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We already pre-sold $27 million. You'd have to do a lot of sponsored content [laughs] to get there. That's a lot of magazine ads and a lot of sponsored content.

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Um [laughs] You're not gonna webinar your way to the 27 million.

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[laughs] [upbeat music] Welcome to The Rebooted Show. I'm Brian Morrissey.

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One of the things I love doing about these shows, I love having B2B publications on.

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Particularly I love B2B because, like, they're always about, like, niches and communities, and you get to learn about different communities, 'cause, you know, you're not in the community, but lots of different people are.

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So I'm very happy to be joined this week by Preston Holland. Preston is the COO of FLYING Magazine. Preston, thanks for joining us.

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And so Craig Fuller, who I do want on the podcast, the CEO of FreightWaves, bought FLYING like a year or so ago, and I think it's really interesting what you guys are doing to FLYING, and it's got a very long history as a magazine, but just give us the sort of backstory on FLYING.

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Yeah, absolutely. So FLYING started in 1927. It started as Popular Aviation, so if you are familiar with Popular Science and Popular brands, they're all Ziff Davis titles.

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They all kind of have run through the Ziff Davis world. So FLYING started in 1927, right after flight started, and so it became the authoritative voice in aviation.

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Uh, has changed through a few different publisher hands. So about a year ago, Craig hit me up out of the blue and was like, "Hey, I'm gonna go buy FLYING Magazine. Do you wanna come help me figure it out?"

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And I was like, "Why are you buying a magazine in 2021? Like, aren't magazines dead?" Like it's... You know. He said, "It- it'll be fine. We'll figure it out." I was like, "Okay. Well, sounds like fun."

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So joined the group.

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We officially made the announcement July of 2021 and have spent about the last year and a couple months turning it around and really making a lot of investments in it and trying to make it something that, you know, the core audience appreciates that had, it had been in its heyday, and, you know, try and welcome more people into aviation.

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What was the opportunity you saw? Like, so first of all, who is FLYING for? I mean, originally I was like, "Oh, like, this is for what? People who own private jets. Like, that's, like, not that many people."

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But, uh, there's an entire community of private aviation. There's people, they, they usually have other people flying their planes and they're super rich. But this is, like, a hobbyist target, right? Yeah, exactly.

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I mean, think there are mega yachts where you have a captain who drives you on your boat, and then you have, "I take out my little flats fishing boat and fish on the weekends," or maybe I've got a pontoon boat, right?

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Aviation has a lot of that side of the market. Not a lot of people are exposed to it on a daily basis, but there is actually more general aviation planes in the air than there are commercial planes, right?

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So you think general aviation is anything from a kit built, which would be I built this in my garage and I bought a parts kit off the internet. Oh, Jesus. Hell no. [laughs] Oh, my God. I'm not into it.

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I put together a bike and I was, like, nervous. Yeah, and then take it into the air. So, [laughs] so there's, that's- Nope... a- and then you even have ultralight, which technically falls under general aviation.

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Yeah, I see them all the time along the beach here, and those look super cool, but also, like, I, I'm a Philadelphia sports fan, and, like, one of the Philadelphia Philly got killed flying one of those things.

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Those look super dangerous. I gotta say, I'm not interested in either. But it is pretty neat. Like, so how many people are in this world of, like, piloting their own aircraft of, of some kind?

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So the FAA database is about 200,000, give or take, that has private pilots, and that's private pilots all the way up through commercial airliners, so that's a large pilot population.

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General aviation probably, there's a couple different organizations that'll try to put a number on it, but it's hard because not everybody registers, not everybody keeps their stuff current, everything like that.

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But you're probably looking somewhere in the 100,000 range of people who either fly somebody else's small plane or they might own their own or they may own up to...

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I, I met one guy who has, like, 18 different planes that he flies out of his big, giant garage hangar. So there's a wide variety. And also, it's upper middle class and up, right?

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'Cause it's to get into, uh, $300,000 to get into a brand-new experimental aircraft.

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[gentle music] The Velocity V-Twin was designed to provide a safe and efficient transportation aircraft, especially for those who fly at night, over mountains, over large bodies of water, serious IFR, and those who just want the redundancy of a second engine to get them home or to an airport in the event of an engine failure.

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Cirrus SR22T, which is kind of Tesla of the skies, if you will. You're looking at about a million, a million one.

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[gentle music] Now, in 2022, the SR-series G6 reaches a new level of refinement, performance, and convenience. So that's kind of the single engine piston range, and then from there you can go up into turbo props or jets.

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The only difference is with turbo prop airplanes, you have a propeller on the outside of the engine bay, whereas in a jet you have the fan blade on the inside of the engine.

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5, 10 million, and then, then you start talking about, like, the Gulf Streams. [upbeat music] The spacious cabin boasts three flexible living areas, including an extra large baggage area that is accessible in flight.

