Key takeaways
- An owner must work on the business as well as in it.
- Getting support from experienced advisers and other owners likely would have created a smoother transition.
Lessons learned
- Introduce the new owner to managers one-on-one to ensure a smooth transition
- Hire more staff to relieve your own workload
- Engage in support groups
- Be honest with the buyer
About the storyteller and business
Storyteller: Business founder/seller
Business location: Metro
Industry: Retail
Business type (storyteller's view): Woman-owned
On this page
- Introduction
- Background
- Launching the business
- Reaching burnout
- The decision to sell
- The sale
- Challenges of the transition
- The days of post-ownership
- Advice
Introduction
This is a story of a successful entrepreneur, Ava Jones, who started a retail children’s clothing boutique and grew it to four locations over 14 years. Then life happened; her mother suffered a stroke, and she wanted the flexibility to be able to spend time with her mom if that was needed. At the same time, Ava was burning out from the stress of always thinking about her multi-store business, day and night. Around 2019, Ava was able to sell the business, all four locations, to a buyer, Colleen, who wanted to leave her corporate career behind. Colleen’s move into small business ownership after big business is sometimes called “encore entrepreneurship”. Note that the names of the seller, buyer and the business have been changed.
Background
Ava had begun to weigh her options. She had just left her job of more than four years where she had a horrible boss. She tried working somewhere else, but it just didn’t feel right to her. She was at a crossroads, and she felt she needed to head down a new path. Then, she had an idea: why not start her own business?
At first, she wasn’t sure what the business would be, but she was sure she could pull it off. At the time, Ava was in her early thirties, so a lot of her friends and family were starting to have kids. She found herself shopping at the same big box stores and chains, and she wondered why there weren’t any other options. There were some small boutiques in town, but they were what Ava referred to as traditional “Grandma oriented” type shops. Their baby clothes were lacy and frilly, not exactly what Ava imagined young moms were looking for. To Ava, this was an opportunity. She saw a need, and just like that, she had her business: a modern baby boutique.
Ava didn’t need to do much to prepare. She worked at Crate and Barrel for six months to make sure that she didn’t hate retail, and then she went for it.
Launching the business
While she was trying to get the business off the ground, Ava says she did something unwise — she took out a home equity loan to fund the business. She didn’t think anything of it at the time but has since learned it was not the best idea.
“At the time, my reasoning was, well, if the business goes under, the worst that happens is I lose my house, and I move in with my parents.”
— Ava
When Ava’s dad found out that she had taken out a home equity loan to open the first store, he was horrified. In their family, they never took out loans for anything. He immediately gave Ava the money she needed to pay off the loan and told her to pay him back as she could. Later on, Ava realized that her dad was forgoing the interest on the money he loaned her. Ava was grateful.
Because of his favor, Ava didn’t face the normal funding issues that bog down so many small business owners. But, according to Ava, that was just what her family was like. They always told her to never take out a loan if she could just bootstrap it, so Ava never took out a loan again.
Reaching burnout
After 14 years in the business, Ava was getting burnt out. She was reaching the point where she just couldn’t do it anymore.
“I was always thinking about the business. I was waking up at two every morning and thinking about the business and how to improve it, day and night.”
— Ava
Then, Ava’s mom had a stroke. She was recovering, but it forced Ava to ask difficult questions about the future. What would happen if her mother suddenly needed more care? What if Ava needed to spend more time with her? Ava’s worst fear was not being able to be there for her mother when she needed it. The business was important to her, but her mother mattered more.
The decision to sell
The business had grown to four locations. A couple years prior, Ava had asked one of her managers, Erin, to co-own a location with her. She was looking to open a new store, and she wanted to give her employee the opportunity to own it with her. Ava offered to fund the opening of the store and help get her started. Then, Erin could manage it and take ownership of half the store. They both decided to go for it, and for a while, it went really well. However, small businesses, especially retail, don’t make a lot of money. More so, they take an overwhelming amount of work to make the business run. Erin ran the store for two years, but after that, she was running out of steam.
“And I was like, great. I’ve always wanted to sell a business. Do you want to try selling it?”
— Ava
Ava wasn’t fazed by Erin’s decision to leave the business. She knew how much work it was, and she completely understood wanting a break from it all. Besides, Ava thought it might be nice to sell one of the stores. That way, she could lower some of the workload and get some cash in the process.
Erin, who would receive half of the proceeds of the sale, agreed.
Ava contacted one of the big business brokers in town, and he helped the two of them list the location for sale. Ava gave him all the financials, and from that, he named a price and listed the business. Only one location was listed for sale. Ava planned on continuing to own and run the remaining three locations as is, not necessarily because she wanted to, but because she figured no one would ever want to buy all four. At the end of the day, she was just looking for a buyer who could afford to buy one location, and that’s it. She couldn’t believe it when, after about six months, a buyer came forward who wanted to purchase the entire business.
