern to a full-time employee at City National Bank. The experience was a little jarring in that when you grow up in a computer science education, you kind of expect that you’re going to see theoretical things playing out in the real world. And for the first several years of my career, I really didn’t see that happen, and it’s because I didn’t understand that a computer science education is really designed to position you well for working at a tech company or working at a tech-focused organization. And at the time, I was working for a bank. Banks aren’t tech companies.

Maurice Cherry:
Yeah.

Anthony D. Mays:
They see IT as a cost center. They see IT as a… You want to spend the least amount of money possible to get the bare minimum so that you minimize the cost. And so, they just didn’t care a lot about making things fast or quick or really applying, at that time, good UX principles and stuff like that. And so, it was confusing. I’d say, “Hey, we need to do this and have these kinds of practices,” and it was always seen as a burden and as something that kind of slowed down the process.

Anthony D. Mays:
And so, I was confused by this and eventually began to fit into the more corporate IT way of thinking about software development and all those things. That’s useful. It was useful for where I was moving at the time. I learned how to engage with my craft in that kind of environment and find success, but I became detached from what I was learning in school.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
And I didn’t really connect with that again until the Google interview, where I had to dust off the Data Structures and Algorithms book and reacquaint myself with the big O and with some of these other formal concepts that I learned in my computer science education. But the upside of working in the corporate environment that I worked in during those times is that because of what I perceived as chaos and disorganization, I got to learn a crap ton of stuff. It’s kind of like working at a startup that just hasn’t figured it out yet.

Anthony D. Mays:
You do 10,000 things, because there’s nobody else to figure it out. And so, you’re just kind of throwing mud at the wall to see if it sticks. That was kind of my experience early in my career. And so, that made things fun. And I would often say yes to things, even if I didn’t know what it was or how it worked. My boss says, “Okay. Who wants to tackle this thing?” “Yeah, I’ll tackle it. I don’t know what this is, but if you give me time, I’ll figure it out.” And I’ve just began to develop and grow that muscle of figuring things out, going from knowing nothing to knowing something to then being effective. Repeating that process over and over again really helped me to develop good, solid problem-solving skills that I would take later into my career.

Maurice Cherry:
And you were at City National Bank for a long time, like almost nine years.

Anthony D. Mays:
Yeah.

Maurice Cherry:
And even after that, you worked at a couple of other places for a pretty long time. You worked at Slalom Consulting. You worked at Junction eCommerce On Demand. When you look back at these experiences collectively, what do you remember?

Anthony D. Mays:
I definitely remember leaving City National Bank and making that decision. What caused me to leave… For me, money isn’t everything. And what’s more important to me, or at least what was more important to me at the time, was growth opportunity and learning. I felt like I needed to learn and grow or at least get paid really good money to stay in my seat. And at the time, I felt like I wasn’t really growing in the way that I wanted to grow and stepping into opportunities that I wanted to step into.

Anthony D. Mays:
And part of that was because I was working for a bank in 2008 in the middle of something called a financial crisis and a Great Recession. So I was not in the best industry for that kind of stuff anyway. And so, I decided to leave at the time to pursue growth in my development. And so, I remember going from this non-technical company to a tech company in JunctionEOD and all of a sudden connecting with some of these things that I talked about learning in my computer science education.

Anthony D. Mays:
I was like, “Oh, okay. That’s where this really applies.” And so, I got to learn a lot of cool stuff and to do some things that would set me up again for success later on. Got to work with a… I’d worked in a large company with thousands of employees, and then ended up working in this department where there were just five of us. And so, it felt very much like a startup or a startup in growth phase. It was interesting to work with… to have a technical manager and someone who was a manager, who was also an engineer. My previous manager wasn’t an engineer. I have experience coding before, but really didn’t dabble in the technical.

