Gary Vaynerchuk | #AskGaryVee (Episode 494)

Gary Vaynerchuk | #AskGaryVee (Episode 494)

Gary Vaynerchuk (@garyvee) revisits The Art of Charm to talk about his new book #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awareness and answer questions from listeners and AoC alumni.

“Everybody old cares way more about how they made their money vs. how much they made.” -Gary Vaynerchuk

The Cheat Sheet:

  • With so many platforms at his disposal, why does Gary continue to write books?
  • Where does a workaholic like Gary stand on the concept of work/life balance?
  • When do we quit if something isn’t working?
  • How do you know if you’re hard-wired to be an entrepreneur?
  • How do we balance the hunger required to achieve Plan A while not taking too much comfort in Plan B?
  • And so much more…


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During his last visit to The Art of Charm, Gary Vaynerchuk was in the process of writing a new book. We talked about everything from the relentless pursuit of doing what we love to the tireless work ethic involved, and how he’s been on the go since he immigrated as a boy with his family to the United States from Soviet-era Belarus.

Now, Gary’s new book is out: #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awareness. In the spirit of its publication, we take the opportunity to ask him a lot of the questions that have come in from listeners and AoC alumni since his last time here.

More About This Show

Aside from his numerous other ventures, entrepreneur, author, podcaster, and former AoC guest Gary Vaynerchuk finds the time every three years or so to put out a new book — his newest yet is called #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awareness. But why does someone who makes himself heard across all channels of modern media go through the trouble of writing books in this day and age?

“[Some people] actually consume information much better in written book form,” says Gary, “and don’t want to watch a 20-minute video and don’t want to follow every social media person and click a link and read a medium. Their preference to consume information is in Kindle or print form when they’re traveling on vacation or before they go to sleep. This is…eating my own dog food of not being romantic about any platform.”

Going this extra step to make his efforts available to a wider audience also fits in with Gary’s famous work ethic — instilled in him by a life of hustling since arriving with his family as an immigrant from Soviet-era Belarus in the ’70s. Some might think a self-confessed workaholic would find a work/life balance between multiple endeavors and family time impossible, but he does — on his terms.

“I have no interest in telling people how to live their work/life balance,” says Gary. “I’m thrilled for anybody to critique mine, because I understand I put myself out there, so I deserve it. I have no interest in trying to defend against it. I just want everybody to know the only people that I’m going to respond to around this conversation are the 11 people in my most inner circle of my family who are the people that I most care about.”

Being his own boss makes all the difference. While he puts in 15-18 hours a day for hundreds of days a year, he’s still got more than a hundred days a year left where he can do whatever he likes — and he feels bad for the people who miss events in their kids’ lives because they have bosses who won’t give them the time off (but would still try to tell Gary he works too hard to truly devote time to his family).

When someone clocks in as many hours as Gary, there are bound to be missteps among the success stories. But how do you know when it’s time to give up on something you’ve been working toward? It’s by having an eye on your end game. “You have three business failures,” says Gary. “You’ve gone from a nice apartment to a worse apartment. Now you live in a rental studio. Now you live in a trailer. But then you build a 10 million dollar business? You’ve won. You’ve won in the 17-year period; you just happened to lose in a three-month, three-year, five-year period. It’s just about: how does it end?”

Listen to this episode of The Art of Charm to find out why Gary thinks more people will be listening to this podcast in 2031 than 2016, what happens when you understand yourself and deploy self-awareness, how to know if you’re wired to be an entrepreneur, why Gary loves meritocracy capitalism and marketplace dynamics more than he likes his own vested interest, how to ensure having a Plan B (and even a Plan C, etc.) won’t sabotage your Plan A, what parenting lessons Gary learned from his own upbringing and how he applies them to his own kids, what it means to play in the “white space” and how to find it, why Gary hopes to raise the bar with #AskGaryVee, why meditation isn’t for Gary, what differences exist between younger and older entrepreneurs, and why getting romantic about how you make your money is one of the best ways to go out of business.


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