CEO Connect: Lisa Holland talks leaving her comfort zone, mentoring women in aviation and more

Lisa Holland was appointed as chief executive officer of the nation’s largest privately owned aviation services and real estate network 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 has 16 fixed-base operations and a real estate portfolio of over 4.2 million square feet of terminals, hangars and offices. She oversees a team of 475 people that produced a revenue stream of more than a quarter-billion dollars in 2022.

Bridgette Bello, publisher and CEO of Tampa Bay Business and Wealth magazine, interviewed Holland in front of a sold-out, live audience at Sheltair in Tampa. This interview has been edited for length and brevity. View photos from there event here.

What has it been like being Mrs. March TBBW 2023?

Very unnerving. It’s not often that you get to see yourself on a magazine cover and then, not only that, but every email for 31 days in March. I’m very humbled by this story and everyone that knows me, that read this story, has said that you all did a fabulous job of capturing me as who I am, and I couldn’t agree with that more.

I’m also in a very male-dominated industry, much more so in my previous life than now, magazines do have more women. How did you gain your footing and your confidence? What advice would you give to somebody else who’s in a male-dominated industry? 

I was appointed president, literally, six weeks before COVID came. And I just remember sitting in a conference room with my vice president of human resources going, ‘Oh my God. Now what?’ I’m fortunate to be surrounded by a great leadership team who has strength that I certainly did not have at that time. 

The silver lining of COVID, for me, though, was I didn’t really have a choice. I had to step up and at least fake confidence because I had a team of 500 people wondering what was going to happen. 

As a woman, I think you lead with your heart and empathy. We had our first-ever companywide Zoom call, because I felt like it was important that I explained to the team what was going to happen, that we weren’t going to lay people off and we were going to do salary reductions and hour cuts. 

I didn’t know what was going to happen. I couldn’t give answers. But I did promise them that I would communicate and be transparent.

Now, in 2023, I feel very fortunate that I’ve met a lot of amazing businesswomen in Tampa, a lot of them who are here. And not only to call them my friends, but they’re my mentors. They’re the ones that are cheering me on and who really understand what it is like to be in this position because, like they say, it is lonely at the top. 

Something exciting happened under your leadership since our interview. Sheltair is continuing to grow, much like TBBW. Tell me what happened since did the story.

We just recently in December closed on our first [fixed-based operator] in Denton, Texas, and we just got the opportunity to buy out our competitor in Denton, Texas and in Melbourne, Florida. So that’s very exciting. And then, Saturday night at midnight, we will be 16 FBO strong as we will be taking over the FBO at Gwinnett County Airport, at Briscoe Field, about 45 minutes outside of Atlanta. 

A lot of family businesses struggle to make it to the third generation. I met your son, here tonight and you guys are going strong with the third generation. There are a lot of other business owners in the room who started their businesses and who could benefit from hearing how you got to the third generation. What can they learn from your experience? 

I feel fortunate that I was able to step in and kind of take over from my father. He’s 88 years old, soon to be, and is slowing down a little bit. I kind of stepped in and took over the helm. Then my son graduated from the University of Tampa, in May of 2020. It was his decision. I never wanted to force him into anything. Actually, years prior to graduating from college, he wanted to be a television production major. But then he did a couple of summers at our Fort Lauderdale FBO and I think he started to see the big picture, like, wow, this is a really cool industry. I can follow in my grandfather’s footsteps. So, when he enrolled at UT, he became a business major. And here we are today.

Fitness and wellness are a theme that we seem to hear from our women on the covers. How do you find the time, and why is it so important to you from a business perspective?

It’s not that I love to jump out of bed in the morning, but if I don’t make the time in the morning, it doesn’t happen. It’s kind of my non-negotiable and it sets the intention for the day. For me, working out is a huge priority. I like to run. I just did the Gasparilla half-marathon. I’ve done three marathons and two international triathlons. I just enjoy it. Especially when I’m with my girlfriends. When you do a two-hour training run, you can get a lot of conversation in. And then I don’t feel as guilty about having my nightly wine.

What are you doing to help other girls, and other women, find their way in the aviation industry?

Sheltair has always been a member of Women in Aviation. Every year we do an internal Women in Aviation Day that we host and we just kind of came up with this phrase this year, The Sisterhood of Sheltair. I think that really encompasses what us women are. 

I was just reading a report, today, and we have 79% males in our company and 21% females. It’s really important that we embrace each other and lift each other up. We are soon to have our third female general manager. 

Then piggybacking off Women in Aviation, they host Girls in Aviation Day every year. Two years ago, we hosted the first Girls in Aviation Day in Tampa. It was an amazing event, especially considering we were on the tail end of COVID. 

Last year, I challenged our team. We had 75% of our bases hold the Girls in Aviation Day. Tampa had about 700 participants. The Coast Guard came out and did a demonstration, the helicopter from Tampa General Hospital, and we had astronaut Nicole Stott. We’ll be hosting that again on Sept. 23. We’ve also partnered with several organizations, I Hart Flying Foundation to give scholarships to women that want to learn how to fly. Last year we presented five ladies with scholarships at Girls in Aviation Day to continue their flight pursuits whether it be in avionics or piloting, so we really like to give back.

Anything else you want to share before we close this out and let people come swarm on talk to you?

It’s been a ride this March, one I won’t forget, that’s for sure. Thank you. It’s been great to meet you and I look forward to an amazing friendship with you.

Add me to that list of people you call and say, ‘Do you want to get a glass of wine?’ I’ll go with you.

Will do. ♦


TBBW’s “CEO Connect” series is an exclusive, invitation-only, event that brings together the Tampa Bay area’s top business leaders to meet and mingle. Nperspective, Southstate and Windsor Capital were presenting sponsors. The host sponsor was Zoo Tampa at Lowry Park.

TBBW’s video partner is Empowering Creative.

The evening begins with a cocktail reception for about 120 guests, followed by an interview with that month’s cover CEO.

Partnering with TBBW on future editions provides an opportunity to network with the area’s business elite, generate new business opportunities and increase brand awareness.

For information about event sponsorship opportunities, email Jason Baker at

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