Dec. 20, 2021

#26: The journey from "Hello World" to major tech executive ft. Nick Caldwell

My guest for this episode is Nick Caldwell. Nick and I talk about what motivated him to get into the tech space, what it takes to become a Black Executive and what he calls the happy to be here mentality when it comes to staying in a Tech shop for far too long. Nick Caldwell is a Tech Executive, Speaker, Angel Investor and is currently the General Manager for Core Technologies at Twitter. He previously worked at Microsoft for 13 years as General Manager of the Power BI product, was Chief Product and Engineering Officer at Looker (acquired by Google) and VP of Engineering at Reddit. Nick’s charitable work includes being a board member for /dev/color: a non-profit whose mission is to maximize the impact of Black software engineers, and founding Color Code: a scholarship fund dedicated to future leaders of color in technology fields. 

Here is a snapshot of a few things we talked about…

Introduction [01:40]

What Motivated Him to Be a Lifelong Learner? [03:15] 

When His Mom Brought the “Drill Sergeant Discipline” Home [05:29]

When Did He Realize that He Should Move to a Better Place and Find His Group? [09:44]

How Did He Deal with Being an Outlier with All the White Faces Around? [12:47]

How to Overcome Challenges and Try to Reach the Top as a POC? [19:02]

Important of Representing your Professional Self in Public via Networking Sites [24:49]

Why Did He Stay at Microsoft for So long? [27:58]

What Made Him Realize That it was Time to Move on From the Current Company? [34:15]

How Not to Fall into “Just Happy to Be Here Syndrome” Trap? [37:07]

What Was it Like for Him to Jump from Working at Smaller Companies to Way Bigger Ones? [39:45]

What is It like to be the VP of Engineering? [43:26]

What are His Favorite Twitter Hashtags or Topics to Follow? [45:55]

What are His Future Plans about Starting a Tech Company? [47:02]

Key Takeaways...

(Show notes from our interview have been edited for clarity and brevity.)

  • “My dad was just and continues to this day to just be a voracious learner, so he wanted to teach me how to play chess, teach me how to play instruments, sports, all sorts of different things at a very young age…”
  • “It's very hard to bucket me into one particular skill set or interests…”
  • “If you don't like what you're working on and you just wait three months, there'll be something new that everyone's going after…”
  • “My mom was a first-generation Jamaican immigrant, and she was very clear to me that academics and output were going to be the way to prove myself and get to a better life, a better future…”
  • “I was an early Internet user, and I was able to see just how much opportunity was out there and all the different people that you could meet out in the world…”
  • “One day I'm walking home, and I see this poor kid, like get jumped by a gang. I really got messed up. I want to find a place like where I don't have to deal with this…”
  • “I'm tired of pretending. I'm just going to be what I think good looks like. I want to really settle in on my dreams and just commit to them and see how far I get as opposed to trying to blend in and be someone else…”
  • “If you're going to be a Black Technologist, that is the norm that you will be, unfortunately, you're going to be the outlier…”
  • “What I caution people is you have to find ways that this doesn't drive you crazy…”
  • “To be a VP requires significant experience and you have to not be afraid to try a lot of different things…”
  • “You have to have made successes and made mistakes, but you don't get to be on deck for an exact opportunity unless you can be trusted with extremely good judgment and building organizations, building software…”
  • “The key challenge to people of color is these positions. It's not like you go on like LinkedIn and you type in, I want to be a VP of Engineering and you'll get like all of those options. Those opportunities are typically run in private…”
  • “Making your personal brand and story available online and contributing in that way with many to one, networking is radically more powerful…”
  • “Whatever platform works for you, be comfortable talking about yourself in public and celebrating your successes and wins…”
  • “Internet can be a scary place. The positives far outweigh the negatives…”
  • “When you take control of your career in the form of being willing to take risks and being flexible, simply put like more opportunities come from you...”
  • “Don’t be afraid to try new things if you want to be calling yourself an entrepreneur and an innovator…”
  • “Once you can prove that you know how to operate comfortably, that six-figure salary, starting salary is truly the starting salary and that there is no limit to how far you can push this thing if you're willing to take on the risks, try new things and so on…”
  • “The things that I learn, success or failure simply multiply out the opportunities. It's like the landscape just keeps getting bigger and bigger the more things I try…”
  • “Twitter still feels like a Startup. It's not as chaotic as what I just described. But Twitter is not a big company. Twitter is going into an expansionary phase now, which is fun…”
  • “I enjoy seeing people who want to be themselves in public…”

Where to Find Nick


Twitter: @nickcald



Kimmiko James  0:00  
Welcome back to another episode of The Black Enterprise Network podcast. Before we get into things, I just want to spend a few moments talking logistics and where I've been because it's been a while, in all honesty, I've just been struggling mental health wise. And that's all I really have to say about that to be honest, because when you're not mentally well, it's hard to function and do things productively or consistently. I can't say that for a fact, things are slowly getting better. And with that episodes will be published more gradually as well, hopefully shooting to do one to two episodes a month to start. But I don't really want to make any promises about that given I've made a lot of promises for this podcast that I have yet to keep up with. What I can promise, however, is that this podcast won't be dying permanently. I appreciate everyone that still binges, the older episodes, people that send nice messages about how you like the show, and how it inspires you and so much more. I also need to get through guests request too. So if you reached out about that I'll get to you soon. I just really need to prioritize current guest episodes that are backlogged. If you're a guest listening to this episode, I'll reach out to you soon about the logistics of your episode. And yeah, that's all I have to say for that. Thanks again for your continued support and your patience. I hope you enjoyed this episode and future ones coming soon. Thank you. Yeah.

