Every founder runs into this moment.
Sometimes the answer is clear. The market shifts overnight. Customers stop buying. Reality forces your hand.
But most of the time? It’s not that simple.
Things are sort of working. You’ve got some traction, but not what you expected.
So when do you make the call to shift?
I asked Patrick Samy, an exited second-time founder, how he approached this moment. His startup, Span, went through a major pivot before being acquired by Eight Sleep.
Here’s what he shared:
“Pivot versus push is a harder question for me. There are obvious moments—like the first COVID lockdown—where we had to pivot or we would’ve shut down in 8 months. Or when no customers are willing to pay for your product. Those decisions are easy.
The hard ones are when things are sort of working. You're getting users, maybe some revenue—but not exponential growth. Not the excitement you expected.
In those moments, you have to spend as much time as possible talking to customers. Dig into the reasons why they’re not paying. Why they’re choosing other solutions. Why they aren’t sticking around.”
That’s the key: customer obsession.
Ask yourself:
Are they interested, but hesitant because of the price?
Do they love the idea but wish it solved a slightly different problem?
Are they signing up but dropping off quickly?
Sometimes, it’s a small tweak—messaging, onboarding, pricing—that unlocks real traction. But if you keep running into a wall, and the feedback says customers don’t see enough value, that’s when it’s time for a bigger pivot.
If you’re not getting the response you want—ask why. Not once. Over and over.
Customer truth is the best signal.
Thanks for reading. I’m Michelle from Menlo VC. Follow me here for more founder spotlights and insights from the journey.
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