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And then you're looking at 30, 40, 50 million. Right. So what's the low end? Like, what's the entry level- You could-... in case I get over my fears? Yeah, you could get into an old, a 1970s, 1980s.

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Y- before COVID, you could get into one for, like, 60 or 70,000. Wait, a really old plane?Yeah, like a really old- Okay. No, no... still airworthy. That's also a no. [laughs] Yeah.

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If, if it has the ashtrays on it, I, I'm not interested. The, the spinner dials instead of anything that's digital. [laughs] So I mean, if you're looking for a glass cockpit, that's kind of what...

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You know, glass cockpit is the way that you say it's got current electronics in it. Yeah. Doesn't have dials and things. That would make me feel better, I gotta be honest with you, Preston. Yeah.

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Something digitized would, would... is definitely, like, base level expectation. [laughs] Are you a pilot? So I- I see- That was part of my condition with joining- [laughs]... was I had to...

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I said, "I have to learn how to fly." So I have started my private pilot training. Okay. So I have my... got my FAA medical and have started flying. It's, it's a lot of fun. I mean, there's so much to understand.

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There's a bunch of rules and regs and all that kind of stuff. Yeah.

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So it's a lot, but there's a bunch of great training and- But going into this, though, is more of a commitment than getting a boat for the most part, right?

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I mean, here in Miami, like, people don't have any licenses, they're in the boat.

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There's an entire genre of Instagram video of people who don't understand how to get a boat out of the water on the boat ramp, and so their car goes into the water.

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But I think Miami is special in, in that way and many other ways. But if you're gonna learn to fly, like, it's much more of a commitment. And so I would guess that you're gonna have a smaller group.

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But, like, the people are gonna be super into it. I mean, they've committed to this. Yeah. It's a, it's like a rabid fan base. I mean, I- Yeah... really, there's really very little to compare it to.

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I mean, mountain biking, you could probably draw some parallels. The guys who are- Oh... really into mountain biking are really into mountain biking. It's, like, all they do.

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It's all their vacations are Mountain Bike Central. It's, you know, they usually marry somebody in mountain biking who they want to do it with. They get their kids doing it. It's, you know... Yeah.

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That would be as close of a parallel, but you can still, you know, pick up a mountain bike and just try driving it. You can't just pick up a plane and attempt to fly it, right? So it's a little different.

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You're looking at about $15,000 to get your private pilot certificate, when you talk about training- Okay...

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some of the gear that you need, the instructor time, things like that, to get checked off to be able to fly yourself somewhere.

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And then, so it takes between 40 and 50 hours, kinda depending on your propensity for education and ground training and all of that, but you're looking at about 15 grand to get into it.

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And then you don't have to own the plane. There are options where you can rent planes, or you could be part of, like, uh, the boat clubs. Yeah. You could be in, like, a plane club, right?

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There's, there's those that exist. So 15 grand, it's about similar to getting your motorcycle license, I mean, and buying kind of an entry level motorcycle, kinda similar. There's...

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I know people who spend way more than $15,000 on golf in a year. So it's more approachable than, than most people think. Okay. So when you guys acquired this, like, what was the business?

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I assume it was, was it very print focused? Like, explain what was the state of the business. Yeah. So revenue mix-wise, print was the primary driver of revenue, right?

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So in tr- traditional print magazines, you've got this rate base of however many hundred thousand people that you reach, and that is some calculation of newsstand. There's a pass through calculation.

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There's controlled circulation. There's paid circulation. There's agent sold subscriptions, right? So you have this rate base. You're selling advertisement against that.

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And then there is a subscription element to it, right, where you have reader revenue.

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So 80/20 mix when you talk about print versus digital, when you really take into account all of that reader revenue, advertising revenue, et cetera. Um, and so we took it over.

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Our original intention was to kill the print product, right? That's kind of the- Yeah... that's the model these days, is go buy a magazine with a lot of photos- Although that's sh-... shoulder print...

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but to be fair, that is changing, I think. You know, I mean, you look at, like, you know, Dotdash took over most of the Meredith publications and, you know, they didn't kill a lot of them.

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So think that that is changing somewhat. Like, I think a lot of people are, are seeing value of print. I wanna get, like, uh, like, I just think it does a different job for different people. But what do you...

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So what were... I don't know, where did the, the print fit within the sort of model, um, that you guys were hashing out? Yeah. So originally, we were gonna kill it.

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A lot of lifetime subscribers and advertising partners said print moves the needle for us. If you think about being in an airplane, if you don't have Wi-Fi, what are you gonna do if you're flying for four hours?

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And so print magazine- Pay attention... fits perfectly. I don't know, something could go wrong. I'm not gonna be reading a magazine while I'm flying, am I? You've got autopilot. So- [laughs]...

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ATC says, "Go this way, go this fast," and you say, "Okay." And then you hit the button, and then it's like- Then you just look around...

