The Emotional Cost of Finding Product-Market Fit

It takes a lot to take the leap and start a company. And knowing when to pivot is the single hardest problem in startups.

But what will weigh on you the most is just how bad it will feel until you find product market fit. It feels like pushing a boulder uphill while wondering whether the boulder wants to move at all.

Yes: the tasks you’re required to do as a founder don’t get easier. They get harder. Managing 500 people is less intuitive to most people than managing 50 people, and so on.

But one thing does get easier: it just feels better. Success and traction—even through adversity—don’t make you question whether you should be doing this at all. But when you’re just getting started, every blip of failure feels like it’s just about you.

Should you be spending your time on this, when all your friends are joining startups that just announced their $50m Series B? Can you keep convincing (or is it tricking?) early team members to bet their careers on your idea? And how many times will you allow your spouse’s friends to ask you “how it’s going”?

You’re one year in and your marquee customer has threatened to churn again. You’re gaining weight and your friends are getting rich. Was it worth it?

You’ll meet founders at this step in their journey and they seem beaten down. Nothing like their a16z produced AI- slop launch video about how their parents owned a small business inspired them to get rich selling software. No, they look tired.

I was recently struck by two articulations on what makes a successful entrepreneur.

The first was from Bending Spoons’ S-1:

Luck plays a big role in finding product-market fit. We’d observed phenomenal entrepreneurs fail in their ventures and less remarkable ones succeed. Even accepting that our own judgment was flawed in some cases, it was apparent that luck mattered a great deal at the early stages of a business.

For Bending Spoons, this realization about the role of luck in the PMF search led them to focus on execution of other founders’ ideas instead of their own.

The second idea, from Noubar Afeyan (the founder of Flagship Pioneering, a biotech incubator), is that entrepreneurship is something you can practice:

People used to think that people were born with a predisposition to be an architect or doctor, as opposed to learning, perfecting, improving the practice of architecture or medicine. When people say of entrepreneuring, “Yeah, but you can’t create a Bill Gates,” the answer is, that’s true. You also can’t create a phenomenal brain surgeon. That doesn’t mean that people can’t do brain surgery. People can learn how to do brain surgery, and the phenomenal ones will always be phenomenal. It’s a complete misunderstanding to think that the only way you can be a phenomenal brain surgeon is to have no preparation and wing it.

These two quotes encapsulate why it feels so hard to be in the earliest state of a company. In finding product market fit, unusual effort isn’t directly rewarded and entreneurship seems like something you’re supposed to have a natural gift for. You wonder if you were meant for this.

And the first part is true. A lot of finding product market fit is luck. But that doesn’t mean all hope is lost. Just because it feels bad doesn’t mean it is bad, and it is something you can practice and get better at.

I’m still not sure I can help find others find product market fit - it remains the single hardest problem in startups.

But I’m now approaching my fifth time with a front row seat to the search, and I can at least help you apply some emotional bubblewrap to cushion the next blow.

Here are a few ideas that have worked for me:

• Use a bounded time period with a specific hypothesis to test. For example, in the next week, we’ll speak with 7 customers who we think have this need. Don’t raise any bigger questions except the narrow one you’re focused on during that time period.

• Like in tennis, you want a ‘loose grip’. Holding tightly enough so you don’t let go even during contact but loose enough so you respond to the ball. In startups, that means forgetting the idea you pitched, at least just a little bit. Don’t hold on so firmly to the pitch deck - treat it like a set of mini hypotheses to verify.

• One really weird thing is that when things are really not working, you need to work less, not more. The first time this happened 11 years ago, I felt super guilty. Everyone spoke about how hard you had to work, and that seemed like the only thing in my control. And that’s certainly true when you have product market fit, and you know what to do. But when you don’t, it’s counter productive. When you don’t have product market fit, you need to speak to customers and give yourself space to think.

• Have a co-founder. Early stage emotions are almost always overfitting to limited data. There’s just very rarely a single thing you can learn - in either direction - that changes everything. Yes, there are those good and bad days - but a big part of having a co-founder is just to help you remember the journey you’re on together. Even your friends and partners will eventually get tired of hearing you.

Good luck out there.