20VC What are the World's Tech Leaders Running From Fear Insecurity Poverty What Drives the Best with Orlando Bravo, Bill Ackman, Dara Khosrowshahi, Parker Conrad, Tobi Luttke, Brian Armstrong and more

In this episode of 20 VC, host Harry Stebbings explores the theme of personal motivations and the concept of running from or towards something in life with a diverse group of successful individuals. Orlando Bravo discusses his fear of stagnation, while Brian Armstrong from Coinbase reflects on overcoming shyness and the shift from fear-driven motivation to joy. Parker Conrad from Rippling shares how adversity fueled his drive to rebuild, and Toby from Shopify speaks on the pursuit of self-improvement. Ariel Cohen from Navan emphasizes the importance of interest-driven learning, and Dara Khosrowshahi from Uber talks about family and collective success. The episode also includes insights from Tarek at Kaushi, Jamie Siminoff at Ring, Bill Ackman, and Martin Escobari at General Atlantic, each sharing their unique drivers and the psychological factors that have shaped their paths to success.

• Harry Stebbings introduces the theme of what individuals are running from, a popular question in his shows.
• The question reveals commonalities among the thoughts of various successful individuals.
• Harry's introduction sets the stage for insights from Orlando Bravo and Brian from Coinbase.

"Now, one of the favorite questions that people love in our shows is, if we're all a function of our past, what are you running from?"

This quote establishes the central theme of the discussion, which is about understanding the underlying motivations and fears that drive successful individuals in their careers and lives.

• Orlando Bravo discusses his fear of stagnation and being trapped.
• His upbringing in Puerto Rico contributed to his mindset of always seeking better opportunities elsewhere.
• The nature of private equity aligns well with his desire for movement and change.

"I'm always on the go. I never like to stay in the same place for too long... I really think I'm running from the fear of being trapped, the fear of being isolated."

Orlando Bravo's quote highlights his personal fear of stagnation and how his background and career in private equity reflect his need for constant change and avoidance of feeling trapped.

• Orlando Bravo felt his career was a failure in 1999 after high expectations post-graduation.
• His love for tennis and its strategies helped him stay in the game and look for opportunities to change the game.
• He has not felt a career plateau since because his job and industry have evolved over time.

"I felt that my career was a failure in 1999... And I'm a big tennis fan and I used to play tennis. Maybe it helped me fight to stay in the game, just stay in that match..."

Orlando Bravo draws a parallel between his approach to tennis and his career, emphasizing the importance of resilience and adaptability in overcoming perceived failures and avoiding stagnation.

• Brian from Coinbase shares that he started his career running from shyness and introversion.
• He had a deep fear of not achieving something important in his life, which drove him to succeed.
• Over time, the initial motivations of fear and anger gave way to finding joy and passion in building things with technology.

"I think a lot of people start off in their career running from something... I was always a shy and introverted kid... And then I think I had this deep fear about never doing something important in my life."

Brian's quote reveals his initial insecurities and the powerful fear of insignificance that fueled his ambition, highlighting the psychological aspects of entrepreneurship and personal growth.## Personal Motivation and Impact

• The speaker is driven by a desire to have a significant impact at scale.
• There is a sense of fulfillment in reaching large numbers of people, rather than smaller, individual interactions.
• The speaker reflects on their journey and the excitement of impacting millions.

"It makes me feel good to try to do things at scale that have an impact on the big meta problems of the world."

The quote highlights the speaker's ambition to address large-scale issues and the satisfaction derived from making a substantial impact on the world.

"For me, I don't get the same feeling unless I'm trying to do something at scale that has, like, a major impact on the world."

This quote emphasizes the speaker's personal need for large-scale impact to feel fulfilled, contrasting with those who find fulfillment in smaller-scale, personal interactions.

• The speaker struggles with celebrating achievements and is always looking ahead to the next goal.
• There is a continuous push for progress, often at the expense of taking time to appreciate current successes.
• The speaker acknowledges a deep sense of fulfillment from their work and progress over time.

"You get to 10 million users. But then... What about next quarter?"

Harry Stebbings points out the relentless pursuit of growth and the difficulty in taking a moment to enjoy success, implying a constant drive for more.

"I have definitely thought about that because I'm not somebody who's really good at celebrating."

Brian admits to not taking time to celebrate milestones, indicating a focus on the journey and ongoing work rather than specific achievements.

• The speaker finds work deeply fulfilling and is not content with extended periods of inactivity.
• Vacations are less enjoyable for the speaker compared to engaging in productive activities.
• The concept of work-life harmony is preferred over work-life balance, integrating enjoyment into work-related activities.

