"I realized I don't have a prayer right now," says Henning, noting the shop's revenue did not match its debt.
"I know it's not the most opportune way to close the shop, but looking at the issues involved and what is needed, I've run out of capital to be able to compete in this town."
Henning says he shuttered the shop after his doctor advised him to "get rid of the stress in his life." He says his health had begun to suffer from his anxiety over finances.
"I asked myself, 'Do I have it in me to do this?'"
Henning worked out of his basement before opening his first store at the corner of Few and Williamson streets. He was motivated less by business reasons than by his love of bicycles.
"I would not be doing any other business other than specialty bikes," he says. "I am not a business man."
Common Wealth Development, a community-oriented nonprofit seeking to improve Madison neighborhoods, helped Henning with the launch.
"[They] helped me focus in the right direction," Henning says. His neighbors had assured him the bike-shop business "would be right up Common Wealth's alley."
Common Wealth helped Henning develop a business plan and successfully apply for a community block grant.
The store became known for its community orientation and Henning's hands-on involvement.
In 1994, Henning moved from 409 Few St. to 601 Williamson St., part of Machinery Row. He also opened a branch at 3729 E. Washington Ave. in 1999.
He left Machinery Row in 2002, moving to 640 W. Washington Ave. in 2003. That store closed in November 2012, and the East Washington Avenue store followed in July. (Yellow Jersey, another longtime bicycle shop in Madison, recently announced it would be relocating to Arlington at the end of August.)
Henning says it has become more difficult to compete with other bike shops in Madison, especially after this year, when business lagged due to a delayed spring. He says his main competition came from Budget Bicycle Center and Erik's Bike and Board Shop. Both carry such big-name brands as Trek and Specialized, while Willy Street Bikes did not sell many major brands. And in the past few years, these large brands have dominated the market.
"The major brands came together to really place a sucker punch in the whole market," says Henning.
As of now, Willy Street Bikes is for sale. The store on East Washington is intact, with the fixtures still in place. Although Henning's goal is to sell the store at its current location, he says he is open to other options.
"It's whatever comes along, really," says Henning, who wants to focus on reducing his stress and taking care of his health.
Henning says he hopes someone will be interested in reopening Willy Street Bikes. But, he adds, "It cannot be me."