January 25, 2021

’Well worth the time and investment’

After more than 40 years in the insurance industry, Phil Tyler is nostalgic of family, friends and community.

This year, Phil Tyler rang in the New Year with one resolution – to continue the “Tradition of Insurance Excellence” with and for the people whom he has worked beside, and served the needs of, for over 40 years.

On January 1, Tyler Insurance Services Inc. merged First MainStreet Insurance L.C. – an affiliate of True North Companies L.C. – which specializes in helping independent agencies in local Midwest communities with their perpetuation process.

While most people set a goal of retirement, Tyler is as enthusiastic about his career as the day he started.

“I don’t want to quit and I don’t have to quit,” said Tyler. “I can continue on with my love.”

Tyler and his staff in Creston and Mount Ayr have a collective 180 years of experience in the insurance industry. A merger With True North Companies meant, not only would they have more resources to navigate an ever evolving field that has come with more automation and government regulations over the years, but he was comforted in the fact that his staff, agents and clients – made up of long time friends and family – could continue Tyler Insurance Services long after he’s done.

For Tyler, it’s these people, including his wife Judy, he attributes his decades of success in business to.

A different path

Tyler, who grew up in Lenox, hadn’t always planned on a career in insurance. Upon his high school graduation from Lenox High School, he pursued a very different path his freshman year at the University of Iowa – he was “groomed” to become a medical doctor by his father. While he found the the coursework in biology, organic and inorganic chemistry interesting, he said it wasn’t something he was at all passionate about. Two years later, he told his father he wanted to carve a different path and enrolled in the school’s college of business. There, he felt inspired.

“In the college of business there was a professor that was considered the number one insurance guy in the country. His name was Dr. Emmett Vaughan. He was easily the best instructor of any kind that I’ve had at any level. A brilliant, brilliant man,” said Tyler.

Studying under Vaughan – who was instrumental in the establishment of the TIppie College’s Institute of Risk Management at the U of I – Tyler found his niche.

“Once I got into a couple of courses of insurance at Iowa, I found out I really loved it. It was something I could really get my teeth in to. It was very complex,” he said.

Following his 1964 graduation from Iowa, Tyler was hired as a federal bank examiner with the Federal Deposit Insurance Corporation, with which brought him border to border in Iowa helping banks stay compliant.

“Two years of that, on the road 100% of the time, I grew tired of that very quickly,” said Tyler.

Coming home to Southwest Iowa

In 1966, Tyler’s life was about to change. He was contacted by Northwestern Mutual. He was asked if he would consider a position in Creston. As one of the most respected life companies in the world, he obliged.

“I liked what they had to say, so I came down and took over for Peanuts Jones as a district agent,” said Tyler.

For just over two years, Tyler worked at NWM, but he eventually felt limited as the company only permitted the sale of its own products.

“I was seeing a lot of business going out of my door that I couldn’t write and it was depressing,” he said.

Northwestern Mutual eventually wanted to send Tyler back to Des Moines to become a district agent. He declined.

“We loved Creston. We just loved it – made a lot of friends and didn’t want to go back to the city,” he said.

Compelled to stay, he explored his options.

His uncle Bill Evans, who owned the men’s clothing store Evans Brothers the third oldest business in Creston at the time – sat Tyler down over a cup of coffee and asked him what he was going to do.

“My uncle proposed that I come work with him in the clothing store as he would be retiring,” said Tyler.

After mulling it over with his wife, she said, “Let’s give it a shot.” So he did and went to work with his uncle in 1968.

Family lessons in business

Tyler was no stranger to business operations as his family owned and operated Tyler Pharmacy in Lenox. Tyler Pharmacy was the oldest family-owned drug store in the state before it sold to NuCara in 2013 after 133 years.

Through the pharmacy operation that his grandfather Oscar Dewayne Tyler started, which eventually was operated by his father Oscar Donald “Don” Tyler, then his brother Eugene Winston “Win” Tyler, he learned the importance of human connection with his customers on a personal level.

