5 Lessons From 5 Years of Building 82i

Five years ago this month, I left a career in investing to start 82i. I had no idea what I was doing. I had a list of 82 ideas, enough runway to get started, and a strong sense that I wanted to be closer to the work than investing allowed.

Five years and 150+ clients later, here are five things I wish I had understood on day one.

1. Go with the tide

The best founders I work with don’t try to force the market, their team, or their product into a shape it doesn’t want to take. They listen, adjust, and find the creative path that uses the momentum already there. Fighting the current burns resources you can’t afford to waste at this stage.

2. Persistence compounds

Every day you stay in the game, your experience, relationships, brand, and judgment all build on each other. I didn’t appreciate this in year one. By year three, it was obvious. The founders who win are usually the ones who simply kept going when others quit.

3. Know your value

Most founders I meet either over-estimate or under-estimate where their business sits. Both are expensive. Investors, employees, and customers all read confidence calibration before they read your deck. Get honest about what you actually have, then communicate it clearly.

4. The hustler has to die for the CEO to live

For a long time, everything flowed through me. The business grew anyway, but I was the ceiling. Slowing down, building a team, and resisting the urge to do it all myself made me a better leader and made 82i a better firm. It’s still the lesson I have to relearn most often.

5. Hire for growth and openness

I’ve stopped trying to evaluate experience, pedigree, or specific skill sets in isolation. The people who do the best work at 82i are the ones who want to learn and stay open to being wrong. Everything else can be taught — and five years in, this is the filter I trust most.

Grateful to the team, our clients, and the founders who took a chance on us early. Five years in, I’m more convinced than ever that this work matters.

Onto the next 82!