"Jeff Bezos had this term one time where he talked about, it's not work life balance, it's work life harmony."

Brian references Jeff Bezos's philosophy, suggesting that integrating work and personal enjoyment is more fulfilling than trying to balance them as separate entities.

"If you can make your career fun, you'll never work a day in your life."

This quote underlines the ideal of finding joy in one's career, which can negate the feeling of work being a chore.

• The speaker was motivated to prove themselves after being forced out of a previous position.
• There was a period of silence due to legal restrictions, which was particularly challenging.
• The drive to build a successful company became a way to communicate and overcome the past narrative.

"I sort of decided the only way I was going to be able to communicate about this to people in the tech community, to the world more broadly than that, was to build this specific company, try and make it into a really big 100 billion dollar outcome."

Parker Conrad discusses his motivation to build a new company as a means to share his story and prove his capabilities, highlighting the use of entrepreneurship as a form of expression and redemption.

"But for a long know, that was sort of what was getting me going in the morning."

Parker reveals that the drive to build his company and change the narrative was what motivated him daily, indicating a strong personal investment in his work as a source of purpose.

• Avoiding boredom and ignorance is a key motivator for the speaker.
• There is a strong desire to become the best version of oneself.
• Understanding the world accurately is crucial for making informed decisions.

"The work of life is really try to minimize the diff between that person and the one that actually showed up."

Toby at Shopify speaks about the lifelong journey of self-improvement and the philosophical goal of aligning one's actual self with their potential ideal self, framing life as a continuous effort to bridge that gap.

"Not understanding a thing feels almost amoral to me."

Toby expresses a moral imperative to understand and learn, suggesting that not using one's intellectual capacity is almost unethical, emphasizing the value placed on knowledge and comprehension.## Personal Growth and Self-Learning

• Individuals have different learning styles, with some preferring self-guided learning based on personal interests.
• The desire to learn is often fueled by genuine curiosity about a subject.
• School performance can be inconsistent, depending on whether the subject matter engages an individual's interest.

"I can learn stuff by myself, but I can only learn stuff that really interests me."

This quote illustrates the speaker's self-awareness of their learning preferences, emphasizing the importance of interest in the learning process.

"If it gets my interest, I would geek out and learn everything about it."

The speaker acknowledges that personal interest is a key motivator for in-depth learning and engagement with a subject.

• Traditional paths, such as immediate college enrollment, may not suit everyone.
• It's important to take time to understand personal interests before making significant life decisions.
• The development of technology, such as machine learning and AI, may render certain learned skills obsolete.

"My advice to them, don't even at age 18 have this pressure to go to college."

The speaker advises against the societal pressure to follow a conventional educational path, suggesting that self-discovery is more important.

"Don't take this too seriously."

This quote emphasizes the speaker's belief in a flexible approach to education and career planning, considering the rapid evolution of technology and job markets.

• There is a fear of becoming complacent and failing to innovate within a company.
• The speaker is motivated by the desire to avoid stagnation and to continue innovating.
• Mergers and acquisitions (M&A) are not seen as a substitute for genuine innovation.

"The one thing that scares me is that one day Navan will be that kind of a company, that the only way that you innovate is through M&A."

The speaker expresses concern about falling into a pattern where innovation is driven by market dynamics rather than original ideas.

• Family history and experiences can shape one's drive and ambition.
• Shared success and collective achievements are valued over individual accomplishments.
• The concept of worthiness is linked to the pursuit of excellence and diligent effort.

"For me, success is joint success. It's shared success."

This quote reflects the speaker's belief in the importance of family and teamwork in defining and achieving success.

"If I put in the work, then I'm worthy that day, and then the next day, I got to come back."

The speaker associates worthiness with consistent hard work and effort, rather than with end results or material success.

• Parental expectations and absence can create a strong drive for achievement.
• Striving for perfection and exceeding expectations can become ingrained from a young age.
• The pursuit of excellence is a continuous process, not a fixed state.

"She was very strict when it came to excellence... where is that 2%?"

The speaker recalls a parent's focus on what was lacking rather than what was achieved, instilling a relentless drive for improvement.

"That drive and that sort of need for 120 percent, that doesn't leave you."

This quote indicates that the pursuit of excellence is a lifelong trait, deeply rooted in childhood experiences.

• Childhood experiences, such as feeling socially unaccepted, can influence adult behavior and motivations.
• The desire to solve problems can be overwhelming, and learning to focus is crucial.
• Success is often linked to external validation and the perception of others.

