595 Gary Vaynerchuk: Insecurity, Fame, and Crushing It in Business

Jan 29, 2018

Gary Vaynerchuk, a serial entrepreneur and CEO of VaynerMedia, dives deep into the world of authenticity and the changing landscape of entrepreneurship. He discusses how today’s teenage innovators are reshaping the business realm and why you need an independent partner for success. Gary shares valuable insights on the superficial lure of fame versus building a strong foundation. He emphasizes patience, the importance of genuine relationships, and the struggle with insecurities as key to lasting business success.

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INSIGHT

Entrepreneurship Became High-School Currency

Gary Vaynerchuk says entrepreneurship is now cool for teenagers and shifts social status dynamics in schools.
He notes verified social status (likes, blue checks) can drastically change social power for kids.

INSIGHT

Vanity Metrics Distract From Real KPIs

Gary warns chasing vanity metrics (lists, verification, likes) distracts from real KPIs like sales and impact.
He values product results and reach over editorial accolades or rankings.

ANECDOTE

Marriage Enabled Intense Entrepreneurship

Gary recounts being single-or-in-relationships but always prioritizing business from ages 15–27.
He credits his wife's independence for enabling his entrepreneurial drive and their divide-and-conquer home dynamic.

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NO ENTREPRENEUR CAN BE SUCCESSFUL WITH SOMEONE WHO ISN'T INDEPENDENT
As you know, it's important to continually grow (especially if you're an entrepreneur). I'm not excluded from that. Ten years ago I read a book by Gary Vaynerchuk that changed the course of my life.
On this episode of the School of Greatness, Gary returns to the show for his third time. He gives me advice for my next ten years but also gives you invaluable advice on so many topics that you won't hear anywhere else.
Gary is known for his unapologetic truth-telling attitude. He says a lot of things on social media that people may feel are harsh or extreme. But when we were talking, Gary revealed he actually cares deeply about what people think about him. And that's why he's so committed to serving people with hard-earned business wisdom in the long run.
He explains why teenage nerds are winning right now, how hitting the big lists isn't what matters in business, and why you need an independent person in a romantic relationship.
If you aren't familiar with Gary, you're missing out. Gary is a serial entrepreneur and the CEO and co-founder of VaynerMedia, a full-service digital agency servicing Fortune 500 clients.
Gary rose to prominence in the late 90's after establishing one of the first e-commerce wine sites, WineLibrary, helping his father grow the family business from 4 to 60MM in sales.
Gary is also one of the most sought-after public speakers alive today. He is a venture capitalist, 4-time New York Times bestselling author, and an early investor in companies such as Twitter, Tumblr, Venmo, and Uber.
You'll learn everything you need to know about how to become the best of the best, on Episode 595.
Some questions I ask:
How are you affected emotionally when you see yourself aging? (9:32)
Did business get better for you when you got married and started having kids? (16:52)
When you started having kids did your obsession for business stay the same? (22:31)
Why are you doing things you don't like when you have options not to? (24:51)
When are the moments that you doubt yourself the most? (26:09)
What's your insecurity? (33:45)
What do you think you need to take you to the next level? (38:00)
What advice would you have for me over the next 10 years? (51:52)
In the episode you will learn:
The results you should be concentrating on in business (14:02)
The biggest challenge Gary's faced since starting Vayner (23:13)
Best way to actually build your Instagram following (30:21)
Why Gary hates being disliked (34:20)
When relationships are really made (42:41)
Plus much more...

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