Just out of college, Gary grew his family wine business from a $4M to a $45M business in five years. Now, he runs VaynerMedia, one of the world’s hottest digital agencies with more than 800 employees and $100m in annual revenue. Along the way, Gary became a prolific investor. He’s investing in companies like Snapchat, Facebook, Twitter, Uber and Venmo.

He’s a 4x NY Times best selling author & recently starred in Apple’s original series: “Planet of the Apps”, with Gwyneth Paltrow, Jessica Alba and will.i.am.



(1) Childhood stories – before the lemonade stands, what Gary was like as a kid
(2) Luck – believing in luck, but wanting to eliminate excuses
(3) What matters most – if this was his last Thursday, how would he spend his last week?
(4) Depression – Gary discusses a recent suicide and why he thinks the culture of entrepreneurship being cool isn’t necessarily helping
(5) Legacy – how his view of legacy has changed over the last 10yrs
  • Gary shares some childhood stories [1m36s]
  • Before the lemonade stands [4m19s]
  • Trading attention [5m27s]
  • Thoughts on luck and eliminating excuses [6m9s]
  • “I take no credit for my success” [8m46s]
  • If this was his last week to live, what would Gary spend his time doing? [12m4s]
  • A reoccurring nightmare as a child [15m52s]
  • Entrepreneurial depression + suicide [17m27s]
  • Navigating self-doubt vs self-awareness to know you’re not doing the right thing [20m54s]
  • How Gary’s view of legacy has changed over the last 10 years [22m46s]
  • Building a business that lives on without you [25m56s]