An Interview With Jared Isaacman

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Always one who has been unafraid to challenge the standard business model, Jared Isaacman has taken his proven approach that he developed with his successful businesses and applied it to his jet teams and the Aerospace Defense Industry’s Draken International.

Known to those in aviation circles by his callsign ‘Rook,’ Jared Isaacman is much more than a pilot. He is a husband, father, outdoor adventurist, entrepreneur, philanthropist, CEO, aviation visionary, and enthusiast. That is just what we know of.

He once said Elon Musk is putting rockets in space and taking a colony to the moon. So when it comes to the cool factor, Draken International is probably the second coolest company in the world. It is an amazing business. I couldn’t agree more.

When Jared Isaacman agreed to sit down for an in-depth conversation and share his aviation experiences, I was worried that one week would not be sufficient to prepare to address all of his accomplishments over just his sixteen years of flying.

Thank you for taking the time to participate with me in something that I believe will be a little different and will be about your accomplishments, your perspectives, and your love of aviation.

Thanks for your interest. I am always happy to talk about airplanes.

For years, I have been following your story from the beginnings that I knew of with the Heavy Metal and Black Diamond Jet Teams, onto Draken International, and now onto your newest business venture with Shift4 Payments and your own private MiG 29UB.

I want to take it back to the very beginning, if I may. In my research, I have seen a few sources attribute you to be from Allentown, Pennsylvania. However, you are really from New Jersey, are you not?

Yes, I was born in New Jersey and moved to Pennsylvania when I was about six or seven years old. My flying career almost entirely originated out of Pennsylvania, where I learned to fly at the Allentown airport going all the way back to 2004.

Looking back at your accomplishments in the world of aviation in less than 20 years, it’s quite an astonishing list. From achieving your first flight to setting multiple world records. From forming and performing with your own jet demonstration team to creating the world’s premiere Red Air adversary squadron at Draken International. And now the latest acquisition of your own personal MiG 29. I don’t know of anybody else that has come close to paralleling those types of accomplishments in our lifetime. Is this just a normal pace for you, or does this also seem like quite a list of accomplishments to you?

I’m fortunate to be able to participate in all these unique adventures and opportunities. There are many very accomplished pilots in the world, test pilots, military aviators, and civilian pilots. All of them have done everything that I’ve done. I’m fortunate that I started a business that’s found quite a bit of success over the last 20 years, which has allowed me to participate in this kind of thing. I know I’ve been fortunate, and whenever we do things like the Black Diamond Jet Team, we donated every performance to the Make-A-Wish Foundation.

The World Record flights were all to raise money for the Make-A-Wish Foundation. I definitely don’t think it’s so much as having the skills or training is as much as it is fortunate to be in this position.

Do you recall what in your lifetime sparked your love for aviation and flight?

I think it’s been there for as long as I can remember. I was probably like five years old, playing a Falcon 3.0 flight simulator on an old Atari computer that my brother built. Growing up, I went to Aviation Challenge Camp, which is like the fighter jet version of Space Camp in Huntsville, Alabama. As a kid, this has always been and part of my life.

It was back in 2004, it was still kind of the early days of my company, and I was living in the basement, working all the time and burning myself out. I was like, I have to get a hobby, I need something outside the office, and that’s why I said I’m going to take this from an interest in aviation to something I’m actually going to do. I started with five lessons, but it’s been with me my whole life.

When was your first flight lesson?

I was probably 21 at the time. As I said, I went to Aviation Challenge, where I was flying Cessna’s. When I was young, I was fortunate to get a P-51 ride, but my interest was always pretty good. I started flying lessons right here in Allentown. I took one lesson with a flight school Cessna 172, and then I hired my instructor. I bought a Cessna Turbo 182 from Textron, and I started flying right away. So, that’s where the journey began.

A few months after you bought the Cessna Turbo 182, you made quite a step up in performance and bought a Beechcraft Baron?

Yeah, if I look at my logbook, I had less than 150 hours of the single-engine piston. So, as soon as I got my private pilot license, I went right into the Baron. I got my commercial, instrument, and my multi-engine ratings in the Baron. I flew that for probably about 700 hours over a year and a half, and then I pretty much jumped to jets.

