Diving Into Entrepreneurship as a Second Career | Kaye Bentley


On this week’s episode of the Vibrant Leadership Podcast, we speak with Kaye Bentley, Founder of Asheville Rooftop Bar Tours. She reinvented her career in July of 2018, after 38 years as a mail carrier, when she created a tour company that showcases Asheville’s highly acclaimed rooftop bars, along with the city’s fascinating history and spectacular views. Kaye’s company received a TripAdvisor 2020 Traveler’s Choice Award for the top 10% of attractions in the world.

We chat about her starting a business as a second career, as well as:

  • Her inspiration to dive into the local history of Asheville and share it with others

  • Meeting and entertaining tourists from around the world

  • Connecting with your team on a personal level

  • Honoring the advice and experience of those who have headed businesses in the past 

  • Flexibility in adapting your vision for the unknown future

  • And more

Mentioned in this episode:


Voiceover: You’re listening to the Vibrant Leadership Podcast with leadership speaker and consultant Nicole Greer.

Nicole Greer: Welcome to the Vibrant Leadership Podcast. My name is Nicole Greer and they call me the vibrant coach. In today’s episode I have somebody who I actually met last time I was in Asheville, North Carolina. I have Kaye Bentley, founder of Asheville Rooftop Bar Tours. She reinvented her career in July of 2018. After 38 years as a mail carrier, and Kay experienced the captivating scenic rooftop views of Asheville and its Art Deco architecture and created a tour company that showcases Asheville’s highly acclaimed rooftop bars, along with the city’s fascinating history, and spectacular views. Kaye’s company received TripAdvisor 2020 Traveler’s Choice Award for the top 10% of attractions world wide. Don’t miss that. Kaye is worldwide people. So Kaye, I’m so delighted that you’re going to be on my podcast today. Thank you for joining me.

Kaye Bentley: Thank you so much, Nicole. It’s an honor to be on here. Thanks.

Nicole: Yeah, absolutely. I have totally enjoy being on your rooftop tour. And the best part of it was the history that you history lessons that you gave us while we were. We were on the tour. So I absolutely. When I got done, I asked Kaye, right away, will you be on my podcast, and so she so generously agreed to so I’m absolutely delighted that you’re on our show today. So I have a podcast about leadership. And I see you as a huge leader, because you have just really taken on a path based on a vision that came to you, will you share with everybody kind of how you got the rooftop bar tour started there in Asheville?

Kaye: Sure, um, the idea came to me, as you said before, I was a mail carrier for 38 years. And the idea came to me at the end of 2017, when I was experiencing a couple of the rooftop bars for the first time. And when I saw the views of the city from up high looking down, you know, living in Asheville, we know that we have historic buildings from the 20s. But I saw those, you know, buildings from the rooftops. And at the same time, I was hosting some Airbnb guests in my home and I was buying history books for them to read. And so I started reading the history books as well. 

And then I realized it truly hit me just how deep the history is here in Asheville. And so I thought it would be really neat as I saw those photos from the 1800s and 1900s, I realize that a lot of the rooftop bars were the same, you know, corner street corners, so to speak. So I thought it would be a great idea to kind of do like an Asheville then and now tour. And so that’s how the idea came to me. And it was one of those ideas once I thought about it, it would not leave me alone. I I lost sleep over it. You know, I felt that when I retired from my career with the postal service that I would just, you know, eventually traveled do volunteer work. And I have never thought of being a business owner. And here I am today.

Nicole: That is fantastic. And then to be on the top 10% list for TripAdvisor. Yeah, that’s awesome. So I, I see you as a big leader, I know that you’re involved in the chamber of commerce there in Asheville, and I know that they are celebrating you, because you’ve got this, you’re putting them on the map yet again. So Asheville is a great town. So how would you define leadership?

