/ Episode 207 just published · April 22, 2026
A solo-host weekly podcast. 207 episodes deep. The decision, not the highlight reel. Transcripts included. No filler.
90-minute average. Founders, executives, athletes, artists, judges. One guest at a time. Recorded since 2022.
/ The thesis
Quit something serious — stayed to talk about it.
Most podcasts about quitting are about transformation. This one is not. The guests on Cypress Hour walked away from things they had built — companies, careers, relationships, public roles — and stayed close enough to the decision to talk about what it actually was. Not what it became, in retrospect, after the years had filed off the edges.
We record a long conversation. We publish a long episode. We include the transcript. We do not edit out the second-thoughts, because the second-thoughts are the whole subject.
The archive is searchable. You can filter by the type of choice — founder walkaway, executive severance, athlete retirement, artist stop, academic exit, public-service exit — instead of by industry. Industry is the wrong axis. The choice is the right one.
/ Featured · Episode 207
founder walkaway · B2B SaaS · 94 min
"I realized the company wasn’t what I wanted. It was what I had become good at wanting."
Guest: 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.
Preview · 1:24 / 94:00
/ Recent episodes
All 207 →Raised $14M across two rounds, ran the company seven years, and walked away the week before the Series C term sheet was due.
Twenty-two years at one company, the last eight as CFO.
Two-time Olympic team alternate.
Three published novels in twelve years.
/ Four years in
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weekly listeners
paid members
avg minutes / episode
Listener counts and member counts are illustrative — this is a portfolio demo. The product surface is real.
/ From the journal
2026-03-04 · 7 min read
Why episode 200 is the guest who has the least to say in the loudest possible way — and why that was the only correct choice.
2026-02-18 · 9 min read
Most podcast sites are a paginated feed. Cypress Hour is an archive — built so you can find the conversation about the choice you are considering, not the latest episode.
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