Chapter 8: Things I Say to Founders

Most of Breakfast With Pops has been addressed to other VCs and aspiring VCs— not to founders. That’s because a good investor avoids telling founders how to do their jobs. But there are a handful of things I say to founders. Here they are.

  • “A lot of entrepreneurs make the mistake of protecting the board from bad news. If you don’t remember anything else I’ve said, remember this: get the bad news out fast.” — Pops

  • “The chairman of the board probably should not be you. It should be somebody you can talk to over lunch in a tough situation.” — Pops

  • Perfect is the enemy of done.

  • You will eventually need to stop
    “doing everything.” In the early days
    of a startup, especially for first-time founders, there’s self-confidence in understanding everything that goes
    on under the hood of your company. The early days are when you establish your obsession, and begin building your seedling brand. You take pride in the “doing everything” mentality. However, championships are won by teams, not individuals. In order to scale yourself, you have to trust the people on your team to be better than you at doing everything. They should be All Stars who challenge you.

  • Someone out there loves doing the job you suck at.

  • Seek criticism rather than fighting it.

  • Be thoughtful, but default to movement.

  • VCs are NOT your customers.

  • Product-market fit is a kid selling ice- cold lemonade on the hottest day
    of summer. Everyone who stops at the lemonade stand has 2 things

    in common: (1) they’re supporting someone they think is worth supporting, and (2) they want the damn lemonade. When you have product-market fit, you’re providing something people need, not what you thought they needed.

  • Finally: Be the cockroach! That’sour motto at Boost. It’s one of the first things I see every time I walk into our office.

“Be the cockroach” came from a startup called Favor. They were in the crowded market of the on-demand food delivery space, but carved out their own space outside of California and made their way to a good exit.

However, before they had any semblance of success, they lived in every office they ever had and ran out of money twice; also, every time we connected with them, we weren’t sure if they were headed in the right direction.

But we always ended up saying—“But they won’t die,” and we started calling them cockroaches. Then, we realized they took pride in being cockroaches.

Ben Doherty, one of the co-founders, said, “Yeah! We’re like cockroaches. The funny thing about cockroaches is they’re really hard to kill, and no one likes them in their space.”

And suddenly, we took pride in calling our companies cockroaches. We defined a cockroach as a resourceful startup that survives no matter what. The competition ignores them, yet fears they’ll enter their space. They’re awake day and night. They’re quick, agile, and good at adapting to their environment.

Come what may on planet Earth, one thing that won’t change is the nature of cockroaches. The nature of great entrepreneurs is similarly unchanging. And wherever they exist, there will be people like Pops, my dad, me, and maybe you, who love to see them win against all odds.