Kaye: You know, that’s an interesting question. And I was kind of struggling with how do you define it? You know, I think we all can see leaders that we admire and respect. But I think it’s that person that takes a chance and sees a need. And if you’re already in an organization or a business, and if you’re a problem solver, and if you can really connect with people and communicate well and you know, the ideas that you have, can can better people, or, you know, bring something to their lives that they didn’t have before, enrich it in some way. I think, you know, to me that defines what being a leader is you’re willing to take that risk, really, and put those skills that you have in skills you didn’t know that you had, but you actually do you know, into into play.

Nicole: Yeah, well, that is my very next question, you know, is what are the most important skills of a successful leader. So I’m sure that 38 years of working in the Postal Service gave you a lot of opportunities to lead as well. So you probably bought brought some skills over from that. But then what have you had to learn? So tell me a little bit about your own skill set and what you think makes a leader really successful?

Kaye: My skill set I think one of the biggest things that I have is I connect with people, you know, not only do I connect with them wherever they are, and I mean that literally from whatever part of the world or the country they’re from, but really just try to get down on a level where they’re experiencing something, and how can I make it a richer experience for them. And also be true and authentic to, you know, what my company represents. So, you know, connection, and communication is a big part for me. 

You know, when you spend three hours on the rooftops with someone, just like, you know, we did with you, you get to know people, and they share their stories, and you can share stories about, you know, how I started my business, or, you know, how I hired my staff. We’re talking about, excuse me, we’re talking about, you know, businesses in Asheville and places that were passing by, and we’re just waiting that that sense of connection and community together, you know, all throughout the tour. So I think that’s a big part of it, as well.

Nicole: Yeah. So you know, it’s, for somebody who’s great at connecting people to just say, Oh, I’m really good at connecting. But if you look at that closely, it’s this whole idea of building rapport, and being able to identify with people and meet them on their level. So tell me about the person who came from the farthest point on the planet so far on your rooftop tour.

Kaye: Um, one person came from Melbourne, Australia. And we’ve also had someone from Korea that has been on the tour. And, you know, it’s wonderful to hear about, you know, their country, and, you know, everything that that they experience, and what brought him to Asheville, you know, that’s always a real treat for us to know how they found us how they found the city and us up here in the mountains of western North Carolina.

Nicole: Yeah, that’s fantastic. So you’re reaching to all four corners of the earth, t sounds like. Yeah, so so you became an entrepreneur? Tell me about the skill sets that you’ve developed since you started the rooftop tours.

Kaye: The I think the office get all of them. I mean, I honestly, one of the interesting things for me being, you know, starting a business as my second career, and not really planning on starting a business, I didn’t really embrace the, the role or the title of being an entrepreneur for the longest time, because I just thought I was a small business owner, you know, and then I realized, as an entrepreneur, all the things that you bring to the table and all the skills and I realized, it’s like, Okay, well, yes, I am those. And so I guess I am an entrepreneur. But in the beginning months, I really did not, you know, say I was an entrepreneur or felt like I was one. But one of the things that I’ve had to do is I have had to learn everything about the business. And I think this is true for a lot of entrepreneurs. 

When you start your business, you want to know everything and how it works as you’re putting it together. So, you know, I had to develop some skill sets that I didn’t think I would ever be doing, you know, QuickBooks Online, and, you know, I’m figuring out, you know, through Google and YouTube, I’m setting up you know, the TripAdvisor platform, same thing with YouTube. It’s just all of those things are resources that are out there in the community. And I have developed all of those from marketing to, you know, strategy, all of that kind of stuff. So, it was, it is still an ongoing process, to be honest.

Nicole: Yeah. And I think what you’re talking about is like, you know, one of the skills you have to have as a leader is you have to be able to learn, and open and willing to try new things. And to just like, when I like to call a figureouter, you know, you just sit down and you figure it out, you know, you get it, you sit there until you get it. So that’s fantastic. You talked a little bit about hiring your staff. And so you have a team, talk to us about how you lead your team. If you were to give yourself a style, what would you say your leadership style is like, and how do your people experience your leadership?