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it's like you, you look around, and then you get bored, and so you, you open up your, your flying magazine. Yeah, exactly. So- [laughs] So, you know, we said, "Okay. Well, we're gonna keep the print.

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If we're gonna keep the print, we wanna do..." W- we didn't wanna keep it in its current state. You think about these print magazines, they take on th- essentially unpaid subscribers, right? Yeah. So if you have...

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If you take on a subscription from an agent, they might pay you $2 on a $12 subscription. As the publisher, you still have to print, fulfill, and execute customer service on that subscription.

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So if you're printing 12 magazines a year, and let's say it costs you a dollar 25 an issue times 12, you're already underneath that individual subscriber, right? So there's a lot of agent sold subscriptions, and I...

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That's, that's print magazines everywhere. You know, once you start really digging into it, there's a lot of subscribers that were taken on the file in order to increase kind of numbers and, um- Oh, yeah...

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yeah, it's, it's just big numbers game, right? I mean... Yeah. I mean, people talk about, like, fraud in digital, but I mean, my God, like in the magazines, it was impossible to track anything.

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I remember Jane Pratt, like, from, from Sassy one time saying, [laughs] she was like, "Oh yeah, we counted every single girl at the sorority house read, read Sassy."

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Like, if there was one subscription that went to a sorority house, every girl was reading it, at least from what we were saying. So yeah, I mean, print was always like that.

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But, like, so what, what was the sort of diversification strategy? Obviously, moving more into digital be- would be obvious, but, you know, I'm interested.

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I don't wanna get obviously to the fly-in communities, but, you know, particularly in this area, there seems to be-A lot of different ways you can make money versus just advertising. Yeah.

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So aviation is brand new to the affiliate space, so y- your options are really Amazon, and there's a few ground schools that'll do automated affiliate.

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So we're trying to teach the industry on it, you know, and it- it's definitely growing in our revenue mix.

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It went from being fractions of a percent to it's kinda creeping into the one, 2% range, and we're really trying to expand that because the SEO game.

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And we've got great brand authority, great domain authority, so the Google algorithm likes us, and aviation's not super competitive because there's not 1,000 aviation credit cards that you could do.

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So The Points Guy doesn't necessarily write a bunch of aviation content, so you're not necessarily competing against the people who are really good at SEO.

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So we're trying to teach aviation about that and help them understand, hey, you can pay us on success, and we can help- Yeah... drive the successful transaction. Um- So like, what kinda transactions?

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What kind of products w- would you guys focus on? Headsets a great example. Planes, hard, hard to get an affiliate on a plane. [laughs] But if you did, it'd be a very- Yeah... large affiliate.

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1% of a million dollar plane. That'd be great. If you did the math. But, you know, for us, okay, a, a headset, right? You have a two-seat aircraft. There's a pilot and a co-pilot. They both use headsets.

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Bose makes one, the Bose A20. It retails right now for 1,095, right? So that's a- Yeah... $2,200 order value, right? So Amazon sells those, so we link to Amazon. Amazon gives us their percentage cut.

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We make a recommendation, and they say, "Okay, cool." That's one example. There's so many different pieces in the cockpit. You've got your flight bag. You've got training material. You've got avionics panel upgrades.

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Those can range from a $800 upgrade that you still have to get somebody to do install to a full redo. You know, you're looking at 30 or $40,000. And so you're really trying to help inform that buying decision.

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"Hey, you should buy this new piece of electronic to put into your aircraft." We're gonna make, help make the suggestion, pays an affiliate if somebody decides to take that action. Yeah. I'd want a flight suit.

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If I do get a plane, I'm gonna have a flight suit. That's what I've decided. [laughs] Top Gun Brian. [laughs] Exactly, with the little name. You know, Maverick and... So a little bit of affiliate.

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Usually with, although this isn't, like, B2B, but, like, events come in, live comes in. Like, if you have a community, usually people within the community want to connect with others in that community.

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If you're in B2B, it's to do business or to, to get, strategize all sorts of different things, but, you know, within niche lifestyle communities, there's always opportunities when you can sit in the middle of it and bring people together.

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How are you guys thinking about that? So the largest airshow in the world is in Oshkosh, Wisconsin. It's the last week of July.

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600,000 people come through the turnstiles for exactly that, because it is a huge aviation show. Yeah. It is airplanes as far as you can see.

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If you have any interest in airplanes, you have to get to EAA AirVenture in Oshkosh because it is, pictures don't do it justice. It is breathtaking how many airplanes you have in this one location for a week.

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The, uh, the airport is busier than O'Hare for that week. [laughs] It's busier than Atlanta for that week. It might even be busier than the two of them combined.

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You have aircraft landing from 6:00 in the morning until 8:00 at night- Yeah... every 30 seconds. Um- Yeah... you've got planes coming in and landing at the same time on the airport. It's, it's really insane.

