Finding Their Own Way: How New Owners Reimagine a Small Business’s Legacy

Finding Their Own Way: How New Owners Reimagine a Small Business’s Legacy
Sustaining a small business’s legacy is no easy feat. Success requires new owners to build on the legacy of the business — adapting it to both their passions and the changing times.
by Square Apr 23, 2019 — 7 min read
Finding Their Own Way: How New Owners Reimagine a Small Business’s Legacy

Across the United States, small businesses line small-town streets, are squeezed into busy city sidewalks, and are tucked away on quiet country roads. Whether these businesses are passed down to successive generations or sold to new proprietors, they are a part of the legacy of their communities.

Sustaining a small business’s legacy is no easy feat and can be especially difficult as ownership transfers from one generation to the next. Many new business owners are unprepared for the shoes they’re asked to fill. And even those who have planned for the transition meet unexpected challenges in their new, complex role.

Success, then, requires new owners to discover what they are uniquely suited to provide for the business, finding ways to build on the legacy of the business — adapting it to both their passions and the changing times.


Inheriting or taking over a legacy business can come with a range of emotions. Brian Garver became co-manager of Niederman Family Farm, along with his aunt and cousins, when his uncle passed away in 2011.

“Our biggest concern obviously was healing as a family,” Brian remembers. But the business aspect of this loss quickly became critically important. “That was a really big hit for the farm. It’s like corporations losing their CEO. You wonder, ‘How’s it going to work? Are we going to be able to succeed?’ It was like jumping into a cold pool.”

It can be overwhelming trying to fill the shoes of the previous owner — especially when that person was a fixture of the community, which is so often the case with small businesses. Many new owners find themselves motivated by this reputation and a combination of responsibility, passion, and pride in the business.

This was certainly true for Kenji Yick, who took over as manager and head baker at Yasukochi’s Sweet Stop in Japantown in San Francisco, California, when his grandfather, Moses, became ill. “Since none of my grandpa’s daughters wanted to take over, I thought it’d be a nice opportunity for me to step in and keep the family business going,” Kenji says.

The customers are also a factor. “A lot of people would be devastated if we stopped selling the coffee crunch because they grew up on it.” But Kenji is ultimately motivated by his own passions. “It was never really an ‘I’m going to step in and be the savior’ kind of thing. It’s just more that I enjoy doing this. I like making things for people.”

Taking over another family’s business comes with unique considerations. In 1994, Cliff Green and Tony Stovall were offered the opportunity to become co-owners of Hot Sam’s — the oldest men’s clothing store in downtown Detroit and the very store where they had been salesmen for decades. “If the original owner had to go outside of his family, then he wanted to sell it to me,” Tony remembers. Their hard work and dedication put them in a unique position to buy the store and carry on its tradition — the epitome of the American dream.

Although Cliff and Tony had friends tell them to change the name to reflect the new ownership, they chose to maintain the name that had kept the store successful since its inception in 1921.

“I learned a lot from the previous owner on how to be a businessman,” Tony reflects. “And by keeping the name, I didn’t have to reintroduce myself to customers or vendors. They already knew my presence. That part of the legacy was great, and we were able to add to that legacy and hopefully make it better.”


Regardless of how a person comes to acquire a small business, there is always a period of adjustment. While many new business owners find themselves in their new position quite abruptly, some have the benefit of a transition period with the previous owner.

Brian’s ascent to farm manager came suddenly, but having grown up on the family’s farm, he’d been learning about the responsibilities involved in running it for decades. He began around age eight, filling grain buckets for two cents apiece. Next he was able to start feeding the animals — making sure they had milk, grain, and hay. By the time he was 12, he was milking cows, which he did until he left for college.

“It instilled that quality work ethic because I realized if I didn’t do the job right today, then tomorrow that problem is going to compound itself.” And his uncle helped him along the way. “With every step comes more responsibility, the potential for more loss or cost. And I made mistakes. Kids do — you mess up. But the greatest thing about my uncle was that he would say, ‘OK, what did you learn from that?’”

Agustin Gonzalez is the second-generation owner of A.G. River Wood Windows and Doors, a company that makes wooden windows in San Francisco. Similar to Brian, he started learning the craft from his dad when he was young.

“As a kid, I had my own little workbench in the garage, and I used to go with him on job sites.” In high school, instead of playing a sport, Agustin would run home after school to help his dad work. “A lot of our customers today have known me since I was a little kid.”

While this familiarity helped ease the transition when Agustin’s dad died, it was still a tough time. “The transition was hard because my dad passed suddenly. The inside office work was especially difficult because he didn’t have an office manager. He was a one-man show.” Today Agustin works to ensure no aspect of the business is dependent on a single person.

