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  • Writer's pictureNick Caldwell

From “Hello World” to VP Eng

My Career Journey, Part 1

Hello World! The following is transcribed from an April, 2017 speech I gave about my career journey and leadership principles.

My 2nd day @ Reddit

Hi, I’m Nick Caldwell, and I’m the VP of Engineering at Reddit, this country’s 4th most popular website and 1st most popular source for funny cat pictures. Before working at Reddit, I spent 13 years at Microsoft where I worked my way up from a position as software engineering intern to become partner-level General Manager of a 300 person organization called Power BI.

I’ve been invited here to talk about my leadership journey, my thoughts on diversity and inclusion, and what’s going on at Reddit. You should know that I get really embarrassed talking about myself in public. But, as one of the few African American tech execs out here in Silicon Valley, I hope my story will help inspire you to do better at work or get where you want to go in life.

Now, I’m going to talk for about an hour, and if that’s too long I totally understand. I don’t have slides or anything flashy, I’m just going to talk. If you get bored, my only ask is that instead of playing Mario Run or doing actual work, you pull out your phones and get the latest Reddit app. We just launched an April Fool’s Day project called r/place which will keep you distracted for the remainder of the time.

Where to begin? If I’m going to tell you about my leadership journey then I’ve got to start with what inspired me and what motivated me early on. I was born in Alexandria, Virginia to a white mother who carried me to term out of wedlock, against the objections of her own family, and gave me up for adoption immediately after I was born. This sounds bad but, trust me, everything turns out okay in the end (at least I hope it does).

A few weeks later I was adopted by my mother, a black woman and first generation Jamaican immigrant who had recently finished her college degree in early childhood education and home economics. She was married to a black Vietnam veteran who, after a short career as a Navy JAG officer, later went on to become a public defender, advocate for social justice, educator, and jazz band manager.

These two wondrous people, fully able to have children and living solidly in the lower-middle class, decided to adopt me. And although I grew up with relatively little, and their relationship would strain over the years, they poured everything they had into educating and motivating me. While the act of having and raising children is always about putting someone else’s life before your own, to this day I am in absolute awe of my parent’s decision and see it as a continual, ongoing, every-moment reminder to give back. It is also a reminder of how much in life depends on chance.

But enough of that and back to inspiration. My early life was defined by 3 motivations:

First, even at a young age my father (who if you couldn’t tell from my earlier description was into a lot of random things) was continually exposing me to new topics: jazz, classical, and R&B music, chess, calligraphy, all sorts of book, chemistry sets, etc. One day he brought home from work a Tandy 1000 computer to replace his typewriter. This was one of the very first personal computers if you didn’t know. It had a 086 processor and had been upgraded to a whopping 640 kilobytes of memory running MS-DOS 2.0. Basically a pocket calculator in today’s terms. Yet, I was immediately fascinated by this thing, mostly because of the video games it came with but also because it quickly became how I spent the majority of time with my father. I’d sit on his lap for hours and, even if it meant him just watching me type gibberish into the command line, he didn’t mind.

Later on, at the age of 10, my father got me a copy of my first coding book called “Learn C++ in 12 Easy Steps”. Now, this was an absolute god damned lie. You cannot learn C++ in any configuration of 12 easy steps, 25 years on I still don’t think I fully know C++. And, while frustrating, this book really exploded what was mere curiosity about computers into a full-on passion.

There’s really a simple test for whether or not someone is truly going to fall in love with coding. It is the “Hello World” test. The first time you see those words printed out on screen as a result of a program that you’ve written you will know in your heart whether or not coding is for you. Because either you will be amazed and curious about how it is even possible for those letters to appear, or you will be disappointed that it took so much effort to get so little and such pointless output. I passed the test.

Within about 4 months of reading that book I had stopped going outside to play (kids still did that back then), setup my own BBS system (which was a sort of pre pre-internet version of the internet), and was starting to wrap my head around game programming. I had no idea that I could even get a job as a software engineer, no one told me it was a sensible career path and none of my friends even had computers. I just thought they were cool and wanted to learn what I could make them do.

Second, at this point in my life which was around the late 80’s to early 90’s, my mother was an up and coming Vice Principal in the Maryland / DC public school system. That should tell you everything you need to know about my mom. But in case you need me to unpack it for you: first, the DC public school system at this time was one of the roughest in the country. Second, Vice Principal is an enforcement role. They are the people who keep all the teachers and all the students in line. Third, my mother was extremely good at her job.

She brought drill sergeant discipline home and pushed me hard to excel with a combination of love and continual encouragement. I ended up with what is surely an unhealthy work ethic and extremely goal-oriented mindset. It has manifested in several ways that impact me to this day. For a long while it was common for me to start the work day at 5 AM and end around 11:30 PM. I don’t eat breakfast or lunch — don’t want to waste the hours when I could be working. I absolutely love competition, winning and taking on challenges, which results in me both playing way too many video games and reading articles about business rivals deep into the night. Finally, I make endless lists of things to do and have a continual and morbid feeling of unease and anxiety when I’m not completely busy.

