65 episodes

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 and is currently the CEO of 9 companies.
Quinton, a millennial, is the leader of a Mentoring non profit, True Mentors, that matches successful CEO’s with motivated entrepreneurs.

For business inquiries email PodcastDDCEO@gmail.com

Ditch Digger CEO with Gary Rabine Gary Rabine

    • Business
    • 5.0 • 306 Ratings

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 and is currently the CEO of 9 companies.
Quinton, a millennial, is the leader of a Mentoring non profit, True Mentors, that matches successful CEO’s with motivated entrepreneurs.

For business inquiries email PodcastDDCEO@gmail.com

    #60 - The Road to $1 Billion w/ Rob Wilson - President, The Wilson Companies / Employco USA, Inc.

    #60 - The Road to $1 Billion w/ Rob Wilson - President, The Wilson Companies / Employco USA, Inc.

    Rob Wilson (@employco) is president of Employco USA. Employco is a national HR outsourcing firm whose customized business solution have made them one of the top privately held HR outsourcing companies in the country. They work with companies to tailor outsourced solutions for payroll, HR, employee benefits and workers’ compensation insurance while reducing clients’ expenses by leveraging their substantial buying power. During the pandemic, Employco led more than 35 webinars on PPP loans and assisted more than 300 clients in applying for funds and loan forgiveness.  In 2015, Employco USA was recognized in Inc Magazine as one of the fastest growing companies in America.  This year, Employco proudly celebrated 25 years of outstanding service.

    Rob is a high-energy leader and an ambitious entrepreneur. He’s frequently interviewed by news publications, and is a sought-after public speaker. He’s been quoted by Fox News, Wall Street Journal, NBC, Forbes, USA Today, Reuter’s, Newsday, CNBC, Chicago Tribune, Crain’s Chicago Business, and WGN Television. Rob was recognized by Crain’s Chicago Business on their 2021 list of Notable Leaders in HR. He’s also been honored as a finalist for both Ernst & Young (Entrepreneur of the Year competition), and Business Ledger Magazine (Today’s Young Executive competition).  

    Website: www.employco.com

    Twitter: @employco 

    LinkedIn: https://www.linkedin.com/in/robwilson-twc/ 

    Check out https://www.DitchDiggerCEO.com/ for this week's TOP 8 Business Growth strategies and subscribe to our newsletter to download Gary’s 13 Keys to Creating a Multi-Million Dollar Business.



    Follow us on Instagram @DitchDiggerCEO for more helpful Business Growth tips.

    Our goal is to inspire everyone to start their own business and help you grow it to millions or even billions in value so if you feel any benefit from this episode please let us know by leaving an iTunes review, sharing this episode on social media and emailing a link to anyone you think would also find benefit here. Thank you. 



    02:30 Start

    03:35 Getting to know Rob Wilson  

    09:00 Rob Wilson’s family  

    13:35 Starting his first company 

    15:30 Working with his dad  

    18:35 Business niches  

    21:00 Expanding the insurance and consulting business  

    24:50 The risk in taking risks  

    28:45 Going through recessions and setbacks 

    37:30 A look at how COVID affected businesses and their States’ response 

    48:40 A look back at the growth of Rob’s company  

    51:30 Becoming friends with customers 

    54:30 Holding people accountable to your core values 

    58:20 Rob’s vision  

    1:04:35 Rob’s executive coach 

    1:11:00 Rob’s family life  



    Connect with Gary Rabine and DDCEO: 

    Visit the DDCEO BLOG: https://www.DitchDiggerCEO.com/ 

    Follow DDCEO on Instagram: https://www.instagram.com/DitchDiggerCEO

    Like DDCEO on Facebook: https://www.facebook.com/DitchDiggerCEO

    Follow DDCEO on Twitter: https://twitter.com/DitchDiggerCEO 

    • 1 hr 21 min
    #59 Builder/Developer/Entrepreneur, Write your own Story, w/ Charles Hall

    #59 Builder/Developer/Entrepreneur, Write your own Story, w/ Charles Hall

    Charles G. (Chuck) Hall IV is the Chairman of Vitality Living and founder and CEO of Charles Hall Construction, LLC.

    Vitality Living is a team of seasoned retirement living professionals passionate about creating vibrant communities for older adults, regardless of physical and/or cognitive challenges. Our goals are to eliminate labels that reinforce stereotypes of aging, to empower choice, and to create environments where all residents are successful.

