Why You Don’t Have to Be Rich & Famous to Fly Private with Nik Tarascio – EP 123

Interview with Nik Tarascio

Rick Sapio

Why You Don’t Have to Rich & Famous to Fly Private with Nik Tarascio

How much money do you really need to fly private? It turns out, you don’t need as much as you’d think.

When I was younger, I often wondered, how in the world does someone afford a multi-million dollar plane? I used to think you had to put $15M down to buy one. The reality is, most people finance it over time, and in the process, they take advantage of some serious tax write-offs.

Imagine for a moment that you had a BIG exit. Amazing! Except there’s one problem. Now you have to worry about a huge tax liability. I can’t tell you the number of business owners who get nailed with an insane tax bill because they didn’t have a plan in place.

Luckily, through the power of accelerated depreciation, financing a plane is one way to offset the amount you’d need to fork over to Uncle Sam. Not only that, but it offers some pretty cool benefits from a lifestyle perspective.

Am I suggesting that everyone go out and buy a plane? Absolutely not. BUT, it’s worth noting that it’s not just an option reserved for the rich and famous. You’d be surprised at all the different ways you can be an owner—and we’ll uncover those options (and a whole lot more) on today’s episode.

I’m talking with Nik Tarascio, who grew up in the aviation business and has been flying planes since he was in grade 3. He’s now the CEO of Ventura Air Services, an aviation company that he scaled to unprecedented heights during the pandemic, defying industry odds by doubling its fleet despite the steep drop in travel.

In today’s conversation, you’ll learn:

Why you don’t have to be a billionaire to enjoy the freedom of private aviation.

The tax benefits to buying a plane—and how it’s done!

✅ Why true joy is not found in material pursuits but in meaningful relationships and sharing experiences with those closest to you.

Featured on This Episode: Nik Tarascio

✅ What he does: Nik Tarascio is the CEO of Ventura Air Services, a fast-growing aviation company focused on aircraft sales, maintenance, and private air charter services. Nik is also a licensed jet pilot and the author of “Own Your Own Plane: It Costs Less Than You Think.” As a pilot and an industry leader, he has worked with and served influential leaders in politics, medicine, entertainment, the arts, and philanthropy. A licensed pilot since 13, Nick is rated to fly jet, turboprop, and piston aircraft, including Learjets. In addition to being a jet pilot, he has extensive experience as a certified aircraft mechanic, avionics technician, and successful aircraft salesman. Nick’s been featured in Fortune, HuffPost, Business Insider, Newsday, Aviation Pros, and on BBC Television. Nik is also a multi-instrumentalist, songwriter, and performer who has released three albums and continues to write new music.

🔎 Where to find Nik Tarascio: LinkedIn | Instagram | Facebook

Key Takeaways with Nik Tarascio

  • Why flying private is NOT just reserved for the top 1%
  • Tax benefits to buying a plane—and how it’s done!
  • What flying planes can teach you about the fundamentals of business.
  • Flying as a way to accelerate connections and master your time.
  • Which type of plane ownership (if any) is right for you: full owner, partnership, fractal ownership, chartered trips, private jet cards, and more.
  • Why you don’t need as much money as you think to own an aircraft.
  • Understanding the private jet market and the different classes of plane buyers.
  • How to avoid raising entitled kids.
  • Can you really afford it? Follow this rule to avoid getting in over your head.
  • Why chasing material possessions will never make you happy. Do this instead!

Nik Tarascio | The Private Plane Tax Loophole

Nik Tarascio Tweetables

“I’d been chasing these external validations of who I was as a person. And at some point when I hit a certain wealth level, I was like, I actually don’t think it made me feel anything; I don’t actually feel any better.” - Nik Tarascio Click To Tweet “I didn't fly to get somewhere. I fly to build connections and to create something really special. And that's what I think airplanes are really all about.” - Nik Tarascio Click To Tweet


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Read the Full Transcript with Nik Tarascio

Justin Donald: What’s up, Nik? So glad to have you on the show. Thanks for joining.

Nik Tarascio: Absolutely. Thanks for having me here.

Justin Donald: This is awesome. So, it’s fun. You and I got a chance to get connected through a mutual friend, John Ruhlin. I was in the market shopping for a plane with a buddy. I was curious if I would even share some of the details of that, but I had a friend that was really excited about getting a jet, needed some tax deductions, was going down the rabbit hole of all these different programs, what’s best and what would it look like if we were to split a plane.

And so, John hears me talking about this and he’s like, you have to meet my friend Nik. Nik is the foremost expert in this space. And what a cool experience I had in getting to know you, learning your expertise, seeing your passion for people, your clients, your friends. So, I’m just excited to have a fun conversation with you today.

Nik Tarascio: Absolutely. I love talking about airplanes. And it was interesting, too, because when we connected, I had no expectation of it going anywhere other than I’m happy to talk about airplanes. Someone wants to potentially buy one, how can I support?

Justin Donald: Yeah, and what’s cool, like I want my audience to know that you recognized in this situation there was really no benefit. Like I wasn’t going through you to do this. We are pretty close to pulling the trigger in a completely separate path. And you just offered up so much time to me first, and then to my friend who is going to partner with me on this. And that was just really cool of you. So, I love that you’re willing to just show up for your friends. And at that point in time, we weren’t even friends, it was like, a friend of a friend. That says a lot about you, Nik.