Anthony D. Mays:
So to go from that to someone who is technical and having those discussions, I just found that to be cool. And I really learned a lot from my boss at the time, Mike, who was just a great engineer, double-majored in physics and math, I think it was, or actually had a master’s degree in physics and math. So just really a smart guy. I just remember growing and develop… Honestly, Mike, if you’re listening, sorry, wasn’t necessarily the best manager at the time. And so, I perceived that I needed to get myself into a position where I could find even more growth and learning.

Anthony D. Mays:
But again, a lot of what motivated me to move from one place to the other was the learning and the growth, not necessarily the money. Now, as I move from one company to the next, I found myself getting $15,000 raises each time, so that was nice. But it wasn’t something I was looking for.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
I felt like it was just necessary for me to keep growing and keep getting better. And if I didn’t feel like that was happening, then I wanted to move. And so, by the time I got to Slalom Consulting, I had the opportunity to work with consultants in past jobs and past roles, and I really loved looking at consultants and watching them work and seeing the kinds of opportunities they got to dive into. And so, when I had the chance to become a consultant, I really enjoyed that, and working on a variety of customer projects in a variety of different contexts and seeing how the same skills I’ve been using for over a decade at that point could be used in a variety of different contexts. And that was very helpful. Very, very helpful.

Anthony D. Mays:
And again, I love this idea of being hired to be an expert in something that I didn’t know or understand yet, being entrusted to just kind of dive in and start solving problems using brand new tools and processes, and I really enjoyed that. And I enjoy Slalom as a company. I think Slalom continues to be a great company and I hear nothing but good things, still, from folks who have worked there in the past and have gone on to other things. I might still actually be at Slalom today if it hadn’t been for Google knocking on the door.

Maurice Cherry:
Well, let’s talk about Google. I mean, I’m sure that folks that are listening have heard about how tough it is to break into Google, their interview process, et cetera. Tell me about what your Google experience was like.

Anthony D. Mays:
Yeah. So I connected with Google as a young man in college, my first and second year of college actually. So Google Search showed up on the scene, and you probably remember Infoseek and AltaVista and Ask Jeeves and those earlier search engines.

Maurice Cherry:
Yeah.

Anthony D. Mays:
And I remember Google Search coming on the scene and just changing the game. All of a sudden, I felt like I had this world of information at my fingertips where I could find exactly what I was looking for with just a few keystrokes. Then I remember Gmail, this free mail service. And people take advantage of, then neglect to appreciate free email. You had Gmail, which is free email service. I could put attachments in and schoolwork there and use it, and it was amazing.

Anthony D. Mays:
And I thought Google as a company name was a weird name. The first thing I said was, “Look at this Yahoo clone. Google. Who do they think they are?”

Maurice Cherry:
Yeah.

Anthony D. Mays:
But they were interesting and innovative, and they were dabbling in a bunch of these different spaces even in the early days. And then they went public and made millions of dollars for folks who had joined the company early and been part of that process. I was attracted to Google as a company and to Google technology. And even today, post-Google career, I still love Google products and services. And I forgot to turn off the device, and so there might be something that… The Assistant might chirp in and interrupt me at any time now. I’ve always loved the technologies and things they built and their ambition as well.

Maurice Cherry:
Yeah.

Anthony D. Mays:
And so, even though I love the company, I never saw myself being worthy of being employed there, being considered amongst the ranks of software engineers there. And so, when I encountered a recruiter in college, I think it was my third year of college, they gave me an application, asked me to fill it out for an internship. I walked away some steps and threw the application in the trash, because I knew-

Maurice Cherry:
Whoa.

Anthony D. Mays:
… that they weren’t going to hire a Black dude from the hood. I just knew that. They weren’t going to hire a Black man from the hood who’s a former physical, sexual abuse victim. I’m like, “No.” So that was my early interaction with Google. And then some years later, 11 years into my career, a recruiter reached out to me over LinkedIn and said, “Hey, I think that there’s a place and a role for you at the company. You should consider applying.” And it felt different because the recruiter used my full name. They singled me out on LinkedIn.

Maurice Cherry:
Yeah.

