Meet Our Team
Frank Hughes
Founder
Two careers, one mission: protect athletes’ financial futures. Frank spent 20 years as a sportswriter covering the NBA, NFL, and Pac-12 for top outlets before building a successful insurance and securities practice in Silicon Valley and Southern California. He leverages a rare blend of sports insight and financial expertise for every client.
Raymond E. Kingsfield
CFA
Former wide receiver at William & Mary, player-coach in Europe, and Chartered Financial Analyst, Ray has spent 15+ years managing a family office in Chicago with disciplined, creative investing. He now grounds NIL Insurance Company’s coverage in disciplined, real-world risk management for athletes and institutions.
Holden Hughes
Sales Associate
Holden played five years for the Drake University football team, winning three consecutive Pioneer Football League conference championships while being named an All-League defensive back twice. He graduated in 2025 with degrees in marketing and finance. He worked for Fenix Pest Control throughout his college career doing door-to-door sales throughout the Greater Des Moines area, antagonizing pests the same way he did opposing receivers.
Caleb Bowling
Sales Associate
A native of Winston-Salem, North Carolina, Caleb played four years for the Drake University football team, helping secure two consecutive Pioneer Football League conference championships while earning All-League defensive back honors twice. He graduated with honors in 2025 with degrees in Kinesiology and Health Science. Caleb currently works in medical device sales throughout the Des Moines metropolitan area. He now focuses on protecting people and organizations with the same intensity he once brought to protecting the field.
NIL Insurance Company is licensed to place insurance in all 50 U.S. states.
What Guides Us
- Athletes first—always
- Privacy and integrity
- Clarity over jargon
- Results over hype
- Sport-and gender-inclusive
FRANK’S SPORTSWRITING
AS SEEN IN
AS SEEN IN
Selected books and articles from Frank’s years covering pro and college sports:
- The Wizards? Snap out of it, Michael · ESPN
- Championship rings not the sole reserve of NBA’s greatest players · Sports Illustrated
- Front-office politics get dirty · ESPN
- Blazers face another tough decision with injury-plagued Oden · Sports Illustrated
- New League in the Making · The Washington Post
- Slick Watts’s Tales from the Seattle SuperSonics · by Slick Watts and Frank Hughes (2005)
and Spencer Haywood (right)
With NFL Hall of Fame reporter John Clayton (left).
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Licensed in all 50 U.S. states. Coverage subject to underwriting and availability.