Key takeaways
- Learning the business as general manager set him up to own it.
- New owners need to find their work-life balance and ways to handle the anxiety of ownership.
A business succession and transition (BST) case study
Storyteller: Buyer
Business location: Rural
Industry: Outdoor recreation
Note: The names of the buyer and the business have been changed.
On this page
Background
Entrepreneurship was all Patrick Conroy knew. Growing up in Northern Illinois, both of Patrick’s parents were small business owners. His father owned a local bar, and his mother owned a Sicilian restaurant. As a result, Patrick grew up in a household shaped by determination and a strong work ethic. Many nights, his family wouldn’t eat dinner until 10 or 11 o’clock when his parents finally closed up shop. Whether he knew it or not, Patrick carried this culture of entrepreneurship with him when he left for college.
At Illinois State, Patrick started his own small business, a custom screen printing company for the Greek Life on campus. Patrick was only a sophomore in college, yet he ran a business right out of his dorm room. While Patrick managed the business during the school year, the summers were spent doing what he really loved: exploring the outdoors. He got a job as a summer seasonal helper at a full service canoe outfitter in Ely, Minnesota. They provided guides, rental equipment, lodging, fishing gear, food, and pretty much everything else you would need to do a back country canoe trip. But most importantly for Patrick, he could fish.
Once the summers were over, however, he went right back to school at Illinois State, a college town "surrounded by nothing but corn.” Patrick couldn’t see himself living his whole life in a town like that, so when he graduated, he sold his business and moved to Milwaukee. There, Patrick got a job as an engineer, partly because he thought that is what he should do. However, Patrick didn’t last very long there. His summers in Ely were hard to forget, and something told him that the Boundary Waters was where he should be so he listened.
Pathway to ownership
When Patrick moved back to Ely, he was looking for a more relaxing lifestyle than the one he had as an engineer. He wanted to be back in the outdoors and back doing what he loved, and he knew exactly where he had to be. Patrick got a job at the same full-service canoe outfitter working as the general manager, but he didn’t plan on moving beyond that. After all, he was looking for a more relaxing career path than the one he knew, and business ownership has never been known for relaxation. However, Patrick had an itch for entrepreneurship that he couldn’t seem to shake.
While he worked as the general manager, he created a number of small business side hustles, making tackle kits and other supplies for guests going into the Boundary Waters. Over time, Patrick’s itch grew, and he wanted to start his own business. He wanted to offer services beyond what was offered at the outfitter, like hunting and ice fishing, where his passion really lied. The owner, however, had a different idea. He told Patrick it was time for him to take over the business, and he might as well bundle all his ideas into one. This way, Patrick wouldn’t have to build his own business from scratch. Instead, he could expand on what his boss had already created.
When I moved to Ely, I never thought I wanted to own a business, but I almost couldn’t help myself. I moved up here to live kind of a more chill, relaxing life. That lasted about six months, and then I got bored.”
— Patrick
Patrick agreed, but he was nervous. At first, this was all just an idea, but now it was real — he had to run this business. When Patrick saw the books for the first time, he was overwhelmed. He had always been good at running a personal budget, but a budget of this magnitude was intimidating. The fears began to surface. Patrick wondered if he was throwing his life away. What if the business goes belly up? Patrick knew he had to shut down his fears to move forward.
The first thing you have to do is figure out what you can control and what you can’t control. And anything you can’t control, you have to stop worrying about. Otherwise, it will just consume you.”
— Patrick
It was important for Patrick to understand what he could and could not control, especially in this business. That meant navigating a lot of aspects that could not be controlled, like wildfire, federal regulations, and Forest Service permits. These could all play a huge factor in how the business operates, but Patrick had to let those anxieties go.
The transition
After years of working together, Patrick and the previous owner were more than just colleagues — they were friends. Because of this, Patrick says that a lot of the transition felt like more of a gentleman’s agreement rather than a business transaction. They trusted each other, so a lot of the time, they felt like they could move through the transition without everything set in stone. Patrick didn’t have the finances to go to a bank right away and get a traditional bank loan, so he made the purchase under contract for deed. Essentially, Patrick paid the previous owner directly in installments, rather than obtaining a mortgage from a bank. While the previous owner retains legal ownership of the property until the full purchase price is paid,
Patrick immediately took possession and was fully responsible for the operation of the business. Each payment that he makes to the seller during this period reduces what he owed and increases his equity in the business. Patrick and the previous owner had initially planned for three years of the contract-for-deed period, but the business did better than expected with the work that Patrick put in. Because of this, Patrick built equity faster than anticipated, and he felt ready to go to the bank sooner than he thought. That equity he has built up through paying the seller will act as his down payment when he goes to the bank. Now, when he goes to the bank, he can show his track record of running the business, his financial statements, and the equity he has already paid in.