Nick Caldwell  1:21  
People look at me in my career, and they go wow, look at all these things that this person has done and been successful. But it was a 15 year journey at Microsoft plus I got an MBA to try to convince myself to leave plus. These other situations, which made me want to edge out the door took a lot to dislodge me.

Kimmiko James  1:40  
Nick Caldwell is a tech executive speaker, angel investor and is currently the general manager for core technologies at Twitter. He previously worked at Microsoft for 13 years as general manager of the Power BI product. He was chief product and engineering officer at Looker, which was acquired by Google by the way, and VP of Engineering at Red. It also is involved in charitable work, which includes being a board member for dev color, and founding colorcoat, a scholarship fund that's dedicated to future leaders of color and technology fields. Let's get into the episode. Hello, and welcome back to the Black Enterprise Network, the podcast that shows the stories of black professionals and tech in entrepreneurship. In this episode, Nick and I talk about what motivated him to get into the tech space, what it takes to become a black executive, and what he calls the happy to be here mentality when it comes to staying in a tech job for far too long. The first thing I kind of want to get into which I thought was really interesting in your article was the three motivations that define your your life, your adult life, especially. The first one was that your father was exposing you to many different things and bringing you home different things you could play with as a kid. A second thing was the experience with your mom being a principal in the public school system. And you know what, she was very strict. And then the last thing which I kind of interpreted as the last thing was Maslow's hierarchy of needs in which, you know, when you were kind of walking through your neighborhood, you saw this kid kind of get beat up and that kind of triggered something inside of you to kind of just get out of those situations moving forward. So

Nick Caldwell  3:13  
yeah, beat up you got to watch really beat up pretty devastating fight there. I think each of the three motivations there's there's other things, but I think those are the highlights my dad was just in continues to this day to just be a voracious learner. So wanted to teach me how to play chess, teach me how to play instruments, sports, all sorts of different things at a very young age. It's like they just kept throwing more and more and more activities at me. And, you know, that kind of translated into me into being sort of a lifelong learner, even to this day, it's very hard to bucket me into one particular skill set or interest. You know, my title right now is VP of engineering, but I've also been Chief Product Officer, I've run product marketing of design and security, I just continued to be passionate about learning as much as possible. If you're in tech, that's great, because it's always changing. Like one of the fun things about this industry is if you if you don't like what you're working on, you just wait three months, it'll be something, something new that everyone's going after. And I think about what I was working on early in my career is radically different from what I'm doing now. And all in good ways. You do need to be be able to kind of work hard and find ways to say hustle that seems to be a negative word nowadays, but like hard work goes a long way. And my mom was a first generation Jamaican immigrant and she was very clear to me that academics and output were going to be the way to prove myself and get to a better life a better future etc. And you know, she was both strict and also just overwhelmingly supportive. So all of these different activities I was trying to do, good or bad, you know, she was supportive of whatever I would try the guy at one point I was on a basketball team for like two weeks. like to give you an example. And my mom was, you know, fine when I quit and decided to do something else. She's also fine when I woke up one day and said, Hey, actually, I really love programming. I'm gonna stop all these other things. And I dropped a lot of hobbies and refocused on computer. So it helps to have someone in your corner and someone who's going to motivate you and hold you accountable. And and keep pushing you.

Kimmiko James  5:22  
Your mom brought home drill sergeant discipline. So what did what did that look like?

Nick Caldwell  5:28  
So my mom was a vice president of engineering at a elementary school. So she often terrified me sometimes, you know, if you don't know that role, that's like the disciplinarian role in a school. Like when kids are acting up, they bring in the vice principal to settle him down. And she could be quite terrifying, but she wanted to. But the way that sort of translated at home was more strongly encouraging good grades, the bringing home, the baby wasn't enough, why didn't you get the A, but on a more positive note, like she put a lot of opportunities in front of me when I otherwise would have kind of just been playing video games all day. And it was this kind of combination of like high expectations, with just support all along the way that I think was really valuable to me, because I failed at quite a few things like I don't want to take seem like my mom was a disciplinarian. And like, I had to succeed at every single thing, it was more that she wanted to make sure that I was actually trying and like for anything that I really wanted to do that I took, you know, it's hard to swing of it as I could, and held myself to a really exceptionally high bar. And the reason for that is her being a first generation immigrant was the beginning of that, like she came to the United States with a whole beginning education and finding a better future and building a better home for herself. And that same sort of mindset and discipline transferred to me, and hopefully, I've done a decent job, she sees me pretty happy. And then the third thing was, yeah, you know, at a certain point, it wasn't just that fight that you mentioned that that did bring it to a head, but like in my youth I was running, were called bulletin board systems are like kind of pre internet systems that allowed me to talk to people around the country, or in some cases in different countries. So it was a combination of two things like at that age, I was an early early Internet user, and I was able to see just how much opportunity was out there and all the different people that you could meet out in the world and how many different interest there could be. It was like, there was a whole world out there ready to explore, and I was getting just a tiny piece of it in my little suburban neighborhood where there were no other geeks, there were, I was sort of in a friend group that, you know, their ambitions were related to like NBA and football. And here I am, like reading PC Gamer and talking about Wolfenstein and Doom it you know, it's you got to find your tribe to be happy in life. And I think that's true for everyone, like you're just gonna live better existence, if you can find a tribe of people that you vibe with? And secondarily, yeah, there was some anti academic shit going on in my school. So yeah, one day, I'm walking home and I see this more kid, like get jumped by a gang, I really got messed up, I want to find a place like where I don't have to deal with this. And I'm going to work my ass off to get to a better school district. And I dropped and it was literally within two weeks of that event, like I dropped all of my hobbies other than the one I thought that would give me access to new opportunities like computer science. And then there's sort of a sa t sort of precursor test you take if you're in Maryland, I think I forget exactly what it's called. But I only did that for like the next four months, I just coded and I studied this sad thing in preparation for the for the test was was able to kind of get myself into a new school district afterwards. And you know, I won't say that was the the end of it. I did a lot more hard work after that. But like, everyone's got to drive motivation from somewhere. Like if you're coming from a less fortunate background, like it's not any surprise that that motivations to get yourself into a better station in life, be through money, location, etc. And I'm no different in that regard. Makes me wonder though, when I have kids now we're pretty well set. So when we when I have kids, I wonder what I'm going to do to motivate them.

