Meet David: From Fighter Jets To Florida Homes

A new teammate with a fighter pilot’s focus can change how you see real estate. We’re thrilled to introduce David Paolillo, a former Air Force pilot and current commercial aviator, whose years of military moves, overseas living, and DIY remodels shaped a practical playbook for buying smart, selling confidently, and turning “ugly duckling” houses into equity. His story starts with constant relocation and ends with choosing Florida on his own terms—no orders, just intention—and the mindset that makes those decisions stick.

We explore what most listings won’t show you: bones, neighborhoods, and budget-friendly upgrades that compound over time. David walks through the Phoenix property he almost skipped, how the right agent reframed its potential, and the step-by-step approach that doubled equity in four years. For Tampa Bay buyers and sellers, the takeaways are clear: prioritize structure and location, invest in high-impact updates, and use market context to make time work for you.

We also push back on persistent myths around VA loans. Far from slow or risky, VA buyers are often the most organized and motivated clients in the market. With accurate expectations and a lender who knows the process, VA financing can move fast and clean—great news for sellers chasing certainty. Add modern tools like high-definition video tours and live neighborhood walkthroughs, and long-distance or overseas purchases become not only possible but efficient.

Mindset is the throughline. From the cockpit to the closing table, staying ahead of the deal matters: prepare early, solve the closest problem first, and keep your cool when stakes run high. We share negotiation tips, inspection strategies, and ways to protect your pace, whether you’re relocating under pressure or choosing a forever home in Tampa Bay. If you’re ready to spot value others miss, this conversation gives you the frameworks to act with confidence.

If this episode sparks ideas or helps reframe your next move, follow the show, share it with a friend, and drop us a review with your biggest takeaway. Your feedback helps us bring more expert voices and sharper insights to your feed.

Thank you for tuning into "Snapshots Tampa Bay with Candace and Lisa." We're thrilled to share our insights and adventures with you. To keep the conversation going and explore more about Tampa Bay and Central Florida real estate, connect with us on social media and other platforms!

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Transcript

SPEAKER_02 0:05

Hi, buddy, and welcome to the next shot of Tampa Bay with Canvas and LinkedIn. Whether you're sorting out the military moon, checking out this senior living scene, or just on the hunt for the coolest local spots, let's get started and have some fun.

Meet David: Pilot And New Agent

SPEAKER_01 0:28

Hello there. It's Candace here with Lisa. Hi Lisa. Hey, how are you doing today? I'm great. We're excited to spend some time with you today. And today we are introducing a new team member, Olivia.

SPEAKER_02 0:41

Oh yes, I'm so excited. I'm so excited because I kind of I think kind of talked him into coming and joining our team. He's actually we have a mutual friend. And in reality, we found out that we are from the same town, Spring Hill, which is crazy to think about because how not a big town. It's not big, it's not big. So I'm super excited because I love his background. And actually, I was just talking to my my son about your flying video. So David Payolillo, he actually was a fighter pilot, and he's actually still working in the commercial um field. Yes, you're a commercial pilot. So we want to learn a whole bunch about you because you're super interesting to me.

SPEAKER_01 1:29

So and we're happy to have you on the team. Yeah.

Lessons From Moving And Remodeling

SPEAKER_00 1:32

Perfect. I'm happy to be on the team. Thanks for the opportunity. Hi, everybody. Uh yep. So I spent a pretty long career in the Air Force. Yeah. Um lots of moves. Um and during those moves, I kind of figured out that I had a kind of a passion for finding cool places to live and uh making the best out of situations. Um so one of the really cool opportunities to when you move a lot is that you get to learn a lot about not just one housing market, but markets all over the country. Uh, and in our case, my wife and I had the opportunity to live overseas as well during our military career. So that was really cool. And uh it gave us an eye of picking out a house that uh may not be ideal, but making the best of it and turning a house into a home, which we kind of got pretty good at towards the end of my military career.

SPEAKER_02 2:21

Well, you actually I've seen pictures of some of the work that you do, and you actually have done remodels on your own and a lot of woodworking and built-ins and all this different kind of stuff that other people don't take on.

The Phoenix “Ugly Duckling” Equity Win

SPEAKER_00 2:34

Correct.

SPEAKER_02 2:35

Yeah.

