Graduating business school, I had $150,000 of debt. An investment firm offered me a steady job, but it didn't feel right. It was 2007 in Silicon Valley, and I dreamed of starting an Internet company.
Most of the time, when you need something at a company, you make it. If you want to sell a product, you create it. If you need a head of marketing, you hire one. If you want to create a great company culture, what do you do? The lack of a clear answer on this is why I believe most companies don't have a great culture.
I've been in thousands of conversations dripping with misogyny. I've initiated many of those conversations myself. From my fraternity roots to my bachelor days in New York, I know I have not always shown up in ways that I am proud of.
You don't think, when you start a company as the founding CEO, that if your venture actually works, you end up with three jobs: founder, CEO, and chair of the board. The first eight years at Bonobos, I have learned a lot about the tension between the first two. It didn't even occur to me that I had the third job until much later.