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Hello world. A few reflections on my first year at Stripe and a bit on my first ten years building stuff.
I’ve joked that joining Stripe is my first rational career choice. 4 quick stories.
After school, I declined my MSFT internship return offer (but I could work on Excel!) to jobless-ly follow my girlfriend, now wife-y, to Washington, DC. I joined a non-war tech company (comScore), learned data at scale, hired my friends, and discovered how the internet works.
Three years later, I got declined an offer for my dream job at Google (after many attempts to get that fancy PM gig) to join @jordancooper at @hyperpublic in NYC. It’s still a bit crazy I did this, there was zero sound reasoning or expected value calculation to make that call.
The best I can muster is that the @hyperpublic team was hardworking and down to earth, more focused than the product called for. Long story short, Groupon later bought the company after an early business development deal. We moved to SF. New life.
My dad: “If you were at Google, you’d still be trying to figure out where the ball pit is”.
At Groupon, we had a blast even though we joined at the absolute peak of the stock value (dropping 25% ~every quarter will toughen you up). Love @andrewmasom. I learned was that early career individuals are oddly capable of stepping up to own large, vague problems under distress.
Left after 3 years to found @wagonhq with @mkscrg and @deland (met at @hyperpublic). Wagon was good product, great team, but not a business (100% my fault). It'd have been a fun, profitable indie project or maybe a long shot enterprise tool. Uncanny valley. Learned CEO stuff.
We hustled to sell the company to Box and scaled their data eng stack and launched new analytics and ML products. Box showed the importance of API reliability, sales efficiency, and positioning. @aaronlevie is a top human should be credited for The Cloud, and his A++ tweets.
Later, rather than start a new company, I wanted to consider finding a place where I could be my full founder-y self (ship products, lead teams, hurl my positive intensity at problems) but forgo the existential day-to-day of early company building. I hadn't interviewed in years.
I wanted an “actionable disaster”. After you’ve led startups and worked at large companies, you know every company is a ~disaster. The question is, (1) is their disaster actionable and (2) do you want to action it? (I have no interest in helping fix FB, even if it is actionable).
A small group I admire drafted independent, ordered lists of companies that might fit the bill. I remember writing places like NYTimes (I’d love to action it), “space stuff” (throwing heavy objects high in the air must be disaster), and the recent fast growing B2B businesses.
Stripe was on each of our lists. We’d been customers, looked up to some of the internet famous people that worked there, mimicked their API design and technical voice, and ogled their CSS. It just looked too pristine from the outside, it must be a disaster under the hood.
I’ve really never experienced a super fast growing company before. I recommend it. It’s hard for me to tease apart which of the following are unique to Stripe, unique to any company with product market fit, or just dumb luck. Regardless, I’m into it.
A year in, here are the top 10 things I appreciate about Stripe and I’d suggest mimicking.
1. Users first. One of the few sins you can commit at Stripe is not talking to users. Thankfully it’s nearly a panacea for all tricky situations. I mean you need to be texting with them. What's the founder's pet's name? Get all up in their lives style user first.
2. Ask only the highest information splitting questions, the ones that explores the space of answers and test the bounds of a proposed answer. I've seen the founders propose questions then say, "I'm okay with any outcome that answers my questions in an internal consistent way".
3. Clap for the right things. At a company all hands (every two weeks, a whole song n' dance), one time we crossed over the largest revenue number I’d seen in real life (a buncho zeros). Next up was a tech talk of our frontend component library. Which one got the rousing cheers?
4. An oddly small number people. We’re nearly 2000 people but there are still a shockingly small number of people working on critical or creative domains. Many of us bear the brunt of that slimness but I am convinced it’s why we make good stuff both for users and internally.
5. Implausibly good. There are some things that are so well done internally you couldn’t sensibly imagine a “boss” assigning an “employee” to do it. Someone just on their own decided to make it great (I’m including the soup). People operate at ceiling of they can possibly handle.
6. Kumbaya Capitalism. A phrase I say to explain @mcgd’s General Management course (take it, a no brainer) applies to Stripe. I was an intern at [Big Bank] and I confused my dislike of their culture with a perceived dislike of finance. Finance is great, West Coast Wall Street++.
7. Positive outcomes due to variance != information. We don’t just ask what’s the free cash flow (or margin) but we ask how its correlated with cohort input measures. If a project is improving, it’s not an automatic yay, what's the systematic, repeatable, transferable reason why?
9. An instance of a problem is a problem. There is appreciation for eradicating an issue to 0% customer pain or internal productivity troubles, rather than just mitigating it. It often doesn’t take more work, but does require being relentless against reversion to mediocrity.
10. To the metal. Stripe rewards people who deeply understand multiple domains: technical, strategic, customer, design, etc… It’s a pretty crazy high bar at our scale for our leads to know all the things but a surprising number of them at least seem to.
These 10 things make for easy reading article but practicing these individually minority impactful, consistently high energy behaviors every day is really hard. I don’t think it’s possible without like minded people constantly reminding ourselves to keep going like this.
I’ll skip what’d I’d like to improve about Stripe for a later time, but here are 5 things about me I am focused on improving.
1. Solve problem 1 and 2, let next 98 burn: There is simply too much to fix. The best feedback I got from @collision was, “you need to be stuck more”. Be stuck on your top top problems, don't just be productive on your next 98.
2. Become a domain expert. I am learning a ton about payments globally and locally but we have top 100 financial system minds in the building (or remote) and I for sure not yet one of them. Holding on to this naivety has been helpful for simplicity, so can’t let that slip away.
3. Not wearing my intensity on my sleeve. I’m a pretty driven, low tolerance for mediocrity person but it can be overwhelming and sometimes counter productive.
4. Meet more customers. I meet a few customers a month but not in depth, I’d like to become texting friends with our most disgruntled customers (and non-customers), especially folks scaling a business outside of the US. Please hit me up.
5. Work less (maybe?). I am happily consumed by Stripe. My wife and I are in a work-focused part of our lives (she’s an asylum lawyer for women fleeing from South America… she’s busy) but at some point will need a balance (maybe?). I work more intensely than I did as a founder.
It’s been a great year, it feels good to share it with you. It feels like I took a wild left hand turn and entered a new civilization. I’ve joked that Stripe will be my last job and I’m in for 30 years, so far so good.
I am so thankful to @amber for white boarding how payments works, @patrickc, @collision, @gaybrick, and @dps for trusting me in a role I was/am woefully under-qualified for, and to our entire Payments Infrastructure team (150 people, +100 in a year!) for pushing me to be better.
Lastly, I am always on the hunt for the best possible person for any role at Stripe, including my own (I love it but the likelihood I’m the bestest person in the world is low). Hit me at jweinstein@gmail.com to learn more about anything at stripe.com/jobs.
The website is glamorous, the work is strictly not. Gogogo!
@andrewmason* :)
@AaronLevie --> @levie :)