    Charles Hall Construction, LLC, stands near the head of the class as one of the nation's leading builders and developers of senior living, active adult and multi-family communities. Founded in 1998, the company has been widely recognized for innovations it has pioneered to enrich the lifestyle and practical needs of today's families, while meeting the goals and requirements of clients, partners, and residents, alike.

    http://hallmanagement.com/

    https://www.vitalityseniorliving.com/

    Check out https://www.DitchDiggerCEO.com/ for this week's TOP 8 Business Growth strategies and subscribe to our newsletter to download Gary’s 13 Keys to Creating a Multi-Million Dollar Business.

    Follow us on Instagram @DitchDiggerCEO for more helpful Business Growth tips.

    Our goal is to inspire everyone to start their own business and help you grow it to millions or even billions in value so if you feel any benefit from this episode please let us know by leaving an iTunes review, sharing this episode on social media and emailing a link to anyone you think would also find benefit here. Thank you. 



    02:20 Hello!

    04:40 Getting to know Charles Hall 

    07:30 Finding the right partners for your business 

    09:50 Charles’ childhood 

    17:50 Charles’ greatest lessons from his parents 

    23:00 Meeting Molly and moving to New York  

    27:45 Charles’ relationship with his family 

    28:35 You can write your own life  

    31:50 Starting his own business 

    35:45 Building Charles Hall Construction from the ground up 

    43:20 Moving to Clarendon Hills 

    45:35 Charles Hall Construction and Vitality Living 

    59:50 Charles’ new goals  

    1:08:50 You have the tools to write your own story 



    Connect with Gary Rabine and DDCEO: 

    Visit the DDCEO BLOG: https://www.DitchDiggerCEO.com/ 

    Follow DDCEO on Instagram: https://www.instagram.com/DitchDiggerCEO

    Like DDCEO on Facebook: https://www.facebook.com/DitchDiggerCEO

    Follow DDCEO on Twitter: https://twitter.com/DitchDiggerCEO 

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg

    • 1 hr 30 min
    #58 Learning, Earning, Serving, 3 Parts of a Life Worth Living w/ Jeff Wald - Founder, WorkMarket

    #58 Learning, Earning, Serving, 3 Parts of a Life Worth Living w/ Jeff Wald - Founder, WorkMarket

    Jeff Wald is the Founder of Work Market, an enterprise software platform that enables companies to manage freelancers (acquired by ADP). Jeff has founded several other technology companies, including Spinback, a social sharing platform (acquired by salesforce.com). Jeff is an active angel investor and startup advisor, as well as serving on numerous public and private Boards of Directors. Jeff is the author of the Amazon Best Seller The End of Jobs: The Rise of On-Demand Workers and Agile Corporations. 

    Twitter: @jeffreywald 

    LinkedIn: https://www.linkedin.com/in/jeffwald/  

    Website: www.jeffwald.com

    Check out https://www.DitchDiggerCEO.com/ for this week's TOP 8 Business Growth strategies and subscribe to our newsletter to download Gary’s 13 Keys to Creating a Multi-Million Dollar Business.

    Follow us on Instagram @DitchDiggerCEO for more helpful Business Growth tips.

    Our goal is to inspire everyone to start their own business and help you grow it to millions or even billions in value so if you feel any benefit from this episode please let us know by leaving an iTunes review, sharing this episode on social media and emailing a link to anyone you think would also find benefit here. Thank you. 



    02:23 How Jeff Wald got started  

    06:10 Starting his own company  

    09:00 Dealing with setbacks and getting back up 

    14:50 Does new technology take away jobs? 

    17:25 Starting WorkMarket  

    24:20 What makes Work Market great  

    41:30 Jeff’s new mission  

    43:40 The End of Jobs  

    51:15 The best minds are those who want to solve problems  

    54:00 Hire somebody that wants your job 

    59:55 What needs to change in politics  

    1:07:50 Unintended positive and negative consequences  

    1:18:20 What it means to be a leader 



    Connect with Gary Rabine and DDCEO: 

    Visit the DDCEO BLOG: https://www.DitchDiggerCEO.com/ 

    Follow DDCEO on Instagram: https://www.instagram.com/DitchDiggerCEO

    Like DDCEO on Facebook: https://www.facebook.com/DitchDiggerCEO

    Follow DDCEO on Twitter: https://twitter.com/DitchDiggerCEO 

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg

    • 1 hr 30 min
    #57 The King Maker’s Mindset w/ Mike Berland - Founder and CEO of Decode_M

    #57 The King Maker’s Mindset w/ Mike Berland - Founder and CEO of Decode_M

    Mike Berland is the Founder and CEO of Decode_M, an insights and analytics firm research and analytics firm that decodes data into momentum for its clients. In a world that runs on data, Mike strongly believes that everything is knowable, you just have to know where to look. Throughout his career, he has represented prominent political figures, major companies and social movements. Prior to founding Decode_M, he was the CEO of the insights and analytics arm of Edelman Public Relations, Edelman Berland, and President of the research and political polling firm Penn, Schoen & Berland.

