Ditch Digger CEO with Gary Rabine

Gary Rabine

Booking Overview

An entrepreneurship and business interview show focused on founders and executives who built substantial companies through grit, disciplined execution, leadership, and innovation; recent external guests are predominantly CEOs, founders, and accomplished industry leaders. Credible pitches include company builders, operators, and experts with demonstrable business results or firsthand experience scaling organizations, entering emerging markets, or transforming industries; booking difficulty is medium.

Metrics

Episodes: 139

Frequency: Monthly

Rating: 4.9/5.0

Estimated listeners: 1k-10k

Gender skew: Male

Location: USA

YouTube: 108 subscribers

Instagram: 1.4k followers

Contact Information

Publicly listed emails

garyrabine@ditchdiggerceo.com

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Host

Gary Rabine - Serial entrepreneur who has started 25 companies over the past 20 years, with experience building businesses from the ground up and guiding entrepreneurial growth.

Booking Intelligence

Booking Requirements

medium

Typical Credentials:

Founders, CEOs, presidents, and senior executives with substantial experience building, scaling, or transforming companies, especially in construction, energy, technology, finance, education, transportation, or other evolving industries.

Required Achievements:

Founded or co-founded successful companies, Scaled businesses or entered new markets, Led major industry transformations, Developed notable technologies, platforms, or operating models, Built recognized expertise through extensive executive experience

Recent Guest Discussions

Timothy Schmalz - Entrepreneurship, Mastery, Discipline, Creativity, Meaningful Work, And Building A Lasting Legacy.

John Berger - Finding Hidden Markets, Fragmented Industries, Distributed Energy, Service-business Value, And Entrepreneurship In Evolving Markets.

Beth Hollenberg - Higher Education Transformation, Artificial Intelligence, Online Learning, Adaptability, Empathy, And Leadership.

Dean Vicha - Business Culture, Trust, Mentorship, Accountability, Persistence, Responsibility, And Navigating Industry Transformation.

Biju Kulathakal - Reinventing Industries, Robotics, Artificial Intelligence, Fintech, Construction Innovation, Disciplined Execution, And Scaling Across Sectors.

Recent Topics

Entrepreneurship, Founders, Business, Leadership, Innovation

Episodes

Here's the recent few episodes on

Ditch Digger CEO with Gary Rabine

#135 Everything is Figureoutable w/ Jennifer Davis for Congress

September 07, 2026

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....

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

August 17, 2026

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 e...

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

August 03, 2026

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, ex...

Publicly listed emails

garyrabine@ditchdiggerceo.com

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