How Real Leaders Show Up Under Pressure | Inside Kent Richeson’s Pitch Arena
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The discussion draws powerful parallels between fundraising and sales, including the contrarian truth that introverts often outperform extroverts when it comes to conversion, trust-building, and long-term success. Michelle and Kent also explore the shifting role of AI in pitching and selling, why founders are overusing AI as a buzzword, and where human connection still wins, especially in high-stakes decisions. From category-defining ideas to pressure-testing leadership before commitment, this episode reframes how founders, investors, and sales leaders should evaluate talent, traction, and potential.
Chapters
[Start] Why Pressure Reveals the Truth: How Sh*t Pitch was designed to expose founder behavior, not just business ideas.
02:00 The Sh*t Pitch Format Explained: Impromptu “bad idea” pitches, real business decks, and why investors care more about trust than polish.
09:00 Introverts Win More Than You Think: Why listening, empathy, and sincerity outperform charisma in both sales and fundraising.
14:30 AI, Sales, and the Boomerang Effect: Where AI supports selling, and why human closers still matter in high-stakes decisions.
22:00 From Sh*t Pitch to The Cut: The evolution into a competitive TV show, investor-backed funding, and pressure-testing founders at scale.
Links & Resources
The Cut
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