In this episode of the World Class Podcast, Chris Vasquez sits down with legendary solo venture capitalist Oren Zeev, founder of Zeev Ventures. With a one-man fund that has consistently outperformed the biggest firms in Silicon Valley, Oren shares deep insights on how to think like a world-class investor, the mindset founders need to build generational companies, and why being contrarian is often the key to winning.

We dive into his origin story, his investing philosophy, and how he made early bets on companies like Chegg, Audible, Houzz, and Next Insurance. Oren also unpacks the unique traits of Israeli entrepreneurs, decentralized decision-making, and why America needs more radical meritocracy.

This conversation is packed with tactical wisdom and timeless frameworks for anyone building, investing, or simply looking to think more clearly and act more courageously in a noisy world.

In this powerful episode of the World Class Podcast, Chris Vasquez sits down with Andrew D’Souza, the co-founder and former CEO of Clearco, one of the most successful fintech startups of the last decade, valued at over $2 billion. After scaling Clearco to massive heights and transforming how startups access capital, Andrew made the bold decision to step away from the company he built — not to retire, but to chase a new dream.

Andrew opens up about the emotional and mental toll of running a hyper-growth startup, the identity crisis that often comes with success, and the deeply personal journey of walking away from a billion-dollar company to pursue something even more aligned with his values and purpose. Today, he’s building Boardy AI — an entirely new kind of product — and redefining what it means to be a founder.

In This Episode, You’ll Learn:

• Why Andrew left a $2B company at the height of its success

• The hidden emotional cost of startup success and how to navigate burnout

• How to rediscover your purpose when your identity is tied to your business

• The future of AI, entrepreneurship, and building for fulfillment over fame

• What Andrew is building next with Boardy AI and why it matters

This is not your typical founder success story — it’s a rare and honest conversation about ambition, purpose, mental health, and reinvention at the highest level. Whether you’re building a business, transitioning to a new chapter in life, or seeking deeper meaning in your work, this episode will resonate on a human level.

In this episode of the World Class Podcast, Chris Vasquez sits down with Jim McKelvey, the co-founder of Square (now Block), to discuss how he and Jack Dorsey built a $50 billion+ company that revolutionized digital payments. Jim shares the inside story of how Square took on—and ultimately beat—Amazon, the challenges they faced in scaling the company, and the innovation mindset required to disrupt an industry.

Jim is not only a successful entrepreneur but also an inventor, artist, and author of The Innovation Stack, where he breaks down the principles behind creating groundbreaking businesses. In this conversation, he reveals the key lessons he learned from building Square, the strategies that helped them outmaneuver one of the biggest companies in the world, and how entrepreneurs can apply these insights to their own businesses.

What You’ll Learn in This Episode:

• The untold story of how Square defeated Amazon and survived an all-out attack

• The power of The Innovation Stack and how to create a business that can’t be copied

• Jim’s entrepreneurial journey and the mindset behind building billion-dollar companies

• The biggest challenges in scaling a fintech giant and how Square overcame them

• The future of digital payments, entrepreneurship, and innovation

This episode is packed with invaluable lessons from one of the greatest business minds of our time. Whether you’re an entrepreneur, an innovator, or just someone fascinated by stories of resilience and disruption, you won’t want to miss this conversation with Jim McKelvey.

In this episode of the World Class Podcast, Chris Vasquez sits down with Adam Wexler, the visionary Founder and Chairman of PrizePicks, one of the fastest-growing daily fantasy sports platforms in the world. Adam shares his journey of building PrizePicks from an idea into a market-leading company, navigating the challenges of entrepreneurship, and scaling a business in one of the most competitive industries.

Adam dives deep into the mindset required to build and sustain a high-growth company, revealing key lessons on leadership, resilience, and innovation. He also shares the behind-the-scenes story of how PrizePicks disrupted the fantasy sports space, how to create a product that keeps customers coming back, and what it takes to be a successful founder in today’s rapidly evolving business landscape.

What You’ll Learn in This Episode:

• The story behind PrizePicks and how Adam turned an idea into a thriving business

• The biggest challenges of scaling a company and how to overcome them

• How to create a winning culture and build a strong team

• The mindset and habits of successful entrepreneurs

• Lessons in product innovation and customer retention

• The future of daily fantasy sports and PrizePicks’ next big moves

Whether you’re an entrepreneur, a sports fan, or someone looking for insights on building a world-class company, this episode is packed with valuable lessons from one of the most dynamic leaders in the game. Tune in now to learn how Adam Wexler built PrizePicks into a powerhouse and what it takes to succeed in the competitive world of startups!

In today’s episode, we sit down with Peter Smith, the visionary CEO and co-founder of Blockchain.com, one of the world’s largest and most trusted cryptocurrency platforms. As a pioneer in the crypto space, Peter has seen firsthand how blockchain technology has transformed finance and reshaped how we think about money, security, and freedom.

In this in-depth conversation, we explore Peter’s unique perspective on the future of cryptocurrency and what’s coming next as the industry matures. Peter shares insights on how he scaled Blockchain.com into a billion-dollar platform, the biggest challenges facing crypto today, and how the global financial landscape is on the brink of revolutionary change. We also delve into Peter’s take on regulation, decentralization, and the massive potential of Web3.

If you’re interested in understanding the future of money, investing in blockchain, or learning how the crypto industry will impact everything from banking to everyday life, you won’t want to miss this episode. Tune in to gain valuable insights from one of crypto’s top leaders on how to navigate the opportunities and challenges ahead!

