Gary Rabine
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
Author
Gary Rabine
Category
Podcast website
Latest episode
Jul 6, 2026
Where to listen?
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Episodes
#132 Think in Centuries, Not Quarters w/ Tim Schmalz, Sculptor 06.07.2026 1:26:12
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 Oppr...
#131 How Great Entrepreneurs Find Hidden Markets w/ John Berger, CEO at Otovo 08.06.2026 1:04:17
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 generato...
#130 How to Build Trust in an AI-Driven World w/ Beth Hollenberg, Chief Executive Officer, Everspring 22.05.2026 1:22:38
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, an...
#129 Culture Isn’t What You Put on the Wall — It’s What You Do Every Day w/ Dean Vicha, President at NationaLease 17.03.2026 1:09:55
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...
DDC #128 The Discipline of Moving Fast Without Breaking What Matters w/ Biju Kulathakal, Founder and CEO, LightSpeed | Halo Investing 01.12.2025 1:19:15
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...
#127 Converting Your Business From a Vitamin to A Painkiller w/ Tim Stojka, CEO, Nexus3 Capital 24.11.2025 1:06:28
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 duri...
#126 The Three Prayers That Built a Champion w/ Don Beebe, Head Football Coach, Aurora University, Former NFL Player, Founder, House of Speed 13.10.2025 1:41:01
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 perse...
#125 How to Compete Against Giants Without Losing Your Soul w/ Dave Bolotsky, Founder & CEO, Uncommon Goods 07.10.2025 1:40:27
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...
#124 The Founder’s Guide to Storytelling That Inspires Part 2 w/ Lee Habeeb, Our Great American Stories 23.09.2025 41:41
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,...
#123 The Founder’s Guide to Storytelling That Inspires Part 1 w/ Lee Habeeb, Host and Founder, Our Great American Stories 19.09.2025 58:32
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...
#122 How Buying Broken Businesses Built a Thriving Empire w/ Peter Griscom, Principal & Operating Partner, Van Dyke Acquisitions 16.06.2025 1:10:13
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 th...
#121 Build Millionaires, Not Just Businesses w/ Dave Durand, Founder & CEO, Leading Giants 11.06.2025 1:34:47
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 Nort...
#120 AccuWeather: From a $50 Startup to a Global Powerhouse w/ Dr. Joel Myers, Founder & Executive Chairman, AccuWeather 21.05.2025 1:12:45
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Dr. Joel N. Myers ( https://corporate.accuweather.com/company/about-us/dr-joel-myers/ ) is a proven visionary leader, founding AccuWeather in 1962 and successfully establishing it as the world's fastest growing and most trusted source of weather forecasts and warnings as well as a global l...
#119 Why the Best Outsourcing Isn’t Really Outsourced w/ Jose Herrera, CEO & Co-Founder, Horatio 06.05.2025 1:16:21
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Jose Herrera ( https://www.linkedin.com/in/joseherrerap/ ) is the CEO and Co-Founder of Horatio. Horatio is the trusted partner for some of the fastest-growing startups and enterprises in the world. Their on-brand customer support teams help them leverage CX as a revenue generator through pers...
#118 AI, Learning, and the Future of Work: Staying Ahead of the Curve w/ David Blake, Co-founder & CEO, Degreed 24.02.2025 1:12:01
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ David Blake ( https://degreed.com/ ) is the co-founder and Executive Chairman of Degreed. Millions of individuals and hundreds of organizations use Degreed’s platform to discover and answer for all of their learning and skills. Prior to Degreed, he consulted on the launched a competency-based,...
#117 Pleaser, Dreamer, Innovator: The Story of Joe Kahn | Founder & CIO | Condado Tacos 20.12.2024 1:18:53
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Meet Joe Kahn , founder of Condado Tacos, who turned his passion for the restaurant industry into a thriving 51-store chain. In this episode, Joe shares his journey from busboy to CEO, focusing on explosive growth, maintaining a strong company culture, and innovative strategies...