So thanks ma for that!

Now, I’m definitely not complaining because she was giving me what I needed. You see, around this time in my life I started to get a bit more worldly — watching the news instead of cartoons, having more adult conversations. Because of my mom’s job, I also had one of the earliest internet connections and I could start to really understand what was going on in the world and my situation.

And I realized it was not good. And I mean personally, my prospects weren’t good. I was an 11-year-old black male, attending the 2nd to worst junior high school in my county. My parents were lower-middle class with no particularly promising social connections, little savings, and were deep in their own personal struggles at work and home. And society didn’t really seem to care. Depending on how you look at George Bush’s war on drugs, maybe it was even actively hostile to people like me.

It really all hit home for me one day when I was walking home from junior high school. First, I should note that my school had some rough edges. I remember things like the Vice Principal getting beaten up pretty badly by a student, classmates who got caught bringing guns to school, huge fights breaking out in the hallways. I don’t remember being too concerned by any of that. If you grow up with that kind of conflict it doesn’t phase you too much if it isn’t affecting you. Mind your own business.

But one day I’m walking home. Up ahead of me about 30 feet away, there is a group of about 8 kids from my school, and they are talking and joking when all of a sudden one asks the other “Hey so, last time you were at my house $15 turned up missing. You know anything about that $15?” Of course, the kid replies “no, I don’t know anything about that” and one thing led to another. Pretty soon 7 kids were on him, beating him, kicking him in the face, stomping him hard into the pavement. I’m not going to get any more graphic than that, but you can imagine what the outcome of a 7 on 1 fight looks like.

This wasn’t the first time I’d seen violence by any means, but it was right in front of me and it was intense. Later on, I would learn about Maslow’s hierarchy of needs, the five elements of motivation for humans starting with basic needs like physiological and safety, then moving on to the loftier goals of love, self-esteem, and self-actualization. Well, all that is just fancy words for the simple fact that nothing is more clarifying and motivating than hunger or the fear of your own safety.

When I got home it was the first time I really thought about my situation and the future. I thought about the world I saw online and in books and magazines. I thought about my interests, being so eclectic: basically an introvert-bookish-computer-sci-fi-video-game-band-anime nerd, and not fitting in at all. I imagined myself in this neighborhood for the next few years, attending the same high school as the kids in the mob I’d just seen beat someone half to death while laughing about it. And after surviving that, then working at a government job like my parents and the friends of my parents.

That just didn’t feel right. I realized that I did have hopes, things I wanted to learn about and be a part of in life. But every day they were slipping away, through no fault of my own, and I had to do something urgently.

Motivation can be about running toward something and it can also be about running from something. And that day, deep in my gut with all the disciplined energy that had been imbued in me by my hard-working mother, and all of the passion for learning granted to me by my father, I decided that I had to get the fuck out of that neighborhood no matter what it took.

Now, I don’t want to spend much longer talking about my pre-employment years so I promise to wrap this section up quickly. But I get asked a lot “well what happened next, how did you get out?” Long story short is that in the Maryland-DC area they have what are called magnet schools, and if you can pass a test sort of like the SAT, they will let you leave your current school zone and bus to a better one. Whether or not you think that’s a good or bad idea, or fair or unfair, it is what I had and it was a way out.

So, I studied for that test every day for about 3 months straight. I put off all other interests, school, computers, saxophone, friends. I just lived in study mode. In the end, I was placed 11th on the wait list, and very very luckily got in.

From that point on I commuted to high school about an hour every day to the nicer part of town. I should say that I was a bit culture-shocked when I turned out to be one of the few black kids in the high school program. Up until this point in my life I’d attended schools that were 90% black. White people were basically unicorns, now I’d gotten the situation totally flipped. But I’ll be honest, I just kept my head down and ignored this and kept working my ass off.

Through my mother’s former manager, I was very fortunate to discover a volunteer IT internship opening with the county school district. My boss then referred me to an open internship opportunity at NASA he’d heard about. A co-worker and MIT graduate I met in the NASA cafeteria then referred me to MIT’s new college prep program for minorities, called MITES. By the time I got to senior year I’d never taken a summer off, had built a respectable resume, scored well on the SAT (after 3 attempts), and was determined that I wanted to attend MIT. I applied and was accepted into other big-name schools, but I chose MIT specifically because it was known to be terrifyingly difficult. And it had become very much ingrained and proven to me that if I worked extremely hard my situation would just get better and better. So I always picked the most difficult challenges I could find.

MIT, as you all know, is located near Boston, Massachusetts. So I was again shocked to find out that there could be a place on Earth with even fewer black people than my high school program. People often ask me “what was it like” to make the transition. I’m not going to lie, Boston isn’t exactly a friendly place to begin with and being black there was not fun. I think I experienced the majority of racist incidents in my life in Boston: the usual name calling, driving while black, all that stuff. But MIT was so brutally difficult that I largely ignored all that so I could try to keep my head above water academically. There was no race in the trenches as far as I was concerned. Yes, getting called the N word every once in awhile stings but you don’t know true pain until you have to pass partial differential equations at MIT. Nothing has been as difficult for me since going to this school for undergrad. If you can survive partial differential equations at MIT you can survive anything.

