The Dwayne Kerrigan Podcast
Dwayne Kerrigan, a veteran of over 35 years in the business world with nearly 30 ventures across 12 industries, hosts a podcast focused on unsung yet successful entrepreneurs. Together, they explore personal journeys, insights, and strategies.
Recent Episodes
148
July 15, 2026
148: Brian Will: Don't Sell to Private Equity Without This
Most business owners think getting a call from private equity is the finish line. Brian Will says that's exactly when you're most at risk. In Part 2, Brian delivers the frameworks that took him three exits and decades of hard lessons to build — from the five keys to success (which are also the five keys to failure) to what private equity firms will do to your earn-out if you're not paying attention. In this episode: The five keys to success — and why every single one is also a key to failure W
147
July 8, 2026
147: From Dropout to Multimillionaire: Brian Will's Success Formula
Brian Will has owned 10 companies across five industries, made three exits worth over $500 million, and written four books — including two Wall Street Journal bestsellers. None of it was handed to him and the odds were very much against him. In this conversation with Dwayne Kerrigan, Brian unpacks the frameworks behind his success: the personal filter, the success ladder, and the $80 million decision he almost said no to. In this episode: The "I'm in" moment: Brian's business partner Steve aske
146
July 1, 2026
146: Why AI Empowers Entrepreneurs More Than Anyone with Sean Barry
Sean Barry's team used to spend six months building a feature. Now they build it in two to three weeks. In Part 2, Sean and Dwayne move from the AI transformation inside LeanScaper to the bigger picture: what the software industry looks like in twelve months, why autonomous cars and AI adoption are fundamentally different problems, and what it actually means to participate in this change rather than spectate. In this episode: Why the software industry is facing a potential 50-80% company turn
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