SPEAKER_00 2:35

So we we put a lot of trust into who we used as our agents, especially as buyers' agents. And so this one particular agent in Phoenix, she was fantastic, and she said, Hey, come go look at this house. And it was a house that my wife and I had disregarded when we were flipping through hundreds of homes. It was not, it was the ugly duckling on the street, and there was really no way that we were interested in buying it. We looked at it, she talked about the potential. She said, Look, the bones, look at look at the neighborhood, look at all these other intangible things that you can't really get from a listing, which was awesome. And once we started to kind of peel back what we could do, what our budget was, what the potential was, sort of opened our eyes into the possibilities, and we doubled our equity in four years.

SPEAKER_02 3:23

And okay, so we have to do a call out to this agent also because we will tag this agent. So anybody who is in where Phoenix, you said?

SPEAKER_00 3:32

No, she's now moved, and uh, and so and so I I'll have to get updated information and we can add it as a link at the bottom. Yeah, but uh been fantastic agent and uh the spouse of a of a military member, so some established trust there.

SPEAKER_02 3:46

What's her name?

SPEAKER_00 3:47

Isabel Potter.

SPEAKER_02 3:48

Isabel Potter. Okay, so I have that on my list now too. Absolutely. Yeah. Okay, so I've sat down with David a number of times. We've talked. So I want to get your perspective on you know, different things that you want to ask him as far as like his even his military background, because your husband is military background as well. So you may have a couple more questions for him that I may not have had just because you did you have military within within your family as well.

Military Moves And Home-Buying Mindset

SPEAKER_01 4:18

Yes. And I love that you had an agent that was able to see a vision in a home because you take clients out so many times and they're like, I don't like that paint color, or that's the feedback you get from other agents. The walls need to be painted. I'm like, okay, your client can paint that, like it's the promise priced due to those reasons. And so I love that your agent was able to help you envision that because that's really, really important. And because you've had that experience, I think that's going to help you be a great agent as well. So yeah, I don't really have a lot of questions. I mean, we've had a lot of conversations as well. Um, I love that you still fly also, um, and you show us pictures all the time of you up in the planes. I also know what airports aren't great to fly in and out of. So if you want to tip uh talk to him about that, just reach out to him directly. Um we're just really excited to have you on the team. I think your background moving a lot, even overseas, because we're in Florida, right? And a lot of people buy property that are overseas and buy property here in Florida. So I think that background will help you as well.

SPEAKER_00 5:23

Um, you haven't really lived until your king-size bed has to be lifted to a second story by a crane because it won't fit in the front door. True story.

Overseas Living: Space And Lifestyle Shifts

SPEAKER_01 5:33

Well, I sometimes look at these like shows where you're like moving to France or whatever, and I'm like, we'd have to sell everything because nothing's gonna fit in those places. I don't think we realize how spoiled we are in the states with like the size of kitchens and the size of primary bedrooms and things like that. So I would love to hear more about that.

SPEAKER_00 5:50

Oh no, it was really cool living in England. I mean, we had to go to the grocery store four or five times a week by virtue of the fact our refrigerator was about half as big as most refrigerators in a US home. So little things like that that you don't even think about um living in what was a fairly modern home in England was still totally different than any experience that you would find in a in most US homes. It was just uh just different.

SPEAKER_01 6:15

It was really, really I think that's also like a city-like thing. So I'm sure people in New York City probably experienced a similar thing.

SPEAKER_02 6:21

I mean less space, smaller, smaller um footprint, you know, that that sort of thing. And you know, I think it's super interesting. And your wife, Katie, who um she also is a pilot.

SPEAKER_00 6:34

She is so you guys we're not busy at all.

SPEAKER_02 6:38

Not busy at all. And and the one thing that I will say is we also have sons who are in hockey, that's right, which is a full-time job in itself. But it like for you personally, you moved here not too long ago. I actually helped you in purchasing your home and you moved here, and that was your last move that you were doing.

Settling In Florida And Choosing Roots

SPEAKER_00 7:01

That's the hope. Yes. Yeah. I mean, but being in the military and and living a lifestyle where you practice moving to the point where you become professional at it, you sort of feel weird when you don't have a time clock ticking saying, hey, it's time for your next move. So almost, you know, military families, when they when they separate or retire from the military, almost feel this compulsion towards getting ready for another move, even when they don't have to. Um, so one of the most challenging things for us as a family has been to choose a location that was purely our choice, that nobody told us we had to go live there. We chose it, and now any of the pros and cons of that move are all on us, and we can't cast the blame on anybody else because we picked it. So that just just living with that and having to navigate those challenges is really interesting and something that I don't think a lot of people realize, whether you're a military mover or or somebody who has a job that requires you to move all the time, those are unique and different challenges, is that you move into a home already thinking about your exit strategy instead of moving into a home saying I'm gonna be there for 20, 30 years.

