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Bret Taylor: The Hardest Part of Being a Founder Is Managing Your Own Psychology

By Bret Taylor · Startup Growth · 1 min read

Taylor says the failures aren't what kill you. It's how personally you take them. He and his cofounder spent as much time investing in their relationship as they did in the company.

Key Points

The hardest part of being an entrepreneur is managing your own psychology
You take failure personally when it's your company and your product
Finding a cofounder you can go through the struggles with is the most important decision

The hardest part about being an entrepreneur is managing your own psychology. I take failure very personally when it's my company and my product.

You Remember the Rejections

Taylor: It's so grueling. The hardest part about being an entrepreneur is managing your own psychology. It's so hard. I take failure very personally when it's my company and my product.

It's so hard not to become dejected with rejection. You're raising money, you get rejected by 75% of the people. It doesn't matter — you only need funding from one of them. But all you remember is the rejections.

Then you're trying to sell the product. You get a bunch of noes. Or usually it's not even a no — they don't even grace you with an answer. They just don't return your call. And that's what you remember.

You get rejected by 75% of the people. You only need funding from one of them. But all you remember is the rejections.

The Cofounder Decision

Taylor: The main thing I did differently with my second company is I thought so intentionally about finding a cofounder. Someone I knew I could be metaphorically married to for a long period of time. Not only a partner in business but a partner through the struggles.

The last thing you need is a founding team with drama on top of all the drama that's inherent in starting a company. My cofounder Kevin and I spend as much time investing in our relationship as we do in the company. It's been the anchor that has kept us stable through all the inevitable failures.

We spend as much time investing in our relationship as we do in the company. It's been the anchor through all the failures.

Grit, Not Pivoting

Taylor: The thing we had that was valuable was grit. When something failed, we would diagnose it and move on to the next thing. We weren't pivoting. We were moving forward but changing our angle slightly.

We were really committed to our mission. The productivity suite was invented in the 80s. It was the killer app for the PC. We knew there would be a successor in the mobile era. When you have the vision and the commitment, you're willing to tolerate failure in the middle because it's not an existential setback. It's a tactical setback.

We weren't pivoting. We were moving forward but changing our angle slightly.

The Proverbial Couch

Taylor: We spend a lot of time on the proverbial couch in psychiatry sessions with each other. 'It's okay. You're not a failure.' Talking each other through it.

People don't talk about it enough because it is so trying. You come home, you feel dejected and defeated. And it's okay. Everyone does it. Finding a cofounder or friend you can talk to about it is super meaningful.

You come home, you feel dejected and defeated. And it's okay. Everyone does it.