Lisa Holland is piloting Sheltair through the highs and lows

Lisa Holland is intentional in how she describes her role at Sheltair, as chief executive officer and president, yes. But it’s still her parents’ business, not hers. 

“It’s very much a family business. I work for a salary, just like everyone else there,” she says.

This is the way Holland speaks about many things. Frank, direct, but with a lot of heart, and always humble. She doesn’t see herself as a big deal. Just a lady with a job to do. 

And a job she has done well. 

She was appointed as CEO a few weeks before COVID-19 shut down the world and while dealing with the unknowns of a global pandemic that, essentially, grounded air travel until the world adapted. Meanwhile, she was finding her foothold as a woman leader in a still very male-dominated industry.  

She doesn’t pretend it was easy, or without hiccups, either. 

But as a living testament of her positive energy, and vision, Holland is running the nation’s largest, privately-owned aviation services and real estate network, operating 15 fixed-based operations and a real estate portfolio of over 4.2 million square feet of terminals, hangars and offices. Today, she oversees a team of 475 people that produced a revenue stream of more than a quarter-billion dollars in 2022.

She might not think she’s a big deal, but numbers don’t lie. 

***

“I’m not the kind of person to just sit around,” Holland says. “My personal motto, that everyone knows, is get stuff done [#GSD].”

From a young age, she helped her dad at his construction business, Holland Builders. 

“After school, I would go and make photocopies and put envelopes in the stamp machine or empty garbage cans,” she says. Adding, she just liked staying busy and, yes, earning a few bucks of her own didn’t hurt. 

She first ended up in Tampa when she attended the University of South Florida. 

She then fell in love, got married and had a son. She enjoyed the home life of being a mother and wife but, as often happens, once the child was in school, Mom didn’t want to “sit around” anymore.

In 2005, when her son was about 10 years old, she purchased a Stroller Strides franchise, which is a fitness class for mothers and their babies. 

“It was totally outside of my comfort zone but proved to be a precursor to my entrepreneurship journey,” Holland says. 

She did that for seven years and then sold that franchise to one of her clients, in 2013. She went on to establish her next venture that same year, this time working with nonprofit organizations and their events. 

Named Team Holland, her company worked as a community liaison for nonprofit groups needing help in the charitable event space. 

“Running Team Holland kept me so busy that Sheltair was never on my professional radar at that time,” she says. “But once I got back involved there were things I saw and was like, wow, I know I have great ideas to help improve the operations and overall business … it went from zero to 100 in a year.”

Originally, she planned to only work about 20 hours a week, but she knew she had to be visible to develop new relationships and earn credibility at the business.

It wasn’t a direct flight getting there. 

***

Sheltair was established by Holland’s father, Jerry Holland, in 1963, in Fort Lauderdale, where the company’s headquarters remains today and where Holland was born. 

“My family life was pretty much suburbia. My father worked all the time. My mother stayed home and was a mom catering to my sister and I,” Holland says. 

Before Sheltair, there was Holland Builders, a business run out of the Holland home. 

“When dad started Holland Builders, 60 years ago … his focus, at that time, was mainly residential building and community projects. Then he evolved into the commercial real estate market.” Holland recalls. “Everyone in my dad’s circle knew he was a trailblazer. Someone approached him one day and said, ‘Hey, I’ve got these hangars. Is it something you’d be interested in?’ ” 

Those hangars were located at the Fort Lauderdale Executive Airport. After Fort Lauderdale came Daytona and then Orlando. 

As the company grew, Jerry Holland’s daughter was busy building her life and her own businesses. But the family was ready for dad to slow down a little and take a step back. The vision was that Holland would step in to continue the family legacy.

“There was no onboarding or job description, just a vague directive to ‘be more visible,’ ” Holland says. “So, I made a plan to visit every base, meet with every general manager and, I remember, the first one on my list was Tampa.”

She explains that day as the feeling one gets their first day of school. Not everyone in the company knew who she was. People knew Jerry had two daughters, but most had never met Holland. 

“At first, obviously, people were unsure what to think when they got an email from me saying, ‘Hi, I would love to spend a day with you.’ But then everyone saw how serious I was about getting to know not just the business, but the people,” Holland says.  

It took Holland a good six to eight months to get acquainted and embraced by her team, she says. 

Six weeks after she was named president of Sheltair, the world went into lockdown mode because of COVID. Planes were grounded. Travel was banned. For a relatively new aviation leader, it was basically the worst flight plan one could imagine as there were so many unknown challenges to face.  