According to Patrick, after the pending 2026 canoe season, he believes he’ll be ready to go to the bank and wrap everything up. After that, the contract-for-deed will be converted to a traditional bank mortgage, and Patrick will have full legal ownership of the business.
Going into the transition, the previous owner was not only Patrick’s friend but his advisor. He was there for Patrick to spitball ideas, to walk him through the finances, and to give him advice for the day-to-day running of the business. However, he wasn’t the only one who was there to walk Patrick through the process. Patrick also received a lot of help from a city councilwoman in Ely who worked for an organization that helps entrepreneurs get technical assistance and financing. Although she did not assist Patrick with financing, she did help Patrick look through the profit and loss statements, review the purchase agreement, and let him know what questions he should be asking. He said it was a relief to have a second set of eyes on everything.
For Patrick, working at the company as an employee prior to ownership was crucial for his transition to owner. Because of the time he had spent as an employee, Patrick knew the business intimately from his experience on the ground. When he took ownership and looked at the numbers, he understood why one number may be low (they had cut corners there) or another high (they had canoes break that year). He understood the business in a way an outsider could not, which he believes became an irreplaceable advantage for him. Also, by becoming a friend of the previous owner, Patrick and the former owner were able to move through the transition not just as business partners, but as friends. Patrick says the previous owner has helped him learn a lot of things he hadn’t been taught in school, like the accounting software, which was very helpful. While the previous owner remained a sounding board if Patrick had questions, he did not formally stay on after the sale was final. Patrick took over all of the operations of the business at that time.
Growing up with entrepreneur parents, Patrick had an additional built-in network of support and source of advice. Having experience running their own small businesses, Patrick’s parents were always there to give him advice. Patrick said his parents made the mistake of paying down their loan too fast. They didn’t set aside any money for savings, so when they had a bad year, they didn’t have any money to fall back on. Patrick’s dad didn’t want him to make the same mistake, so the first thing he advised Patrick to do was to build up a rainy day fund. Patrick said doing so helps him sleep at night, knowing he has a safety net if he needs it. Even though he would save some money if he paid the loan down faster, he feels like it's more important to have money to fall back on.
Even though he was well prepared, the transition into ownership did not always go smoothly for Patrick. Since a lot of the financial aspects of the job were completely new to him, he was bound to make some mistakes. When Patrick first started pulling their reservation tracking, he thought the amount listed was after fees. By the time he realized it was actually before fees, it was too late. He had completely miscalculated his budget, and he was falling short. It was scary in the moment, but at the end of the day, Patrick thinks he worried about it more than he needed to, and everything ended up working out just fine. Patrick just had to book more trips to make up for the loss, which was the advice his boss had always given him.
He said that the key to success was butts in beds and butts in boats. If you’re renting something, it shouldn’t be sitting there, it should be on the water.”
— Patrick
Growing the business
People say that money doesn’t solve all the problems. But […] owning a business, money solves a lot of your problems.”
— Patrick
When buying a business, Patrick says it’s important to immediately have a plan for growth. Otherwise, he says, you are just buying yourself a job. Further, once you take ownership, growing your business means increasing the value of your largest financial asset. It’s almost like contributing to an IRA, Patrick says, because each year that he works hard he contributes to a substantial retirement asset for himself. Ownership means that he is no longer just working for a salary—he is also building something that he can sell one day. Every time Patrick makes a loan payment, he remembers these payments are an investment in his future. Knowing all this, Patrick wanted to grow the business as quickly as possible. He had a plan going in, and he did not waste any time implementing it. Right out of the gate, Patrick transitioned the business from a summer destination to a full three-season outfitter. This way, he could take in as much business as possible. Next, Patrick increased the payroll and doubled the marketing budget. To make up for the increased expenses, Patrick personally took a 50% pay cut going from general manager to owner. He made sure he could still pay his mortgage and all his basic expenses, but that was it. For the next year, he cut out all personal spending and devoted every spare dollar to the business. It was important to Patrick that the outfitter was as busy as possible in year one, and he was willing to make sacrifices to make that happen. In the end, Patrick thinks this was the right move. Ultimately, it helped him understand what his costs would be if he wanted his business to be successful.
