Most founders lose their edge the day the Series B (or PE) wire hits.
I did. Strong up-round, board observer added, cash suddenly easy, comp bands that screamed "we made it."
Created "All-Hands Support" rotations: every employee, including me and the board observer, rotated through live customer support tickets to feel daily pain points first hand
Rule for all new VPs: shadow me on at least three live customer calls in first 30 days—no exceptions
Just like that, AI changed everything.
Yesterday, blockbuster effects required studios and massive budgets.
Today, a laptop and an AI tool can do the same thing.
Some see creativity unleashed. Others see trust unraveling.
Here’s a secret they don’t put in the pitch deck:
It doesn’t matter how many exits you’ve had—
Every new company comes with a fresh dose of insecurity.