20VC Chris Sacca, Chamath Palihapitiya, Gary Vee, Brad Gerstner and more on Their Relationship To Money, How It Has Changed with Time and Wealth, How They Bring Up Their Children To Engender the Same Values of Ambition and Hard Work

In a thought-provoking discussion on the influence of wealth, prominent figures Chris Sacca, Brad Gerstner, Gary Vaynerchuk, Chamath Palihapitiya, Cyan Bannister, George Zachary, and Biz Stone share their personal experiences with money. They explore the psychological impact of affluence, the importance of maintaining humility despite success, and the amplification of one's innate characteristics when wealthy. The conversation delves into the practical aspects of wealth management, the potential for money to change personal relationships, and the varying approaches to risk and investment. Throughout the dialogue, a common theme emerges: money is a tool that can either enhance one's life or lead to greater complexity, heavily influenced by individual perspectives and choices.

• The relationship to money is a profound and complex subject.
• Money can change a person's life, behavior, and outlook.
• Understanding one's relationship with money is crucial for personal and financial growth.

"Those people look like money fucked them up. Let's go sit with them for a drink and ask them a lot of questions and get to the root of it."

• Chris Sacca expresses a desire to understand how money has negatively impacted certain individuals.
• The quote indicates a proactive approach to learning from the experiences of others who have had their lives complicated by wealth.

• Chris Sacca doesn't feel competitive with other wealthy individuals.
• He has experienced the burdens of managing multiple properties.
• Sacca values experiences over possessions, such as vacations without the need to own property.
• He and his wife, Crystal, have grown together with their wealth.
• They sought advice from other wealthy individuals, including those whose lives were negatively impacted by money.

"So I certainly look at it as, what can I do with the money we have? And luckily, we have all the stuff we want."

• Chris Sacca focuses on the utility of money rather than its accumulation.
• The quote reflects a contentment with what he and his wife have and a focus on using money purposefully.

"We sat down with a bunch of people who had been through that process. And by the way, not just the successful people, we intentionally sat down with people whose marriages had completely dissolved, whose lives looked like they had imploded, whose kids were assholes, and we sat down to get the counterexamples."

• Sacca and his wife actively sought out diverse perspectives on wealth, including negative outcomes.
• This quote indicates they were methodical in their approach to understanding the full spectrum of wealth's impact.

• Chamath Palihapitiya sees money as a tool, not the goal.
• Investing is an infinite game where the main competitor is oneself.
• Success in investing is defined by survival and the ability to manage one's psychology.
• Financial markets are seen as an opportunity for self-actualization and emotional resilience.

"The only real competitor is yourself, because the only thing you're really fighting is not really market gyrations, but it's your own psychology."

• Chamath Palihapitiya emphasizes the importance of self-awareness and psychological management in investing.
• This quote underscores the internal rather than external challenges of investing.

"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."

• Palihapitiya views the financial markets as a means to personal growth.
• The quote connects financial success with emotional intelligence and resilience.

• Harry Stebbings is the host and interviewer, engaging with guests about their relationship with money.
• He promotes various services and products, including Andopen, Angellist, and Squarespace, which offer ease and support for businesses and individuals.
• The promotions highlight tools that simplify complex processes for entrepreneurs and investors.

"Angellist has been a key partner for me in managing my investments."

• Harry Stebbings endorses Angellist for simplifying fund management.
• The quote serves as a personal testimony to the utility of the Angellist platform for investors.

"Squarespace is the all in one platform to build a beautiful online presence and run your business."

• Stebbings promotes Squarespace as a comprehensive solution for online business needs.
• This quote emphasizes the convenience and effectiveness of using Squarespace for digital marketing and web presence.

• Chris Sacca discusses his journey towards personal growth, emphasizing the importance of managing emotions and self-kindness.
• He mentions the challenges of dealing with feelings of inferiority and the conscious effort to become calmer, more humble, and focused.
• Sacca reflects on past decisions, like forgoing money-making opportunities or holding onto shares, and learning from those experiences.
• He highlights the importance of vulnerability and authenticity, acknowledging the lack of definitive answers.
• Sacca links his personal evolution to his professional evolution, suggesting that his growth has prepared him to responsibly manage others' capital.

"I find a way to just constantly become a little bit calmer, a little bit more humble, a little bit more focused, find a way to be kind to myself."

This quote encapsulates Sacca's commitment to self-improvement and the recognition that personal growth is a continuous process.