Peter Smith is co-founder and CEO of Blockchain.com — a Bitcoin block explorer service and cryptocurrency wallet provider. Peter Smith was born and raised in England and, before founding Blockchain, had been living, studying and working in the United States, Africa, Asia and Europe. Peter Smith’s Bitcoin involvement started with co-founding the startup Blockchain with Nicolas Cary in 2011. Under the leadership of Peter Smith, the Blockchain company has become a leader in the cryptocurrency and distributed ledger technology market. For some time, he was an active investor in the crypto industry. Peter has been featured in popular magazines, and he is frequently invited as an expert and speaker at various related conferences.

In this deeply moving episode, we sit down with Darren Prince, renowned sports and celebrity agent, and a global advocate for addiction recovery, who shares a raw and inspiring story of resilience.

Darren built a successful career representing some of the world’s most iconic figures, like Magic Johnson, Muhammed Ali, Hulk Hogan, and Dennis Rodman. But despite working at the top of his industry, he struggled with a profound sense of emptiness, constantly seeking approval and battling imposter syndrome.

Together, Darren and Chris open up about their vulnerable journeys, sharing personal stories from their childhoods, their battles with addiction, and how they each turned to drugs to cope with insecurities and feelings of inadequacy.

Darren reveals the pressures and challenges of working in a world of fame, where self-worth often depends on external validation. He talks about his journey to recovery, finding self-love, and the turning points that led him to true fulfillment beyond professional success.

Through candid moments and personal insights, this episode sheds light on the power of vulnerability, the importance of self-acceptance, and the strength it takes to overcome deep-seated fears. Join us for a conversation that’s as inspiring as it is real, offering valuable life lessons for anyone who’s struggled with self-worth, approval, or addiction.

In this episode of World Class with Chris Vasquez, we dive into the mind of one of Silicon Valley’s most influential entrepreneurs and investors, Keith Rabois. Keith, a founding member of PayPal and an early investor in companies like LinkedIn, Square, and Yelp, shares his profound insights on scaling world-class companies, leadership, and what it takes to succeed in the fast-paced world of startups.

Throughout this conversation, Keith opens up about his decision-making frameworks, operating fast-growing startups, and hiring the right executives. He discusses why talented salespeople sometimes flop as VPs, the importance of knowing when to delegate versus doing things yourself, and how to manage time effectively as a leader. Keith also reveals his personal motivation, including how proving people wrong has fueled his incredible drive.

In a deep dive into current events, Keith shares his thoughts on the Kamala vs. Trump dilemma and explains why he believes the upcoming election could result in a massive win for Trump—providing a candid perspective on the political landscape and what’s at stake for the country’s future.

Chapters:

1:25 Founder Mode Explained

4:06 Why Sometimes Talented Salespeople Flop as VPs

4:57 Delegate vs Doing Yourself

9:00 Scaling Fast-Growing Startups

14:42 Key Executive Hires

16:20 Hiring Mistakes

17:25 Time Management Hacks

31:03 The Kamala vs Trump Dilemma

47:54 World Class Life

Key topics in this episode include:

• Founder Mode Explained: Keith’s approach to leadership and thriving in a startup environment

• Why Talented Salespeople Flop as VPs: The mismatch of skills at the executive level

• Delegate vs Doing: When to delegate and when to take charge yourself

• Scaling Fast-Growing Startups: Strategies for rapid growth in the tech industry

• Decision Frameworks & SOPs: Keith’s structured approach to running a business

• Investment Decision-Making Model: Keith’s method for evaluating high-potential investments • Key Executive Hires & Hiring Mistakes: How to build an effective executive team and common pitfalls to avoid

• Motivation & Success: Keith’s insights on what drives him, and using negativity as fuel for growth

• Time Management Hacks: How to manage your time as a startup leader

• The Kamala vs Trump Dilemma: Keith’s perspective on the 2024 election and why he thinks Trump will come out on top

• The World Class Life: Insights into what it takes to live at the highest level of success

• Growth Philosophy: Keith’s personal approach to growing businesses and people

In this insightful episode of “World Class with Chris Vasquez,” Chris is joined by Ed Sim, the #1 seed investor in the world, to share his invaluable lessons from 28+ years of venture capital investing.

We cover the best startup funding lessons from 28+ years of investing and the exciting world of AI & VC trends in the next 12 months.

Ed breaks down his approach to “inception investing,” diving into his unique 5 Ps model for evaluating startups and why starting small with your investments can lead to big payoffs. He shares his philosophy on the importance of having three founders, a concept honed over decades of successful investments. You’ll also hear about “The Weekend Test,” Ed’s method for evaluating founders’ true dedication.

As the venture space continues to evolve, Ed discusses the biggest shifts in the industry and how they’re shaping the future of startups. He takes a deep dive into the current AI investment landscape and shares stories of successful startups, including Parker Conrad and the rise of Snyk.

For founders, this episode is packed with advice on how to market the vision of your startup, when to deploy more capital, and why the first round of funding is so critical. Ed also talks about the ins and outs of launching a VC fund, and the importance of having “skin in the game,” especially as an underdog in the world of venture capital.

Ed’s journey is one of resilience and determination, and he shares his mantra of staying “poor, hungry, and determined,” a mindset that has guided him through decades of success in investing.

If you’re interested in venture capital, the future of AI, or want to know how to navigate the startup world from a master investor’s perspective, this episode is for you. Tune in for a wealth of knowledge from one of the most successful seed investors in the world.