1651 – Business Is A Video Game with Can’t Wait To Retire’s Jessica Dragan

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Owner of CWR, Jessica Dragan.

In this episode of the Thoughtful Entrepreneur, your host Josh Elledge speaks with the Owner of Can’t Wait To Retire, Jessica Dragan.

Jessica's journey into business transition investment was a complex one. After leaving the military, she accidentally fell into business ownership. She built and grew her own business, but eventually, she disliked it and wanted to sell. However, the pandemic allowed her to pivot and explore new ventures.

One of these ventures was managing a mini golf course, an experience that led her to discover her passion for mergers and acquisitions. Jessica explained that her business ownership background and ability to evaluate and fix businesses naturally led her to this field.

Jessica shared her experience of hating her business due to the constant focus on the company, lack of work-life balance, and challenges managing a large staff. She emphasized the importance of having a balance and enjoying the work you do.

When asked for advice on processing these feelings and making a change, Jessica suggested a solution for business owners who want to sell but still want to be involved in the company. They can stay in the company and choose the role they enjoy while Jessica and her investors take over the business operations. This can be an excellent option for those who don't want to exit their business altogether.

Key Points from the Episode:

  • Discussion on the value of veterans in the business world
  • Jessica's military experience and how it influenced her approach to business
  • Jessica's role as a business transition investor and her journey into this field
  • Jessica's experience of building and selling her own business
  • The impact of the pandemic on Jessica's career and her pivot into mergers and acquisitions
  • Jessica's reflections on the challenges of business ownership and the importance of work-life balance

About Jessica Dragan:

Jessica Dragan is a highly experienced and successful business consultant with a background as a veteran of the United States Army. In 2004, she entered the world of business ownership, where she has thrived ever since. Specializing in due diligence services, Jessica assists companies in various stages of their entrepreneurial journey. She excels in business transitions for retiring individuals, those facing life changes like illness or divorce, or anyone seeking a fresh start.

With her no-nonsense attitude, Jessica is dedicated to helping her clients increase revenue and reduce fixed costs, making her an invaluable partner to any business owner. Her adaptability and quick thinking have proven beneficial in diverse situations, from turning around struggling mini-golf courses to guiding clients through complex business transitions.

Having undergone extensive training in mergers and acquisitions, Jessica has cultivated a valuable network of investors and collaboration opportunities. She values strong relationships and constantly seeks ways to build and maintain connections with clients and partners. Jessica's unwavering belief in the potential of every business drives her passion for helping them achieve their full capabilities. With her military background and ability to tackle challenges head-on, she is exceptionally equipped to take businesses to new heights.

About Can’t Wait To Retire:

Can't Wait to Retire is a strategic investment and acquisition firm with a distinctive approach. Can't Wait to Retire specializes in identifying businesses whose owners are considering exiting, whether they know it or not. What sets them apart is its extensive network of seasoned professionals and a forward-thinking mindset that explores unique possibilities.

They offer financial backing and leverages its network to provide businesses with the resources and expertise they need to reach their goals. The firm's approach is characterized by adaptability and innovation, ensuring that companies are positioned for success, whether it's growth, transformation, or preparing for a seamless exit.

Their commitment is to guide businesses to their desired destinations, utilizing its wealth of experience and a proactive approach that embraces unforeseen opportunities. 

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Links Mentioned in this Episode:

Want to learn more? Check out Can’t Wait To Retire website at

Check out Jessica Dragan on LinkedIn at

Check out Jessica Dragan on Facebook at

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Josh (00:00:05) - Hey there, thoughtful listener. Would you like consistent and predictable sales activity with no spam and no ads? I'll teach you step by step how to do this, particularly if you're an agency owner, consultant, coach or B2B service provider. What I teach has worked for me for more than 15 years and has helped me create more than $10 million in revenue. Just head to up my influence and watch my free class on how to create endless high ticket sales appointments. You can even chat with me live and I'll see and reply to your messages. Also, don't forget the thoughtful entrepreneur is always looking for guests. Go to up my and click on podcast. We'd love to have you. With us right now, Jessica Dragan. Jessica, you are a business transition investor. You're found on the Web at Can't wait to Retire. Jessica, thank you for joining us.

Jessica (00:01:10) - Absolutely. I'm so happy to be here.

Josh (00:01:12) - I'd love to point this out right at the top. You're a military veteran, so thank you for your service.

Josh (00:01:17) - And we love having a business veteran or otherwise associated with the military. In one way, they're now kind of serving, you know, other business owners and leaders. So thank you so much for that. And like every other military veteran, I suspect that your time in uniform has has influenced how you show up in the world today and what you do.

Jessica (00:01:42) - Oh, absolutely. Um, it's really interesting how you learn everybody's role in your team, right? Just in case something happens, you need to know what everybody else's job is, and you work accordingly as a team. And then I find myself in business completely on accident. And I was able to wear all those hats for the business for many years, all by myself, with the exception of always hired an accountant. So yes, it definitely influenced me.

