10 Years of Win-Win: Connect with the Heart of Nonprofit Fundraising
Every now and then, I stumble across a quote that perfectly resonates with my current chapter of life. Most recently, I read the words, “Great performance is never luck. It takes a lot of focus, heart, and hard work.” As my nonprofit organization, Win-Win Entertainment, prepares to celebrate its 10-year anniversary, these words have never felt more true.
Win-Win Entertainment is the product of countless sleepless nights, excruciatingly long days, and more phone calls, emails, and newsletters than I can count. Since our inception in 2011, I have poured all of my focus, heart, and hard work into this nonprofit, of which I am the founder and chairman. To date, I would never hesitate to call Win-Win my greatest performance yet.
I’m happy to announce that Win-Win Entertainment has no plans of slowing down any time soon! In fact, we’ve recently been able to bring more smiles to more children than we ever thought possible. Tag along as we take a stroll down memory lane to recount the evolution of Win-Win on the eve of its anniversary and reconnect with the heart of nonprofit fundraising.
What is the Heart of Win-Win Entertainment?
I speak about my national nonprofit organization, Win-Win Entertainment, quite often on this blog. Most recently, I detailed a Win-Win Entertainment visit over at Children’s Hospital Colorado before I served as professional emcee at Dykema’s Annual Definitive Conference in Denver. If you’re new here, or haven’t had the chance to check out my other blogs, let me fill you in about Win-Win.
Win-Win Entertainment is a 501(c)(3) classified national nonprofit headquartered in Las Vegas, Nevada. Our mission is to bring smiles to children in hospitals by arranging in-person and virtual visits from entertainers, celebrities, and athletes. We are 100% volunteer-based, meaning we have no paid staff—all performers, myself included, donate their time for all events.
Win-Win Entertainment currently operates in 12 cities, with charity programs across Nevada, Colorado, Texas, Tennessee, and more. We also produce virtual programs for children’s hospitals across the country, allowing us to bring our entertainers to countless children nationwide. Over 10 years, we have arranged 862 shows, impacted 114,195 lives, and donated 5,516 performer hours.

How Win-Win Entertainment Has Grown Over a Decade
Win-Win Entertainment was born from a belief in the inherent generosity of the human spirit. Throughout the many stages of my career, I’ve constantly been struck by how one phone call, one connection, or one chance could completely change the trajectory of a life. I’ve witnessed people want to give back—and have also seen how the busyness of daily responsibilities can get in the way.
I came up with the idea that if I made it easy for people to give back, they would. I would handle the actual labor, speaking with children’s hospitals and gathering a dedicated group of performers who would embark on this journey with me. But, I knew I would need a little help along the way to lift this dream off the ground. Enter my fantastic board members and advisory board!
Over the past decade, I’ve been fortunate enough to connect with some of the brightest minds in Nevada to spearhead Win-Win Entertainment with me. Together, we’ve garnered the support of an avid volunteer base and generous corporate sponsors to contribute to our nonprofit fundraising. It has truly been a joy to witness the efforts of our nonprofit fundraising directly benefit the children.
The Evolution of Nonprofit Fundraising and Charity Events
With the impacts of COVID-19 still ravaging healthcare systems and societies globally, Win-Win Entertainment has been predominantly virtual for the past year and a half. Now that our 10-year anniversary is approaching in the upcoming months, we plan to return to in-person events as soon as safely possible. However, rest assured that our virtual programs won’t be going anywhere.
Through nonprofit fundraising, we’ve been able to fund a trusted web platform that connects Win-Win and its talent to our events and programs in various cities. Now, we can visit children that otherwise couldn’t have visitors due to the risks of their condition. Plus, we can connect our larger market to smaller cities that aren’t entertainment hubs, to bring much-needed smiles.
Win-Win Entertainment is now on track to be bigger than ever! Our continued success with nonprofit fundraising and charitable entertainment only fuels the idea I know as fact: Win-Win is, and always will be, my greatest performance. It took all of our focus, hard work, and heart to get here—and now, we’re returning back to the heart of it all for our 10-year anniversary.
How I Connect with the Heart of Nonprofit Fundraising
At this point, you might be wondering what me being a professional emcee has to do with my role as the founder and chairman of Win-Win Entertainment. The truth is, the two have just about everything to do with one another! As a professional emcee, I’m brought in to host dozens of nonprofit fundraising events each year—and as a nonprofit chairman, that’s the type of work I love!
Of course, my roles as a corporate entertainer and keynote speaker still bring me unlimited joy in my career. However, I connect with the heart of nonprofit fundraising in a way that I simply can’t explain. I know what’s at stake when a nonprofit organization, such as the SafeNest domestic violence organization, asks for donations to support their cause.
In other words, I have strong ties to nonprofit fundraising because I do it myself. I constantly have one foot in my career as a professional emcee and entertainer and one food in the nonprofit world. I understand how to infuse the mission of the organization into the program and how to talk to donors, especially hospitals. Nonprofit fundraising for others is an extension of what I do myself.
What’s Next for This Nonprofit Chairman and Professional Emcee?
So, what’s next for this nonprofit chairman and professional emcee on the eve of the Win-Win Entertainment 10-year anniversary? The world will have to wait and see… but, I’ll give you some hints! In the last two weeks, we’ve added two performers AND two hospital partners to our Win-Win family!
Every please give a warm, virtual welcome to:
- Judson Laipply, keynote speaker and OG YouTube viral sensation,
- Aaron O’Brien, clean comedian and rising magician,
- Methodist Children’s Hospital in San Antonio, Texas, and
- Children’s Healthcare of ATL in Atlanta, Georgia!
We cannot wait to see what’s next for our fantastic performers and latest hospital partners, but we know one thing for sure—it will definitely be amazing! If you’re interested in getting involved with Win-Win Entertainment, now is your time. Visit our website to donate or click here to sign up to volunteer for a virtual visit.
Wishing Win-Win Entertainment an Early 10-Year Anniversary
Well, happy almost-10-year anniversary to a passion project that’s quickly become my greatest feat! I am ecstatic to see what the next decade holds for Win-Win Entertainment, our performers, and our wonderful children’s hospital partners. I encourage you to stay tuned over the following months for more news about our 10-year anniversary!
Likewise, if you’re on the hunt for a professional emcee to host your next nonprofit fundraiser or anniversary, I also suggest you contact me as soon as possible. Between the Win-Win anniversary and existing client partnerships, the next few months are booking up fast! Contact me today to learn how I can help facilitate nonprofit fundraising at your next live or virtual event.