Nik Tarascio: I appreciate that.

Justin Donald: Well, let’s talk about this. How on earth did you get into private aviation? I know this is a family business, but it’s fascinating to me how someone would get into this space because I feel like there’s a big hurdle to even think that you have the ability to get into private aviation, having your own plane.

Nik Tarascio: So, I tell people jokingly that it wasn’t a silver spoon. It was more of a wooden spoon because I grew up in a flight school. And I got to tell you, there’s not a lot of money in flight schools. It is hard business, but the aviation industry is a curious industry because it’s filled with people that are extremely passionate about what they do. And there’s a very love-hate. It’s like it takes away all my time. I’m flying all over the place. I’m dealing with the most demanding customers, right? We have the most successful people in the world that are our customers with these incredibly high standards, but most of us wouldn’t have it any other way.

So, I grew up, I always tell the story, in third grade, first day of school, my teacher says to me, “Nik, what did you do over the summer?” I said, “I flew a plane.” And she goes, “No, Nik, you flew in a plane.” I said, “No, I flew the plane, and I’m going to become a pilot.” And after insisting that that’s what happened, she called my mom and said I was a pathological liar. And my mom said, “No. Nik actually flew the plane and was logging the time with my husband and he’s going to become a pilot.”

So, I knew then that I had a very, very unique upbringing. But what was cool about that was as I got older, we used to take our friends on the planes, like the kids that I grew up with, like, do you want to come fly with us to Nantucket or Martha’s Vineyard or Boston? And what I realized is it was such a weird world that most people didn’t have exposure to.

So, my life has really been about how do I make that possible for people, right? What’s the question? How much money do I need to have to buy a jet? I literally wrote a book about it. You don’t need as much money as you think. So, I think that’s really how I got here is the family business, but then became somewhat of a calling to say, I don’t want this just to be reserved for the 1% of the 1%.

Justin Donald: Yeah, that is a powerful statement of like, how can I open it up to as many people as I can, my friends, my family, just help people experience this and not just for that top percentile, right? So, here’s an interesting thing. I used to think when I was younger, I was like, man, how do you afford a multimillion-dollar plane, like your own plane? Like this was mind-boggling to me. And I used to think, you had to have all this money, all this cash. You’re putting $15 million down to buy this plane.

But the reality is, most people don’t do it that way, most people finance it over a period of time. There’s a down payment. In addition to it, there are massive tax write-offs. So, just like you have a vehicle that is £6,000 or more and you can take that accelerated depreciation right away day one, regardless if you’ve paid it off or not, a plane is the same in that respect. And so, often, a lot of people, well, let’s say someone has a big exit, they sell their company and they have this huge tax liability, well, one of the easiest ways to reduce that liability or offset the taxes that they’ll owe is to buy something like a jet that has a high cost where they put a little bit down, but they can accelerate that depreciation into one year, right?

Nik Tarascio: Yeah. I mean, the amount of people that I’ve told that to and I have to say it four times before they get it, they’re like, it doesn’t make sense. Why can you buy an airplane and put 20% down and then depreciate the whole thing in year one? My answer is usually, who do you think writes tax law? It’s people that own private jets, right? It’s generally going to be driven by that. So, yes, it’s one of the most incredible tax strategies from a lifestyle component.

Justin Donald: Well, this is perfect that we’re having you on The Lifestyle Investor. And I feel like there’s so much of what you do, what you stand for, what your business is that embodies lifestyle. So, I feel like there’s no better fit than this. But I would love to even talk about how you decided, obviously, as a young kid, you wanted to fly, you wanted to be a pilot. That’s way different than running a business and let alone, let’s not just talk about any business, we’re talking about a business that is private aviation in the realm of the top 1% of 1% of 1%, right? So, how did that happen where you said, you know what, I not only want to be a pilot, I want to be an entrepreneur? And I actually may have the skill set to do it or I’m willing to put in whatever it takes to figure out how to do it.

Nik Tarascio: Yeah, ignorance and obligation are a beautiful thing. So, I generally grew up watching my parents live. I don’t know if you’re familiar with the IMF, this idea that just because you’re great at a skill means you should go into a business of doing that thing. My parents are amazing at aviation. They’re just passionate about that work, but they never really wanted to manage teams. They never wanted to take it to scale. That wasn’t in their desired lifestyle. We want to be on the front lines, like my dad loves flying the airplanes. My mom likes dealing with the customers.

So, I saw this happening and I saw them really just squeaking by, like they were years where things were flat, there were years where we lost money, they were years where we made a little bit. We really didn’t even know. We didn’t have very good accounting at the time. So, I was this musician who was like, I don’t want to be a business guy, but I love my parents and I see how hard they’re working and I don’t want them to suffer. So, I figured, let me help out. And I have three siblings. We all helped in our own capacity.

I just had this foolish teenager optimism of like, I’m a nerd. I went to school with a full scholarship. I’m good at most anything I put my mind to. How hard could it be to run a business? I’m still figuring that lesson out. I’m 42 now and it has been decades. It’s the hardest thing I’ve ever done. It is truly the hardest thing I’ve ever done.