Kaye: I probably come across I’m, I’m not gonna say that I’m a softy because I’m not. I will make those hard decisions. But I also do connect with them. You know, on a personal level, I I hear about their families. And, you know, before COVID, hit one of our employees was involved in, you know, like some comedy classes and there was a chance for there to be a student performance. And so, you know, we went and supported him in that and so we got to meet his family and that kind of thing. So, you know, I I do like to be involved, and I try to be very approachable, and I think I am. So, you know, I like to have this open, easy communication. And I feel that I feel that we have that we’re small right now. But we we are going to be growing and we are growing, but I still want to continue to have that.

Nicole: That’s fantastic. That’s fantastic. So you’re going to have to clone yourself, because you do a lot of the actual teaching and giving the history lessons and telling the stories and that kind of thing. How does a leader get prepared for growth? What are you doing to get prepared for this growth?

Kaye: I’m talking to a lot of people that are in veteran business themselves, you know, I think the you cannot underestimate the experience that other people have gone through. And so, you know, I’m talking to them, I’m also, you know, trying to tap into some local resources through some of the community colleges, and, you know, talking to my accountant and just trying to figure out, you know, how does someone do this? Or how does a business owner do this, because this, we will be coming up on in 2021 will be coming up on three years in business. 

So it’s, um, you know, I’m opening those, that those communication lines with, you know, other people in the business setting here in Nashville, and, and I’m also one of them on social media, I’m also reading a lot, and I pay attention to, you know, business journals and things like that. And so I’m always, you know, trying to gather information to see, you know, what would be the best way to go forward? And also maybe the best way not to go forward as well?

Nicole: Yeah, yeah. So I love what she said, everybody, she said, she does a lot of reading. And she does a lot of networking is what I heard. So two really very important things for an entrepreneur and a leader. Absolutely. So what do you believe makes some leaders successful and other leaders struggle? What do you think makes them successful? Maybe answer that one first. And then we’ll get to the struggle bus.

Kaye: Think successful, at least the ones that I look up to, you know, I think a lot of it has to be supported by community and how involved they are in the community. And I think that rolls over into the, how they treat their employees and their staff and their team. So, um, you know, I feel that that’s part of it, I think giving back to the community is really important, too. So I see that as a key leadership role. And, you know, and to be successful with that, I think if you have your team on board, you are connecting with the community, you know, even in the tourism business, here we are, you know, in the tourism business, but you know, we have to have local support as well. So, you know, that connection with community is is important. And as far as the what, I’m sorry, what doesn’t make?

Nicole: Yeah, what makes a leader struggle? What do you think, you know, because there are a lot of leaders out there who struggle, what do you think that’s about?

Kaye: Maybe just trying to stick with their original business plan, or their original game plan? You know, I think if 2020 has taught us anything, it’s to be flexible, and to be willing to, you know, look at all possibilities and, you know, different avenues that you didn’t even know existed, but to be open to it. And so I think the people that are, you know, possibly just really they have that vision from the beginning. And that’s the way it’s going to be and they really don’t see beyond that, I would say that they would struggle, especially with the way you know, things are changing today.

Nicole: Yeah, absolutely. Yes. I love that. So I love what you said about the fact that your vision kind of came to you this idea of doing the rooftop bar tours came to you and it wouldn’t let go of you. So when you first shared this with people, what did people think about this? They’re like, you just got retired. And now you’re gonna do this. What did everybody say to you?

Kaye: Oh, gosh, um, we have to realize that I started working on this, I actually bought the domain name in like October of 2017. But I was buying the domain name originally because I realized that no one was doing a rooftop bar tour Asheville, and we had tours for almost everything in the city. And I was surprised that some smart business owner had grabbed ahold of that idea yet. So um, you know, I didn’t tell anybody for about four months, and I worked on it at night. I did my history research. I was, you know, finding those those historical photos that I wanted to use. I was putting together all of these tour schedules and rooftop bars when they were open, what days and so I didn’t tell anyone, even my family for about two months until I realized that you know what? I think this is a great idea. 

