Ditch Digger CEO with Gary Rabine

Hosted by Gary Rabine

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135

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Jun 2026

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About the show

Ditch Digger CEO is a podcast that will feed and grow your hunger for entrepreneurship. This show chronicles those who have built their business from nothing to million or even billion dollar enterprises. Often with only grit and work ethic to rely on. Gary Rabine is a serial entrepreneur who has started 25 companies over the past 20 years. For business inquiries email PodcastDDCEO@gmail.com

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60 recent

June 8, 2026Episode 1311 hr 4 min

#131 How Great Entrepreneurs Find Hidden Markets w/ John Berger, CEO at Otovo

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/John Berger is a serial entrepreneur, energy innovator, and founder of Otovo, an AI-enabled energy services company focused on maintaining and optimizing the rapidly growing ecosystem of behind-the-meter power assets. With operations spanning North America and Europe, Attovo services generators, solar systems, batteries, EV chargers, and other distributed energy technologies designed to keep critical power infrastructure running when customers need it most.In this conversation with Gary Rabine, John shares lessons from building businesses in rapidly evolving markets, why service businesses often create more value than installation businesses, and how AI, batteries, and distributed energy systems are reshaping the future of power.In this episode, Gary and John discuss:Why some of the biggest business opportunities come from fragmented industriesThe evolution of residential solar, batteries, and distributed energyHow service businesses create long-term enterprise valueWhat entrepreneurs can learn from the energy industry's transformationWebsite: https://www.otovo.com/ LinkedIn: https://www.linkedin.com/in/john-berger-61042724/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

May 22, 2026Episode 1301 hr 22 min

#130 How to Build Trust in an AI-Driven World w/ Beth Hollenberg, Chief Executive Officer, Everspring

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Beth Hollenberg is the CEO and Co-Founder of Everspring, a leading education technology and services company helping universities adapt and thrive in an era of AI, digital transformation, and changing student expectations. With more than 20 years of experience across education, technology, and public policy, Beth has become one of the most respected voices in higher education innovation and online learning strategy. In this conversation with Gary Rabine, Beth shares her perspective on the future of higher education, the rise of AI-powered learning, and why empathy, adaptability, and human connection are becoming the most valuable leadership skills in business today.In this episode, Gary and Beth discuss:Why higher education is undergoing massive transformationThe difference between real online learning and “Zoom school”How AI will reshape education and business leadershipWhy students no longer think in terms of “online vs. on-campus”Website: http://www.everspringpartners.com/ LinkedIn: https://www.linkedin.com/in/bethhollenberg/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

March 17, 2026Episode 1291 hr 9 min

#129 Culture Isn’t What You Put on the Wall — It’s What You Do Every Day w/ Dean Vicha, President at NationaLease

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Dean Vicha is a veteran transportation industry leader and CEO of National Lease, one of the largest truck leasing and fleet management organizations in North America. Known for his emphasis on trust-driven leadership and relationship-based business, Dean has spent decades building a company culture rooted in accountability, mentorship, and service. A respected voice among entrepreneurs and business leaders, he has helped guide organizations through economic cycles, industry disruption, and technological transformation while maintaining a strong commitment to people-first leadership.In this conversation with Gary Rabine, Dean shares lessons from his journey in leadership, including the mentors who shaped him, the power of transferable trust in business, and how entrepreneurs can navigate massive changes in technology and global markets.In this episode, Gary and Dean discuss:Why culture is defined by behavior — not the values written on a wallThe power of transferable trust in business relationshipsHow mentors and tough coaches shape great leadersThe three traits every entrepreneur must develop: persistence, responsibility, and self-confidenceWebsite: http://www.nationalease.com/LinkedIn: https://www.linkedin.com/in/dean-vicha-8a414822/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

December 1, 2025Episode 1281 hr 19 min

DDC #128 The Discipline of Moving Fast Without Breaking What Matters w/ Biju Kulathakal, Founder and CEO, LightSpeed | Halo Investing

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Biju Kulathakal (@BijuKulathakal) is a serial entrepreneur, technologist, and investor whose career spans fintech, advanced automation, and large-scale manufacturing. He is the Founder and CEO of Lightspeed, a robotics and AI-driven construction company aiming to transform how homes are built using high-precision automation and modular production. Prior to Lightspeed, Biju co-founded Halo Investing, one of the most acclaimed platforms in protective investing, and helped launch the company that would become Redbox. With deep roots across multiple technology ecosystems — and a degree in aerospace engineering — Biju brings a rare combination of technical rigor and entrepreneurial boldness.In this conversation with Gary Rabine, Biju breaks down what it takes to build across industries, why construction is overdue for reinvention, and how founders can blend imagination with precision to solve massive global problems.In this episode, Gary and Biju discuss:The founder mindset required to reinvent multiple industriesLessons learned from co-founding Halo and scaling modern wealth-techHow discipline, precision, and vision guide Biju’s approach to innovationThe mission behind the Vidya Foundation and why education unlocks opportunityLinkedIn: https://www.linkedin.com/in/biju-kulathakal-b5b80b1/ Website:LightSpeed - https://www.bylightspeed.com/ Halo Investing - https://haloinvesting.com/ Twitter: https://x.com/bijugk Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

November 24, 2025Episode 1271 hr 6 min

#127 Converting Your Business From a Vitamin to A Painkiller w/ Tim Stojka, CEO, Nexus3 Capital