The relatively cool thing about it, though, is that I’ve learned most of how I run a business in the cockpit of an airplane. I flew for the first time on my 16th birthday by myself. I got my full license on my 17th birthday. I was flying jets by 19. And I think many of the principles that pilots deal with is it translates so well to running a business. So, again, I would say it really is obligation and ignorance that have put me here, but I’ve learned to truly find a love for it because it’s the most creative pursuit I’ve ever had to do.

Justin Donald: So, give me some examples. What practical skills have you learned in the cockpit? It’s fascinating to even think about that being the foundation or the place that you learn some of the most important concepts of being an entrepreneur, being a businessman, being a smart entrepreneur. What are some examples of what you learned and how it translated into your business?

Nik Tarascio: So, I created a framework for myself that I’ve never actually brought to market called the pilot mindset. And it really distilled down what those things are. What are those key lessons? So, first, I’ll start with the story. I was flying a single-engine airplane and the engine quit. And it was one of those moments where you don’t have a choice. You said the engine’s quitting. I’m going to have to glide it to the nearest airport.

What was interesting was I did that, we landed, everything was fine. It was no big deal. I followed my training. Everything was by the process. At the same time, I was in my 20s at this point and I was in a really unstable relationship. What was interesting is in the relationship, I denied reality. I kept on being like, this will get better. I’m dating potential and I was suffering and suffering and suffering. But I was like, why didn’t I suffer in the airplane? The engine quit. I didn’t argue with reality. I just accepted that was what I had to deal with.

So, I always saw that as the moment of like, wow, this is the perfect framework for how to operate in business is don’t argue with reality, Don’t operated on, some of us call it hopium, right? Like, don’t dream that it’s going to get better. Just look at it like, yeah, we have money, we don’t have money. This is a hard market. The market’s in recession, whatever that is. It really starts with what is, is what is, and then fly the airplane. And that’s one of the things they always told us. No matter what happens, you fly the airplane.

The people that give up flying the airplane have a really tough time because now, they’re just going for the ride. Someone else is in control or gravity, either one. So, that was first and foremost is really this idea of you can’t be a victim in an airplane. You just can’t do it. It’s the worst strategy.

But then the other stuff I saw that really came to the surface was I’ve never taken off an airplane without having a goal in mind, a destination in mind. No one’s ever said to me, like, Nik, where were you flying to? And I just had a blank stare. Of course, I knew I was going to Florida. Even I was going to lunch, even I was going in a circle around the airport, I always knew what I wanted to do, what my intention was.

So, I was like, why is it that in business, people do things without that clear goal in mind? And I did it. I had even done it. So, number one, get that clear goal, then you get on the runway, right? And when you’re on the runway, you spend a bunch of time accelerating in a straight direction. You’re not trying to go this way and that way and every other way at the same time. But again, in business, we often do that. We’re going to do three different things at the same time. They’re not even in service of each other. So, I was, “Hey, get the plan, get on the runway, and start going down that runway.”

Once you get into the air and you get to a certain speed, you’re kind of free to maneuver. And then I often say, “Well, look, you can fly 50 feet above the trees if you want, but altitude is like cash flow, right? So, if you want to fly 50 feet above the tree line, no problem until something goes wrong, then you’re going to wish you had that extra altitude, but it takes time to get that altitude and you slow yourself down.”

So, as a lot of those principles that came out of that, then I’d be sitting next to my dad. He was training me how to fly instruments. And on instruments, you have this little needle in the middle of the screen and you could have small deviations from them. My dad would always say, “When you see a small deviation, little fingertip pressure to make small adjustments, keep that line centered because if you don’t pay attention to it long enough, it’s going to be a big deviation.” And sometimes, that’s a permanent deviation, like if you hit a mountain. Sometimes, it’s just a big deviation that adds a lot of time. So, it’s a lot of these fundamentals, I said, is probably 10 different things I distill down that I said, this became my leadership style, this became my business management style, all from flying around with friends, taking them to lunch in Nantucket. It was really interesting to see that parallel.

Justin Donald: So, that’s kind of to me just this incredible experience. And I just want to talk about this a little bit more, the whole idea of flying somewhere for lunch, flying somewhere for dinner, like saying, hey, join me. We’re going to go fly to this place for lunch and then fly home, or we’re going to go to this killer restaurant in wherever it is. Let’s call it some place you can’t drive to. Maybe we’re flying down to Florida real quick. You can do that a lot faster in a jet than you can some of the commercial planes, right? You can go a lot faster speed. So, you could get somewhere for dinner and head back home in the same day, in the same even like span of hours. I’d love to hear just some of your thoughts around that because that’s so fun sounding.

Nik Tarascio: So, I really loved the idea of accelerating connection. Like if you think about it and I think you talk a lot about this, it’s all about time. It’s really about having control of your time and your definition of wealth as it’s about having that time, having that time freedom. What I saw is that if I do have a limit, I have the same amount of hours as everybody else, but I want to connect deeply with people. And how could I potentially make four hours turn into what feels like an entire day or an entire weekend?

