The Trenches —
the cost of building.
The conversations no one has. The struggles everyone hides.
Burnout. Loneliness. Breakdowns. Co-founder breakups. Marriages that didn’t survive scaling. Depression that didn’t end with the exit. The dark side of building, on the record.
The crisis is real, dataset-validated, and under-served.
Most coverage of founder life is the highlight reel — the raise, the launch, the exit. The Trenches starts with what the data actually says about what it costs to be the person inside that highlight reel.
The conversations you’ll actually hear.
Six territories. Twenty-plus episodes already mapped. Each one a real conversation with a founder, operator, investor, or partner who lived through it — on the record, with their name on it. The territory the show covers, in plain words.
The interior reality of building
- The 3am Panic Attack
- The Loneliness
- I Thought About Quitting
When the people closest to you become the breaking point
- I Fired My Co-Founder
- Imposter at My Own Company
What building takes from home
- My Marriage Ended
- The Depression After Exit
The pitches you don’t recover from
- 200 No’s Before One Yes
- When Your Investor Ghosts
- The LP Pressure
The cameras-off truth from the cap table
- Why I Passed on [Unicorn]
- Red Flags I Ignore
- My Worst Investment
- The Founders I Wish I Backed
Where the startup machine produces the breakdowns
- Accelerator Theater
- Demo Day Theater
- Toxic Term Sheets
- The Ecosystem Gatekeepers
First episode drops soon.
We’re recording the first 6 episodes before public launch. The first 100 waitlist members get an early-access link to the pilot, plus a private email thread with the host where you can suggest guests, topics, and stories you want told.
The pilot drops to the waitlist before Spotify, Apple, or YouTube.
If you’re going through any of this — or you watched someone close to you go through it — drop your email. We’ll send you the first episode the moment it lands.
One email when the show launches. Zero spam. Easy unsubscribe.