In this episode of The First Day from The Fund Raising School, Bill Stanczykiewicz, Ed.D., welcomes Connie Falcone, JD, founder and CEO of Firefly Athlete, for a conversation about what fundraisers need to know when sports and philanthropy collide. Connie brings serious insider credentials: seven seasons leading Cubs Charities, a 2016 World Series ring, and the proud title of “Connie from the Cubs.” Her work now focuses on helping athletes turn purpose into action by reducing the barriers that often keep them from engaging meaningfully in philanthropy.
Bill and Connie unpack why philanthropy can be surprisingly hard for professional athletes, even with fame, resources, and cultural influence. Many athletes assume the first step is starting a nonprofit, but Connie warns that creating and running a charitable organization is a major undertaking, not exactly a “grab a lemonade stand outside Wrigley and call it a foundation” situation. Athletes face limited time, demanding training schedules, constant travel, family responsibilities, and a real need to protect their careers. As one NFL player told Connie, much of his day is spent figuring out how “not to get cut from the team.”
The conversation also explores trust, access, and authenticity. Athletes are frequently approached by nonprofits, agents, teams, family members, and plenty of people who may or may not have the right expertise. Connie emphasizes that nonprofits should not simply chase star power; they should look for genuine alignment between the athlete’s lived experience, values, and charitable interests. If an organization supports food insecurity, first responders, youth mentoring, or another cause, the best athlete partner is someone with a real connection to that mission. Otherwise, the partnership risks feeling like a celebrity sticker slapped on a brochure.
Bill and Connie close with practical guidance for nonprofits considering athlete ambassadors. First, expect that securing an athlete’s involvement may require paying a fee, especially at the beginning. That investment can open the door to a relationship that may grow over time, perhaps even into future giving. Second, nonprofits should understand what athlete ambassadors are best positioned to do: expand visibility, reach new audiences, and bring in everyday donors, rather than magically landing a million-dollar gift while fireworks explode over the end zone. The takeaway is clear: sports philanthropy works best when nonprofits lead with mission fit, patience, professionalism, and stewardship; not just a dream of getting a famous name on the gala invitation.
