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Preston Holland – Transforming Flying Magazine

Preston is the COO of FLYING Magazine, which was purchased in July 2021 by Craig Fuller and has been going through a broad transformation to a modern media business.

Episode Description

My guest on this episode is Preston Holland. Preston is the COO of FLYING Magazine, which was purchased in July 2021 by Craig Fuller and has been going through a broad transformation to a modern media business.

Preston and I became friends over our mutual love of aviation and media, and our conversations are always wide ranging and leave me with a new idea or view of the world. I’m very excited to share today’s episode on niche media and publishing.

Over the course of our discussion, we talk all things print publishing, why your favorite magazines aren’t what they used to be, why the print is dead narrative is misleading, FLYING’s fly in community plans, how to grow an editorial team, and aviation puns. Enjoy.

Clips From This Episode

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Alex Bridgeman: Thanks for coming on this show. I’m super excited. I’ve been really, really excited about this episode for a long time because I’m a bit of an aviation nerd. And so, it’s been fun to get to know you through FLYING Magazine and Craig and get to hear all about how that’s working. How’d you get to FLYING though? What’s the path up to FLYING Magazine for you?

Preston Holland: Yeah, so I moved to Chattanooga, the Chattanooga area in 2012 and went to college and graduated, was working in the area, married a girl from the area. And so, we stuck around to be around her family. And I got incredibly engaged on small business Twitter because I was running a turnaround for a service business. And it’s funny, there’s this intersection of small business Twitter, real estate Twitter, and media Twitter, and I’m really not sure who the catalyst is. I have some theories, but I’m going to let them stay anonymous of who I think might be the catalyst of it. But it was really interesting. I got really engaged and I started really talking about fundamental things that I was thinking about and things that I was doing and things that I was experimenting with. And early on, engaged with Nick Huber, Sweaty Startup, this was probably pre 10,000 followers from Sweaty Startup. So, I am an OG Sweaty Startup follower. So, started engaging with him. And then slowly over time, started building not a huge following but a really engaged community. That’s what I really enjoy about Twitter. And Craig Fuller kind of crossed over into that because I was always keeping up with Chattanooga builders and people that are doing really interesting stuff. There’s been a few really interesting companies that have come out of Chattanooga in the last five or six years, FreightWaves being one of them with a big focus in supply chain and logistics and with Chattanooga being a huge logistics hub. And so, he and I started engaging on Twitter and kind of became friends over time. And then he messaged me probably in June and said, “Are you looking for a career opportunity?” And I learned really early on in my career that the answer to that question is never no. It’s always happy to have a conversation. And so kind of one thing led to another, and he said, “I’m buying a magazine and we’re going to turn it around and create an aviation media business.” And I said, “Sounds really interesting. I’ve always had an affinity towards aviation.” So, I said yes and jumped on. So, we finished the acquisition in late July. I’ve been there ever since.

Alex Bridgeman: Are you a pilot now, too?

Preston Holland: I’m not. I plan to start my training. I just had a daughter four months ago. And so little kids kind of take up a lot of your time. And so, I am not currently a pilot. My father flew Cessna 182s. He flew checks back in the day. So, for all of the really young guns listening, the under twenties, back before there was bank transfers and there was the internet, you used to have to physically fly documents back and forth to each other. And so, there’s this entire ecosystem of pilots back in the 70s and 80s, I think into the 90s for a little while, where they would fly important documents that might need a wet signature back and forth. So, you’d get a phone call at 10:00 PM and say, hey, we have this document that needs to go from Atlanta to Orlando. So, my dad would go pick up the document. He would go get in a Cessna 182 and would fly from Atlanta to Orlando. And so, I grew up really dreaming about aviation and he’d tell me all these interesting stories and instilled that passion for me. And so, my dad actually passed away about eight years ago, and my mom found, as she was moving, she found his logbook. And so, now that’s one of my prize possessions. I can kind of thumb through it and see some of the places that he went. For aviators, the logbook is a really important and special piece. So, that’s been really cool.

Alex Bridgeman: That’s very, very cool. I ask because there’s quite a few folks, quite a few pilots on the FLYING team and they’re obviously a very passionate group, pilots generally are, and a lot of them want their folks who work with them to be pilots because that shows that you have this same love of aviation. I’d be curious to hear a little bit more about what that culture looked like when you arrived in July. I assume there’s tons of passion there for aviation and media, but what are some of the nuances that you discovered as you got into the business more?

