Gary Vee // discusses luck, depression and legacy

Gary Vaynerchuck or Gary Vee for his fans online – embodies the spirit of an entrepreneur.

From selling baseball cards & setting up lemonade stands as a kid, to eventually helping his family grow their liquor store into a $45mil business, Gary brings an incredible perspective on the business world that he shares in this interview.  

He now 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, including 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   In this conversation, we discuss his thoughts on luck in business, entrepreneurial depression and how he thinks about legacy.  

Five Things To Listen Out For

(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

Time Stamps

  • 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]

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