    Website: https://www.decode-m.com/ 

    Facebook: https://www.facebook.com/Decode-M-115056910035445/ 

    Twitter: https://twitter.com/Decode_Momentum 

    Instagram: https://www.instagram.com/decode_momentum/

    Check out https://www.DitchDiggerCEO.com/ for this week's TOP 8 Business Growth strategies and subscribe to our newsletter to download Gary’s 13 Keys to Creating a Multi-Million Dollar Business.

    Follow us on Instagram @DitchDiggerCEO for more helpful Business Growth tips.

    Our goal is to inspire everyone to start their own business and help you grow it to millions or even billions in value so if you feel any benefit from this episode please let us know by leaving an iTunes review, sharing this episode on social media and emailing a link to anyone you think would also find benefit here. Thank you. 



    03:30 What Mike learned in YPO 

    04:45 Who are Mike’s customers 

    08:45 The state of politics in Illinois 

    14:00 The similarities between business and politics  

    24:00 Identifying the momentum drivers for a company  

    25:45 Abundance 360 and moonshots  

    28:15 Disruption and polarization 

    32:00  Social impact  

    35:30 Being negative vs being positive 

    41:45 Mike’s childhood and 9/10/2001  

    46:45 Post 9/11 and the NHL 

    53:30 Public relations and momentum  

    1:00:00 Getting into the momentum mindset 

    1:03:45 Are things coming back to normal? 

    1:13:45 Mike’s family  

    1:17:45 Mike’s take on politics  

    1:21:15 Chris’ takeaways



    Connect with Gary Rabine and DDCEO: 

    Visit the DDCEO BLOG: https://www.DitchDiggerCEO.com/ 

    Follow DDCEO on Instagram: https://www.instagram.com/DitchDiggerCEO

    Like DDCEO on Facebook: https://www.facebook.com/DitchDiggerCEO

    Follow DDCEO on Twitter: https://twitter.com/DitchDiggerCEO 

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg

    • 1 hr 41 min
    #56 Explosive Growth of Virtual Assistants w/ John Jonas - Founder of OnlineJobs.ph

    #56 Explosive Growth of Virtual Assistants w/ John Jonas - Founder of OnlineJobs.ph

    John Jonas helped thousands of entrepreneurs succeed in their business by doing outsourcing differently. He created the world’s largest website for finding Filipino Virtual Assistants, OnlineJobs.ph, which has over 1,000,000 Filipino resumes and hundreds of thousands of employers from around the world using it. 

    John had a normal "job" for 8 months after college and his biggest goal at that time was to be able to quit that job. He managed to quit back in 2004 and worked from home for himself ever since then. It was in 2006 that he first hired someone from the Philippines, he immediately knew he was onto something special.

    LINKS:

    Website: http://www.onlinejobs.ph 

    Facebook: https://www.facebook.com/johnjonasofficial 

    YouTube: https://www.youtube.com/channel/UCXKa0JRgZg0kiZbU_w5bW0A? 

    Testimonials: https://www.onlinejobs.ph/success-stories 



    Check out https://www.DitchDiggerCEO.com/ for this week's TOP 8 Business Growth strategies and subscribe to our newsletter to download Gary’s 13 Keys to Creating a Multi-Million Dollar Business.



    Follow us on Instagram @DitchDiggerCEO for more helpful Business Growth tips.

    Our goal is to inspire everyone to start their own business and help you grow it to millions or even billions in value so if you feel any benefit from this episode please let us know by leaving an iTunes review, sharing this episode on social media and emailing a link to anyone you think would also find benefit here. Thank you. 



