Five Unexpected Lessons From Building a Family Business
What I've learned from working with my sister at Monica + Andy these past 14 years.
1. It’s a great way to stay close.
Life is busy. Jobs. Spouses. Kids.
One unexpected benefit of family business: you talk constantly and see each other more than you otherwise would.
Daily texts.
Daily calls.
Quick zooms.
Long dinners.
Grueling board meetings.
You see each other’s faces. You hear each other’s voices. You stay in much closer touch. It’s an excuse to stay connected.
That alone is underrated.
2. It’s a petri dish for conflict. And conflict equals growth — if communication is good.
If you don’t communicate well, it’s a disaster. Negative feelings compound. Rifts form. Chasms widen. Families get frosty. Or fall apart.
If you don’t have deep mutual admiration, a shared belief that business is not the most important thing in life, and the ability to navigate difficult conversations with candor and respect, don’t do it.
One upside: the company forces those hard conversations. And that skill compounds well beyond the business.
Conflict handled well is intimacy. Conflict handled poorly is corrosion. The business creates a forum for conflict that siblings might otherwise avoid entirely.
3. Money can’t be the primary motivation.
The mission of the company has to matter more than the money.
Families that ultimately view the business as a zero-sum game about who owns what and who makes how much are in trouble.
This is why second and third generations in wealthy families often suffer.
They didn’t fight for that wealth.
They fight over it.
They’re often not as tight as the first generation.
So they don’t always develop the grit and the wisdom that built it.
4. It’s better if there’s one CEO.
One reason Monica + Andy works is she’s the founder and CEO, and I’m her cofounder and chairman.
My name may be on the door, but it comes second.
I know a lot of siblings both operating full-time in the same company. Sometimes with a parent as their boss!
I have no idea how people do that. I’ll leave those lessons to them.
I’d go nuts. I’ve seen it go badly with several sibling duos I know (though not all of them).
5. Note to the non-full time sibling: be a coach, not a savior.
I love Diana Chapman’s framework that a hero requires a victim. I’ve learned over time that if Monica is facing a tough moment, my job is to be Phil Jackson.
Vital to the victory.
But from the sidelines.
She’s Michael Jordan.
Her team is the Bulls.
They win on the court.
I coach. I give tough feedback. I celebrate the wins.
But I’m not playing.
They’re the ones on the court.
The victory is theirs.
This will be a three-part series. More next week.
Hi I’m Andy, a founder of Bonobos, Pie, Monica + Andy, and Red Swan — and the author of Burn Rate: Launching a Startup and Losing My Mind, a memoir about building companies while navigating bipolar one. Here my Ted talk — and my podcast, Humble Pie: Everybody Eats It — about how the worst things that happen to us can become the best things, but only if we tell ourselves that story. I love cilantro but love even more the people that hate it. Go Bears.

