Episode 381: The Psychology Behind Successful Exits with Dave Hersh

What if losing your life savings on your first investment at age 27 became the catalyst for understanding why 90% of startups get stuck for the same psychological reasons? That's exactly what happened to Dave Hersh, founding CEO of Jive, board partner at Andreessen Horowitz, and author of Reignition.

Dave grew Jive from an open-source project to a NASDAQ IPO, bootstrapping to $12 million over five years before raising venture capital. But when he watched Atlassian, a comparison company that started at the same time, stay on their original trajectory and become worth over $20 billion while Jive eventually died on the public markets, he realized fear and insecurity had driven his capital decision rather than genuine strategy.

That painful lesson shaped everything Dave now teaches as an executive coach and General Partner at Metamorph Partners. After working with hundreds of stuck companies, he discovered that 90% of failures trace back to the same psychological patterns. Not cash. Not product market fit. Not competition. Subconscious patterns driving decisions without founders knowing.

The statistics are sobering. Between 80 to 95% of founders suffer mental health issues while running their companies. Even successful founders have an 85% chance of experiencing depression or struggles for up to 10 years post-exit. Only 15% are truly thriving after they sell.

Dave introduces his inner board meeting framework, which helps founders identify the internal parts driving major decisions. The child wanting safety. The hero wanting to save everyone. The warrior that cannot let go. When you understand these patterns, you can work toward compromises that break through stalemates.

The conversation covers when and why to raise capital versus bootstrap, the transition process between identities that most founders skip, and the human-first competitive moats that will define success in the AI era.

For founders navigating capital decisions, stuck companies, or the complex terrain after exit, this episode offers a different lens on what actually determines outcomes.

FOR MORE ON THIS EPISODE: https://www.coreykupfer.com/blog/davehersh

FOR MORE ON DAVE HERSH:https://www.linkedin.com/in/davehersh/https://one-in-ten-thousand.beehiiv.com/ 

FOR MORE ON COREY KUPFERhttps://www.linkedin.com/in/coreykupfer/https://www.coreykupfer.com/

Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

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