Archive
Episodes
New episode airs every week.
Episode 009
Alana Picov
Good Greed
Left Salesforce. Now Every Problem Is My Problem.
Episode 008
Cam Stajer
Kala Therapy
The $20 Logo That Became an Olympic Sponsor
Episode 007
Ilias Anwar
Anwar Events
His Company Died in One Night
Episode 006
Brian Schardt
Autopilot
He Killed 250K Users to Bet on Nancy Pelosi
Episode 005
Sabih Siddiqi
Irys AI
Why a 'Safe' Job Is the Most Dangerous Bet
Episode 004
Rei Lalo
TRIHARD
He Quit a Top Ad Agency to Bet on a Category That Didn't Exist
Episode 003
Clarke Pennington
Lasso
Hedge Fund to Founder: Building Lasso in 11 Months
Episode 002
Kirsten Breidenbruch
Wellth by Kirsten
VP at BlackRock to Quitting With No Plan
Episode 001
Arsh Toor
Stesh Pistachio Butter
Her Dad Would Have Killed for the Job She Quit
Coming Fall 2026
Dave McKitrick
Shelter Investments
Coming Fall 2026
David Hogsett
Sesh Comedy
Coming Fall 2026
Jared Lerner
Nappr
Coming Fall 2026
Julie Wainwright
The RealReal
Coming Fall 2026
Kiki Couchman
Sourmilk
Coming Fall 2026
Liesel Vaidya
Imera
Coming Fall 2026
Venus Rose
Haus of Creators