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Since his childhood, Landry has never shied away from hard work. From his college years and into adulthood, he’s always taken on more than most people would even think about being able to handle. He’s succeeded, and has no plans to slow down anytime soon.

Owning two high-performing businesses might sound like a lot, but for Landry neither the high level of performance or the multi-tasking is nothing new. As a student, he earned a scholarship to Westbrook College — now the University of New England — as a member of the school’s first men’s basketball team. However, Landry wanted the experience of a larger school, so he transferred to the University of Southern Maine after his freshman year.

While a student at USM, he took a job working second shift at Barber Foods. The job wasn’t much fun – it was cold, it was hard work and by most standards the pay wasn’t great. But Landry was a college student in need of money, and having grown up a hard worker, he lasted longer than the average second-shift employee. In fact, he lasted much longer – 11 years.

Landry didn’t spend all of that time working the line. Having proven his work ethic and business acumen, he was steadily promoted up the ladder — even while still in school. His journey at Barber culminated with five years as the company’s director of food service marketing. Reporting directly to the founders’ son-in-law, Landry oversaw a sales force while strategizing and targeting food service companies like Sysco to sell Barber products.

“It was an absolutely fabulous job,” says Landry.

But true to character, Landry couldn’t stick to just one job — even when he was still in school and moving up the ladder at Barber. At 19, he bought his first rental property and converted it from a two-family to a one-family — and he did the renovations himself.

“Most of my friends were in the Old Port, and I was in a basement scraping paint. Not only did I enjoy it, but I knew it was one path to getting ahead,” says Landry.

With the money earned from this property, he made new investments. He kept this up even when holding down an executive-level job at Barber.

“I was burning the candle at both ends,” he says. But it has paid off.

With 11 years at Barber, but limited paths for advancement in the company, Landry began to consider what his options were. His real estate investments were going well, and it was clear he had a knack for the industry. With his wife’s encouragement, Landry earned his real estate license.

As his real estate business grew, he knew that he’d have to make the leap completely away from Barber at some point.

”One of the scariest things I had to do was leave the security of that job. Leaving a good job was just something you didn’t do. It was one of the hardest decisions I had to make,” reflects Landry.

And, he adds, when you make a leap that, “Failure is not an option. You just have to do it.”

While Benchmark initially grew steadily, the timing of Landry’s business launch wasn’t ideal. He had partnered with a realtor friend from college, and they had launched Benchmark just before the crash of 2008.

Landry was 34 years old, and his business was doing well pre-crash. He put the marketing and business skills he learned at Barber into use, and Benchmark had garnered a significant market share. But Landry, like the rest of the industry, wasn’t immune to the effects of the crash.

“When the phone doesn’t ring for two to three weeks, it’s a very sobering thing,” says Landry.

At the time of the crash, he had three employees to support in addition to himself. He knew that he could turn to the equity line on his house if needed, but before he did that, Landry tried a tactic others in the industry were shying away from — increasing marketing.

As Landry describes it, he doubled down the company’s marketing efforts and threw himself into guerrilla style strategies. Using his own supplies, Landry printed off sales materials and brought the pamphlets and flyers door-to-door himself. Doing so saved him money on a mail house while allowing him to keep getting the Benchmark brand out there.

The effort helped keep the business afloat, but it was still slow going to get where Landry wanted to be. The bottom didn’t hit until 2010, and it took four years before he started to see values back up where they were pre-crash.

Since then, though, Benchmark has experienced incredible growth. Riding his efforts to keep the company afloat into the post-crash boom, Landry has become Portland’s top listing/selling realtor.

While accomplishing this, Landry has also been growing CornerStone Building and Restoration, establishing himself as a leader in home restoration. It’s a natural next step in Landry’s career considering that he purchased and restored his first property before the age of 20.

The company’s first project was a major rehab of 104 West Street in Portland. Landry was heavily involved in that project, but over time he has stepped away from direct involvement with the day-to-day at CornerStone and has handed the reins to his general manager.

As for the future? For both companies, Landry sees plenty of opportunity, particularly in Portland, and not much reason to venture further outside of the area.

”We are in a renaissance in every way in Portland,” he says.

And Landry is helping Portland through more than just real estate and restoration work. He is also intent on giving back.

Each year, he and his companies host For A Cause, an event where local non-profits chosen by the community are given the opportunity to come share their mission and build awareness with the local business community. The event has grown each year, and it’s been a great success for the non-profits involved. Each summer, Landry and his companies also host the Portland Kids Duathlon to benefit the Foundation for Portland Public Schools. Beyond that, Landry is also committed to giving 10% of the companies’ profits back to the community each year.

As Portland has grown in recent years, Landry has been at the center of the boom. He is driven by a relentless work ethic — one that was instilled upon him at a young age — yet he still finds time to support the community that has helped his business grow.

That’s why Tom Landry is a Maine Icon.

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All photos by Peter Anania