The Founder I Vouched For

On the difference between a strategy problem and a person problem, and why it took me too long to see which one I was looking at.

In February 2022, I sat down with a founder who’d been running his company for four years. He told me the business was steady. Growing. The story founders tell when they want you to believe the hard part is behind them.

It took me a few more conversations to understand how far that was from true. Underneath the story, the company was still essentially pre-revenue. Four years in.

I didn’t catch it right away.

But once I started paying closer attention, a different pattern showed up, and it wasn’t a strategy problem.

He was sharp. The kind of founder who could out-argue you on an architecture decision before you’d finished your coffee. But he’d built the company around what he found interesting to build, not around what any customer had actually asked for. And the less the numbers moved, the more certain he got that he was right and the market was slow to catch up.

Somewhere in those four years, I introduced him to one of my own contacts. Someone I’d worked with, vouched for, put my name next to. That relationship didn’t survive contact with him. He wasn’t the only one of his clients this happened to. But that one was mine to answer for.

By the time the board caught up to what I’d been watching for months, the question wasn’t how to fix the plan. It was harder than that: what do you actually do with a founder who is talented, half right about his own business, and the reason it isn’t working?

Below the line is the framework I built from this so I’d catch it earlier next time, and how the story actually ends: the repositioning, the three years, the number.