When Moses’s health began to decline, he started mentoring Kenji on how to run the business. “He did kind of ease me into it,” Kenji says. For example, Moses would have Kenji determine how much cream to order for the week. And even still, the transition was, at times, overwhelming. “I just came in here with no experience at all. ‘Here you go! Deep end. Try not to drown.’”


What might initially be a matter of survival, necessity, and a way to keep a legacy alive can change as the new business owners settle in and determine a sustainable path forward. The goal for most small business owners is the same: to preserve the business and carry on the legacy — for themselves, for their families, and for the community.

“The most important part is making sure I stay faithful to my grandpa’s legacy,” Kenji says. “And making sure the people who want the coffee crunch can still get it.”

Brian reflects on the rarity of a family farm — one reason he is motivated to continue the business. “I think the family farm, as a general rule of thumb, is really a concept of 50 years ago,” he says. “A lot of the farms that are around now are mega farms. That’s awesome because they’re producing the food that we need, but there’s something very unique about a family farm.”

As new business owners work through the stress and potential kinks of taking over a business, they are able to start thinking about more than just the day-to-day operations. New owners must ask themselves how the business needs to change to remain viable.

Implementing technology

For many businesses, the path forward involves combining the old way of doing things with new tactics and technologies — preserving the craft but modernizing their processes.

Kenji knows that technology will be a part of the future of Sweet Stop — but only after his grandparents retire entirely. “I guess the best way to put it would be to say that they’re technologically phobic,” Kenji laughs. But he intends to one day build out the shop’s website, take online orders, and move all orders to a computer system to reduce lost or mistaken orders and make the process smoother overall.

“Our trade is still done by hand,” Agustin says of the company’s windows. “So it hasn’t really changed much.” But to help them meet the demands of customers today, Agustin’s wife, Grace, began using QuickBooks to track orders and Square Invoices to manage their accounting. “One important lesson my dad taught me was that your customers are your bosses,” says Agustin. “You always treat them right and try to be honest with them.” So when his customers implored him to accept credit cards, he found a way to do it. “I think [accepting credit cards] helped us thrive … or else we probably would have suffered financially.”

Agustin has also moved the business from paper to digital advertising. While his father advertised in the yellow pages, Agustin posts photos of their work and videos of the crews having a good time on social media to demonstrate not only their craft but also their personality. “That’s the advertising we do nowadays,” he says.

Bridging the old and new customer

While Agustin is still making the same windows his family has for generations, some owners see a path forward for the business with a shift in product offerings.

At Hot Sam’s, Tony’s and Cliff’s children help them maintain the business. Lauren Stovall, Tony’s daughter, has worked hard to reconceive the business’s look and products for a younger customer base.

“I spearheaded the in-store makeover where we pulled up the carpet, we painted, we changed the layout,” she recalls. “Aside from that, what I really try to do is change some of the inventory. Because we’re the oldest men’s clothing store in downtown Detroit, I don’t want us to look like the oldest men’s clothing store in downtown Detroit.” Sometimes this work includes convincing Cliff and her father that this shift is necessary for the business to continue to thrive. She explains that the owners tend to think the current approach to business is working just fine. “It is working, but it could be so much better,” Lauren says.

“To grow your business, you have to reach out to a new generation,” Cliff says. “So we’ve made some changes. We’re listening. And we’re still trying to retain the customer that has been with us for 30 or 40 years.”

Pivoting the business model

Many new business owners reconsider the long-standing business model, either because of economic realities or changing times.

Brian remembers the tough decision to expand beyond just the typical daily operations of a dairy farm to cater to their customer base and continue to support the family financially. “Our family loves this area, and we never really wanted to just sell and move away to do this somewhere else. We were born here, we were raised here, but what do you do when it costs more to feed your cows than what you’re getting paid for the milk that they’re producing?”

To make up this profit, the farm now offers agri-entertainment, including a corn maze, a fall festival, farm tours, and paintball. “When you’re deciding to plow under a field that you planted crops in to make it a paintball field, you wonder if it’s going to work. But the necessity of it also kind of propels you to take that next step.”

Determining the best path forward for an established business can be a lot to live up to, and certainly a lot for new business owners. They must balance this new direction with the elements that make the business what it is, that have made it both an important part of the community and an important part of the family — even when the business has been passed to a new family.

“Our goal is really just to maintain the integrity of this farm unit in this community as long as we can,” Brian says. And that’s what these businesses strive for — continued success and to see another generation of owners get the opportunity to make their mark.

The Bottom Line is brought to you by a global team of collaborators who believe that anyone should be able to participate and thrive in the economy.


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