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Tim Stojka (@TimStojka) is a serial entrepreneur, angel investor, and board leader who has spent three decades building technology companies from the ground up. From programming an Apple II in his parents’ basement to founding three major SaaS firms — including one that raised $40 million during the dot-com boom — Tim has lived the full arc of innovation, hype cycles, and hard-earned product-market fit. His latest chapter: applying AI and language models to reshape enterprise software through his new venture, Nexus Three Capital.In this conversation with Gary Rabine, Tim breaks down the real mechanics behind creating, scaling, and surviving as a founder — from vitamins vs. painkillers, to why most tech is overhyped early and under-hyped later, to how AI will transform the next decade of entrepreneurship.In this episode, Gary and Tim discuss:Product-Market Fit: why vitamins lose money and painkillers scaleHow a failed stuffed-animal startup taught him everything about inventory and demandThe dot-com rollercoaster: raising $40M, preparing for a $1B IPO, then crashing to zeroWhy founders should go slow now to go fast laterLinkedIn: https://www.linkedin.com/in/timjstojka/ Website: https://nexus3capital.com/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

October 13, 2025Episode 1261 hr 41 min

#126 The Three Prayers That Built a Champion w/ Don Beebe, Head Football Coach, Aurora University, Former NFL Player, Founder, House of Speed

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Don Beebe (@DonBeebeNFL) is a former NFL wide receiver, Super Bowl champion, and one of the fastest players in league history. From hanging aluminum siding to breaking 40-yard dash records in jean shorts, Don’s unlikely rise from small-town Illinois to six Super Bowls is a masterclass in perseverance, faith, and purpose. In this conversation with Gary Rabine, Don shares how his journey—from being overlooked to outworking everyone—reveals timeless lessons for leaders, founders, and anyone striving to build something that lasts.In this episode, Gary and Don discuss:How to turn adversity and setbacks into fuel for growthWhy faith, discipline, and character outlast talent and opportunityBuilding a winning culture: from 17 kids in a gym to state championsThe leadership principle behind the legendary “Leon Lett Play”How to instill humility, passion, and belief in your teamLinkedIn: https://www.linkedin.com/in/donbeebe82/ Twitter: https://x.com/donbeebenfl Instagram: https://www.instagram.com/donbeebe82/ Website: https://donbeebe.com/ Books: https://donbeebe.com/store/category/book Facebook: https://www.facebook.com/don.beebe.16 Cameo: https://www.cameo.com/donbeebe82 Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

October 7, 2025Episode 1251 hr 40 min

#125 How to Compete Against Giants Without Losing Your Soul w/ Dave Bolotsky, Founder & CEO, Uncommon Goods

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Dave Bolotsky (@UncommonGoods) is the founder and CEO of Uncommon Goods, a pioneering online marketplace known for its handcrafted, ethically made products and its people-first business model. A former Goldman Sachs retail analyst who traded spreadsheets for storytelling, Dave built Uncommon Goods from his New York apartment into one of the most values-driven eCommerce companies in America.In this conversation with Gary Rabine, Dave shares the lessons he learned from icons like Sam Walton and Bernie Marcus, how he survived the dot-com crash, and why he believes business can — and must — be both profitable and purposeful.In this episode, Gary and Dave discuss:Building a business from the ground up with grit, values, and zero outside fundingHow to lead through crisis — and why firing people taught him his most powerful leadership lessonThe culture of ownership: why Dave meets every new hire and gives employees a stake in successCompeting with Amazon through creativity, relationships, and exclusivityThe enduring impact of purpose-driven leadership and “shared prosperity”LinkedIn: https://www.linkedin.com/in/dave-bolotsky/ Website: https://www.uncommongoods.com/ Facebook: https://www.facebook.com/uncommongoods/ X: https://x.com/uncommongoods Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

September 23, 2025Episode 12441 min

#124 The Founder’s Guide to Storytelling That Inspires Part 2 w/ Lee Habeeb, Our Great American Stories

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Lee Habeeb (@LeeHabeeb) is the creator and host of Our American Stories and one of the nation’s leading voices on storytelling, entrepreneurship, and the American Dream. In this powerful conversation with Gary Rabine, Lee dives deep into how great leaders and founders build enduring cultures, why incentives and recognition matter more than money alone, and how storytelling can unify both companies and the country.In this episode, Gary and Lee discuss:1. Why recognition matters as much as incentives2. Culture doesn’t show up on the balance sheet3. The Chick-fil-A principle4. Storytelling as a leadership toolConnect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

September 19, 2025Episode 12358 min

#123 The Founder’s Guide to Storytelling That Inspires Part 1 w/ Lee Habeeb, Host and Founder, Our Great American Stories

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Lee Habeeb (@LeeHabeeb) is the creator and host of Our American Stories and one of the country’s leading voices on storytelling, entrepreneurship, and the American Dream. In this conversation with Gary Rabine, Lee explores how the power of story has shaped leaders, businesses, and even nations — and why founders and business owners must master it to build companies that last.In this episode, Gary and Lee discuss:1. The power of storytelling in business and leadership 2. Capitalism as a force for innovation3. Integrity and incentives inside companies4. The American Dream redefinedConnect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

June 16, 2025Episode 1221 hr 10 min

#122 How Buying Broken Businesses Built a Thriving Empire w/ Peter Griscom, Principal & Operating Partner, Van Dyke Acquisitions

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/Peter Griscom (https://www.linkedin.com/in/peter-g-350a21169/) is an Operating Partner and the Chief Executive Officer of Van Dyke Acquisitions, a boutique investment firm specializing in distressed mergers and acquisitions and turnaround opportunities. With over a decade of experience in the distressed investing sector, he focuses primarily on healthcare, consumer goods, and manufacturing.In this episode, Gary, Dave, and Peter discuss:1. Early hustle stories and DIY operations2. Breaking into retail and scaling nationally3. Embedding Christian values into business4. Vision for legacy and long-term impactLinkedIn: https://www.linkedin.com/in/peter-g-350a21169/ Twitter: https://x.com/petergriscom Website: https://vdacq.com/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEOTikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEOTwitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo