Ep 478 After the Deal: When Can You Afford to Fly Private? with Preston Holland
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Hi there, and welcome back to another edition of Built to Sell Radio, the podcast designed to help you punch above your weight in a negotiation to sell your company. Now, before we jump in to today's episode, as a reminder, in 2025, we're going to be

We are featuring four types of episodes. Inside the Mind of an Acquire explores the perspective of buyers. Mastering the Deal gives you the tools and techniques for planning a successful exit. And Exit Story features founders who recently sold their companies and lessons they've learned. And then there's After the Deal. And After the Deal is all about what happens after the ink dries. Now, we launched this series to explore the personal, emotional, and financial challenges of life

post sale. It's all about the opportunities and sometimes the hurdles.

that come when work becomes a choice, not a requirement. Today's guest, Preston Holland, is the author of Private Jet Insider and one of the most foremost experts on private aviation. Now, flying private is a bucket list item for a lot of founders, but Preston will show us it's more of a luxury. It's a tool to buy back time, boost productivity, and unlock new opportunities. Preston also answers a question many entrepreneurs are asking,

When can you afford to fly private? Whether you're growing your business or considering life after an exit, this episode has something for you. Without further ado, here is Preston Holland. Enjoy.

Preston Holland, welcome to Built to Sell Radio. Great to have you. Yeah. Hey, thanks, John. I really appreciate the invite. I'm really excited to be here. I think I work with a lot of clients that I think listen to your show. And so that is a it's super exciting for me to get to come talk to you.

No, that's really generous of you to say. So our audience has just heard your bio and sort of the context for our conversation. So I mean, maybe just walk through as a starting point, how did you become one of the world's leading experts in private jet travel? Like, give me your backstory. Yeah, it's actually far less of a romantic story that I think that you're hoping for. I

I worked for an aviation media company and started basically just started tweeting pictures and images. And I had some access to a few data products that would kind of tell you how much it costs. And, you know, there's nothing better than posting a bunch of pictures of beautiful private jets, right? Because everybody says, oh, yeah, I'm totally going to retweet that. Like,

it's interesting in my threads at the end, I put, hey, be sure to retweet the first post because your friends will think you're cooler because you're retweeting about private jets, right? And so there's this like natural idea of kind of positioning and stuff. So I started having all these tweets go viral. This was back...

you know, back in the day when it was Twitter and not X. And that social media platform has always been my favorite one. In kind of a previous life, I had to interact with a lot of folks on there, kind of in service business Twitter. And so that helped me, you know, gain some notoriety and instant, you know, street cred, if you will. And so...

Started tweeting about it and really, you know, became a student of the industry. I stood up an aviation finance division inside of that company. And so then, you know, kind of started...

tweeting about what financial profiles looked like of clients who were buying what type of jet, right? So I had a client that was worth, you know, $250 million buying a $5 million airplane. Everybody wants to know what that ratio is, right? Like, when can I actually afford this versus when can I, when is it a stretch, right? And so I started doing that. And then I began answering the same questions

questions over and over again, kind of in via DM. And from accounts that frankly had no business DMing a very small account like mine that were sending in like very complicated questions. And I was lucky to kind of have a roster and bench of friends in the industry that could help answer a lot of those questions. And so I'd go ask them and then they'd answer and I'd send it back

So I figured, you know, instead of answering this question over and over and over and over again, why don't I just write a newsletter? That way, if they ask the question, I can send them a link and say, read this first. And if you have more questions, then you can ask me.

Uh, so I started writing the newsletter, um, and it really, you know, grew really quickly. And, and there's a lot of people that are super interested in, in flying private. So, uh, I think we're, I haven't checked this morning, but we just crossed 1300 subscribers of people who fly private. So, uh, so yeah, so that's, that's kind of how, how I got here. And it's a, uh,

It's a lovely industry. I mean, you know, it's like I said, it's really a topic nobody dislikes. Right. Except for maybe some climate activists and and people who, you know, the eat the rich crowd. But, you know, for the most part, right, people think that is super interesting. And so I'm really lucky to get to do what I do.

But it's also one that people feel a bit squeamish about talking about, right? Yeah, exactly. Like, this is obviously a very, you know, elite thing to do. And so people aren't always super comfortable being pretty public about it. So we're hopeful that today we can sort of, I don't know, shed some light on the kind of range of options there are for flying private and so forth. Before we go there, you mentioned getting DMs. And I think you said...

One of them is sort of when can I afford to fly private? So we're going to talk about that at the end of our conversation today. I'd just be curious though, like what are two or three other very common questions you get on DM? Yeah. So, I mean, the number one question is how much is it going to cost me to get from X to Y? That is like by common, you know, very, very common. And the answer to that, usually what I do is I'll say, okay, look,

Sign up for my newsletter. Over the first 10 days or so, you're going to get a series of emails that's going to walk you through the difference between charter and fractional, owning your own plane, and

And then you're going to get a series of four emails that breaks down the types of aircraft and roughly how much they cost to fly. Right. So in a charter scenario, which is a one off kind of one transaction, kind of like calling an Uber or taxi, if you will, you can expect those to be anywhere from 40 to 50 percent margin on the direct operating cost. Right. So that's just kind of like a very rough general back of the napkin math.

understanding, right? So if it costs $1,000 an hour in direct operating costs, you can expect to charter for $2,000 per hour. And then you calculate the distance between the two, multiply the hours by the cost. That's roughly how much it's going to cost you to get there. So one option is we talk about this landscape or from like, I want to go from New York to LA. Right. Okay. So one option is to charter a plane. Yep.

So here, let me break down to you. There's really, the way that I frame it for people is there's four ways to fly private, right? Great. And the bonus way is fly on your friend's private jet and you don't have to pay. That is the best way to fly private. For everybody listening, the best way is to be friends with somebody who owns a plane and you don't have to pay. Okay.

that is not reality for everybody. And each of these ways varies in level of commitment, right? And we're going to go on a sliding scale from the least committal to the most committal when it comes to private aviation. So the least committal way to fly private is what is referred to in the industry as ad hoc charter, which is Latin for, I think it's

ad is like out of, right? So it's like out of one, right? So it's like one off, one time you pick up the phone and say, I need to go from New York to LA and that's it, right? I'm not coming back. I'm just going one way. And they say the price is, you know, $100,000, let's say, because that is a pretty realistic price for that trip for an airplane that size. Yeah.

Because it's five hours and you need a big plane. Yeah, five hours, you need a big plane. You know, Teterboro has landing fees. You're probably going somewhere in LA that's got landing fees. Like, there's just a lot. Like, if you have more than six people in a large cabin plane, you have to have a flight attendant, right? So, there's extra costs associated there. And you're flying on...

at least just what's called a super mid, which would be for those that are, you know, at least sort of playing geeks would be like a challenger three 50 or 3,500, um, or a citation sovereign, uh, can make that trip. That's kind of like the smallest plane that you can be in. You're not going to, without stops, you're not going to fly in a,

King Air from New York to LA. You're going to stop at least twice. And so, yeah. So you're going to get that trip and you're going to say, okay, cool. And you're going to wire the money in because this ecosystem exists with charters and carriers, similar with brokers and carriers, sorry. Similar to if any of your listeners are in the trucking industry, very similar to

The carriers are good at one thing, and that is moving trucks. In aviation, the carriers typically are good with one thing, that's flying and maintaining airplanes. Customer service and customer acquisition is not necessarily something that they're very good at.

So that's where the broker ecosystem creates some of that balance of supply and demand. And so there's a large broker network that doesn't have actual direct capacity that they can't actually fly you on the plane. So, uh, they, you would call a broker and then the broker would say, okay, my goal is to go find you the most competitive, best option based off of your parameters that you've given me, passenger count, distance, uh,

How long is the runway? What are my preferences, right? Do I prefer a stand-up cabin? All those kinds of things. And then, so they go find that operator. So they may call 7 or 10 or 15 different operators. And there's a couple of load boards that they'll use. And they'll basically establish, hey, this trip is happening. We want your bids. And then they get bids and they call you and say, okay, we've got these three airplane choices. Usually it's three.

You pick one, you wire them the money. And that's kind of tying in that other common questions is everybody wants a good charter broker that's not going to walk away with their money because you just never know on the internet, right? Like if somebody is really good at pay-per-click, then...

That doesn't necessarily make them a really good reputable charter broker. Those two things are not, you know, synonymous. So they'll say, hey, do you have a good recommendation? I've got a couple that I'm friends with the CEOs. And if they walked away with, you know, a large sum of money from somebody that I sent them, then...

I know where they live and I would show up at their house and be like, hey, that's not cool. Like you're damaging my reputation, right? So there's another common question you get, but you would wire them the money to basically secure the trip. And then you would fly the trip and you walk away and you're done. You never have to do anything else with that charter broker. You never have to fly private again if you never want to, right? So charter is the least committal way to fly private out of all options out there.

Before we go to the next committal way, how do I find a charter broker? So typically... Other than the internet. Yeah. So let me tell you how, unfortunately, this typically works. And this is part of the reason why I think I have such success with writing a newsletter about this topic is because if you're sitting at the bar at the country club, right? So like, let's say you belong to some nice country club, right? Yeah.

There is like a non-zero chance that somebody sitting at the bar there also like flies private and you're wondering about flying private. You would never know. They won't tell you. They're not going to flaunt it. It's not going to come up in casual conversation. Like it is a taboo subject. Typically what happens, and this is a very big word of mouth business where you'll be sitting, you'll be friends with somebody and you'll kind of say, hey, I'm

I've been, I'm just wondering what kind of the cost would be for charter and they'll go, oh, well, one time I called this guy secretly, they're a $500,000 a year spender with them. Right. But it's like this, it's this awkward like interaction. And so it's a lot of word of mouth. Right. So they may say, hey, I use this guy. They're good. And so a lot of times that's what ends up happening with kind of what I do is I'm

Hey, I know on Google or Instagram or, you know, there's a guy named Colin with the Malfi Jets. He's on TikTok. He's actually legit, to be clear. I'm not saying that he is a scammer, but I'm saying that just like...

His business is legit, but just because you're good at the internet does not mean that you have a legitimate charter business. It's like any good. And so what I will do is I'll basically say, hey, look, here is a charter broker that's not going to rip you off. They're not going to take your money.

they're actually going to fly you. I have other clients and other followers who fly with this person who have then given me feedback and said, hey, I liked this, didn't like this. And then I feed that back. Right. So it's a lot of like it's word of mouth is like typically how this business exists. And there's I mean, there's a couple of magazines that have like big lists. But again, if you pay to play, it doesn't necessarily mean that you're like good at what you do.

It sounds like, you know, a lot like finding a great M&A professional. Exactly. Finding a great professional. Oftentimes, word of mouth is the way you find those individuals. Yeah. And so, okay. Yeah. And like, and I mean, in my day-to-day business, so the newsletter is really a passion project. I do it because I like it and not, I mean, I don't make a living on it. I have a sponsor. So shout out to Ramp for being my sponsor for this, for the newsletter this quarter. But yeah,

That's not necessarily how I take home the bacon. How I take home the bacon is through aviation finance, right? And it's the same way. You're not going, hmm, let me go Google the aviation finance guy. Like you're asking somebody else in your acquisition team to say, hey, who's the finance guy? And hopefully that's me. So anyways, it is...

It's very challenging to find really high level professionals. And through the newsletter and through Twitter, I have helped

people find... All right, let me see if I can think through this. I've helped people find charter brokers, buy jet cards, buy whole airplanes by finding a really good fractional provider, sell whole airplanes, sell future positions in airplanes, buy future positions in airplanes, finance aircrafts,

And a couple of people buy fractional shares in aircraft. And then I've connected two partners to buy an airplane together. They both read my newsletter. I said, hey, you're here. You're here. You're both wanting to do something really similar. You would never know about each other, but you guys should talk. And so like... What a world you play in. It's awesome. Yeah, it's super interesting. But it's like, it's taboo, right? Like, you're just not going to talk about it.

Yeah. So that's why we're doing it. So let's go to the second, the next highest up the ladder in terms of commitment. So leased is ad hoc charter. Where do we go from there? So from there, then we would move into what would be called a jet card or a jet membership. Right. And so this is basically what you're doing is you are buying. It's not like a timeshare. It's more like a deposit account that you then spend down over time.

So some very popular ones, NetJets has a really popular jet card. Sentient Jet, who created the jet card, they actually invented the idea. It's owned by the company that owns FlexJet. That's another popular one. And then Outlier Jets, Thrive has a jet card. They're in Vegas. Like there's a lot of these kind of like... You have like a couple of big national players and then you have...

a bunch of like small or medium sized regional players. You as an M&A guy will appreciate this. This is just like, sorry, and sorry that there's a little ADD, but it's like, there's all these little things that kind of interweave here. But as an M&A guy, you'll appreciate this. Our industry is so fragmented. Like you, it's not even like 20% have 80% of the business. It's like 5% have 70% of the business.

And then this like giant chunky tail that like runs out and then it, and it goes all the way to people that operate one or two airplanes. So like it's literally a mom and a pop in a shop that manage one person's airplane because the dollar amounts are so high that you can make a living managing one airplane. Right. And so you have like this like real disparate fragmented, um,

And if you're an M&A professional, please call me before you think, oh, I'm going to go roll all these up. There's a whole lot of complexity that goes with trying to do that. But anyways, so you have these jet card providers, you have this long tail of other people who have jet card providers. The one thing that I want to caution people with jet cards, and this is what, you know, whenever I engage with somebody to kind of formally help them pick a jet card, this is the one thing that I tell them.

is what we are doing is we are also underwriting the financial viability of the company itself, because you're going to put down between $100,000 and $500,000 on deposit with this company. And in the event that the day after you put that deposit down, they go default, you are now a $500,000 unsecured creditor

against their business. And I will tell you this, they go under, you're behind a whole lot of people. And this has literally happened multiple times in this industry. Like this is not, I'm not speaking to boogeyman. I'm telling you last year, there was a company that went under that told their Jet Card members, you're not getting your money back. Sorry, we don't have it.

Wow. Which is why I guess NetJets, the Warren Buffett company has gotten so much notoriety. Exactly. So how small a card can you buy?