"It's been a great test. You have to be very vulnerable. You have to be super authentic. You don't know the answers."

Sacca acknowledges the challenges of personal growth, emphasizing the need for vulnerability and authenticity without having all the answers.

"But in this crazy way, Harry, it's also a professional evolution."

Sacca connects his personal development with his professional life, suggesting that the skills and insights gained from personal growth are beneficial in a professional context.

• Brad Gersner reflects on his past ambitions to make a million dollars by 30 and how his perspective on money has changed over time.
• Gersner describes the impact of his father's financial struggles on his own life and the drive to overcome financial insecurity.
• After achieving financial success through his ventures, Gersner's priorities shifted towards raising children with humility and an appreciation for hard work.
• Gersner emphasizes the importance of living by example for his children, choosing to live in a modest home despite his wealth.

"I have to make a million dollars by the time I'm 30. It was a dragon in my life because it destroyed our lives."

Gersner shares his early goal and the metaphorical "dragon" that represented his family's financial challenges and his determination to overcome them.

"My priority is to raise two sons that have humility, understand the burden of having things, and to know what it feels like to climb up the mountain rather than being dropped out of helicopter on top of the mountain."

This quote reflects Gersner's shift in priorities from financial success to imparting values of humility and effort to his children.

"It's not what you say to your kids... It's the life you live."

Gersner believes that actions and lifestyle choices are more influential than words in teaching children values.

• Cyan Bannister discusses her transformation from hating money to appreciating the power of capitalism and earning potential.
• Bannister shares her initial negative views on corporations and wealth accumulation, influenced by her personal circumstances and worldview.
• Her perspective changed as she entered the workforce and started her own business, gaining a sense of pride from financial independence.
• Despite her wealth, Bannister maintains an "evergreen" investment style, reinvesting her earnings into new ventures.

"I used to hate money, literally hate money."

Bannister candidly shares her past aversion to money and the emotional journey she underwent to change her perspective.

"I changed that mindset when I started my first job, and then also when I started my first business and when I started realizing the power of capitalism."

This quote captures Bannister's shift in attitude towards money as she began to recognize its potential for positive impact through capitalism.

"Even to this day, if I have change in my pocket, I have to get rid of it."

Bannister's quote reveals a lingering discomfort with physical money, despite her successful career as an investor and her enthusiasm for the financial success of the companies she invests in.

• Liquidity events are celebrated not for personal gain but for the potential to fund more startups.
• Exits provide an opportunity to reinvest and support the startup ecosystem.
• Lack of liquidity is common, even among successful individuals.

"But that's not necessarily true for everybody, including me. So anytime I have an exit, it's a celebratory moment, not for my own personal gain, but because that means that more startups are going to flourish and I have another chance at it again, if I were to fail over and over again, there goes my chances."

This quote highlights the importance of liquidity events in providing the means to continue investing in new startups and the cyclical nature of investment and reinvestment in the entrepreneurial space.

• Embraces significant risk for potential great rewards.
• Admires risk-averse investors for their analytical and quantitative abilities.
• Relies on qualitative analysis, pattern matching, gut instinct, and reading trends.
• Quick decision-making and high conviction can be uncomfortable for others.
• Not all strategies work for everyone; individual conviction is crucial.

"I take extraordinary risk and sometimes it makes people uncomfortable, but it often means that I'm the first check in, I'm sometimes the largest check, and I move very quickly, and that's how I win some of the deals that I win."

This quote underscores the speaker's aggressive investment strategy, which involves taking significant risks by moving quickly and often being the first or largest investor in a deal.

• Always trusted personal convictions, even before becoming an investor.
• Decisions are made quickly, sometimes perceived as impulsive.
• Willingness to reevaluate and adjust thinking when decisions prove wrong.
• High conviction is a vital trait for survival and success.

"I think I've always trusted my convictions, even before I was an investor and partially as a survivor, as someone who depends on making decisions, just literally to survive."

The speaker reflects on their history of trusting their instincts, which has been a fundamental aspect of their decision-making process throughout life, not just in investing.

• Money and fame amplify one's true self.
• Content creation is more about providing therapy than business advice.
• Promotes self-esteem and self-love as alternatives to external criticism.
• Belief in the mindset of happiness and success irrespective of money.
• Some things are priceless, such as the joy of working and being an entrepreneur.

"All that money and fame do, Harry, is exposes who you actually are. It just accelerates your truth."

This quote expresses the idea that wealth and recognition simply highlight one's authentic character and values, rather than changing them.

