From selling ACs to becoming the tourism king of Jamaica

I Asked a $450M VC Where to Invest in 2026

Mar 3, 202659 minSummary

In this episode of My First Million, the hosts interview a seasoned tech investor managing a $450 million fund to discuss investment philosophy, personal development, and the future of artificial intelligence. The conversation begins with a deep dive into the concept of asymmetric risk, where the investor explains that, unlike linear employment, successful investing is defined by high-upside opportunities where the downside is limited but the potential for growth is exponential. A significant portion of the discussion centers on the idea of building social capital, famously described as building your own yacht. The hosts analyze how hosting events or creating content generates inbound luck and social proof, serving as a powerful networking tool that bypasses traditional gatekeepers. Finally, the discussion turns to the rapidly evolving AI landscape. They explore the competitive dynamics between major players and the challenges facing vertical SaaS companies that risk being cannibalized by generalist models. The episode concludes with a creative look at how AI enables individuals to clone personalities for coaching, research, or content creation, emphasizing the potential for leveraging technology to scale expertise and influence in 2026 and beyond.

‘Think and Grow Rich’ Is a Lie. (But The Advice Still Works)

Feb 26, 202650 minSummary

In this episode of My First Million, the hosts explore the fascinating intersection of legendary self-help advice and the often-deceptive lives of the gurus behind it. The discussion centers on Napoleon Hill, the author of the iconic book Think and Grow Rich. While the book remains a classic staple in personal development, the hosts reveal that its widely cited origin story—that Hill was commissioned by Andrew Carnegie to interview the world’s most successful people—is almost entirely fabricated. They detail Hill’s history as a serial fraudster and con artist, yet they acknowledge that the book contains genuinely valuable, timeless principles like goal setting, persistence, and the importance of a mastermind group. Drawing parallels to modern figures like Jay Shetty, the hosts discuss the uncomfortable reality of separating art from the artist in the self-help industry. They debate whether a "broken past" invalidates a teacher’s message or if effective advice can stand on its own regardless of the messenger. Finally, they contrast these controversial figures with individuals they consider truly legitimate, highlighting the importance of authenticity and consistency in those who offer guidance.

Dumb iPhone Apps Are Making People Rich Again (Here’s how)

Feb 24, 202648 minSummary

In this episode, the hosts are joined by the founder of Starter Story to discuss the evolving landscape of digital entrepreneurship and the emerging opportunities for business growth. A significant portion of the conversation focuses on the surprising resurgence of iOS apps as a lucrative venture. While some might consider mobile apps a relic of the 2010s, the hosts highlight how the integration of AI-assisted coding and the viral discovery potential of platforms like TikTok have reopened the window for small, nimble teams to build successful applications. Examples include productivity and health-oriented apps that utilize creative gamification to solve specific user problems. The discussion shifts to the challenges businesses face regarding video production. The hosts observe that video has become the primary language of the internet, yet most companies lack a clear strategy or dedicated internal resources to produce effective, high-conversion content. They explore the idea of "done-for-you" video services as a massive B2B opportunity, where agencies specialize in single formats—such as man-on-the-street interviews or simulated podcast segments—to help brands navigate this complex landscape. The episode underscores the importance of rigorous pre-production, planning, and strategy in achieving digital success.

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