Where does that get you? What's the entry point? Yeah. So entry point there is going to be... I mean, really the smallest card that you're going to get is about a $75,000 card, which will buy you one or two trips. Some of the advantages that you get with the Jet Card is you get guaranteed pricing, some availability stuff, right? And each card is literally priced...

completely differently, right? Some have minimum hours, some have no minimums. So like, for instance, if you had a card with a two hour minimum and you wanted to fly one hour away, you'd have to pay the two hours. Like that's your minimum charge that you're going to get. And,

And so, you know, really buying a Jet Card or a Jet membership, right? XO is another kind of big membership that a lot of people have heard of. What you're buying is you're buying some a little bit of easy button, right? So you probably don't have an assistant that you just say, hey, I'm going here. And then your assistant handles all of that, right? You probably are...

you know, doing this yourself. You're texting the provider yourself saying, hey, I want to go from Miami to New York, right? And so, you know, you're buying a little bit of the easy button. You're also buying some guaranteed pricing. On the flip side of that, and this is not a knock against Jet Cards, it's just kind of a reality. And when I talk to clients is when you participate in the market,

of charter because charter is a market, right? It's a bid ask market where somebody's willing to pay this, somebody's willing to do it for this and they meet in the middle. You don't get to participate in that when you're in a jet card. You're just kind of locked in. So it can create some weird incentives for your jet card provider if they're not good and valid.

highly reputable, because let's say they sold you a jet card with a guaranteed fixed rate of $10,000 per hour. And you want to take a trip and they are contractually obligated to fill that trip to you at $10,000 an hour, which is your contracted rate. They go to the market and all they can find is $11,000 an hour to them cost,

that are out there. So they're going to be losing $1,000 an hour to fly you, but they're contractually obligated. But they're not going to lose money. So they're going to go find the 1985 Falcon 50 that's technically...

within contract for you. And they're going to put you on that because they can get that for $9,200 an hour, right? So they can still make $800 an hour. It creates these like weird like incentives and like almost like

adversarial relationship with your customers as opposed to with ad hoc charter, they need to go find you the best deal, which is not necessarily the cheapest, right? Or it's not necessarily like they want to provide you the most value. So sometimes these jet cards can like, it creates kind of these weird activities. But the

But the brokering deal, the first one you talked about, you know, there's some complexity there, right? Like you've got to spec it out. You've got to have someone like it. Whereas as you describe a NetJets card or similar XO, whatever is the easy button. It's like, it's taken care of and you don't think about it. You pay a premium for that though. Yeah. I think you're right. Got it. Yeah. And you have a difference. Like there's a difference in jet cards. So, so you have like, so jet cards for companies that own airplanes. So that's NetJets.

uh, technically sentient jet cause they get access to the flex jet fleet. Um, and then FX air, which is flex jets kind of premium jet card provider. Um, XO jet cause they are owned by Vista global. So you fly on Vista airplanes, um, thrive out of Vegas. They have their own fleet. Um, jet links is another one. They're,

kind of nationally based. They have their own airplanes they fly. So that's kind of like, right? Like you're flying on there for the most part, you're flying on an airplane that they own. Their badge is going to say the company that your jet card is, right? Like it's, it's pretty like what kind of what you would expect, right? You're not going to buy a NetJets card and then go fly in a flux jet phenom. Like that's not like that doesn't work. Yeah. But then you have kind of these other card providers, which are, they're actually brokers, right?

But they have created a card because their clients have asked them to for some reason. And so they've created this like guaranteed pricing fixed model. It's how Sentient Jet started before they got bought by FlexJet.

And really what they're doing is they're going to go broker the trip anyways. They're going to go find you capacity, whatever's out there based off of your fixed rate. And there's some tax advantages. I mean, like when you buy a jet card in December, right? Like everybody buys jet cards in December because they want to spend that. Like you can recognize some of that, right? So like there's tax advantages to it. But really what you're doing is you're prepaying your brokered trips at a fixed rate. And now you're not participating in the market anymore.

So like, let's say... That's a terrible deal. Yeah, right. It can be a terrible deal. Like, let's say the Friday, like the Thursday before the Masters is like, there's like, NetJets won't, NetJets card won't even let you fly Masters weekend, period, right? Like, they're just like, we're not going to have any capacity for you. So it's a blackout date. Like Masters, Super Bowl, Christmas, Thanksgiving, whatever.

Memorial Day, Labor Day, like the 4th of July, like there's all these like super in demand, right? But if you're, you know, if you're some guy trying to, I don't know, go play golf for a weekend and you're like, oh, well, instead of going master's weekend, I'll just go the next weekend. Like it doesn't matter to me. You can save 20, 30 grand, right? Like on your charter trip.

But you can do that. Like, but if you're locked into like a jet card, right? And you're paying seven grand, whether you like, regardless of what day you go, right? Like...

You don't get to participate in the market ebbs and flows and like saying, oh, like here's a, you know, here's a way that I can kind of like maximize my spend, if you will. So like this again, all jet cards are not evil. Not all jet cards and jet memberships are terrible. It's just like, you have to know a lot of these nuances when you're analyzing them and they're not going to tell you, they're not going to be very forthcoming with like, Hey, here's a nuance to our jet card. Right. Like,

fuel surcharge, we put that in there because that basically lets us charge whatever we want, right? Because we can just say, ah, well, there's a 40% fuel surcharge, right? Like, okay.

Fine. Right. But like, don't call it guaranteed pricing because you're setting an artificial floor and no ceiling. Right. Whereas when you're brokering, you know, the provider takes the risk on that. You agree to price and whatever, you know, extras. Exactly. Let's go to the third level of commitment up from there. Yep. So third level of commitment would be fractional ownership. There is a lot of, there's a lot of people that don't understand exactly how this works. So I want to break it down very simply. Okay.

Fractional ownership, which is NetJets and FlexJet, they're the largest two providers. And NetJets is two times as large as FlexJet. To put into perspective, NetJets is the largest, and then there's a giant gap, and then there's FlexJet, and then there's a giant gap, and then there's everybody else. So they're the two largest providers.

you are, there is a capital cost to buying the airplane. And what you're doing is, is you are actually buying a part of that airplane. Like there is,

Think of an airplane divided into 16 parts. And when you buy one 16th, you're buying the wingtip and a seat, right? Like, I mean, you know, or whatever. And you have 15 partners on that airplane. So like there's 15 other guys that are like John and Preston that are out there that also own a NetJet share. That capital expense is just that. It is just capital expense.

Meaning you depreciate it over time. You depreciate it over time. Right. How many years do you depreciate it? Okay. Not tax advice, not legal advice, all that good stuff. But typically what I see is... So airplanes typically depreciate over a seven-year lifespan from... If you're doing straight line, it's typically six or seven years. If you look at the mark schedule...

But you can bonus depreciate it because it's equipment, right? So if you use the asset 51% or more for business and you have a business need for it, right? And you bonus depreciate the actual capital expense. So I don't know when this episode is going to be coming out, but in the United States, there is...

a lot of confidence around 100% bonus depreciation coming back based off of what's happening this morning. And so if you can 100% bonus depreciate, let's say your capital outlay for it is $600,000. And then you can depreciate that $600,000 against...

ordinary income or whatever, right? Talk to your tax professional. Don't listen to some guy on a podcast for tax advice. That would be silly. But if you have taxable income and you can depreciate the $600,000, it creates... It's not really 600 grand. There's just like... It's some fraction of that. The nuance is that at the end of your five-year contract, you sell it back to NetJets

at an actual depreciated value. So, you may buy at $600,000, but your residual value is like $420,000, right? So, you're going to take an actual $180,000 depreciation. This is real cost, right? You bought it for $600,000, you sold it for $480,000, you're now down $120,000. So...

you know, if the most appreciation is worth it to you, right? Like, that's great. But sometimes it's not. It just depends, right?

