Gary ‘Vee’ Vaynerchuk was born to be an entrepreneur. At six years old, he was already running a lemonade stand like a boss, later flipping baseball cards for cash. By age 14, he had made thousands when his father put him to work in the family liquor store for $2 an hour. He hated it, but years later, he rebranded the business and scaled it from $4 million to $60 million. Realizing he didn’t own a piece of it, Gary walked away with nothing and started over. Now, as the founder of multiple ventures, including VaynerMedia, and an early investor in Facebook and Twitter, he knows that real failure isn’t losing, it’s never taking the shot. In this episode, Gary joins Ilana to break down the pressure, sacrifice, and resilience needed to win in business and life.

GaryVee is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. As a prolific investor, he made early bets on major tech giants, including Facebook and Twitter.

In this episode, Ilana and Gary will discuss:

(00:00) Introduction 

(02:24) Hardwired for Entrepreneurship As a Kid

(05:34) From the Soviet Union to the American Dream

(07:22) Why Building Wealth Doesn’t Guarantee Joy

(11:15) Getting Forced Into the Liquor Business at Age 14

(13:18) Scaling the Family Business from $4M to $60M

(17:14) Discovering the Internet and Betting Big on It

(21:10) The Power of Personal Branding

(26:13) Building Resilience Against Online Hate

(29:24) Why Gary Would Rather Fail Than Regret or Blame

(32:21) The Harsh Realities of Entrepreneurship

(39:49) Humility, Not Titles as the Key to Lasting Success

(43:27) Choosing Optimism Over Fear

GaryVee is a serial entrepreneur, chairman of VaynerX, CEO of VaynerMedia and VeeFriends, and a six-time New York Times bestselling author. He built his career by transforming his family’s liquor business from $4 million to $60 million before launching multiple ventures of his own. As a prolific investor, he made early bets on major tech giants, including Facebook and Twitter. Recognized as one of the most forward-thinking minds in business, culture, and the internet, Gary helps brands stay ahead by spotting trends early.

Connect with Gary:

Gary’s Website: garyvaynerchuk.com 

Gary’s LinkedIn: linkedin.com/in/garyvaynerchuk 

Gary’s Instagram: instagram.com/garyvee 

Resources Mentioned:

Gary’s Book, Crushing It!: How Great Entrepreneurs Build Their Business and Influence-and How You Can, Too: https://www.amazon.com/Crushing-Great-Entrepreneurs-Business-Influence/dp/0062674676 

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