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Become a member →The day I stopped funding my own startup
"I realized the company wasn’t what I wanted. It was what I had become good at wanting."
A — former co-founder, B2B SaaS. Raised $14M across two rounds, ran the company seven years, and walked away the week before the Series C term sheet was due. Now teaches one course a year at a state university and refuses to consult.
I was the most senior person on the call
"Severance is the company saying “we are paying you to leave.” My job was to figure out what I was being paid to do next."
B — former CFO, public company. Twenty-two years at one company, the last eight as CFO. Took the severance package the morning after the third reorg and hasn’t taken a board seat since. Now writes a quarterly essay that 6,000 people read and nobody pays for.
The last race I ever ran
"I knew with one mile left. I finished the race because I wanted to know what the last mile of my career felt like."
C — former pro distance runner. Two-time Olympic team alternate. Retired at 31, the day after a race she finished. Now coaches college runners and refuses to coach for a fee.
I finished the novel and stopped writing
"The fourth book was the one where I had nothing left to argue with. So I closed the file."
D — novelist. Three published novels in twelve years. Finished a fourth manuscript, decided not to publish it, and has not written fiction since. Currently working at a public library reference desk.
The tenure track I walked off
"The tenure case wasn’t the thing I was scared of. It was the next thirty years on the other side of it."
E — former associate professor. Eight years tenure-track at an R1, two years before her tenure case, walked. Now runs a small grant-evaluation practice — three clients, by referral only.
I resigned from the bench
"A trial judge is the loneliest civil servant in the country. The day I resigned was the first day I was alone for a reason I chose."
F — former state-court judge. Eleven years on a state trial court. Resigned mid-term, declined to stand for re-election, and has not practiced or taught since. Reads three books a week now.
The second album I shelved
"The label heard the master before I did. By the time I heard it I already knew the album would never be the thing they wanted to sell."
G — former indie musician. One critically acclaimed album, eighteen months of touring, and a second album recorded but never released. Quit the day after the master was delivered. Currently teaches piano in an after-school program in Pittsburgh.
The deal I did not sign
"The extension was generous. That was the problem."
H — former managing partner, mid-size law firm. Thirty-one years at one law firm, the last seven as managing partner. The week he was meant to sign a four-year extension, he resigned. Now runs a one-person mediation practice. Carries no cards.
199 more episodes back to ep. 1 (December 2022). Every episode searchable, transcripted, and chapter-marked, behind the membership wall.
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