Like a lot of boys, Sean McLaughlin started a lawn-mowing business when he was a teenager. Unlike a lot of boys, he acquired for his business a pickup truck, heavy-duty landscaping equipment, and more than 100 accounts, and he ended up employing all of his younger brothers.

He was just getting started. Nowadays, at 56, he runs three companies, having earlier sold a financial software start-up for tens of millions of dollars.

McLaughlin could have eased into a cushy retirement.  But that’s not how he rolls.

“I’m like a husky, and I have to go run around,” McLaughlin said of his need to start and develop businesses.

“It’s that kind of impulse,” he told the Register. “I don’t know where it came from. I don’t know why I have it.”

But why is he so good at what he does?

McLaughlin hesitates before he answers, not certain how to explain it, except that creating a business comes naturally to him and he likes it. “I love problem solving. I think it’s fun. At the bottom of it all, it’s like a puzzle. It’s like a sport to me,” McLaughlin said.

Chris Devine, the president and chief executive officer of one of McLaughlin’s companies, says McLaughlin shares some of the key qualities he’s observed in other successful entrepreneurs he’s worked with over the course of his career: He’s intense, driven, creative and “insanely smart.” However, he adds, “none of them are like him.”

“He has 10 children and is very engaged. His family life is very, very solid. And that’s what I respect about him. He’s a very serious family person, and a very serious moral person, and I have not seen that in other people with great success,” Devine told the Register. “To me, that’s why I’m here 12 years later. That’s a guy you want to be like.”

Getting Started

The son of a dentist, McLaughlin was born in Boston and grew up in a town west of the city, the oldest of 10 kids in an Irish and Italian churchgoing Catholic family. He majored in computer science at Harvard College, and after graduating, he got a job with a hedge fund in Boston on the recommendation of one of his lawn-mowing customers.

But he was restless as a cog in someone else’s machine. A software project at work led to an idea: This could be a company. He left his job and threw himself into what would become Eze Castle Software, which automated securities trading for hedge funds, eventually capturing the market and spinning off another successful financial services company. He named the company after the town in the French Riviera where he and his wife Laura honeymooned in the early 1990s.

McLaughlin prefers creating businesses to managing them. Once Eze Castle became hugely successful, he felt restless to do something different.

He decided to leave the company and move to Alaska, drawn by its wilderness, beauty and adventure. But he also had an interest in public policy, which led him to a yearlong fellowship in the George W. Bush White House. Someone he met through the program recruited him to become chief operating officer of the American Red Cross.

By the end of 2006, McLaughlin followed through on Alaska, settling his family into a home atop a 2,250-foot-high mountain in Anchorage, the highest point in the city.

At first, he stayed home and tried to introduce efficiencies into everyday life that Laura didn’t want. She told him he had to get out of the house. That led him to buy an existing business that provided parts and services for bush airplanes for fly-happy Alaskans. At the time, it had two employees and $100,000 in annual sales revenue. The business, now called Alaska Gear Co., now sells airplane parts, clothing and other products all over the world. It has 100 employees and does $20 million in annual sales revenue, McLaughlin told the Register.

In 2013, he bought Craig Taylor Equipment, which has the John Deere, Bobcat, Peterbilt and Develon dealerships in Alaska. (It had 35 employees and $28 million a year in sales when he took it over; 132 employees and a projected $110 million in annual sales in 2025.)

 He didn’t like the financial software the company had, and he didn’t like the off-the-shelf solutions available on the market. So he founded Flyntlok, a financial software company that now has 28 employees and does a little more than $3 million in annual sales.

McLaughlin’s kids range in age from 14 to 30. Some of the adults live elsewhere in the country. All of them have gone to Catholic schools, including several at the school where Laura taught elementary grades until recently. They also have three small grandchildren.

Friend’s Admiration

When McLaughlin moved to Alaska, he had one friend there, Scott Merriner, whom he met in college, who is now pastor of ChangePoint, a nondenominational evangelical church in Anchorage that draws about 2,000 people every Sunday.

Merriner told the Register he admires McLaughlin’s commitment to his Catholic faith “despite things that could pull against that,” including the absence of extended family and the various demands on his time.

“He’s not a Catholic entrepreneur in just some sort of cultural Catholicism,” Merriner said. “He has maintained the rhythm and faith of a devout Catholic.”

That means he goes to church regularly, of course. But Merriner also marvels at the many times McLaughlin has given a second chance — a job at one of his companies, for instance, or a task helping his family — to unpromising candidates with sketchy backgrounds.

“Sean has an enormous soft spot for young men who are stalled out,” Merriner said. “And they’re a mess. But he sees potential. And most of the time, it doesn’t pan out the way he’s hoping. Most of the time he has to let them go. But not all of them.”

The Register asked McLaughlin why he does that.

“I usually make some connection with the guy’s story. I see something redemptive, or something he should find redemptive,” McLaughlin said.

Asked about his spiritual life, McLaughlin mentioned a weekly habit he started at the recommendation of a priest friend — something he calls a “mental breviary,” a sort of examination of conscience in which he thinks about all the people in his life, starting with his wife and kids, and considers whether he is doing enough for them. 

He goes through the checklist during one of his daily runs — 4 miles at 8 minutes a mile — which help prepare him for his yearly marathon and other races. His run begins about an hour after he gets up at 4:30 a.m.

McLaughlin’s businesses aren’t religious, but they provide an opportunity for what he calls “a quiet witness” through the way he treats the people who work for him while still trying to serve the company’s goals.

“If you’re gonna run a business,” he said, “it’s all about empathy and excellence. And the reason you need both … is empathy by itself will basically guarantee your business goes bankrupt. And excellence without empathy is dictatorship — you have your best people leave because you’re just always driving sort of for the highest ultimate output.” 

The thrill of making money diminished for McLaughlin a long time ago. “At some point, the money becomes meaningless,” he said.

Some successful entrepreneurs respond to that realization by giving a lot of money to charities, he noted. But McLaughlin also sees his role as helping people provide for themselves and for others.

“In some ways, it’s a lonely thing being a CEO and running a business because you don’t get to see and measure all the benefits you do create. And if you think about all your employees and what’s happening in their lives and what you’re helping them do, and when they have their second and third kid or when they buy their first home, you’re part of a big system,” he said. “I’ve got about 300 employees up here in Alaska. Weddings are happening, births are happening, first homes are happening, grandparents are moving in with kids.”

He said, “To me, that’s a pretty weighty thing that I find a lot of value in.”