Ditch Digger CEO with Gary Rabine

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

Ditch Digger CEO with Gary Rabine is a business podcast hosted by Gary Rabine, with 133 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Gary Rabine hosts Ditch Digger CEO with Gary Rabine, a business show with 133 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #135

  #135 Everything is Figureoutable w/ Jennifer Davis for Congress

  Sep 7, 20261h 11m

  Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/ Jennifer Davis is a technology entrepreneur, trade industry pioneer, and candidate running for Illinois’s 8th Congressional District. Starting at just 17 years old alongside her husband Dan, Jennifer co-founded Davisware—a field service technology company that revolutionized logistics, dispatching, and backend accounting for commercial HVAC, food equipment, and petroleum service industries. Raised on a farm in rural Wisconsin as one of nine children, she balances her deep roots in hard work and problem-solving with decades of executive leadership, global operations, and tech innovation. As a mother of 10 and grandmother, she brings a hands-on understanding of what it takes to bootstrap a venture, manage hundreds of employees, navigate regulatory burdens, and build lasting enterprise value from the ground up. In this conversation with Gary Rabine, Jennifer details her transition from building businesses to serving in public office, outlining her drive to restore hope and accountability to governance. Drawing from her background as a "ditch-digger tech entrepreneur," she lays out her vision for protecting families from digital threats, reforming campaign finance, leveraging technology in national security, and empowering job creators to rebuild local communities. In this episode, Gary and Jennifer discuss: The Trades & Tech Fusion: Solving complex logistical problems for field services and building a SaaS powerhouse from scratch. The Digital Dome Framework: Utilizing deep tech and AI insights to protect children and families from online dangers. Campaign Finance & Governance Reform: Eliminating Super PAC dominance, implementing term limits, and ending career politics. Bottom-Up Economic Growth: How strong family businesses create thriving communities and drive state-level renewal. Websites: https://www.votejenniferdavis.com/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

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  Episode #133

  #134 Can Business Leaders Turn This State Around? w/ Darren Bailey and Aaron Del Mar for Illinois

  Aug 17, 20261h 2m

  Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/ Darren Bailey and Aaron Del Mar are entrepreneurs, business builders, and candidates running for Governor and Lieutenant Governor. Darren, a third-generation farmer, trucker, and excavator operator from Southern Illinois, built his operations alongside his family through hard work, accountability, and grit. Aaron, who started as a solo entrepreneur on the North Side of Chicago, scaled his event management business into a national operation employing over 350 people across 40 cities. Together, they bring a hands-on understanding of what it takes to make payroll, navigate complex regulatory environments, and create lasting enterprise value. In this conversation with Gary Rabine, Darren and Aaron detail their campaign stances, economic plans, and vision for governance. Drawing from their experiences as "ditch-digger CEOs," they outline their strategies for capping property taxes, cutting corporate red tape, rebuilding public safety, and bringing job creators back to the state. In this episode, Gary, Darren, and Aaron discuss: The Campaign Stance: Why business owners and job creators are uniquely equipped to fix government mismanagment The Economic Plan: Lowering property and corporate taxes to attract business and expand the overall tax base The Three Pillars: Rebuilding communities around affordability, public safety, and educational reform The "Team of Rivals" Model: Surrounding leadership with best-in-class experts rather than political patronage Websites: https://baileyforillinois.com/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

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  Episode #133

  #133 How World Series Champions Build High-Performance Culture w/ Trent Clark, Coach, CEO at Athletic Influencer Marketing

  Aug 3, 20261h 32m

  Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/ Trent Clark is a 3x World Series coach, serial entrepreneur, keynote speaker, and CEO coach who spent over 12 years coaching at the highest levels of Major League Baseball—winning World Series rings with the 1997 Florida Marlins and the 2002 Los Angeles Angels. Today, as the Founder and CEO of Leadership365 and host of the Winners Find Ways podcast, Trent works with high-growth founders, executives, and organizations to build championship-level team culture, refine leadership systems, and unlock peak operational performance. In this conversation with Gary Rabine, Trent shares his journey from managing three paper routes as an eighth-grader to coaching elite professional athletes and Fortune 500 business leaders. He breaks down how the principles of coachability, adaptability, and dependability translate directly from the dugout to the boardroom. In this episode, Gary and Dean discuss: The ACES Framework: Coachability, Adaptability, Responsibility, and Dependability as the foundation of high-performing teams Early Entrepreneurship: How running paper routes taught delegation, customer service, and leverage at a young age Going the Extra Mile: Customer loyalty, going beyond expectations, and delivering during life’s "floods" Lessons from World Series Champions: Building team culture with players who execute their role consistently Website: https://linktr.ee/TrentMClark LinkedIn: https://www.linkedin.com/in/trentmclark/ Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

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  Episode #132

  #132 Think in Centuries, Not Quarters w/ Tim Schmalz, Sculptor

  Jul 6, 20261h 26m

  Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/ Timothy Schmalz is one of the world's most renowned contemporary sculptors, whose monumental bronze works can be found in churches, cathedrals, public spaces, and pilgrimage sites across the globe. Best known for iconic sculptures such as Homeless Jesus , Angels Unawares , and Let the Oppressed Go Free , Tim has dedicated his career to creating art that inspires reflection, compassion, and faith. His work has been permanently installed at the Vatican, St. Peter's Square, the National Cathedral in Washington, D.C., and hundreds of other locations worldwide, making him one of the most influential religious artists of our time. In this conversation with Gary Rabine, Tim shares how entrepreneurship, creativity, and faith intersect to create a life of lasting impact. From rejecting a backup plan to pursuing mastery with military discipline, he explains why meaningful work requires radical commitment—and why the greatest legacy isn't measured by success, but by what remains long after we're gone. In this episode, Gary and Dean discuss: Why having no Plan B fueled Tim's pursuit of mastery Building a legacy designed to last for centuries How discipline shapes creativity and craftsmanship Finding inspiration where others see ordinary moments Feature of Tim’s work: https://www.youtube.com/watch?v=TFPv6RDaC-8&t=28s Connect with Gary Rabine and DDCEO on: Website: https://www.DitchDiggerCEO.com/ Instagram: https://www.instagram.com/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

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  Episode #131

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

  Jun 8, 20261h 4m

  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 industries The evolution of residential solar, batteries, and distributed energy How service businesses create long-term enterprise value What entrepreneurs can learn from the energy industry's transformation Website: 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO YouTube: https://www.youtube.com/@ditchdiggerceo

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