So, when I would take people on these airplanes and I would do things like not tell them where we’re going, not even tell them we were just going to get a burger in Nantucket, again, a little hop out in New York City and back. What I notice is I would take strangers, I’d literally go on Facebook and post who wants to go flying today for dinner? And I would put five people that I’d never really spent time with on the plane that didn’t know each other. By the end of that flight, everyone had a shared experience of having to surrender, having this discomfort, there’s still a little bit of fear in being a plane for a lot of people, and by the end, they were like, “Yeah, this feels like I’ve known these people forever. We had this amazing shared experience.”

So, again, I didn’t fly to get somewhere. I flew to build connection and to create something really special. And that’s what I think airplanes are really all about. It’s so, yeah, some people love to fly, some people love the actual aviator aspect of it and the airmanship. Other people love the idea of I’m a utility flier, I need to get to a business meeting in Boston, I want to come back. But I never saw it as that. I always saw it as airplanes are a tool for creating meaningful connection and love, right? You want to spend time with the people you love.

Not only is getting there, like being at the destination, part of the love part, it’s being in the airplane, having someone sit next to you and see the wonder of operating this airplane, seeing the wonder of the circulatory system of the planet, right? It’s so cool to see the way the road systems formed and interact. So, that really is why I tell people maybe consider becoming a pilot if you want to foster incredible connections and become the master of your own time.

Justin Donald: That’s just incredible. I even just love the term airmanship. I mean, that is really cool. Just this whole idea of being a good steward, a good example in the air, just a fascinating concept. And I love this spending time, like the goal is to connect people. The goal is to spend time. It’s not about the destination. It’s about the journey as cliche as that sounds, like that is the truth. That is the reality. It’s like, what are we building during this time frame? And I think it’s cool that you involve people, your friends, of course, but cool that you reach out to people on Facebook, you reach out to people, hey, who are some cool, interesting people from different walks of life that we can just put together and see what magic happens in that moment? That is really cool.

So, I’m assuming you have been to some pretty cool places. I am curious, what are some of the places that you’ve been to that you actually need a private jet to get to it, right? Like the airstrip is too small for a commercial plane. There are several places that I’ve been over the last few years that that’s the case. And thank goodness, I had some connections and some friends that have their own jet where we could go, otherwise, it wouldn’t even make sense to go there because it might take a whole day just to get to the destination, right?

Nik Tarascio: Yeah. I mean, America alone is interesting because there are 300 commercial airports in America. And again, this is a rough stat. There are 7,000 airports. That gives you an idea, right? You’ve got the access to 6,700 more airports by flying private. And I’m talking prop planes, jets, whatever it is. And so, from that perspective, like a great example, and again, this is obviously very New England-focused, but there’s a little island called Block Island off the island of Montauk in New York. You couldn’t get an airliner in there. It’s a very, very short runway, but it’s the kind of place you go there and you really feel like you’re in a complete, different world and you’re only 35 minutes from New York City by plane. It’s unreal.

I mean, I feel that way about places I’ve gone in Vermont. Sedona, Arizona is a really cool place if you’ve ever been in there. Literally, the airport sits on a mesa on top of the entire community and you just feel like you landed in this magic Red Rock Canyon. It’s just it’s a way of it’s an interface that is so different from any other means to be able to connect with the world, shave hours off of getting to and from places as well.

Justin Donald: Yeah. And I can tell you there is incredible efficiency in flying into Sedona. I have flown private into Sedona to celebrate my good buddy Hal Elrod’s Miracle Morning movie documentary that came out and we would otherwise had to fly into Phoenix and drive whatever that is, hour and a half, two hours to get to Sedona, which I’ve done many times. It was really nice and convenient to just fly in. You can’t do this unless you have a smaller plane. It’s a smaller runway. You just couldn’t navigate the mountains and everything in a commercial jet. And so, it was cool to just fly in and we’re five, ten minutes away from the hotel.

Nik Tarascio: Yeah, that’s the life hack right there.

Justin Donald: That’s cool. So, for people that are kind of wondering, like, is this for me? Could I do this? Is this something I should aspire to do? And obviously, this is a personal decision, but I think for those that have the means and for those that don’t yet in time finding ways to have the means, it would be interesting to kind of dissect plane ownership or like, how do you use a plane if you’re not going to own it?

So, for some people, it makes sense to buy a jet. It makes sense to get the write-off. They need it. They’re in a season of life where something like this could drastically decrease what they’re going to pay in taxes. For other people, though, it probably doesn’t make sense to own. They’re not going to fly enough. A lot of people think that you can make money with your jet in this industry. That is really hard to do, right?

So, like anyone who thinks that you can do this, that you can just turbo your jet and make a profit like that is just not the reality. But if you’re already committed to flying and there’s a cost to what you’re doing and you want to do it in a more efficient way and you’re analyzing the time and the cost versus the time spent, like there’s a lot of reasons to do it, or even owning your jet over a period of time while leasing it out a little bit. Maybe you can get closer to a breakeven, or maybe you can get closer to an expense that is reasonably justifiable, right? Like Warren Buffett’s plane is called The Indefensible because it’s the one asset that he has that he really can’t justify the expense, right? It’s just like I’m willing to make this payment, I’m willing to cover the cost of this because it is worth it to me.

