Building

Killing Your Own Bet

Published on Apr 20

Last August, I joined a town hall and told the team we were killing the biggest strategic bet I'd ever made as CEO.

We'd spent a year researching, testing, and iterating on a new business model — one we thought could set the company up for the next decade. It was a full-send moment: dozens of people working nights and weekends, a brand new pricing page, customer communications, internal enablement, the works. I'd pitched it to the team, the board, customers, and anyone who'd listen. This was the future of the business.

And then customers told us it wasn't.

Several KPIs looked promising, but there was a slow, undeniable accumulation of feedback in the other direction. Adoption wasn't where it needed to be. The story wasn't landing the way we thought it would. We'd been tuning, iterating, talking ourselves into patience. Then, the data stopped being ambiguous.

That's the moment most founders get stuck. You stood up and told everyone this was the plan. You built the team around it. You asked people to sacrifice for it. Reversing course doesn't just feel like admitting you were wrong. It feels like undoing a year of everyone else's work.

So you wait. You run one more experiment. You ship one more iteration. You tell yourself the narrative will start clicking.

Meanwhile, the engine of the business keeps sputtering, and every week you wait, the damage compounds — to the P&L, to the team's trust, to your own clarity.

The most underrated CEO skill I know is the ability to reverse a year of your own work without flinching when the evidence is in. Not recklessly. Not prematurely. But cleanly, and in public, and with enough conviction that the team can follow you into the pivot with their energy intact.

When we announced the change that August, I expected a hard conversation. What I got instead was a Slack channel full of "we've got this" and "I'm all in." The team didn't need me to pretend the first bet had worked. They needed me to own the outcome and point to the next thing.

Ego will tell you the announcement is the hardest part. It isn't. The hardest part is being honest with yourself at the earliest moment, when you can still change the story.

Make the call sooner than feels comfortable. It's almost always the right move.