Philanthropy
Laughter has the power to heal and together, we can make the world a little brighter.
Bringing Joy Where It Hurts the Most
Win Win Charity’s goal is to bring smiles to children in hospitals by arranging visits and programs from professional entertainers, athletes, and celebrities.
Tim currently sits on the board of directors for Win Win Charity. Currently operating in more than 20 cities, this nonprofit is 100% volunteer-based.
Before I ever performed in a children’s hospital, I was handed a list of things I wasn’t allowed to say.
No “How are you?”
No “I hope you get better.”
Because in places where it’s terminal, those words don’t make it better.
That moment reshaped how I see my work and what success actually means. It led me into years of hospital visits, virtual programming during COVID, and deeper involvement with Win-Win Charity.
I shared the full story: from Vegas stages (success on paper) to the hospital room that changed what real success looks like, on the blog.
Win Win Telethon - 2025
Win-Win Charity’s annual Telethon brings together entertainers, hospitals, and supporters for one night that turns generosity into real impact for children nationwide.
Through simple donations, sponsor support, and the Adopt-A-Hospital program, the Telethon helps ensure our services remain free and consistently available to children’s hospitals all year long.
It is the little moments
Entertainer of the Year
Win Win Charity - 2025
In 2025, Win Win Charity named me Entertainer of the Year.
I’m deeply grateful for the recognition, not because of the title, but because of what it represents:
years of showing up consistently, serving families, and supporting the mission of bringing joy into places where it’s needed most.
This work exists because people decide it matters. Thank you for being one of them.
Adopt a Hospital
Adopt a Hospital is the most direct way to make this work possible.
Adopt a Hospital is one of the most direct ways organizations can create real, measurable impact.
Through Win-Win Charity, a company or organization can adopt a children’s hospital—either in their own community or one they choose—and help fund ongoing entertainment, experiences, and moments of relief for kids and families who need it most.
This isn’t a one-time gesture.
It’s sustained support that shows up again and again inside hospital walls—turning ordinary days into moments that matter.
If your organization is looking for a meaningful way to invest in its community (or extend its impact beyond it), adopting a hospital is a powerful place to start.
Learn more about adopting a hospital:
And if you want to support this work right now, donations help make hospital programs possible and keep this mission moving forward.
Entertainment in Hospitals
The Kid’s Clubhouse Show staring The Dude, is on a mission to bring joy, entertainment, and a sense of normalcy to children facing illness or health crises in Children’s Minnesota hospitals. It is a direct affiliation with the Win Win Charity.
By providing interactive shows, games, and a platform that celebrates the unique light within each child, their goal is to create moments of laughter, silliness, and connection that help kids and their families navigate challenging times with positivity and hope.
Magic and a prom to remember
A Night To Remember Prom is on a mission is to celebrate teens and young adults with special needs by providing them with an unforgettable prom experience in a safe, welcoming, and inclusive environment. By pairing Honored Guests with peer Student Hosts, ANTR fosters joy, connection, and lasting memories, all while ensuring each guest feels valued, celebrated, and loved.
Tim performed every year for over a decade in support of this special night.
Stay connected to the Good
Moments like these don’t happen once.
They happen because people stay connected.
If you’d like more reminders, stories, and small mindset resets that make today better, you’re invited to follow along
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