Preston Holland: So, yeah, first I’m going to give you a little bit of background on FLYINGmagazine, just so that it paints a better picture for you and the audience. It’s been the number one name in aviation since 1927. So, it was formed as Popular Aviation. So that was the original title. I think that lasted for two or three years. And if you’re thinking, oh, that sounds like Popular Science, it was published by the same people. It was all in the same group. For a long time, FLYINGand Popular Science were sold together kind of as it went through- they split apart in the early 2000s, but for a long time, they were partnered up together, were published by the same publisher. So started as Popular Aviation and then adapted the name FLYING and has for a long time been written from the pilot’s perspective. So, you have this huge group of pilots that came out of World War II, and so that was a huge tailwind. Yes, there is a pun. That’s the one thing about being an aviation, there’s always a pun for it. You can have a 10,000 foot view, there’s a pun. We’re going to take off, there’s a pun. So anyways, lots of puns in aviation. So big tailwind was World War II, all these pilots coming back from the war, having been very involved in aviation, kind of picked it right back up. So big tailwind there. There was just a large population of pilots. And so FLYING Magazine really became the voice of authority for them. So, if you think about if you’re passionate about something, whether it’s a hobby or whether it’s a job, because flying can be both, flying the activity can be both a hobby or a career, really it became the authoritative voice for that group. So FLYINGis an independent media organization that has only the pilot’s best interest in kind of the reporting. So really it has been written from that pilot’s perspective for a long time. Somewhere in the late 90s, early 2000s, there was kind of this decision to be very technical. So, FLYINGbecame a very technical publication, which was great for that time period because print kind of was having its heyday in the 90s, really 90s, early 2000s, it was the number one thing that you needed to be in as an advertiser. And so thick books and lot of revenue coming in and everybody reading it. So, then kind of as we enter the late 2000s, entered into the 2010s, print is starting to see this significant decline as digital is really having this massive uptake. And then you have that combined with the 2008 financial crisis really impacts aviation in a real way. And so, you have this- you have two things happening simultaneously. You have print becoming less of an adoption method for media consumption. And then you also have this financial crisis that significantly affects the passion of aviation. You have airlines that are freeze hiring and pilots are coming out of their training and can’t go anywhere. So, FLYINGreally started focusing on speaking directly to the pilot in the front of the plane and trying to give them lessons and things from the cockpit, which is really great because that’s what the voice had been for a really long time. But the adverse effect of that is that, over time, it became less welcoming for non pilots and became much more internally focused as opposed to looking externally and welcoming other people into the activity, so into the activity of aviation. So that’s really kind of what we discovered. Now, the team at FLYINGwhen we joined had a long history in aviation media and they were really good at what they did. The editor in chief, she has been with the publication for a couple of years, previously had been in other aviation media properties. So, she really spoke the language. She understood the audience. And so, her being a pilot and writing from that first person perspective has been phenomenal. As we’ve kind of expanded out and added more voices into aviation, I’ve been trying to really focus on speaking to welcoming those that might not necessarily be inside of the community and welcoming them in, really focusing on the lifestyle of aviation, really focusing on what does aviation unlock for you. If you are a pilot or if you aspire to be a pilot, what does that mean? And then also adding in some of that technical component, but really having this nice balance. And so as we came in in July, that really became the focus of the team and the Q1 issue really was that a lot of the reader feedback was there is something in this for everyone from the most technical pilot to the person who has never flown before and also to the person who’s looking to buy their first aircraft, to the person who is looking to upgrade to their next level of aircraft, really something for everybody. And so that’s really been our focus going forward from a content perspective in the magazine as well as on the website.

Alex Bridgeman: Can you talk a little bit about the process of acquiring them from Bonnier because from our discussions, Bonnier owns a lot of boating magazines and has a strong focus there, and so FLYING was perhaps less of a focus for that organization. Can you talk about life under Bonnier and then part of the sale process to Craig?