Anthony D. Mays:
And I had 11 years of career experience under my belt at that point. And so, I felt emboldened to go through the interview process. Yeah. I didn’t have a friend, cousin, uncle, brother, whatever, that had worked anywhere near a big tech company. And so, I had to do what any self-respecting engineer would do in my position. I googled it. “How do you succeed at this interview process?” And I came across some good information but I also came across some bad information. I didn’t know how to disambiguate the two. And so, I ended up studying brain teasers for two weeks and went into this interview process and not a single brain teaser was asked.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
And I fought as hard as I could with the information that I had and worked very hard. It wasn’t an issue of work ethic. It was an issue of information and not being connected to the right network. And ultimately, I was saddened to hear from the recruiter that they weren’t going to move forward. And I remember reflecting on that “no” and thinking that I had let down myself, my family, my community, my church, all Black people everywhere, because when-

Maurice Cherry:
Oh, wow.

Anthony D. Mays:
Yeah. I mean, when I’m coming into the space as an underrepresented person, I know that the people that I’m talking to, I might be one of the very few Black folks that they ever talked to, one of the very few people from Compton. Maybe the only person from Compton that they’ll ever meet, and that they’re forming ideas about who I am and about what I represent. And so, I was aware of that burden and I was deeply impacted by that.

Anthony D. Mays:
So when recruiters would reach out the next year and the year after that, I think three times total, after I had failed the interview, I was very confused. I was like, “Y’all know I’m a Black man, right?” Right? Everybody says they’re going to call you back if a position is available. No one ever does. And these recruiters called me back, I think, three times. And my last recruiter understood that I was very hesitant to reengage with the process.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
It kind of babied me, kind of coddled me in the conversation. And I kind of walked away from that thinking, “She thinks I’m a punk.” She’s calling me a… That’s really what’s going on here. She’s calling me a punk. I can’t go out like that.

Maurice Cherry:
Mm-hmm.

Anthony D. Mays:
And so, after talking to my wife and getting her support, I realized that I wanted to try again. And so, I picked up Cracking the Coding Interview by Gayle Laakmann McDowell, bought a whiteboard and some markers, really committed myself to studying the right information this time. And as a result of a month and a half of studying for, I don’t know, three or four hours a day, except for Sundays because I’m closed on Sundays, I was able to go through the interview process and get the job.

Anthony D. Mays:
And you would think that after that, everything is happily ever after, like, “Yay, you did it. You accomplished this amazing feat. Now you can rest and ride off into the sunset.” Well, as soon as I got to Google, I felt uncomfortable. And it wasn’t because of anything specific that people were doing. It’s that I just… I couldn’t sit in my seat. I was unnerved and restless. I would sit in this cafe surrounded by free food, free snacks, free beverages, by games and pool tables and really smart people, and my attention would be directed to the basketball court on the first floor as I’m watching these dudes duke it out on the basketball court.

Anthony D. Mays:
And I’m like, I understand that part. I understand basketball. I understand that struggle. I understand that life. I don’t understand this. I don’t understand tech, this new privilege. And there’s this culture shock. I’m forced to dress different than I had ever dressed before. I start off my career in a bank, suit and tie, and everybody’s now wearing jeans and a T-shirt. The whole thing is jarring. My bosses… My co-workers are telling me that I’m doing a good job, and I don’t believe them because I know I’m the diversity hire. Right?

Anthony D. Mays:
You ain’t got to lie to kick it. I’m the diversity hire. You hired me because you don’t have that many Black folks and you just want to make sure that your numbers look good. So I knew all those things, even though it wasn’t necessarily true. And it wasn’t until 2014 when Google released their diversity numbers that I realized what I was dealing with. It wasn’t just impostor syndrome. It was this awareness that I’m this underrepresented person put in this culture that wasn’t built for me.

Anthony D. Mays:
And I felt like, at the time when Google released their numbers, if they were making a commitment to bring visibility and light to this problem, I needed to take a role in helping to solve that problem and using every means at my disposal to bring positive change to the industry using my own experience and journey. And so, I started to write about my journey and experience and share interview tips and talk about things that I did well and things I didn’t do well. I tried to be very public about the failure that I had during the first interview and the successes during the second one, and just be open and honest about the struggles and all that. And as I did that, people would reward me with recognition and with support and encouragement.