Figuring out what your costs are is kind of a battle in itself.”
— Patrick
Increasing the payroll and the marketing budget on day one was huge for the business, Patrick says. With a brand new marketing campaign, the business saw 60% growth in year one. On top of that with a bigger and more knowledgeable staff, their Google reviews doubled during that first year. Patrick had a five-year plan for growth—and it all happened in the first six months. Patrick was also proud of what this growth meant for his staff. With this substantial growth and a three-season model, Patrick was able to hire his staff year round. The local economy in Ely is largely reliant on the summer tourist season, with low demand in the winter. It was really important to Patrick to be able to pay his staff all year long and give them the opportunity to stay in Ely full time. This way, they did not have to find odd jobs in the winter and could focus on the outfitter full time.
Growing the business wasn’t easy, though. Patrick found himself with a lot of new responsibilities that he wasn’t accustomed to. He had to cram multiple roles into one job, and most days, there just wasn’t enough of his time to go around. Once Patrick became in charge of finance and marketing, his previous duties were often pushed to the side. On top of dealing with customers day to day, Patrick also needed to manage all of the office and clerical work, redesign the website, and lead a new marketing campaign. Because of all this new marketing, the business was also busier than it ever had been before. While the previous owner was more selective with the trips they booked, Patrick wanted to book as many as possible. Patrick figured that he just needed to book the trip, and then he would figure out how to provide the service. At the end of the day, he would figure it out. If he had to wake up at four o’clock in the morning to drive canoes somewhere, then that is what he had to do. He would do anything he needed to do to get trips through the door. However, Patrick’s time was stretched thin, and he realized that he couldn’t do it all by himself. Going into year two, Patrick hired an additional manager to help balance the workload and allow the business to grow even more.
Still, the stress and anxiety got to Patrick. He says he knew it was going to happen no matter what. The only thing he could do is learn to manage it, and it took a little while for him to figure that out. It was difficult for Patrick to leave work behind when the day was done. He found that, even after he went home, a part of his brain was always focused on the business. And now, with technology, it’s easy to work wherever you go. Patrick had his email, his Google analytics, and everything else he needed right in the palm of his hand. Over time, he had to learn how to balance work with his personal life and set hard stops at the end of day. Still, Patrick knew the reality of business ownership is a fragile work-life balance. As the owner, you always have to be available, especially when there are clients there. If someone needs something or if something goes wrong, Patrick is the person they call. The reality, he says, is that you’re going to work, so you just have to learn how to balance it with your lifestyle.
I was never able to fully leave the business. Forty percent of my mind was always there.”|
— Patrick
For Patrick, though, it’s all worth it. All the late nights and early mornings are worth it because he loves his job and where he lives. It is more than a job for him, but an opportunity to do what he loves every single day. Right from his office, Patrick can be hunting, fishing, hiking, cross country skiing, or paddling, all within 100 yards. That is what brought him to the Boundary Waters, and that is what gets him to work every morning. There are plenty of other things he could be doing if money was the goal, Patrick says, but he isn’t interested in that. At the end of the day, he is just grateful he is able to pursue his passions as a part of his career.
You don’t do this to get rich.”
— Patrick
The future of the business
For Patrick, owning the outdoor recreation business is not just a stepping stone but also his plan for the long term. Ideally, Patrick would run the business until he retires, continuing to improve and grow the business. These first two years of ownership have been a whirlwind, so he hasn’t thought much about transitioning the business to another owner yet.
Growing the business has been the focus, so he hasn’t had much time to consider what the business might look like after he’s gone. However, when he does retire, Patrick says he wants to give someone the same opportunity that was given to him. He doesn’t just want to sell the business to the highest bidder. He wants to pass it on to someone who worked their way up the company just like he did. Patrick has worked hard to grow this business, so he wants to give it to somebody who shows the same passion and entrepreneurial drive that he did. For Patrick, that is the only way it would feel right.
Reviewed in 2026