Preston Holland: Yeah, absolutely. So, in a lot of these enthusiastic magazine media brands, because of the need for scale and the need for shared resources, a lot of times you have these pools and buckets that are adjacent to each other but not necessarily core audience. A great example of that is what they’re doing over at Outside Media. And they’ve done a phenomenal job of finding these affinity groups. So, you have ski, you have yoga, you have rock climbing, you have trail running, you have just running in general, a lot of these things that have a lot of audience overlap or affinity overlap. And so, you have this beautiful shared resources piece. Bonnier was attempting to do that kind of back in the late 2000s, early 2010s. And so, they acquired a lot of magazine titles that they believed had an affinity. So, you think about the guy who owns a boat probably already or also owns a plane. So, there’s an affinity there. What they found, I believe, over time is that the affinity was less tight than they originally had in theory. And so, they had probably four or five boating focus titles. And so, a lot of those got the attention of the publishing group, and FLYINGbecame less of a priority. That’s simply because it makes more sense if you have somebody who can write about boats, they can write about different types of boats. And so, if you have a boating group, then that’s a shared resource. That’s just one example. And so, FLYINGhad kind of been- not necessarily had the attention and focus that the boating magazines had. Now, here’s an interesting story. Craig Fuller, who is now the owner of FLYINGMagazine and the CEO, shares a name with Craig Fuller from an association in aviation. So, the name Craig Fuller is known in aviation but not necessarily the Craig Fuller that we all know. So, when he reached out, they immediately took his meeting, and he theorizes that the reason for that is because he shares the name with the other Craig Fuller. So, we have a lot of hypothetical t-shirts that we make inside of FLYING. And one of the t-shirts that we’re going to make someday is “Not that Craig Fuller.” So that was kind of a funny way to do that. So, he reached out to them, had picked flying back up after he had fired himself from every job at FreightWaves. And so, he started looking for great aviation media and couldn’t necessarily find it. And so, he, as a media entrepreneur, said I think I can do this better. And so went and found the actual activity flying. If you think about name, like it’s the perfect name for the activity. And so, went and acquired it and went through the due diligence process, and here we are on the other side.

Alex Bridgeman: I love it. And a big piece of his thesis for acquiring FLYING was that print is not dead and high-quality print can be done well, or just high quality content generally can be done well, and it needs to be done well. In the initial few months, what were some of the new directions that you felt FLYING had to go into to become a more modern publication beyond just the higher quality print? Like I’m assuming there’s dozens of other examples in FLYING.

Preston Holland: As we looked at the sustainability of the business long-term, there’s a couple of variable costs that you look at when you look at a physical print medium. So, in a digital only environment, your content delivery cost is frankly quite low. You think about you have to have an email provider, so MailChimp, you have to have website hosting like an AWS, you have to have a WordPress license, maybe some plugins, and then you are kind of off to the races. Social media is free. If you want to do paid acquisition, that’s one thing. But in magazine printing, there’s this whole other piece of variable costs that you have zero control over. So, you have the price of paper, which right now, thank you, all of the different things that we’ve experienced over the last two years, paper cost is through the roof. You have mailing cost which has five scheduled increases to happen this year. So mailing is expensive, and it’s a variable cost that you don’t control. So, as you look at that with print magazines, those are your two main drivers. Your printer has- whoever you choose to do your printing has their variable input costs, therefore it affects a little bit of your printing costs, but your main driver is that paper and that mailing portion. So, what we decided to do was, in order to limit our exposure to that risk, we were going to take the publication to a regularly quarterly schedule and then have the subscription actually support that magazine. So, in kind of the yesteryear of magazines, a lot of subscription prices, if you’ve got a subscription for eight bucks or something like that and the magazine printed 12 times, it costs about a dollar to fulfill that magazine. So, the publisher is actually losing $4 on your subscription. There’s a lot of that happening. If you look at Time Magazine, it is a great example. The Time of 10 years ago is not the Time that it is today. You look at Newsweek. I mean name the publication, and you can see the effects of that fact right there, that there’s these variable costs that you cannot control and then you’re selling subscriptions at a loss in order to have a large audience. So as your variable cost goes up, your spread that you’re paying for that one subscriber reader goes that much higher. And so that was one of the big things that we saw. So, we decided to take it to a quarterly, a regularly quarterly magazine. Now we do have two special editions coming out this year because of what we heard from our commercial partners and kind of what we- after we made the decision to go quarterly, we had a couple of people approach us to say, hey, we want to do these other two issues. So, we went ahead and did that, but we’re promising four to the end customer, and their subscription price is priced in such a way that that becomes self-sustainable over the long term. So, if all the advertising dollars dried up tomorrow, in theory, your X dollar subscription now covers all of your costs to actually print the magazine. So that was one of the huge changes that we made that not a lot of publishers are able to make because they have all these titles and that type of a decision has a lot of downstream effects. And so that was one of the big adjustments that we made right off the bat. And it’s been really well received. I mean, we went from a 72-page book to a 114-page book. And so, the amount of content is higher per magazine pretty significantly. And then we have a very strict ad-edit ratio, so you’re never going to see more than 20% of ads in a FLYINGmagazine. And so, really having that editorial driven content is a big thing for us. And so, it’s been really well accepted by the community. We’ve had a lot of really positive feedback from commercial partners and longtime subscribers alike. And I think if we look at magazines, what is magazines’ future? If you said, Preston, what’s your crystal ball for the future of magazines? I would say there’s really only two options. There’s shut it down, which is happening left and right. Or there’s you’ve got to upgrade it because the status quo magazine just isn’t going to work long-term. So that’s what I see in the future of the magazine industry. I mean, if you look at the Meredith deal that went through, the Meredith Dotdash deal that went through a couple of months ago, they’re announcing the sunsetting of some magazines and then the upgrading of other magazines. So, I think that we’re going to see this a lot more across the industry, across the magazine industry, especially as we look at the just influx of information that we’re getting digitally. There’s something about that print piece that still resonates with readers. And I think that we’re actually going to increase what we see from magazines.