Supporting Military Families In Transitions

SPEAKER_02 8:18

That's so interesting because I have zero concept of that. I really do. And even when my husband and I moved down here six and a half years ago, we were like, okay, this is our house for three years. We're gonna just figure it out. It's six and a half years later. Right. And I'm like, no, no, no. We don't, and but most people don't do that. Most people do change their homes. The average at this time is between five and seven years that people change their homes. I think that it's interesting because correct me if I'm wrong, when you're moving in the military, the military says, okay, here's this and here's this and here's this, go. But you may have a spouse who has to pick out that home for you and you have nothing to do with it. Their power of attorney, you know, you may be overseas and the spouses at home with the kids and things like that. So I think that in reality, the spouses need so much support during that. And that's what we want to focus on, especially within our team, because we're all affected by that. My my father is, as some of you may know, my father is in the veterans memory care um facility. So we're all affected, you know, by in different ways. Your husband, you personally, and your wife.

VA Loans: Myths, Speed, And Strength

SPEAKER_01 9:34

Well, and I like that you brought up because we've discussed this when we discussed VA loans. And um, a lot of times I'll see on a listing the agent says, we don't we're not gonna accept a VA loan. We were denied an offer, even though our offer was higher on a home because we were VA and they didn't want a VA loan.

SPEAKER_02 9:53

Actually, it's more it was.

SPEAKER_01 9:55

And you just said that you were very we have to when you're in the military organization. I don't think sellers or other agents understand that a VA buyer is probably way more organized than a non-VA buyer when it comes to the buying process. They've done it so many times.

Tech-Enabled Remote Home Tours

SPEAKER_00 10:13

Oftentimes they're they're motivated by a timeline too that other buyers aren't up against, and they're motivated to get things done quicker, more efficiently, and in a in a swifter time frame because of external pressures that other buyers may not have with more flexibility in their move and things like that, too, which can benefit a seller. Yeah, you know, a seller is wanting a quick close, wanting the deal to go through quicker, and some people see VA and think it's gonna take longer. When in actuality, a lot of time the pre-approval and all those things make things actually happen more efficiently. So um, I think an education piece is huge. The other thing to kind of piggyback on what we were talking about with military movers is technology has changed how military families move. Whereas maybe 30, 40 years ago, if you weren't at a property looking at a home, it was really hard to glean from pictures what it was offering. Now, with so many resources on the web, and then the ability to even do a walkthrough via FaceTime, which which I have been a part of personally. I have to buy a walk. Where you can do a FaceTime walkthrough video walkthrough, and and in some of the high definition videos and things like that, you can get a really good, really good sense of a property. And and the idea of buying a house I don't see, you know, deck a few decades ago was probably unheard of, but but now it's actually quite common.

Why Real Estate Fits A Pilot’s Brain

SPEAKER_01 11:38

Well, and I always make sure that I walk outside in the neighborhood too, so I can see the neighborhood as well. I'll even walk. I've my last buyer, I like walked down the street instead of in the whole street, just because it is easier when you're far away to do things now, technology, if you've got an agent that's willing to do those things.

Mindset, Preparation, And Negotiation

SPEAKER_00 11:56

So, all these experiences I think are motivating for me to the number one reason to do this is kind of a passion for home finding, home buying, home remodeling. These are things that I really enjoy. My wife and I really enjoy that. We've done it so many times that I feel that I can bring a lot of that experience to help buyers and sellers with the experience. Um, and it's just something that's so uniquely different from flying, um, which is which is um which is kind of a cool opportunity. So, Lisa, thanks for for allowing me to be on your team, Candice as well. And uh I'm I'm excited about the opportunity moving forward.

SPEAKER_01 12:37

You've already like motivated us in different ways because you totally it's always nice to get like fresh perspective and somebody coming in and fresh energy. So we're super excited. I think I think we both have kind of like raised our energy. The holiday time this time of the year, we tend to like slow down as real estate agents, and we're not because we have a new team member and we fall down.

