The US population is aging. Sometimes called the ​“silver tsunami,” the Baby Boomer generation is entering retirement, creating a widespread shift in the national workforce. For Main Streets, this represents a particular challenge as many institutional small businesses are owned by soon-to-be retiring Boomers. In fact, an estimated 15% of Main Street businesses in our network are considering selling before retirement in the next five years, but most aren’t sure where to start.

Main Street business owners in small towns have the additional challenge of a limited market in which to transition their business or are family-owned businesses without a next-generation successor. 

Whether you’re considering buying a small business or currently navigating a business succession, these strategies from successful Main Street entrepreneurs will help you thrive as a second-generation owner.

Success Story 1: Mindy Bergstrom, Cooks Emporium | Ames, Iowa

A few years ago, Mindy moved to Ames to be near her husband’s family, and took over as the new owner of Cooks Emporium, a kitchen supply business that had been in the community for decades. 

Here’s how Mindy transformed what was once a kitchen supply business into a thriving community hub:

• The kitchen has a special event every night, from knife-sharpening lessons to cooking classes.
• She partners with the culinary program at Iowa State.
• She launched two more businesses around the corner, a home goods shop called Nook & Nest and a general store called ZW Emporium. 

Key Lessons:

• Show Genuine Commitment: Mindy brought a commitment to become involved in and care for her adopted downtown. This helped build a lot of trust with the folks selling the business. It’s important that the buyer has some skin in the game, not just an interest in the business but a sense of responsibility and ownership in the community.
• Consider Keeping the Business Name: When a business is a beloved part of a downtown district, keeping the name doesn’t just help with continuity. It shows commitment to and respect for the many years the original owner put into the business. For Mindy, it was important to pay tribute to the former owner.
• Don’t Be Afraid of Change: A name can be important, but the best new business owners bring new energy to expand on the creative vision of the original business. Running a business for decades can sap you of new ideas — if a formula is working well, why change it? But like Mindy, the best new business owners know how to take calculated risks in expanding the business. 

Success Story 2: Mallory Dabney, HeyDay | Bozeman, Montana

Mallory Dabney is the owner of HeyDay, a gift store in Bozeman, Montana. Like Mindy, she relocated to her husband’s hometown. Before the move, Mallory worked in corporate marketing and had an MBA, but had never run a small business. Once resettled, she worked as a wedding planner for a few years before starting a retail job in downtown Bozeman. She was a careful student from the beginning, and with her marketing background, she was invested in being data-driven and adapting to shifts in society, technology, and the economy.

When the opportunity arose to buy HeyDay Mallory took it. The owner, Lisa, was willing to be creative about financing to make it easier for Mallory to take over. Lisa also made herself available after the transition to provide insights and guidance, and offer continuity when Mallory decided to rebrand the business. While Heyday had already been a longstanding anchor in the downtown district, Mallory used her marketing savvy to take operations and revenue to the next level. Here’s how: 

• Mallory and her team installed a customer counter that helped them gather data on foot traffic, which then helped them to sales cycles and inform business practices.
• She invested heavily in a ​“bricks-and-clicks” strategy, creating an online store to support in-store sales.

Mallory used her marketing know-how to rebrand the business, creating continuity between the in-store and digital experiences.

Key Lessons:

• Check Your Assumptions: Mallory — and Lisa before her — had always operated under the assumption that there were busy seasons and slow, shoulder seasons. A lot of their business came from tourists, and so there were spikes in sales during the summer and in the month before Christmas. But when Mallory installed the customer counter, the team learned that there was no real drop in foot traffic. They used this insight to revamp their approach to seasonal staffing and focus on converting their foot traffic in those shoulder seasons to sales. So, another important lesson in succession is to check your assumptions with data, especially if those assumptions are inherited from the previous owner.
• Explore Areas for Growth and Change: Mallory’s rebrand of HeyDay was heavily focused on creating continuity between the in-store and digital experiences. We think of Main Street businesses as primarily an in-store, in-person, sensory experience. That’s what we love about them! The ability to carry that experience into a digital presence is difficult to do, but it can really pay off when it’s done well. Mallory invested a lot in ​“bricks and clicks,” a hybrid-but-intertwined online experience and the back-office operations to support it. That’s not just the user experience of the website, but marketing, fulfillment, inventory, and shipping. So many legacy businesses are missing out on e‑commerce or other new growth shifts and pivots that it’s something that needs to be carefully considered in a succession plan.

Success Story 3: Dale Sexton, Dan Bailey’s Outdoor Company | Livingston, Montana

Finally, there’s Dale Sexton, owner of Dan Bailey’s Outdoor Company, a historic fly-fishing shop and outfitter that opened in downtown Livingston in 1938. Having worked there as a teenager in the 80s under Dan Bailey’s son, Dale kept in touch with the family over the years. He went on to run an outdoor guiding company of his own. In 2020, during a pandemic-era surge in outdoor recreation, he bought the company. 

Here are a few ways Dale continued the business’s strong legacy, while digging even deeper roots in the community:

• Dale worked hard to build trust with long-serving and loyal employees, creating opportunities for them to contribute ideas and grow in leadership.
• He invested in contributing to community events and local philanthropic efforts.

Key Lessons:

• Treat Your Employees As Your Greatest Asset: Like the other two businesses, Dan Bailey’s was also a cornerstone of the downtown district with several long-serving and loyal employees. Through Dale’s previous experience as a business owner, he had learned to build trust with employees, creating ways for them to contribute ideas, talents, and leadership. This one may be a no-brainer, but treating longstanding employees as your greatest asset is really important in succession.
• Connect with the Community: Dale also worked hard to expand Dan Bailey’s as a community hub, and to connect it even further into the good things that were going on in Livingston. He hosts the annual Cold Snap Film Festival, which raises significant funds for the local soup kitchen. He works hard to make people’s experience of the business authentic and memorable — whether they are customers or not, and whether they’re locals or not.

All three new business owners built a strong relationship with their local Main Street organization, which helped provide support and guidance during the succession processes. It’s the Main Street’s job to support local merchants by driving foot traffic downtown, providing training and resources, and support business owners during times of transition.

For more insights on small business ownership and succession planning, subscribe to our newsletter to receive updates on small business resources, grant opportunities, and new episodes of the Main Street Business Insights podcast.