Anthony D. Mays:
And I thank God that, at Google, I had the opportunity to start off as an engineer, just heads down writing code, but then eventually become this DEI advocate, this speaker, this consultant within the company, and even outside the company, talking about this experience in recruiting and what it means to be an underrepresented person in tech. And so, I really enjoyed the fact that not only did my boss support me in that work, but my boss’s boss and my boss’s boss’s boss, they all said, “Listen, you do your thing. Keep speaking, keep writing, keep supporting, keep providing value to the tech community, and we’ll make sure that your performance reviews reflect those contributions positively.”

Anthony D. Mays:
I felt like it was a unique time, a unique team, and a great time for me to be involved in the work and growing. And I credit the influence and the things that make me who I am today in part to Google and the people that I had the opportunity to work with. So I think because of that, I know that a lot of people are doing the work. I don’t know that many companies are doing it better than Google is at least in some respects.

Maurice Cherry:
I mean, it sounds like you really found yourself there, not only as a professional but, in a way, almost as a person. You had these early times of impostor syndrome and self-doubt, and you were able to overcome that through your time there.

Anthony D. Mays:
Yeah, absolutely. I mean, there was so much self-discovery for me, partly because of all the bags that I brought through in my life and the time that I was a kid. I mean, I really had to confront my whole life in that whole journey when I got to Google. And I don’t know why it was that it took me getting to Google to do that, but I really went through a crisis when I got to Google.

Anthony D. Mays:
There’s this thing called survivor’s guilt where, when you feel like you’ve survived trauma, you feel guilty and ask questions like, “Why is it that I wasn’t shot and killed when I was 19 like some of my early friends had been? Why is it that I wasn’t being funeralized? Why is it that even though I saw other people who were working harder than me and who I thought were smarter than me, why did I make it to this level and they didn’t?” And I really had to grapple with that. And it took me to some very dark places personally.

Anthony D. Mays:
My wife, my family can tell you that I really found it difficult to bear with that stress. And I told my boss, I said, “Listen, have you ever managed someone who’s a physical and sexual abuse survivor to the best of your knowledge?” Said, “No.” I said, “Well, have you ever managed someone who’s a foster kid from the hood?” “No.” I said, “Okay. So we’re both new at this. We’re both going to figure this out. But my commitment to you is that I’m going to work as hard as I possibly can to contribute to this team, to do excellent work, and to pay attention to my craft. That’s my commitment to you, and we’ll figure the rest out.” And I believe that my manager was very great and understanding in coming alongside with me for that journey and just being open and honest. So I appreciate that to this day.

Maurice Cherry:
Where do you see diversity in tech now, from your perspective?

Anthony D. Mays:
Yeah. It’s still… I feel like it’s still burgeoning. We’re still in the early stages in many respects. I can remember when… Even just a few years ago, we were still struggling to figure out terminology, and that’s one of the frustrating things about working in DEI, is it seems like the glossary’s changing every single year. New words to use, new things to add to the language.

Maurice Cherry:
BIPOC.

Anthony D. Mays:
Yeah, exactly. I think, a month ago, I was like, “What’s that?” And I had to ask somebody, “What’s a URM stand for?” because I forgot what it was. Even when I joined Google, I was just like, “Do I call myself Black or African American?”

Maurice Cherry:
Yeah.

Anthony D. Mays:
I was asking myself that. And so, there’s still a lot of newness in this space. And part of… I think there’s also a conflict between the academic understanding of DEI and things like critical race theory and all that stuff, thought leaders who are on that level. But then you have people who are just trying… who are experiencing what it’s like being in the workplace rubbing up against people that you may not understand, who have experiences that you may not be familiar with and just trying to figure it out on an emotional level.

