The Money Mondays, E151: "Philanthropy in Public: Why Posting Your Charity Work Matters More Than You Think"

Host: Dan Fleyshman | Release Date: December 8, 2025

Episode Overview

In this special episode, Dan Fleyshman, angel investor and founder of Trina’s Kids Foundation, delivers a passionate monologue on the importance of public philanthropy. Filming live from Tampa amidst the 12th annual World's Largest Toy Drive, Dan spotlights the transformative power of charitable giving—especially when it's shared on social media. He addresses stigmas associated with “posting” charity work, details the operational realities behind large-scale charity events, and offers a step-by-step look at running effective charity drives, all with the aim of inspiring listeners to take action.

Key Discussion Points & Insights

1. The Growth and Impact of Trina’s Kids Foundation

• Foundation Story & Scale

  • Began 12 years ago with 8 volunteers (00:01).
  • Expanded to multiple cities with thousands of toys distributed per event; now executing 10 toy drives in 10 cities over 17 days (00:34).
  • Massive growth credited to both dedication and public sharing: “Because we post about on social media, ...we've now grown it to stadiums and arenas.” (12:57).

• Personal Commitment

  • For the first decade, Dan self-funded drives—sometimes spending six figures or over a million dollars annually (05:40).
  • Other early drives didn’t seek donations; focus was on giving, not publicity.

2. The Butterfly Effect of Social Media in Charity

• Challenging the Stigma

  • Dan dispels the myth that posting about charity is self-serving: “Let me break that stupid stigma right this second.” (12:01)
  • Draws a parallel to his podcast’s mission of normalizing money discussions: “It’s rude to not talk about [money]...I’m gonna break the next stigma, which is posting social media about charity.” (12:18)

• Real-World Multiplication

  • The “butterfly effect” means that a single post can spur thousands to action globally (13:15, 15:18).
  • Notable examples:
    • The $100 Tipping Club: Over 4,000 documented instances worldwide, likely tens of thousands untracked (15:18).
    • “Two Years Too Long” clothing drive: 4,500 tags in the first week, millions potentially reached by ripple effect (16:50-18:35).

  “That is the butterfly effect. That is why I post on social media about charity so much. That is why you should consider posting about charities that you care about.”
  — Dan Fleyshman [15:31]

3. Mechanics: How to Build and Scale a Charity Event

• Finding and Leveraging Partnerships

  • Importance of reliable suppliers (World Tech Toys provides toys at bulk rates; Everbowl feeds families at events) (08:44, 09:51).
  • Critical value in securing robust local partners (venues, sponsors, local businesses).

• Best Practices for Organizers

  • Accept donations via all methods: “Make sure that you can accept funds in any different way, any different format. You don't want any friction...” (06:34)
  • Efficient setup: Toys sorted by age and gender, open selection for recipients, excess distributed to other local charities (20:07).
  • Tying in one’s full business ecosystem: “Everything in my life is being tied in together. There are good partners and good friends that are now throwing galas.” (10:20)
  • Showcase logistics to inspire potential organizers; offers practical insight for others who “could host a toy drive in your own city.” (05:18)

4. Emotional and Community Impact

• Building a Giving Culture

  • Charity is more than just money—it’s time, energy, and inspiration to others (04:43).
  • Engaging family, staff, and networks multiplies positive impact and fosters company/family loyalty and unity (05:00).
  • Bringing children and those who have always received into active giving fundamentally changes their perspective (32:10).

• Unforgettable Experiences

  • Recounting moments at venues like the Miami Heat Arena: “That is magical. That is a core memory for these children.” (29:21)
  • Joy and relief of families receiving gifts and relief from seasonal expenses—“I’m addicted to it. I will always do these toy drives. That’s my passion.” (29:46)

Notable Quotes & Memorable Moments

• On the Power of Public Philanthropy

  “When you post about charity, not like ‘hey, look at me,’ but, ‘hey, look at this cause that I care about’...the butterfly effect is proven.”
  — Dan Fleyshman [13:00]

• On Inspiring Others

  “Your help, your efforts can literally change the world. That’s why I post about charity so much.”
  — Dan Fleyshman [05:17]

• On Logistics and Scale

  “Twelve years ago, I was on the floor with eight volunteers just wrapping toys on the floor. Now, Raiders Stadium, Big Night Live... BMO Stadium, a racetrack today in Tampa, Florida… Think about the venues we’re getting.”
  — Dan Fleyshman [24:15]

• On Making Charity Accessible

  “If you don’t have the money for it, the time and energy is fantastic. Showing up and volunteering is fantastic. Volunteering, your friends, your children, the people around you, your staff, get them to be a part of it because it changes their life.”
  — Dan Fleyshman [31:51]

• The Call to Action for All Listeners

  “I want the butterfly effect. I want someone that has a rich uncle, rich grandfather... Or they don’t even have to be rich, just have some money or some passion, some time, some energy to do more charity work.”
  — Dan Fleyshman [34:25]

Key Event Timeline (Timestamps refer to theme shift and key stories)

• [00:01 – 05:18]: Origin story of the toy drive, scale of the event, and personal commitment
• [05:18 – 10:20]: How to organize charity events: logistics, partner relationships, funding
• [10:20 – 12:01]: Leveraging business and personal networks, event collaborations, unique venue partnerships
• [12:01 – 16:35]: The importance of social media sharing, debunking public charity stigmas
• [16:35 – 19:45]: Examples of successful charity campaigns and their butterfly effect
• [19:45 – 24:15]: Detailed run-through of the 2025 toy drive’s city-by-city schedule and event specifics
• [24:15 – 29:02]: The emotional impact—children’s experiences at major venues, building lasting core memories
• [29:02 – 32:10]: The transformative effect of giving on families, volunteers, and communities
• [32:10 – 38:52]: Final thoughts: inspiring more people and organizations to embrace charity; personal vision for amplifying philanthropy
• [38:52 – End]: Encouragement for listeners to get involved, individually or with their network/family; key links and organizational call to action

Takeaways & Action Steps

• Charity Is For Everyone: Whether you offer money, time, or skills, every contribution can create exponential impact.
• Don’t Hide Your Good: Sharing your giving isn’t vanity—it inspires others, creates momentum, and directly increases real-world impact.
• Start Small, Scale with Passion: Initiatives that begin modestly can become city-wide or national with consistency, strategic partnerships, and visible storytelling.
• Be the Catalyst: “If you find something you care about, please get your children involved, your parents involved... Get them involved in charity and ultimately we can make the world a better place by pushing this along.” (38:52)

Resources & Connections

• World’s Largest Toy Drive Info & Donation: largesttoydrive.com
• Trina’s Kids Foundation: trinaskids.org
• Model Citizen Fund: modelcitizenfund.com
• Aspire Tour (Atlanta): Search “aspiretour.com” and use code ELEVATOR
• Follow Dan: Instagram @danfleyshman

Final Reflection

Dan closes by emphasizing that the ultimate goal isn’t just bigger toy drives or more donations—it’s culture change: making philanthropy “cool again,” visible, and accessible for everyone. This episode is both a practical how-to for charity organization and an energizing call to arms for the next wave of philanthropic leaders.

For the full schedule, resources, and updates, visit themoneymondays.com. Episodes drop every Monday at 4pm PST.