2024 Trusted Advisers Legacy Adviser: Richard Ollis

From the looks of it, Richard Ollis’ path was charted for him. He’s a fourth-generation Springfieldian and insurance adviser. The family business, Ollis & Co., started on Commercial Street in 1885.

Just about 100 years after the firm was founded, Ollis joined its ranks after four years serving as a petty officer second class on the USS John F. Kennedy for the U.S. Navy.

He would rise to become the firm’s CEO, steering the insurance and business advisory team of what is now Ollis/Akers/Arney to oversee nearly $175 million in managed premiums and 67 employees.

But as much as Ollis’ career follows in the footsteps of generations before him, he’s blazed his own trail as an insurance, business and community adviser by embracing innovation, growth and service.

His approach to advising took a drastic turn about halfway into his 40-year career. Ollis says after the attacks on Sept. 11, 2001, the insurance market began tightening underwriting and raising prices. That shift meant uncertainty for clients – and he recalls one in particular that saw drastic increases at renewal, just a week before their policy was set to expire.

“They asked me to come back the day the policy expired and made me sit out in the lobby of the business,” Ollis recalls. “They came out with security and said, ‘We are exceptionally upset at how you have handled this. We’re going to ask you to leave.’ And security got me up out of my chair and escorted me out the door.”

A friend and local attorney called him the next day and said the company was considering filing a lawsuit against Ollis for not being proactive about addressing market conditions. That didn’t come to fruition, but Ollis says it was a wake-up call.

“I didn’t do anything illegal or maybe even morally wrong, but one thing’s for sure: I wasn’t out in front of this and communicating effectively on an ongoing basis. We were still handling this as a transaction,” he says. “That was the epiphany.”

He began training with insurance mentor Roger Sitkins in Florida. That led to developing the Ollis Edge 360, which focuses on strategic solutions to reduce risk and control costs both in the short and long term.

“That was when we started moving from a transactional business to a consulting business,” he says. “Now, we have quarterly meetings with our clients. We put together a plan, we go over market conditions.

“As I think back on my career, it’s really about learning and resilience.”

That theme of innovation and growth continued a few years later when, in 2008, Ollis transitioned the family firm to 100% employee owned.

“That initially started, to be candid, because we were running out of family members,” Ollis says with a laugh. “I was the only fourth generation of our family that had a real interest in the business.

“As we got into it, we realized that we could create a really unique and effective culture using employee ownership as the cornerstone.”

That turned into a winning model for Ollis, the team and the firm.

“As we started to look around and grow from a marketplace standpoint, we essentially were looking for other agencies that one wanted to cash out their equity to the (employee stock ownership plan),” he says. “That really resonated with the Akers & Arney organization, the Paul Long organization, and frankly, we’re looking at other opportunities.”

Ollis & Co. joined forces with the Akers & Arney team in 2015, and in 2018 acquired The Paul Long Agency. Ollis/Akers/Arney is now the second-largest independent insurance agency in the region, according to Springfield Business Journal list research. In addition to a suite of insurance products, the team also provides human resources and wellness consulting, claims management and contract review. In August, Ollis/Akers/Arney for the sixth year was named a Top Insurance Employer – one of only 43 companies in the U.S. and Missouri’s only company to achieve the distinction from Insurance Business America.

“I have become such a better leader the bigger and stronger my team is,” Ollis says. “It’s really a win-win situation. I just love the employee ownership model.”

In 2017, the longtime community volunteer turned to Springfield City Council and applied to fill newly elected Mayor Ken McClure’s seat. He was selected among six finalists and would serve the city for six years.

“I’ve always felt that serving the community is also an extension of what we do in our company,” he says. “We serve our employee owners. We certainly serve our client base. And in addition, we also serve our community. ... If the Ozarks is doing well, we are doing well.”

Ollis said his focus on quality of place was a highlight of his time on council, leading to the $26 million Grant Avenue Parkway project to create a multimodal route from Bass Pro Shops to downtown, as well as the daylighting of Jordan Valley Creek and the planning underway at Lake Springfield.

“If we can create a community where the economic and livability of our community is incredible, it creates opportunities for people,” he says. “I love that.”

His community service extends beyond council. He’s a founding board member of the Restore SGF homeownership initiative, and he’s served as past board chair for the Springfield Area Chamber of Commerce and on boards such as the Springfield-Branson National Airport, Commerce Bank and the Downtown Springfield Association.

Thinking back on what first led him to the family business, Ollis recalls selling advertising for The Standard at what is now Missouri State University.

“I loved interacting with other businesspeople and trying to help them promote their product or service through the newspaper,” he says. “My father, who’s always been an encourager and a staple in my life, started encouraging me that, ‘Hey, we’re also serving businesspeople and helping them and what we do is an exceptionally valuable service. You ought to give this a try.’”

His father, Ron, ended up being right.

“At our core, what we really do is we help other businesses, and we become a partner,” Ollis says. “I’ve loved it.”