In summer 2020, Kimsey Hollifield had a lot to celebrate. He and wife Lorna were nearing their 15th wedding anniversary. Their first daughter would soon be born. He’d completed goals of becoming a marathoner. And his decade-old business, Hollifield Financial Group, had not only been named one of the top five best in Charleston, it was also awarded the Thrive Award by WealthManagement.com as one of fastest-growing financial firms in the country. It was at this time that Hollifield knew he’d truly escaped the demons of the past.
The demon was already present when Hollifield reached his first conscious memory at age three.
Growing up in a single-wide trailer rented from a convict in Appalachia, the outside world called his demon poverty, but Hollifield knew it only as running. Every day in his early years, he watched his family trying to stall creditors and sharing their nightly dinner table with a mountain of bills they couldn’t pay. “Even as a kid, I understood the stress of money,” he said.
By age 11, Hollifield was juggling several odd jobs with being a middle school student — mowing a full round of lawns, selling homemade origami, cleaning industrial machines at a dry cleaner while wearing a hazmat mask and helping his dad on the railroad. Nothing he earned changed the situation, but inside his mind, the wheels were already turning. “I knew I had to make money to be able to control my destiny,” he explained.
RUNNING AND HOPING
Each week, one of Hollifield’s errands was to run his grandmother’s money from her alterations business to the bank. Every time he entered the bank, he was struck how this world of money and wealth existed.
“The deposits I made for my grandmother let me escape my reality for a moment,” he said, “and dream about being in this other world.”
One day, he took a step to eventually do more than dream. Noticing that the bank’s outdoor signs always carried the current interest rates, he began asking a teller questions.
“I think her name was Denise, and she would explain some of it to me,” Hollifield said. “I then realized I could watch the stock prices in the paper. So, every day after school, I would sit at the alterations shop and watch soap operas with my grandma and compare stock prices in the newspaper from the day before.”
RUNNING AND PRAYING
By 2005, at age 20, Hollifield was running as hard as ever. The clue from his teenage years had led him to pursuing a career in insurance, but he was still a long way from any real money. He had just married his childhood sweetheart, Lorna. Despite facing a dark future, they had determined that no matter what, they wanted to face it together.
After a $900 honeymoon which took every cent, Hollifield got a job selling insurance—and running a newspaper route overnight.
“Lorna would sometimes go with me,” he said. “And we had a small one-bedroom apartment that we could barely afford.”
They struggled for two years, always keeping their eyes on what they wanted.
“There was a massive mansion up this big hill near our apartment, and every day I would run the two miles up the hill to this house,” he said. “As long as I did that and made it back every day, I told myself we would be OK.”
But by age 22, Hollifield had nothing substantial to show for his efforts, and there was more darkness looming. He came home one day to find that their bank account was overdrawn. There was no running water. And Lorna had suffered a grand mal seizure, which causes loss of consciousness and violent muscle contractions.
Checking his pockets, Hollifield discovered $5—all the money he had in the world. He walked into a coat closet, closed the door and cried. Until that moment, he’d always trusted that his belief in himself would overcome the darkness he had been trying to escape. But now he was shaken.
“It was such a dark time for us,” he said. “And sitting there in the darkness of that closet, I wondered if the life I had always known was always going to be my life.”
When Lorna found him, they went to Subway, spent their last $5 on a sandwich for dinner— and then, more broke than they had ever been before, Lorna asked him to take a step on faith that could decide the future.
RUNNING TOWARD A LAST CHANCE
David Rainwater is the current market leader with Amerilife in the Dallas-Fort Worth metroplex. But on July 5, 2007 — Hollifield’s birthday — while working in the Asheville office, he got an unexpected call.
Rainwater listened patiently as Hollifield, whom he knew through a business associate, explained his circumstances and begged for a chance to work with Amerilife as an insurance agent.
“And I practically hired him on the spot,” said Rainwater, recalling the memory. “I couldn’t turn away someone who had had the courage at a really bad time to reach out.”
“I started working in David’s office on July 19, but I kept my paper route until November,” Hollifield said.
RUNNING FOR THE VISION
After Rainwater’s last-minute rescue, Hollifield not only became a valued salesman, he was offered the chance to run an Amerilife office in the Lowcountry, which he accepted. He was only 23, the youngest to receive the opportunity.
Money was flowing, but by 2010, he decided the time was right to strike out on his own—launching Hollifield Financial, now headquartered in Summerville and with satellites throughout the area.
“We take care of clients by managing IRAs, doing 401k rollovers and keeping the growth of assets safe so that they last throughout retirement,” Hollifield said. “And we also have a lot of fun together at events like our recent harbor cruise.”
Hollifield is now recognized by Financial Independence Group as being ‘the tip of the triangle’ — the top 1% of advisors nationwide.
“Every day, Lorna and I remember all we went through,” he said. “But now, we cling much more tightly to the blessings.”
By L. C. Leach III