But then you have another tier of people that maybe for them, it’s better to charter a jet whenever they want to fly or for certain types of trips. For other people, it might be a Jet Card. For some people, it might be fractional ownership. And I’d love for you to kind of help dissect each of these because there are a lot of different ways to fly private.

Nik Tarascio: That’s right. And it is so complex. I mean, there are literally people like ourselves that just help people with this strategy where it’s like, where do you fly to and from because it’s where you start from, where you end up changes the game? How many people you fly with? Whether you have a tax strategy you’re trying to offset, your personal preference is I only fly new or I only fly planes with jet engines, no turboprops. Like there are just so many questions that go into this.

But kind of the tiers that we look at is if you’re flying above 150 hours a year, generally, it makes sense to consider ownership. Just as a rough rule of thumb, again, there are all types of variations. In fact, I’ll just insert a little bit about what we do. Our business, again, we’re a jet charter company. We do maintenance and we refurb sell leaseback airplanes and all that stuff. We created a program, we said, for two types of airplanes, Challengers and Citation Excels, you can own a plane with us and justify it at about 50 hours a year of flying.

But again, we’re this rare company that says we’ll pay all the fixed expenses and all that stuff. So, you have these like you can own it, you can offset it. Then some people say, “Well, what if I partnered up with someone? I want to go 50/50.” That’s an option too. Some people go into these partnership deals. You take that to the extreme and you go, I want to fractionalize.

Interestingly enough, like if you look at the NetJets, Warren Buffett, it’s an interesting model, but it’s the most expensive way to fly because there’s no space for you to offset your cost since all of the people that are fractional owners are all using the asset. There is no revenue producing that’s happening. So, often, again, it’s the most predictable model, but it’s the most costly. You’re going to predictably pay the most and you’re going to get the same thing every time.

Then you have your Jet Cards, which is sub-150 hours. It may make sense to do that, and it makes sense to say I’m only going to do 25 hours a year. I do two family vacations. I’m going to use 12 hours each time I fly. Great. Buy your 24, 25-hour Jet Card, you have it set at a known cost. Again, you’re going to pay a premium per hour, but it’s a known.

And then you have your– I need many different types of airplanes. I’m not sure what I need. I don’t know how many hours I’m going to do a year, so then you just charter and you say, “I’m going to pay what I need. I don’t want commitments. I don’t like the idea of locking my money up.” And again, so you kind of have this full gamut of what’s there with the one little hack that I talk about in my book is most people don’t pay attention to little prop planes as crazy as it sounds. A lot of people actually travel within a much smaller region than they would need a jet for.

So, you literally can buy a small plane, put it on a flight school as crazy as that sounds, people will rent the airplane, like pilots will rent the airplane. And then you could just literally hire a flight instructor or a pilot to fly you around in your own plane. And that is like a fraction of owning a jet. But that’s the thing that people go, I had no idea I could do that. I didn’t know I could buy an airplane for $150,000.

Justin Donald: Yeah. And so, we get into this world of, like, the difference between a plane and a jet, the difference between a prop and an engine, a propeller, for those that are unclear with what prop stands for and a jet. I’d love for you just to kind of dissect that. And it’s interesting because then, when I took my dive into this and for what I was looking into is going to be a partnership deal, two of us, and that very much is on the table right now, which is kind of fun to think about. And so, you start going down this path of like you’ve got these light jets, you’ve got these super light jets, you’ve got medium, you’ve got heavy, you’ve got– I mean, there’s all these different categories. So, I’d love to just have you give a quick overview of what it might make sense to consider.

Nik Tarascio: Yeah. So, I’ll tell you, I serve mostly utility buyers. So, I’ll speak from the span of a utility buyer and I’ll separate the two. The NetJets of the world speak to luxury buyers. These are people where the cost of the plane is a rounding error, right? It’s irrelevant to them. It’s like, ah, whether it’s 10 million or 6 million makes no difference. I would just like the newest, best, fastest, nicest, easiest. I don’t think that market needs more people serving that market. It’s pretty clear that they’re all just going to say it’s one of the top five big luxury players.

We really speak more to the fact that there’s a whole class of people that are saying, I don’t want to spend money I don’t need to spend, I want safe, so it always starts with that. I want safe. No one’s saying to me like I’m willing to take chances on my safety and my family. So, it’s got to meet the standard of safety.

And then beyond that, they say, “I need to move a certain number of people, a certain speed, or a certain distance. So, I need to move seven people six times a year from point A to point B and that’s it.” So, strip away the airplane, strip away the brand, strip away the dollars. First, you want to think about it from the perspective how you’re moving that.

So then what comes in is some people have preferences of, well, I only want to be on a jet. And a jet means literally they have jet engines, they have no propellers. It’s like an airliner or a Gulfstream or Learjet, a Challenger. The reason why people like jets are they’re generally the fastest airplanes and they’re considered to be the safest. Generally speaking, those are the most reliable. They go the farthest and so forth.

