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Founder Blind Spots: The Psychology of Outliers

Tuesday, February 17, 2026 · 4–7 PM PST

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About this session

Founder Blind Spots: The Psychology of Outliers


Why This Matters

You've built something remarkable. You've scaled revenue, hired great teams, and you're approaching or thinking about an exit. But here's what most founders don't talk about: roughly 90% of the critical mistakes made during and after exits aren't about strategy or market dynamics—they're psychological.

Identity crises. Hero complexes. The inability to let go. The shock of sudden wealth. The existential void that comes after the finish line.

These aren't character flaws. They're predictable psychological patterns that derail even the most successful founders—and they're preventable.

What You'll Learn

Join Dave Hersh, founder and former CEO of Jive Software (IPO 2011, $60M+ revenue) and current executive coach and venture investor, as he breaks down:

  • The psychological blind spots that cause founders to fumble in the final stretch before exit
  • The post-exit identity crisis that catches 70% of founders off guard—and how to navigate it
  • The exit wound: why the moment after you "win" is when you're most vulnerable
  • Practical frameworks to protect your mental health, your relationships, and your next chapter—whether that's inside or outside your company

Dave has coached dozens of founders through exits and witnessed the patterns firsthand. He's also lived them. After taking Jive public, he spent 10 years in an existential crisis before achieving real clarity. He's here to help you skip that part.


Who Should Attend

  • Series A/B founders thinking about or actively preparing for exit
  • Founders who've hit product-market fit and are scaling fast

David Hersh

Hosting this session

David Hersh

Founding CEO of Jive Software, Self employed

Dave is the author of Reignition (Inc. Originals Press, April 2024), a practical and deeply-researched playbook for helping startups and growth companies get “unstuck” and find their path. He is a general partner at Metamorph Partners, was the founding CEO of Jive Software (NASDAQ IPO in 2011), served as a board partner at Andreessen Horowitz, and has advised hundreds of startups over three decades.

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For companies that have raised at least $1M from venture firms.