The thing with fractional is there's no blackout dates. You don't have – like you're treated like an owner, which means that you kind of have a more elevated status inside of whatever company it is that you're at, right? But how do you figure out who's going to take the jet on what weekends and how does – like if I wanted to go to the golf, then you wanted to go to the Super Bowl. You will probably never fly on your own tail number or you may once.

So there's this rule, and this is like really nuanced. And for all the really nerdy people out there, like I could nerd out on this stuff all day. But essentially what the FAA allows is you have what's called, they fly under what's called Part 91K, which is a subsection of the regulation that says essentially for fractional providers like NetJets,

Everybody can fly on the other airplanes of similar size within the program without having to pay federal excise tax, right? So charter and jet cards, you have to pay federal excise tax, just 7.5%. Can't get around it. On fractional, you don't have to pay federal excise tax. So over the life of your ownership, it can save you pretty significant money.

But you can fly... Would those be pretty similar numbers, by the way? Like the 600 grand for a 16th share? 600 grand is about what it costs to buy a 16th of a Phenon 300 at NetJets the last time that I looked.

And you could sell it back to them for 400 and change? Yeah. I mean, they'll tell you anticipate 50%. It is a point of negotiation. And residual value is one of the things that we help clients on is basically say like, hey, look, we're not taking that as an answer, right? Like, hey, you can sell it back to us at whatever market rate is. Like, nope, nope, nope. We are going to negotiate our...

residual value on the front end because you can, right? There's just a lot of things in like this process that like it's all, I think it's all out of good faith, but like it's just, it makes it really challenging to actually like navigate this space without somebody like knows what they're doing, which I frankly, total transparency, I wish I didn't have to exist sometimes like in this kind of world because what it means is that our market is incredibly inefficient and it's

Lacking in customer service. There's a lot of things to not like about having to do this. I mean, obviously make a living doing it, but like... I was going to say, but this is how you make a living. Yeah. Is getting people into a fractional ownership position and then the negotiation associated with that and financing of that. Yeah. Yeah. So multi-vertical, kind of multi-vertical consulting, right? So kind of...

Pillar one would be aircraft finance that's fractional to whole aircraft. Pillar two would be kind of jet card selection and charter, right? So figuring out like we're not a broker, like we're not, we don't have a dog in this fight. We're helping you make the right decision. And then the third one is that fractional piece, right? Because there's a lot of new, there's a lot more nuances to these contracts and things like that.

So we help analyze quantitatively, qualitatively, kind of risk assessment, right? There's two, in recent memory, there's two fractional providers that have gone bankrupt. They kind of caused a lot of disturbance in the very light jet market. So the HondaJet,

Jet is a very light jet. There's two providers recently that have gone, well, first one went bankrupt. The second one kind of divested everything. So the first one was Jetit.

They were selling one 16th shares and promising these hilariously low hourly costs. And they're going to make up for it on charter. There's a whole, you know, kind of weirdness to it. But they went belly up and it created chaos because you own that 16th fraction. And if the manager of your fraction goes bankrupt, you still have that 16th. And now guess what? There's 15 other people that you have to coordinate with to liquidate the assets. Kind of a pain in the butt.

Um, Volado had a similar situation about six months ago where they pushed all their fleet off to fly exclusive. They've, they were publicly traded. They're not bankrupt, but they kind of washed their hands of all of their fractional management contracts and all. I had a, I had a guy reach out to me and he was like, look, I own a 16th of a Honda jet.

The new contract is totally different than what I signed up for. So I'd like to sell it, but I can't get the other 15 yahoos to all agree of what we're going to do. And so it's it can become a mess. But you do own an actual sliver of the airplane.

Okay. So I just want to clarify one thing. So with fractional ownership, you know, I'm going to buy a light jet for a 16th share of a light jet for 600 grand. My, I'm going to negotiate the residual value because I want to be able to sell it back after five years. I,

I get to participate in a network of jets of a similar sort of size and range. Therefore, I'm never kind of waiting for the other 15 guys to agree on when we're going to fly where. The shorthand way to say that is what's called a floating fleet. So if you look, here's like a fun activity for your listeners to do. If you go to flightaware.com,

which is a tracking software, you can actually pull up the entire NetJets fleet at any given time. So you can actually... So like I'm going in right now and I'm pulling up FlightAware and I click NetJets and you can see... Is this a video podcast? Are we doing video for this? No, just video, but we're not doing screen share, but you can if you want. Well, I was just gonna say that like

So maybe like we can like, it says flightaware.com slash live slash fleet slash EJA. Maybe we could throw it on the screen or something. Yeah, share your screen for people watching on YouTube. Yeah, but it's super interesting. So we can, let's see, screen, live, share. Okay. So this is FlightAware. This is like an ADS-B tracker. So this is all the NetJet flights, EJM, right? That's so cool. Executive Jet Aviation is the original name for NetJets.

This is all the NetJets planes in the air right now. Right. So we can go, you know, you can zoom in here and you can see like that is a Phenom 300 that is live in flight right now from Ohio State University. And they are headed to, it looks like Atlanta, Florida.

So at any given time, right? So they're, they're Asheville to Orlando at any given time. If you look up, there's probably an air, a net jets airplane, not too terribly far. What that means is, is like, okay, so there's a phenome 300. Let's see. Where's another one?

For folks listening on audio only, what you're looking at is like a map of the U.S. with like literally probably somewhere close to a hundred little icons of airplanes going in all different directions at one time, which is really incredible to look at. Okay. So this, somewhere over Western North Carolina, like Asheville area, is...

a Phenom 300 and going into Atlanta, here is a Phenom 300. So like there's never a plane too terribly far away from you wherever it is that you're going. So that's like when you operate with like a big, large national fleet,

An airplane of similar size or flavor is probably not too terribly far. I mean, here's another phenom in the Midwest over Missouri, over Nebraska is a Challenger 650, I think.

The point is, if you are a fractional owner in a Phenom 300, you're not necessarily flying on the exact serial number that you're an owner in, but you do get access to a Phenom 300 wherever it may be kind of in the United States at the time. And you also have to pay operating expenses, right? So you drop your 600 grand down to buy a 16th chair. That doesn't mean you get to fly free everywhere you go, right? You still have to pay operating expenses. What would those be on?

if you own, to use this light jet. Yeah. So you're going to pay per hour and then the other piece you're going to pay monthly.

monthly management. So you're going to pay your fraction of the, uh, you're going to pay your fraction of the expenses. So you're gonna pay one 16th of the hanger fees. You're gonna pay one 16th of the insurance, one 16th of the pilot costs. Like you're gonna pay one 16th for every, uh, part of that, of that airplane. Um, and,

And that is typically so like, you know, $8,000 to $15,000 a month, kind of depending on which program that you're with. And it scales up. That scales up with your ownership size. So if you buy half a plane, that's going to grow up in relationship, rises eight times bigger.

