400 Episodes, One Mission: The Story Behind DealQuest

Four hundred episodes in. That's not a milestone I take lightly, and in this special episode of the DealQuest Podcast, I'm turning the mic over to my law firm partner Brian Meegan to ask me the questions. It was actually Jennifer on our team who suggested the idea, and I have to say, being on the receiving end of an interview is a very different experience. What came out of it surprised even me.

This conversation covers the full arc of how DealQuest came to be, from a real business frustration about staying connected at scale, to a chance encounter with the story behind Gimlet Media, to nearly a decade of learning what a podcast can and cannot do for a professional services business. Whether you're a business owner considering whether a podcast makes sense for your growth strategy, or a dealmaker curious about the philosophy behind the show, this episode pulls back the curtain in a way we've never quite done before.

WHY THE PODCAST STARTED (AND WHAT IT WAS REALLY SOLVING)

The original problem wasn't about content. It was about scale. When my law firm was smaller, I could stay genuinely connected with clients, referral sources, and industry partners. But as we grew, that kind of one-to-one relationship maintenance became impossible. I was frustrated watching the quality of those connections thin out as the volume of relationships increased.

That frustration led me to start studying a concept called authority marketing, which is very different from being a social media influencer. The idea was to stay top of mind at scale in a way that actually reflected our quality and our values. The snail mail newsletters lawyers were sending at the time weren't it. LinkedIn in those early days was essentially a job-seeking platform. There had to be a better way.

THE MOMENT I KNEW A PODCAST MADE SENSE

The real spark came at an Entrepreneurs' Organization event in New York. Alex Bloomberg, the founder of what became Gimlet Media, came to speak. He had just left NPR to launch a podcast company, and the podcast itself was called Startup, which was a podcast about him starting a podcast company. Completely meta, and completely fascinating.

He talked about naming the company, getting his wife to laugh at his early ideas, and a disastrous pitch to a major VC. I was completely hooked. Around the same time, I was learning that podcasting was the way to build exposure around a book, not bookstore signings. So I had come to podcasting first as a guest, promoting my Authentic Negotiating book, and then started thinking seriously about hosting my own.

BUILDING THE THESIS FOR DEALQUEST

I studied models the way I study anything, by talking to people who had already done it. One of the first things I learned was the concept of "pod fate," which is that more than 85% of podcasts don't make it past 15 episodes. People start, life gets in the way, the numbers feel discouraging, and they stop. That was never going to be me. My view was either I commit to doing this for the long haul, or I don't start.

The second question was what the show would actually be about. I knew I didn't want a general entrepreneurship podcast because there are already great ones. I also didn't want something too narrow, like a podcast focused only on M&A or only on capital raising. What I kept coming back to was deal-driven growth as an underutilized concept. Most entrepreneurs spend all their time on organic growth, which they should, but there's an entire world of deals available to them: M&A, joint ventures, strategic alliances, licensing, franchising, real estate, affiliate deals, distribution deals. I always felt that was a blindspot. That became the thesis.

FUELING DEALS BECOMES DEALQUEST

The show launched under the name Fueling Deals, and for the first year and a half, that's what it was called. The rebrand to DealQuest came about a year and a quarter in, when we brought on a production team that did some research around branding and format. They also sharpened the format I still use today: a defined open, a defined close, and everything in between is open conversation with no pre-prepared questions.

Getting the right team around the show took a while. I went through three podcast production companies before finding the right fit. That was also when the rebrand happened. Getting there took time and required making some hard decisions about what wasn't working.

WHAT GROWTH ACTUALLY LOOKED LIKE

When I started, I was calling friends, clients, and EO buddies asking them to be guests. A typical episode might get 60 or 80 listens. Now we're getting close to 30,000 listens a month and managing a constant inbound stream of guest requests that we have to vet carefully.

But the first signal that the podcast was working had nothing to do with listener numbers. It came from conversations. Clients I hadn't spoken to in a while would mention a specific episode. A referral source would bring up something they'd seen on LinkedIn, which was mostly content we'd repurposed from the show. People I had assumed were ignoring everything I posted would tell me they'd been listening for months. That's when I understood the lurker phenomenon: most people are reading and listening without ever liking or commenting. If you're measuring the health of your content by public engagement, you're undercounting your actual reach significantly.

THE THREE WAYS THE PODCAST CREATES REAL VALUE

Over time, I've broken down the business value of doing the podcast into three distinct areas, and the order matters.

The first is staying top of mind with your existing network. When the content is consistent and relevant, your audience keeps you present in their thinking even when there's no active reason to be in touch.

The second is credibility and searchability. Almost anyone referred to me will search my name before making contact. When they find 400 episodes, a published book, years of consistent content, and rankings in specific search areas like investment advisor attorney or M&A counsel for mid-market companies, that search experience does work on your behalf. We've gotten meaningful clients who found us through Google alone, looking for highly specific expertise.

The third, and most underestimated, is the guest relationship. Of the 400 episodes, roughly 300 have been interviews with outside guests. That's 300 relationships, some existing and many new. And because the first thing I'm doing in that relationship is giving them exposure to a meaningful audience, the dynamic starts from a place of value creation. People who give first and genuinely serve rarely have to ask for much later. I've gotten more direct business and referrals from guests than from the broader listener base, even though the listener base is the larger number.

