50 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, 287 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

    #45 Flaunt Your Flaws w/ Chris Joyce, Gusher Founder

    #45 Flaunt Your Flaws w/ Chris Joyce, Gusher Founder

    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 (https://www.instagram.com/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.

    Chris Joyce (@dealrules) is the founder of 24 companies in high tech, consumer goods, health, and manufacturing. His products have been sold in more than 11,000 stores in 23 countries, with users in 148 countries across the globe. His newest venture is Gusher: the simple, quick, and easy way to create and build a startup without the need for investors or capital. Gusher helps Entrepreneurs create and launch startups using time equity. Everything from technology, media, and health to design, finance, and gaming. If you have a great idea and need the expertise of others to help bring it to life, Gusher can help. Go to the Gusher site and get started: www.gusher.co  

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

    7:30 - Lessons you learn from early entrepreneurial experience

    10:00 - How dealing with $#^! makes you stronger 

    19:30 - Why building a business from scratch is better training than college 

    21:20 - Exposure is everything 

    30:00 - Riding the low-carb coaster 

    34:10 - Why you should never build on someone else’s trend 

    40:30 - VIM for vigor: identifying your Vested Interest Market 

    44:00 - Can you really succeed with nothing but a great idea and great people? 

    52:10 - What ties together all successful entrepreneurs 

    1:01:00 - Confidence and gender inequality  

    1:03:30 - Do what you know, and teach your kids that 

    1:09:50 - Why you should never kill ideas & never give up 

    1:13:20 - The most effective way to increase sales right now 

    1:30:50 - Rob’s 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 38 min
    #44 Reverse Engineering Moonshot Goals w/ Ann Hiatt, Executive Business Partner to Jeff Bezos and Eric Schmidt

    #44 Reverse Engineering Moonshot Goals w/ Ann Hiatt, Executive Business Partner to Jeff Bezos and Eric Schmidt

    Ann Hiatt (@AnnRHiatt) received her initial business training during 15 years as the Executive Business Partner to Jeff Bezos (CEO of Amazon) and Chief-of-Staff to Eric Schmidt (CEO and Executive Chairman at Google/Alphabet). Ann now consults with executives and companies across the globe to reverse engineer their moonshot goals and get results. Ann is a sought-after international speaker and is on several advisory boards. Ann has recently relocated from Silicon Valley to Europe and brings with her a unique perspective on what it takes to succeed in business today.

    In this episode, we talk to Ann about her amazing career with Amazon and Google. She describes her journey from her early years to becoming a name in leadership and management after working with Jeff Bezos and Eric Schmidt. Now, she manages her own consulting firm and shares to us her learnings and experiences in leadership and striving to be a better CEO.

    http://www.annhiatt.co

    https://www.instagram.com/annhiatt/

    https://twitter.com/AnnRHiatt

    https://www.linkedin.com/in/ann-hiatt/



    1:45 Who is Ann Hiatt?

    09:06 Ann’s ‘interview’ for Amazon

    14:06 Is grit a factor in getting hired?

    15:55 How Ann’s father’s military background help shape her

    24:36 Working in Amazon

    27:12 Ann’s biggest challenge at Amazon

    29:55 Women leaders

    35:11 Ann’s Book

    37:11 What make these great CEOs and Leaders great?

    40:41 Being the dumbest person in the room and leadership

    46:34 Always being challenged

    51:18 What’s Ann Hiatt doing now?

    1:01:59 Ann’s experience doing business in Europe

    1:05:25 AI needs in companies

    1:12:29 Ann’s Moonshot mindset

    1:16:28 Smart people with no egos are a recipe to success

    1:22:31 Robbie’s take on Ann’s career and journey

    1:25:21 Talent is distributed equally, but opportunity is not

    1:29:20 Diversity in tech

    1:32:11 The value in risk-taking



    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 47 min
    #43 Core Values Are Not Negotiable w/ Brent Brodeski, CEO of Savant

    #43 Core Values Are Not Negotiable w/ Brent Brodeski, CEO of Savant

    Brent is the co-founder and CEO of Savant Capital Management, a nationally ranked wealth management firm that manages over 8 billion in assets for 6000 clients and employs over 200 professionals and team members.

    Brent earned degrees in finance and economics and an MBA from Northern Illinois University. He is a Certified Financial Planner (CFP®), Certified Public Accountant (CPA), a Chartered Financial Analyst® (CFA®), and an Accredited Investment Fiduciary Analyst® (AIFA®).

    He is a member of the Young Presidents' Organization (YPO) and serves on the boards of the Northern Illinois University Foundation and the Rock Valley College Foundation.