Kimmiko James  9:19  
A follow up I had and you kind of already touched upon it is like how did you know that you just had to do something, especially at such a young age because you know, where I come from also kind of not the best neighborhood. And then kind of same for you. It's common to see people that live around you or your friends with just stay in the same place. They're out even into adulthood. And they just never leave. So how did you know? I mean, how old were you at the time?

Nick Caldwell  9:44  
I think I was well, that was like a 12 or 13 I think by that point like I'm skipping over my entire youth in this story. That's okay, that's okay. You have to remember like leading up to this decision is my whole childhood is just Being a Black Nerd in a deeply non supportive, nerdy environment for nerds and just feeling sort of where am I people, like I'm feeling isolated here. And, you know, I'd be lucky if I could find someone else who was into computers, I know sounds baffling, like in today's day and age, but like, when I was this age, people had literally no idea what the internet was, or that or what coding was, If I would to go and say, Hey, I'm spending my afternoon learning C++. It's like, I might as well be speaking Japanese. People just didn't understand it. And like, Here I am, like a young black dude, coding watching anime I'm on BBS is like this generation of like, oh, yeah, whatever. But like, at that time, you were much more expected to sort of be in the sports or spending your time outside or going to the mall, if you remember, that was a thing. So that was the precursor, all this, like, I had been operating differently for some time. And I just needed the spark to be like, hey, look, I'm just gonna lean all the way into this, like, I'm tired of pretending I'm just gonna be like, be what I think, good looks like, I want to really settle in on my dreams and just commit to them and see how far I get, as opposed to trying to blend in and be someone else. And that's something that's carried with me for a long time, I think I have to be cautious because I try and tell people to do this. But in my aged wisdom, I now realize like what a dangerous thing that is to say, like when you tell people just be yourself, even if it comes at the at the cost of not fitting in and so forth. It's certainly takes a heart and fortitude to actually live that way. And for me, I've been fortunate and had not only done it, but had people supporting me in it. But I also acknowledge that it can be sort of exhausting to live that way. And sometimes it is easier to just like, hey, I'll go along with the crowd. But that's just not me. Like, I think people who are really successful end up being you know, not they're outliers, by definition. And then when you ask them, why they generally acknowledge it that like to get where I am, I had to take risks, or do something different, or stand out from the crowd, or put another way, just like take a bet on yourself. And I've been fortunate to do that a few times in my life now. And it's worked out,

Kimmiko James  12:15  
you kind of just talked about how, you know, you're more of an outlier for most of these things. And especially for you, getting into college, going to MIT, and even getting your MBA, I'm sure you felt kind of occasionally like an outlier with all the white faces around you. And let me kind of just quote here, you considered white people to be unicorns compared to what you were usually used to back in your old homes, and you just kept your head down at work. But how are you just able to do that, because it's gotta be very awkward and uncomfortable.

