Episode 162: The Startup Whisperer: Why Founder Success Doesn't Guarantee Investor Success with Andrew Ackerman
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Episode 162: The Startup Whisperer: Why Founder Success Doesn't Guarantee Investor Success with Andrew Ackerman
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In this episode of the Throttle Up Leadership Podcast, Dr. John Dentico interviews Andrew Ackerman.
Andrew Ackerman isn't just another VC with opinions; he's the startup whisperer who's lived every role in the ecosystem. This serial entrepreneur turned angel investor turned venture capitalist has invested in 70+ startups, mentored hundreds of founders, and built innovation programs that deliver. As strategic advisor and head of Reach Labs for Second Century Ventures, he brings battle-tested perspective to property tech and construction tech, though his hard-earned lesson surprises: being a successful founder doesn't automatically make you good at recognizing success in others at scale.
Born in Israel to American parents, raised around New York City, Andrew credits his entrepreneurial grandfather, who died when Andrew was twelve, as his biggest influence. The conversation cuts through startup mythology with surgical precision, tackling founder archetypes, pattern recognition failures, and AI hype versus reality. Andrew's hope? That we find the right balance between proven methods and shiny new tools, building wisdom while maintaining optionality. For his three daughters facing 40-year career horizons in radically uncertain times, he champions transferable talents over rigid job titles; advice that resonates across generations.
Born in Israel, Raised in New York - 02:13
Grandfather's Entrepreneurial Influence - 02:46
Every Hat in the Startup World - 03:27
Founder to Investor Transition - 03:42
Pattern Recognition Pitfalls - 04:03
The Entrepreneur's Odyssey Book - 08:15
Founder Archetypes and Success - 14:30
Property Tech and Construction Tech - 19:45
AI Hype Versus Reality - 35:20
Shiny Objects Versus Accumulated Wisdom - 46:47
Career Optionality for Next Generation - 47:14
Finding Balance in Uncertainty - 48:02
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