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So this community loves getting together. There's, you know, breakfast, pancake breakfasts that happen all across the country every Saturday morning.

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You know, there's one that meets about 30 minutes from my house that I've been to a couple times. Um, they get together at their hangar because they are, they're all at the airport.

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You've got 60 hangars next to each other. Everybody likes airplanes. Everybody wants to look at each other's airplanes, so they get together and have a cookout or, you know, have some sort of a meeting or something.

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So events is definitely something that we're thinking about. What we want to do is we want to create, um, something that's different than what they can experience, uh, just at their hangar, right?

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You don't wanna compete against those longtime friendships. Um, you really want to create something that's unique and special.

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And so how do we partner with other even media brands that have adjacent lifestyle activities?

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How do we bring that all together, introduce people that may not have known each other but have the same level of interest from different parts of the country, right?

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Because we're not necessarily as constrained by geography because everybody's likely going to fly themselves there anyways. So stick a pin in the map in the southeast and you can get people there. Yeah.

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So but geographically, is this, like, more, I don't know, is the pr- is, is it more like, I don't wanna say rural, but it's like rural suburban.

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Like, you know, it's not in like, the most densely, like, urban areas where people are, are flying planes. I don't know anyone who flies a plane. Um. You, you would be surprised.

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I mean, our- [laughs] Maybe they don't tell me... from a, yeah, from a sub- from a subscription standpoint, Florida, Texas, California- Oh, man... New York, right? Those are the big states.

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Dallas, Dallas-Fort Worth has a ton of private aviation. Okay. Um, that's, you know, small airplanes, guys flying in the backcountry.

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But like south, like that sort of like band of like the Sun Belt, like, and sort of things. And I'm sure in California it's less, it's, it's, you know, California's a massive state, so. Yeah, exactly.

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I mean, there are people everywhere that fly. You know, the reason people probably haven't told you is you probably haven't asked them. But I would- That's true. [laughs]...

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bet that, I would bet most people at least have one degree of separation from somebody who either owns a private plane or rents one and flies it for fun on the weekends. I gotta find, I gotta find the person.

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I know one guy. I, like, one, one person from, uh, ad tech. They, uh, I remember he sold his company, and then, like, he flew his plane to, like, the next event. Um, it was, like, a big plane.

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I remember talking to the marketing director who didn't want, like, to go on with him. But, like, um. There's this crossover in payments too, like fintech. There's a lot of fintech guys into private aviation. Really?

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Um, like a surprising amount. I think it probably, you know, if you indexed it, it probably over indexes. Yeah. I'm not sure what the parallel is, but if- Yeah...

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think of a big fintech company andA lot of the CEOs and founders- Yeah... fly private aircraft. Small, small planes. Um, so I wanna get into the fly-in community, but first just on the print thing.

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Um, uh, y- the, the ad demand was there, the audience demand was there, um, so you decided to keep print around. Um, I've seen it.

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You, you guys obviously invested money in it, like, you know, it looks nice, um, probably better paper stock. People always... Um, i- is that... Ex- explain where that fits within the model.

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Yeah, so print for us, [clears throat] because we have this, um,

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uh, the idea of media companies marrying it with some other monetization strategy allows for you to make some decisions on the media side that you wouldn't necessarily make if you were trying to make all your contribution on the media side, right?

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So we said, "Okay, we need to figure out another way to monetize this audience." They have a high affinity for print, so we subscribed.

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From July through January, I think I subscribed to over 70 magazines, and Craig did the same. I mean, I have... My desk in my house is stacked both sides up to my eyeballs because I keep getting these magazines.

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I'm like, "I don't actually, like, care about this horse magazine- He just got in-... but I subscribed"... he just gone to New York, gone to like McNally Jackson. He get every magazine known to... [laughs] Yeah, exactly.

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So we subscribed to Golfers Journal. It was one of the... Golfers Journal and Surface Journal was just one that we subscribed to. Oh, yeah. We said, "Okay, this is beautiful," right? It is, it is elegant.

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It is high quality. It is, um, art-forward. It is beautiful photography. It is compelling stories. Um, this is kind of the model that we wanna go for.

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Instead of saying, "Okay, we're just gonna keep the really low-quality print" And your plop factor, if anybody's an old print person, plop factor is like this- Ooh...

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term when you throw it on a table, how loud does it plop? Oh, God. Um, we might have the loudest plop factor in magazine turnout. There was the tie test. I remember being told about the tie test.

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It has to be like thicker than your, than the tie, 'cause otherwise it won't be taken seriously. Yeah. I- Wow... I don't know anybody who wears ties anymore, so I'm not sure how you would- I don't know.

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The whole thing was just, like, very... And I was like, "Ugh, let's just stick to newsletters and websites and stuff." Um, but no- Right...

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we actually, actually started a magazine 'cause it just does a different job, right?