    Chicago magazine named Brent as the #1 independent financial advisor in Chicagoland. He represents Savant on the Barron’s Hall of Fame as one of the nation’s top financial advisors for over 10 years.  He was also ranked by Forbes as the #40 top wealth advisor in the nation.

    Brent’s passions are being an entrepreneur, drinking wine, and spending time with his family at his lake home in Lake Geneva, WI!

    Website: https://www.savantcapital.com/

    Twitter: https://twitter.com/savantweets

    LinkedIn: https://www.linkedin.com/company/savant-capital-management/

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



    05:30- The Brodeski family council

    07:50 - How education creates confidence

    09:00 - Extroversion can be learned

    30:15 - Synergy can be strategized

    33:00 - Why you need systems and structures

    37:00 - The value of hiring subject matter experts 

    46:00 - Growing without the pains

    51:00 - Creating a master playbook by combining the best of all involved

    53:58 - Core values are non-negotiable

    59:15 - How to hire like a boss

    1:08:30 - Robbie’s take-aways



    Connect with Gary Rabine and DDCEO:

    Visit the DDCEO BLOG: http://ditchdiggerceo.com/

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

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

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

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg/featured?view_as=subscriber

    • 1 hr 16 min
    #42 Build a Network to Defeat a Network w/ Anthony “Ozzie” Giglio, CEO/Dealer Principal of Windy City Motorcycle Company

    #42 Build a Network to Defeat a Network w/ Anthony “Ozzie” Giglio, CEO/Dealer Principal of Windy City Motorcycle Company

    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 (https://www.instagram.com/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.

    Anthony G. “Ozzie” Giglio is CEO/Dealer Principal of Windy City Motorcycle Company (WCMC). Ozzie’s experience has run the gamut. He was active duty USN, where he served four tours in the middle east as part of a special ops team focused on counter intel and counter terrorism. He’s now a captain in the Navy Reserve. He holds a JD and is barred in Illinois and Texas. He practiced corporate law, but transitioned to financial services, where he worked on transactions and acquisitions, including real estate. This teed him up for success as the CEO of Windy City Real Estate Group and the eventual acquisition of 10 Harley Davidson dealerships. He founded WC-F with his wife, Jill, in 2000 and they now have 18 locations and employ over 400 people.

    https://youtu.be/d1PBIBTZsJ4

    https://bizcasthq.com/cxo/ozzie-giglio/

    https://www.linkedin.com/company/windy-city-motorcycle-company/



    3:35 - Ozzie’s family values: hard work and education

    13:30 - The value of maturity and doing things on your own schedule

    16:50 - What you learn as an intrepid entrepreneur without a safety net

    20:00 - What you learn in the military: leadership, discipline, and the commitment to team

    35:30 - Leadership lessons from the military

    37:30 - Starting a business after 9/11

    49:50 - Developing a network to defeat a network

    54:30 - Why growth matters to you, your employees, and your customers

    56:40 - How to create a sense of ownership among your employees

    1:02:35 - What it’s like to build a family later in life

    1:12:10 - How the COVID crisis is driving innovation

    1:24:00 - There’s no place like the U.S.A.

    1:32:30 - Rob’s takeaways



    Connect with Gary Rabine and DDCEO:

    Visit the DDCEO BLOG: http://ditchdiggerceo.com/

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

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

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

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg/featured?view_as=subscriber

    • 1 hr 42 min
    #41 A Great Entrepreneur's Principals for Closing the Racial Income Gap w/ Robert Blackwell Jr, Founder of Quant16

    #41 A Great Entrepreneur's Principals for Closing the Racial Income Gap w/ Robert Blackwell Jr, Founder of Quant16

    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 (https://www.instagram.com/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.

    Robert Blackwell, Jr is the founder of Quant16 as well as a successful entrepreneur and former trader. He also founded Killerspin, the world’s leading table tennis engagement brand. The Killerspin experience reaches hundreds of thousands of people annually in over 160 countries around the world. Robert has served on many civic boards over the course of his career, and he currently serves the Chicagoland Chamber of Commerce, Civic Federation of Chicago, Business Leadership Council as well as being on the executive committee to Choose Chicago.  

    http://robertblackwelljr.com/ 

    https://www.linkedin.com/in/robert-blackwell-jr-4218023/  



    2:00 - How do people go from poverty to prosperity? 