Nick Caldwell  12:47  
Yeah, I mean, that's not an uncommon situation. I mean, if you're gonna be a black technologist, that is the norm that you will be in, unfortunately, you're going to be the outlier, typically, the only black person in the room, some companies are doing better or worse at that, but like, it's definitely going to be the next generation, I think, is going to have to really solve that. But if you want to navigate it, like what I kind of found myself focusing on was the not so much the people I was directly working with, but the potential for the outcomes that I could have. And that sort of kept me centered, whether it was I'm in MIT, or you know, my first job at Microsoft, where I was the only black end engineer for a very long time, that the reward of it was the impact of my work and getting to see code that I'd written be used in the real world by 100 million people. Like that kept me motivated, but it wasn't a solution. You know, this is like a BandAid on a wound that like, eventually you got to find your tribe and be able to really connect with folks. So it wasn't until I encountered deaf color that I really understood what it would be like to be in an environment where there were other people like me, and the feeling that you get from having a community that understands your challenges. And not only that, but is there to support you. But up until then, like I had to keep my head down, focus on the work in my own skill and improving my own skill set. And then showing that like I could produce results and being satisfied with that dimension of the problem. And then unfortunately, like the other dimensions of this problem, which are around finding community, and so on and so forth. If you're in Seattle, and you really want to have deeply connected sort of black technologists community, I'm sorry. Like there's only so many of those people in that state and it will be that way for some time. So you have to find other ways to find community either, you know, outside of tech or what have you. But you have to do anything, whatever it takes to get that support group. Being a tech is hard regardless, right? It's like this is a very stressful industry, particularly as you're coming up, right? You know, it's hard regardless. So you have to find your some way to get support, but you also have To be practical, and I see a lot of unfortunately, I see people of color kind of burnout for lack of a community of tech people who are right there with them, you have to find a different way. Like if you're in a company I was at Looker previously, right? I was the only black engineer at Looker get that opportunity was one of the biggest things that ever happened to me in my life. So I could have said, Hey, I'm going to pass up this opportunity, because it's missing this aspect that I really enjoy. Or I could say, hey, look, it's a trade off, right in return for missing this dimension of what I like I'm going to get, you know, these other like very positive things, I'm going to have to acknowledge that upfront, make the trade off, and then find ways to compensate for what's missing. And for me, I used to have color to compensate for what was missing. But I didn't expect overnight that the company would solve this for me, I tried to be part of the solution, knowing that going in, was going to be worked to solve that. And then in parallel, I got to take advantage of all these other great opportunities, and it worked out quite well. And I think for people of color, it's unfortunately always sort of navigating this trade off dance, there are no companies, I'm aware of that in tech anyway, that give you the perfect product, a diverse team, the pay is right, it's in a location that you want. There's nothing that I'm aware of at this point. So we're always sort of making trade offs. Do I tell people you have to acknowledge that going in, like, take the trade off. Also, it's great if you can find a way to make some improvements. When you get into these companies, you know, hiring more black people, if you're someone like me, who's a hiring manager, or if you're not a hiring manager, participating in the employee resource groups, but finding a way to compensate for what's missing as you go. But also acknowledging that this problem is not gonna be fixed for you can't come in with the mentality that like, hey, it's only going to be a year or two and everything will be fixed. This is a mountain top level problem may not get there with you. Alright, I'll go as far as the walk as I can. Companies are getting, like, particularly since BLM put so much attention on these sorts of issues, like Yeah, companies are getting better quickly. But there's still a ways to go. And slack is one of the better companies Twitter, I've been at Twitter for about a year. Now Twitter's phenomenal. There are some Hallmark examples of companies that are doing a great job here. But if you look broadly across the industry, you know, just look at the statistics and aggregate, it is more common that you will be the only when you join one of these companies like that, that is the predominant sort of mode you'll be in. And you have to get put into so many odd conversations and odd positions by being in only in a company. And again, it's like you kind of expected going in. And what I caution people is just you have to find ways that this doesn't drive you crazy that it's going to be an added burden for a person of color, or sorry, I'll say this is also not restricted to people colors is also there's other dimensions as well, you know, I think you being in technology adds even more complex dimension to this. So you got to know it going in, I like to work at places which acknowledge these issues and are working toward solving them, and then be a part of that solution. And then also, like produce great work, but build great products at the end of the day. Like we're all in Tech because we want to build things for the world and see our products used. And if you aren't getting maximum enjoyment out of that, like you might even run into issues. So you know, I'll leave it there.

Kimmiko James  18:24  
Yeah, yeah, very well said. But a follow up, I kind of wanted to ask is, so there's people that are very passionate about tech, right? They try out software engineering, they try out PM, or maybe they're just really in love with software engineering, and they want to get to your point, let's say. So hypothetically speaking, if I wanted to be VP of engineering, as a black woman in tech, what would be the main piece of advice you would give me to kind of figure out how I could get there because it's not easy, per se. And we don't really see that many black women in VP or President CEO kind of spots at these companies. Anyway.

Nick Caldwell  19:01  
Yeah, exec roles are particularly difficult here. So there's sort of a baseline bit of advice, which I'll give you, and then I'll tell you what the hard part like to be a VP, it does require significant experience. And you have to not be afraid to try a lot of different things like when you think about exactly exactly as someone who final decision making roles up to. And to be put in that position, you have to have tried a lot of different technologies tried a lot of different ways to manage your organization, you have to have made successes and made mistakes, but you don't get to be on deck for an exact opportunity. Unless you can be trusted with extremely good judgment and building organizations building software, etc. So that's sort of the baseline for any anyone who would be considered for an executive position. But I think what you really asked me here is like, hey, what about people of color? So the key challenge for people of color is these positions are it's not like you go on like LinkedIn and you type in I want to be VP of Engineering and you You'll get like all of those opportunities, those opportunities are typically run in private, if you want to be CTO, you know if a company's posting that like their C level executive is about to leave on LinkedIn, that sort of sends a bad signal to the market. So you go, Okay, well, how do you get access to these opportunities, then, if not, through traditional means, like LinkedIn, it's through networking, executive networks, being connected with other execs, etc. And having a good reputation and track record within those networks is what makes those opportunities come to you. So for my job in Twitter, or when I was at Reddit or those CPO job, I wasn't on LinkedIn applying to those things, those folks reached out to me. And the way in which that occurred, the spark, which allowed me to get into those networks were a combination of being connected to the exec recruiters, not regular recruiters, as well as knowing people at those companies, right. So it's like your network. Over time, when you become further and further in your career, your network becomes your net worth, all of your best opportunities will come from it. Now what's missing for people of color is access to those networks. Like when you're coming up through your career, having the ability to know who to go to for exact recruiting opportunities, or knowing other execs who are majority, not people of color becomes a very significant disadvantage. So the way that like I believe you close this is not super complicated. It's you look for people who are on a trajectory to exact rules, and you simply tell them like the last mile connection to do the to make to get access to those opportunities. So I'm on the board of a company called aboveboard, and its whole mission in life is essentially to connect diverse up and coming potential execs with these sorts of opportunities so that they don't have to discover how to connect in an organic way. This is how I discovered it, like kind of through happenstance and asking the right questions to the right people and looking into it. Rather than that, let's systemically find ways that we can connect potential execs with those opportunities, and make the networks available. The other thing I think's important here is for people who are execs already extending a hand and opening the door to the up and coming generation, so that it makes it easier for them to build their networks as well. So this is like depending on how you want to call it like it'd be sponsoring to be mentoring. But the main thing is sending the ladder back down to bring people up, like particularly if you're a person of color, who's made it into an exact role, I think is super important as serve as an example for how we want the next generation to act. So ultimately, like we have to find ways to connect people those opportunities, and that comes from some work that individuals need to do on networking. But it also comes from making those networks more accessible in general, like, you know, you don't want to have these great wealth generating impactful opportunities, hidden behind closed doors, we have to find ways to shed some light on those things. Yeah,