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I mean, it, it elevates a brand, um, and when you don't have to rely on it as, like, a main revenue driver, um, it becomes, you know, an actually really interesting, um, piece of the brand.

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I just think the job it does is more on the brand level than on the, like, monetization level. Yeah. I think, you know, if you think about different mediums, right? You've got... Newsletter's just a medium.

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Podcast is just a medium. Print is- Yeah... just a medium. A website is just a medium. It's all just a medium to communicate some sort of a message. Mm-hmm.

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And if you have the authoritative voice in your community, you can bring a message to them however, wherever they want to actually consume it. For us, print moves the needle for a lot of our subscribers.

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Um, for fintech, print probably doesn't move the needle, but a newsletter does, right? It's why newsletters do really well in that sector.

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Um, so for us, as we think about the magazine, we said, "Okay, we're gonna go really high-end. We're gonna go really high quality." You know, we doubled the production cost, um, that was associated with it.

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And what we did there with the upgrade, on the other end we said, "We're not gonna take on these subscribers that only pay us $2 for this subscription." Mm. Because

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they probably are not actually our core audience anyways. If you're spending $15,000 to get your private pilot's license and you're not willing to fork over 30 bucks for a magazine subscription- Yeah...

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are you actually the target audience of those advertisers? No. Are you actually somebody who we want to influence in our community? No. You're just a number at that point that you're trying- Yeah...

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to up the rate base, and you say, "We're a pilot magazine. We have X amount of subscribers." And the advertiser goes, "Oh, cool. They have X amount of pilot subscribers." But, like, that's not how it works. Yeah. Right?

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Well, that's why I would like when the tech people would go to the media people early in the internet and be like, "Oh, we're gonna be able to, like, separate audiences and separate the wheat from the chaff."

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And, like, [laughs] the media people were like, "Wait a second. Our business model is made in mixing and turning out the lights and mixing the wheat and the chaff together and selling it all as wheat."

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Um, because that's, you know, where the, obviously, the money was made. Um, but, like, uh, yeah. So e- explain how you ended up getting into real estate with this 'cause this is like...

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It's a great story, I feel like, uh, and I wanna get into it. Yeah. So we were seeking, as soon as we ma- as soon as we finished the transaction, we were looking for that other monetization model.

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Craig talks a lot about with FreightWaves how the media business creates a negative customer acquisition cost for his software business, right? So- Right...

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get paid for advertising, you get the client, and you essentially have cash flow that funds your software, right? So, um, we're looking for that opportunity. There's a lot of software in aviation.

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We said ads, you know, would take a while to try and build something to compete with those. Um, so we're kinda looking around. We started experimenting.

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So it all started with we were looking for a physical media center on an airport. So we called up all the airports in our region and said, "Hey, we wanna open up a studio on your airport in a hangar."

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And they all laughed at us and said, "You're looking at a five-year wait list at the least, and even then we're not really sure if we can get you as much space as you want." Mm. And so we said, "Okay.

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Well, there's clearly no hangar space in our area. Let's start exploring, and because we're a trusted media brand, we can ask the question and say, 'Hey, do you have hangar space?'" Everybody's saying no. I mean,

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you cannot find it. You're looking at two years plus just to get your airplane into a garage, right, a big garage. So we said, "Okay.

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Well, if we're gonna do this, we might have to actually build our own airportWhat would it mean if we're gonna build our own airport? Well, we should build an air park.

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We understood that there was these air parks all across the country that people actually live with their planes, and you taxi out to the taxiway and take off and go wherever you want to, right?

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So instead of, like, living on the lake and you just walk out to your boat, the same way for airplane people, you walk into your hangar, you open it up, you get in your plane, and you take off from your house.

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You know, you're no, no more than a few steps away from your airplane. So we started writing content around air parks, and in digital, you get direct feedback. These stories are popping.

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We're writing, you know, reviews and, uh, story pieces on people who live at air parks and different profiles on air parks, and all of a sudden this content is just popping.

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You know, every time it's like you watch Google Analytics, like, it just pops up. Said, "Okay, well, there's something here. There's a, there's an affinity to living with your airplane here.

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Um, so let's build an air park." Well, if we're gonna build an air park, we've gotta convince our wives to come live on an air park, 'cause as airplane people, you're like, "Heck yeah. I wanna live in my plane.

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I don't really care where." [laughs] But not a lot of wives are like, "Oh yeah, that sounds great. Let's go live at the airport." So- [laughs]...

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uh, we i- it kind of evolved into this thing where it's like, okay, we've gotta convince our wives that this is a good idea.

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So our wives wanna be at the spa, and they wanna have a local grocery store, and they're gonna wanna have amenities on site. They're gonna wanna have a restaurant.

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And so it evolved into this community, and so we, we created this concept. And really it was by, you know, we'd release an article, and if it resonated, we'd say, "Okay, cool.

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There's something about this that resonates." So something about being in nature that resonates, so let's take that as an input and- Yeah...