Anthony D. Mays:
I think those two perspectives sometimes come into conflict and companies are trying to figure out what to do in the middle of all of that. A decade ago, maybe even five years ago, you wouldn’t hear about love being talked about in the workplace, unless you’re talking about workplace romances. But there’s this notion that tech companies are trying to figure out how to love their employees, which is really weird even when I say that now. But I’ve had to expose more of my life in big tech in the past several years than I ever had to before, and that’s because tech, I think pre-2013, 2014, was very much color-blind. We don’t see race, we don’t see gender, all those other kinds of things.

Anthony D. Mays:
There was this big emphasis on an extreme side of the spectrum where you just pretended to ignore these differentiations between people of different backgrounds and whatnot, then tried to typecast everybody as this one thing. And that was harmful, I think. I don’t think that was helpful. To a certain extent, you want to make sure that you have a culture where everybody feels like they’re working on the same mission and going in the same direction. I don’t want to negate that, but there’s also disservice when you are pretending to be color-blind.

Anthony D. Mays:
Last time I checked, color blindness is considered a disorder or a disability or whatever the right word is for that. It’s not something helpful. And so, I think we’re starting to open our eyes and see color for the first time and see some of these other things for the first time and are still figuring it out. And like I said, there’s a lot of things that are happening both at the big tech company and at the small tech company level to correct and chart a new path forward. But it’s messy work.

Anthony D. Mays:
And even that, it’s refreshing to be able to admit that nowadays because back in the days, DEI was a bunch of people who look different, holding hands, singing Kumbaya, sitting in the middle of a park, high-fiving each other. That was kind of the ideal some years ago, and I think we’re realizing that that’s not what the work looks like. The work is grimy, it’s messy, it’s hard, it’s difficult. There’s a lot of disagreement. There’s agreeing to disagree.

Anthony D. Mays:
But at the end of the day, the hope is that all of these different perspectives will inform a culture that fosters innovation and creativity and new ways of thinking about old problems. And so, there’s clearly business opportunity here. I think the research bears that out, and I think companies are understanding that there’s a lot of money to be made by having these discussions and thinking through these things. And that’s not bad.

Maurice Cherry:
What’s something that perhaps not many people understand about you? I mean, I feel like you’ve put so much of your life story out there, not just with the work that you do, but also at the places where you’ve worked.

Anthony D. Mays:
Yeah.

Maurice Cherry:
What’s something you think people still don’t get about you?

Anthony D. Mays:
My faith, absolutely.

Maurice Cherry:
Mmm.

Anthony D. Mays:
Hands down. It’s the fact that I think about all the things that I think about from the lens of someone who’s a Christian and is saturated in the Christian Bible and in the scriptures. I’ve told people countless times, “If you ever want to figure me out, go read that Bible, then you’ll have me dead to rights.” That’s it. I mean, I do what I do because my hero, my Savior, Christ Jesus, was someone who gave himself up for the world. That style of servant leadership, that sacrificing for other people is very core to what I do.

Anthony D. Mays:
Also, just in terms of my work ethic and how I engage, I want to make sure that I’m a good reflection of Christ. I want to make sure that I’m moving in wisdom. Proverbs, I grew up on the Book of Proverbs when I was growing up and learning about everything from how to manage money wisely, to how to have conversations with people that are going to be positive and good, to how to win friends, and how to avoid the traps of street life.

Anthony D. Mays:
A lot of that I learned from the Bible, from Proverbs, and from looking at these exemplary figures, these historical figures, who have to overcome a variety of different circumstances and challenges and trials with their faith rested on God. And that’s how I move today. So much of what I do is also gospel-focused too. I think one of the things that helps me to be a DEI practitioner, talking about diversity, equity, and inclusion, is my faith. Seeing people as made in the image of God.

Anthony D. Mays:
For me, it’s not about just helping Black people or just helping brown people or just helping women, whatever that is. It’s about helping anybody in the space that wants to be successful. And then there’s this other aspect of like, “I know how evil I am in my own heart because the Bible teaches me that.” And so, I can have a conversation with someone who maybe is an overt racist and talk about their viewpoints and talk about why I might disagree with them and call them to have hope in Christ and to see that their thinking is evil.