• Encourages self-love and questioning the source of negative self-perceptions.
• Happiness and mindset are not solely dependent on financial success.
• Entrepreneurship is equated with a passion that transcends monetary value.

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

The speaker suggests that their business advice is a vehicle for encouraging individuals to find happiness and self-worth beyond material success.

• Initial financial success can be anticlimactic.
• Novelty of purchasing items wears off after the initial excitement.
• Having enough money to support family can be fulfilling.
• The relationship to money may evolve over time.

"When I finally made enough money in the year 2000, I went from kind of zero to enough money that I didn't have to worry about money. And I have to tell you that it was pretty anticlimactic because all of a sudden, I thought, like, these incredible things would happen in my life, but they actually didn't."

This quote reflects on the speaker's personal experience with achieving financial security and the realization that it did not dramatically change their life in the ways they had anticipated.

• George Zachary experienced a shift in perspective about wealth, initially earning to potentially help others in emergencies.
• As his wealth grew, he noticed a change in how people, including extended family members he hadn't known, treated him.
• Wealth altered his relationships, with people seeing him as a form of power rather than as an individual.
• The change led to a negative aspect of wealth: people's intentions became unclear, and genuine relationships were harder to discern.
• George's wealth led to isolation as he became wary of others' motives and began to associate primarily with those in a similar economic bracket.
• This self-imposed isolation was a defense mechanism against the fear of being used for his wealth.

"And when I talked to people in my extended family about that, they thought it was great. But then I realized that I had a lot more members of my extended family that I had never known were in my extended family that seemed to have come out of the woodwork."

This quote reflects George's realization that his wealth attracted people, including distant family members, who may have had ulterior motives.

"It's not my issue that they have problems in their life... It's not my problem to help them continuously."

George expresses his frustration with the expectation that he should continuously solve others' financial issues due to his wealth.

"I actually became scared because I didn't know who to trust."

Wealth created a sense of fear and mistrust in George, making it difficult for him to discern genuine relationships from those seeking financial gain.

"I just started hanging out with people in approximately the same economic zone because I knew they had no interest in wanting to get any money."

George explains his choice to socialize with people of similar wealth to avoid the complications that come with disparate economic statuses.

• Biz Stone discusses the theory that wealth amplifies pre-existing personality traits.
• He suggests that wealth can lead to philanthropy for those who are naturally helpful, while for others, it may magnify negative traits like self-centeredness or greed.
• Biz Stone also touches on the stress of financial insecurity and how arguments over money can strain relationships.
• He notes that having excessive wealth doesn't necessarily lead to happiness, especially if one's personality isn't inclined towards contentment.
• Stone argues that geography doesn't change one's personality, and relocating won't solve underlying issues.

"You're not changed by great wealth, too much money. What happens is whatever the type of person you were before is then amplified, like 100 times over."

Biz Stone suggests that wealth doesn't change people but instead magnifies their existing characteristics, whether good or bad.

"If you're lucky and you get too much money, that's what happens to you. You get amplified who you are and maybe you're never happy because that wasn't the kind of person you were in the first place."

This quote emphasizes that happiness isn't guaranteed by wealth, and one's fundamental nature remains unchanged despite financial status.

• George Zachary notes that people in the venture business often socialize with one another, possibly due to understanding each other's motives and economic positions.
• He personally has few friends in the venture business, suggesting that even within similar economic zones, personal choices affect social circles.

"I also see this with people in the venture business. Like, I don't have many friends that I hang out with in the venture business here in Silicon Valley."

George's observation indicates that while economic similarity can influence socializing patterns, it's not the sole factor in his personal relationships within the industry.

• Harry Stebbings ends the episode with promotional content for various companies and platforms.
• He mentions Andopen, a company that simplifies corporate gifting, and Angellist, which aids in investment management and startup creation.
• Squarespace is highlighted for its website-building platform, emphasizing mobile optimization, email campaigns, and SEO tools.
• Promotional codes and URLs are provided for listeners to access services and discounts.

"Andopen helps companies of all sizes deliver better gifts, and they make it super easy."

Harry promotes Andopen's corporate gifting platform, emphasizing ease of use for businesses of all sizes.

"Angellist has been a key partner for me in managing my investments."

Harry shares his personal experience with Angellist, highlighting its utility in investment management.

"Squarespace is the all in one platform to build a beautiful online presence and run your business."

The quote summarizes the comprehensive services offered by Squarespace for building and managing an online business presence.