The number one quality of a founder is grit. But that same quality is what makes it almost impossible to tell the difference between “this isn’t working yet” and “this isn’t going to work.”
Today, Kevin walks through the compounding moments that turned into dread and the moment he finally called it.
What Kevin made me think about:
There’s a difference between a hard path and no path at all. And the only way to know which one you’re on is to stop and reflect long enough to see.
Prolonged fundraising is often the first honest signal. Kevin’s reframe: put yourself in your investor’s seat and ask, would I fund me right now? The answer usually tells you everything.
Becoming a founder means building a new identity. Ending it means shedding that identity — which is painful, but, eventually, freeing.
Resilience isn’t outlasting the shutdown. It’s being able to close the chapter and talk about it out loud.
Next Friday — Chapter 1.3: What If Pivoting Is More Elusive Than You Think?
Kevin on why pivoting sounds simple, and really isn’t.