“I didn’t think anybody would ever want to buy all four [ … ]. Because if you know how much work goes into it and how much money you make, you’re like, ‘No way. You’re crazy.”
— Ava
Ava was not expecting to sell all four locations, and she was hardly prepared for it. However, the more she thought about it, the more it appealed to her. She thought about her mom and the stroke she had a month prior. She thought about her parents getting older and the time she wanted to spend with them. She figured, if someone wanted to buy all four, why would she turn that down? Ava was burnt out, and at the end of the day, she thought this could be a sign that she needed to move on.
“If someone wants to buy all four, sure, we will sell all four. But I kept waiting for the deal to fall through.”
— Ava
Even with the offer, Ava couldn’t shake the thought that the deal was going to fall through. She figured that once she showed the buyer the finances, she would never want to buy it. There was barely any profit to be made, so who in their right mind would want to buy into so much work? However, Ava’s fears never came to fruition. The buyer, Colleen, was truly interested, and the small margins of the business did not seem to scare her away. Colleen was prepared for this. She was a graduate of the University of Minnesota Carlson School of Management and had spent her career working for Fortune 500 companies. Not only did she have the experience, but she had a plan to grow the business in a way that Ava never could.
Colleen saw an untapped potential in online sales. Ava had done some online sales before, but it was a simple “buy online and pick up in store” model at all four locations. She didn’t have a formal business background, so furthering an online model did not really occur to her. They did Google advertisements and everything they could, but they had to figure it all out as they went. Ava understood that Colleen could introduce a more structured way of growing a company in a way that she couldn’t. Colleen had the experience, the funding, and most important, she wanted to maintain the style and aesthetic of the business. She wasn’t looking to completely remodel the company; she just wanted to grow it, while keeping the things that worked. At the end of the day, Ava was just looking for a buyer who could afford the business and keep staff jobs.
However, she did feel comforted by the fact that the buyer wanted to keep the brand as it was. Ava realized the stores were ready for a bit of a change, and it was a good time to put the business into new hands to reach the next phase. She knew the sale wasn’t just a good decision for her but also for her staff and for the broader community. Ultimately, having a buyer she trusted allowed her to put her worries at ease.
The sale
Once Ava had a buyer, it was time for the real challenge: the sale. Ava and Colleen made the deal in the fall, and they did so with little issue. That following spring, however, the city announced a huge construction project that would rip up the street in front of one of the store locations and introduce a huge new development. Not only would this mean a big, unanticipated development, but it also meant there would be three to five years of construction directly in front of the store. Clearly, this project was going to have major repercussions on the success of the business. Colleen, however, was still interested. Ultimately, she just wanted to work out some concessions and figure out how to structure the deal to minimize her own risks.
In these situations, some may find it helpful to have a business broker, or another business succession and transition advisers (e.g. accountant, attorney, exit planner, personal financial planner, etc.) to work out the unexpected complications that can sometimes arise. However, Ava says this wasn’t how it worked out at all. In Ava’s eyes, the business broker she hired was only interested in making a quick sale to get his commission. To her, it was clear he was not concerned with the success of either her or her buyer. So, Ava took the matter into her own hands. She met with Colleen herself, and the two of them talked through the issue and resolved it themselves. By the end of it, Colleen told Ava that she shouldn’t even pay the broker, who had done basically no work at all. Ava understood, but at the end of the day, she was just happy it was over with.
Aside from the broker, Ava didn’t seek support from many other people. Ultimately, she was too buried in the work to be aware of the support network that was available to her. She went online and searched how to sell the business, but truthfully, her preparation did not go much further than that. While she often sought advice from an online group of other children’s boutique retailers from across the country, she didn’t seek out their advice on the sale. She knows their advice might have been helpful at the time, but she couldn’t risk putting it out there until the sale was official.
Ultimately, Ava’s biggest fear throughout the whole sale was that it would not go through at all. If the sale didn’t go through, what would she do? How much longer could she run the business? She was so burnt out, could she even wait another year?
Challenges of the transition
After the sale was completed, Ava and Colleen still needed to transition their leadership. While the transition of ownership is complex in its own right, the transition of leadership can raise even further complications. For the new buyer, the biggest challenge was gaining the trust of the staff, which can be very difficult. Before the transition, Ava had tried to prepare the staff to prevent any issues down the line. Before the announcement was made publicly, she sat down with them to ensure they heard the news straight from her. She made herself available for any questions, and she attempted to address their concerns about what to expect, what was going to change, and what was going to stay the same. After they talked through any uncertainties, Ava brought in Colleen to discuss any questions as a whole group.
