From PM to YC Founder

My thought process for quitting my job and going all-in on my own startup

Today, I’m making the strange and scary transition from being a product manager to the founder of my own startup.

Me and my co-founder were recently backed by Y Combinator, the legendary accelerator behind companies like Stripe, Airbnb and Coinbase. We’re pumped for this new journey.

Leaving a steady salary at a fast-growing company, especially with uncertain economic conditions, is objectively crazy.

But surprisingly, when I tell people about this transition I keep hearing things like

“I’m a little jealous of you.”

“I wish I could do that.”

“I feel stuck in my job.”

I wanted to unpack my decision and lay it out as objectively as I can. The goal is to give anyone thinking about the founder journey (or a big career transition) my thought process for making the leap.

What did you want to be when you were little?

If you asked me what I wanted to be when I was a teenager, I would’ve told you I wanted to be an entrepreneur.

I fondly remember starting small businesses with friends, be it creating and selling comic books in elementary school or planning large scale events in high-school.

In university, I discovered a bunch of career paths that seemed like they would teach me useful skills. Consultant, UX Designer, Product Manager — each one seemed like great ways to learn what I needed to know to be successful.

Ultimately, I was lucky to join Facebook (now Meta) as a product manager after university. I learned a ton from this experience and am eternally grateful for everyone who I met.

But like in any job, I stepped into a well-crafted career ladder that tells you what you need to do to get to the next level of your career. It gave me a great hill to climb, along with people further up the hill to look up to.

Soon, however, my personal goals and the career ladder started to blur together.

I wasn’t thinking about learning skills to be an entrepreneur, I was goaling on skills that would help me move to the next rung of the product management ladder

Climbing the wrong hill

A classic problem in computer science is hill climbing. Source: Chris Dixon.

Chris Dixon, the legendary venture capitalist, has a great essay called Climbing the Wrong Hill. In it, he highlights a trap that many ambitious people fall into:

There is a natural human tendency to make the next step an upward one. [They end] up falling for a common trap highlighted by behavioral economists: people tend to systematically overvalue near term over long term rewards.  This effect seems to be even stronger in more ambitious people. Their ambition seems to make it hard for them to forgo the nearby upward step.

People early in their career should learn from computer science: meander some in your walk (especially early on), randomly drop yourself into new parts of the terrain, and when you find the highest hill, don’t waste any more time on the current hill no matter how much better the next step up might appear.

In other words, the pressure to keep moving up may lead you to a spot you didn’t intentionally choose.

I took this advice to heart and introduced significant randomness into my life by joining a startup after 2.5 years at Facebook.

It was great — I got to work more closely with business development functions, got to talk to customers directly and started to attend industry conferences to learn about bigger trends in fintech, crypto and financial crime. 

But at the end of the day, I was still on the same product management hill, I had a set list of tasks and skills to develop with levels that soon started to find their way into my personal goals.

That’s when it hit me - to become the entrepreneur I dreamt of being since childhood, I might need to take a step down to get on the right track.

What do you need to make the jump?

Some people are brave enough to make the jump with nothing figured out. Alas, I am not.

I decided that I would have two criteria for when it was the right time to take the plunge:

1. Deep understanding of a big problem

2. Great people to work with

For (1), I spent the last four years deep in fintech. From launching WhatsApp Payments in Brazil to helping Paxos reach 10M crypto wallets globally, I had gotten very familiar with the challenges that come with scaling fintech platforms.

P.S. If you’re working in fintech and want to see what we’re working on, get in touch here 👀

For (2), I was lucky to reconnect with an extremely talented, technical friends who was also ready to quit his job and dive into the unknown with me.

Having these two things crystallized gave me the confidence that I could be successful.

So what’s next?

I’m going to share unique insights, non-obvious lessons and war stories from the earliest days of company building through this newsletter.

If this sounds like your cup of tea, be sure to subscribe or share this with friends:

I’m also headed to San Francisco for the summer! If you’re in the area and want to catch up, reach out.

Finally, I’ll be sharing more details on what I’m working on soon. So stay posted.

Thanks for reading,

- Will