At Evans Brothers clothing store with his uncle Bill Evans said he applied the principles and practices of going above and beyond for those who did business with him. With his uncle, he spent three years honing his skill for tailoring a product to suit his client’s needs.

“I loved clothes. We had the cat’s meow. We had the finest clothes you could buy, available right here in Creston, Iowa,” Tyler said.

Tyler said, at Evans Brothers, he and his uncle specialized in custom clothing from Louis Roth and Kuppenheimer, which was a “six make” – all handmade suits and coat jackets. Suits ran between $200 to $500 and top coats were approximately $1,000 at that time.

“They were the two best men’s clothing manufacturers in the United States,” said Tyler. “They would go to Europe and buy the confined goods. Nobody else could have them.”

To learn more about their customers’ tastes and preferences, the Evans and Tyler hosted trunk shows after hours, inviting their customers to meet directly with salesmen, who would bring swatches of the finest quality.

“I learned to sell working in that store. I learned to deal with people, which was something you didn’t do as a bank examiner,” he said.

When his uncle Bill was ready to retire in the early 1970s, Tyler bought him out.


After 12 years of owning the clothing store, Tyler began to witness the start of discount clothing operations, which started selling the once private labels he sold. To compete, Tyler doubled the store’s volume, but saw his profit margin fall. He started to consider his options again.

“Approaching 40 years old, I felt I needed to consider a career to land in,” he said.

In 1983, Tyler had a fateful conversation with fellow business man, Ray Scurlock, who owned his own insurance agency in Creston. Tyler was reminded of how passionate he once was about the work. Scurlock, who had separated from his business partner three or four years prior, asked Tyler if he would be interested in joining him at the agency.

Tyler said his wife Judy encouraged him to go.

“‘I think you need to be in the insurance business. I know what you love. It’s your passion,’” Tyler recalled her saying. “So I went to Ray and said, ‘Let’s do this.’”

Tyler Insurance

On Feb 1, 1983, Tyler sold his clothing store business. He ran an ad in the Des Moines Register and it sold in 24 hours.

“It was amazing,” he said.

The rest, he said, “was history” and joined Scurlock’s agency.

While working with Scurlock at Scurlock Tyler Insurance, Tyler experienced more growth in his field as he earned a Certified Insurance Counselor designation in 1985. He was then awarded the distinction of Certified Professional Insurance Agent, (CPIA) in 1987.

After Scurlock retired from Scurlock Tyler Insurance in 1993, Tyler renamed the business in 1998 and became its sole owner.

When Tyler first began business in Creston, there were 13 other agencies in the Uptown. Today, while other insurance agencies remain, he is still proud of Tyler Insurance Services for its longevity in Creston’s Uptown business district, its expansion to Mount Ayr, and working alongside his daughter, Devon Tyler-Leith, a certified insurance counselor, who joined the agency in 1999 before becoming the agency’s president in 2016.

Tyler’s involvement in the community has also branched beyond the doors of his business, which has helped him develop stronger bonds within the communities he serves. He has served 35 years on the Union County Development Association board, 14 years on the Greater Regional Medical Center Foundation Board, with 11 as its president, the University of Iowa’s Presidents council, the National I Club Board, and 30 years as the president of the SW Iowa I Club. He has also been a Methodist church trustee, an Elk for 54 years, president of Crestmoor Golf Club twice and a long-time member of the Police and Fireman’s Pension Trust Board.

“Everything I did throughout my life, I learned something that I was able to bring to the world of insurance. So it was all well worth the investment of time and effort,” Tyler said. “I dearly love what I do and have not intention of quitting. The God Lord will retire me when its time.”


Sarah Scull is a San Diego transplant now living in Creston, Iowa. Sarah joined the Creston News Advertiser editorial staff as a reporter in in 2012 and was promoted to editor in November 2018.