A couple months late, but it’s been a busy year.
Back in June I joined Stripe, which at the time of writing is the highest valuation startup in the US. Conveniently, it’s located just walking distance from the San Francisco Caltrain station, and I find myself preferring the Caltrain commute by far over the driving or motorcycling commute.
Much like Elon with Tesla, I, too, had a master plan for my career. I wanted to get a job at a prestigious, talented tech company so I could hone my tech skills. Unlike many of my peers, I started engineering relatively late in college after a sudden career change from law, when I quit the debate team and decided to pursue CS full-time. This happened to be Twitter, for which I will always be incredibly grateful. I learned so much and felt that I had bridged the gap between myself and many of my peers, at least from a technical standpoint.
The next step was joining a startup, where I could learn both whether I liked startups and whether I could operate in such an environment. Accordingly, I joined Skip Scooters. Almost immediatley, I found myself validating the idea of a startup environment. I generally liked working in startups where things moved fast, I knew almost all my coworkers by name, and I could have an outsized impact. And more importantly, I could see myself founding a startup, too. The hours were a ton, especially early on, but I loved it. Fortunately, Ahana and I were still long-distance at the time, so she didn’t care if I spent weekends working or at the office, or if I Skyped her from work and then returned.
But as time went on, it was clear that I had to change once more.
First, my hours had to dramatically decline as we started on a new journey - married life - together. We got a dog, and I wanted to spend the first year cementing my new relationship and making sure everything was fine at home.
Second, we wanted to buy a house, and inflate our lifestyle more generally a bit (we are both incredibly cheap and unwilling to spend on most things), which meant I needed to work at a place that could pay me more than startup compensation - especially with kids potentially on the way in two to three years.
Third, I wanted a place that was generally encouraging or alright with employees having side gigs. I had several ideas for side projects and apps, but perhaps none fit the ideal of a venture-backed company. In any case, I wanted a place I could park while I tried out many of my ideas, even if it meant without cofounders and just by myself in my spare time, and Stripe was more than in favor of that. By my very unscientific polling of my colleagues, almost fifteen percent are actively working on side businesses, and most are using Stripe! In turn, Stripe loves this sort of feedback, since any flaws in the API are addressed almost immediately. This was exactly the kind of place where I could try out various ideas, and if one didn’t work, there wasn’t really any risk.
Lastly, working at Skip has taught me the importance of a fundamentally sound culture. Culture is so incredibly difficult to nail and so disastrous for the company if done incorrectly that I decided I needed to be at a place that, at least from the outside, did it right. Almost every single Stripe employee I’ve ever met has a unique ‘stripey-ness’ to them, so I knew Stripe was one such a company. To be clear, I’m not suggesting that Stripe’s culture is “good” in the abstract or even that other companies should adopt it. Rather, I’m merely saying that Stripe has been incredibly thoughtful about the kinds of people it tends to hire, and that an engineer at Stripe almost always has a quality to them that’s recognizably being from Stripe - a sticky attribute that’s somehow only grown as the organization has doubled or even tripled. That, more than anything, indicates the presence of an incredibly strong and resilient culture.
With those criteria being met, I actually didn’t even interview at more than one company. I knew almost immediately Stripe was where I wanted to go, and the team didn’t even really matter in the broader scheme of things. Incidentally, my team ended up being amazing, but that was accidental.
It was clear to me from the outset how much thought Stripe puts into everything. That’s not to say they’ve done it perfectly or even good, but it’s clear that they’ve thought through it and at least tried to be significantly better than their competitors. For me it started with the interview process. The standard whiteboarding, algorithmic questions do an incredibly poor job of assessing my day to day functions - and almost every single engineer I’ve ever spoken to agrees with this sentiment. Yet, Stripe is the first company I’ve ever seen that has done a meaningful job at addressing this. They focus on the core competencies of an engineer: design, finding and fixing bugs, and implementing features. And they focus on just that, all the while attempting to replicate an engineer’s working environment as closely as possible. IDE’s, Stack Overflow, everything is allowed!
This sort of attention to detail and thoughtfulness is present in all decisions Stripe takes. Recently, Stripe announced that remote was the next pillar of engineering. Stripe has long had a principle of open-ness and transparency when it comes to almost everything - so much so that, even today, almost every single email list is public to the entire company.