WillPower Podcast

What do commanding a nuclear submarine and building lasting wealth have in common? More than you'd think. In this episode, Rick and I sit down with Gary Pinkerton — a Navy veteran who spent over 30 years as a nuclear submarine officer, including commanding the USS TUCSON, before pivoting into a second career as a Wealth Strategist. Gary opens up about the wake-up call that changed his financial tr...

What if you could buy and sell real estate without ever walking into a bank? Chris Prefontaine, Chairman and Founder of Smart Real Estate Coach® and 4x best-selling author, has built an entire movement around exactly that. A 3-time Inc. 5000 honoree and former Forbes Business Council Member, Chris has guided his community to hundreds of successful creative finance transactions across North America...

What happens when a technology leader who's helped scale a therapy organization from 70 to 180 clinicians decides to build the tool he always wished existed? You get Ambiki — and you get Kevin Dias. Kevin is the founder of Ambiki, an EMR and practice management platform built specifically for pediatric speech, occupational, and physical therapy practices. Before launching Ambiki, Kevin served...

What does it take for a high-achieving executive to step off the traditional path, relocate to Spain, and build a life of true freedom — without sacrificing success? Billy Keels has done exactly that, and he's made it his mission to help other ambitious C-Level leaders do the same. Billy is a national bestselling author, the host of the top 1% globally ranked podcast Going Long , and an execut...

Jon Ostenson has seen both sides of the business world — 15 years climbing the corporate ladder, including a VP of Sales role at Carter's overseeing $350M in revenue, and then a full pivot into franchising. Now, as Founder of FranBridge Consulting and a top 1% franchise consultant in the US, Jon spends 90% of his time helping everyday people discover the freedom and wealth that come with ownin...

What do running ultramarathons and scaling a $283 million real estate portfolio have in common? Everything — if you're Jason Yarusi. This week, host Rick Segal joins the show as we sit down with the founder of Yarusi Holdings, a man who has built and exited a construction company, restaurants, a brewery, and now over 2,500 apartment units since 2017. Jason doesn't just talk about disciplin...

Ken Gee — Founder and Managing Member of KRI Partners — traces a remarkable career journey that took him from running Cessna flight schools in Northeast Ohio to closing over $2 billion in real estate transactions. With stops at a regional bank, Deloitte's M&A practice, and the front lines of multifamily investing, Ken breaks down what 26+ years in the trenches has taught him about capital,...

Welcome back to the show. Today's guest is someone who has spent decades making an unforgettable mark on both the big screen and daytime television. You know him as the intimidating Mike Barnes — the villain who squared off against Daniel LaRusso in Karate Kid Part III — a role he beat out over 2,000 other hopefuls to land. He then reprised that iconic character in Netflix's smash hit Cobr...

In this episode, I sit down with Joe Downs, Co-Founder and CEO of the Belrose Group, a company focused on acquiring and operating self-storage facilities across the country. With over 20 facilities and $50M+ in assets under management, Joe has built a scalable model in one of the most overlooked sectors of commercial real estate. We break down how he got started, why self-storage continues to outp...

In this episode of the WillPower Podcast, Rick Segal and Will Holdren sit down with Eric Wiklendt, Partner and Managing Director at Speyside Equity, to break down what private equity actually looks like behind the scenes. With over 15 years at Speyside, Eric has been directly involved in sourcing, operating, and exiting investments across manufacturing businesses. Before that, he served as CEO of...

In this episode of the WillPower Podcast, we are joined by Todd Dexheimer, Principal at Endurus Capital and VitaCare Living, to break down how he built a $550M+ real estate portfolio across multifamily, senior living, and commercial assets. Todd started investing during one of the most uncertain times in modern history—the 2008 financial crisis—and has since scaled into large institutional-level d...

In this episode of the WillPower Podcast, Will interviews Brian Murray—a multifamily investor with GP equity in over 15,000 units and co-founder of Open Door Capital, which has grown to over $1B in AUM. Brian shares how his journey started with building Washington Street Properties into an Inc. 500 company, and how that led him into the world of multifamily investing. But beyond the numbers, this...