Alex Bridgeman: Yeah, I took that idea to the extreme with the Handbook and just making it all print, no ads, and very, very high-end paper wherever we could. And the paper costs, we are about to do the next issue, so we’re feeling that one, too. We’ve talked a lot about how print is dying is not really what you think it is. There’s something slightly different going on. And especially with legacy systems being a big challenge there. Can you talk a little bit more about that concept of why print is dying is probably not what we think it is?

Preston Holland: Yeah. So, kind of alluding to a little bit of what I was saying earlier about taking subscriptions at a loss in order to grow your rate base, this is a really common practice in print media. And everybody across the industry is now looking at how do we get rid of that type of practice and have a direct relationship with the consumer? So, there’s a legacy fulfillment provider that all of the magazines that you and I probably have ever read, the likelihood of them being on that system is pretty high. They kind of are the monopoly system. The way that they process data on their main frame is it runs in batches. And so, you lose data pretty quickly when you start talking about main files. So, you think about modern database infrastructure and you think about one to many relationships and things like that, their system is not built like that. It is not an instantaneous database. And so, when you call on it, they charge you per API call on a subscriber file that technically, as the publisher, it is your file. So, it’s this really old school way of thinking when you think about data. What that means is that creating any sort of products or services that are outside of just the print medium, because they do the print piece well, they don’t do anything else well, and so if you’re trying to introduce this one-to-one relationship with your consumer and if you want to say link something of their print behavior to something that they have digitally, in order to do that, it’s either not possible, or it is incredibly inaccurate when you actually get the data sets. And so that has caused a couple of things. One is there’s a really disparate experience between digital and print. So, it either is a great print experience or it’s a great digital experience. It’s very hard to get both and kind of in the ecosystem of today’s subscriber files. The other piece is that you have all of these, the fulfillment house takes in mail and checks and all of these things that, frankly, I don’t use checks, but there are still people out there that use checks, and they all read magazines. There’s this crossover between people that like to use checks and people that like to read magazines. But they’re taking in these subscriptions to the database and then trying to bolt them in. Well, a lot of these subscriptions that they’re taking in are through agent sold subscription services. So, if you think about the people that come to your door and walk up and they knock on your door, it doesn’t happen as much recently. I don’t get them, but it still does happen from time to time, the door-to-door magazine salesman. They’ll walk in and they’ll say, “Hey, I’ll sell you these six magazines,” and one of them might be FLYING. And so, the remittance to the actual publisher is sometimes below a dollar for the term of the subscriptions. So, the subscription might be a yearlong subscription, but I only get, as the publisher, $1 in revenue. And so, if you iterate that across your subscriber file, over time, you’re relying so much more on advertising to be your revenue driver. Well, when you rely really hard on advertising to be your revenue driver, market forces are much more at play when you talk about advertising, then you’re talking about with an impulse buy of a magazine subscription. So, it really causes you to cut costs in places where it’s not necessarily the right decision for the end consumer, but it has to be the right decision for the long-term sustainability of the publication. So, this is kind of the historic mindset. So, okay, I’m going to cut my paper quality because it’s going to get my weight down, it’s going to get my paper costs down, and therefore, my mailing cost is going to go down and my per issue cost is down. And so, it balances out the equilibrium. That’s really one of the only levers that you have to pull as a publisher when you talk about sending out a print magazine, or you can sell a bunch more ads, which we’ve all read magazines where it just feels like a big ad, or you can trim down your editorial content to where you only have one voice in your magazine. So those are kind of the levers that you can pull. And when you take on all of these subscribers that you’re losing money on, you have to go to the other levers to pull in order for your business to be long-term sustainable. So, I think that’s what we have seen when you look across the magazine industry. That’s why your favorite magazine is not as high quality as you once remember as a kid. Do you remember- I remember Time Magazine used to get delivered to my house. And I recently resubscribed in doing market research on all of these different processes and systems. When it came, I was really surprised with, frankly, how shitty the quality was. The paper was thin. You could see through it. It might’ve been 70 pages, but it was very, very thin. And so, I remembered, you think back to like- or National Geographic, that is another great example. You remember seeing those in the library as a kid and saying, wow, look at all these beautiful National Geographic magazines. It is not nearly what it used to be. And a lot of that has to do with taking on these other subscriptions. So really saying, look, if you want the magazine, you need to pay for it in essence, from a subscription standpoint, makes longer term valuable magazine companies. So, I think that’s why your favorite magazine is not the quality it used to be.

