Philanthropy in Public: Why Posting Your Charity Work Matters More Than You Think 🎗️ E151
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this special charity-focused episode, Dan documents his experience running the 12th annual World's Largest Toy Drive live from Tampa, Florida. (00:18) Starting with just eight volunteers wrapping toys on the floor twelve years ago, the toy drive has now expanded to 10 cities over 17 days, reaching stadiums and major venues across the country. (27:45) Dan shares the operational details, financial strategies, and partnerships that make large-scale philanthropy possible while emphasizing how anyone can start their own charitable initiatives.
- Main themes include breaking the stigma around posting about charity on social media, leveraging business ecosystems for philanthropic impact, and proving that charity can be run efficiently like a high-performance business
Speakers
Dan Fleyshman
Dan is the youngest founder to take a company public at age 23 and now runs multiple businesses while hosting the Money Mondays podcast. He founded Trina's Kids Foundation twelve years ago, which has grown from a small local toy drive with eight volunteers to stadium-level events across multiple cities, demonstrating his ability to scale charitable operations efficiently.
Key Takeaways
Leverage Your Business Ecosystem for Maximum Charitable Impact
Dan demonstrates how to align all aspects of your professional network—vendors, clients, employees, partners, and investors—to amplify charitable efforts. (09:29) For example, he connected Everbowl (a restaurant chain he invested in) to provide food at the Dallas toy drive, while Stella Jets provided their airport hangar as the venue and hosted a celebrity gala. This creates a multiplier effect where each business relationship becomes a force multiplier for charitable impact rather than operating in isolation.
Post About Charity to Create Massive Butterfly Effects
Breaking the stigma that posting about charity is self-promotional, Dan shows how social media amplifies charitable impact exponentially. (12:57) His "Two Years Too Long" clothing donation campaign generated over 4,500 tagged posts in one week, creating tens of thousands of additional donations worldwide. The key is focusing on the cause rather than personal recognition—showcasing why you care about the charity and how others can help, not seeking praise for your contribution.
Start Small and Prove Efficiency to Attract Major Donors
Dan explains his strategy of building charitable operations efficiently at scale to demonstrate capability to major corporations and wealthy individuals. (36:07) Starting with just personal funding for the first decade, he's now proving that charitable work can be run like a high-performance business, hoping to attract support from companies like Walmart, Target, and billionaires like Elon Musk by demonstrating measurable, efficient results.
Remove All Friction from the Donation Process
Dan emphasizes accepting donations in every possible format—PayPal, Cash App, Venmo, wire transfer, and Bitcoin. (05:48) The principle is that you never want friction to prevent someone from contributing to your cause. This applies beyond just payment methods to making it easy for people to volunteer, donate items, or share on social media—every barrier removed increases participation.
Find Passion Through Personal Connection to the Cause
The most sustainable charitable efforts come from personal passion rooted in lived experience. (38:35) Dan suggests identifying what has impacted you, your family, or close friends directly—whether it's cancer, autism, homelessness, or another cause. This personal connection provides the emotional fuel needed to persist through the challenges of organizing charitable efforts, from low volunteer turnout to fundraising difficulties.
Statistics & Facts
- Sean Callagy donated 119,000 toys across 10 cities for this year's toy drive, building on his previous donation of 100,000 toys the year before. (05:29) This represents one of the largest single toy donations and demonstrates how individual major donors can create massive impact.
- The toy drive utilizes 24 semi trucks with 5,000 toys per truck from World Tech Toys, a company that does over $200 million in toy sales annually. (08:17) This partnership allows them to get toys that retail for $25-$60 for just $3-$8 wholesale prices.
- Over 4,000 people have been tagged on social media participating in the $100 Tipping Club campaign that started during the 2020 shutdown, and over 4,500 people tagged the "Two Years Too Long" clothing donation campaign in just one week. (15:19)