Josh (00:02:11) - And what do you do today is a business transition. What does that mean?

Jessica (00:02:15) - Well, we work with businesses that basically if you hate your business, you need to call me. If you've been in business for a while and nothing seems to be working, I offer a fresh set of eyes so that I can identify the problem so you can fix it.

Jessica (00:02:30) - And then we focus on increasing your revenue and cutting fixed costs by M&A practices. And if you decide you still don't like your business or you want to stay on, there's a very good possibility I would buy that business from you.

Josh (00:02:47) - And how did you find yourself in this role?

Jessica (00:02:50) - Oh, that is such a long answer, but basically. As I mentioned, I fell in business completely on accident in 2004 when had gotten out of the military. I was actually looking to work at the airport, but I couldn't figure out how to get past security because 911 had happened to get a job at the airport. And I enrolled in massage school and they had an internship that taught me basic business and told me that I could take the clients with me when I graduated. So I did. And next thing you know, I had a business like so had to fumble through the whole thing. I created it from start to finish, you know, the name, the website, the credentials, all of it. And by 2017, I hired my first employee, and then by the end of 2019, I had a staff of 31 and they were making me crazy, like, Oh my God, I was at such a point I hated that business and I didn't realize that selling it would have been an option.

Jessica (00:03:53) - And I also didn't know what I would have done if I would have sold it. It was what I was just really used to, you know? And the pandemic came and crushed that business. And I couldn't have been more excited because, like I said, I hated that thing, but I couldn't close the doors. It was a successful business. I have wonderful clients and I had plans to pivot in a different direction, which included a whole rebranding to attract clients that would book us more than once or twice a year and staff that was more professional and presentable. And also we had launched in Washington, Illinois and Maryland, and I wanted more of that. You know, I just wanted to have like a nationwide presence. And during the course of my business, I would try different mergers and acquisitions pieces. And I don't even know how I did that, like where that came from, where the idea came from or where it stemmed from, to include giving equity away to a social media marketer to get that portion, you know, up and running.

Jessica (00:04:59) - So during the course of my business as well there what there would be things that I would consider a mini pandemic that would happen. I feel like business is a video game and once you reach a certain level, it's time to go to the next. And sometimes there's clients that you don't really have for a week or two, and then all of a sudden you make a couple of changes and pivots and next thing you know your business is better than it was before and the stakes are higher and you know, what are you going to do? So when the pandemic came and crushed it, I was like, This is a wonderful opportunity to figure out what's next for me. And I know that whatever it is, it's going to be really amazing and it's going to blow my mind and it's going to be awesome. And I ended up managing a mini golf course of all businesses. It couldn't be any different from massage. But, you know, I've been working since I was 12 years old. I've had various roles, you know, to be a cashier and all kinds of stuff.

Jessica (00:06:00) - So when I came in there, the business owner and his brothers inherited it from their late mother and they absolutely hated that business and they basically handed it over to me. They're giving me keys, credit cards, letting me look at the, you know, the financials and everything and said, here, Jessica, take this business. Just run it like it's your own and make sure that that cash register is balanced. So I did I went in and I worked with the teenagers. It was an awesome experience mentoring them. I had the owner to use for reference. He was amazing mentor. We went to work, I gave a place, a facelift. We ended up with all new staff, all new relationships, kept relationships. We even increased the profits. And by the time I was done with that thing, the state senator gave us an award for best mini golf course in Wisconsin. I didn't apply for that. Like, I don't even remember people coming in like Secret Service agents to play mini golf.

Jessica (00:06:58) - It was there all the sudden. I've got this award. I'm like, This is so cool. But while I was wrapped up in that, I ran into mergers and acquisitions challenge. And when I went through it, I said, That's it, That's what I want to do. It was like everything made sense from start to finish since I have been in business and I knew that I could go to a completely different industry and blow it out of the water. And that's how I ended up in mergers and acquisitions.

Josh (00:07:26) - Yeah. Wait a minute. So tell me more about like how you go from business ownership. You obviously own, you know, the massage business you own or you're managing the the golf course mini golf course. And so we're it seems like how do we get to mergers and acquisitions? What make sure I didn't miss something there.

Jessica (00:07:47) - It leads that way because you have basic business principles and you look at the business and you evaluate it and you figure out what needs to be fixed with it, and you make the necessary changes that come with it to include working with people, which I'm very, very good at.

Jessica (00:08:05) - Mergers and acquisitions has a lot to do with. When you have a company, you go ahead and purchase the companies that support it and that's how you get your revenue up and your fixed costs down because you're going to bring another business in with cash flow. And then you already have staff that's trained. It's a it's a much more powerful way to do business than to just start something from scratch.