Then a step down from that, and this is really where like Wheels Up started out with King Air, these are turboprops, Pilatus PC-12, TBMs. These are airplanes that they have propellers, but they actually have a jet engine driving the propeller. That’s why it’s called a turboprop. And those, despite the fact that you’re thinking they’re little prop planes, they actually have the safety records generally of a bigger jet. And that’s the advantage. They’re more reliable, they’re a little bit faster. They’re generally pressurized, which is, again, something people don’t think about is, oh, yeah, it’d be weird to be flying around an airplane where it’s noisy and when we go up to 10,000 feet, I feel like I’m at 10,000 feet and I have to put oxygen masks on and things like that.

Then you go a class down from that and you start getting into just regular prop planes. And again, those are the ones that it’s six-seaters and four-seaters or the Cirrus, you might have seen the Cirrus. It’s the composite airplane with the parachute that you can pull. And these are very, very popular amongst entrepreneurs that want to become pilots by the way. It’s like if someone’s going to out and buy a plane and become a pilot, they get the Cirrus, their business owners, generally speaking.

So, you kind of have those three categories. And again, the thing that mostly drives people is the distance I need to go or their own personal relationship too. I just can’t fly in a prop plane. Many times we hear this driven by people is my wife or my kids, they’re afraid to get on a prop plane. And so, that becomes the first question of prop planes run anywhere from like 50 grand up to about a million bucks. Your turboprops run anywhere from about 200,000 to about 5 million. And then your jets can run anywhere from about a million to 75 million. So, it’s pretty, pretty interesting ranges that you’re playing in there.

Justin Donald: Yeah, no kidding. And it’s interesting to think about I’ve got friends that play in each of these spaces, I’ve got friends that have owned or do currently own jets in each of these categories or prop planes in each category that you just mentioned. And I’ve had the luxury of being able to fly on many different of their jets and planes, which is really fun and getting this experience. And by the way, the extreme side like you think about the nicest, pay attention to what the wealthiest people in the world or in the US are buying and you’ll get an idea of what most people consider to be the highest-end jets with the Gulfstream’s and Global Express’s and all that. And then you’ve got just your smaller little plane.

One of the things that is interesting to me to think through is the type of clients you deal with, like you must have clients in all different categories, all different walks of life, all different niches of professional jobs, experiences, but I’m curious if there’s a theme. I’m sure that you’re dealing with a lot of people that have some– let’s just call it extra money to be spending. Not everyone does, but a lot of people certainly do. Where would you say most of these people are? Like even in your company, are these pro sports teams running stuff out? Or are these just wealthy entrepreneurs? Obviously, you’re probably getting some politicians in there, bands, right? A lot of your bands that have made it are going to be flying these, chartering these. So, I’d love to hear about some of that.

Nik Tarascio: Yeah. So, I mean, being in New York, there is definitely two different styles of the private jet market, like the California market is a very different market. You get a lot of the entertainers and stand-up comedians both in New York and L.A. These are people that you think of like the Trevor Noah’s of the world, right? They got to be on a show every night, but then on the weekend, they need to go out and perform. So, you get the people like that as well. But we see a lot of people that own real estate, generally speaking, for two reasons, one, real estate marries really well to owning a jet because you have the passive income from my real estate deals, I can offset passive income with the airplane.

The second piece of it is that people that are on real estate, off and on real estate all over the place so they have reasons to go from place to place. We also see a lot of the roll-up strategies that have gone on over the last couple of years or you’ve got one big company buying up a bunch of mom-and-pop practices. We’ve had a bunch of customers that do that as well. They just do road shows and they go visit a bunch of companies, Fortune 500s that have distributed teams in manufacturing all over the place.

But then there are just the people that have just a bunch of money from their businesses or good financial investments that they’ve made that just say, “Hey, I can’t justify owning a plane outright and just paying for it.” But if I put it on a charter fleet, it’s within reason. And I can actually make it that– like you said, it’s not going to be free, it’s not going to offset at all. But it now has put it to a financial reality that I can tolerate and that I’m okay with it. So, it’s worth the trade.

We have a lot of people like that. We have a lot of people that run, oddly enough, up and down the East Coast. New York, Florida is one of the busiest routes in America. And you’ve got all walks of life. There are people that fly for business, people that fly personally, and our business serves a lot of the brokers. The majority of people that sell charter flights don’t actually have airplanes and they don’t have an airline. They just marry that need to someone who operates a plane.

Justin Donald: Yeah, that’s interesting. I’m going to give an analogy, like I think about social media, and one of the things that you see, it’s almost like you feel everyone’s doing all this cool stuff, except you are. Everyone’s doing cooler things than you’re doing. And so, I think in the world of private aviation, this is kind of it too, right? You’ve got a lot of people that they want to look the part, They want to show up in a certain way. But I think it’s important for, like I want my audience to know that a lot of people flying are not who you would think. It’s not people often that are just so wealthy, have so much money, they can blow it on whatever.

Like some of these people maybe even shouldn’t be flying privately, right? I think there’s this facade that a lot of people have or this act, this show where they kind of want to compete with the Joneses, keep up with the Joneses. And I’d love to get your perspective on this because I think if you have the means to do it, great, by all means, do it. But I also think that there’s a danger in doing it for the image and the trap that that can create. And I know there are a lot of people that fall in that trap.