"The hardest thing I had to learn was you can't solve every problem for everyone because then you do nothing."

The speaker discusses the challenge of learning to prioritize which problems to address in order to be effective.

"I always say I don't have an ego, but I certainly like people seeing me successful."

This quote highlights the human tendency to seek recognition and validation from others, even when claiming to be unaffected by ego.## Entrepreneurship and Reality Distortion

• Entrepreneurship often involves believing in a much larger and seemingly unattainable vision.
• The speaker's experience of changing schools and creating a new persona is likened to the entrepreneurial journey.
• Entrepreneurs sometimes need to project confidence and grand visions, even when they are in the early stages of their venture.

"A lot of entrepreneurship is like reality distortion. You have to believe in something that's much bigger and crazier than what can actually be accomplished when you're a kid and you're in that position."

This quote emphasizes the necessity for entrepreneurs to have an almost delusional belief in their vision to succeed, often requiring them to "distort" the current reality to push towards their goals.

• The speaker clarifies they are not running from anything but rather towards greater happiness and self-actualization.
• The speaker acknowledges the volatility in their career and personal life but maintains an underlying sense of happiness and optimism.
• The pursuit of happiness is linked to fulfillment, relationships, self-actualization, and achievements.

"I think I'm running toward things. Greater happiness, self actualization, great relationships, friendships."

This quote reflects the speaker's proactive approach to life, focusing on positive goals and aspirations rather than escaping negative situations.

• The speaker discusses the initial feeling of being out of place and the dumbest among peers upon arriving at Harvard.
• They recount the process of building self-confidence and eventually finding common ground with other students.
• The overwhelming experience at Harvard is acknowledged, along with the institution's efforts to ease the transition for new students.

"I had the feeling I was the dumbest of the 1600, the absolute dumbest."

This quote captures the speaker's initial self-doubt and the common experience of imposter syndrome among high-achieving individuals in prestigious environments.

• The speaker describes Bolivia as a place of limited possibilities and contrasts it with the limitless opportunities in the U.S. and at Harvard.
• The speaker's transition from Bolivia to Harvard is seen as a transformative journey.
• The desire to help other entrepreneurs and people globally access opportunities is highlighted.

"A stereo dreaming boy is claustrophobic in a world with limited opportunities and gets a little crack in the door in a world of limitless opportunities in the US, at Harvard."

This quote illustrates the speaker's personal transformation from feeling confined by limited opportunities to embracing the vast possibilities available in a new environment.

• The speaker initially wanted to attend Yale due to its ranking but was persuaded to choose Harvard.
• The lack of awareness about Harvard's prestige by the speaker's parents and their subsequent pride is discussed.
• The speaker humorously reflects on the arbitrary nature of choosing between top universities.

"I actually wanted to go to Yale. It was ranked number one in some ranking I had seen... And he convinced me. I had no idea I landed there. I was like, okay, fine, whatever."

This quote conveys the speaker's initial lack of familiarity with the prestige of Ivy League schools and the somewhat whimsical decision-making process that led to choosing Harvard.

• Coda is presented as a tool that helps the team run smoother and be more efficient.
• The platform allows for collaboration and centralization of data and notes, which is crucial for the podcast's research team.
• The promotion of Coda emphasizes the importance of efficiency and collaboration in project management.

"Coder allows your team to operate on the same information and collaborate in one place by putting data in one centralized location regardless of format, eliminating roadblocks that can really stop your team in their tracks."

This quote highlights the benefits of using Coda for team collaboration, emphasizing how centralizing information can streamline processes and boost productivity.

• Brex is described as an all-in-one financial stack for founders, enabling global operations.
• The platform offers a corporate card, business account, and bill pay with a global-first mindset.
• Brex is positioned as essential for startups at any growth stage due to its international payment capabilities and high limit offerings.

"Brex enables you to operate in more countries and currencies than any other provider, so you can pay vendors, run payroll, and make international payments faster."

This quote outlines the global financial capabilities provided by Brex, which are crucial for startups looking to scale and operate internationally.

• Angelist is recognized for its rapid product development and improvements for startups and fund managers.
• The platform offers services for cap table management, banking, fundraising, and support for venture funds.
• Angelist is portrayed as a comprehensive solution for startups and funds to scale efficiently.

"Angelist reduces the friction of cap table management, banking, and fundraising all in one place."

This quote emphasizes Angelist's role in simplifying various financial and administrative processes for startups and venture funds, positioning it as a central hub in the venture ecosystem.