How I got hired & fired from Stripe as employee number 20-something in 2012
Buckle up:
I have told this story to hundreds of people in person. After a decade since it happened, I wanted to reflect on how much this experience changed me & my trajectory.
Most importantly, I wanted to publicly thank @patrickc & @collision for giving me the opportunity.
So, between 2008–2010 I ran a small clothing store online. We made it easy for people to buy hoodies. It was called Hoodeasy—clever, I know—and we sold hundreds of thousands of items to students in the UK.
I built most of the site myself using @Wufoo, Dreamweaver & hacky code.
I kept running into the same issue: processing payments.
I tried everything: PayPal, Google Payments, local bank solutions, and began exploring a fully customised solution that would allow me to accept credit cards directly on my domain.
It was excruciatingly expensive.
Hoodeasy was sold for a small sum to a competitor when I realised that I wanted to make software more than I wanted to be in the garment business.
I spent my time learning about programming, attending University of California Santa Barbara’s accounting course, and kitesurfing.
In 2011, I began focusing on kitesurfing really seriously. When I stopped back in my home town, my best friend went for a walk with me and said one thing:
Is this it? You are just going to be a surf bum? I felt you had so much *potential*.
It really pissed me off. He was right.
The next day I started thinking: if I could work anywhere, where would I work?
There was only one answer: Stripe
I had been an entrepreneur on the Internet. They were solving my number one problem: Payments.
I deeply understood how instant signup & no up-front fees would help.
I applied on their website for a growth role. It required someone to understand enough coding to talk to engineers and enough business to talk to founders.
I felt I would be a great fit.
The interview process kicked off a week later & I got the chance to chat with their team.
Each phone screen got more and more fun. I researched *everything* I could about the people who were trying to grill me.
- I spotted spelling mistakes in Stripe’s documentation.
- I found bugs in their Ruby library.
- I went deep into their personal blogs.
I went deep on Stripe
After a few phone screens and a chat with their visa lawyer, Stripe flew me out to meet the team in San Francisco.
I stayed on a friend’s couch and woke up to a bluebird day with the sun beaming—I was ready.
I showed up to the office ~30 minutes before I needed to.
I walked in
My first impression of the Minna Street office was the light airiness of the space and the “clackety-clack” of Kinesis’ ergonomic keyboards.
People here were really focused.
@darraghbuckley got up from his seat & welcomed me into the space.
Then the interviews started.
I cannot recall everything perfectly here but I have some great memories:
@collision and I discussing all the issues with every other payments product I had used.
@sch asking me about when I had gone above-and-beyond for a customer in the past.
@patrickc’s laser-focused eyes.
After a couple of days, they sent me an offer and I got to meet more of the team.
I pushed as hard as possible for as much equity & as little salary as I could get to survive in San Francisco. They were incredibly generous on all fronts.
Then began the process of moving my life
I left my business, my family, my country & my girlfriend for Stripe.
It was not easy. Changing everything you know for a team you don’t is not simple. The administrative and emotional burden is something I have only come to understand more as my life as an immigrant matures.
At the time, I wasn't worried about any of that. I just wanted to get back in that office.
I wanted to be around those people.
I wanted to work at Stripe.
I wanted to help.
My first week was a whirlwind. I helped them onboard a public company as a customer, met @RonConway, and got to know all the incredible people helping make the software a reality.
My first month was magical, I saw them launch Stripe Canada and deal with crazy new risk issues.
I had never had a real job before. I did not know what to do so I just tried to do everything.
That is where things started to wrong: I did way too much.
I started making it a habit to show up to the office before anyone and try my best to stay awake longer than anyone.
At the time, I did not even know what bipolar was. Now I have been diagnosed, I can clearly see that I entered a state of hypomania: incredible energy but totally uncontrollable.
I was in the office doing things, but I was not working as part of the team.
I flew to New York.
I wanted to help Stripe build a presence there.
Did the team want that? I still don’t know.
The worst thing for someone with bipolar is to change their timezones and forget to sleep. I was doing that multiple times a week.
It was turning my brain into a fusion reactor.
After my second month, I could feel that things were not right. I was not clicking with my team. I kept making simple mistakes.
I wanted to prove to them that I could be helpful. So I switched gears:
- Focus on mobile payments
- Hire my good friend, @lachygroom
Stripe’s mobile bindings were very primitive at the time, and I learned from lots of companies that they didn’t have faith in their systems yet.
I shared this at a Stripe all hands and it really hit the team.
They started to beef up their Objective-C and Java libraries.
I had known Lachy for years online. He was one of the sharpest minds I had discovered on the internet.
I relentlessly pitched Lachy internally. The team were not convinced because he was so reserved in person.
I made the argument—night and day—to look past that.
They gave Lachy a work trial and I was over the moon.
But I was totally exhausted. I kept missing nights of sleep after moving onto a inflatable bed to save the company money on a hotel.
This was such a simple mistake: working hard is amazing, never sleeping is just stupid.
When it came time for my 3-month review, I knew things were not vibing.
John took me for a walk outside the office, and told me they had to let me go.
I tried to reason with him but he was firm.
They were right to fire me.
I remember him saying something about my energy.
Initially, I was incredibly angry. A year later, I was just incredibly grateful.
Stripe sets the bar for all startups.
They left an imprint seared into my brain of what true greatness looks like.
They showed me what was possible when people work hard together in person.
The Collisons are the most formidable founders I have ever come across. I am so grateful to them and the early Stripes who took my under their wing.
The way they cared for me after I left the company speaks volumes about them as people.
I am very proud of them all.
A lot of people ask me:
How do you feel about missing out on the stock options?
Initially, it stung. Now, I know that I value the experience I had inside that company more than almost anything in my life.
It showed me the magical potential of teams that relentlessly care.
I got to see @ludwig, @bdc, @michaelvillar & @maccaw create software.
The vibes those folks had as they crafted the interfaces was just sensational.
I got to see @gdb, @nelhage & the infrastructure team scale up Stripe’s systems.
I got to eat @tonydebok's amazing food.
I am forever grateful to the team and for the time they invested in me.
I know I was not up to their standards because I did not have a good handle on how to manage my mind and I had never worked as part of a team.
I have worked hard on those things.
I will always love Stripe.
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