Sep 12, 2022 • Podcast

What’s it like to sell private jets? With Carter Alexander

Paul discusses the unique and complicated aspects of multi-million dollar sales with Carter Alexander of Aviation Commerce and Shared Sky.

Show Notes

The process may be different, but it’s still about relationships.

“The most time-consuming aspect of it is just getting past the layers and getting to the decision maker. Because guys that are at that level of stature make pretty quick decisions and they can live with those decisions pretty readily.” Carter Alexander

Attitude drives behavior. Have the faith that you will get the deal done.

Acknowledging the small wins will help you stay focused on those long sales cycles.

Find out more about what Carter Alexander does at and

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What’s it like to sell private jets? With Carter Alexander

(Transcribed from podcast interview)

“So we ended up landing on an airstrip in the middle of Bosnia. And we thought it was an abandoned air strip, but it was surrounded by military tanks. This was supposed to be touch and go. And we ended up having to stop for, it wasn’t a long time, but maybe a couple of minutes, but it felt like a half hour to me. And I could just feel the military might closing in on me. And I walked up to the cockpit and I gold the pilot, I said, “Hey, now or never, man. You gotta take off. We gotta get outta here.” Carter Alexander

Paul: Well, have you ever looked at a product or a service or something cool, and you’re wondering, “Gosh, I wonder who sells that?” Well, I constantly ask myself that question. And the other day, I was out here at our office, and we have a private airport right by here, and I’m seeing all these private jets fly over and I wonder, what’s it like to sell that product. And so sure enough, I looked in my Rolodex and I came across my friend, Carter Alexander, and his company. And I thought of it. I thought, wow. It would be great to have him on the podcast and talk about what it’s like to sell private jets.

So—give you a little background. So, Carter, he’s the CEO of Shared Sky and he’s brokering deals, working on private charters. Really, he’s a global aviation executive. And on today’s episode, he’s going to share some of his stories. He’s going to share what it’s like to sell to super-high-net-worth individuals. What’s interesting from this conversation is really understanding how similar sales really is, whether you’re selling a product or service, or you’re selling a Boeing 747. Carter’s going to share his insights. He’s also going to share a really interesting story right at the end. So I hope you enjoy this interview as much as I did.

Just a reminder, make sure you pick up your copy of Selling Through Tough Times. Even though we are in a recession, you might not be able to buy a private jet, but you can certainly buy a book—a book that’s going to help you go out there and sell more profitably and build mental resilience. So pick up your copy of Selling Through Tough Times, wherever you get your books. On to the show.

Paul: Hello, everyone. Welcome to another episode of The Q and A Sales Podcast. So I was speaking with my buddy, Carter Alexander, here several months ago, may have been over a year ago at this point, and I learned about his business—you know, selling private jets, leasing them, charter flights, things like that. And I thought, man, airplanes are just so cool. You know, Carter, I’m the guy that still is amazed to watch a plane go up in the air and then land perfectly. So, we have my friend, Carter Alexander, joining us today to talk about selling airplanes. Carter, welcome to the show, man.

Carter: Thank you for having me, Paul. It is a long time in the making. I think it has been over a year since we’ve been circling the state, but I’m happy to be here.

Paul: Absolutely. Yeah. So what’s interesting—and I got several questions just because I’m so curious about your industry, about what you do—but let’s give a little background just for The Q and A Sales Podcast community. Again, this is going to be reaching 90+ countries, and I know you’re in international business as well, but maybe just share with The Q and A community here, what you do and a little bit about your business.

Carter: Sure. Well, I grew up in Southern California. I moved to the St Louis area in the summer of 2017. I brought the business with me. In between California and St. Louis, I lived in the Middle East in a country called Bahrain. And worked, lived in Bahrain. My office was in Khobar, Saudi Arabia, but really worked internationally all over the world, traveling, 40, 50 weeks a year. It was it was quite substantial, especially before I met my wife.

I founded my first company in the Middle East, Aviation Commerce and Capital in Dubai. Aviation Commerce and Capital is a full-service aviation advisory: buy airplanes, refit airplanes, resell airplanes. We arrange leases. We arrange financing for customers. It’ss anybody that’s interested in owning or selling a private jet. We’re a one-stop shop for that.