Kimmiko James  23:07  
yeah, very well said. And kind of just going back to the code path, black excellence, talk you gave something that I kind of wrote down was, you said that your network matters more than code, tech changes quickly, but the network and relationships don't. And for me, that was powerful. Because I was obsessed with the code. The first two, three years, I was getting into the industry, I didn't really pay attention to the network. And you know, after a while just getting recruiters emails and their business cards, I never really followed up, or even doing coding, practice coding interviews with other people with those engineers, I never followed up and honestly, looking back, I kind of regret it, not because I'd need something from them again in the future. But because they probably would have brought so much more value if we would have kept that relationship kind of going. So I agree with you wholeheartedly. It's the part of the person AKA a student like me, for example. But also it's kind of the accessibility part too.

Nick Caldwell  24:02  
Yeah. And you know, you have plenty of time to do that, by the way. I think that start as soon as you can, but you're definitely not missing the boat here. I think the the first couple years of my career, I same thing, like you know, I think the first five years of my career were completely heads down, just trying to have as much impact as I could, and learning the craft of being an engineer. But things didn't really take off for me until I kind of pop my head up and then realize that like it's actually quite a village that is required to ship software. It's not just engineering like I went and spent time with a product person first because they were the nearest person I could ask like, what's your day like, you know, QA then I met some people from legal and I found that over time, the more of these other functions I understood, the better I became as an engineer and the better I became as an employee. The other thing I would kind of encourage you to do if you truly believe what we're saying here with with networks become your net worth over time is the power of many to one networking that in the olden days networking was like, Let's go have coffee, you can have really powerful networks if you do that one to one. But with Twitter or tick tock tick tock, even I've seen people do this on tick tock, making your personal brand and story available online and contributing in that way. And with many to one networking is radically more powerful. And it's surprising how few people really lean into that, because there may be shy about, you know, being on social and so on, so forth. But it's a superpower. Like if you didn't get good about representing your professional self, self, and I don't mean being fake. I mean, just showing what good work you do in public, if you can get comfortable with that. It adds a whole new gear to your ability to network and get opportunities, and so on and so forth. So don't be shy about that. I use, you know, primarily Twitter for that, but I think maybe the next gen wants to do this on Tik Tok. I don't I don't know.

Kimmiko James  25:55  
Oh, no, no, I mean, so I'm Gen Z. I like missed the millennial thing by like, maybe a year, some months, but most of us do use I think it's Facebook is the one that's dying out, like everyone I know, uses Instagram, Twitter. And honestly, LinkedIn has been growing in popularity to share anything and connect with people, surprisingly. So

Nick Caldwell  26:16  
I use Facebook to stay in touch with my grandma. And LinkedIn is like, I've still not quite figured how to use I have like a ton of followers on LinkedIn, I still have, I've not like come round to truly enjoying it. I feel like every time I go on there, someone tries to sell me something. Yeah, but same. But anyway, try it out. The main thing is like whatever platform works for you be comfortable talking about yourself in public and celebrating your successes and wins. And like you put that in the world, it'll come back to you. I've just noticed that consistently, as someone who's responsible for health at Twitter, and also it was a response before that Reddit as well, I would caution like internet can be a scary place. But the the positives far outweigh the negatives. And I think we have a lot a long ways to go when it comes to systemically addressing online harassment and things like that. I think that the misuse of social media platforms is to my mind, one of the things that we have to solve within next few years for, for the betterment of society. But that aside, the opportunity it affords people, the visibility that you can get about your podcast, or topics you're passionate about, means that it can be transformative, but if used correctly, you know can amplify your voice, it can amplify your opportunities, a hundredfold and we don't want to miss that massive benefit.

Kimmiko James  27:41  
So why Microsoft for so long? Does you know was it truly the safest bet that convinced you to stay for so long? And also I know that Bill Gates was your hero? I don't know if he's still your hero today. But at that time, it seemed like he was. Yeah, that's

