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The Twenty Minute VCGary Vee: My First 3 Angel Investments; Why I Changed My Mind on Facebook Video | 20VC #899
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At a glance
WHAT IT’S REALLY ABOUT
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.
IDEAS WORTH REMEMBERING
5 ideasLeverage 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 quotesEverybody 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
High quality AI-generated summary created from speaker-labeled transcript.