Anthony D. Mays:
But I also know that I’m a bad dude. I have done things over my own career and over my own life that I’m certainly not proud of because they were wrong, and that means that I can have compassion towards other people who I disagree with and have those calm conversations. One of the things that I tell people all the time is, “You can ask me about anything with regards to race, gender, my life, whatever. I don’t care. My promise is that I’m not going to get angry with you. You’re going to get nothing from me but love and compassion as we talk through very difficult things,” because that’s the way my Savior moves. That drives so much of what I do and how I think about the things that I think about.

Anthony D. Mays:
I’m glad that I’m able to reflect the goodness of God, reflect the grace of Christ in what I do. And hopefully, people see that. Hopefully, people perceive that. And hopefully, people are curious about what drives me to do the things that I do with the level of excellence that I try to pour into those things.

Maurice Cherry:
What are you excited about at the moment?

Anthony D. Mays:
So I’m very excited about the work that I’m doing with my client, Karat, as the newly signed technical advisor, senior advisor, with the Brilliant Black Minds program. I love the Brilliant Black Minds program because what they’re attempting to do is provide free interview practice to HBCU students. If you know anything about interview prep in these days and times, it can be very expensive. There are some companies and organizations out there that are just charging obscene amounts of money to provide candidates… to kind of prey on the hopes and dreams of candidates who are looking to crack FAANG companies.

Anthony D. Mays:
But Karat wants to provide free interviews to Black HBCU students and to help them level up in their careers. And I love that because I remember how difficult it was for me to connect to good and reliable resources, and I think this is such a wonderful opportunity for our students to finally get feedback and support that they may have been lacking before. And so, I’m really excited about that program. I’m really excited to see it grow and expand.

Anthony D. Mays:
I think that this is one of those things that if we get this right, it will really take off and be a substantive force in the industry. So that’s what I’m excited about, and I’m really excited to continue to partner with them to grow and expand the impact of that program so that, though we may be focused on supporting Black engineers today, that this is something that will be opened up for everybody in the near future. Yeah. That’s what I’m looking forward to.

Maurice Cherry:
When you look back at your career and you even look now to where you’re at with your firm and with your family and everything, what does success look like for you now?

Anthony D. Mays:
For me, the measure of success has remained constant. It’s how well do I reflect Christ in my life, is really what it comes down to. And I think that being able to continue to support for my family and take care of their needs while also providing transformative impact on the industry in which I’ve grown up and become accustomed and have grown in, that’s key for me. And so, I want to continue to amplify and multiply the impact that I’ve had in tech to help more people get in and succeed.

Anthony D. Mays:
My hope is that, by doing that, I can leave a good example and legacy for the generation that’s following after me, because I’m not just an observer of Black history. I’m a participant in it. And I’m continuing that legacy so that future generations will benefit.

Maurice Cherry:
Where do you see yourself in the next five years? What do you want the next chapter in the Anthony D. Mays story to look like?

Anthony D. Mays:
Yeah. That’s a really tough question. That’s been on my to-do list to answer that one. I haven’t quite gotten around to it in the two months that I’ve been a full-time entrepreneur. But I think just real quickly, I hope that in five years, I’ll be reading a news article about how my efforts has transformationally changed the tech interviewing landscape, that I want to be able to, in five years, read that article, that I want it to be said that, through the work that I did, I was able to help this industry almost leapfrog in terms of how we deal with and grow and develop underrepresented talent in the business. So that hopefully will be my contribution, but we’ll see.

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

Anthony D. Mays:
Yeah, absolutely. So I’ll make it easy for all of your listeners. Anthony D. Mays, D as in diversity. Anthony D. Mays, M-A-Y-S, on all the things, Twitter, Instagram, LinkedIn. Feel free to connect with me. I’m also at anthonydmays.com and that’s a great place to find articles that I’ve written about tech interviewing, working in tech, being underrepresented.

