Episode 396: Do You Actually Want to Be a Deal Maker with Corey Kupfer

Episode 396: Do You Actually Want to Be a Deal Maker with Corey Kupfer

March 25, 2026 · 24 min · Season 1

About this episode

Corey Kupfer discusses the complexities of deal making and the importance of self-assessment for entrepreneurs.

From year-end deal crunches to honest conversations about risk tolerance and self-knowledge, Corey Kupfer makes the candid case for why deal making may not be for every entrepreneur, and what it actually takes if you decide it is. In this remastered DealQuest solocast, host Corey Kupfer draws from his own experience managing multiple year-end closings while stretched thin to walk through three reasons why deals may not align with every business leader's goals or temperament, and how the flip side of each reason reveals the roadmap for those who do want to pursue deals. WHAT YOU'LL LEARN In this episode, you'll discover why even experienced deal teams face periods of all-encompassing intensity, how risk tolerance shapes whether and how you pursue deals, and why some entrepreneurs are better served by doubling down on organic growth. Corey explains how the CPR tool from his Authentic Negotiating book can help you assess whether deals belong in your growth strategy, and why the distinction between born deal makers and situational deal makers matters. THE HONEST CASE FOR SELF-ASSESSMENT Corey acknowledges the counterintuitive nature of a deal-making advocate telling listeners they…

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