You graduated from Embry-Riddle Aeronautical University. Were you already involved with jet aircraft by then?

I think I was 27 or 28, so I had already been a pilot for some time when I went there. It was really so that I could have the option if I ever wanted to join the Air National Guard or the Air Force Reserve as a pilot I needed a College Degree.

In 2008 you made your first World Record attempt in a light jet; you and your Co-Pilot Doug Demko missed the mark by just one hour after long ground holds in India and Japan. You shattered the mark by over twenty-one hours on your second attempt, completing the route in sixty-one hours, fifty-one minutes. Do you recall your route, and did it start with the Northern Blue Spruce Route to Greenland?

We started in Morristown, New Jersey, in both attempts, and we went to Saint John’s, Canada. We actually skipped Greenland and went right to the Azores. This is where the routes started to differ between 08 and 09. I think we stopped in Madrid before hitting the Greek Islands, Luxor, and Oman. From there, we made our way to Qatar, Pakistan, and India, and this is where we had a lot of issues. Had we known, we would have chosen to go to Thailand, Brunei to Japan before Russia, and then onto Alaska, Reno, and home.

In 09, we went from a Citation Mustang to a Cessna CJ2, which is also in the same light jet weight class. However, CJ2 enabled us to eliminate many stops, specifically with Japan, India, and Pakistan. Those were all areas that we got really ground up in bureaucracy and such that slowed us down.

The Cessna in 09 allowed us still to go from Morristown, New Jersey to Canada and the Azores. However, this time we went right to Sardinia and onto Luxor. We then went to Oman and the Maldives. We went back to Thailand and could skip Brunei and go onto the Philippines. From there, we went to South Korea to Russia, and Alaska to Reno, Fargo, and home. We were able to cut out all the high-risk stops.

I imagine there is a tremendous amount of planning that goes into an around the world flight.

Yeah, because your time is being counted. So, if you get jammed up in turn order or even if the fuel trucks aren’t ready to go, that all counts against you. We had an observer from the National Aeronautic Institution on board to certify that we averaged 15 or 16 minutes on the ground at every stop. We would have two fuel trucks for either wing the moment we taxi in.

Any delay along the route could affect your next stop. All of the details, like the fuel and all of the paperwork, were handled in advance. Payments were made in advance, so as we were topping off, we were getting our flight plans clearance, taxing out, and blasting off.

You mentioned earlier about the Make-A-Wish Foundation, and I did notice that you are a Philanthropist. Is this correct that you raised over $100,000 on that World Record trip between pledges and donations?

I don’t remember the exact amount, but it was north of 100,000 dollars.

I have to compliment and thank you for all of your helping and giving back you have done for people who are in need. I have also read that you are involved in other events such as a charity poker tour and Pennies for Humanity.

I think tons of pilots from all walks of life could do everything that I’ve ever done in an airplane. I’m just lucky to be in that spot because the ball bounced my way a few times with a great business. So, whenever you undertake any adventure, it just has to be about more than just you. I always try to incorporate a good cause into any of these pictures.

In fact, I have one that’s coming up that I am really excited about. I can’t really talk about it, but in the next month and a half, there should be something interesting coming along that’s going to benefit a really worthwhile organization.

Around 2010 you struck up a friendship with Sean’ Stroker’ Gustafson. Is this who introduced you to flying military jets?

Yes, that is about the right time, but actually, I was flying ex-military aircraft from like 2008, 2009, and 2010. I was already flying the L-39 and the T-33. I got checked out in the Collings Foundation A-4 Skyhawk and took it to Oshkosh in 2010 as part of the Vietnam Heritage Flight. It was really cool that I was doing that kind of flying with Jerry’ Jive’ Kirby. He and Mike ‘Buick’ Eberhardt were my formation, aerobatic and military instructors. Both of them are really accomplished, military aviators.

Was this the beginning of the formation of the Heavy Metal Jet Team?

It was early 2010, where we said to each other; we already have a couple of L-39’s and a T-33. Why don’t we put a paint job on them and start an air show team? Then it became, why don’t we get a couple more and try to put together a Thunderbird caliber show. In the process, we just looked to the Thunderbirds for additional pilots to join our team.