    01:30 Getting to know John Jonas  

    04:41 How Onlinejobs.ph works  

    08:40 John’s childhood 

    010:55 Building his own business 

    17:40 The importance of adding value  

    19:00 How OnlineJobs started 

    21:45 Why John decided to build a business with Filipinos 

    26:30 John’s relationship with his employees 

    35:00 The challenges of hiring virtual VAs  

    39:10 Challenges that John faced  

    46:00 Training leaders to make the most out of each opportunity 

    54:30 How VAs can ease your life  

    57:30 Aiming for excellent customer experience 

    1:02:47 Why the Philippines is so appealing  

    1:04:25 Replacemyself.com  

    1:15:16 What John does in his spare time 



    Connect with Gary Rabine and DDCEO: 

    Visit the DDCEO BLOG: https://www.DitchDiggerCEO.com/ 

    Follow DDCEO on Instagram: https://www.instagram.com/DitchDiggerCEO

    Like DDCEO on Facebook: https://www.facebook.com/DitchDiggerCEO

    Follow DDCEO on Twitter: https://twitter.com/DitchDiggerCEO 

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg

    • 1 hr 37 min
    #55 Boot Strapping Champion of Fashion w/ Brian Spaly - Founder of Trunk Club

    #55 Boot Strapping Champion of Fashion w/ Brian Spaly - Founder of Trunk Club

    Brian Spaly (@BrianSpaly) is currently the General Partner at Brand Foundry Ventures and Executive Chairman at Tecovas, a direct-to-consumer Western Bootmaker based in Austin, TX.  Up until January 2017, Brian was Founder and CEO of Trunk Club, where he focused on making it easy for men and women to discover and acquire awesome clothing without the hassles of the traditional shopping experience. 

    Prior to leading Trunk Club, Brian founded Bonobos, a men’s clothing company that is famous for the best-fitting pants on earth, by selling trousers out of the trunk of his car during business school in Palo Alto.

    Brian holds an MBA from Stanford and an AB degree from Princeton. He is an avid hockey player, cyclist, squash player, and enjoys watersports. He’s completed three Ironman distance triathlons and three adventures to Burning Man. His favorite authors are Roald Dahl, Neal Stephenson, Mark Helprin, and Nicholas Taleb. He is married to Carly Spaly and they have two daughters, Ruthie and Sylvie.

    https://www.linkedin.com/in/brianspaly/  

    https://twitter.com/brianspaly?lang=en  

    Check out https://www.DitchDiggerCEO.com/  for this week's TOP 8 Business Growth strategies and subscribe to our newsletter to download Gary’s 13 Keys to Creating a Multi-Million Dollar Business.

    Follow us on Instagram @DitchDiggerCEO for more helpful Business Growth tips.

    Our goal is to inspire everyone to start their own business and help you grow it to millions or even billions in value so if you feel any benefit from this episode please let us know by leaving an iTunes review, sharing this episode on social media and emailing a link to anyone you think would also find benefit here. Thank you. 



    02:30 Getting to know Brian Spaly 

    05:15 Discovering his entrepreneurial side  

    09:15 The private equity guy who made his own clothes 

    11:00 Finding your passion beyond conventional jobs  

    15:30 Bonobos’ history and differentiation 

    21:30 Success, responsibility, and life lessons from business 

    30:45 Letting go of Bonobos 

    40:00 Brian’s career with Trunk Club 

    49:30 What companies excite Brian Spaly to invest 

    1:04:45 Mentors that inspired Brian 

    1:11:30 How Brian inspires his team  

    1:18:15 Balancing your company’s priorities 



    Connect with Gary Rabine and DDCEO: 

    Visit the DDCEO BLOG: https://www.DitchDiggerCEO.com/  

    Follow DDCEO on Instagram: https://www.instagram.com/DitchDiggerCEO 

    Like DDCEO on Facebook: https://www.facebook.com/DitchDiggerCEO 

    Follow DDCEO on Twitter: https://twitter.com/DitchDiggerCEO  

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg

    • 1 hr 41 min

Customer Reviews

5.0 out of 5
306 Ratings

306 Ratings

Tony Ebel ,

Can’t get enough of this one!

Really love how it starts with family and origin stories each time, and how each person interviewed shares the key attributes of being humble, hungry and driven, servant minded, and always adapting and situationally aware! So many lessons learned each time on how apply each of those things consistently across business and personal life.

DJNA13 ,

Podcast is inspirational.

Thank you for sharing you experiences & stories from your life. Keep up the good work.🇺🇸

Scott Builds Better ,

Incredible perspectives packed into every podcast

Ditch Digger CEO is worth every minute of your time. An all-star lineup of entrepreneurs and executives sharing insight and lessons-learned you won’t find anywhere else. This is one of my go-to podcasts!

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