When contemplating retirement, some people envision playing golf whenever they please. Some buy an RV and hit the road. Some think they’ll finally write that novel. Some, after decades of punching the clock and knowing exactly where they would be Monday through Friday, see it as a parachute-less leap into a terrifying unknown.

Bill Osborne, owner and chief impresario of The Flying Squirrel Pub in Arden, thought none of those things as he contemplated Life After Corporate. The Cleveland-area native and University of Akron graduate (go Zips!) matriculated after college to the Eaton Corporation, headquartered in Ohio; in 2004 he accepted a transfer to Asheville.  His son and daughter went through Buncombe County Schools, and he embedded himself in the community.

When he submitted his retirement notice to Eaton, he had a plan. Sort of. “I’m not a person who always wanted to open a restaurant,” he says. “My intention was to do something I had a passion and drive for, when I was old enough to retire and while still young enough to do something entirely different.”

A restaurant/pub concept piqued his interest, but with zero experience in the field, he decided that taking on a franchise of an established national operation would be safer than striking out on his own, and an opportunity to learn on the job.  He got the keys to the building and opened the door in October 2023.

Things were holding steady that first year, but then in September 2024, Helene hit Western North Carolina. “Helene changed the landscape tremendously,” he recalls. “We were lucky enough to have limited damage and most of my employees were fine; one became unhoused. We were more fortunate than many, but the next six months were tough, very tough.”

While absorbing and navigating a life-changing disaster, he realized he was not meant to be a franchisee.  In early 2025, he came to an agreement with the parent company and declared independence, keeping possession of the building, equipment and furnishings.

The timeline for the rebrand was short and he needed a name STAT, but batting around ideas with family and friends, nothing was feeling right. In the nick of time, he got a call from a tenant in a rental he owned. “He told me something was living in his attic and that something turned out to be flying squirrels. We went over with humane traps, caught the squirrels and re-homed them in the woods.”

While cursing the flying squirrel takeover, he also considered the serendipity of it. “I threw out the name The Flying Squirrel and everyone liked it. I got in touch with a college friend who is a creative director and asked if he could come up with graphics and a logo. He said sure, but it would be 3 to 6 months before he could get to it. I said great, we need it in 3 to 6 days.”

A friend in need is a friend indeed, and within days, the friend sketched a precocious little squirrel head wearing a WWI fighter pilot brown leather helmet. “It was brilliant. We were thinking of actual flying squirrels, and he came up with a squirrel flying a plane. Everybody loved it. We knew could take that and run with it to decorate the place – airplanes and squirrels.”

In April 2025, The Flying Squirrel Pub took off as an independent bar/pub/restaurant with a goofy little mascot. “We did a promotion with a local radio station to name him, and the winner was Chester A. Corn.”

Rebranding and re-decorating was just the start. They tackled the food menu, committing to making as much as possible in house. The kitchen hand cuts pounds of potatoes daily for fries and chips and came up with new recipes for sauces, dips, condiments and sides. That has paid off with consecutive wins from the Asheville Media Group for Best Pub Food, Best Fries and Best Wings.

Osborne delighting in naming some dishes. Like Burnt Ends Justify the Cheese, one of the Squirrel’s specialty mac-and-cheeses: pimento cheese mac topped with pork burnt ends, fried jalapenos, pickled red onions, cilantro and lime creme. Sliding Rock Sliders is another: three Angus beef patties and melted cheddar on toasted slider buns with pickles, Squirrel sauce, and topped with caramelized onions.

The Forager Burger is topped with a mountain of mushrooms, favored target of Asheville foragers; Just a Burger is just that; Gaby’s Black Bean Burger is named for his daughter and Max’s Buffalo Blue Pizza for his son.

Pineapple Does Go on Pizza — house made marinara, pineapple, bacon and jalapenos, topped off with Caribbean Jerk sauce and green onions – is the result of an argument with the kitchen manager.  Osborne was an emphatic hater of pineapple on pizza. Osborne lost.

But his acquiescence squares with his goal to have something for everyone on The Flying Squirrel Pub. That includes 20 beers on tap, primarily local and regional with a couple of national brands like Guiness, Modelo and PBR; Sierra Nevada NA beer; Bold Rock and Flat Rock Cider; and hard seltzer cocktails. (Because the pub is on the unincorporated side of the Buncombe County street, they cannot sell spirits.)

Trivia Tuesday with Billy is weekly at 6:30 p.m.  Thursdays are Music Bingo, with song titles rather than numbers on bingo cards and 30-second snippets of songs played to identify and match on your card. When the original host moved, Osborne reluctantly assumed the role. “I strongly encourage cheating.”

He’s honest when asked if Bill’s Big Idea for this stage of his life has delivered what he hoped. “Well, Helene was the worst six months of my life, but it also showed that the Squirrel has become what I wanted it to be, a true neighborhood spot. We would not have made it if the people around here hadn’t come out to support us. They really loved us through it.”

The Flying Squirrel Pub is located at 3578 Sweeten Creek Rd, Arden, NC 28704.

To learn more, please visit theflyingsquirrelpub.com.

Written by Kay West