My Tech Career Origin Story
How a BBS gave me super powers that kick started my career
Last week I had the pleasure of sitting down with Ivana McConnell for an interview. Her series, Origins, features interviews showcasing the origin stories of the underrepresented in tech — the ‘eureka’ moments that made them fall in love with the industry and the journeys that followed, in all their offbeat glory!
First thing’s first: tell us a bit about who you are, and what you do now.
Sure! I’m Nick Caldwell, and I’ve been VP of Engineering at Reddit for the past 9 months. Before that I had a 13 year career at Microsoft where I worked my way up from intern to General Manager of a product group called Power BI. I live in San Francisco with my wife Tia and dog Poochie (a corgi, because Cowboy Bebop). I grew up in Largo, Maryland which is a little suburb to the south east of D.C. as an only child.
Besides building the team at Reddit, lately I’ve been doing a lot of writing about management, participating in /dev/color, and am starting up a scholarship fund called Color Code.
What’s does your day-to-day at Reddit look like? What’s your favourite part about it?
Management is all about making sure that your team has everything they need — inspiration, tools, processes — to head in the right direction together. Over the last year, Reddit has undergone a lot of change and there’s more to come. A big part of my job is organizing the engineering team and making sure that we are delivering new features to users on time with high quality. So on a typical day you’ll see me tracking engineering work in JIRA, coordinating upcoming features with the PM team, working with our network of vendors/contractors, and coaching my staff.
A sort of mission statement we like to say around the office is that “everyone has a home on Reddit” and I look forward to making that a reality.
There’s no one favorite thing about my job, so I’ll give you three. First, it’s pretty amazing that I get to come into work every day and make Reddit better. I have been a Redditor for just shy of a decade and it’s always been one of my favorite sites to learn, laugh, kill time, and more. There is nothing better than getting to work on a product you love alongside a great team, which is the second thing I like about my job! Reddit’s engineering organization is packed deep with some of the smartest yet low-ego engineering minds I’ve encountered. We’ve also got a “People and Culture” team that does a great job of making Reddit a fun place to work. Probably my favorite example of this is the all-company trip to Lake Tahoe. The final thing I love is Reddit’s potential. We have 300M monthly active users but there’s a lot we’re doing this year that should drive the number even higher. A sort of mission statement we like to say around the office is that “everyone has a home on Reddit” and I look forward to making that a reality.
When you were a kid, your dad brought home a Tandy 1000 — is this where your love for coding began?
I was only about 4 years old then, so I don’t remember much about it other than that I learned enough to play my favorite games: Reader Rabbit, Pac Man, Tank!, and a few others. When I watch my nieces play with their iPads and iPhone nowadays, I suspect they are far more tech savvy than I was at that age.
At that time no one in my life knew about computer programming. But gamers and coders have a lot in common. They share the same systematic ways of thinking about problems, the desire to optimize systems, and the superpowered ability to stare at screens for hours at a time. So inevitably, my love of games eventually transformed into coding.
What was your ‘eureka’ moment — the one that, if you look back on it now, sparked your journey? How did it feel? Was it “Hello World”?
In junior high school, I had a friend named Billy, and we were great friends back then because we both loved video games and were both absolute nerds. One day he invited me over for video games at his house. I was expecting Super Nintendo but what I got instead was an absolutely epic re-introduction to PCs.
Billy had LHX Attack Chopper, Wing Commander, and Wolfenstein 3D. These were all amazing, groundbreaking PC games at the time. After that, Billy launched a game he had written himself in QBasic… Then he used a 2400 baud modem to dial into a local Bulletin Board System called “The Illusionary Forest” and download a copy of Commander Keen.
I was completely blown away by all this. I biked home after that and begged my father to buy a new PC, which we did a few weeks later on a trip to Micro Center.
Out of all that experience, it was the BBS that stuck. BBSs were a doorway to a much bigger world, where I could be anyone I wanted to, talk to whoever I wanted to, learn more than I could at school. I eventually learned to code so that I could write and sell my own BBS software.
Of course, the first program I wrote was “Hello World” in C++, but I think the real catalyst for my coding career was watching my friend hacking on QBasic and imagining what I could do when it was my turn.
BBSs were a doorway to a much bigger world, where I could be anyone I wanted to, talk to whoever I wanted to, learn more than I could at school.
A bit later, I was also introduced to the idea of starting something of my own, the Silicon Valley dream; I was in a summer program call MITES (Minority Introduction to Science and Technology) hosted at MIT. It prepared me for the school and introduced me to entrepreneurship.
You went from that Maryland/DC magnet school to MIT, then to Microsoft. What brought you to Reddit eventually?
Before Microsoft, I got my first paid internship as an engineer at NASA working on software for x-ray detectors. In school, I became fascinated by AI and machine learning and game programming, and that resulted in my first internship at Microsoft on the Direct3D team.
My first fulltime job, though, was at Microsoft — first working on natural language processing components, which led to learning about enterprise search, information retrieval, machine translation, and machine learning. After that, I jumped into business intelligence where I picked up knowledge about data modelling, data visualization, in memory databases, and advanced analytics. Somewhere in the middle of all that I got my MBA from UC Berkeley, became a General Manager, and started learning about the inner workings of marketing, finance, and business development. Because of MITES, I was continually coming up with ideas with that startup mindset; I always wanted to do something, but it was safer and still fun to stay inside Microsoft and do “intra-preneurial” projects. Now I’m at Reddit and it’s great fun to pick up knowledge about consumer products, online ads, and venture capital.