I also have a secondary company which kind of arose out of the pandemic and a bit of boredom, because there was not a whole lot of activity in the buy-sell market for the first six months of the pandemic, and that company is called Shared Sky Private Jet Charter. And we arrange private charters for individuals, corporations, sports teams—really whoever’s looking for one. And as an added benefit to using us, we offset all of our carbon emissions for the client. So it’s a completely carbon neutral jet charter company.

Paul: Okay. Nice. A lot going on there, especially you mentioned in Saudi Arabia. I’d love to hear more about that and what that was like, but also, most people during the pandemic, they’re sitting around, they’re growing beards, they’re growing their hair out, and you’re starting a new company. I can’t think of—. What an opportune time though. I mean, you think about how travel has changed immensely. And not only that, but you think about some of your clientele: executives, corporations as well, looking to supplement their current travel plans and offer a different option. Unbelievable. All right. Love it. Love it.

Okay. So, I am curious—how did you get into this industry? I mean, are you a pilot by chance, or do you have your aviation’s license? What was it about jets that you’re like, “Okay. I, kind of want to do this”?

Carter: Yeah, not a pilot. I don’t have an aviation background at all. When I was living in the Middle East, I was working for an extremely wealthy Arab family, handling most of their offshore business, and part of my mandate included managing the commercial aspects and the contracts for their fleet of jets. And they had Boeing business jets, Airbus, corporate jets, Falcon, Gulfstream, you know, you name it. So I just kind of stumbled into the industry that way. I took a very quick liking into it. Met everybody in the industry working for that family. And when my wife and I were talking about ending our run overseas—and you know, I was kind of looking for phase two of my career—I decided to start this company. And I have some partners in Switzerland, AMAC Aerospace, who helped me with the getting it up and running and getting the refit operation.

Yeah, so really that’s just kind of how I came into it. I stumbled into it. My grandfather did work for Northrop and he was one of the lead engineers on the B2 Bomber, but that’s really the only background I have in aviation. I’m a deal maker at heart. I love complicated transactions. I love complicated deals. I love not being able to see the finish line, but getting there eventually. So that’s just kind of the nature of the industry, and that’s how I fell in love with it.

Paul: Man. That’s great. And that is something we’ve got to talk about is some of the size deals, you know, because I think about the wide range of folks we have listening to the podcast. We’ve got people selling multi-million dollar software packages, people selling tools and fasteners, selling online subscriptions. We’ve got a very large diverse group of salespeople.

So, in preparation for this, I was letting my mind run wild about, okay, I’ve got to understand this industry. And I’m sure you’ve got some cool, crazy, just absolutely wild stories from your experience in the industry. Would you be willing to share some of your favorite experiences or some of the coolest things you’ve seen just being in the industry? (Carter: Sure, sure.) And we can blot out any names.

Carter: No, I’ll protect the names of the guilty. The private aviation industry is pretty, pretty wide ranging and pretty varied. So you have everything from your single piston Cessnas that are crop dusting, or flying flags over stadiums, all the way up to your fully kitted-out BBIP, you know, triple sevens, or 747s or 787s—just the biggest jets you can imagine. I tend towards that higher scale, just because I find the market to be less saturated up there. So in that market, you rub shoulders with some fairly influential and some fairly wealthy people. So I thought of a couple of stories that might be of interest to people.

When I was very new to the industry, I was taking delivery of a brand new, A3 2200 from Airbus in Toulouse, and it’s kind of a complicated transaction. You know, you’re working for a Saudi family. The planes registered in Cayman, the aircraft’s built in France. You know, you have taxation issues, etc. So the way that the process works is that once you take delivery of the aircraft from Airbus, you immediately have to leave the EU and wait for your tax permit to be filed.

So I was with my former boss’s brother-in-law, (inaudible), and we were in Toulouse, and we’re having some drinks celebrating the closing of this deal. And I said, “Well, where are we going to take the plane? You know, you do this all the time. This is new to me.”

And he said, “Well, have you ever been to Morocco?”

And I said, “No, I’ve never been to Morocco.”

He said, “Well, why don’t we go to Tangier?”

So we take this brand new Airbus 320, it’s just me and (inaudible) on an aircraft that’s supposed to seat 180 people, with a full flight crew and two pilots. And we land and we get escorted off by the VIP reception, and they take our passports and dah dah dah. It’s great. Spend a couple of days in Tangier and, you know, one morning I wake up and I’m texting (inaudible), “Where are you? Let’s meet for breakfast.”

