Anti-Cacophony Partners
The Hardest Good Call I Ever Made
People assume the hardest part of being a fractional COO is the spreadsheets, or the board decks, or the 2am cash-flow scrambles. Honestly, most of that is the fun part. The hardest part is the conversation where you tell a founder something they don’t want to hear, at a moment when hearing it costs them everything they’ve built.
I had that conversation with a founder I’ll call the CEO of Waggle, a consumer social app for pet owners. It remains, to this day, one of my favorite roles I’ve ever had. Great product, great team, a founder who listened and led well. We had real traction. What we didn’t have, when it mattered, was the user growth inflection point we needed to credibly raise the next round.
I’d run the model a dozen ways. I kept hoping a different set of assumptions would get us somewhere else. It didn’t. Runway was finite, the metrics weren’t moving the way a Series A story requires, and no amount of optimism in a pitch deck was going to change that. So I told the founder what the numbers were telling me: we weren’t going to raise on this trajectory, and the responsible move was to wind the company down and get what value we could out of an asset sale, rather than burn the remaining cash chasing a round that wasn’t coming.
He agreed, and it was the right call — but it wasn’t an easy one for either of us. He had to tell his team. I had to help him do it in a way that was fair to them and to the company’s investors. We ran a real process: an orderly wind-down, a sale of the company’s assets, and an outcome that returned some capital rather than none. The buyer, as it happens, kept the Waggle name and still uses it today for their pet camera product line. Somewhere out there, dogs are still being watched under a name I helped put to rest as a company.
Why I still count this as a win
It’s tempting to only put the raises and the exits on your track record. But the job of a CFO or COO isn’t to manufacture good news — it’s to give a founder the clearest possible read on reality, early enough that they still have options. The founders I respect most aren’t the ones who never hit a wall. They’re the ones who, when they hit it, make the deliberate choice instead of the desperate one.
A few things I’d tell any founder facing a similar moment:
- Don’t let hope substitute for a model. If you’re re-running the same numbers hoping for a different answer, that’s a sign you already know the answer.
- An orderly wind-down is a decision, not a failure. It preserves value, protects your team’s reputation and your own, and gives investors something back instead of nothing.
- How you leave a company matters as much as how you built it. Every person on that team, and every investor on that cap table, will work with you again someday. Handle the ending with the same care you’d want for the beginning.
- Get an outside read before it’s a crisis. The earlier a founder brings in someone who’ll tell them the truth about their numbers, the more options they’ll have when it counts — whether the answer is “raise” or “wind down.”
I don’t know that I’ll ever have a role I enjoyed more than Waggle. Not because it ended the way any of us wanted, but because I got to help a founder make the hard, right call instead of the easy, wrong one. That’s the job, even on the days it doesn’t look like a win from the outside.