Alex Bridgeman: Your point around the thin paper is definitely true. The one- you see other magazines, like I’m a fan of the Economist and I think they have a- they appear to have a very low number of ads. I don’t know what their like ad requirement is, but it’s pretty low. And I love that sound, like this sound, like that’s my golf ball in a hole sound for me is like when a print magazine bends like that. When you think about the other products of FLYING, so you have podcasts, you have the email newsletter, there’s the print magazine, digital, part of what Craig did with FreightWaves was there is the media business and then there was the data business on the backend that had- both of them were self-sustaining and fed off of each other. If you think of FLYING, there’s not a clear data business to be built, but there’s some other ways like through real estate or flying communities, or I imagine there’s a bunch of other possibilities out there. When you thought about the different products you could offer kind of your true fans, your diehard group of fliers and pilots, what kind of products did you consider and how did you land on fly in communities?

Preston Holland: Yeah, so that was one of the big things that Craig and I talked about early on – how are we going to monetize this outside of just a media business? And so, we looked at data and we looked at the landscape on the data side, and there really was a lot of people that had done this better than we could have in the short run. So, we can acquire them or we can try and build it, but for the time being, that wasn’t something that we were looking to tackle right this second. So, we were looking for different ideas and he sent me a Zillow listing of 1200 acres outside of Chattanooga. And I looked at it and I said, “Huh, that’s interesting. What do you want to do with a big farm?” And he said, “We’re going to build a fly in community.” I said, “What’s a fly in community?” like most people say. He said, “You live with your plane.” I said, “Okay, well, that’s interesting.” It kind of was birthed out of we were looking for hanger space to have a media center and we were on a 5 to 10 year wait list at every airport in the area. Airport managers laughed at us when we told them what we’re looking to do, which was build a hangar that wasn’t really meant to hold planes, but it was more meant to be a media center. And so, we said, well, I guess we’re going to have to build it. And then, kind of the fly in community piece, we went to Oshkosh, which Oshkosh is the largest air show in the world. It is the busiest airport for seven days. It is busier than Atlanta. It’s busier than O’Hare. If you really want to see something interesting, go look on YouTube and just look up flying into Oshkosh because it’s fascinating. It’s pretty scary. And it’s a miracle that not more accidents happen. But we were there and we realized very quickly that aviation is a community activity. It is not just a side thing for people. It is their identity. And so how do we replicate that in real life? What better way to do it than to do it through aviation real estate? And so, we are creating the world’s premier fly in resort and community. There’s going to be nothing quite like it. There are other fly in communities that have nice houses. There are other fly in areas that have great hotels and amenities. But we’re going to marry the two together so that you can fly here, live here, and stay here. So really what we’re trying to do is create that community. If you want to live here full-time, you can. If you want to just come in on the weekends, you can. There’ll be a club aspect to it where, if you’re a homeowner or even if you’re a guest, you can join into- you can join the fields and become a member and get discounts at the hotel or be able to access the fuel farm or different things like that that really allow for this sense of community. And then, creating onsite amenities like a hotel and like a grocery store and like a coworking space and a gym and things like that that allow for you- If you don’t want to leave, you don’t have to. Or if you just want to fly in and your destination requires you to go by plane, you don’t ever have to get into a car. So that’s kind of the idea behind it. We’re always looking for different ways to monetize it, but that’s been the big focus for us recently.

