A jeweler in small-town Webster, South Dakota saw something promising in a young Jesse Riddle encouraging him to head to Chicago and pursue schooling in jewelry making – a move that would set into motion more than six decades and three generations in the industry.  

“Working for that jeweler is what kind of piqued his interest,” said Tamara Riddle-Schumacher, Jesse’s daughter and the president of manufacturing and gemology for Riddle’s Jewelry.  

Jesse used his skills from Chicago to pay his way through the University of South Dakota, selling jewelry out of a trailer to his fraternity and opening his first store in 1959 during his senior year of college.  

“It’s amazing where we have gone from there,” said Brett Riddle, Jesse’s son, and President/CEO. Riddle’s Jewelry is now in its third generation with nearly 70 stores in nine states with another one in the works along with 1,200 wholesale accounts, a manufacturing business and factory outlet.  

“We are a horizontal as well as vertical business. We are not just in the retail business. No other jewelry company in the country that started in retail has done what we’ve done,” he said.

Jesse’s entrepreneurial drive and focus on people prompted the business to expand in the 1960s. Jesse and his wife, Joyce, joined forces with Jesse’s brother Bob and his wife, Carole. But growing the business was not always easy.  

“In the early years, my dad and mom and uncle and aunt put their homes up for mortgage to fund the business,” Brett said.  

All the money earned went right back into the business.  

“When they first opened the store, my mother worked as an English teacher and they lived off her salary which was $3,400 a year,” Tamara said.  

But despite the challenges, Jesse was never one to back down.  

“You could never tell my dad no or that he couldn’t do something,” Brett said.  

The retail sector expanded quickly in the 1970s and ‘80s with the popularity of shopping malls. In 1989, a new facility was built and along with the factory, the company offices out of Aberdeen and Watertown were moved to one location. 

“Our main business is still selling wedding rings and diamonds,” Brett said.  

And the family loves being a part of all those special occasions. The stories they hear dating back decades are what make them love what they do even more.  

A few years ago, Brett’s son Jesse was working at a Sioux Falls store while attending college. A man came in and told the story of how he bought an engagement ring from a Jesse Riddle in Milbank, South Dakota in 1968. The store had closed, however, Jesse let him in and helped him pick out the perfect ring. The younger Jesse told the man that that was his grandfather.  

“It was very emotional,” Brett said.   

Aside from the jewelry business, some of the family members have also ventured into the hotel and event venue business, expanding the moments they get to share with customers. They own the K Bar S Lodge with a nephew, Jordan Olson, as the assistant general manager.  

Both Tamara and Brett began working in the industry at a young age.  

“We lived out in the country in Aberdeen and my mom would pick us up from school and take us to the store and we would do our homework and just hang out until they were ready to go home,” Tamara said. 

The kids soon began working different jobs in the store. 

During Christmas they wrapped the gifts or stood behind the showcase taking out the items people wanted to see. Once they got older, they moved into goldsmithing. “It really seems like we have always been a part of it.”  

The siblings moved up in the company and are now heading up the second generation, mentoring the third, and discussing the possibility of a fourth generation. 

Jesse Riddle used to say he could not have done anything without his employees, customers, and family. The family-run company now has more than 700 employees, many who have been alongside the family for decades.  

At one point in the ‘80s and ‘90s, there were 23 family members working at Riddle’s Jewelry – a testament to the family’s cohesiveness. “We have been fortunate that the family members have always supported each other and make the effort to work together,” Tamara said.  “We want to make that effort to continue on.”

Tamara and Brett both said their father taught them to treat people well and everything else will fall into place. Both remember their father sneaking life lessons in during car rides when they were growing up. “Some of the things he told us when we were younger – he would say all this stuff and thinking back later he was just teaching us.”  

Tamara and Brett are now passing down their father’s wisdom to the next generation hoping that Riddle’s Jewelry’s legacy will continue for many more decades.  

Brett said their father believed he never worked a day in his life. He loved what he did and his family and did not see it as work.  

 How can you not love what you do when you are always celebrating love? 

“We are in the love business and get to help people with those special moments in their lives,” Brett said.

Who are the family members working with the family-run Riddle's company?

Currently seven family members work for the company:

• Brett Riddle, second generation, President/CEO
• Tamara Riddle-Schumacher, second generation, President of Manufacturing/Gemology
• Tim Riddle, second generation, Gemstone Purchasing Manager
• Scott Riddle, second generation, Manager of Watertown Riddle’s Jewelry/District Manager
• Loren Jensen, third generation, Director of Corporate Office
• Jesse Riddle, third generation, Regional Manager
• Dominic Schumacher, third generation, Mt. Rushmore/Landstrom’s outlet manager