DiscoverThe Post Game Podcast#78 Rob Thompson: Building Opportunities in Sports Business, Entrepreneurship, and Serving the Cookies
#78 Rob Thompson: Building Opportunities in Sports Business, Entrepreneurship, and Serving the Cookies

#78 Rob Thompson: Building Opportunities in Sports Business, Entrepreneurship, and Serving the Cookies

Update: 2025-08-20
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Rob Thompson has had a unique career journey after playing college football at New Haven and a professionally overseas.

He built and sold a high school recruiting business, helped launch the NFL Flag program, was an Arena Football League GM, and started GamePlanU which has since rolled into Walter Camp Properties.

Not to mention, he is also a published author. Rob has lived at the intersection of sports, business, and innovation his entire career.

We discussed:

  • How dyslexia shaped his early years and helped him build resilience
  • Discovering new purpose after transitioning from sports
  • The inside story of launching NFL Flag and scaling a national program
  • What it's really like being a GM in the Arena Football League
  • Why college athletes should take more risks while they can
  • The two sides of NIL that most people completely miss
  • Why solopreneurship is the new internship
  • How "Aunt Dot" helped him master the art of networking
  • Why you shouldn't be afraid to "serve the cookies"
  • His contrarian take: skip the MBA—get a real estate license instead


Timestamps:

(0:00 ) - Intro to Rob

(2:20 ) - Rob's journey playing football

(6:20 ) - Creative roles in Corporate America

(8:10 ) - Re-discovering purpose after sports transition

(11:30 ) - The entrepreneur dilemma: holding onto a business vs. selling

(13:20 ) - Starting the NFL Flag program from scratch

(16:05 ) - Being the behind-the-scenes guy

(16:50 ) - Becoming an Arena Football League GM

(18:20 ) - Day-to-day reality of running a professional sports team

(22:05 ) - How college football perception affects your career

(22:20 ) - Just get a roster spot

(23:50 ) - The real NIL discussion nobody's having

(24:50 ) - Why college is the perfect time to take massive risks

(28:20 ) - Rob's podcasts over the years and lessons learned

(31:50 ) - Aunt Dot: the ultimate connector

(33:20 ) - Why warm leads beat cold outreach every time

(35:50 ) - "Serve the cookies" philosophy and how it lands major deals

(38:20 ) - Living in the moment while building for the future

(41:30 ) - GamePlanU & Walter Camp: building the next generation

(46:20 ) - Real estate as the path to financial freedom

(48:30 ) - Rob's best advice for college students


Links:

Connect with Rob on LinkedIn

Gridiron1880.com

GridIron1880 Instagram

Check out Rob's Book


The Post Game Podcast:

⁠Post Game Newsletter⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠LinkedIn⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠X.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Tik Tok⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Email me: joe.poduslenko@gmail.com

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#78 Rob Thompson: Building Opportunities in Sports Business, Entrepreneurship, and Serving the Cookies

#78 Rob Thompson: Building Opportunities in Sports Business, Entrepreneurship, and Serving the Cookies

Joe Poduslenko