Alex Bridgeman: I aspire to be a resident of one of your communities. That sounds like it would be amazing. Is there a plan to build more of these fly in communities or is this a kind of a trial run, see how it goes, if it works as we think it might, then we do other things or we change course and try other different products within FLYING?

Preston Holland: Yeah. So, we have specifically designed this concept to be very portable and repeatable. And so, everything that we’re doing, we’re writing the playbook so that if we or somebody else wanted to recreate this, we would be able to do that. Right now, we’re really just focused on the one community but with the concept that this could become a portable idea to be able to take to other places. We have seen an insane amount of inbound traffic via not a high amount of effort. We’ve had over 450 inbound requests for information about lots and that’s via one advertisement in the magazine and we ran an article on the website, and that was it. So, it’s interesting. I told Craig this. I said I knew that media brands had authority, and I knew that that was a big reason why it’s important to run them and why it’s important to run them unbiased and things. But I said I did not realize that when this ran through FLYINGMagazine, that it would generate this much anticipation and talk. And you want to talk about product market fit, I mean, we would’ve been really happy at 50 to 100 inbound. I think we had 50 inbounds in the first two hours of making the article live on the site. We ran it on a Friday. It ran at 9:30 in the morning, and my phone, because I get notifications every time somebody submits, my phone didn’t stop until- it still actually hasn’t stopped; I’ve gotten two since we’ve been on this podcast. So, the level of demand in the community is really high. And I think the demand for not just another air park is what is really interesting. We’re not building- we got mentioned on a podcast anonymously that, oh yeah, all these old dudes fly in with their planes. It’s really not what we’re building. Is there going to be some older people in the community? Sure, because they have disposable income. But it’s really going to be that tech entrepreneur that wants to live in an area with low taxes, can work from anywhere. You can have gig speed internet, and you live with your plane. So, guess what, if you want to be in Atlanta for lunch, you can do it, and you can leave your house at 10 o’clock. If you want to go to Asheville for the afternoon and play golf, you can do that. If you want to be in Nashville to go to a business meeting with another tech entrepreneur in your airplane, you can do that. We’re really trying to build something that has appeal for all ages and really has that cool factor that you really don’t find in a lot of aviation real estate projects right now. There’s one out west called Alpine Air Park, and it is the mega wealthy, the mega rich, beautiful, huge houses. I don’t think you can get in there right now for under $3 million. We will have some of that, but also there’s nothing to do there. Their FBO is shutdown; there is nothing to do in the town because they didn’t think about amenities when they were building the original concept. So that’s really what we focused on is building amenities that’s going to make people want to come here multiple days out of the year, multiple days out of the week, want to host people here. So, rock climbing, mountain biking, a day spa, an overnight hotel. Like I said, the FBO with the fitness center and the coworking space, really creating a planned community. So, we’re working with a real estate consulting firm that’s helping us actually plan the community and what do the phases look like in order to have the maximum amount of appeal and draw. I mean, so you think about somebody like our mutual friend Joe Poland from Twitter who flies a Cirrus Sr 22, and he uses it for his business purpose. He’s got young kids and he has a wife, and they want to do stuff. And maybe he has something that he has to do for work at one of his properties, but he’s trying to have vacation in the interim. We want to create a location for him and for people like him where you fly your family in, you come in, you have a car there. It might be your secondary home, but because of the beautiful state income tax laws in Tennessee and the really low property taxes, it’s going to be less expensive than your home in your higher tax area. And you can come in, you can stay for four or five days and say you need to go up for a meeting at one of your buildings, you can pop in the plane and you can leave. Your kids can stay, your wife can stay, and you can come back and meet them or if they want to airline back or whatever. This can be a hub for you because the beauty of having an airplane and being a pilot is that you’ve unlocked a much larger area than you would have had if you didn’t have that airplane.

Alex Bridgeman: Yeah. And I wonder as this concept fleshes out and then potentially you build others, if you create this almost like a pass. Like if you think of like ski passes, like the Icon pass, you could create the fly in pass that you build up points through your spending, and maybe there’s different plans that get you access to different levels of amenities. And your passes can be used at other fly in resorts run by FLYING. So, if you have one in Colorado, you have one in Texas, Florida, Northeast, you could fly to all of them and almost like a punch card, like get into all of them. Maybe if you go to all of them, you get some sort of like special thing you unlock because you flew into every resort. So, there’s probably something more than just the fly in real estate itself that becomes really valuable over time, like that buy-in, I imagine, becomes a huge asset over time if this works out and you could build out other fly in resorts across the country.