SPEAKER_02 12:58

I'm gonna say this too. If you don't know, he also had a podcast before. Oh, that's right, yes. Yeah, so we need to talk a little bit about that because you have experience. So our mutual friend introduced you to me, even though I went to high school with your sister-in-law. Right. We found out seven degrees. Kevin Bacon, you know, yeah, totally, totally. So, um, so Curtis, um, who used to uh be here in the Tampa Bay area, his son played hockey with my son. He moved, but you guys had a podcast already, right? And it was for, correct me if I'm wrong, it was for people in high positions or high achieving positions, and just kind of talking through the process mind mindset and and different things in that way.

SPEAKER_00 13:51

It was, yeah. It was called The Walls Within The Mental Journey to Elite Performance. And the goal was for young people and and everybody really to sort of understand that a mental health conversation isn't just have it doesn't just have a negative connotation, it can have a positive connotation in how you handle the mental challenges of anything that you want to be high performing in. Yes.

SPEAKER_02 14:16

Well, I just had this conversation with my son. So my son is in Boston at the time playing AAA hockey. He lives with a billet family, that's what it's called when you have a host family. And we were up there before Thanksgiving, talked to his coach, and just you know, the coach said wonderful things about him, but we all agreed that mindset in anything that you do, it's imperative to be to always think mindset is key. Mindset is key. So I mean, it you're right, it's so important. And I will tell you, in real estate as well, it's very important, it's very important because you are going through the ins and outs of everything. There's changes constantly, there's lawsuits, there's forms, there's this and that. And if you don't have the right mindset in this, to keep up with it, it it will because behind the scenes, the work that we do is a checklist of about a thousand. And people see three things on that checklist on the forward side of things. So the whole preparation up to that, the checklist up to that, all the subject. The closing process, the closing process, knowing the contract, everything that you do, it's all mindset. And in reality, so is negotiation. Negotiation is mindset. So who am I dealing with? So I think that that even that background, absolutely.

SPEAKER_01 15:59

I mean, and we we you and I both have dealt with agents on the other side that clearly didn't have right mindset.

SPEAKER_02 16:07

Yeah.

Staying Ahead Of The Deal

SPEAKER_01 16:08

And we for us to have to like agree then count to 10 and be like just calm down and not reach their level of notes.

SPEAKER_00 16:17

One of the one of the important things about mindset is comes with preparation, it comes with being prepared, knowing um we have a saying in flying, um, you want to deal with the closest alligator to the boat and handle that, handle that as it comes, and then don't handle the alligator that's 100 yards away. So maybe that's a good Florida analogy. I don't know. Because as you as you go through the checklist and as you figure out and as you prepare and know the steps that are coming, again, in the flying world, we have a thing, we want to stay ahead of the airplane. So in the real estate, I think the translation is we want to stay ahead of the deal. We we want to stay a step ahead so that we're not surprised, so that if the train comes off the tracks, we can get it right back on because we're already thinking the chest move ahead. The the antithesis of that is hanging on the stabs. So if you envision an airplane flying along, if you're ahead of the airplane, it means you're thinking ahead of the airplane. But if you're hanging on to the stabs, which is at the back of the airplane and you're just holding on, the airplane's flying you, and that's a bad place to be. So, in any kind of real estate deal, you want to stay ahead of the deal. When you're flying an airplane, you want to stay ahead of the jet. When you're driving your car, you want to stay ahead and think a few moves ahead so that you can maneuver out of dangerous situations. So I think all of those mindset, being prepared, all that kind of applies to how you handle anything that's stressful that has huge implications for most people. Buying and selling a home is the number one financial transaction that they'll ever experience with the biggest absolutely amount of zeros at the end of it.

SPEAKER_01 17:54

Yeah, absolutely.

SPEAKER_00 17:55

And that's a big deal. Um, and so helping them through that is huge.

SPEAKER_02 18:00

I think that's a great way to end with totally. Now you understand why. Now you understand why. So we have to change the picture, we have to change the team picture, we have to get some some David on there. So thank you so much, and thank you for bringing your energy and being a part of this project because fresh perspective, fresh ideas, yes, partnership.

SPEAKER_01 18:25

We love it, and we're happy to have you here.

SPEAKER_00 18:27

Thank you, guys.

SPEAKER_01 18:27

Yeah, so until next time, stay curious, stay driven, and keep chasing what moves you. I'm always chasing what moves me. Always moving.

SPEAKER_02 18:38

Bye! Bye. Thanks so much for joining Snapchat's Tampa Bay. Hit subscribe to catch our latest episodes and let us know in the comments what you want us to explore next. Keep loving the Tampa Bay vibe. See you guys soon.