He said, “Oh, I left for Casa Blanca last night.”

I’m like, “Okay, well, I guess, I guess I’ll head home too.”

So, I get a flight booked back to Bahrain. And as I’m going through customs at the airport, I get pulled aside and they said, “Well, you forgot something. We have something for you.”

And I said, “And what on earth could it be?”

So I’m standing there waiting. I’m waiting about 45 minutes. And they come back and they say, “It says here that you’ve left an Airbus that you’re supposed to take with you?”

And I said, “The airplane? I’m supposed to take that with me? I’m not a pilot. The crew was supposed to take that when they leave.”

So, you know, it was much more paperwork to fill out, and I basically got to sign my life away, but they wanted me to take the plane with me. And obviously I couldn’t do that. That was an eye-opening introduction to the world of super-high-end private aviation—that you can be solely responsible for an 80 million dollar aircraft.

Paul: Oh, that’s hilarious. I mean, I’ve left the airport and I realized, oh, I left my baggage at the baggage claim on accident, and we’re talking about an 80 million dollar airplane. That’s unbelievable. Unbelievable.

I’m very curious again, just about everything in your industry. I think about a traditional selling role, where I’m training salespeople to find opportunities, build relationships, understand the client’s needs, and then how to persuade them to partner with you and adopt your solution. What’s it like brokering and selling these deals in your industry? I mean, is the process all that much different, or is it just at a more of a unique environment in the sense that you’re trying to understand a higher level of needs and what’s important? Do you feel like the process is all that different?

Carter: Well, I feel like the process is may be a bit more complicated than a normal sales deal would be. But, at the end of the day, it’s relationships, right? As long as you have the relationships in place, and you’re good at working those relationships, and you let the experts do what they need to do, it’s fairly simple.

When you’re doing a multi-national, multi-jurisdictional, hundreds-of-millions-of-dollars aviation transaction, you have lawyers on both sides. You have bankers on both sides. You have an airworthiness authority that you need to deal with. You have the taxing authority and whatever jurisdiction that the aircraft is going to be purchased in, where it’s going to be based.

You know, when you’re dealing with people as high up as I was dealing, you also have several levels of middlemen that you need to get through in order to get to the decision maker. So I would say that’s probably the most time-consuming aspect of it is just getting past the layers and getting to the decision maker. Because guys that are at that level of stature make pretty quick decisions and they can live with those decisions pretty readily. So once they say yes or no, it’s just moving and acting on that. It’s just getting through the process, getting that yes or no, and getting all the pieces in line which are pretty time consuming.

And a deal cycle for an airplane, it might be, might be two years, especially if there’s a refit being done. Nobody’s going to pay the full price for the aircraft until it’s completely finished. So you’re working these relationships and you’re working these deals for years. And some of the people you become friends with, and some of the people you say I’m never doing a deal with that guy ever again, you know, just because of their behaviors. You know, but at the end of the day, I think it’s, fairly similar to most sales deals being that relationships are the key—maybe a little bit more complicated—but, as long as you have the right team in place, even the most complicated transactions can be fairly simple.

Paul: You know, that aspect you mentioned of just lawyers, bankers, the tax authorities, different regulations at play, all of that complicates things, but that creates an opportunity for you to bring more value. Where you, let’s say have an ultra-high-net-worth individual who says, “Okay, yeah, I want to get a 737, or I want to get an Airbus or a 747, whatever it may be. They want the outcome, and then they rely on their team to help make it happen and partnership with you, to navigate those different complicated features of the deal.

Carter: No, that’s exactly right.

Paul: You know, what’s interesting? In Value-Added Selling, we talk a lot about small wins. I have to believe that when you’re working on a two-year deal, that is highly complex in some ways, do you shrink your time horizon a little bit as the salesperson and say, “Okay, let’s just focus on that next best step.” Let’s get through that and keep inching your way closer to that deal? Is that how you stay focused during these deals?

Carter: You know, it’s not the most technologically advanced way to do it, but I literally sit down and I write, or I type out a list. It’s a checklist of everything that needs to be done in order for the deal to close. And I just go through and I start checking it off. And as more I see things checked off, I know the closer I’m getting, you know, to the deal being done. And I write down everything, even something as minute as arranging the casualty insurance for the aircraft, which is fairly simple—it’s a phone call to Willis, who we use for our insurance needs.

