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.