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 Reignitio…
#175: The Hidden Founder Psychology Patterns Behind Stuck SaaS Companies - Dave Hersh
Dave Hersh, co-founder and former CEO of Jive Software, shares the real story behind bootstrapping Jive to $12M in revenue before raising venture capital and scaling aggressively. He explains how fear, comparison, and the pressure to "go big" drove him to abandon his profitable core business and pu…
Episode 384: Happy Holidays DealQuest Family
About fifteen years ago, I gave up the conversation around balance entirely. The word I use instead is integration, and in this holiday episode I share why that shift transforms how entrepreneurs experience everything from year-end deal closings to family obligations.
In this holiday episode of th…
Why Startups Get Stuck & The Pitfalls of Raising Money
Have you ever dreamt of launching a startup but worried about the dangers of scaling too quickly? Or maybe you're already running a business that feels stuck, unable to reach its full potential.
This is the podcast for you. Join host Matt Watson as he explores the fascinating world of entrepreneur…
Building with instinct while scaling with best practices w/ Yoni Tserruya, Co-founder and CEO of Lusha
This episode of The Art of Entrepreneurship is for founders who feel caught between following best practices and trusting their instincts as they scale.
My guest is Yoni Tserruya, co-founder and CEO of Lusha, an AI-powered sales intelligence platform used by millions of sales and RevOps professiona…
Episode 402: Building a Transferable Business and Surviving the Exit with Nate Collins
From buying into a mismanaged family business on his mother's advice to selling at an incredibly high multiple to a PE-backed acquirer, Nate Collins shares how he built a transferable licensing company, what the post-exit "liminal period" really looks like, and why personal well-being is a greater …
Episode 405: Reducing Lifetime Tax Drag for Business Owners with Omar Morillo
When Omar Morillo talks about wealth management for entrepreneurs, he focuses on one core idea: reducing lifetime tax drag across income, investments, business operations, and eventual liquidity events. The earlier owners start planning, the more options they have.
In this episode of the DealQuest…
38 – Why Your Childhood "Programs" Are Tanking Your Startup
Your host Alex Shevelenko welcomes Dave Hersh, the visionary founder of Jive Software, an active investor, and the author of the upcoming book The Eros Advantage. In this episode, Dave shares his deep-dive into why human connection and psychological awareness are the ultimate competitive advantages…
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