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.
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