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20VC: Gary Vaynerchuk on The Most Painful Lessons Learned but Why it was Good to Learn Them, Why You Have to Change the Timeframe You Have For Success, His Relationship to Money and How it Has Changed Over Time & His First 3 Angel Investments; Twitter, Fa

Jun 20, 2022

Gary Vaynerchuk, a serial entrepreneur and CEO of VaynerMedia, shares his transformative journey from running a $60M wine business to becoming a top angel investor in tech giants like Twitter and Facebook. He reflects on the painful yet valuable lessons learned throughout his career. Gary emphasizes the role of luck versus hard work and navigates through his insecurities and relationships, revealing how his father’s influence shapes his parenting. He also discusses the importance of long-term fulfillment over mere financial success.

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ANECDOTE

First Investments

Gary Vaynerchuk's first investments were Facebook, Twitter, and Tumblr.
These were acquired through personal connections and a belief in social media's potential.

INSIGHT

Luck vs. Hard Work

Luck plays a role in everyone's life, but hard work and positioning oneself for opportunities matters more.
Vaynerchuk emphasizes his diligence in saving and researching before investing.

ANECDOTE

Family Business Friction

Vaynerchuk's most difficult lesson came from friction with his father regarding compensation and equity in the family business.
Despite growing the business significantly, he faced resistance, leading to a trying period.

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Gary Vaynerchuk is a serial entrepreneur and serves as the Chairman of VaynerX, the CEO of VaynerMedia and the Creator & CEO of VeeFriends. Now Gary is a content machine and documents his life as a CEO daily through his social media channels which have more than 34 million followers and garnishes over 272 million monthly impressions/views across all platforms. He is also a five-time New York Times Best-Selling Author and is a prolific angel investor with early investments in companies such as Facebook, Twitter, Tumblr, Venmo, Snapchat, Coinbase and Uber. If this was not enough, Gary serves on the board of GymShark, MikMak, Bojangles Restaurants, and Pencils of Promise.

In Today’s Episode with Gary Vaynerchuk We Discuss:

1.) From Wine Library to One of The Great Angels in Tech:

How did Gary make the transition from scaling the wine library to $60M in revenue to angel investing in Twitter, Facebook and Tumblr?
To what extent does Gary think luck plays a role in one's success today?
What are Gary's biggest lessons from having FB, Twitter and Tumblr as his first investments? How has his style of angel investing changed over time?

2.) Hard Lessons Learned and Insecurity:

What is the most painful lesson Gary has learned that he is also pleased to have learned?
How did Gary's relationship with his father impact how he engages with his children as a father today?
What are Gary's biggest insecurities today? How does he try and combat them? What works?

3.) Money and Success:

How does Gary evaluate his relationship with money today? How has it changed over time?
Why does Gary believe that most people think too short-term? What can one do to inspire a more long-term mindset to building?
Does Gary believe that everything has a price? What is the one thing for Gary that does not have a price?

4.) Resource and Time Allocation:

How does Gary determine the projects to do vs not to do?
How does Gary know when to quit a new project? How does Gary advise founders on when something is not working and knowing when to quit?
What are some of the biggest mistakes Gary sees founders make when it comes to resource allocation in the early days?