Ditch Digger CEO with Gary Rabine

Gary Rabine
  • 4.9 (320)
  • BUSINESS
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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

  1. 12/01/2025

    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 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

    1h 19m

  2. 11/24/2025

    #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 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

    1h 6m

  3. 10/13/2025

    #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 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

    1h 41m

  4. 10/07/2025

    #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 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

    1h 40m

  5. 09/23/2025

    #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 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

    42 min

  6. 09/19/2025

    #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 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

    59 min

  7. 06/16/2025

    #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 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

    1h 10m

  8. 06/11/2025

    #121 Build Millionaires, Not Just Businesses w/ Dave Durand, Founder & CEO, Leading Giants

    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

    1h 35m
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4.9
out of 5
320 Ratings

About

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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