Nick Caldwell  27:58  
a whole other thing we could talk about. I don't know when this is going out. But Bill, Bill is going through it right now. Let's do I could comment on that. So much to say, I'm sorry. I didn't mean to you. Not? I just have so many thoughts on that whole situation. But no. So when I started my career, one, I had been teaching myself Microsoft products. I bootlegged. And I don't know if you know what MSDN is. But like this was like back in the day like an incredibly expensive like several $1,000 dev kit that Microsoft put out. If you want to learn how to code on Windows, and I'd like bootlegged, it taught myself how to code Microsoft Word using the Microsoft stack for years. So I was familiar with it. And then when I went to school, I studied machine learning and NLP. And Microsoft had announced the creation of the natural language groups. It was one of the few places you could work at, that was explicitly focused on machine learning and NLP. And I got to interview for that as my first job. So it was also very safe, like a well known company. Google was around at that time, and I had some friends who were going as early employees, but as a startup, and I had tons of student loan debt. If I had gone to my parents had me like I'm gonna go work for option a Microsoft well known company, six figure job option be like randos startup named Google, what the hell is a Google? They would have? Yeah, they would have looked at me like it was insane. Now, I didn't take that risk early on. And I found a good home where I had a I mean, it was a really great career for many, many years. And I stayed because I was successful. I enjoyed it. It was lucrative and Microsoft creates a great environment has challenges, big companies, you know, I could enumerate all of the challenges that Microsoft had, and Amazon and, and Google all have very similar sort of big company challenges, but if I'm being honest, I learned a ton, surrounded by great people felt supported by my managers, and they create an environment that makes you Want to stay and that way. But the problem with that is, is you get locked into a single worldview. And to this day, I know people who have been Microsoft for 1520 years, and they're like, tangibly afraid to try something different. And it's like that Microsoft environment has become their universe, not just Microsoft, you see this with lots of big companies, people who just get locked in and like they, they get familiar and comfortable with all the people the technology stack and the way that that business runs, and they're decided they're going to run their whole career that way. But I'm an innovator at heart. And it was only a matter of time before I realized that trying to be an innovator inside a big tech company is not necessarily the best fit. Like I'm a bit of a troublemaker, I like to do new things. But I was a bit of a afraid, so I stayed one, I was having a good time. But if I'm being honest, I was afraid to make that leap and try something different to a whole new universe. Ultimately, it was a confluence of events, which allowed me to make that switch. One is I had a good friend who left Microsoft and went to a startup called square. And this dude made like $3 million in one year. Whoa, what the hell, like you'd left last year, and now you're buying freakin 5000 square foot pumps, I was like, Wait a second.

This seemed to pay off for him. The second thing is I had been promoted into a job, I was running dynamics ERP. I don't know what that is. But essentially, it was like a product that like it was a much bigger team. But then when I started to use the product, I realized I didn't actually feel passionate about it. So I was like someone else who's really passionate about this ERP space should probably take an opportunity to run this team. And then the final thing was, Steve Huffman, from Reddit, reached out to me and talked to me about the the Reddit platform VPN, avenge opportunity. And earlier, I mentioned that like, you know, my earliest days were in computing were on BBS is, and, you know, social networks of that generation. And I've been a redditor for a decade at that point. And I was like, you know, what, I actually love this space. Like, if I think about something I could get really passionate about, that would be worthwhile taking the risk. From a what I would learn perspective, from a financial perspective. You know, what, screw it, I'll do it. And, you know, I took the leap, and it worked out really, really well. But it was a 15 year journey at Microsoft plus, I got an MBA to try to convince myself to leave Plus, these other situations, which made me want to edge out the door, it took a lot to dislodge me. And now that I'm dislodged, I should I should have done that bar earlier, when you take control of your career in the form of being willing to take risks and being flexible. Simply put, like more opportunities come from you from an external vantage point, people look at me in my career, and they go, Wow, look at all these things that this person has done, and been successful at big companies, small companies, social products, data products, the more you can kind of paint this picture of your skill set, the better opportunities come to you. And if I had stayed at Microsoft only did that one thing, where I'd be now it'd be a Microsoft CVP, I'd have a instead of this t shirt, I'd be wearing a blue suit, brown shoes, I would be talking to you in a very robotic voice, we would be reading from a script, which had been prepared for me by my team of 30 PR people. And I would have to have editorial approval on this after you finished it. It's like a very sort of more rigid lifestyle that I was not in retrospect, you know, wasn't going to be for me. I'm glad I got off that track.

Kimmiko James  33:38  
Yeah, it's a common thing I hear from entrepreneurs that they spend maybe five to 10 plus years at a company. And then when I talk to them, they're like, Oh, I spend way too much time over there.

Nick Caldwell  33:49  
It's important to learn the ropes. I think I don't want to discount how much I learned in that environment. But at the same time, you gotta jump. You gotta Yeah, try. So try it again, be afraid to try new things. If you want to be calling yourself an entrepreneur, innovator.

Kimmiko James  34:02  
I think it's just, I guess, how do you just know I mean, the 1015 year mark, how do you just know that it's just time to move on? Was it just the lack of innovation you were experiencing? Or was it just you know, you're getting comfy?

