Why I left a billion-dollar startup

Reflecting on tough career choices, money vs. freedom

Previously, I shared my wild adventure being chased by Instagram. I ended by walking away from a hard-fought $375K offer. This post covers why I pulled the plug, and one more career update: I also left my startup job, leaving behind a few million in unvested stock options.

First, what happened with Instagram?

I was impressed by their salesmanship. Despite not being drawn to big companies, I was intrigued by the opportunity to build Reels: a new bet at a company with strong consumer product chops. I came very close to signing. 

The protracted negotiation process threw a wrench in that plan. It was a reminder of the rules that govern big companies. I’m a no-BS person. The negotiation gave me pause, and made me question my long-term goals. 

We often make career choices by looking at what’s right in front of us. We prepare for the next move, not the five moves beyond that.
This is ok early on when we have less conviction over who we are, what we’re good at, and what we like. But each move should bring us more clarity, helping us head in a direction aligned with where we want to be long-term.

So, where did I want to take my career?

When I first became a PM, I fell in love with creating solutions that grew the business and made customers happy. It was my dream job. Every day was different, each experiment worked differently. It was, quite honestly, the best dopamine. 

The next opportunity became hiring and managing PMs. It was a new challenge. I was building society-approved career momentum. More dopamine. 

As the novelty wore off, I came to the surprising realization that I wasn’t interested in the next level up. Being a Director/VP is gratifying in theory, but not so much up close. I lost interest in the game.

I care most deeply about freedom. Freedom to say what I think, do what is right, and spend time the way I see fit. 

As I took a hard look at myself, it became clear that Instagram was a shiny opportunity, but it would always be just a detour. I would probably be in awe to start, but inevitably chafe against the reality of operating inside a big company. 

With that in mind, the decision to walk away from the offer was bittersweet, but truthfully not that difficult to make. It was also a type 2 decision: if I change my mind, I could (probably) find my way back in.

Jumping out of a rocket ship

All of this left me at an unexpected crossroads with my existing company, Faire. I could continue on as if nothing had changed, or I could choose to not hide from the answer that awaited me. 

This was a much harder process. First, the IKEA effect — I’ve spent nearly 3 years pouring my life into learning and building products at Faire. I’ve made great friends along the way. Second, FOMO — what was once a tiny startup has grown into a multibillion-dollar rocket ship. I had a few million in unvested stock options. 

If you’re on a rocket ship, why would you jump out mid-flight?
Yet somewhere along the way, our paths had already quietly diverged. 

The company has grown 20X in size since I joined. Whenever that happens, you end up doing multiple tours of duty. You take on different missions based on the company’s needs. And you hope dearly that you scale with the company, which is corporate speak for growing the scope of your contributions proportionally. You do so by delegating, hiring, managing, and constantly reframing your charter. 

There’s rarely a day of comfort. It feels like you’re failing if you don’t scale at the same pace. That collective myth is the fuel that powers high-growth startups. 

For the most part, I was scaling. But the journey that was once an exciting adventure turned into an exhausting slog in my final months. A new revelation began to dawn on me: I wanted to build freely, and on my own terms. Even if it meant making less money, and taking on more personal risk. Working at a startup is hard enough without feeling like your heart's not in it. 

I’ve always been more of a sipper of the kool-aid than a drinker. When you sip, it’s easier to taste the flavor and judge if you like it or not. 

Even so, if COVID never happened, I doubt I would have the courage to leave. Going remote has given me the alone time I needed to examine my motivations more closely. When we’re constantly surrounded by others, we fall under a collective spell. We move comfortably with the crowd without questioning whether it’s what we desire. 

This is why it’s important to surround yourself with the right (small) crowd. Nobody is immune to the influence of others.

Let’s talk money

This leap of faith would not be possible without having had multiple opportunities to develop skills and build enough savings. Once you have skills and savings, you can fund all sorts of experiments. And savings, I’ve learned, has more to do with living below your means than maximizing your earnings. 

Still, leaving a rocket ship means walking away from a lot of money (at least on paper). The good news is that I’ve vested the majority, so if it ends up being a big win, I will land among the stars. 

The bad news is that it costs a boatload of cash (for me, $300K) to keep the equity if you choose to leave. Here’s life-changing advice for anyone considering joining a startup: negotiate for a 10-year exercise window on your stock options as part of your signing offer because the default is 30-90 days upon leaving. 

Many people are simply not able to afford to pay for the very stock options they earned by taking a big job risk (and often a salary cut). So they forfeit the upside, or stay shackled to the company in hopes of a liquidation event. The system is appalling, and designed to punish those with limited resources. Consider yourself in the know :) 

A steady paycheck is also hard to turn down. I find there are two groups of people who are acutely affected: those who have no savings, and those who have grown their paycheck. When you have no savings, it’s simply unthinkable. When you’re good at trading your time for money, however, it’s hard to imagine replacing it with something else. The hedonic treadmill is never-ending. 

I narrowly escaped this trap by reminding myself that it’s always worth trading money I have today for something I would regret at the end of my life. Sure, I could postpone leaving for another year, but it would not be any easier. Risks only get harder to take later in life. It’s an exorbitant privilege being able to chase upside rather than guard against downside.

My third act

I used to think a career meant working at a company. Then I learned you can start a company. Now I believe a career is simply about making something people want, and capturing some of that value. 

Why trade time for money when you can trade value for money?
The internet has massively expanded the spectrum of possible careers — a generational shift that remains highly under-appreciated. 

In the cold light of day though, I’m still terrified to embark on this third act. Act 1 was learning to analyze businesses as a consultant. Act 2 was learning to operate a business as a PM. Act 3, I hope, is learning to bootstrap a business. 

I’ve never identified as an entrepreneur. Is building a business a learnable skill? Stay tuned. 

As for this newsletter, well, it’s been the silver lining of my 2020. It has given me immense meaning, and brought wonderful people into my life. So I’m doubling down. Here’s what you can expect:

  • I will speak even more openly now. Get ready! 🌶️
  • I will be sharing my ideas, process, and just plain building in public — same product lessons, higher stakes
  • I will be learning new skills to retool myself as a full-stack creator
  • I will continue building an audience because there’s nothing more fun. Which means I would love your feedback!

The first idea I’m playing with is around productizing my experience, inspired by Jack Butcher. Setting metrics, building products, and storytelling are valuable skills. It’s taken me years to learn, and they tend to be gated behind the walls of select places. I plan to teach everything I know. 

In my final days working a corporate job, I was reminded of this Naval quote: “The reason to win the game is so that you can be free of it.” 

I tell myself I’ve won the game in record time. And rather than playing another round, I’m ready to create a new one. New rules written by yours truly. 

Maybe one day I will miss the game. But not today.

👋 P.S. If you want to join a top startup, check out who's newly funded and hiring or benchmark your startup salary & equity

Read this next:

One last thing: I made an actionable toolkit to grow your product career! Get the shortcuts that took me years of work to figure out.

Product Manager Toolkit


Built with no-code using Webflow 💙
© 2023 Product Lessons