“I left Lehman because the culture rewarded FaceTime and managing-up over doing excellent work, and I never wanted to build that again. At Lyft, we made it simple early on: be yourself, uplift others, make it happen. That wasn't just nice; it was how we attracted people who could out-execute teams ten times our size.”
“Early culture isn't the values you write on the wall; it's the behavior you tolerate when no one is watching. At Flexport, I watched the revenue team become a culture of service because we spent every waking minute in front of customers together, not in the office theorizing about it. If you want a culture, put your people in the shit with you and let them see what you actually reward.”
“Culture in the early days is not perks or a ping-pong table; it is the behaviors you tolerate and the people you hire. I learned at 1-800-GOT-JUNK? that if you hire for culture fit and fire fast when someone breaks the values, the team self-polices. Get four or five core values your people can actually remember, then hire, praise, and fire against them from day one.”
“At Brex 3.0, I learned culture isn't a value statement you put on the wall; it's the selection pressure you create by what you actually do. We went back in person, I edited the roadmap directly, and we told people the work matters more than the org chart. A lot of people left, and that was the point. The ones who stayed were the believers, and they amplified the thing we were trying to build.”
“The main thing is don't panic. Culture isn't some mystical separate thing from what you're already doing on the product side. If you're thinking experience-focused and design-focused about your product, extend that same lens outward—to how people first hear about you, to how your team collaborates, to what you actually trust each other to do.”
“Culture in the early days is not a values deck or a foosball table; it is the conditions you create so the right people can be themselves and do great work together. I have hired north of 200 people across my companies, and the only thing I know for sure is that you cannot design culture directly.”
“Culture in the early days isn't something you decide on a whiteboard—it's what you actually do when the stakes are tiny and the money isn't there. When we ran Dixon and Moe on a shoestring with no clients, we still kept Fridays off because that's how Monograph got built—you can't expect people to hustle and think clearly if they're running on empty.”
“In the early days, culture is just who's in the room and whether they're buying in to what you're doing, not some mission statement. You hire people who move fast, push back on your bad ideas, and stay focused on whether anyone actually gives a shit about the product—everything else is noise.”