Nick Caldwell  34:15  
Yeah, it was more getting comfortable. Like it wasn't lack of innovation. I was in Microsoft working on the equivalent of Microsoft startups, I worked on product called Power BI, which was internal sort of startup, it was more. It was a fight to do that. In a big company, you're always fighting innovators dilemma. And when it comes to building new products, or choosing different technological approaches, and so on, and so forth. In a big company, the motivations are a little bit different, you know, Microsoft, that time, you know, you're sitting on this gigantic Windows Office monopoly. And if you want to build a new product, the first thing that people are going to ask is like, hey, could this energy have been spent better by just improving the already existing multibillion dollar products? And you have to be willing to say no, Like this thing I'm working on is going to be another like gigantic multi billion dollar product, while internal forces are trying to prevent you from making that call. So you know, doing that at a big company for a long time, you know, I had some successes, I had some failures. When I switched to startup, it was like the opposite. It was like we're taking so many risks, we need someone who can like, who has been in environments that are more stable, and can show us the ropes when it comes to like scaling your organization or building a long term technical roadmap. So it was like all of those kind of skills related to stability, and does organizational design and mature products that I learned from Microsoft allowed me to come into startups and have a set of superpowers. And at the same time, I got to learn what it was like to run startups. And I think I've landed myself in a pretty good spot, like in terms of when you know, when is when like, when have you learned enough? It's tough. I think like, for me, if I start to feel comfortable, like I'm not challenged, or if not a little bit worried, that the thing I'm on is gonna fail, there's not that little hint of anxiety, that I'm not pushing myself, I start to wonder, like, should I be doing something else. And the thing I've added the difference over the last like five years of my career is, rather than limiting myself to like, Hey, I'm gonna look for another opportunity in one company, just kind of pop my head up and realize that Silicon Valley exists, or now that Silicon Valley with COVID, I think Silicon Valley is now spread across the country, there's just so many more opportunities if you're open to them. And I don't know what it was, but like it, because it took me 15 years to get there. Maybe you can save time, you don't have to spend 15 years. Just realize it after this conversation, but like, the more open you are to flexibility and learning new things, location, different companies, the more opportunities will come your way. And you just have to get good at evaluating those opportunities and taking bets on the right one.

Kimmiko James  36:55  
Yeah, I mainly asked for the young 20 somethings that I get offered the six figure salary. Nice things, and we'll take that off. We'll start there. Yeah, yeah, start there. But I think it's the start. Don't get stuck. Yeah, don't like you.

Nick Caldwell  37:11  
I think we talked about this before, but like, there's a trap you can fall in to called just happy to be here syndrome. So, you know, when I was at Microsoft, there was sort of an undercurrent of the reason I'm afraid of taking a risk and leaving this environment is that I might fall all the way back to where I started, you know, my home in PG County that like the six figure job that I gotten was the best that would ever be, you know, if your parents only ever made a combined income of like 30k. And then you find yourself as one person starting out with a six figure salary, it does some things to your head, like, Hey, I better not lose this job. So if you're getting a job stressful manager, bad you mentioned like having to kind of difficult manager, potentially, if you get on projects that you don't like, you might come back to yourself and say, Well, you know what, I'm just gonna push through it, I'm just happy to be here. Rather than telling yourself the truth, which is like there's, once you're in, you're in, like, there's lots of opportunities in this space. Once you can prove that you know how to operate comfortably. That six figure, SAS starting salary is truly the starting salary, and that there's no limit to how far you can push this thing. If you're willing to take on risks, try new things, and so on and so forth. But it can be painful to get out of that mentality that like coming from a disadvantaged background into an environment that throws me into a six figure job where I can buy any car, I want to live anywhere, I want to imagine that there's even more like that there's a whole other level of this takes a while to even understand that it's possible. So for me, same thing, like I put up with a lot of stuff, and really didn't come into my own until I realized that my knowledge, skill and abilities carry with me no matter where I go and get a bet on myself. And every time I've done that, fortunately, it's worked out. But more importantly, every time I've taken a bet on myself, just the things that I learned success or failure, simply multiply out the opportunities. It's like the landscape just keeps getting bigger and bigger, the more things I try. So now I'm doing like board memberships and angel investing, and I got on a public board early this year. And the opportunities just keep coming. So you have to just be willing to bet on yourself. Try new things. Not everything I've done is succeeded. But even in failure, what you learn, you just take to the next experience, and the opportunities just get that much more open.

Kimmiko James  39:32  
So what is it like being a VP of Engineering at Reddit when it was smaller compared to you know, now Twitter, which is obviously a really way bigger and way more structured, functioning company? Yeah. I

Nick Caldwell  39:46  
mean, Ben jump from Reddit. jumped to read it from Microsoft was pretty wild for me. So when I joined read, it was like 35 engineers and my previously my team was, I think we had like that dynamics team I mentioned was 700 people and And then my Power BI team was like 300 people. So I went from that to like a 35 person team. And it was absolute whiplash, good and bad. The bad, which I'll get out of the way was I mean, they obviously brought me in to help scale. So their operational processes like Job ladders, and how the release pipeline works. And using JIRA, and all of these things, you sort of take for granted, well established systems that bigger companies just like flat out didn't exist. And I was sort of expected to not only create them, but convince people that they matter at a startup that that can be difficult like trying to train people who've never like had formal management structure that there is value in management, and directors and so on my first week there I think someone asked me like, What does the VP of mg then do? Which kind of eye opening to dig? What exactly do you do here? Now the good of it was compared to Microsoft. Anyway, this is my first exposure to not just modern tech cycles, like AWS GCP. But more importantly, the knowledge and willingness that we had to change really rapidly. If you remember, like Reddit, five years ago, was this hideous,

Kimmiko James  41:07  
you know, like, it was kind of gross looking.

