From Start-Up to Grown-Up #105 Legendary Kleiner Perkins Investor Shares the 3 “Whys” Every Founder Must Answer (Encore)
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Nov 18, 2025 
Randy Komisar, a seasoned entrepreneur and investor at Kleiner Perkins, shares invaluable insights from his impressive career. He recounts transforming a challenging interview with Neil Young into a success by ditching the script. Randy also discusses the influence of his gambler father on his ability to read people, and highlights crucial signs to detect lies in entrepreneurs. He emphasizes the importance of self-awareness and shares the three ‘whys’ every founder must answer: why this, why you, and why now. A must-listen for aspiring founders!
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From Scripted Failure To Live Rescue
- Randy nearly bombed an on-stage interview with Neil Young when the scripted questions failed. He threw away the script, grabbed beers, sat closer, and followed where Neil lit up to salvage a brilliant conversation.
Lessons From A Gambler Father
- Randy learned people-reading from watching his father, a professional gambler and salesman, at casino tables and morning debriefs. Those experiences trained him to spot weaknesses, bluffs, and consistent tells in conversations.
Spotting Lying vs. Exaggeration
- Randy distinguished between exaggeration and outright lying in founders and used people-reading to spot deception. He occasionally flagged liars early and felt vindicated when those investments failed.