    15:30 - The advantage of growing up without money 

    22:15 - Robert’s long-time friendship with former president Barack Obama 

    25:30 - Why Robert sold his car to use ride share services exclusively 

    26:30 - Robert’s life-changing visit to West Africa 

    34:30 - Learnings from the ‘87 market crash 

    45:30 - Robert’s formula for decision making 

    49:30 - Killerspin’s company values 

    52:30 - Investing in ongoing economic opportunities for those with special needs 

    54:00 - Lagniappe: a little something extra you weren’t expecting 

    56:30 - What’s next for Robert and Killerspin? 

    1:02:30 - Why you should have an innovation budget  

    1:08:30 - Quantitative analysis vs. quantum computing 

    1:18:35 - You can get mentorship by reading, listening, and watching 

    1:19:05 - Rob’s 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 26 min
    #40 Be Worth More Than You’re Paid w/ Dan Porcaro, Biz Strategy Expert

    #40 Be Worth More Than You’re Paid w/ Dan Porcaro, Biz Strategy Expert

    Daniel Porcaro has spent the past 33 years growing and developing four companies.  Growing companies is his passion.  Dan grew all the companies mostly through organic growth with very few acquisitions.  He is passionate about long-term revenue and profit growth through the development and execution of a strategic plan and the development of a strong culture.

    Currently, Dan is the Managing Partner of Porcaro Stolarek Mete Partners LLC (known as PSM Partners).  Founded in January of 2015, PSM offers IT consulting and talent acquisition services to small and mid-sized firms in the Chicago area.  As of January 2020, PSM employed 73 consultants and 300 clients.  Dan started the firm with his Partners and close friends Mike Mete and Dave Stolarek to grow PSM into the firm it is today.  PSM certainly would not have been nearly as successful without them.

    From 1998 through 2012, Dan founded and ran Project Leadership Associates (PLA).  PLA was a business and technology consulting firm headquartered in Chicago.  With five practice areas -network integration, managed services, software development, business intelligence, and business strategy, PLA was unique for its size.  Starting with one employee, Dan grew PLA to 265 people, 50 million in revenue, and 6 offices across the country.  PLA was one of the most profitable, successful firms of its type in the country.  PLA also had a ten-year period where voluntary turnover was less than 2%.  Additionally, Dan is proud to say that PLA never lost money in any month of its existence under his tenure.  Dan sold PLA in 2012 to a private equity firm.

    Prior to founding PLA, Dan was a partner in Workgroup Productivity Corporation (WPC).  WPC was a Lotus Notes consulting firm.  Dan was asked to join WPC as an equity partner to grow the firm, nationalize its services, and find a buyer.  He accomplished the growth plan over a 3- year period (growing revenues by 65%) and found a buyer for the firm.  After this transaction, Dan left to start PLA.

    Prior to WPC, Dan was an Executive Director and Partner at Lansystems.  Headquartered out of NY, Lansystems was a nationwide network integration firm with an east and west coast presence.  Dan started the central region for Lansystems and quickly grew it from 2 to 60 employees while becoming the most profitable region in the country for the firm.  Lansystems was sold in 1994.



    LinkedIn: https://www.linkedin.com/in/daniel-porcaro-8540391/ 

    Website: https://www.myefbc.com/board-staff/dan-porcaro/



    4:27 - What’s more important growing up: loving support or a strong entrepreneurial role model?  

    4:58 - Leadership: learned or innate?  

    11:47 - The importance of being well-rounded as a leader 

    17:21 - Learning from others’ mistakes 

    36:08 - What makes for a solid business strategy 

    45:03 - How to bake sales success into a company’s culture 

    49:16 - What really motivates employees (spoiler: it’s not the money) 

    1:02:55 The difference between growing a company you plan to sell vs. one you plan to keep 

    1:07:53 Can you pandemic-proof a business? 

    1:11:44 The positives of partnership 

    1:13:44 How culture interacts with earnings growth 1:15:36 Incubating new businesses 

    1:21:11 Rob’s take-aways



    Connect with Gary Rabine and DDCEO:  

    Visit the DDCEO BLOG: http://ditchdiggerceo.com/  

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

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

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

    Subscribe on YouTube: https://www.youtube.com/channel/UCh03Px5ez_xe_oE_iJMMNIg/featured?view_as=subscriber

    • 1 hr 27 min

Customer Reviews

5.0 out of 5
287 Ratings

287 Ratings

Savvyman2 ,

Birth Date-Death Date

Great podcast! Gary is a classy guy who has done a lot of wonderful things for the communities he works in and around!

mike custom truck ,

Listen and Learn

Great show!

Smitty60423 ,

Learn from the best

Having worked in the asphalt paving business for 10 years, I’ve followed Gary’s story. His work ethic and creative thinking is an inspiration to anyone who strives for success.

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