As Yishan Wong celebrated graduating in computer science from Carnegie Mellon University in 2001, some 200,000 jobs were cut in Silicon Valley.
The dot-com bubble was bursting and a generation of tech workers were being spat out from the up-and-coming industry as collateral damage.
It’s why when Wong got his first engineering role at PayPal, he “just felt lucky to get a job”.
In fact, it was the only decent offer he had.
At the time, he had no idea it would go on to become the big break that would lead to joining Facebook in its early days, taking on the CEO role at Reddit and now founding his own climate venture, Terraformation.
“It turns out, being at PayPal at that time was very important,” he tells Fortune as we dive into his résumé to find the roles, experiences and bosses that have shaped him into the CEO he is today.
Burger King, front of house
1995 - 1996
I mopped the dining room, cleaned the bathroom and took down orders… At the time, Burger King still had a pretty manual old-style 80s register that didn’t calculate the change for you. I became extraordinarily fast at doing calculations. My supervisor was always impressed that at the end of the shift, my drawer never had errors in it.
I learned that wherever you are, just try to do a really good job and you’ll stand out.
The Software Engineering Institute at Carnegie Mellon University, Research
2000-2001
I learned a lot from this job because my boss had around 40 years of experience on me. He got his PhD in computer science before I was even born.
The top piece of advice I've always remembered from him is that anytime you have a range of options, imagine them on a line graph. Never pick the option in the middle, always pick one of the two extremes because then you get extreme benefits.
I used this way of thinking in 2020 when I decided to make my current company 100% remote.
Now that people are going back into offices, our whole company is never going to able to be in one office. But we get the extreme benefit of being able to source talent from anywhere in the world.
PayPal, Senior engineering manager
2001 - 2005
After PayPal had been bought out by eBay it underwent a reorganization. It was then, that I had my ‘worst boss’.
Some people have these hell bosses, right? It wasn't that kind of experience. He was just incompetent and ineffective, and because most of my bosses prior had been so good he stood out.
My advice in that situation is that you can't let it bother you because it'll just eat you up. You’ve just got to do your thing. But it really reinforced how valuable good leadership is.
Facebook, Engineering director
2005 - 2010
I joined Facebook because out of all the companies I interviewed at, it had an atmosphere similar to early PayPal.
I actually asked to be interviewed by Mark Zuckerberg because I wanted to figure out what kind of founder he was going to be. At the time the company had around 20 workers so that was still possible—and very interesting.
Zuckerberg didn't care at all about business or money, and he really didn’t sell out to VCs. All he cared about was that we make a really good product for the users.
He once said to me, there are all these things that you think that you need to be. But leadership is not something that you have to find, it’s inside of you.
It was weird because this guy was younger than me. He still couldn’t drink. But until that point, I did think “I need to like gain these skills, or learn these things, or be older” a lot.
To some point that’s true, yet many of the personal qualities that you need to be a leader come from inside of you.
Sunfire, co-founder
2010 - 2012
When I left Facebook, the startup economy was just starting to bounce back from the 2008 crash.
A friend of mine and I needed a place to like work on our independent projects, but back then co-working spaces didn't exist.
So we created this little invite-only co-working space for our talented friends from Facebook and Google who were also between jobs.
Here's the funny thing. If we hadn't been so Asian about it, we would have been WeWork before there was WeWork.
The landlord wanted us to sign a 10-year lease, but we only wanted a one-year lease because we had raised all the money up-front. Each year as demand increased, so did rent.
We could have kept raising money to match the rent, but it seemed like too much money to ask of our backers for the same service. So we shut the business down.
However, if we had just signed the 10-year lease at $2 a square foot, we could have sublet the office space entirely when rent skyrocketed to $15 a square foot. So Sunfire could have been WeWork, but maybe we dodged a bullet...
Square, Consultant
2011 - 2012
While at Square I gave out a piece of advice to engineering managers which has apparently now been repeated all over Silicon Valley which is ‘hope is not a strategy’.
Strategy is where you say, the following three things can happen, these are the possible outcomes and I have a strategy for all of them, that will get me to where I want to go.
Saying ‘we're gonna do this, and then hope this happens’—as the engineers did that day—is not a strategy.”
Reddit, CEO
2012 - 2014
If you read the history of ‘Reddit under Yishan’ it says that the user base increased fivefold, and that we were able to cut costs and get technical costs down to avoid bankruptcy.
So it sounds like a success. But I felt like it had been a failure. Getting burned out and quitting felt like a setback.
Before I left, I raised a bunch of money for the company, and that fundraising was so depleting that I didn't have as much in me to continue.
I was only around 34 years old and didn't know how much being a CEO involves management of your own energy and psychology.
For a while after, I would second-guess myself, like, "what if I had made this decision differently?" Until I realized: whoa if I made this decision differently, I would still be there—and I don't actually want to still be there.
If that hadn't happened, other things (like founding Terraformation) wouldn't have happened and my successors have done a very good job of running Reddit.
So regrets are genuinely not useful and control is an illusion—make the best of whatever situation you're in.
Terraformation, Founder and CEO
2020 - present
I have found that people who don't like to be told what to do, don't like to tell other people what to do. As it turns out, I'm one of those people and that can cause a problem as a leader because sometimes people need to be told what to do.
I learned that too late to correct a bunch of errors that I'd made while at Reddit. But it's one of the things that I've stayed conscious of in this position.
Workers don't want to be micromanaged, but you have got to be willing to give them some direction.
If you just say the goal is x a very small number of people can take that and then formulate an entire strategy.
Usually, people need to hear the goal is x and the way we're going to achieve it, is by doing a, b, and c.
I still err a little bit too much on the side of not setting those expectations enough. But I try to be conscious of knowing when people need specific guidance and direction.