THE EPISODES THAT STAYED WITH ME

Brian asked me to name the most surprising or memorable moments, and a few came to mind immediately.

Brian Smith, the founder of Ugg, was a guest in the first 20 episodes. He's a chartered accountant from Australia who came to the U.S. as a surfer with sheepskin boots in his car trunk, and ended up building one of the most recognizable footwear brands in the world. The deal stories behind that company were as compelling as the entrepreneurial ones, including losing control of the company at one point and getting it back.

David Bacon, an eight-time New York Times bestselling author and a friend and client, came on and opened my eyes to a deal model most people don't think about. Beyond getting a book deal and selling copies, he had built brand partnerships and licensing arrangements that generated real business revenue from the books. That conversation illustrates exactly the kind of deal angle that the podcast was designed to surface.

Damon Gershon shared his story from 9/11 and how he built a workforce staffing operation, including a strategy of hiring up labor before having the contracts in place, which is an unusual and high-stakes approach. But what really stuck was the industry association structure he and his team built, where regional companies co-owned an entity together with standardized contracts and referral arrangements, allowing them to compete against national players. That's the kind of creative affiliation deal that most people don't realize is available to them.

Dave Hirsch, who has spoken at the Deal Exchange Conference, shared his journey through post-founder depression after a successful exit. He talked about what it actually felt like, not as a setup for an eventual triumphant story, but as a real and sustained experience. He now works with entrepreneurs to help them prepare for exits in ways that don't leave them lost on the other side. If you want to go deeper on that topic, that conversation is worth finding in the archive.

BORN DEALMAKERS AND SITUATIONAL DEALMAKERS

One of the things I've gotten clearer on over nearly 400 episodes of interviews is the parallel between entrepreneurs and dealmakers. We talk a lot about born entrepreneurs versus people who shouldn't be entrepreneurs, but we rarely make the same distinction for dealmaking. There are people for whom deals are instinctive, and there are what I'd call situational dealmakers, people who didn't start as deal-oriented thinkers but learned it out of necessity or opportunity.

What's encouraging about recognizing that distinction is that it opens the door. When people treat dealmaking as a natural talent exclusive to a certain personality type, they opt out before they even try. But there are deal structures where risk is manageable and strategy is learnable. People across a wide range of personalities and risk tolerances can and do do deals. I've built an entire talk around this idea called There's a Deal for That, the premise being that almost any business challenge, frustration, or opportunity has a potential deal solution worth at least considering.

WHAT LEARNING ACROSS INDUSTRIES DOES FOR DEALMAKING

One of the things I love most about the podcast is the exposure it gives me to different industries and different ways of building and growing companies. I've talked to people working in industries I would never otherwise encounter, and more than once, something I heard in those conversations has applied directly to what we do in our practice.

When you spend all your time inside one industry, you miss the innovations happening in others. Some of the most interesting things I've seen in deal structures came from people describing what's normal in their space, not knowing that nobody in a different industry had thought to try it. That cross-industry perspective is something I try to maintain deliberately in the guest mix.

This connects to what I loved about the podcast Acquired, which does deep dives on individual companies and industries in three to four hour episodes once a month. Their episodes on Trader Joe's, the NFL, and Google illustrate what becomes possible when you really take the time to understand how a business or industry actually works.

THE ADVICE I'D GIVE ANYONE CONSIDERING A PODCAST

The landscape has shifted significantly since I started in 2018. There's no shortage of voices telling you that you need to be everywhere, posting on every platform, launching every format. I disagree.

I focus on LinkedIn and YouTube. I stopped using Instagram and Facebook years ago. I've been approached to write weekly columns and have turned them down, not because writing is beneath me, but because generating original written content on a consistent schedule would be a serious drain on my time and energy. The podcast works for me because it genuinely energizes me. I look forward to recording episodes. People comment on the energy in the conversations, and that energy comes from the fact that I'm doing something I love.

Pick the medium where you show up best and that you're genuinely excited to sustain. Commit to it over the long term, because authority is built slowly through consistency. Don't do 20 things at a moderate level. Find the one or two things that you're both good at and passionate about, and go deep on those.

LOOKING TOWARD THE NEXT 400

What's different after 400 episodes is mostly a matter of infrastructure and selectivity. We vet guests now. We can be intentional about variety, making sure we're not concentrating too heavily in any single deal type for too long. When I notice we haven't covered family business partnerships or a particular niche in a while, we go looking.

The deal landscape itself keeps evolving, which keeps the show fresh. AI's impact on deal flow, shifting dynamics in M&A markets, new structures emerging in various industries. There will never be a shortage of material. And there are topics we haven't touched enough yet, including the post-exit emotional experience and the psychological dimensions of dealmaking, which I think get far less attention than they deserve.

I'm grateful to everyone who has been listening, sharing, and sending great guests our way. This show exists because of that community.

Listen to the full episode of DealQuest Podcast Episode 400 with Corey Kupfer

FOR MORE ON BRIAN MEEGAN
LinkedIn: https://www.linkedin.com/in/brianmeegan/
Company: https://www.kupferlaw.com

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!