But I actually need to tell somebody that lives in Asheville to see if they think it’s a good idea. So I told my daughter who was actually 17 at the time, and then I told my very best friend, and I said, you can not tell anybody you have to promise. And that was early January of 2018. And once I told them, they said, you know, this is an amazing idea, and you really need to follow through with it. So, you know, they actually directed me toward the Western Women’s Business Center here in Asheville. And so that is where I went, and I had some great business coaching there, that helped get me on the right path, I secured some funding there, Good Carolina small business development funds. 

So that right there was the first time I had actually written down my idea for a stranger to look at it. And so I still had not told any of my friends, I was still working at the post office. And if our website was in development, and it was probably May, and we started in July, July. So it’s probably May, when I actually, you know, told a couple of other people and, but I still had not talked to the rooftop bars at that point. So I did not want to talk to them, because I knew word would get out. And you know, maybe another company will come in and start doing what I was planning on doing. So I didn’t talk to them until it was probably the end of May, 1st of June. And I said, this is what I’m getting ready to do. 

So it was a little unnerving, you know, to not have them on board from the very beginning. But also feel like that was what I had to do. Because when I did put the information out there, and I made a, I think it was a post on Facebook, and I said, Hey, all big surprise coming. And so when I did that, so many people were shocked, first of all, that I had worked on this, and I had it all worked out and planned. And then secondly set up were like, I didn’t know you wanted to start a business. And I was like I didn’t know I wanted to either. And then the other thing was, who else is doing this with you? And it’s like, no one just me. And they’re like you thought of this on your own? It’s like, yeah, those are the kind of reactions I got.

Nicole: That’s fantastic. I love that story. Well, in my work, I have a coaching methodology. It’s called shine. And so it stands for Self assessment, Habit work, Integrity work, Next right steps planning, and I heard planning, planning, planning in your story, and then Energy. So a couple of those letters I want to talk to you about because I hear I mean, you really you are a vibrant person. And you definitely are letting your little light shine up there. And Asheville, bringing all your creativity and your goodwill to your community. It’s just absolutely beautiful. So in terms of next right steps, or planning, how do you do your planning? What is what what does a successful leader do in terms of planning? What do they do?

Kaye: I think for me, in planning, I always have a notebook where I have ideas that are flowing, and I’m always putting those in that notebook. One of the things I’ve struggled with is, you know, I came from a completely different career, you know, I work six days a week, almost 10 hours a day, and I did that for 38 years, and then I came to this job, and I didn’t have a structure for anything, you know, I wasn’t used to having Mondays open. And so I I still struggle with trying to, you know, have a more structured day, you know, I’m getting better and better at that. And, you know, there’s a lot of tools out there to use to do that. 

But the planning part is, you know, I have these ideas, and then I put them down and, and, you know, it’s like I have a good gut gut feeling about things. And so when my gut is saying, you know, really follow through on this, then that’s when I put a lot of the effort into trying to plan it and figure out if it actually will work, but always have that notebook of, you know, ideas, and you know, 2021 you know, what do I want to try what I want to look at how can we expand in different areas?

Nicole: Yeah, that’s fantastic. Yeah. So something as simple as just having a notebook and a pen paper and keeping track of that the ideas that come. I love it. All right, so I I assume you have t ton of energy. Okay, especially after you just said six days a week for 38 years, you are working 10 hour days. So how do you keep yourself like, how does the leader keep themselves energized? What do you do?

Kaye: I try to stick to a workout routine. You know, that’s kind of hard sometimes. You know, that’s self discipline. You know, not having that structure. I used to go to the YMCA in the mornings before I went to work at 7:30 and so I’m a morning personalities have been so you know, I’m trying to tap into that morning energy, you know, that I definitely have. But um, you know, keeping, keeping some type of a structure, you know, is is really important. And I get the energy from the people on the tour as well. You know, I know that I hear it all the time, it’s like you get off of some of these elevators. And as soon as those doors open, and you start to walk out, people are like, oh, wow, look at that, you know, and their phones are out there taking pictures immediately. 