And then you pay per hour when you fly. So you don't pay federal excess tax, which is really nice, but you pay direct operating costs. On NetJets, the last time that I looked, their fee on 300s were anywhere from $3,500 an hour to $4,000 an hour. And how many people would that seat? And that would seat six very comfortably. You can get eight people on there. It gets a little tight. Yeah.

And somebody's got to sit in the toilet, which is not... You might as well fly United. I know. So here's a funny story. I have flown on the toilet once. We were on a Honda jet and somebody... We were leaving a conference and I was not the lead passenger and

And so somebody snuck on, not snuck, but like, it was like, oh, can I come in somebody? And who was the leader was like, oh yeah, for sure.

Well, that meant that we were kind of like all strategically arranged around the airplane. And I somehow drew the short straw and had to sit on the toilet. And there is not a whole lot of airflow at that part of the airplane. So we're taking off and I'm like sweat. I'm like drenched in sweat. I'm like, it's so hot back here. And I was like, man, I, you know, had I flown Delta, I was like, I wouldn't be in this predicament. But then...

When I was in my house an hour and 45 minutes at my house an hour and 45 minutes later where on Delta, I still would have been connecting in Atlanta. Actually, I wouldn't even be off the airplane yet. I was like, you know, I think I'd take the toilet on a PJ over first class on a short trip with Delta any day.

And one of the other benefits of flying private, as I understand, is you can get into these smaller airports. So you're not like in Toronto where I fly out of, you know, Air Canada. I mean, it's an hour to get to the air on a good day. And then, I mean, the sea of people is like LaGuardia or O'Hare. I mean, it's just unbelievable. So, okay. So specifically, like, forgive me if I am ignorant on...

Cause I am. Um, but which, so like what, like small town of, do you live in? Like, so I'm, I'm in midtown Toronto, like downtown Toronto, but there's a, there's a small, uh, airfield called Buttonville, which is kind of North. There's another one, uh,

the Island airport, which is right downtown, which, uh, some prop planes fly out of, uh, yeah. Billy Bishop, I guess. Billy Bishop. Yeah. Yeah. Yeah. We're losing every one of my listeners right now. They're like, I don't care about Toronto. Listen, regional airports. We, we love, we love, we love our Canadians with your fake money. And, uh, I'm just kidding.

But look, there are five in the United States. I don't know about Canada. I'm sorry. But I know about the United States. There are over 5000 airports and about 500 of those are serviced by commercial airlines. So you're looking you're talking about opening up a huge world of smaller airports. Atlanta is like one of my favorite examples.

Atlanta is the busiest airport in the world. I think like, you know, any, yeah. One of the biggest, busiest airports in the world is on the South side of Atlanta. Um, for those users that are in the South, that is my like home hub airport. I'd have to drive two hours to get there, but, um, yeah,

It is on the south side of Atlanta. And a lot of the business activity in Atlanta actually takes place on the north side, right? The north and east side. So PDK, which is a non-commercial airport, non-serviceable, is incredibly busy of an airport. I mean, I'm talking the last time I was there last week, having lunch with a friend. And we... I mean, there's probably airplanes taking off every five minutes, either taking off or landing every five minutes. Because...

And they all got to skip the whole downtown traffic thing. And like, it's just way, it's just way better. You skip security, you skip a lot of the, the stupid stuff about flying commercial, sneezing kids and screaming kids and all that kind of stuff. I have a screaming kid that likes to get on airplanes and scream. So to be clear. But yeah, so it, it, it, it saves a lot of time and a lot of effort, you know, when you're flying private.

But that's a really interesting stat. 10 to 1. Yes, it's like 10 to 1. So 500 airports, you can fly Delta or Southwest and 5,000. Yeah.

airstrips that you can land a private jet on. Yeah. So like, I mean, I'm looking, I'm literally looking at the map of Toronto right now. You just Google like city airports and just like see how many dots there are that you're like, okay, so you have Pearson International, right? Which I guess that's YYZ. Yeah. I see one, two, three, four, five, six, seven airports just in like what I would call, what I would guess,

would all be considered Toronto or the suburbs of other airports. Oshawa Executive, Toronto Markham, Toronto Buttonville, Downsview Airport, that's permanently closed, rest in peace. Billy Bishop, Brampton, Culledon. And then, you know, you go down to Hamilton. I don't know where Hamilton is, but like John C. Monroe, Hamilton Airport, International Airport. It's like you have all of these different places that you can fly out of

my neck of the woods within a 30 minute, call it a 30 minute drive of Chattanooga airport. Right there. I can think of seven like airports with paved runways and then for like, you know, grass strip type places that you can technically land at. Right. Like if you, depending on what kind of airplane you have. So it's like,

aviation has, there's this whole other world that like kind of gets unlocked with private aviation that you just don't see from like your major airliners. A hundred percent. So let's go back to the, and I want to get into like, cause I can see and hear people wondering like, when can I afford this? So I want to get to that. But before we, let's just touch on the fourth level commitment. I'm assuming that's buying a plane. Yeah. Buying a plane. So you can do that either on your own or in a partnership with friends and

And the reason why I say so, so to kind of draw an overarching, what does commitment mean when I say the four ways to fly private with various levels of commitment on, on charter, you have zero commitment to the provider and zero commitment to the airplane. If you fly on a PC 12, which is a single engine turboprop,

and you don't like it, you never have to fly in a PC-12 ever again if you use Sochus. There is no commitment level. If you buy a jet card in a PC-12,

You're probably going to have to fly on a PC-12 again, right? Like you're committing to an airplane or an aircraft type, right? So you have light jets, midsize, super mid and heavy. Those are kind of like the big categories. And if you buy a jet card on a light jet and then you get on a light jet and realize that it makes you seasick, like you got some commitment or you have to sell it back or get something that's refundable. Like a lot of like nuances there.

fractional, you're committing to an aircraft make and model, right? So not only are you saying, I like the size, but I like the Embraer Phenom 300 or the Challenger 650, or I like the Gulfstream G650. Like I'm committing to that make and model on a fractional.

Now, you're not committing necessarily to one of those, right? And like all of that and committing to the maintenance, but you're committing to the make and model. Ownership, like you're getting married to that thing. I mean, it's like, this is my plane. Every time that there's a tire that needs to get changed, I'm changing it, you know, all that kind of stuff. So like, it's the most committal way to fly private. So like, that's what I mean, not only like from like a financial standpoint, but also just like committing to like an aircraft. Yeah.

Got it. Got it. So I know my listeners are wondering, okay, so you're throwing out some big numbers, right? And I think our listeners would fall into one of two buckets. You would have people running successful businesses who maybe one day aspire to sell it, but they're good businesses. They're making money.

of 500 grand a year, a million dollars a year. I mean, these are good businesses. Cash flow, baby. What's that? Cash flow. Yeah, they could probably bury some expenses into their P&L that no one's going to really worry too much about. So there's those types of people listening.

who probably have teams and they've probably flown with their team to some event. And they're like, man, there's four of us flying Delta and this is costing, I don't know, 10 grand. And could we have done this some other way more comfortably? Maybe, yeah, whatever. So there's that kind of person. And then there's the person that's about to sell their company and they get liquid. And so while they may not have as much income, they've got some net worth that

So when can they even contemplate having this kind of private jet conversation? Yeah. So let me divide that into those two distinct personalities because I think the numbers are different if you are currently operating like what you said because there can be a tax advantage to flying private or traveling whatsoever, right? So like...

