How Real Leaders Show Up Under Pressure | Inside Kent Richeson’s Pitch Arena cover art

How Real Leaders Show Up Under Pressure | Inside Kent Richeson’s Pitch Arena

How Real Leaders Show Up Under Pressure | Inside Kent Richeson’s Pitch Arena

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 Michelle Terpstra sits down with Kent Richeson, creator of Sh*t Pitch and the upcoming TV show The Cut, to unpack what really matters when money, reputation, and momentum are on the line. Forget perfect pitch decks and rehearsed demos—this conversation digs into why behavior under pressure reveals far more than polished slides ever could. Kent explains how Sh*t Pitch was designed to expose the “who” behind the business, not just the “what,” and why trust, coachability, and emotional intelligence consistently outperform flash and bravado.

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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