More than a decade after a viral football trick-shot video launched his public profile, John McEntee is channeling his success back to where it started. The former Trump White House official and conservative dating app founder has committed approximately $100,000 to the University of Connecticut’s NIL fund, marking one of the largest alumni contributions to NIL efforts in program history.
The donation represents a full-circle moment for McEntee, whose 2011 quarterback trick-shot compilation earned over seven million views on YouTube and established him as an early pioneer of athlete personal branding. That three-minute video—featuring trash-can bullseyes, hallway lasers, and no-look spirals shot on a simple Flip camera—demonstrated something that has defined McEntee’s career ever since: capturing attention is its own form of capital.
From Viral Fame to White House Influence
McEntee’s trajectory defied conventional career planning. After graduating from UConn in 2012, where he earned the starting quarterback role and threw for 300 yards and four touchdowns against Western Michigan, he moved into media work at Fox News. By 2015, he had volunteered for Donald Trump’s presidential campaign, eventually becoming one of the president’s most trusted aides and serving as Director of the White House Presidential Personnel Office.
Following Trump’s 2020 election loss, McEntee co-founded Date Right Stuff, a conservative dating app backed by tech billionaire Peter Thiel. Through promotion of the app on TikTok, where his @daterightstuff account has accumulated over three million followers and billions of views, McEntee discovered firsthand how digital platforms could drive business growth.
“Long before NIL was officially allowed, I got a taste of how powerful a personal brand can be,” McEntee said. “I hope this fund allows today’s athletes to build their brands and benefit from the impact that can have on their careers beyond football.”
Investing in Athletic Futures Beyond Competition
The timing of McEntee’s contribution aligns with a critical shift in college athletics. When the NCAA allowed athletes to profit from their name, image, and likeness in July 2021, it fundamentally changed how college athletes could monetize their personal brands. However, the reality differs significantly from headlines about million-dollar sponsorships at Power Five schools.
According to NCAA data, less than 2% of college athletes advance to professional sports. For mid-major programs like UConn—competing without billion-dollar TV contracts or deep booster networks—alumni support becomes essential for helping athletes bridge that gap.
David Noble, Director of the Werth Institute, emphasized the symbolic importance of such gifts: “When our former players come back and give transformative gifts year after year, it sends the signal to the current roster that this program is on the rise. It’s about more than money—it’s belief, legacy, and momentum.”
The Art of Professional Reinvention
McEntee’s own career path mirrors the uncertainty most college athletes face. His journey from walk-on quarterback to viral content creator to White House Personnel Director to tech entrepreneur demonstrates the value of adaptation when original plans shift.
“The most valuable players aren’t always the ones with the best stats,” John McEntee said. “Sometimes they’re the ones who figure out how to stay in the game when the original plan falls apart.”
His contribution comes as UConn continues strengthening alumni engagement following its 2024 return to the Big East Conference. Under head coach Jim Mora, hired in late 2021, the program has shown improvement after several difficult seasons. University officials view alumni support as vital for sustaining momentum in an era marked by NIL, transfer portals, and conference realignment.
The donation directly supports NIL opportunities, helping athletes grow their profiles, build businesses, and network beyond football—tools McEntee himself leveraged before such support systems existed. Whether his gift inspires broader alumni participation remains to be seen, but for John McEntee, the goal is straightforward: give today’s athletes the resources to create second acts of their own.
