From Humble Beginnings to Podcast Success: The Journey of Collaboration and Growth

This chapter explores the journey of transforming a podcast concept into a successful business, detailing early challenges like guest sourcing and financial management. It emphasizes collaboration and strategic partnerships as crucial elements in driving growth and sustainability.

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In this gripping Part 2 episode, Chris Do goes deep with Simon Squibb on the business model that powers his viral mission of giving away money to strangers. But this isn’t charity—it’s strategy. Simon unpacks how he built a profitable, self-sustaining content engine that funds dreams, spreads hope, and disrupts the traditional education system.

From revenue breakdowns across YouTube, TikTok, Instagram, and brand deals to his "infinite giving" philosophy, Simon shows that you can do good and make money—at scale. This episode is a masterclass in purpose-driven entrepreneurship, and a behind-the-scenes look at how generosity can become a business advantage.

Timestamps:

(00:00) - Why Simon’s mission seems crazy—but works

(01:30) - Giving strangers cash on the street… how? why?

(03:00) - The psychology behind belief, opportunity, and self-worth

(04:00) - Why school failed him—and how he’s replacing it

(06:00) - “Fun-education”: content that teaches people to start with $0

(08:30) - You don’t need money to start a business—here’s proof

(10:00) - How Simon’s videos spark action worldwide

(12:00) - Giving without expectation vs. manipulation

(14:00) - The business of giving: profitable, scalable, repeatable

(16:00) - Acting like you have no money (even when you do)

(18:00) - The flaw in traditional charities—and how Simon avoids it