Anthony D. Mays:
If you want to book me for speaking, I’m also there. Yeah. You can also connect with Morgan Latimer Consulting right through that page. So it’s all there. Just visit anthonydmays.com and connect with me. I’d love to chat with you and figure out how I might be able to help you in your journey and your career.

Maurice Cherry:
Sounds good. Well, Anthony D. Mays, I want to thank you so much for coming on the show. I mean, I had a sense, from doing my research, how the interview would go in terms of your story and what you’ve put out there. But I guess I didn’t realize how similar in a way we were in terms of how we got into technology, growing up in, like I said, these dubious towns and things.

Maurice Cherry:
I hope that people will listen to this interview and not only, I think, seek out your services, but see just where and how far passion can take you. It was very clear to me from listening to your story that you have this passion for technology that would not quit, and to the point where it not only got you to working at one of the top tech companies in the world, but that it also, in a way, started a journey of self-introspection to get you to where you are today to be just a stronger and better person. So thank you so much for coming on the show, man. I really appreciate it.

Anthony D. Mays:
Well, thank you so much, Maurice. This has been quite a pleasure.

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brandon Viney

If you’ve seen either the the “Black Girl Magic” video or the Black History Month video this year from Google, then you’re already intimately acquainted with the work of Brandon Viney, group creative lead at Google Brand Studio. He heads up the creative agency inside Google that uses data from the search engine to produce powerful ad spots like these (and many more).

Brandon gave a peek behind the curtain on his creative process when starting new projects, and talked about the Google Brand Studios Fellowship Program and shared what Google looks for when bringing on new talent. He also shared growing up in the Blue Ridge Appalachian mountains of Virginia, attending VCU’s world-renowned Brandcenter, and reflected back on his time working in advertising at Wieden + Kennedy. Brandon is definitely one of the most down-to-earth and humble guests I’ve had on the show in some time, and I hope his story inspires you to push the boundaries of your creativity!

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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I’ve had my eye on Chikezie Ejiasi and his work since we profiled him for 28 Days of the Web back in 2015. Fast forward to now, and Chikezie is working as a senior interaction designer at Google on their new Daydream VR platform.

We had a lot to talk about! He shared information about Daydream and why virtual reality is becoming so popular right now, his “anti-conference” stance, and how not following a traditional design path helped set him up for success today. It’s a great conversation that I’m sure you’re going to enjoy!

(Thanks to one of our patrons, Nate Koechley, for the introduction!)


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Revision Path is sponsored by Facebook Design. No one designs at scale quite like Facebook does, and that scale is only matched by their commitment to giving back to the design community.
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Revision Path is also sponsored by Hover. Visit hover.com/revisionpath and save 10% off your first purchase! Big thanks to Hover!
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Revision Path is brought to you by MailChimp. Huge thanks to them for their support of the show! Visit them today and say thanks!
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It’s been a minute since we’ve had someone at Google on the show, so I was really excited to have the chance to interview Melissa Smith, a user experience researcher at Google working primarily on the YouTube mobile and desktop products.

We talked about how user experience research factors into her work, why it’s an important part of the design process, and talk about how she shifted from studying engineering towards her current work. There’s even a conversation about self-driving cars! It’s great knowing women like Melissa are at the forefront of helping make better experiences for all of us online!

(Thanks to one of our patrons, Nate Koechley, for the introduction!)


rp_patreon_banner


Revision Path is sponsored by Facebook Design. No one designs at scale quite like Facebook does, and that scale is only matched by their commitment to giving back to the design community.
fbdesign_logo_75
Revision Path is also sponsored by Hover. Visit hover.com/revisionpath and save 10% off your first purchase! Big thanks to Hover!
hover_logo_75
Revision Path is brought to you by MailChimp. Huge thanks to them for their support of the show! Visit them today and say thanks!
mailchimp-logo
Revision Path is also brought to you by SiteGround. Save 60% off all hosting plans by visiting siteground.com/revisionpath. Excellent!