So just to wrap all that up and put a bow on it. After graduation, the first thing I did was to buy sports car using a Microsoft offer letter as collateral. Then, I took a break, the first real time off work I’d had in a long time and headed back home for a few months. I hadn’t spent any significant length of time there in years and had lost touch with almost all my friends. So my hope was to go back and catch up with them.

Back home there was a restaurant called Roy Rogers. It’s kind of a cheap and run down fast food hamburger place but I remember it fondly because, at the time, they also sold Philly cheesesteaks. You could get them for about $3.50 which is about all I could afford when I was kid. At any rate, feeling nostalgic I drove my brand new Nissan 350z to the Roy Rogers, parked it out front, walked in, got a cheesesteak, sat down and started digging in. Roy Rogers is terrible but nothing beats the spice of nostalgia.

There was a janitor sweeping the floor when I sat down, his back was turned to me but he was slowly sweeping in my direction. And when he got to me he stopped sweeping, tapped me on the shoulder. As chance would have it, this was my absolute best friend from elementary school. For years, we did everything together: ride bikes, video games, basketball, saxophone. I hadn’t seen him since the 6th grade. He said, “so where have you been?” I told him I’d just graduated from MIT and gotten a job at Microsoft. He stared at me for about 3 seconds, then said, exactly these words in response “so I guess you are going to be rich then?” I said, “I guess. I hope so.” A moment passed. Then he said, “well shit,” turned around, and just kept sweeping away. That was pretty much it. I’ve never seen him again. Somehow he isn’t even on Facebook.

There are friends I try to keep in touch with from time to time. But as I learned: you can’t go home again. The vast majority of my old friends are still living in the same neighborhood, and it’s DC so they tend to have government jobs. They are postal workers, elementary and high school educators, mostly. Some are struggling actresses or models. A few are homeless, some got caught up in drugs or gangs, some are no longer with us. One guy works at Comcast. I feel the worst for him. As far as I know I’m the only person out in Silicon Valley from my neighborhood.

So when people ask me: what inspired you, what motivated you, this is all what runs through my head. It’s a simple middle-class story of hard work making your life better, perhaps made slightly more complex by an understanding that trade-offs and sacrifice are part of any significant achievement, and perhaps made even more complex by an understanding of how much luck plays a role.

Moving on, so that we can get to talking about some actual career and leadership moments: I had a semi-pro career in tech that lasted a few years during college but my first real professional job was at Microsoft. Nowadays people ask me “why on earth would you work at Microsoft?” Well there are two reasons.

The first is Bill Gates. Bill Gates was my hero. Bill Gates is still my hero even after I met him and got to see first-hand what a foul mouth he has (more on that later). I grew up using MS-DOS, Windows, and building my own PC hardware. I grew up during an era when Bill Gates said he wanted to revolutionize the world by putting a PC on every desk, he actually did, and became fantastically wealthy in the process. Computers were my lifeline to a better life and during that time Bill represented everything about how I imagined I’d achieve success. Even now Bill, via the Bill and Melinda Gates foundation, has gone on to attack global problems like malaria and HIV/AIDs and has used his influence to encourage other people of ridiculous wealth like Warren Buffet and Mark Zuckerberg to give back. He is also a huge Redditor.

The second is risk. People, particularly people from the Valley, ask me why I didn’t choose to work at Google or Facebook when I graduated. To answer that you’ve got to understand risk, and if the previous story about my upbringing wasn’t clear, I wanted some certainty that my hard work would lead to a better life. Google and Facebook were pre-IPO startups when I got out of college. Microsoft was a safe bet, and for a black kid coming out of P.G. County, wanting to buy a nice car, get his parents a house, this was a surefire win.

I know Diversity and Inclusiveness in the Valley are really red-hot topics now. One question is how can we attract more people of color. And this is a tough problem, but I’ll simply say that back in 2002 if you’d asked me to join a startup, even a Google or Facebook, I’d tell you you were insane. If you recited the common Silicon Valley mantra “fail fast” I’d tell you were insane. I felt for most of my early career that I didn’t have the luxury of failure, because any slip could land me right back where I started in P.G. County Maryland, maybe sweeping the floors at Roy Rogers. It wasn’t until I had a wide safety net of professional skills, a network, and frankly money, that I began to consider looking at startups. But a little of that fear of falling still exists in me, and I think exists in anyone who has had to climb up a few tough rungs to get where they are. Ironically, I’m now hiring heavily for Reddit and have lost diverse candidates to Facebook for the exact same reason: it’s safer bet.

So anyway, I remember as the plane approached Seattle, looking out the window at the beautiful emerald green trees that surround the city, and thinking: I’m about to get paid.


More to come in part 2. Thanks to my wife, Tia Caldwell, for reviewing and editing. Hope you enjoyed the read!

rock on -nick



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