20VC: The AI Boom Will Create Enormous Roadkill: Who Wins & Loses | Why Founders Should Never Take Multi-Stage Money at Seed | Why Triple, Triple, Double, Double is Good Enough

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I Have Never Seen Secondary Markets This Liquid

At 56:30 · chapter starts 46:39

Harry raises a pointed question about founder loyalty and focus: today's founders often have angel portfolios as large as small VC funds, run side projects, and leave companies in 12–18 months. Is the breed changing? Frankel acknowledges the evidence at the margins — he's been dazzled by founder brand power that didn't translate to staying power — but argues the vast minority of founders actually abandon ship. His most interesting observation: second-time founders who had a life-changing but not enormous first outcome are often the best bets. They're hungry, they've learned lessons, they have one or two loyal team members ready to follow them, and they're in a hurry. By contrast, founders who had genuinely great outcomes and 'go again' often get bored when the second company isn't big enough fast enough.