We had Major Sean “Stroker” Gustafson, and then we got Major John’ Slick’ Baum, both of whom were Thunderbirds on the 2009 – 2010 teams. So, they committed to join the team right after they got out. They came right from the Thunderbirds, swapping F-16’s for L-39’s and that’s when my friendship with those two struck up.

We were getting the team off the ground and started training when Mike’ Buick’ Eberhardt came along. In there somewhere, Dale’ Snort’ Snodgrass and Jerry’ Jive’ Kirby created the Black Diamond. Buick was my instructor in the A-4 Skyhawk when I was flying the Collings Foundation bird. I was flying with ‘Buick’ two years before the air show team. He was just a natural, and when you’re building up the team, anyone you had a relationship with and can trust, we invited you to join us.

When did you start learning to do formation flying? Does it go back as far as your time with the Collings Foundation?

I learned how to fly formations before that in L-39’s and T-33’s in the 08 and 09 time period. I probably got checked out in the A-4 in late 09 when I went to Oshkosh in 2010. We took it along with the Phantom. I was flying L-39’s and T-33’s long before the A-4.

Formation flying is really a big step in complexity and performance, especially with a swept-wing jet. You definitely don’t jump right to that, at least on the civilian track. I had at least a year and a half of formation aerobatics flying the L- 39.

What is it like to fly the ‘Scooter’?

It’s an unbelievable airplane. It is a very simple airframe and design, just like an L-39. By that, I mean you wear the jet. Everybody says that it’s an incredibly tight cockpit, and you barely fit in it. It’s just like a little sports car. Heineman’s design is very simple. I’m lucky because I’ve gotten to fly the whole evolution of Skyhawks. I’ve flown all of the models with the J-65 engines, the ‘F’ models with J-50, the ‘J’ models with J-52’s, the ‘K’ model with the F-16 radar suite and HUD glass, and the ‘N’ model with the 408 motors with 20% more thrust. Those are like your rocket ships and is definitely one of my favorites to fly. The mighty scooter is still up there as a great adversary platform and definitely one of the favorites.

In the early days with the Heavy Metal Jet Team, was there ever consideration given to flying another airframe, or was the L-39 the way to go if you want to fast-track the team?

We never considered another airframe for the diamond. You need to know that you must have five aircraft if you want to have a spare aircraft. There just aren’t five of any jet warbirds in the country.

We already owned two L-39’s by the time we started building up the team, and it was a very easy decision to buy three more. There was never a doubt that the L-39 was going to be the diamond aircraft. Our solos were MiG 17’s, and we already had a T-33.

We definitely spiced it up on the solo routine because you didn’t need as many aircraft, but we never looked at anything else for the diamond operators.

I was fortunate to see the team with both the T-33 in Atlantic City, New Jersey, and the MiG 17’s at NAS Oceana VA, and I found both routines spectacular.

That Oceana Friday night show went down as far as from our perspective, as one of our best performances.

I remember the flying was perfect and the sky was just magnificent for that night show.

What do you remember about that first year with the team?

That was the greatest time of my life when we were out there on the show circuit in 2011. I certainly had the most fun I’ve ever had. A lot of fun memories, and it was a great team.

I attempted to total up all of the team’s performances in the four years you were together from 2011 to 2014. By my count, there were somewhere around 104 scheduled performances. Do you know if there is an official count?

I’ve always used the over 100 performances whenever I’ve described it, so it sounds like you’re right there. Most of the time, you get four performances per weekend. You have your practice day on a Friday arrival, and then you usually would launch again for a night show and the two-weekend shows.

I know my last show was in 2014 at Cherry Point, at least the public ones. We might have done a couple of other shows. I remember it because it was a high show, which I guess I tucked away in my memory as my last show.

I had the 2014 Lehigh Valley Air Show in Allentown, Pennsylvania, written down as your last show, but you think Cherry Point the last full show?

I recall Cherry point being the last high show we performed in May 2014. I do remember both of the Allentown shows, and I think they were both flat shows. The big issue may have been some cloud cover and that they couldn’t get their aerobatic box that was needed.

After the 2014 season, the team did some flybys for events such as the Indy 500, NFL games, and special events, but you never performed as a team again?