Preston Holland: Yep. No, that’s exactly right. I mean, that’s definitely something that we’re thinking about. And partnering with other like-minded aviation communities in order to accelerate that timeline is also something that we’ve definitely been discussing and considering.

Alex Bridgeman: Yeah, that’s going to be very cool. There’s obviously been a ton of changes at FLYING and a lot of new products or redesigns or ideas here. How did you take the FLYING team from the point where they were in July to now? What kinds of transformations have had to happen within the team, new hires, or changes? What does that look like?

Preston Holland: So we’ve significantly increased our editorial staff, which has some great commercial downstream effects because the more editorial that you have going out in a digital world, the more you get in front of commercial partners. So, it’s this beautiful loop – oh, our company was mentioned in FLYING Magazine, oh, we haven’t advertised with them in a while, but they’re clearly doing something different. So that was one thing, we brought in a lot of journalists that were specifically writing about very specific topics. In the magazine, in kind of traditional magazine publishing, you end up buying a lot of content from independent writers, and then you have a main editor who is kind of setting budgets and doing all of the editorial decision making. And then you have somebody selling into and selling against that product. What we’ve done is we’ve hired very specific writers, either full-time or on contract, to write about very specific things. So, we brought in somebody to specifically focus on the training and schools market. We brought somebody in and had them focus on specifically modern flying. So that’s going to be [inaudible [RD1] 42:37], that’s going to be advanced air mobility, that’s going to be sustainable aviation, things like that. We brought in somebody who specifically writes about destinations. Where should you go in your airplane, and here’s an editorial piece behind it. So, really trying to diversify the editorial team was the biggest lift, outside of standing up systems and moving all of this information into our new systems. The biggest lift was doubling down on that editorial and really writing more engaging, more interesting content for it. So that was the biggest change, bringing in writers that might not necessarily have previously- maybe a subject matter that might not have previously been on the brand. And then the community has accepted it in a great way. It’s very quickly become a lot of our most popular content has been those themes for people that we’ve brought in. So that was the biggest lift, kind of that hiring aspect early on. And then just standing up systems and making sure that everybody can operate inside of them because we do function a lot like a startup. Everybody wears a lot of hats. And so, getting all the existing team to realize, hey, we’re all going to wear a lot of hats for right now. And then, bringing the new team in and integrating them together, it was a challenge, but it was a fun challenge. And it’s been really cool to see the team really embrace each other and celebrate wins and write really cool content in the written form. And then, we’ve got one guy on our team who’s doing some interesting video work for us that wasn’t necessarily a core focus of FLYING previously. And so, doubling down on that video aspect, podcasts, creating all these new properties, that’s been kind of the most rewarding piece as well as has required the biggest lift.

Alex Bridgeman: What have been some challenges though? I imagine that’s not- a lot of this change is happening, from the outside, it looks like it’s happening pretty quickly. There have to be some growing pains or challenges within doing that. What have been a few examples thus far?

Preston Holland: I think shifting the mindset from the existing team from what FLYING was to what FLYING can be. There’s this huge pushback when we decided to go quarterly, and it was a decision that we made. There’s a few reasons why we made it, but we really wanted to make that upgrade an invested product. And so, shifting that mindset from being a monthly magazine to being an online media business that also has a magazine was really tough because you have people who have been doing aviation media via a monthly print magazine in this way for sometimes 30 years. Getting them to understand, hey, this is the way of the future, this is the way that we’re going to be able to be successful going forward, we really want to get you guys on board with this, that was probably the hardest part. And then the other challenging piece was not coming from print. When we originally talked about the acquisition, the print was going to get sunsetted after six months. And so not being necessarily print guys, and then having to figure out how to get your mailing permit set up and how to calculate your ad-edit ratio and how to execute customer support and how to- all of those different things, figuring that out in about a six-month time period was definitely challenging. I’m still not an expert. There’re still some things that are like, oh wow, I didn’t even think about that. But those were the two main lists, both from a process standpoint and from a people standpoint.

Alex Bridgeman: That’s fantastic. I wish I could talk to you for two to three hours a day. That’d be fantastic, but we do have to close here. But I would love to get your thoughts on a few closing questions. What college class would you teach if it could be about any subject you wanted?

