400 Episodes, One Mission: The Story Behind DealQuest with Corey Kupfer
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 fate" is and why more than 85% of podcasts never reach 15 episodes, and the distinction between born dealmakers and situational dealmakers and why it matters for entrepreneurs who think deals aren't for them.
ORIGIN STORY: The podcast started as a business problem. As the law firm grew, staying genuinely connected with clients, referral sources, and industry partners at scale became impossible. Authority marketing offered a path. An Entrepreneurs' Organization event in New York, where Gimlet Media founder Alex Bloomberg spoke candidly about starting a podcast company, made the medium click. The show launched in 2018 as Fueling Deals, rebranded to DealQuest about a year and a quarter in, and settled into the format it holds today: a defined open, a defined close, and everything in between is open conversation with no pre-prepared questions.
KEY INSIGHTS: The three-part value model for a professional services podcast covers staying top of mind with your existing network, credibility and searchability when a prospect googles you, and actual search-driven client acquisition. All three have produced meaningful results for the DealQuest practice.
The guest relationship is the most underestimated asset. Of approximately 300 guest interview episodes, the direct business and referrals from those guest relationships have outweighed what came from the broader listener base. The relationship starts from a place of value creation because the first thing Corey does is give guests access to a meaningful audience.
Pod fate is real. More than 85% of podcasts don't reach 15 episodes. Corey's posture from the start was either commit to hundreds of episodes or don't start. Pick a medium you're genuinely energized by, because the energy in the conversation is not replicable with a format you find grinding.
Born dealmakers and situational dealmakers are both real. People who treat dealmaking as an exclusive talent tend to opt out before they try. Deals can be learned, and there are structures where risk is easily managed. That's the premise behind Corey's talk called There's a Deal for That: any business challenge or opportunity has a potential deal solution worth at least considering.
Perfect for entrepreneurs and business owners considering whether a podcast makes sense for their business, professionals thinking about authority marketing strategy, and dealmakers curious about what nearly 400 conversations about deals has taught someone with 35 years of deal-making experience.
FOR MORE ON THIS EPISODE:
https://www.coreykupfer.com/blog/episode400
FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/
Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.
Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!
Episode Highlights with Timestamps
[00:03:35] - The origin: Authority marketing, the scale problem, and why a podcast
[00:06:45] - The Gimlet Media moment: How Alex Bloomberg's story made podcasting click
[00:11:51] - Fueling Deals becomes DealQuest: The rebrand and format evolution
[00:14:50] - Growth from 60-80 listens to close to 30,000 per month
[00:18:26] - The lurker phenomenon: Why public engagement undercounts your real reach
[00:20:28] - The three-part value model for a professional services podcast
[00:23:06] - The guest strategy: Why guest relationships outperform listener reach
[00:28:50] - Memorable guests and the deal stories that stuck
[00:38:31] - Born dealmakers vs. situational dealmakers
[00:44:05] - Final advice: Pick your medium, go deep, and commit for the long term
Related Episodes
Episode 327 - Solocast 71: Authority Marketing and How a Podcast Drives Deal-Driven Growth
Episode 331 - Solocast 72: Deal-Driven Growth Strategy for Business Owners
Episode 339 - Solocast 74: Equitizing Key Employees and Succession Planning Strategies
Episode 351 - Solocast 77: Deal Structures and Strategic Growth Planning
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