Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899
Harry Stebbings (host), Gary Vaynerchuk (guest), Narrator
In this episode of The Twenty Minute VC, featuring Harry Stebbings and Gary Vaynerchuk, Gary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899 explores gary Vee on Luck, Sacrifice, Self-Belief, and Angel Investing Origins 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.
Gary Vee on Luck, Sacrifice, Self-Belief, and Angel Investing Origins
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.
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.
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.
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.
Key Takeaways
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.
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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.
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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.
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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.
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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.
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Authenticity scales; fame amplifies who you already are.
Gary insists he’s essentially the same person privately and publicly, arguing that money and fame don’t change you—they expose you—so working on your character and self-esteem is more critical than chasing external success.
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Be willing to change your mind when the data changes.
He recently reversed his stance on Facebook, becoming “obsessed” again as he realized supply–demand dynamics for attention had shifted post–iOS 14, demonstrating that adaptability is a key competitive advantage.
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Notable 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
Questions Answered in This Episode
How can someone without Gary’s early access or network practically replicate his approach to spotting and accessing great early-stage investments today?
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.
Get the full analysis with uListen AI
Where is the line between healthy sacrifice for family or career and unhealthy self-neglect, given Gary’s experience in his 20s?
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.
Get the full analysis with uListen AI
How can creators and founders systematically build the kind of self-esteem Gary talks about, especially when they’re starting from a place of negativity or trauma?
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.
Get the full analysis with uListen AI
If long-term thinking is key, what concrete practices help someone shift from short-term obsession (weeks, quarters) to a life-span time horizon?
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.
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What specific signals made Gary change his mind on Facebook content, and how can others recognize similar inflection points on emerging or declining platforms?
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Transcript Preview
(beeping sound) Three, two, one, zero. (dinging sound) You have now arrived at your destination. Gary, this is such a joy to do. As I said to you beforehand, uh, seven years, uh, of me, uh, waiting, but I'm so thrilled that you joined me. So thank you so much for joining me today.
Thanks for having me, Harry. Glad to be on the show.
Not at all. I would love to start, before we dive into the real meat, just set some context. How did you make your way into the world of investing and tech first, before we dive into the meat?
You know, I never knew about investing. I, you know, I was ... When did I invest in Twitter? 2007. Um, I was 32 years old the first time I made an investment. I had never really even heard about angel investing. The world was very different back in 2006. Now, it is common practice. Most kids think about being an investor. You have 13-year-olds, you know, on Robinhood and NFTs. And so I was 32, I'd never thought about it prior, but I got into social media, Web 2.0, and I started to go to things like South by Southwest and this and that. I didn't have a lot of money, um, because I was working in my dad's liquor store and not getting paid a lot and all the, you know, the stories I talk about of, like, building a big business but not getting a lot of dollars. So I didn't have a lot of money, so when I first heard, like, "They put 100,000 into this. This guy put a million into..." I was like, "I don't... That's not for me. I don't have that kind of money." Then I started realizing, like, oh, you could write a $25,000 check, this, that, and the other thing. And then one thing led to another and I became very friendly with, you know, the- the f- several people on the small 10, 15, 20 person Facebook team, including their founding CTO, Blaine Cook. I started becoming friendly with Kevin Rose, uh, who is the founder of Digg.com and who's now very big in Web3 with Moonbirds. I, um, I started getting in the mix. I started reading TechCrunch, um, and I was like, "Oh, man. There's, like, this whole world." And then Blaine Cook called me and said, "I'm leaving Twitter and I'm really not happy and want to just sell all my shares. Just want to wipe my hands of it."
(laughs)
"And- and I know that you're a big believer, Gary, and you've been really nice to me and I think you- you get it bigger than just the way the nerds and I see it. And would you like to buy some of my equity?" And I said, "Yes, sir." First, I spent like five minutes trying to talk him out of it, um, but then I bought it. So it was my first transaction ever. I had to find a law firm in New Jersey. Um, I found one. The junior guy that was ascending to partner was a man by the name of Mark Yudkin. He now is the COO and my general counsel of my whole world. So from the first-
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