Preston Holland: So, there’s a reason why I’m going to pick this one. It’s because the most impactful professor that I had in college, his name was Alan Smith, he was a banker M&A guy. So not only was he a banker, but he was a banker of banks. So, he did bank M&A’s. That was what he did full time throughout the year. And so, he would teach one class from 6:00 PM to 8:50 on Wednesdays. And he was probably one of the only professors that I had that was actually in the game and was actually doing stuff. He taught financial evaluations. And the reason why I would pick that class is not necessarily because I think that I am the world’s best at financial evaluations, but because he made such a huge impact in bringing in real-world examples into that class. And I really learned from him a great way to bring real world examples into academia that I would want to teach that class kind of in his honor and teach it almost exactly like he did.

Alex Bridgeman: I love that. That’s a great answer. What’s a strongly held belief you’ve changed your mind on?

Preston Holland: So, growing up for a long time, when I was early, probably middle school, high school, I saw this path, this path to success. And the path to success looked like getting into a good college, network, get into an entry-level job, climb the corporate ladder, and then eventually you’ll get there. So how do I set myself up for the next step? So, I was constantly looking for what am I doing tomorrow? What am I doing today to set my tomorrow up better? So always head up looking down, downstream at what’s coming up. And one thing that I’ve learned over the past probably 10 or 15 years is that it doesn’t look like that at all. I would not be in the position that I am at if I didn’t go to a small liberal arts college. I would not have a lot of the relationships and the network that I have if I didn’t make those decisions. I wouldn’t be in this area. I wouldn’t be married to the person that I’m married to today. And so, I really had this really core belief, even after graduating college, I still had this thought of, okay, well, I need to get back on track with kind of that linear progression. But I’ve really been learning that it doesn’t look like that. And it a lot more has to do with keeping your head up and looking side to side then looking downstream at kind of what you’re looking for. And so, like always looking for opportunities to grow and change today. And if you make the decision to focus on today and to grow and change today, then the long-term goals, as long as you have core guiding principles, those are going to all work themselves out.

Alex Bridgeman: That’s an awesome one, too. What’s the best business you’ve ever seen?

Preston Holland: So, I thought about this for a long time, and I wanted to give an answer that I haven’t heard. And forgive me if somebody has said this, Stripe is the best business that I have ever seen. Has anybody said Stripe yet?

Alex Bridgeman: I don’t think so actually. I’m surprised, but I don’t think so.

Preston Holland: The way that I see it is that Stripe holds such a corner of the market. There’s a couple of people that are trying to come after them. There’s one guy who’s very loud on Twitter about it, trying to come after them. But what Stripe has done is they have democratized payments in a way that you can start a business in about, outside of kind of the legal stuff, but if you wanted to collect payment, you could do that in about 15 minutes using Stripe. All of this old payment tech, it would take three and six months to get everything approved and everything aligned and all of that. Whereas Stripe is really business owner and business operator centric, developer centric, to where you can really build a multitude of businesses off of it. And then they’ve really cemented themselves in the marketplace as kind of that leader. And so, you look at Shopify who’s arming the rebels. I would argue that Stripe has armed the rebel as much if not more. And they’ve done that the entire time while staying private; they’ve just been constantly reinvesting. I mean, I think about all the subscriptions that I have personally, that I have personally paid to Stripe and then on the systems that our business runs off of that pay to Stripe, it is a cash printing machine. And they’re already- the founders are probably already two of the closet wealthiest people in the world, but when they take it public, I think that it’s just going to moonshot from there. So, I love Stripe as a business. I think it’s genius and I don’t see anybody replacing them anytime soon.

Alex Bridgeman: Yeah, it is awesome. And to your point about setting up in 15 minutes, setting up mine was incredibly quick and you just give your subscription key. There’s like a key that you use that identifies your Stripe account. And I remember thinking that I wasn’t done, like there must’ve been a step that I missed somewhere, but lo and behold, it worked. It’s mind blowing how smooth and easy it is. Well, thank you for coming on the podcast, Preston. It has been so much fun to have you. This is one of just many chats that we have that it would be fun to record all of them and publish, but thank you so much for sharing more of your time. I always love chatting.

Preston Holland: Yeah, Alex, thanks so much for having me. And I just want to give you a quick shout out at the end of your podcast. A lot of the guests that you have on and you personally asking them really great questions has shaped a lot of how I think. I mean, I can specifically remember a couple of episodes that have been super impactful for me. And so, I appreciate the work that you’re doing and the people that you’re bringing on here, very, very thoughtful people. It’s never a conversation that doesn’t change how I see the world in some way. So, I appreciate you.

Alex Bridgeman: That’s very kind of you. Thank you.

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