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Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899

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. ---------------------------------- Timestamps: 0:00 How did you get into investing and tech? 4:01 How much of a role does Luck play? 7:35 What's the most difficult but valuable lesson you've learned? 13:54 What is your greatest insecurity? 16:29 Has your fearlessness ever gotten you into trouble? 17:00 Public Gary vs. Private Gary 19:24 How do you manage your ego? 22:00 How to deal with the haters 24:51 How to balance work and family 27:24 How do you know when to give up? 30:33 What have you recently changed your mind on? 31:05 What is your greatest accomplishment? 31:20 Where do you want to be in five years? ---------------------------------- 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? ---------------------------------- #GaryVaynerchuk #HarryStebbings #20VC #GaryVee #VaynerMedia #angelinvestor #venturecapital #businessadvice #internethistory #business #WineLibrary #investing

Harry StebbingshostGary Vaynerchukguest
Jun 19, 202232mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Gary Vee on Luck, Sacrifice, Self-Belief, and Angel Investing Origins

  1. Gary Vaynerchuk recounts how he stumbled into angel investing in his early 30s, turning personal relationships and deep conviction in social media into early bets on Twitter, Facebook, and Tumblr.
  2. He frames his career as a blend of extreme luck and deliberate effort, emphasizing long-term thinking, saving aggressively, and then going “all in” when conviction is high.
  3. Gary dives into difficult family dynamics from scaling his father's liquor business without ownership, and how that experience shaped his views on money, happiness, and valuing relationships above financial upside.
  4. He also explores ego, self-doubt, online hate, and the importance of self-esteem, explaining why he treats business as his true hobby and why changing your mind—like he did on Facebook’s importance—is a strength.

IDEAS WORTH REMEMBERING

5 ideas

Leverage conviction and relationships to make asymmetric early bets.

Gary’s first three angel investments—Twitter, Facebook, Tumblr—came from deep belief in social media’s future and genuine friendships with founders and early employees, not from chasing hot deals or having large amounts of capital.

Treat luck as real, but still maximize what you control.

He credits geopolitical chance (escaping the USSR as a child) as foundational luck, while arguing that saving aggressively, staying curious, and showing up to events created the conditions for his big wins.

Prioritize relationships and happiness over perfect financial fairness.

The painful misalignment with his father over equity and pay taught him to choose being the “bigger man” and preserve family over money, while quietly building his own independent path with VaynerMedia.

Anchor your ambition to a lifetime horizon, not monthly results.

Gary doesn’t worry about “losing an inch” by taking time for family or rest because he evaluates his success over a 70–90 year life, not by weeks, quarters, or even a single decade.

Use humility and empathy to process criticism and hate.

He suggests first asking if any criticism is true, then recognizing that people who spew hate are usually deeply unhappy, which helps depersonalize attacks and stay grounded in positivity.

WORDS WORTH SAVING

5 quotes

Everybody is lucky and nobody's lucky. It just depends on deciding what you want to say and do.

— Gary Vaynerchuk

I knew that I was happy at 25 making $48,000 a year, buying nothing, so I could be happy forever, so who gives a fuck?

— Gary Vaynerchuk

All that money and fame do is expose who you actually are. It just accelerates your truth.

— Gary Vaynerchuk

I'm almost using business as a disguise to try to help people be happier.

— Gary Vaynerchuk

For me, the number one thing I like more than anything in the world is being an entrepreneur.

— Gary Vaynerchuk

Gary’s entry into tech and early angel investments in Twitter, Facebook, and TumblrThe role of luck versus hard work and deliberate strategy in successFamily business conflict, sacrifice in his 20s, and lessons from working for his fatherSelf-esteem, dealing with hate, and separating ego from external validationBalancing extreme ambition with family and personal life through long-term time horizonsAuthenticity between public and private personas and managing fameChanging his mind on Facebook as a content platform and evolving content strategy

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