Being nice at all costs will do nothing but leave you with resentment at the end of the day, which is why today’s guest advocates for practical optimism and kind candor instead. In this inspiring episode of Betting on Yourself, we are joined by the inimitable Gary Vaynerchuk, a born entrepreneur, chairman of VaynerX, and CEO of VaynerMedia. Gary fills us in on his entrepreneurship journey, starting at the ripe age of six, and explains how betting on himself from a young age has continued to pay off throughout his life. We discover how he decides where to place his bets, how he handles criticism, and why he chooses to live his life in the “purple.” Gary also shares his take on the fine line between optimism and delusion and why he feels it’s dangerous to coddle your kids. Tune in to hear all this and more, including Gary’s top tips for creating authentic content and comporting yourself with kind candor!

Key Points From This Episode:

• What “betting on yourself” means to Gary Vaynerchuk.
• How betting on himself from a young age has paid off.
• Examples of how trusting his intuition has served him.
• How he draws on history to make decisions about where he places his bets.
• Why Gary considers NFTs to be a profound technology.
• How he handles criticism.
• Gary shares his most significant moments of betting on himself.
• His courage to be misunderstood and take judgment in his stride.
• Why he lives his life in the purple, politically speaking.
• The danger of over-coddling your kids.
• The fine line between optimism and delusion.
• The gift of parenting with practical optimism.
• Gary’s tips for creating authentic content.
• What success means to him at this stage of his life and career.
• The dangers of being nice at all costs.
• The value of kind candor.

Links Mentioned in Today’s Episode:

Gary Vaynerchuk
Gary Vaynerchuk on LinkedIn
Gary Vaynerchuk on Twitter
Gary Vaynerchuk on Instagram
VaynerX
Michael Redd
22 Ventures