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there's something about being in a tax-friendly state because it leans towards high net worth individuals, so Tennessee makes a lot of sense. There's not a lot of tax here.

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So it all kind of evolved, put an offer in on 1,600 acres, um, and ran an ad in our own magazine that said, "Hey, we're building an air park. You should come join."

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We said, okay, this is, uh, this is probably gonna take a little while to catch on, you know, write in perform- 10, 15-year performas. They look really good.

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Um, we said, okay, if we can sell, you know, a couple of lots in the first year, that's gonna be incredible. Um, we sent out the magazine.

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We instantly had 300 inbound requests for our offering, um, and we started taking deposits, I mean, two weeks after we announced it. Um, real- So wh- wh- e- explain, like, so you're gonna, you're building homes.

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Explain how this works, like, for those of us who just heard of air parks. Okay, so we bought 1,600 acres. Yeah. We're gonna build the runway, the roads, the infrastructure, the FBO, which is the fixed base operator.

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It's like, um, I don't... There's, it's really hard to explain. It's kind of where you walk in and out of. It's where you get your gas. It's, uh, kind of the port of entry, if you will. The grocery store, a gas station.

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We build the infrastructure, and then we lay out the plot lines, and then people buy the dirt, and they build the house. Right, so we're construction- Oh, they, so build, they build their own homes. Yeah, exactly. Okay.

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We're not, we're not s- originally we thought we were gonna spec build. Yeah. Um, and we thought that our runway only needed to be 3,000 feet.

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We then started having people who owned small jets and turboprops that needed more runway, and they said, "I don't want you to build my house. I wanna build...

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I'm gonna fly my builder in from Colorado, and I'm gonna build my own house." Okay. So that is a different equation than spec building, right? So then we just- Yeah...

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started, we just laid the dirt, laid the runway for them, and then said, "Hey, come build your house here.

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Come, you know, retirement house," or, you know, if you're a pilot for an airline, it's, you know, say you work for Delta, it's a s- short hop down to fly your flight.

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You know, airline pilots can make, you know, four or five hundred thousand dollars a year, so it's a, you know, upper middle class, you know, lower upper class type individual.

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So yeah, and we just started advertising through our own channels, and we've had 1,200 people submit requests, uh, to, um, actually come- Yeah...

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buy property at the air park, and we've taken deposits that represents $27 million worth of real estate sales. Holy shit. Um, di- uh, so did you guys do... I mean, 'cause this is a lot of capital.

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I gotta say, like, it's more capital than a podcast. Did, did you guys do this all, like, on your own? Or y- you have co- other investors in this, right? Yeah, so we used, we used the magazine.

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I mean, think about people who own private planes- Yeah...

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tend to have LP money that they put into funds, and so we're actually in a qualified opportunity zone, so there's a lot of tax deferral, uh, pieces for investors.

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So we, we raised a fund, um, and then used, uh, bank financing for the rest of it and kind of used those two things together and, and had a bit of a mix and, you know, using the magazine as our source of advertising.

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We're getting paid advertising dollars, but we're advertising our own development. Yeah. Right? Okay. So, um,

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where does this fit, like, in, in the, you know, you mentioned the pro forma, like, of, like, the flying pro forma, like, in, like, five years? Like, I mean, is this...

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'Cause, like, a lot of, like, a lot of companies, like, media is, is the front end. It's not the main business.

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Like in B2B, most of the B2B companies in, like, in the media and marketing area, their events are the majority of their revenue. Um, so you could say they're events companies really more than, than media companies.

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But d- do you see this to be, you know, this to be the majority of the business, like, in five years? Yeah. I mean, if you look at,

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if you look at real estate sales and the spread that you can get on building a ground-up development-The media asset, uh, when you really boil it all the way down, is a very small fraction of the revenue, very small fraction of the cost base, and a very small, you know, capital investment on the front end that you can then pull through this monetization effort on the back end and sell real estate, right?

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So if you sell... You know, we've already pre-sold $27 million of, uh, real estate. [laughs] You'd have to do a lot of sponsored content to, to get there.

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[laughs] That's a lot of magazine ads and a lot of sponsored content. Um- You're not gonna webinar your way to the 27 million. [laughs] No, not at all.

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And so it, it creates this really unique, um, the media business creates the top of funnel. The other thing you get with the media business is we can write about air parks and keep it at the front of somebody's mind.

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Are they gonna buy at our air park? We hope so. But maybe they buy at another air park, but we're pushing the narrative forward, "Hey, you should live with your plane. If you own an airplane, you should do this," right?

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So you have this cultural liquidity that you get with a media business- Yeah... that you can then use to pull through to your real estate business, right? And- So how many air parks are there in the United States?

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There are, I should know this number off the top of my head. I believe the last time I looked there was about 100. Okay. There's a lot. Relatively speaking, right? Yeah.

