20 Under 40: Bill Crosby
Two photographs of Bill Crosby’s grandfathers sit near his desk.
“I keep them above me,” he said. “They watch me from the shelf.”
Crosby, 38, who is a partner at Steamboat Select Insurance Group, views his own community service as an homage to his grandfathers.
“They say we stand on the shoulders of giants,” he said. “When you have opportunities to see the right path in front of you because other people showed you the right path, your job is to continue down that path.”
See all of the Steamboat Pilot & Today’s 2021 20 Under 40 winners here.
Crosby’s career path started as a stockbroker on the East Coast, but after the 2008 market crash and watching the inability of his industry to fix it, “I looked at myself in the mirror and said, I don’t like this.”
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It was also in 2008 that Crosby joined the Lions Club alongside one of his grandfathers. He immediately joined the local Lions Club when he moved to Steamboat Springs in 2010. Crosby served as president for three years and was instrumental in merging the two local Lions Clubs into one organization.
“There’s something about being able to give back that gives you a feeling you can’t get anywhere else,” Crosby said. “To help people who can’t afford glasses or contacts to be able to see clearly — I couldn’t be more proud of an organization doing things like that.”
Todd Hayes, president of Steamboat Select Insurance Group, where Crosby has worked for the past decade, pointed to Crosby’s role in growing the membership from seven to 50 people — along with its charitable impact.
“He brought a newer, fresher approach — and a lot of life — to what is otherwise known as a stoic organization,” Hayes said.
A native of the Shenandoah Valley in Virginia, Crosby grew up on a farm.
“I will always consider myself a farmer … it is where I learned the value of hard work and learned the harder way is often the right way,” Crosby said. “There’s never anything easy on a farm, but it prepares you for the world.”
Crosby and his wife, Tara, moved to Steamboat with a dog and two cats — drawn by their love of skiing and in search of a community in which they wanted to raise kids.
Teaching his 5-year-old daughter, Scarlett, to ski and watching her become his “ski buddy” has been one of Crosby’s greatest joys in life. The couple also has a 2-year-old son, Cyrus.
Crosby’s appreciation is made deeper by his Perthes disease and major corrective surgery at age 10. He was told he’d need a hip replacement by 35 and wouldn’t be able to be active — a diagnosis he’s defied.
In his work as an insurance broker, Crosby works hard to ensure his clients are treated fairly.
“Whether it is a small matter or something significant, he’s going to be a fighter for you and advocate for you,” Hayes said.
For the past three years, Crosby served as director of business development. As of Aug. 2, Crosby was made a partner.
“A lot of times the easy thing is not the right path,” Crosby said of how he approaches his life and work. “I know it is going to take more — but it’s going to be the right outcome. Leadership is taking the harder path and showing people why it’s the right thing.”
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