#116 From Humble Beginnings To Billion-Dollar Success w/ Stan Middleman, Founder, Freedom Mortgage 23.10.2024 1:03:04
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Stanley C. Middleman is the Founder, President & CEO of Freedom Mortgage Corporation. In today's episode, Stan recounts his journey from starting with nothing in 1990 to leading a multi-billion-dollar enterprise. He covers his entrepreneurial challenges, innovative strategies, and...
#115 From Idea to Impact: The Data Intelligence Revolution w/ Satyen Sangani, CEO, Alation 02.10.2024 1:17:42
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Satyen Sangani , is the Co-Founder and CEO of Alation. Discover Satyen's journey from Wall Street to Silicon Valley, the creation of a groundbreaking data intelligence platform, and the future of AI and data across industries. Gain insights into economics and market dynamics and valuabl...
#114 Revolutionizing Online Learning w/ Pierre Dubuc, Co-Founder & CEO, OpenClassrooms 18.09.2024 1:16:42
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Pierre Dubuc ( https://www.linkedin.com/in/pdubuc/ ), the Forbes 30 Under 30 honoree and innovative CEO of OpenClassrooms shares his journey from starting a hobby business in middle school to creating a leading online education platform, Pierre shares his story of making education acces...
#113 From Notarization to National Impact w/ Pat Kinsel, Founder & CEO , Proof (Formerly Notarize) 29.08.2024 1:13:55
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Pat Kinsel is the founder and CEO of Proof (formerly Notarize). He shares his remarkable journey of transforming the notarization industry with cutting-edge digital solutions. Discover Pat's background, the obstacles he overcame, and how his company tackles fraud and builds trust...
#112 The Tech Innovator’s Playbook w/ Brett Hurt, CEO & Co-Founder, data.world 20.08.2024 1:18:15
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Brett Hurt , is the founder and CEO of data.world. Brett talks about his entrepreneurial journey from Austin, Texas to creating transformative tech enterprises. He discusses the impact of AI on data management, the significance of mentorship, and the role of venture capital in accelera...
#111 Pioneering Eco-Friendly Solutions w/ Stuart Landesberg, Co-Founder & CEO, Grove Collaborative 27.07.2024 1:05:11
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Stuart Landesberg is the Co-Founder and CEO of Grove Collaborative, the leading digital-first brand & e-commerce platform for natural home and personal care. In today's episode, he delves into his journey from a sustainable upbringing to leading a top company in eco-friendly cons...
#110 Navigating The Skies of Innovation w/ Dean Donovan, MD & Co-Founder, DiamondStream Partners 08.07.2024 1:20:28
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Dean Donovan ( https://www.linkedin.com/in/william-dean-donovan/ ), MD and Co-Founder of DiamondStream Partners shares his captivating journey from his early entrepreneurial days in Silicon Valley to leading global businesses and founding Mexico's largest low-cost airline, Volaris....
#109 Pavers Series: Paving a Path of Excellence W/ Mauro Comuzzi, President & CEO, The Paving Lady 20.05.2024 1:02:23
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Mauro Comuzzi ( https://pavinglady.com/ ), founder of 'The Paving Lady,' shares his incredible journey from Venezuela to building a reputable paving business in the USA. Mauro talks about his experiences in the paving industry, the importance of clear expectations, and his thoughts o...
#108 From Ditch Digger to Aviation Mogul w/ Abdol Moabery, President and CEO, GA Telesis 14.05.2024 1:19:39
Download Gary’s 13 Keys to Creating a Multi-Million Dollar Business from https://www. DitchDiggerCEO.com/ Abdol Moabery ( https://twitter.com/AbdolMoabery ), aviation leader and founder of GA Telesis, covers his journey from modest beginnings to steering his company through major crises like the 2008 financial downturn and the COVID-19 pandemic, notably without layoffs. Moabery highlights the impo...
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