And, you know, that’s the way I felt the first time that I saw it. And you know, to see people experienced that, and how excited they are, and just, you know, how much it means to them to, to get away. And even locals come on the tour, and they love it as well. You know, it’s just a real sense of connection for everybody. And there are a lot of people on tour that have made friends while they’re on the tour, and their Facebook friends by the end or they go have dinner afterwards. You know, it’s, I have yet to see a group that has not connected in some way.

Nicole: Yeah, so I have decided what your leadership style is, it’s a connecting style, because you just keep using the word connection over and over and over again. And that was my experience, I met so many great people on that tour and just, you know, really fun time. So really great time and was the AC hotel, I believe where we started and then we were on the rooftop at sunset, it was absolutely gorgeous. And so just I can’t recommend this rooftop bar tour and we ate along the way you can eat away. 

So there’s lots of good fun things to do. And eat along the way. All right, well, we’re going into 2021 and I am just all excited about 2020 being over I know most humans on planet earth are excited about getting into a new year, and hopefully it will, you know, see see daylight at the end of this very dark tunnel we’ve been in. So what what challenges other than COVID you know, because it’s just there, you know? What challenges do you think leaders need to be ready for in 2021? What How are you ramping up to get yourself ready?

Kaye: I think, you know, I was I’m really excited about you know, the vaccines and you know, those kind of things, but then, you know, I just heard that, you know, maybe there’s another strain that is, you know, in Europe and I’m kind of like oh no, you know, so it’s like, here’s all this hope, this hope and then it’s like, wait a minute, hold on a second, you know, so um, you know, I think looking forward, I’m just gonna, I’m gonna try to plan and be ready for things to just, you know, explode in a big way. 

Because I think people are wanting to travel. And you know, I’m talking about the tourism industry here for sure. But even locals, people want to get out again, they want to visit those restaurants in person and a lot are doing takeout and pickup and that kind of thing. But you know, that that connection once again? Yeah. So, you know, I think it could be a real big year for for businesses. And, you know, I do think people are going to want to be out and I’m just open to whatever direction that takes us. You know, if that means multiple tours a day, you know, I will figure out how to make that happen. And, you know, I also have a couple of ideas of some new tours that we’re going to be offering and looking forward to those partnerships locally.

Nicole: Oh, that’s fantastic. That’s fantastic. Well, there’s a lot to see if you’ve never been to Asheville, North Carolina, it is the home of the Biltmore Estate. Also the Grove Park Inn is there and there’s just, it’s a great foodie town. It’s absolutely great foodie town. So you got to go. Alright, so let’s end with this question. Kaye, if you were mentoring a single special listener right now, maybe somebody who’s got that little dream in their head that won’t let them go? What advice would you give them?

Kaye: I would say, do your homework before you before you start and try to find a way if you are, you know, entering into an industry or you know, a business where that type of thing is already represented. How can you be different and set yourself apart? That would be the biggest thing. I mean, you know, ours we are a tour here in Asheville, but we do cover the roof tops. So that was definitely you know, different for us bringing that to the table. But I would say do do your research, you know, in the area that you’re in, I would probably focus with a lot of if he can do things online. 

And I mean, online sales offer things online. I think that that has become a huge market right now. And I really don’t see that going away because I think a lot of people are looking for the ease, you know, of being able to find businesses like that or buy products like that. So, you know, I would focus on that for sure. But I would also say, you know, connect in your community and if that means going through the Chamber of Commerce or any other local business organizations, I would highly recommend that, too.

Nicole: Very good advice. Very good advice. Yeah. So okay, I have been absolutely delighted to have you on the Vibrant Leadership Podcast. If you are in Asheville, North Carolina, please do not hesitate to sign up for the Asheville rooftop bar tour and Kaye will give you a great time. Thanks so much for being on the show. And I look forward to seeing you next time I’m in Asheville.

Kaye: Thank you so much. I appreciate it.

Voiceover: Ready to up your leadership game? Bring Nicole Greer to speak to your leadership team, conference or organization to help them with her unique SHINE method to increase clarity, accountability, energy and results. Email speaking@vibrantculture.com, and be sure to check out Nicole’s TEDx talk at vibrantculture.com/TEDtalk.

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