If you're going to fly first class for a business trip versus flying first class because you and your wife want to go to the south of France, right? Like you...

Hopefully, there's not a lot of wives that don't work in the business that are listening to this, but we typically tend to think about that in a different framework, right? Because, oh, I'm going to do this and it's going to... When I hit the ground because I flew first class and was able to sleep on the airplane, now I'm more productive and now I'm able to do more stuff. That is a different frame of mind than...

I feel rested so that I can go to the hotel and probably take a shower and then go do a wine tasting, right? It's just like it's a different frame of mind. So let me talk first to the people who are actively running a business that is generating cash flow, generating profits, doing actual activities, right? So I ran a super informal survey on my Twitter X account.

And I basically said, hey, if you fly private, what income level? So like net income that is like either you are distributing or you could distribute and you may keep it in retained earnings for whatever tax reasons. But what is your net income? What was your net income level? And then your net worth level when you started flying private and at the various stages for you. And one of the cool things about being the private jet guy is

Is that everybody will tell you that as long as they can't get traced back to it. As long as you couldn't go, oh, that was my, that was John Smith, that big Twitter account that everybody knows who they are. And so I got, I got 16 DMs and text messages from people that I know their tail numbers. Like I know, like I, they are legit. They own airplanes. And, and,

It was super interesting. This is very non-scientific. And I think I'm actually, it's actually inspired me to put together like a wealth report that's like actually way more scientific about this. But I was doing it on a whim and needed to write a newsletter in about an hour. So I was like, okay, I just need to find it. And like almost everybody settled on

on $2 million of net income and $20 million of net worth. And let me caveat that with net worth in that situation was even considering business value of their business. So let's say in theory, they're giving themselves a 10X multiple on their business, which is not... Software guys, that's really not crazy for...

HVAC guys in the South, that's definitely not crazy, right? Like there's, there is a value your business the way that you do, but they would net, you know, their net worth of $20 million, they would start chartering. So two and 20, right? And, and look, some were, some were 1 million and 20, some were, I had one guy that was 50 million. He was like, I don't, he's like, I can't,

Imagine justifying it. So every person is different. Like you're different. And don't let me try and convince you to do this. I'm just telling you what other people told me. This is what they were doing. It was two and 20.

And that's when they started flying private on a regular basis, right? So we're not talking about the golf trip with eight buddies and you chartered a King Air and everybody threw 500, 1,000 bucks in the pot and it covered the flight. Like that's not who we're talking about here. We're talking about like, okay, I have a 50-hour, 75-hour jet card. Every time I go to my house in Tahoe, I don't fly commercial, I fly private.

This is, I'm speaking at a conference and when I go speak, I will charge them for the first class fee, you know, plane ticket, but really I'm taking a jet from the local FBO. So two and 20 was kind of the median, if you will, and the mode. Low end would be a million of net income and 20

I had one guy, $5 million in net income and $20 million in net worth. Basically, he was like, "Our net income ramped really fast."

And therefore, I started spending more money on flying private. Obviously, he was still banking it, but he was like, yeah, we ramped really fast. I had a bunch of net income, needed to do some offsets and figured, you know what, this is my goal. And then, you know, kind of the high end was, you know, more like the $20 million of net income, you know, nearing $100 million net worth. So that's flying private for like the first time. Okay, so...

For your informal survey, they started chartering when the net income, the net business income plus whatever personally they were pulling out of the company was $2 million and their net worth was $20. And then for those that were buying a plane, they were, I think if I understood correctly, more like $50 million in net worth. Is that right? Yeah.

Yeah. So like it started at $50 million, but, you know, kind of the buying the plane, like that really started skewing and getting pretty personal. I would say like if you were going to stick like a number on it, it was usually about...

The net worth is actually somewhere closer to 100 million. This is people going out and buying like a mid-sized jet or something like that. Yeah. So 10 million in income, $100 million in net worth was kind of the start. And that would be...

There is a lot of ways that you can buy an airplane, right? And I made this point in that article that you're talking about is if you're buying, like I know a group of guys here in Chattanooga that own a PC-12 together. There's five of them and none of them are worth 100 million bucks. But altogether, I think they're worth, they're probably worth 100, 120 million bucks.

So, usually like a calculation is if you're doing a partnership, the sum of the total of everybody should – is usually around these numbers, right? So, it's about $100 million to $200 million in net worth kind of depending on where you're at stage-wise and things like that. And somewhere from $10 to $20 million in net income.

Got it. And obviously the kind of plane you want to buy, big heavy jets would be more. Yeah, yeah, yeah. If you're buying a global, you're probably looking at $500 million in net worth or more, like a global $5,000. Hey, that's a Canada plane. Look at that. There you go. So I think it's fair to say our listeners are probably more in the – the 2 to 20 probably sounds like, okay, maybe they're not there yet, but they could see their –

see that that could be them in the future, I think. I'm sure we have people in all different stages, but I'm just going to assume that two to 20 is aspirational for a lot of folks. So that's for the person operating a business. What about the other type of person who sells their company and they're not running a company anymore? They're effectively just out. I would say for those people...

My number one suggestion is, is for, if you are truly out of the game, like I was at a retreat with, I don't know, 50 of the most high octane leaders that I've ever been in a room with. Um, it was, it was absolutely awesome. And I'm very thankful to the guy that invited me, but

I had a couple of... I had markedly three conversations with post-exit founders that were, you know, call it 18 months out of the exit. And I mean, we're talking about pretty significant private equity exits, right? We're not talking about, you know, selling to the across town competitor that we're sitting there going...

In about 10 minutes, they're like, what do you do? I work in private aviation. And it usually like that conversation spirals like pretty quickly. Um, and I, I mean, in a good way. Right. Um, but we sat down and he goes, look, he's like, here's the deal. I have to get back in the game. He's like, I can't sit on the sidelines and it has nothing to do with money. It has everything to do with who he is as a person. Um,

And he said, when I do that, I will call you because I'm going to be flying private much more often when I do that because he is call it like post-economic, right? But then...

Like if you're, if it's completely post-tax earnings, right? Like this is super, like it becomes very expensive when it's 100% post-tax earnings. Does that make sense? So if you're in that one, I, my number one piece of advice would be do charters on those trips because you don't want to feel like you have to fly private to earn off a membership or to use up your fractional hours. Right.