In this episode of the WillPower Podcast, Will is joined by co-host Rick Segal and special guest Matt Picheny—a real estate investor, operator, international speaker, and author with over 15 years of experience and 12,000+ apartment units acquired nationwide. Matt breaks down what it really takes to syndicate real estate deals the right way. From structuring deals and raising capital to avoiding c...

In this episode of the WillPower Podcast, Will sits down with Giuseppe Grammatico, also known as “GG the Franchise Guy” — a franchise veteran, coach, author, and speaker who has helped countless individuals break out of the traditional 9–5 and step into business ownership. GG shares how franchising can be one of the most overlooked paths to building wealth and achieving the American Dream. We dive...

In this episode of The Willpower Podcast, host Will Holdren sits down with real estate investor and technologist Neal Bawa, widely known in the industry as the “Mad Scientist of Multifamily.” Neal is the founder and CEO of Grocapitus Investments, a data-driven real estate investment firm with a portfolio spanning thousands of units and hundreds of millions of dollars in assets across the United St...

What does it really take to scale from your first deal to over 1,500 units? In this powerhouse episode of the WillPower Podcast, I sit down with Rick Segal and John Casmon, host of the Casmon Capital Podcast and founder of Casmon Capital Group. John has built a multifamily portfolio exceeding 1,500 units and now helps busy professionals break into commercial real estate the right way — with strate...

What does it really take to build a business that creates true freedom? In this episode of the WillPower Podcast, I sit down with John Lee Dumas, founder and host of Entrepreneurs on Fire , one of the most successful business podcasts of all time with over 4,000 episodes and millions of listeners worldwide. Instead of covering the same questions he’s answered hundreds of times, we dive deeper into...

How do you go from the classroom to building a 7-figure consulting business? In this episode of the WillPower Podcast, I sit down with Dr. Erica Jordan Thomas, CEO of 7 Figure Educator, a business development company that is shifting power in education by helping educators build scalable, profitable consulting businesses. Dr. Erica is on a mission to equip teachers, administrators, and education l...

In this episode of the Will Power Podcast, Will Holdren sits down with real estate investor, certified money coach, entrepreneur, and podcast host Gino Barbaro . Gino has scaled his multifamily portfolio to over 1,900 units and more than $450 million in assets under management — but his mission goes far beyond real estate. Through Barbaro 360, he is focused on empowering families to build lasting...

In this episode of The Willpower Podcast, host Will Holdren sits down with entrepreneur and investor Damion Lupo for a wide-ranging conversation on business, investing, and building real wealth. Damion is the Chairman and Chief Investment Officer of FrameTech, a construction technology company focused on transforming the future of framing and the way buildings are constructed. Over the course of h...

In this powerful episode of The Willpower Podcast, host Will Holdren is joined by co-host Rick Siegel and special guest Ryan Dewey Smith, founder and CEO of Inperium, Inc.. Ryan leads a billion-dollar nonprofit operating across 20 states, focused on mental health services and helping organizations scale while preserving their core mission and values. Prior to founding Inperium, Ryan served as CEO...

In this episode of The Willpower Podcast, we sit down with Jeff Hoffman, co-founder of Priceline / Booking.com, to break down what it really takes to build, scale, and lead world-class companies. Jeff shares behind-the-scenes lessons from building Priceline into a global travel powerhouse, along with the timeless principles he’s learned about entrepreneurship, leadership, company culture, and serv...

AI is moving faster than most entrepreneurs can even comprehend… and today’s conversation proves it. In this episode of The Willpower Podcast, I’m joined by returning guest Rick Segal and special guest Dirk Liebich — an engineer born and raised in Germany who started his career programming microchips as an electrical engineer before diving into the world of advanced AI development. Dirk is now bui...

In this episode of The Willpower Podcast, I’m joined by Tiffanie Janowitz, CEO of Limitless Society, where she helps entrepreneurs create the personal and business infrastructure needed to scale success without sacrificing their peace. We dive deep into mindset mastery, habit architecture, and the systems required to become the kind of entrepreneur who can sustain momentum—without burnout. If you’...

In this episode of The Willpower Podcast, I sit down with Joey Jenkins, the CEO of Vooks — an ad-free, kid-safe streaming platform that turns children’s books into animated read-aloud story experiences designed to make screen time more meaningful and educational. We talk about what it really takes to build a mission-driven company, how Vooks is helping shape early literacy through storytelling, an...