Sixty-five years, more than 70 stores and a diversified approach to business add up to a family business success story for the Riddle family.

Founded as a single jewelry store by Jesse Riddle in 1959, Riddle’s Jewelry became an equal partnership in 1961 with his brother, Bob. The Rapid City-based business now is in its third generation, with locations in 10 states and a thriving factory that supports more than 1,200 jewelers nationwide selling diamond, gemstone and Black Hills gold jewelry. The family also owns four glass shops and is continuing to expand its offerings of doors and windows supporting commercial building.

“Our father (Jesse) worked for a jewelry store in high school and was told he wasn’t capable of running a store himself,” said Brett Riddle, who serves as president, CEO and managing partner.

“You don’t ever want to tell him he can’t do something.”

The second generation, which includes Brett’s sister, Tamara Riddle Schumacher, an equal partner who oversees the factory and serves as board chair, entered the business in 1990.

“At that time, we had 23 family members in the business,” Brett said. “But my dad was really smart because he spread us out through different areas.”

At that time, their father became a founding member in the organization that would become the Prairie Family Business Association. Jesse Riddle served on the association’s board of directors for eight years, and Brett would go on to serve on the board for four years. The family also has connected other family businesses to the Prairie Family Business Association, and now the family’s own next generation is benefiting from its resources.

The Riddle family recently hosted the Prairie Family Business Association’s Next Gen Retreat at its K Bar S Lodge in Keystone, with three of its own future leaders attending. Brett’s son, Jesse, is a regional manager. Tamara’s son, Dominic, manages the company’s outlet store in Rapid City. Loren Jensen, the grandson of Bob Riddle, is the director of the company’s corporate office.

“It was really good, especially because I’m a little older than Jesse and Dominic even though we’re all part of the third generation, so it helped me get a perspective on where they were at in the business and what their goals were,” Loren said. “It brought us closer together.”

The retreat, which was a second one for the trio, “bridged a gap,” Dominic agreed. “We all knew each other outside of work, but we got to know each other on an even more personal level with both of the retreats.”

The family’s lodge also worked well for the event, Dominic said.

“It was really good. We were able to set up a lounge area for people to talk and meet each other, which I think they really enjoyed.”

The family bought the property near Mount Rushmore in 2004 when it was one building that offered dinners for groups and since has expanded with meeting rooms, a large dining room, a hotel and a venue for weddings.

“My father’s dream for this property was to expand it, and now that’s what we’re planning to do,” Brett said. “We’ll be adding villas, a pool and pickleball court to really create the resort he envisioned.”

The Riddle family also participated in a panel during the two-day event in which they shared their own experiences as a multigenerational business, including their experience with transitions.

“For us, it’s very exciting and special that the third generation is coming into the business,” Tamara said.

“Our business has been around 65 years, and this means the legacy will continue. Throughout all those years, there have been great times, tough times, sacrifices and risks that each generation took or will have to take. It’s not a perfect journey, but it’s a journey well worth taking with your family, and hopefully someday we’ll move into the fourth generation.”

The second and third generations look forward to many years of working together, Brett added.

“We set expectations for our next generations coming into the business, and now we’re working with them to help them learn the business and earn the respect of our team,” he said. “They’re learning to become leaders here.”

Since attending the Next Gen Retreat, the third generation is meeting regularly. They encourage other family businesses to attend the event multiple times.

“The first time can be a little overwhelming as you try to figure out the right things to ask, and this was a little more comfortable and allowed us to branch out and talk more with others,” Loren said.

“Now, we’re setting meetings up for the three of us, along with time to meet with the second generation to talk about questions we have and setting it up so we work well together as we grow.”

That includes making time for fun, Dominic added.

“We’ve tried to schedule things like golf together to bond that way outside of work as well,” he said.

The second generation noticed a change afterward too.

“They seemed to have a deeper connection with each other,” Tamara said. “They wanted to spend more time with each other and get to know each other outside of the business.”

That’s a common benefit of the Next Gen Retreat, said Stephanie Larscheid, executive director of the Prairie Family Business Association.

“This retreat is such a valuable time to tap into expertise but also to hear from other family businesses with relatable situations and get to know your own family better,” she said.

“The Riddle family is such a strong example of family business success. We were grateful to them for hosting the retreat and for sharing their story with our members.”

For other family businesses looking to strengthen their next generation of leaders, the Prairie Family Business Association offers a range of programs, including Affinity Peer Groups — exclusive groups designed to connect family business members with peers facing similar issues. These groups offer invaluable opportunities to share experiences and provide accountability. The third generation of the Riddle family is engaging in a regional affinity peer group.

To learn more about joining an Affinity Peer Group and other programs that support family businesses, contact the Prairie Family Business Association at fba@usd.edu, or click here and take the next step in ensuring your family business thrives through generations.