“We had 513 employees, so we didn’t qualify for PPP assistance, at first, and I was not going to draw names out of a hat,” Holland recalls. She adds they, eventually, were able to get assistance. “We took a two-week pause. We did have to cut hours, and salaries, for 13 weeks, but I’m really proud to say that we did not lay off anyone. We eliminated eight positions, but we didn’t lay off anyone. And 13 weeks later, we returned hours and salaries.” 

While Holland and her management teams kept the business alive, and their employees employed, there was still a conundrum. An aviation business with no one flying anywhere, that’s a problem. 

“Nobody was flying. All of our employees were worried,” Holland says. “And then the governor of Florida opened our state back up, which meant the beaches opened back up. Short-term rentals were allowed to happen. Everything, literally, skyrocketed.”

It shouldn’t be a surprise that while everyone was working remotely, anywhere they wanted and they could come to Florida, they did. 

“It was so busy, at the time, at our West Hampton and Panama City Beach locations. Those two bases had planes flying in and out every second,” Holland says. “It also really helped that our company is diversified. On the aviation real estate side, we have 4.5 million square feet of leased hangar space, making it very advantageous for those areas where flying had not yet picked up.”

What seemed was going to be a huge storm for Sheltair, at the time, Holland and her team saw through the clouds to the calm. And the business grew. 

***

Sheltair’s future appears to be on a path of remaining in the family. Holland’s son Kai Seymour, property manager, is with the company. Holland keeps navigating the challenge of running a multi-million-dollar business, sometimes through foggy territory, never losing her sense of self while splitting her time in two “home” towns. One as the CEO at Sheltair, residing in downtown Tampa when she’s in the Bay area and one back in Stuart, where she has lived for the last 30 years.

“Businesses that make it through the first, second and third generations are few and far between, let alone past that,” Holland says. “We are in our third generation, my son, who graduated from the University of Tampa in 2020, is in the business and my hope is that he’ll be my successor someday.” 

In her downtime, she enjoys running and staying active. 

“Exercise and wellness are extremely important to me,” Holland says. “I have run three marathons, completed two international distance triathlons and countless half marathons. Exercise and running are my clarity and give me time to think or catch up with friends. When you are doing a long training run for two hours, it gives you plenty of time to brainstorm.”

It’s not been press, big exposure or other public relations moves that has gotten Sheltair to where it is today. 

“My father has only ever granted one magazine an interview. He’s just not a person to ever feel the need to put himself out there. And it’s not something I like to do either,” Holland says. “But I recognize that, these days, it’s necessary. It’s a different world now.” 

It may be a different world than 60 years ago, but the tenacity of the Holland line of Sheltair leaders seem to be well-suited to pilot it for, at least, another 60 more.

[image_slider_no_space on_click=”prettyphoto” height=”300″ images=”23841,23840,23842,23843″]

You May Also Like

David Habib’s Yo Mama’s Foods’ special ingredient is all in its name 

David Habib is what most would call an “old soul.” Ambitious from an early age, he’s also a little shy.  He’s a bit of a contradiction, he admits. Both forward-seeking

Five most-read TBBW cover stories of 2023

Here are the five most-read Tampa Bay Business and Wealth cover stories in 2023. 2. Jim Norman’s winding road of success 3. How Rick Brandt took his small-town, family business,

Cover Update: Michael Lundy

In October 2019, when Michael Lundy graced the cover of Tampa Bay Business and Wealth, he shared big plans for OLDER LUNDY, including expanding into Pinellas County.  As founder and

Elaine Myrback is living and leading with a zest for life

To underestimate her would be a big mistake. Big, huge, mistake.  Elaine Myrback doesn’t mince words. She’s not interested in following the status quo and she has no time for

Other Posts

How Cliff Scott found a second chance in business and in life

The story starts with a man. He was homeless but not entirely hopeless, not yet, though he tried to be, on more than one occasion. But God had a plan.

Jim Norman’s winding road of success

He could be called a boomerang surgeon.  Physician Jim Norman was a surgeon, quit practicing to pursue the dot-com boom of the 1990s and, later, returned to surgery. One might

How Trevor Burgess keeps winning, even when the waters may seem rough 

He’s known as the “first” in a lot of publications and while he feels pride to hold such a label, he doesn’t let it define him or his business achievements

How Steve Frey created the ‘Airbnb for Business’ and his plans to bring the offering directly to consumers

Steve Frey has had a ‘meh’ opinion of the corporate world from an early age. He watched his father, after many years with an employer, experience a layoff and it