I mean, unless you are so post-economic that you don't even have to – you're not even going to flinch, right? But if you're still considering what you spend, do ad hoc charter because then you can say to yourself –

We're going to save eight hours on that trip into Aspen or Colorado Airport that United doesn't go into. And we feel like it's worth that because we're going to bring two other couple of friends that we have and all of our skis. And that's worth it to us. You get to make that decision versus flying United much easier if you're ad hoc chartering than if you're like, oh...

well, we've got 20 hours that we got to use this quarter or else we're going to lose it. Well, we're going to have to fly private, right? Like, I don't know. That would be like my advice. And that's not, I mean, you know, uh,

I don't, I do ad hoc charters. So that, you know, it's not net beneficial to me. It's just like genuine care for people is, is think about ad hoc chartering type situations as opposed to, you know, getting more committal. And I, but I would say that it's probably similar to the number, right? You're probably at a 20 million liquid net worth, right? But

You're probably not spending 200 to 500 grand a year of that on flying private. You're probably more in the 75 to 100 range. Got it. And so-

In your experience speaking with these high-octane entrepreneurs, the idea of – we've talked about this on the show, kind of living off your capital is such an athema for many entrepreneurs. Like their whole lives have been about building and building and building. And then all of a sudden, living off their capital is a terrifying proposition. Even if they built up an enormous amount of money, it's just like so –

not part of who they are. They always need two times as much, right? What's that? They always need two times. It's like if your net worth is 5 million, enough would be 10. If it's 100, that would be 200. Yeah, yeah. But so you're, you know, in your experience, people aren't, you know, so...

to use your term, post-economic in most cases that they don't. They just fly private wherever they go. It's more like they're doing it when they have an operating business. Yeah. I mean, that is like super general characteristic, right? And there's obviously different scenarios. I think the other thing, and this is, I mean, again, what I find is that just because you have sold your company does not take you out of the game and put you on the sidelines. Like,

a lot of what I see a lot of people do is like they may all of a sudden become a real estate tycoon. Right. And it's like, oh, there I have I have one client specifically that I'm thinking of. He sold his business private equity. But guess what? He got to keep all the real estate that all of his businesses operated out of. And he's just leasing it back to the private equity groups. Well, that's an operating business, right? Like it's producing cash flow. It's

you know, has its own set of tax implications. Um, talk to your tax professional before you start writing off private jets for that. But you know, you at least have a fighting chance in that scenario where you're still in the game in some way, or maybe they open up a family office, right. And they're making investments. And if you're going to go meet with an LP or with a GP or with whoever, right. Uh,

There's probably taxable income to write off against that, right? So like I think what I have found, and this is my experience and I'm sure that yours is totally different, but in kind of like the post-sale founders perspective,

you got about six months, six to 12 months before something happens, right? Either they got to go start buying real estate or like they just need to, they have this need to create and to build whatever that looks like, right? If it's starting or if it's starting a business with their kids or whatever, right? So like, I think as in that kind of frame of mind, look, if you're

late 60s and you're like, I'm done. I'm totally going to hang it up. I hope you become a million miler on Delta flying first class. And if you want to fly private a couple of times a year, please don't let me talk you out of it. But what I'm saying is that unless you just absolutely want to blow the money on it, I don't know how you make that justification if you have nothing...

business going on. Does that make sense? Like, is that, I mean, I don't know for sure. What do you see? I mean, you, you talk to a lot of, I actually only talk to the ones that are falling private. So, you know, I, I, I'd appreciate kind of your perspective there.

Yeah, no, 100%. So what I have seen is that when entrepreneurs sell, they go through a variety of motions. There's obviously a period of like incredible elation when the check clears and the zeros at their account. And then generally there is a

a pretty big trough, right? There's a period of depression where they feel kind of lost and they miss the game and so forth. And, and, and usually they come out of it and you're right. I oftentimes they'll start another business or they'll, they'll start building something else. Uh, could be something that that's meaningful to them personally or whatever, but they're, they're usually not just sitting on the beach. That's very rare in my experience, unless they are, you know, at a certain age where it's just not practical, but most of them are looking to build. Um,

And I have also seen and heard on this show, the idea of living off your capital is so, just feels so wrong that it doesn't surprise me that people don't, they need an operating business to justify the expense. And at the same time, I do hear a lot of, you know, I asked this, you know, we interview entrepreneurs who've sold their business. And one of the questions I ask at the end is like, did you buy yourself a trophy?

what was it that you bought that you used to commemorate the win? And now sometimes people say, I bought a car or a house or whatever. But the most common answer to that question is, well, like I invested in some experiences. So I took a whole group of friends and we went to Baja, like dune bugging,

or whatever, right? You know, I went with my kids and we went to ski in Courchevel and they have some experience that they point to that was meaningful. And those experiences can be lubricated enormously and made much more fun by private aviation. And so I can see where the trophy would be something, you know, where people might start to invest or, you know, start to spend some money on these types of things.

Yeah, for sure. And I mean, like my prime, I mean, who do people always ask me, like, who's your customer? Like, who do you work with? I work with business owners looking to buy their time back. Very, you know, plain and simple. Right. Some sort of there is some sort of business entity operating. They are looking to buy time that time is the only thing money can't buy, except they

when you fly private is the only way that you can possibly buy your time back. And so for those business leaders that are thinking about how do I get more soccer games or how do I get more dance recitals or how do I get more time with my spouse and how do I get 10 more date nights per year? And also be this high octane leader and build this business and grow it exponentially.

So like private aviation can make sense, especially if you're in like a tertiary market. Chattanooga is a very tertiary market. And so if I want to go to any other tertiary market, I'm going to Austin tomorrow. So I leave for Austin tomorrow. For me to get to Austin from Chattanooga, I have three options. One is I can drive to Nashville, which is two and a half hours.

Two, I can drive to Atlanta, which is another two and a half hours. And you have to deal with Atlanta. Or three, I can leave from Chattanooga, which is a great little tiny regional airport. And I've either got to go to Dallas, Atlanta, Charlotte, or Chicago in order to get to Austin. Those are my options. That's it, right? So you're looking at, at best, a 12-hour travel day. And at worst, you know, 24-hour travel day.

I have done that trip privately and it's like two hours and two and a half hours like to get there. You know, like the time buyback, I'm not in a position right this moment to say, I'm going to justify it for just me, right? Like that's not where I'm at in my business. But if I had, you know, if it was me and four of my employees going, like, I don't know, that's 48 hours of productive time. Like,

If I'm billing it $250 an hour, it might actually make sense, right? Even from a justification standpoint. But that is a lot of the point of private aviation. And I think that there's this common misconception due to social media or whatever that private jets is just Kardashians.

Private jets, I'll say this, this is a controversial take and maybe a hot take. You can use this for social media, but private aviation looks a lot more like Elon Musk than it does Kim Kardashian. So if you take those two people who have the exact same airplane type. Now, Kim Kardashian is a businesswoman and she drives and she travels for work, right? But there is a assumption of kind of this...

I don't know, like aura around, oh, I'm going to fly my private jet to Vegas. Right. Because Keeping Up with the Kardashians only shows their trips to Milan and to Vegas and like, oh, we're going to go for somebody's birthday. Right. Right.

It looks a lot less like that. It looks a lot more like Elon Musk visiting Starbase, the Tesla factory, the XHQ in San Francisco, and then flying to the inauguration in one day. It looks a lot more like that in 99% of the world than it does, oh, look at me. I'm on a private jet. I'm famous. So I don't know. That's my- It's business owners looking to buy back their time. It's business owners looking to buy back their time.

they're running companies generally with a couple million dollars of net income before they start doing it regularly. And how else would you care? Any other demographic or psychographic characteristics? They live in a regional market oftentimes, not a big major. Yeah, regional market. I mean, look, manufacturing is a big one because it's time-sensitive businesses, right? So...