Nick Caldwell  41:09  
It was really bad. So there was a sort of top to bottom acceptance that like we needed to change lots of things really quickly, the UX of the site, the tech stack, we were using the, from the how we code, the data, layers, every single thing about it, there was so much energy to get going and try new things. I think in that first six months, I got exposed to more new tech than in the previous like five years at Microsoft. And it was amazing. It wasn't all easy and butterflies and roses, but incredibly fun to be in an environment, which was completely unconstrained when it came to taking large swings. And then so on, so forth. Now, Twitter's interesting in that, like Twitter still feels like a startup. It's not as chaotic as what I just described. But Twitter's not a big company, Twitter's going into an expansionary phase now, which is fun. We're adding better org structure and better tooling. And we're upgrading to systems like using GCP for data processing. And we're starting to bring in a lot more cloud tech, and it has that same sort of vibe that like people are like, yeah, we're about to change a lot. The differences Twitter has way more people and, and more funding this then. So if you're a Twitter user, you may have seen some of the outcomes of this over the past year, like the velocity with which we ship stuff has freakin skyrocketed. And I sometimes have to like rely on Twitter fans on Twitter posting about our new features to remember all the stuff that we're shipping. Like, we should like three things this week. I can't remember the stuff that's going out the door? I can't imagine it's a lot. Yeah, but it's a lot. But I you know, the energy is similar, that it's a company that has decided that it's time to expand and move quickly and take big bets. And, you know, I love that sort of environment. Also the impact too. I mean, you know, one fun thing about working in social companies is you get to see the fruits of your labor immediately used by hundreds of millions of people, and can be good or bad. But for the most part, it's good. And when it's bad, you feel it. You want to try harder next time. So I really am loving it so far.

Kimmiko James  43:15  
Yeah, thanks for sharing that experience. I always wonder what it's like to be VP of engineering, it sounds stressful. But it does seem like a pretty cool job to just touch all these different facets of engineering and working with people.

Nick Caldwell  43:26  
Yeah, no, it's incredibly fun. I think this stressful. Stress comes from being the final decision maker for a lot of things. And by the time you're VP of NGO, kind of accustomed to like, you have to sometimes make the final call for your team. But when you're VP of energy, it's like very impactful, things sort of roll up to all the simple stuff sort of gets solved deeper in the org. So put her we're having really impactful conversations about which tech choices to make on AWS or GCP. I get nervous, I pick the wrong thing, then like does that result in you know, 200 of my poor engineers being suffering through some strategic decision that I incorrectly call this like that sort of anxiety, the weight of the decisions that you make carry out through the entire organization, and ultimately, like anyone who's in management is trying to create the best possible environment for the company for the teams, they want people to come to the environment, love their co workers love the tech stack, etc. But this is a constantly changing configuration. As the company scales the people scale is as you build more products, the tech landscape changes and you're always trying to keep this in balance. It's an unstable system. So the anxiety comes from like just always wanting it to be as best as possible, but knowing that you have to continuously be open to change.

Kimmiko James  44:44  
So I'll say because I was gonna ask you are you feeling comfortable in this role, but it sounds like you're not so

Nick Caldwell  44:50  
now we got a lot to do. I think with Twitter, it's like we're shipping a ton of new stuff. I'm personally also really passionate that like those things get shipped in a way Good for humanity. So Twitter as a whole, when you talk to people who work here, very, very mission oriented, they understand the impact that the platform has on the world and wanting to not just create cool things for people who want to tweet timelines and be able to use spaces and tweet things. But all of that has to be made available and as healthy away for the world as possible. So there's no social platform or where who has solved this. So for me, like the job ain't done until we can do all this cool stuff and have it be available in a way that serves the good for the world. And I think that mission, serving the public conversation, but also making it available in a way that is good for the planet is sort of instilled in every Twitter employee that I meet. So we'll be working on that for a while.

Kimmiko James  45:42  
Love to hear that that's a tough problem to solve, but it's a unique one. So I'm happy to hear that you are passionate about it and not not comfortable force. What are your favorite Twitter hashtags or topics to follow?

Nick Caldwell  45:56  
Black Twitter warriors, and let me think I really like the positivity from Dionne Warwick 's Twitter handle. I know Chrissy Tegan is getting a lot of shit right now. But yeah, I also really like to follow her because of how genuinely authentic like she, you can love her hater personally, but she's really authentic. And, you know, I enjoy seeing people who want to be themselves in public. And this is a obscure one. But like, when I was growing up, there used to be a show called Beyond 2000. And it had a host this is a show about future technology. And one of the CO hosts was Soledad O'Brien, who went on to be like a CNN anchor. And now she just is on Twitter dragging people. It is, it is just like a guilty pleasure to know that this person I grew up like idolizing from a tech perspective is just on Twitter, dragging people for being bad actors. So that's all my favorites.

Kimmiko James  46:56  
And the last lightning round before we finish off would be in the near future. Do you see yourself starting a tech company, Bob in

Nick Caldwell  47:03  
the near future, like right now I want to buy right now I'm quite busy. Like I really enjoy working at Twitter. I've got three board roles, and I'm on. And I'm an angel investor in I think like 40 companies now. So right now I got my hands full. I think I wouldn't really have for the future if I could get really passionate about you know, some particular challenge and get a unique angle on it that I thought would have potential product market fit. I think I'd take a swing at it someday. But right now I'm just having too much fun.

Kimmiko James  47:32  
And that's all I have for you Nick. It was a pleasure having you on if people want to follow you check out your work. Where can they do that?

Nick Caldwell  47:39  
Yeah, sure. I mean, just go on Twitter. My handle is Nick called in IC k CA LD have a lot of stuff on medium to if you want to check that out. If you're interested in learning about angel investing, you will see any of my videos have a lot of stuff that would be useful for ENTJ managers. You can go to or up and coming software engineers you can go to Nick Caldwell COMM And check out the videos there try and post stuff they'll help people out. So you know, just google me just stuff will show up.

Kimmiko James  48:06  
Thank you for listening to this episode of The Black Enterprise Network podcast. Join me in the next episode when I speak with Gladys kooba See you in the next one.