400 Episodes, One Mission: The Story Behind DealQuest with Corey Kupfer

400 Episodes, One Mission: The Story Behind DealQuest with Corey Kupfer

April 22, 2026 · 41 min · Season 1

About this episode

Corey Kupfer reflects on the journey of the DealQuest Podcast, discussing its origins, growth, and insights into podcasting for business.

Nearly 8 years, 400 episodes, and close to 30,000 monthly listens: Corey Kupfer shares how the DealQuest Podcast started as a solution to a real business problem, what the guest relationship strategy actually produces for a professional services firm, and why most podcasters quit before the compounding effect kicks in. In this milestone episode of the DealQuest Podcast, host Corey Kupfer hands the mic to his law firm partner Brian Meegan for a candid look inside nearly eight years of podcasting. Corey is an expert strategist, negotiator, and dealmaker with more than 35 years of professional deal-making experience, and the creator of the DealQuest Podcast. Brian Meegan is Corey's partner at Kupfer Law and a longtime member of Entrepreneurs' Organization, where the two originally met. WHAT YOU'LL LEARN: How a frustration with staying connected at scale led to a podcast now generating close to 30,000 listens per month, why the guest relationship is more valuable than the listener base for a professional services business, what "pod fade" is and why more than 85% of podcasts never reach 15 episodes, and the distinction between born dealmakers and situational dealmakers and why it…

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