Unintentional Entrepreneur Helps Local Business Owners Succeed

Unintentional Entrepreneur Helps Local Business Owners Succeed

Since Linda Nottingham retired to the First Coast 25 years ago, she has made it her mission to help area businesses succeed after selling two companies she co-founded in Chicago: an independent insurance brokerage and a managed care company.

As a volunteer for the business mentoring organization SCORE Jacksonville, and through her own coaching practice, the Texas native has helped hundreds of Northeast Florida businesses launch, grow and thrive.

“It has made a transformative difference, especially in our North Florida community,” says Jackie Perrault, director of the Association of Women’s Business Centers.

Perrault benefited from Nottingham’s mentorship when seeking career advice. “She is one of the most transparent and open mentors I have ever had.”

Business coaching

Nottingham is also president of CEO Focus, a business coaching practice.

She facilitates peer mentoring roundtables, providing business owners, from startups to multi-million dollar companies, with a confidential environment to help them solve their toughest business challenges.

In their roundtables, each member asks a question about the challenge, helping the business owner solve the problem through a facilitated group discussion.

Participants learn from the mistakes and successes of others. Nottingham only gives advice when asked. It also offers personalized tutoring.

An involuntary entrepreneur

How did a former social worker and educator become a business advisor?

Nottingham’s path to entrepreneurship was unplanned. She started as a social worker in the Riverside, California, welfare office and reinvented herself in Chicago as a 37-year-old divorced mother of two when she couldn’t make ends meet as an educator.

Before that, she taught Native American children in Arizona and was a public school counselor, earning two master’s degrees in education along the way.

Then, in 1983, with no prior business experience, she tried to persuade a Chicago acquaintance to hire her as a consultant to get a hospital laundry up and running that was being moved off-site.

“He told me he couldn’t do it,” Nottingham recalls. He was told he was “not employable.” Coming from an education background, Nottingham responded with an operational plan and said, “You don’t have anyone else to do it, so why don’t you hire me?”

He did. That led to more contract work and eventual full-time jobs as a marketing director for a preferred provider organization (PPO) and an executive for a health maintenance organization (HMO).

When the HMO’s new owner laid off all the employees, she was worried that she wouldn’t be able to find a similar position quickly, so she and a colleague decided to go it alone.

They launched an independent health insurance brokerage from their basement in Nottingham.

“It was an act of desperation. “We were scared to death,” says Nottingham. “My security depended on a job. “It was scary starting a business and not having a job because you had no income at the beginning.”

Nottingham, who relied on unemployment until the business grew, made calls from a rotary phone in his home until he could afford a business office. “It wasn’t really an option. We had to do it,” he says. And they did.

Nottingham says not lying about pre-existing conditions on health insurance applications helped his company stand out and grow. “Honesty was still a highly valued commodity, because there was so little of it,” he says.

That translated into success in insurance underwriting. Building on that success, he later co-founded an independent company: a managed care company that helped physician groups contract with insurance companies at a time when managed care was taking off.

Linda Nottingham with her daughter, Courtney Rivas, the new owner of the insurance brokerage, in 1998. | Provided by Linda Nottingham

When the company was sold in 1996, it was the largest privately held company of its kind in Chicago, with 100 employees, Nottingham said.

Despite owning a business in the 1980s, she faced little resistance, aside from letters addressed “Dear Gentlemen” and a bank requiring her business partner’s husband to co-sign a corporate car lease because married women were not allowed to go into debt at the time.

Facilitate orientation

“I don’t think I would be where I am today if I hadn’t had the opportunity to have her as a part of my life,” says Harold Boyett, president and CEO of Blue Streak Couriers, who participated in a peer-to-peer mentoring roundtable for companies with annual revenues between $1 million and $50 million.

“What made Linda so good at this is that she had the life experience to back it up. When you have someone who has been there, done that and is helping to facilitate something, you have the utmost respect for them,” Boyett says.

He appreciated the high level of intimacy and confidential space created by Nottingham, where participants felt comfortable delving into their biggest business challenges.

Teach through history

“Linda made me a better business woman,” says Patti Peeples, founder of

Participating in a roundtable discussion offered through the Jacksonville Women’s Business Center nearly 20 years ago, Peeples credits Nottingham with helping her grow and sell her business.

He benefited from Nottingham’s storytelling approach to teaching. “It’s a powerful technique and his years of experience meant he had stories… for almost every situation,” says Peeples. “She doesn’t tell you what to do. “She will tell you a story about another company that didn’t do it and some of the consequences.”

One story stuck in Peeples’ brain: a local business that went bankrupt after the IRS hit it with a hefty tax bill for keeping poor records.

After an audit, the IRS disallowed some of the company’s business expenses because they were not documented in its annual corporate minutes and resolutions. As a result, the company owed significant taxes that it could not pay.

“You can imagine how one might respond differently if they were simply told… ‘Fill out these boring forms’ versus ‘If you don’t, here’s what could happen,'” Peeples says.

“I have good horror stories,” says Nottingham. “What I like most about horror stories are the places where I made mistakes.”

When Peeples wanted to sell her company, Nottingham guided her through the high-stakes process with insights from her own experience.

He connected Peeples with experts in Northeast Florida who helped grow and find the right buyer.

One such expert was the former CFO of Exxon Mobil, a SCORE Jacksonville volunteer, who met with Peeples for two years to expand his product line. “It improved my profitability. That made a significant difference in the acquisition price,” Peeples says.

Other victories

Linda Nottingham | Provided

Nottingham not only helps established businesses, but also new ones. As a SCORE Jacksonville volunteer, she mentors aspiring entrepreneurs.

He recalls meeting a couple who wanted to open a gym. After reviewing their business plan, they realized it wouldn’t be profitable for another three years. So, they abandoned the idea.

“I consider it a success because they didn’t spend their money… or take out loans and then find out later that they weren’t going to produce the results in the time frame they wanted,” Nottingham says.

Now in her 28th year of “retirement,” the avid golfer who rounds 18 holes every Sunday and models part-time has no plans to slow down.

In the 1980s, at a time when business resources (especially for women) were limited, she didn’t have the advantage of a mentor. “That’s why I feel compelled to do it,” says Nottingham. “I like helping people. I’m happy to share my own mistakes.”