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I had never heard of an air park when I started working for FLYIN'- Okay, tell me. I, I don't feel bad now... and then I started visiting them. [laughs] Yeah, no. I, I honestly had no idea that this was even a concept.

194
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I knew about living on the lake. I have lots of friends that have lake houses. Yeah. But I had no friends that had plane houses.

195
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Um- Well, this is unusual in that, like, I know, like I've seen the, the photos and it looks, it looks lovely, and I, I know that part of Tennessee is, is beautiful, and all of Tennessee is beautiful.

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But like, usually, like you have a place where, like, you know, this is like you're able to... Because you have a plane like right there, the idea is you're going to be going other places, right?

197
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So it's a little bit unusual in that.

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And I, that actually gives a lot of leverage because, like, if you're, if you decided to buy 1,600 acres in Lake, let's say Lake Tahoe, where people like to go, it'd be, it'd be a different business.

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[laughs] Yeah, exactly. I mean, the fields is, we, we like to say it's in the middle of everywhere. You can be in Charlotte, Atlanta, Chicago, New York, Miami, the Keys, um, Nashville, Birmingham, uh, New Orleans.

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You can be in a lot of major cities.

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If you own an aircraft, depending on the speed of your aircraft, you can be there in one to four hours, as opposed to if you're gonna drive from Chattanooga to New York City, it's like 13 hours and you've gotta fight traffic through DC and all the New England states.

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Yeah. You know, it's a totally different equation. And these people are, you know, running work from anywhere businesses a lot of the times. They might be franchisors that have franchises all across- Yeah...

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the southeast. Car dealers have a huge propensity for- Yes... aircraft ownership. So we've got- I always think of like air- airplane owners are in like northeastern cities. It's like the real rich people.

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Like, this is my story. It's like the real rich people own like car dealerships or these things, like, and, and they live i- in, not in like necessarily like New York or San Francisco or Miami and stuff like this.

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There's like... And I always see like people, like, get surprised at the, the true people who, who are very rich, they're like, you know, the people who, who, they're the chamber of commerce people at the end of the day.

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They own businesses. Right. Exactly. Um- The guys who own a bunch of McDonald's, they're the ones- Exactly... that you gotta look out for. [laughs] Totally.

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I mean, the guy, I'm, uh, leaving Miami, but like the guy who owns the, the Dolphins, I believe he started with owning a bunch of maybe laundromats or something.

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But this is like, I, what I like about this model is if you get the playbook down, I mean, you know, you just hook up with like BlackRock or something and buy up all the car parks and rebrand them into FLYIN', and then you have like a front of a, you know, you have the top of the funnel with the media property.

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And, you know, i- if you have a profitable model, it, it makes a ton of sense, right? Yeah, exactly. I mean, you know,

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I am, a- as I looked at the media landscape, you, you think about the idea of content to commerce, and it's exhausting how often you hear people talk about content to commerce if you listen to a lot of media or read a lot of media news.

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Mm-hmm. It's like, uh, it's, it's a very buzzy word. But if you really break it down, what it is is it's cultural liquidity that translates into a real life transaction, right?

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So, um, you think about, uh, Hodinkee, right? You got content, but I'm gonna buy a watch, right? So it's, it's this content concept, but I'm gonna- Yeah... actually get a physical watch, right?

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I'm gonna read a newsletter, and I might buy a piece of software. Yeah, that's content to commerce. But I think the really interesting trend is when you can take that

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cultural identity and turn it into something, whether it's real estate or it's buying a bicycle or it's buying a watch or something like that, right?

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Where, you know, the e-commerce guys are not very good at media, right? They're really good at buying Facebook ads, but they're not really good at influencing the narrative.

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Media companies are really good at influencing, this is what you should do. You use that and you monetize on the back end.

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Now you have to have editorial integrity and not just say, "Buy my air park, buy my air park, buy my air park."

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[laughs] But you say, "You should live in an air park, you should live in an air park, you should live in an air park. Oh, by the way, we have the solution for this problem that we've made you aware that you had." Yeah.

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Are there other, like, adjacent areas that you guys see similar dynamics, or is this like a big enough, and it obviously is a big opportunity that, like, you're like, "This is, like, we need to go, like, 100% in on this"?

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Yeah. I, I think that there is a lot of opportunities.

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I think part of the difficult part of the playbook is identifying the, uh, cultural core group that associates with some piece of lifestyle.You are not probably gonna go live at a residential community for most of, like, better homes and gardens or those types of properties, right?

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Yes, we all love gardening. You can do events, but you're not gonna live with a bunch of gardeners, right? Because it's not as much of an identity piece, right?

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So it's identifying what are those activities that have that identity piece, then go- Mm...

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find who is the person who has, or the, who is the media company who has the most influence over that group of people, and then how do you monetize the back end, right?

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That's the, the challenging part of making this model scalable and work is, is being able to pinpoint those, identify them, um, and then create the offering that they, you know, that they want. Yeah.

