Turning an idea into a successful business

"It’s helpful to have a group of knowledgeable people with a variety of backgrounds to provide feedback on ideas, suggestions or business advice. Starting a business can be a lot of challenges." Scott O'con

Introduction and interview of Scott O’con by David Wagstaff

As part of our interview series, which provides stories and insights to entrepreneurs, this segment is about Scott O’Con, the founder of Tours of Cleveland, LLC.  Scott is friend of mine.  We met 20 years ago in Charlotte, NC where we both lived.   We reconnected recently when I asked him to be part of our Advisory Board for my start up Alfrea Wellness. Scott’s background in Human Resources enabled help to help us answer questions about how to position our wellness offer as an Employee Benefit.

As a side note for Aspiring Entrepreneurs:

I am frequently asked, when starting a business, how should one find advisors? While advisors can be investors or owners in a company, sometimes, it’s helpful to have a group of knowledgeable people with a variety of backgrounds to provide feedback on ideas, suggestions or business advice.  Alfrea has advisors with backgrounds in farming, organic foods, cooking, marketing, HR, connectors and experienced advisors.  In the case of Scott, I knew him, trusted him and was impressed by the advice and guidance he provided our startup team.

Scott launched Tours of Cleveland, a company specializing in walking tours of Cleveland, little over a year ago.   I was impressed by some of what Scott had written about some of the landmarks in and around Cleveland.  I know Scott is knowledgeable, fun and engaging, so I asked him if he wanted Tours of Cleveland, a company specializing in walking tours of Cleveland, to be part of our series on Entrepreneurship. 

What led you to become an entrepreneur?

My professional background includes retail in my younger days and Human Resources for about seven years prior to launching my business. All of my jobs involved a lot of customer interaction, which I greatly enjoy.

My husband and I moved to Cleveland two years ago for his job; he is the senior pastor at West Park United Church of Christ here in the city. I was working downtown continuing my career in HR but wasn’t really happy at the firm I was working for. Every day, on my lunch break, I would go for a walk and started exploring my new home – Cleveland. I was amazed at all the places and buildings downtown and began learning more about them.

My husband and I love to travel and when we travel, we love doing tours. We love seeing and hearing about the places we are visiting with experienced guides who give us the inside story. I was ready for a change and wanted to follow my passion. We talked it over and decided now was good time to do this. I quit my HR job and began work on putting the business together. It was a leap of faith, going out on my own, but it has been a good experience.


A brief description of your business and what are your aspirations for it?

Tours of Cleveland, LLC offers exciting and educational walking tours of beautiful and historic downtown Cleveland. My goal is to share with folks, locals and visitors alike, how great this city is and its rich and storied history. Cleveland was home to Millionaire’s Row, that contained over 200 mansions belonging to likes of John D. Rockefeller and the other titans of industry here. Today we have the second largest theater district in the United States, Playhouse Square and of course the Rock and Roll Hall of Fame and even the “Christmas Story” House!

In the year that I have been in business, I have seen an increase in the amount of tours booked but I still have a way to go.  My goal is to sell out my tours. I do keep them small (right now about 15 people), because I think it provides a more intimate and personal experience. But I haven’t gotten to the point where I consistently have that many guests on a tour. Even if one person books, I will still offer the tour. We don’t have a minimum number of guests for the tour to proceed. Frankly, my business is too small to turn away any customer and why should someone not get to explore the city because no one else signed up.


What have you done with your business that you are proud of or that has worked really well?

When a local, who has grown up and lived here their whole life, says to me at the end of the tour that they learned a lot or when a visitor tells me, that I have totally changed their impression of Cleveland, then I feel like I have done a good job and that makes me proud. I have gotten a lot of good reviews on TripAdvisor for example and that shows me people are enjoying what I are offering. People don’t always take the time out to write a positive review, so when they do, I think that says a lot about our experience.


What were some of your biggest challenges along the way?

The biggest challenge is simply getting the word out that we are here in Cleveland. A lot of people associate the city with sports or the Rock Hall, which is totally understandable, but we have so much more history than that. They visit but don’t necessarily think of doing a walking tour of Cleveland like they would say in Charleston or New Orleans. 

Another challenge is creating new tours. I offer our standard tour called the Downtown Highlights tour. I hit all the highlights of downtown in one great two-hour tour. Pretty straight forward. I converted that tour last December into the Christmas Edition and it went really well. I will be doing that again this December and am really looking forward to it. 

It takes a lot of work to develop a new tour, planning and research, coordinating with stops where we are going inside, rehearsing and practicing it. But I have to evolve, otherwise things get stagnant. To have repeat business, I need to different offerings.


Have you overcome the challenges? If so how?

Our Visitor’s Center, Destination Cleveland, does a great job of changing that narrative about the city and letting people know we are an awesome city with lots to do but it is a slow process. For me, I have to realize that even though I am passionate about history, architecture and things of that nature, not everyone is and that is okay. I find people who are interested and get them to come explore the city with me, whether they are local or visiting from out of town. That is a challenge I am still working through.

This spring we developed a new tour called Cleveland From the Inside, where we visit the interiors of about eight different buildings downtown. It has done well and continues to grow. Some of our stops include the lobby of the Cleveland Federal Reserve and a church that has four stained glass windows by Tiffany.  I keep evolving and thinking about new experiences to offer.


What have you learned and what would you like to share with other entrepreneurs?

I have to admit, because this was my first time starting a business, I was a little naive. I honestly thought once the website was up and running, I would get tours booked right way. That didn’t quite happen. My first week of business, I had one customer and he was a friend of mine who was in town. He was nice enough to purchase a ticket. I was so excited when my second week, I got customer that I didn’t actually know but she was the only customer that week as well. Growing a business takes time and that has been something that I have had to learn and continue to remind myself about.


Is there anyone you would like to meet or connect with?For example, investors in the electrical industry, mentors in the publishing industry. A knowledgeable SEO person. Specific is helpful.

I am always interested in meeting other folks in this industry, whether they are local or around the country or world. It is helpful to bounce ideas and brainstorm with others in this industry to see what has worked for them and what hasn’t. I have had the opportunity to work locally with someone in this field as well as another down in Columbus, OH and that has been very helpful.

Scott O'con

Scott O'con

Owner of Tours of Cleveland, LLC

Scott loves history and enjoys getting to know people. Scott started Tours of Cleveland to provide people an awesome, informative perspective on Cleveland, his adopted city. Scott offers a variety of walking tours of historic downtown Cleveland.  When looking for what to do in Cleveland, Tours of Cleveland’s walking tour provides a fun entertaining way to see and explore the city.