Unfortunately, these conversations weren’t enough to suppress any conflict. Fundamentally, there were a few staff whose personalities didn’t mesh with Colleen, and they resisted her new leadership. In the end, she lost some high-level managers. Ava stayed on for a month after the sale in order to help with the transition, which she felt wasn’t much time at all. She could tell the staff conflicts were especially stressful for Colleen, so she tried to mediate and smooth out the issues. However, it didn’t exactly work out the way Ava planned. In the end, some of the staff were upset with Ava for “taking sides,” when all she wanted to do was protect the business.
“If I am on a side, I am on the side of helping the business.”
— Ava
Ultimately, Ava says, everyone just wanted the business to succeed. They all had the same goal, but sometimes, personalities got in the way. In some respects, Colleen just wasn’t accustomed to the culture of small businesses. She came from a Fortune 500 background, where there is a culture of hierarchies. In big business, there is a clear division of responsibilities and a structure of how you must speak to your manager. But, in a small business, things don’t work exactly this way. In a small business, your staff are your family.
“In a small business, your staff are like family, and they expect to be treated like family. That’s why they stick around. That’s the only thing you can really offer them. Otherwise, they would flee for the higher salaries of the corporate world.”
— Ava
Leading up to the sale, Colleen asked Ava what the most difficult part of running the business was. Ava told her the hardest part was hiring and working with a small staff with very strong personalities. Since the staff were integral to the business’ success, it was important to make them feel valued and to carefully navigate their social dynamics. Colleen thought her experience in HR and marketing had prepared her for this, but she had failed to realize just how unique the environment of a small business really was. The small business work environment is truly unlike any other, Ava says, and you really don’t know it until you experience it.
The days of post-ownership
“It took me a long time to really get used to the idea that I was no longer responsible for the business and that I was really done with it. Every time that my phone rang, still for at least the next year, my initial reaction was always, ‘Oh, what’s wrong now?”
— Ava
When it was all said and done, Ava felt relief. She didn’t regret the 14 years she spent owning and growing the business, but she knew the time had come for her to move on. She cared for the business, but she had reached a point of complete and total burnout. Ultimately, she was just ready for some relaxation, and to finally disconnect from that lifestyle.
“I had a dream last week that I still co-owned these businesses, and it was the worst dream ever.”
— Ava
Ava says she maintains a very positive relationship with the buyer, and she feels very lucky to be able to say that. In her eyes, she truly found the best buyer possible, and she is grateful for that. Throughout the past five years, Colleen has never reached out to Ava with questions. Ava figures Colleen must have found some things within the business that don’t run as well as she would have liked, but she never complained. It has been seven years since the sale, but Ava and Colleen still meet once a year to talk things through. For Ava, this relationship has been crucial to making everything about the transition easier.
Today, Ava brings the experience of owning a small business into her everyday work. Through her job, Ava engages with a lot of small and underserved businesses in the community, and the experience of owning a business has really helped her understand where other businesses are coming from. When planning events or workshops, Ava can use her experience to consider the needs of business owners. She asks herself if she was a business owner attending this event, what would she expect from it? What time of day and length of event would work? Are they asking too much of business owners? Without her own experience running a business, these questions may have gone forgotten. Instead, she is able to bring the lens of small business ownership to her career. When she speaks directly with business owners, they quickly realize that she just “gets it” in a way that other people can't.
“Nobody knows what it's like to own a business unless you have owned a business.”
— Ava
Advice
Introduce the new owner to managers one-on-one to ensure a smooth transition
The new owner faced a number of conflicts with staff as she took over Ava’s place in the company. In retrospect, Ava believes that facilitating one-on-one meetings with the new owner and the managers could have prevented some of these conflicts.
Hire more staff to relieve your own workload
After owning and working in the business for more than a decade Ava felt completely burnt out. Looking back, she wishes she had hired more staff to take over some of her tasks and prevent burn out. It would have also allowed her to spend more time working on the business and not just in the business.
Engage in support groups
From her job, Ava now knows that there is a wealth of information and support out there for small business owners, but she wasn’t aware of it when she needed it. She was so buried in working in the business that she didn’t engage in any support groups, but looking back, she wishes she did.
Be honest with the buyer
When negotiating the sale, Ava was completely honest with the buyer about the financial situation of the business, and she’s glad she was. In her eyes, it’s best not to paint a pretty picture and have the buyer taken by surprise. Instead, she recommends upfront honesty, ensuring the buyer has all the information necessary going forward.
Reviewed in 2026