Pro Basketball to 5x Founder: A Masterclass in Resilience | Jordan Fliegel

At 28, Jordan Fliegel had a career-ending injury behind him, thirty employees in front of him, and a startup he loved so much he lived across the street from the office so he could be the first one in. Then his board told him they were replacing him as CEO, and offered him three to five million dollars at a higher valuation if he'd stay quietly and help pick his own replacement. He said yes. Not because he agreed with it, but because saying no meant firing the people he called family. He's never talked about it publicly until now. Jordan is the founder of CoachUp, former co-CEO of DRAFT, and now the founder and CEO of Acquisition Lab, where he helps people buy small businesses instead of starting them. In this conversation with Mark Phillips he walks through the whole valley: the demotion, the year he spent as a president whose title meant nothing, the nine months he slept in a Manhattan office while his next company was insolvent, and the day he finally came back and removed the investors who removed him. In this episode: The napkin math that shows exactly when your investors' incentives stop matching yours Why he ran through Boston in tears to a mentor's office with no appointment What it feels like to sit in meetings where every good idea you offer undermines your own successor How he told ten employees the money was gone, and what he had to say to the one he couldn't save The letter his mentor wrote him, read out loud for the first time Why he took a company from "we can't pay our bills" to a $48M exit The Jocko Willink rule he now applies to every piece of bad news Subscribe for new episodes of Through the Valley every week. Watch on YouTube, listen on Spotify and Apple Podcasts. Timestamps: 00:00 Intro 02:21 CoachUp was his identity 03:48 What the stress was doing to his body 06:59 When investor incentives stop matching yours 07:53 The middle range, where founders get replaced 08:47 The board’s offer, and helping pick his successor 09:42 Why he said yes: the thirty people he hired 12:24 The napkin math on preferred stock 15:55 President and chairman, “which means nothing” 17:04 Every good idea undermining his own replacement 19:04 What boxing taught him about getting hit 20:02 Running through Boston to his mentor’s office 21:40 The letter, read out loud 25:24 Telling ten employees the money was gone 26:00 Out of money, and the flight to California 26:56 Buying back in, and the turnaround 33:20 Start it, join it, or buy it 35:17 Fall in love with the problem 41:27 Building Acquisition Lab 46:08 The injury that ended his playing career