Nik Tarascio: Yeah. And I don’t want to offend anyone, so I’ll be very cautious in how I say this next part. We always can tell if someone has new money or old money, generally speaking, and you can always tell if someone’s going to be blasting Instagram posts. And again, there are lots of influencers that this is part of their brand, and I get it, it’s in service of that.

But usually, we’ve had this experience. I used to fly a lot of charters. And I always knew when someone was figuring out what it meant to be wealthy when they somehow thought they had to talk down to the pilots, like, “Look how powerful I am. I get to tell these people what to do and I control their schedule.” And I’m like, that’s actually not what real wealth does. The people I’ve met that are from wealthy families are polished and respectful and they lift everyone up. They’re really low-key.

So, we generally can tell if someone’s dressing up on a private jet flight, we always joke about this actually, if someone orders a filet mignon on a jet flight, it’s amateur hour because a filet mignon is not great on a jet. A sandwich is good on a jet, but you’re taking a piece of meat that was cooked, you’re going to put it in a little oven up at altitude. It’s not the right way to do that. So, some of the truly, like family names that we all know, they’re the most low-key people – sneakers, sweat pants, just get me some subway sandwiches. It’s unbelievable when you really see that stuff. But it is a trap, and I think that there is a story. I don’t know if you ever heard of the company JetSmarter.

Justin Donald: I haven’t, no.

Nik Tarascio: So, JetSmarter was this really interesting company that basically became this darling of the space. They got valued over a billion dollars and they had this whole thing of, for $25,000 or $50,000, I don’t remember the exact number, you get as many– it’s like a Netflix subscription. If there’s an open seat, fly on one of our jets, you have access to it. You could book up to three at any given time. And then when you use one, you can book another one.

So, it was really interesting because we knew all these people that were taking credit cards, college kids were maxing out all their credit cards and saying, for $25,000, I’ve got unlimited private jet access. And so, it was a lot of this, like the facade of like, I want to show that I’m that private jet guy and I can do this. And these guys were doing it and taken dates on the planes, like, look at me, I roll big, right? It is a trap.

And I’d almost recommend for someone, if you can’t sustain this lifestyle of flying private, it doesn’t do anyone favors for you to do it, especially if you have a family. Your kids are going to expect it, your spouse is going to expect it. You’ve raised the bar for the rest of your life and they will be disappointed in first class.

Justin Donald: That in itself is such a powerful statement. And by the way, for anyone that is a parent, you know that you are constantly fighting entitlement. And by the way, you’ve got the extremes. And so, there’s this book that my wife and I recently read or I read part of, and she read the full length of it and she was sharing, she wanted me to check out this section of it, but it really talked to the dangers of parenting on the two extremes on being very affluent or being very poor and what those extremes can do and how much harder you have to combat those extremes through strong parenting than what someone maybe right in the middle, like a middle-class family would need to worry about.

And so, yeah, when you start embarking on the world of private aviation, I think we have to be careful in what we’re teaching our kids through that process because the last thing we want to do is make this seem like this is normal, that the family wealth is your wealth. There’s so much to unpack. And I often see kids that learn to talk down to people based on obviously seeing parents do it, but also being in an environment where you may see yourself above others, which is unfortunate, but I think that we’ve got to be careful in this in how we parent around.

I’ve got an audience that deeply respects and appreciates lifestyle and maybe the finer things in life. I just think we’ve got to be careful as we introduce those and the way that we describe them and expectations around them. And I’m curious to get your thoughts on that.

Nik Tarascio: Yeah. I mean, while you were talking, you brought up a memory of a friend of mine said that his kids, when they got on an airline for the first time, they were so curious about, or they were laughing about the novelty of look at all these other people on our plane. I’ve never seen other people on our plane before, right? And I’ve observed kids that grew up in that world.

I remember, I think it was a 17-year-old daughter of one of our customers walking up to the plane, and it was only a Learjet. And she was used to being on Gulfstream. And she said, “I’m not getting in something that small.” And again, no issue if that’s where you’re at, but it is that entitlement becomes a real force to keep up with. And again, I always tell people in aviation, never buy an airplane you can’t afford if whatever deal structure that needs to support it makes it possible goes away.

So, again, I’m all for reduce the cost of the airplane. But if that deal went away, if some charter deal or if some offset of some lease structure went away, could you afford the asset? Too many people are like, I’m going to take a Hail Mary hit, and if it works out, amazing, if it doesn’t, I’m screwed. And I don’t think that that’s a great way to come into this. And that’s probably the horror stories a lot of people hear, which is it’s never great to own an airplane.

I beg to differ. I think that there are many responsible ways to participate in charter on an airplane to have a fractional ownership. It’s only when someone is taking that same entrepreneurial spirit that allows them to build their business, but they’re taking it to using airplanes. I don’t think that those two things go together very well.

Justin Donald: Well, and I think there are a lot of great teaching opportunities around it as well. So, it’s not that it’s always a danger. It’s that there needs to be education around it, around what’s normal, what’s not normal, what in life is a luxury, what in life is a need, and kind of matching expectations with reality, right? Like that is so, so important. But I’ve got friends that have done it really well and I’ve got friends that haven’t.

