In this special episode of Money Mondays, we hit pause on “how to make and invest money” and go all-in on the third pillar: how to give it away. Dan records live from Tampa in the middle of the 12th annual World’s Largest Toy Drive—a 10-city, 17-day marathon of giving that started 12 years ago with just eight volunteers wrapping toys on the floor.
You’ll hear how Trina’s Kids Foundation grew from a small local effort into stadium-level events at places like BMO Stadium, Allegiant/Raiders Stadium, American Dream Mall, and the Miami Heat Arena, powered by semi-trucks of toys, strategic partners, and a relentless focus on efficiency and impact. Dan breaks down the real numbers behind the toy drive, how he negotiates with suppliers to stretch every dollar, and why he’s obsessed with proving to major brands and billionaires that philanthropy can be run like a high-performance business.
But this episode isn’t just a highlight reel—it’s a playbook. Dan walks you through exactly how you can:
Host your own toy drive, food drive, or local fundraiser in your city
Use your business ecosystem—vendors, clients, employees, partners—to fuel charity work
Eliminate friction in donations (from PayPal and wire to Bitcoin)
Turn volunteering into a core part of your family or company culture
Use social media the right way so your posts about giving create a massive butterfly effect instead of looking like a humblebrag
You’ll also hear the origin stories of campaigns like the $100 Tipping Club and “Two Years Too Long” clothing drive, and how simple ideas—shared publicly—have inspired thousands of people around the world to copy and scale them.
If you’ve ever thought, “I want to do more, but I don’t know where to start,” this episode will give you the mindset, the mechanics, and the motivation to launch something of your own—whether you have money to donate or just time, energy, and a phone.