“What is Your Relationship to Money?” with Chris Sacca, Chamath Palihapitiya, Gary Vee, Brad Gerstner, and more | 20VC Podcast with Harry Stebbings

Key Takeaways

  • Interviewing some of the world’s richest married couples
    • When it was clear that Chris Sacca and his wife were going to make some money, they sat down and talked with a bunch of people who have been through the same process
    • Chris got the idea from Evan “Ev” Clark Williams (@ev), an American billionaire entrepreneur
  • Investing is an infinite game, and the only real competitor is yourself
    • You are not fighting market gyrations, you are fighting your psychology
  • Trying to win the “infinite game” – the only marker of success is survival
    • If you get to the end of your life and you are still in the game, you won by definition, and it doesn’t matter how much you lost because you never quit the game
    • A lot of people treat investing like the opposite, a finite game where they are trying to sum up something (your worth, assets, etc.)
  • “The financial markets are a beautiful test of your ability to self-actualize and to psychologically evolve and survive and to build true emotional resilience.”Chamath Palihapitiya
  • Cyan Banister doesn’t have a lot of liquidity available to her all the time
    • A lot of her investment style is evergreen. She is wealthy on paper, but often cash-poor because she re-deploys most of her money back into the ecosystem
    • Anytime she has an exit is a celebratory moment because more startups are going to flourish and she has a new chance at it again
  • “All that money and fame do is exposes who you actually are. It just accelerates your truth.”Gary Vee
  • Rich people like to hang out with rich people?
    • People in the same economic zone have little interest to go after your money

Intro

  • How does money change a person? In this compilation episode, we have entrepreneur extraordinaires like Chris Sacca (@sacca), Brad Gerstner (@altcap) and Gary Vee (@garyvee) talk about how their relationship to money changed over time, and the wisdom and lessons they treasure from that experience
  • Who else is on this episode?
    • Chamath Palihapitiya (@chamath) is Founder & CEO of Social Capital
    • Cyan Banister (@cyantist) is one of the most impressive early-stage investors (SpaceX, Uber, Affirm, etc.)
    • George Zachary (@georgezachary) is a General Partner at CRV
    • Biz Stone (@biz) is the Co-Founder of Twitter and Medium
  • Host: Harry Stebbings (@HarryStebbings)

How Did Gaining Wealth Change Chris Sacca’s Relationship and Marriage?

  • Chris is lucky not to feel competitive with other investors and rich people
    • A lot of his friends are tortured by it; “…they have countless dollars at hand but feel like the goal line is always moving and they need to keep up with somebody else.”Chris Sacca
    • Key mindset: what can I do with the money we have?
  • In the beginning, when he made a lot of money, he and his wife bought multiple houses and became prisoners to their property
    • When anything broke, it was their responsibility
    • You can live luxuriously and not have to own the places. Rent and walk away when you are done
  • Interviewing some of the world’s richest married couples
    • When it was clear they were going to make some money, they sat down and talked with a bunch of people who have been through the same process
    • Chris got the idea from Evan “Ev” Clark Williams (@ev), an American billionaire entrepreneur

Chamath Palihapitiya and the Mindset of “Infinite Games”

  • Investing is an infinite game, and the only real competitor is yourself
    • You are not fighting market gyrations, you are fighting your psychology
    • There will be times when you will sell when you should’ve held and give up on opportunities to make money
    • Better handle of your emotions, understanding loan, battling with doubts of inferiority, finding ways to constantly become a little more humble and calmer, kinder to yourself
  • Trying to win the “infinite game” – the only marker of success is survival
    • If you get to the end of your life and you are still in the game, you won by definition, and it doesn’t matter how much you have or how much you lost because you never lost the game
    • A lot of people treat investing like the opposite, a finite game where they are trying to sum up something (your worth, assets, etc.)
  • How does Chamath think about his relationship to risk today as a result?
    • “The financial markets are a beautiful test of your ability to self-actualize and to psychologically evolve and survive and to build true emotional resilience.”Chamath Palihapitiya
    • You can punish yourself, or learn to be kind. You have to be vulnerable and super-authentic. You don’t know all the answers
  • Taking Social Capital public
    • Different levels of risk and responsibility
    • Chamath got to a point where he is no longer his own worst enemy
    • Can you be comfortable with someone entrusting you with some portion of their capital for the rest of your lives?

How Does Brad Gerstner Embrace Essentialism With Wealth?

  • Currently, Brad’s priority is to raise two sons and assure they are humble and understand the burden of having things
    • Knowing how it is to climb up the mountain rather than being dropped out of a helicopter on top of the mountain
    • It’s not what you say to your kids, it’s what you do
    • He lives in a modest house even though he can afford a much bigger one
  • “I don’t have as many cashmere sweaters as Chamath, but I do enjoy having a good time.”Brad Gerstner

Why Cyan Banister used to hate money?  

  • She hated money and used to throw it on the floor
    • Can’t touch it but loves making money
    • The power of capitalism and the sense of well-being it gave her was incredibly transformative
  • She doesn’t have much liquidity available to her all the time
    • A lot of her investment style is evergreen. She is wealthy on paper, but often cash-poor because she re-deploys most of her money back into the ecosystem
    • Anytime she has an exit is a celebratory moment because more startups are going to flourish and she has a new chance at it again
    • She is not an analyst, she has hunches that things are going to go well and trusts the people who are building those things
  • Once you learn to trust your convictions, the bigger risks you can take

If You Think You Suck, Somebody Put That Into Your Head (Maybe Your Mom?)

  • “All that money and fame do is exposes who you actually are. It just accelerates your truth.”Gary Vee
  • Gary’s content is more like therapy than business – it’s all about self-esteem
    • Reconcile and remind that everybody else sucks too, why are you beating yourself up?
    • He uses business as a disguise to try to help people be happier
  • Gary’s mindset doesn’t come because he has money, he has money because he has the mindset he had when he was broke
    • His favorite thing in the world is being an entrepreneur; no work = death for Gary Vee

Why Does George Zachary Believe Rich People Like to Hang Out With Rich People?

  • Growing up, he never really had any money
    • No incredible things happen when he got more money
    • He was capable of buying a lot of things, but after buying them, the novelty wore off
  • His relationship with money also changed his relationship with people
    • When you make a lot of money, people treat you differently
    • George reminisces about people being attracted to him because of money, it felt weird and was a real negative aspect
  • Why does George believe rich people like to hang out with rich people?
    • He became scared of not knowing people’s intentions
    • Do they want to hang out with him because they are friendly or do they have other incentives?
    • People in the same economic zone have little interest to go after your money

What Does Biz Stone Mean When He Says, “Wealth Only Serves to Amplify the Person You Are?”

  • Whatever type of person you were before is then amplified 100 times over
  • Money can’t make you happy if you were not a happy person before
  • The goes for geography; moving to a different country doesn’t change your personality
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Notes By Dario

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