Josh (00:08:31) - Jessica, you mentioned something a couple of times now about, you know, hating or loathing one's own business. How does that happen? You would think from the outside that if someone starts a business, they must be, you know, it's kind of like that adage, you know, do what you like. You know, never work a day in your life. You're right. And, you know, so certainly if you start a company or buy into a company, you must be really into whatever you're going to be doing. So you're going to love it forever and you're going to love all aspects of it.

Jessica (00:09:02) - And, you know, I did from the time I woke up in the morning till the time I went to bed, all I could do was think about this business and what was I going to do with it and what's the next best thing and who do I get to meet and how was this going and what needs to happen? And essentially with that, I burnt myself out. So, you know, it was a lot of waiting by the phone for last minute clients to and they were only available. They had one hour of the day and then I ended up changing the whole business a very good at that, looking at the business and scrapping it and then like rebuilding it to whatever it needs to work. So in the end there we were working with disabled and elderly and corporate only we weren't even seeing individual clients and. Yeah, it was just the constant thinking about business, not having a balance, not really having a life, just trying to make sure that all the the wheels are spinning. I mean, you know, you have your business, but then next thing you know you're dealing with your cell phone isn't working and you're at the Apple store and that eats so much of your time, you know? But I think for me, where I really started to hate it was I had a staff of 31 people didn't have any formal training in business.

Jessica (00:10:22) - I didn't go to school. I didn't plan for this. And they were doing things that I couldn't control, like being on time and walking off jobs. And it was just it was an embarrassing thing. And I know that in 2019, while I was going through this with the staff, um, I just kept reminding myself all the years before that I had worked with other professionals and it was enjoyable. There was just something about 2019 that just wasn't working for me.

Josh (00:10:52) - And so for our friend that's listening right now, and maybe they can identify with some of what you're talking about. Maybe it's not hate, but, boy, they are just not enjoying the day to day. Right. They find themselves maybe it's they feel like they're running an adult daycare. You know, maybe they're just way too many complications, problems putting out fires. They're just negatives that go along with it that are like, you know, they might be saying in their head, you know what? I love this, but I hate all this other stuff.

Josh (00:11:30) - And so what? How might one kind of process that initially to like it's like if they say, well, I don't want to do this forever, like I need something needs to change. Maybe it's not a sale because it's not the appropriate time to sell the company. But any ideas on that?

Jessica (00:11:49) - Yes, absolutely. I do run into business owners from time to time. You know that I hate this business and I really want to sell it. And then they sit back and they say, wait a second, I had all these wonderful years, like, this is my baby. I don't really want to give it up. My favorite solution for that is to let you stay in the company. If you would like to doing whatever role you want it is, and then myself and my investors would come in and run the business for you. And you can do that piece that you absolutely love. What I find most business owners want to do when they don't want to exit their business just yet as they like to stay in on the sales.

Jessica (00:12:25) - I am so okay with that.

Josh (00:12:29) - Yeah. So who would be like an ideal connection or someone that's listening to us say, Well, Jessica might help people like me. Can you maybe further define, like, who? Like this kind of ideal connection? Someone that you could really help would be like, what sorts of things? What types of business, you know, that sort of thing.

Jessica (00:12:49) - Right now, we're really looking for businesses that support multifamily units of 48 or better. So that looks like concrete fencing, roofing, exteriors, locksmith painting, those types of businesses. But also I have various different partners that are interested in different avenues. Like one of mine is interested in smaller businesses. Um, like anything that's not food related really, but he loves to market businesses, so he's looking for the smaller mom and pop businesses. And then if it's a business that I'm not interested in particularly, I have a whole network of people that I can send you out to. We can get you some help.

Josh (00:13:32) - Well, that sounds like a pretty great deal. So to so someone's like, okay, all right, all right, all right. What are kind of the next steps for someone that's like Jessica might be able to help me. She might be able to help with some ideal connections.

Jessica (00:13:45) - Go ahead and send me a message through Facebook or LinkedIn. It's very easy to access me. I answer that stuff personally.

Josh (00:13:53) - Yeah, you're. You're just spelling on your name. Jessica. It's Jessica Dragon and drag A if I said that correctly. Yeah, your LinkedIn is great. That's your website. Can't wait to retire. Are there any other resources that you'd recommend? Maybe someone's, maybe not necessarily. They may or may not be ready for a conversation, but they'd love to kind of dive into your world a little bit more.

Jessica (00:14:20) - Yes, I am definitely posting some tips and tricks and exactly what I'm up to and who I am on those social media outlets.

Josh (00:14:29) - Yeah, your LinkedIn is really, really good and in particular, so I'd recommend that as well.

Josh (00:14:34) - Some awesome Jessica Dragan Again, your website can't wait to retire. Jessica Of course. Thank you for your service, your army. I'm Navy. We're friends, we're all good. And Jessica, it's been great having you. Thank you so much for this conversation. Thank you so much for the work that you do in the world.

Jessica (00:14:52) - Thank you. Josh, appreciate you as well. It's always a pleasure.

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