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Encore Entrepreneur Corner: Kaye Bentley shares the best views in Asheville

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Kaye Bentley is the founder of Asheville Rooftop Bar Tours and is one of Asheville’s proudest ambassadors.

Before becoming an encore entrepreneur, Kaye’s first career was a rural postal service carrier, which she did for 38 years. She took the postal exam when she was 18, passed it, and began as a substitute in hometown of Boone. She proceeded to work her way through college where she obtained a teaching degree in physical education. After graduation, she transferred to Marion where she delivered the same mail route for the next 33 years.

About eight years ago still working in Marion, Kaye moved to Asheville where, at 49 and still inventing herself, she took her first dance class and joined a local dance troupe that performed “jazzy show girl” variety shows at local venues.

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Kay Bentley, Asheville Rooftop Bar Tours

She loved Asheville and all that it offered, knowing that when she retired, this was where she wanted to be. As an AirBnb host, she loved talking to her guests, and through these conversations, realized people love to visit Asheville. And she loved sharing what she knew about the area. It was around this time that she went to a rooftop bar that had just opened in downtown. She was so impressed with the views of historic buildings in Asheville that she started seeking out old photos in the library that corresponded with places where the rooftop bars were located. She discovered how rich the history was. It was then the thought of tours came to her. She wondered if something like this was already available. It was not. And the idea of “Asheville Roof Top Bar Tours” was born. Kaye became obsessed with her vision and would not rest until it became a reality.

She started bootstrapping her new business. While continuing to serve as a mail carrier, she drove to and from her day job, voice-recording ideas, assembling pieces of the puzzle together to see how she could make it work. She hadn’t told anybody about her idea until she couldn’t stand it anymore. She told her best friend who thought “this is amazing” and encouraged her to talk to WWBC (Western Women’s Business Center). She made an appointment, was assigned a business coach and was asked if she had a business plan. “No, but I have several legal pads full of notes,” Kay responded. She didn’t even have a resume. A relationship was started that day!

Kaye retired from her postal carrier position in June of 2018 and did her first rooftop tour July 6th of that same year. Her passion of wanting to share Asheville and its history to visitors and locals alike is why she is successful. She shares historical photos and tells stories from the rooftops, as groups usually hold a cocktail or mocktail, in hand. Kaye believes that if you can help them understand the community, and appreciate its history, they will love and appreciate Asheville, becoming ambassadors themselves, and spreading the love to friends and neighbors.

Everything Kaye learned about business was self-taught or with the help of her coach in the beginning. She was not even in the habit of balancing a check book before launching her business and now she is a pro at QuickBooks!

Kaye attributes the local entrepreneur community, especially WWBC, for helping her get started. Her coach assisted in getting her thoughts together and preparing to apply for a loan. She quickly realized there were many things she had to learn. She knew at the outset that she wanted to be connected to community. She became a member of the Chamber, which helped her connect to other small businesses. She took advantage of free resources, such as workshops, classes, and seminars from JB Media Institute, Explore Asheville, and others.

Advice she offers others who want to start a business:

· Take advantage of all the local resources the entrepreneur community has to offer.

· Network and build a network! You never know when a connection is going to come back around.

· Make yourself different, be unique, find a niche market or solve someone’s problem they didn’t know they had.

· Figure out how you can do more with less…save resources where you can.

Post Script: In the last few months, COVID has devastated the local tourism business and Kaye’s business has suffered like many. All tours were cancelled, and she refunded the deposits she had received. It has been an extremely stressful time. But Kaye, much like other small business owners, kicked into survival mode and looked for assistance… grants, loans…wherever she could find it. But she knew there were others who were suffering as much if not more than she was, and she wanted to help. So, she took her 12-passenger van and volunteered to deliver meals from restaurants to local hospitals or wherever they were needed. Today, with tourists starting to make their way back to Asheville, Kaye is starting to see her business pick up. With safety first, she has reduced her tours to half capacity, and requires masks and physical distancing throughout the tour. She now takes all the photos (via her mobile) and sends them via her phone to her patrons. This way, she doesn’t have to touch their phones and the tour group is fully represented. While Kaye looks forward to the day the pandemic is behind us, she has never wavered in showing her love for the Asheville community, being her usual ambassador self throughout!

To learn more about Kaye and Asheville Roof Top Bar Tours, go to its website, Facebook, Instagram and TripAdvisor.

AARP’s mission is to empower people to choose how they live as they age. Support of encore (over 50 years old) entrepreneurs is one way AARP fulfills that mission in the mountain region of North Carolina. According to recent studies, encore entrepreneurs make up the fastest growing age group of people starting a business.

Connect with AARP Small Business Resources here: Stay inspired with the stories of local Encore Entrepreneurs in the Mountain Region at

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