Going to Reddit was a shock to a lot of people in my life. I had been at Microsoft 13 years and was having one of the fastest career trajectories possible. I’d also built a truly amazing team. I think if I were still there I’d probably be working with my mentor James on how to become a corporate vice president at a large company. But a combination of things finally got me to leave:
First was a mental shift around how “safe” I felt. I realized that a lot of my energy and motivation came from proving myself through work and that my validation came in the form of promotions and money. But at a certain point, money just stopped being a huge motivator for me and by the time I became a General Manager there was nothing left for me to prove career wise, other than to manage more and more people.
I realized that a lot of my energy and motivation came from proving myself through work and that my validation came in the form of promotions and money.
I like learning new stuff and challenging myself but there wasn’t anything on the horizon that excited me. So, in the months before left Microsoft I was faced with a choice: continue on the same track and be paid a lot to work on a huge new project I didn’t honestly love, or finally chase the dream of Silicon Valley I’d been putting aside for a decade.
Second, Seattle weather. ‘Nuff said.
Third, living in Seattle made it very hard to see our family. Our brother and sister and live in California but we rarely got to see them, and they were starting to have kids of their own. It made us stop and realize just how isolated we were.
Somewhere in the middle of all this, Reddit contact me about a VP of Engineering opportunity. The timing was good because my manager at Microsoft was asking me to move into a larger role outside of the Power BI organization. I was already thinking about “what’s next?” and open to taking on something new. I suddenly found myself with an opportunity to make a clean break from Microsoft and get down to the Bay Area. So I handed the reins of my organization over to a guy I knew would take great care of it, and my manager found another experienced exec to run his new team.
I had been looking at other jobs in the Bay Area, but Reddit was the first consumer company. What they needed perfectly matched my skillset: building product teams fast. I’m no longer the best coder around, but if you drop me out of a plane handcuffed and blindfolded into the deepest darkest Amazon, I will crawl out of the jungle 3 weeks later with a kick-ass product team and a working MVP.
The other thing that “de-risked” the decision for me was a conversation with Steve the CEO where he explained just how much traffic Reddit gets on a monthly basis, the general direction he wanted to head with the business model, and how critical communities are to Reddit. Having launched a few products before, it immediately clicked that his vision would work as long as we could move quickly and carefully.
You’ve mentioned before that “you can’t go home again” after life changes so much. How do your parents perceive your career now, after laying such strong foundations for it?
They are astoundingly proud but I’m sure they have no idea what I do. I know they aren’t on Reddit or Power BI users. Whenever I go home my family asks me to help them install Office or debug their machines. But I think that’s true for a lot of people who work as software engineers.
The other thing it took me a long time to realize, being so focused on my own career, is that my parents never really cared how high I got in the corporate world. When I was at Microsoft, they didn’t understand what a General Manager was, or show any interest in the fact that had come to have a large team with employees around the world.
My mom was a school teacher and my father a public defender. I have yet to meet two people who are more selfless and satisfied with what they have. They only ever really cared that I was doing my best for the people around me.
Do you ever feel pressure to be a mentor, an example, or a role model for underrepresented folks in tech?
I feel a lot of pressure to be a good person. I’ve had a very fortunate career with an unbroken string of supportive managers and great opportunities. The great thing about being where I’m at career-wise is that I can do pretty much whatever I want now. I don’t need to prove anything to anyone or chase money.
So when I try to mentor, give back, or write a blog, it’s because I actually think it is important to help other people. Tech careers are today’s gold rush, and I want to make sure that women and minorities have access to the opportunity.
If you could do everything all over again, do you think your journey would be the same? Would you want it to be?
Looking back on my early career I thought of Microsoft was a “safe” job where I could build a career and fortune over time. I equated money with a safety net that would allow me to take on more risks. But now I realize that I always had something even more valuable: time and motivation. When you are early in your career, time itself is a safety net. You can take on risks, try a lot of things, and if it doesn’t work out you can try again. Because I didn’t have this mentality, I passed on great opportunities that would have made the entrepreneur in me happy.
Second, I am a total workaholic. I put all my energy into building software with little to spare for thinking about kids or family. But eventually I came to understand that tech projects are sandcastles. Even the most beautiful and carefully designed system is meant to be swept away and replaced someday. Looking back, I would have learned to balance work and life more carefully.
Nowadays I work at Reddit where the company culture makes it hard to fall into that trap, and my wife also gives me a back-of-the-hand slap if I’m spending too much time on the keyboard.
You said, “Roy Rogers is terrible but nothing beats the spice of nostalgia.” Is there anything about the internet or technology that you remember from your early years that gives you the same nostalgic feeling?
I hate to age myself this badly but Usenet, IRC, BBS systems, MUDs. You could be pseudo-anonymous and because of that you could connect with people in ways that weren’t possible in real life. But something got lost along the way from the development of those early systems to modern social networks. It could be the nostalgia speaking but the connections with total strangers I met on BBSs, and even AOL, felt more real to me than most of my Facebook and Twitter “friends.” The early internet was maybe slower paced and harder to get into, but the result was a deeper sense of community.
Reddit works because of great communities. I think it has the potential to bring back that spirit of the early internet and make it available to everyone on the planet.
How many steps did it take you to become an C++ expert in the end?¹
I will proudly say that I have written software in C++ that is today used by a good fraction of humanity. But I will never say I’m an expert in C++.
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