Gary Vee

Gary Vee

From Reclaiming with Monica Lewinsky by Wondery

June 9, 2026 · 1h 6m

About this episode

Gary Vee joins Monica Lewinsky for a candid conversation about his philosophies on success and entrepreneurship.

Serial entrepreneur and digital marketing icon, Gary Vee joins Monica on Reclaiming this week for a candid conversation that pulls back the curtain on his early investments in some of the biggest digital platforms of our time — including Facebook, Twitter, Venmo, and Resy, the wildly popular restaurant reservation app he co-founded. Though often seen as the patron saint of “hustle culture,” Gary reveals the counterintuitive philosophies that actually drive him: kindness as a competitive advantage, patience as the true engine of success, and radical accountability as the antidote to victimhood. Expect a raw, provocative, and surprisingly vulnerable conversation that goes far beyond marketing tactics — offering a masterclass in building a life, not just a business. Learn more about your ad choices. Visit podcastchoices.com/adchoices

People in this episode

Host: Monica Lewinsky

Guest: Gary Vee

Topics covered

  • entrepreneurship
  • digital marketing
  • hustle culture
  • kindness
  • success
  • accountability

Keywords

  • Gary Vee
  • entrepreneur
  • digital platforms
  • hustle culture
  • kindness
  • success
  • accountability

Mentioned in this episode

Organizations: Facebook, Twitter, Venmo, Resy

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