But, you know, even writing that down and making sure that paperwork’s lined up all the way up to signing the closing document and transferring the deed and signing the mortgage for the aircraft, all that stuff. I just write a list and I work the list. And once the list is complete, the deal’s done.

Paul: Awesome. I love it. I’d be remiss not to ask. It sounds like you’ve met with a lot of the big players very early on in your career. You got to know the industry in that way. I’m sure you’ve had some great mentors throughout your career in this. Was there some sales advice or just business advice in general that you received early on in your career that you’ve stuck with that have really been helpful for you?

Carter: You know, I have had a lot of really talented and qualified and, just, bright mentors. I would say the best one being my father. He is always giving me just the absolute best advice. His wasn’t really sales oriented, it was more just kind of deal oriented. I would say the best sales advice that I ever got was from, actually, from a lawyer that I was working with at a firm in London. And you know, what he said was, “You know, it doesn’t matter how deep into the weeds you think something is,” he said, “a deal can turn on a dime one way or another. So just keep the faith. And if you have the faith and if you have the right tools in place, you can get to the finish line. It doesn’t matter how far away it seems, but you can get there so keep the faith and keep working the process.”

Paul: Love it. Attitude drives behavior. Having that faith, that belief, that is critical. Well said. Now you may have already mentioned at this point, you’ve mentioned several countries already, but as a global executive like this, what’s the coolest place you’ve ever been, as far as traveling, that perhaps you visit on a regular basis or that just blew your mind the first time you went there?

Carter: You know, I’ve been to a lot of cool places. I’ve spent quite a bit of time in Malta, which is a great ancient country in the middle of the Mediterranean. It’s just such a significant island from a historical perspective and cultural perspective. Armies have launched wars from there, going all the way back to the Roman times. And the British used it for their offensives during the first couple of World Wars. I really fell in love with Cayman Islands immediately upon going there. So much so to the fact that my wife and I got married there and we were actually there last month for our 10 year anniversary. So that’s always a place I keep coming back to.

I mean, city-wise, it may sound generic, but Geneva is just the city that I’m in love with. It’s gorgeous, it’s multicultural, extremely expensive, but once you get past that aspect of it, it’s a very nice place to visit. Yeah, I mean, I just love traveling, and I’ve traveled so much and I’ve enjoyed everywhere that I went.

Probably the most unique place that I went was, we were selling an Airbus to a gentleman from a country that’s been in the news a lot. And because we were selling it to him and because it didn’t have all the necessary permits yet, we had to think of the country that we could bring it to which wouldn’t trigger any of any authorities. So we ended up landing on an airstrip in the middle of Bosnia. And we thought it was an abandoned air strip, but it was surrounded by military tanks. This was supposed to be touch and go. And we ended up having to stop for, it wasn’t a long time, but maybe a couple of minutes, but it felt like a half hour to me. And I could just feel the military might closing in on me. And I walked up to the cockpit and I gold the pilot, I said, “Hey, now or never, man. You gotta take off. We gotta get outta here.” (Paul: Oh, wow.) That was an interesting little day trip that we took from Basel Switzerland to Bosnia.

Paul: I almost feel like you could make a movie out of that somehow. Oh, I’d love to hear more about that. We’ll have to do it over cocktails next time we’re on the golf course. But man, you know, one of the things wanted to just finish up with here. You know, you gave us some great thoughts. It’s great to hear the just sound principles of selling, they really are able to carry over into just multiple industries, no matter how complex the sale is. So, thanks for sharing your thoughts on that today. Thanks for sharing some of your stories on what it’s like in the industry.

I’d be remiss not to ask how people can get in touch with you and your company. I know we’ve got a broad range of executives and folks listening to the show, so, where can they go to learn more about what you do.

Carter: Sure. So the website for aviation commerce and is simply It just has some very high-level information about the company and what we do. But I would encourage anybody that’s interested in that aspect of what we do to just out to me directly. I’m happy to exchange emails, or even take a phone call. The contact information is on the website,

As far as the charter business goes, you can find that at And on that website, you can search and book any of your charter needs. But again, if you have any questions regarding that, or just private aviation in general, I’m happy to discuss with anybody.

Paul: Awesome. Carter, well, thanks again for being on the show today.

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