Advertise on podcast: Ditch Digger CEO with Gary Rabine

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

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

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 Trent 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

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

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

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 transformation The difference between real online learning and “Zoom school” How AI will reshape education and business leadership Why 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast  Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO  YouTube: https://www.youtube.com/@ditchdiggerceo

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 wall The power of transferable trust in business relationships How mentors and tough coaches shape great leaders The three traits every entrepreneur must develop: persistence, responsibility, and self-confidence Website: 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast  Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO  YouTube: https://www.youtube.com/@ditchdiggerceo

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 industries Lessons learned from co-founding Halo and scaling modern wealth-tech How discipline, precision, and vision guide Biju’s approach to innovation The mission behind the Vidya Foundation and why education unlocks opportunity LinkedIn: 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast  Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO  YouTube: https://www.youtube.com/@ditchdiggerceo

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 scale How a failed stuffed-animal startup taught him everything about inventory and demand The dot-com rollercoaster: raising $40M, preparing for a $1B IPO, then crashing to zero Why founders should go slow now to go fast later LinkedIn: 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast  Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO  YouTube: https://www.youtube.com/@ditchdiggerceo

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 growth Why faith, discipline, and character outlast talent and opportunity Building a winning culture: from 17 kids in a gym to state champions The leadership principle behind the legendary “Leon Lett Play” How to instill humility, passion, and belief in your team LinkedIn: 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast  Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO  YouTube: https://www.youtube.com/@ditchdiggerceo

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 funding How to lead through crisis — and why firing people taught him his most powerful leadership lesson The culture of ownership: why Dave meets every new hire and gives employees a stake in success Competing with Amazon through creativity, relationships, and exclusivity The 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast  Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO  YouTube: https://www.youtube.com/@ditchdiggerceo

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 incentives 2. Culture doesn’t show up on the balance sheet 3. The Chick-fil-A principle 4. Storytelling as a leadership tool 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

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 innovation 3. Integrity and incentives inside companies 4. The American Dream redefined 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

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 operations 2. Breaking into retail and scaling nationally 3. Embedding Christian values into business 4. Vision for legacy and long-term impact LinkedIn: 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/DitchDiggerCEO TikTok: https://www.tiktok.com/@ditchdiggerceopodcast  Facebook: https://www.facebook.com/DitchDiggerCEO Twitter: https://twitter.com/DitchDiggerCEO  YouTube: https://www.youtube.com/@ditchdiggerceo

Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www.DitchDiggerCEO.com/ Dave Durand (https://www.linkedin.com/in/davevdurand/) is currently the CEO of Leading Giants and Executive Chairman of Best Version Media, an international media company in Brookfield, Wisconsin. During Durand’s tenure as CEO, BVM was among the top 20 fastest-growing media companies in North America and the fastest-growing private company in Wisconsin of any type. In 2024, The Wall Street Journal publicized a BVM as one of the Top 100 Best & Brightest Companies To Work For in the Nation. In this episode, Gary and Dave discuss: 1. Business Exits and Second Bites at the Apple 2. Scaling “Dirty” Businesses with Innovation 3. Organic Growth vs. Acquisition Strategies 4. Entrepreneurship Without Industry Experience LinkedIn: https://www.linkedin.com/in/davevdurand/   Twitter: https://x.com/durandondemand  YouTube: https://www.youtube.com/@durandondemand  Instagram: https://www.instagram.com/durandondemand/?hl=en Facebook: https://www.facebook.com/Durandleadershipgroup/  Podcast: https://podcasts.apple.com/us/podcast/durand-on-demand/id1729237093  Newsletter: https://leadinggiants.com/newsletter/  Books: https://www.amazon.com/stores/author/B001JS7XPM  Courses: https://leadinggiants.com/courses/the-ceo-giant-masterclass/  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