But the friends that have done it well, they’ve been very intentional on how they’ve done it and the education around it and kind of setting it up, setting the expectation of what that looks like. So, one of the things that I would love to make sure we talk about is your podcast. You’ve got a really cool podcast about really dreams, the dream beyond. So, I’d love for you to share a little bit about that as well.

Nik Tarascio: Sure. So, growing up around these exact kind of stories that we’re talking about, I’d seen many people that were living the dream I thought. They had all the money and the nice cars. We’d park their Bentleys for them and pull their bags up to their plane and everything like that.

But often, I would look in the back of the airplane and see people that were actually not very happy. They were there as a family in the airplane, but they didn’t seem very connected and they didn’t seem very, again, joyous in this moment, which should be a celebration. We’re going somewhere fun. We’re going on a vacation or we’re going to do this exciting opportunity.

And it kind of hit me that I, too, have been chasing that dream. I’d been chasing these external validations of who I was as a person. And at some point when I hit a certain wealth level, I was like, I actually don’t think it made me feel anything, I don’t actually feel any better. If anything, I actually feel worse because I realized if that stuff doesn’t make me feel whole, then I’m a lost case. There’s nothing that will make me feel whole.

And it wasn’t until I went through that process and observed other people going through the process that I realized I think there’s something else people are actually after. And so. I started interviewing people that have gone through that early successes. In many cases, they kind of went through the dark knight of the soul when that success didn’t fulfill them. And then how did they find their way to true fulfillment?

And I think that’s really what’s– in many ways, I think I’m atoning for my sins because I sold people their first dreams. I sell people airplanes, and they get to me, like, amazing. And then they realize, oh, yeah, this is actually I feel just as I did before it. It’s like the story of people that win lotto. They thought it was going to change their life for the better, and not that long after, they’re back to the same money they had and the same level of happiness.

And I think that’s where I really wanted to be intentional about saying, “Yes, please get the jet, go and have this amazing life.” If it fits within your wealth bracket, go and do it, but also be intentional in the same way about really building that heart and building that connection, building that true fulfillment. So, I feel like I have to support both sides of the dream.

Justin Donald: Yeah, that’s well said. And the reality is material possessions are never going to fulfill us. There may be a dopamine hit for a period of time. There may be an excitement around something for a period of time, but the material thing itself isn’t going to fulfill long term. We’ve got to be careful. We’re not replacing. We’re not taking what does last and replacing it with something that doesn’t because there’s always going to be a new shiny object, a newer jet, a nicer jet, a newer car, a nicer car, a newer house, a nicer house, a second house, a third house, or whatever, like at a certain point, it feeds itself, it becomes an addiction. And we’ve got to be careful, especially as goalposts constantly move.

And I think, if we’re trying to find fulfillment in a thing, those things aren’t designed for that. Fulfillment is like relationships, people, quality time. Now, you can get some of that using these things, using your home, your jet, your– whatever it is, like you can add that too, but we’ve got to be careful that we’re not substituting out the key ingredient to fulfillment, living a life of purpose, spending time in the things that we’re most passionate about and spending time with people that we love and appreciate, and creating carefree timelessness with those people.

Nik Tarascio: That’s right. I think it’s very counter in aviation that once you fly private, you are also kind of separating yourself. There is this idea of I’ve kind of pulled myself away from the masses. And a buddy of mine, John Levy, who I interviewed on the podcast, he’s a really interesting guy that talks about the science of influence and connection. And he said, “Yes, Maslow’s hierarchy is accurate. At a base level, you want to have your food and shelter and all that stuff.” But he says, “But do you know people that have chosen not to eat to fit into a group? Because if you do, it says that sometimes belonging is actually more important than those basic survival needs.”

And I thought a lot about that. I think that is true that sometimes when we go down this road of this excessive wealth and these things like private jets, it actually becomes more of an isolation tool than a way to feel connected because now people come with their hand out, they assume things about you. They suddenly think like, well, you have the money, you have a jet. Gimme, gimme, gimme. And it becomes a transactional relationship.

So, I think it is so important for someone stepping into this world to be really intentional about cultivating meaningful connection and not using the jet as that, I’m going to show off, because now, the only reason people are talking to me is because I have a plane. And I’ve seen that happen many times over.

Justin Donald: Yeah. Great thoughts and concepts. And I just really appreciate your perspective in this space. This is so cool. I love having just an open conversation about something that I think a lot of people may never talk about. And I like giving people a glimpse of what is out there if this is the right fit for them. So, for those that are interested, either now or in the future, how can they learn more about you and more about your charter company? Where can they go?

Nik Tarascio: Sure. So, they can check out Ventura Jet, as in Ace Ventura. And you could go there. You could check out my book Own Your Own Plane: It Costs Less Than You Think on Amazon. Or you could even just find me on Instagram, niktarascio. And I’m pretty informal about this. I just like talking about airplanes, so find a way to reach out, I’m happy to chat.

Justin Donald: I love it. Well, one of the things that I love to do is end each episode with a question, a simple question for my audience. And that’s this. What’s one step that you can take today that can move you towards financial freedom and move you towards a life that is on your terms, not a life by default, but rather a life by design? Thanks so much, and we’ll catch you next week.

Nik Tarascio: Thanks for having me.

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