Live Different Podcast

How AJ & Gary Vaynerchuk Built VaynerMedia, VaynerSports, & VaynerRSE with AJ Vaynerchuk

Matt Wilson
January 16, 2024

The Guest: AJ Vaynerchuk of VaynerSports

AJ Vaynerchuk is the co-founder of the athlete representation firm VaynerSports. He is also the former COO of VaynerMedia, a social-media-first digital agency, working with Fortune 500 brands like Budweiser, Chase Bank, and Pepsico. He is also a founding partner of the venture capital fund VaynerRSE.

Born into an entrepreneurial family, AJ Vaynerchuk started displaying a sense for business from a young age. AJ also serves on the board of the New York Chron's and Colitis Foundation, a non-profit, volunteer-driven organization dedicated to finding the cures for Crohn's Disease and ulcerative colitis, and to improving the quality of life of children and adults affected by these diseases.

AJ and I became friends in New York City through our tech football and basketball games. AJ is a fierce competitor and an athletic dude... it's no surprise to me that AJ would go onto co-found a sports agency and represent professional athletes.  VaynerSports offers both contract advising and marketing off the field. Sports and business are in AJ and Gary Vaynerchuks's blood.

Episode 116 of the Live Different Podcast:

AJ Vaynerchuk shares his experience growing VaynerMedia to an epic level of success and managing a company of several hundred employees with his brother Gary, his decision to leave VaynerMedia to focus on his health and start VaynerSports, and his struggles with Crohn's disease. AJ and I talk about how stressful life as an entrepreneur can be and the importance of diet in staying healthy and performing at your peak.

AJ discusses his thoughts on hiring and firing quickly, the most important aspects of company culture, and why he and Gary aren’t afraid to fail. Vaynermedia's growth to a $100M company in such an incredible short time led to some extreme HR challenges. I was fascinated with the onboarding process that AJ and Gary created. Firing people is not fun as an entrepreneur, but AJ is incredibly honest about the process. As compassionate as AJ is, he told me that he's never demoted anyone to save their job.

Vaynerchuk leaves listeners with the advice, “As long as you learn from a mistake or failure, it’s a win.”

Resources from @AJV




Crohn’s and Colitis Foundation

Reach out to AJ Vaynerchuk on Twitter or Instagram @AJV.

Get this episode of The Live Different Podcast with Matt Wilson and AJ Vaynerchuk on Apple Podcasts, Stitcher, Soundcloud, YouTube, or Spotify.

Matt Wilson
Matt Wilson is Co-founder of Under30Experiences and Author of The Millennial Travel Guidebook: Escape More, Spend Less, & Make Travel a Priority in Your Life. He is host of the Live Different Podcast, Millennial Travel Podcast, and formerly Co-founder of He is committed to helping people live more adventurous lives.


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