I have to get from here to there. The line is shut down. And if my industrial engineer doesn't get there, every minute is costing that plant millions of dollars or whatever. So it looks like that. It looks like car dealers with regional car dealers that have all over a state or a region. It looks like construction companies that's moving crews. It looks like

franchise owners that have multi-state franchises, it looks like... It looks like people...

It looks like the guy, if you think about it like this, it looks like the guy who you would never think flies private, but you also would never guess that he has a $100 million business. I don't know if you've ever... I've had this experience so many times, whether it's at church or at the country club or at dinner or at a friend's birthday party, where I get to talk to somebody and

If you know, if you can piece it together, you go, Oh, wait a second. No, you're loaded. Like you, you're doing really well. Right. Um,

Those are the type of people who fly private. You're not going to guess that your local... The guy that you know that owns a construction business, you go, that's cool. But actually, he's killing it. And actually, he sits on a board in Texas and also in the Midwest. And he flies private pretty regularly because now his time is worth a couple thousand bucks an hour. Yeah.

And also can't take it with you when you go. But what you can take is memories that you had with your kids and with your spouse and that kind of stuff. So that's typically who it looks like. And that's all people who fly in the backseat.

there's a whole nother group of people that fly in the front left seat, which is people who fly themselves, which is a similar psychographic and demographic. It's just people that have the desire to learn to fly themselves.

Interesting. And I think it's, you know, when people think about like, what am I going to do when I sell my company? Like, you know, learning to fly is one of those intellectually challenging things, obviously. And, you know, obviously you have the liquid wealth to pay for the flight lessons and maybe a plane at some point for action in one. So, so cool idea. One thing I wanted to ask you about it, just, I wasn't planning to, but it does trigger an idea for me, which is around privacy. So, um,

These individuals that you're describing, we've talked about it several times during this conversation, they want to remain private. It's not something that comes up at the bar, at the country club. You don't flaunt it. Most of these people, you wouldn't know it. How can people who fly private keep it private? Yeah. So it's funny. This is a conversation that I had with a client of mine about a month ago.

They had an issue where they were at a small airport buying a big plane and real hard to hide that you're not the guy with the big plane at the small airport. And so there's a couple of ways that you can do it. Ultimately, so Jack Sweeney created the Elon jet tracker and got into a lot of hot water with him and Taylor Swift and a couple of other people because they

You know, he released... There's a unique identifier, like a VIN number inside of an airplane. It's called a hex code. And it broadcasts. And so you can track what we were looking at FlightAware earlier is all based off of that technology. ADS-B. And so...

Ultimately, if somebody really wants to figure it out, they are probably going to figure it out. And that's even if you fly net jets. It's very interesting. There are public companies. This is how far people will take steps to maintain their privacy. There are public companies that will fly their executives on net jets if they're doing M&A activity.

And they will fly two or three airplanes into the airport and have the other two dummy airplanes go somewhere else. And then the actual executives will be on the one. Like if you're leaving Chattanooga, right? If I'm leaving Chattanooga and my competitor or somebody knows that I work for Volkswagen, a bad example because they're German, right? But like some large company in Chattanooga and I'm flying to somewhere where one of my competitors is,

Like, it's not going to take a lot to be like, oh, that's weird. Like that Prater 500 just went between two cities of two companies, right? So like they may send kind of some dummy birds. But ultimately, if somebody wants to figure it out, they're going to figure it out. So as long as you can accept that, that you say, look, at some point, somebody could dig deep enough. They could find out.

One thing that a lot of people do, there's a company called TVPX that is a trust company out of Utah. And they...

They do Jeff Bezos' plane. They do Elon's plane. All of that's come out now, right? Because again, ultimately you can take steps, but sometimes you just can't help it. But they will basically own the plane in trust. And so you will own it through them. There's kind of some like legal structure that you can set up so that they can't necessarily track it back to you, the person, like the LLC, the beneficial owner information. Yeah.

But a lot of people put them in LLCs.

99.9% of people put airplanes in an LLC, special purpose entity or single purpose entity. And so that's other ways that you can protect it. But like, I mean, if somebody's sitting out at the airport and sees you get on a plane, I mean, like, you know, there's certain levels of like reasonable privacy. Another interesting kind of trend that's happening right now, Sky Harbor is a company that is

creating kind of this network of FBOs across the country that are hyper, hyper, hyper private and sensitive that have... FBO, what does that stand for? FBO stands for fixed base operator. It's the private terminal, if you will. Okay. It's like the... It...

If you go to the airport, next time you go to the airport, right? And you see like Signature or Atlantic, those are kind of the two big providers. Those are FBO providers. So they provide hangaring for private jets. And then they also provide kind of the terminal for you to walk through. The big service that they do is fuel. They make all their money on fuel. So they're making a scrape on the fuel. And, but yeah, so Sky Harbor is creating a network of

call it like luxury hangers and FBOs that have a really high emphasis on privacy, right? So they'll have garages and kind of private pickups and private drop-offs. But most FBOs, I mean, are not super private. I mean, you know, anybody can technically walk in there, right? So it's, you know, it depends on like what level of kind of

and protection that you get comfortable with. Um, but obviously if you're chartering, like unless somebody sees you get on the plane, they're not going to know otherwise. Such a, such a fascinating industry. It's a world I do not know. And so I'm really grateful for you, uh, sharing it with me and our listeners. Um, Preston, where can people learn about you? You've got a great newsletter. It's called Private Jet Insider. So folks should subscribe to that. Um,

Yeah, and it's super easy to find. It's myfirstnameandlastname.com. So, PrestonHolland.com is where that is domiciled currently. And yeah, and then I'm big on X, Preston Holland, the number six.

So that's a lot of fun. I enjoy that. I'm on LinkedIn. I'm way more tame. If you want kind of the spicy takes, X is where you go. If you want like corporate Preston, then find me on LinkedIn. And yeah. And if you subscribe to my newsletter, it comes to my inbox. So yeah.

If you get an email from that and you reply, it will come directly to me. So I'm pretty... I mean, for the most part, I'm pretty accessible and pretty open. I'm an open book when it comes to giving information. I'm a big believer in the rising tide raises all ships. I'm a big believer in kind of that mentality. So however I can be useful...

uh i'm not gonna you know uh nickel and dime you and see you and stuff i mean i i give away 90 of it so awesome private jet insider is the newsletter preston holland six on twitter x and prestonholland.com is where folks can sign up so thanks for doing this preston awesome thanks so much for having me i appreciate this is fun

And there you have it for today's episode between John and Preston. If you enjoyed today's episode, be sure you hit that subscribe button wherever you're listening to today's show. And if you want to help support this podcast, I'd encourage you leave a rating and review either on the podcast platform you're listening to or over on YouTube at Built to Sell. For show notes, including links to everything referenced in today's podcast with Preston, you can visit his episode page, which you're going to be able to find over at BuiltToSell.com.

Special thanks to Dennis Lebetagler for handling today's audio engineering. And thank you to our community of certified value builders who help us bring our message to you. Our advisors are experts in helping you build the value of your company. To get in touch with an advisor or learn how to become one yourself, head over to valuebuilder.com. I'm Colin Morgan, and I look forward to talking again next week.