Coleman Crawley quit his day job to go to college basketball games, one a day (at least) up until Selection Sunday. That’s the day the NCAA Tournament committee picks the field of teams for March Madness, the annual men’s basketball tournament to determine the national champion. The Fort Gibson native lives in Oklahoma City with his wife Emiley Sexton Crawley (full disclosure: She used to work for 405 Magazine.), and until recently worked as an employee benefits consultant for Gallagher Insurance, Risk Management and Consulting.
We talked to Crawley about his plans to build a business around college basketball while he was on the road between a double-header: Towson State vs. Hofstra, and Penn vs. Princeton.
“I grew up playing basketball, and I wanted to play in college, too,” Crawley said. He’s a coach’s son. “I fell in love with the game the year my dad coached a team into the state tournament. They’d only gone .500 that year, but they got some key wins in postseason, and they made it into the state tournament. That led me to believe naively that anything is possible.”
Crawley played high school ball at Fort Gibson, and his plan after high school was to earn a scholarship at a small college or even play as a walk-on. “I figured I’d turn that into coaching or sports journalism,” he said. “I knew I wasn’t good enough to play division one, but I thought I could make a small school work.”
When the initial plan didn’t work, Crawley was faced with “going to school for school,” and that left him with a decision: What focus should his education take?
“My grandfather was a businessman, so I thought maybe a vague degree related to business, but I hated the classes,” he said. “I like people, so I opted for sales, and that’s how I landed at Gallagher.”
In 2019, Crawley discovered Barstool Sports, the New York City-based digital media company that revolutionized sports-talk programming with irreverent, funny and insightful commentary and pop culture mash-ups.
“It was during the PGA Championship in 2019 that I really noticed them,” Crawley said. “They got amazing access, and they were genuinely funny, saying things you can’t say on network or cable sports shows.”
The idea of producing content for a company like Barstool Sports took up residence in Crawley’s head. In 2020, when the NCAA Tournament was canceled, Crawley created a podcast for his friends in which he picked teams for a fake NCAA tourney. His friends were quick to tell him he had a talent for it. But he knew he needed a niche to get someone’s interest.
“There is plenty of content about the big schools,” Crawley said, “but the small mid-majors are not covered well, even though they work their asses off, and every year, one of them makes a run in the tournament.”
We’ve cheered for those teams for years: Richmond, VCU, UMBC, Butler, and so many other scrappy schools with the selfless team players or the one superstar who carries the team — think Steph Curry at Davidson. Crawley decided this would be his niche, and he didn’t just decide, he took his sales commission from last year and bet on himself. He and Emiley talked it over, and he joined her on a business trip for her company to New York City.
“Emiley has given me an irrational confidence in myself,” Crawley said. “I’m also very much a personal faith guy. If I have the right intentions, I believe God will pave a path for me. I’m also super competitive. I was undersized in sports, so I had to outwork, outthink and out-hustle everyone else. That’s contributed to my drive for sure, and my love for these small mid-majors.”
He took that energy and ambition to NYC in July last year with Emiley. While she sat in meetings with the company she worked for, he stood outside of Barstool Sports’s headquarters, waiting for someone to come outside.
“I knew someone would come down for lunch at some point,” he said. “I felt a bit like a stalker, but I just needed to make a three-minute pitch, and after a few hours Big Cat walked out the door.”
Dan “Big Cat” Katz is one of the company’s most popular sports pundits. Crawley caught up to him walking down the sidewalk. His pitch? Yes, Katz had time to hear it. The pitch was simple: follow me on Twitter (@SharpshotSelect) and let me prove to you my method of picking mid-majors will work.
“I never expected to be on his podcast,” Crawley said. “I thought maybe he’d just give me a little advice on how I could improve or some encouragement, but he invited me onto the show.”
The three-minute pitch turned into a full-blown Q&A, and the result was thousands of new Twitter followers. And now Crawley has at least one person at every small division one school following him, and in an environment where coaches, athletic directors and would-be star athletes are looking for coverage and amplification, Crawley is providing a new, young, studied voice.
“I keep a binder with all the relevant information: school size, players, average attendance, record, tendencies in the NCAA Selection Committee’s past picks — all kinds of data. It’s ‘bracketology’ style like Joe Lunardi started, but I focus on the mid-majors. They’re the hardest to pick because they get very little coverage.”
That’s the niche. He’ll happily sell gambling picks for those small schools, but his plan is to sell advertising to those small schools, and the big dream is for Barstool Sports or another digital media company to offer him a gig doing what he loves. So far, he’s proven that he has the tenacity and passion.
“It’s scary to quit your job,” he said. “I quit on January 16. I’ve come to believe that you have to do scary things. That’s how you grow.”