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And I think it totally plays into a, a former guest on the show, uh, Joe Marchese, was talking about, like, you know, media's great for getting attention, but, like, historically, the money has been made in other ways.

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You wanna have the cost of the content and production ideally paying for itself, the regular stuff, advertising and subscription and commerce and whatnot. But, you know,

228
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it, it is a great way to have attention, but it's like you need to, like, connect it to a different business a lot of times. Yeah, exactly. I mean, you've...

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I was talking to Adam about this, Adam Ryan, the other day about this when I was on his podcast. But the, there's this multiple on media company PNLs, right?

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You look at, like, i- in traditional companies, you look at this goodwill multiple, right? So it's how mu- It's, it's some sort of mixture of, like, how much brand does it have, right?

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That Apple goodwill multiplier is huge. It's why their stock price is so high. Yeah.

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There's this goodwill multiplier, the media multiplier, but oftentimes when you buy these assets, they don't get valued with any of that goodwill multiplication because there's no good monetization opportunity on the back end.

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There's no, quote-unquote, "good business" on the backside. Mm. There's just, you know, "I'm gonna sell you an ad or a subscription or branded content, and we're gonna try and make the economics work on the back end."

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But we don't have this other monetization opportunity on the back.

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I think media companies are highly undervalued when you at, when you look at their actual offering price, as long as you can figure out on the back end, "How am I gonna monetize this in some way that isn't advertisement, subscription, traditional media monetization models?"

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What are some areas that you think, like, this applies to? I mean, obviously we're in the lifestyle space. I think the lifestyle space is a no-brainer.

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Um, I think, uh, capital raising and, uh, equity environments, you look at, um, what Pomp has done. You look at, um, what Packy's done over at Not Boring- Yeah... right?

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Where it's, "Look, I'm gonna get your attention, and I'm gonna break even with my advertising, but also, I'm gonna get all this carry, right, on the back end." Yeah. It's free customer acquisition.

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I think it makes a lot of sense in those. I think any business that you have, um, high margins in the back end, um, and you have a need for cultural awareness I think marry very well with purchasing a media asset.

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I think e-commerce companies not looking at, uh, media assets to acquire, I think that's, it, it's a large capital-intensive purchase in the front end, but what you're buying and marrying those two things together, you're achieving the e-commerce margins that you get on the back end.

241
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But you're getting this cultural liquidity on the front end. But you can actually pick them up for not what that multiple is for you together, right? So you can bolt those two things together.

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You look at Penn buying Barstool, and- Mm... you know, will it suss out in the long term? Not sure.

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But in the short term, the stock price reflected that media cultural phenomena that allowed for low customer acquisition cost, online gambling being a very high margin business.

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Marrying those two things together, the stock price said, "Yes, we see this. We understand that this is valuable. Now it's come back down to earth."

245
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So who are some, like, who are some media companies you, that you look at and you're like, "They've got an interesting model going on"? So I mentioned Hodinkee earlier.

246
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I think that's a very interesting model because watches, the economics on a watch are pretty solid from what I've read, right? You've got- Yeah.

247
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I mean, yes, there's a lot of man-hours that go into it, but you're, you're influencing this cultural liquidity. I think that's really interesting what they're doing over there.

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You know, the, taking the B2B, um, I, I think taking a lot of lessons from B2B and understanding that top of the funnel piece, right? So you look at, you know, even Industry Dive, right? Mm.

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Great executors, top of the funnel, got bought by Informa to act as a top of the funnel for a lot of their events.

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I, I think that that's really interesting, and if you can execute on the content side, um, and then monetize on the backside, you know, I think, think that's super interesting. Yeah.

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It is interesting that, the, there's a lot of, like, companies that are really good at, like, the, the margin and the monetization stuff, but they don't have the, like, what do you, you call it cultural liquidity and stuff.

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And then you have, like, you know, media companies that are really good at the, the cultural bit and the getting attention and, and just being ideally very audience-focused and stuff, but usually they suck at the, like, you know, making real money part.

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[laughs] Yeah, exactly. All right, let's leave it there. Preston, I really wanna thank you for taking the time. It's a fascinating space, and I'm still not convinced I'm gonna be a pilot, but maybe one day. Yeah.

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No, I, I think everybody should go take a discovery flight. [laughs] It costs about 150 bucks. You can go up in a small airplane. They'll take you around. They might let you fly it for a little bit. Yeah.

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See if you like it. It's a really fun experience- Yeah... and it unlocks a lot of opportunities for you to go to places you probably never would've gone before. Yeah.

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And at the very least, you get a good Instagram out of it, right? Exactly. [laughs] All right, Preston. Thank you so much. Thanks, Brian. Thank you for listening this week. We will be back next week with a new episode.

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The Rebooting show is produced by Podhelpus. Podcasts are a great way to expand your client base.

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