We did a little reunion, and it was just for us where we did the whole routine twice in June of 2016 in Lakeland, Florida.

I always wondered about the name change from the Heavy Metal Jet Team to the Black Diamond Jet Team and why it happened before the end of the air show season.

That was an internal thing where somebody went and copyrighted the name and forced the name change.

I’ve seen the list of all of the different types of aircraft you have piloted, from business jets to military aircraft but what I have never seen is the mention of a helicopter. Is there a reason for that?

Well, I think they are cool, and I’ve been a passenger in them, but I’ve never really had any interest in flying them. You just have all sorts of types of pilots, there’s a lot of fixed-wing guys that don’t want anything to do with helicopters, and there’s some that just go for the challenge. I’m probably more in the former than the latter camp. I have nothing against them. I just kind of prefer having wings and the ability to glide.

Is it true that you owned your own Saab J-35 Draken?

It is. That predated the Black Diamonds, and I got it probably in the 08 – 09 time period. I spent a couple of years trying to restore it, and then I just gave up. It’s probably on a stick somewhere, but I did keep the name for Draken international.

The Draken J-35 is just a great example of what I mean about there’s no part support. There’s no egress support for it, so you can’t upkeep the ejection seat motor. It was also like a one-off derivative of a J-79 engine, and there’s no support for it. You really are taking many unnecessary risks trying to operate those kinds of one-off platforms versus what I think is the right approach, which is how we get things done.

It seems your approach has been to bring aircraft over, take them apart, and go over them from top to bottom. In the end, when you reassemble them, you had made them safe and essentially better than they were when they were new.

No doubt, you have to because the decks were stacked against us from the start. Nobody wanted our service in the beginning.

The Air Force was like, we have T-38’s, and they do just fine. They didn’t want to certify these kinds of aircraft we were using. There were just so many issues and then the idea that it was over for us if anything went wrong.

We didn’t have a customer who was highly dependent on our service that the ATAC (Airborne Tactical Advantage Company) guys had. They had accomplished an awful lot in their time, but they certainly had setbacks where things didn’t go well. They’ve had accidents, fatalities and we had no room for error like that because we were not established.

So, the criteria we were using when selecting our aircraft was it has to be safe, sustainable, and incredible. Safe, meaning we had to be able to upkeep all the systems on it as good as it was in military service. Sustainable in that we can’t run out of parts. We have to be able to maintain a stable supply chain. Incredible, in that it’s got to be able to replicate the bad guys because if you’re just metal in the sky and you can’t shoot back, and you can’t react, then the Air Force is better off going up and fighting airliners.

That was our criteria, safe, sustainable, incredible and those are the only type of aircraft we have purchased.

How sustainable is the A-4 pipeline?

When we purchased those aircraft, and you’ll find this in every fleet we ever bought, we get more than the airplanes. We get everything that goes along with them. We had nearly 100 shipping containers from New Zealand. We had the entire New Zealand Air Forces spares and support inventory. Then we had all of the Australian Navy’s spares in support inventory as well.

At that the time we made that New Zealand A-4 deal in 2011, the Israeli Air Force, Singaporean Air Force, Brazilians, and the Argentinians were all still flying the A-4. So, we felt comfortable that other military operators in the world, on top of that huge inventory we bought, are how we ensure that they would be safe, sustainable, and incredible.

It is the same story for the Dassault F-1 Mirages we purchased.

Even the MiG-21’s we bought, even though we never operated them, there was never an issue from the supply chain perspective. We bought the MiG-21’s for such a reasonable price from Poland, and we paid like a quarter of a million dollars for thirty jets. It probably cost us another quarter of a million for shipping. They would have been great. They have been very safe, but the customer really didn’t have an interest in a MiG-21 adversary.

You donated a MiG-21 airframe to the National Naval Aviation Museum to tell the story of Desert Storm. Was this one of the spares that Draken had obtained?

We didn’t need it at the time, so ultimately, to clear space in the hangar because we needed it, we just started donating them.

Recently it has been in the news that you purchased your own MiG-29.

First off, I have to clear something up. I actually bought it like 18 months ago. I’ve never been on social media, so I recently joined up, and after flying it, I tweeted out a picture, and all this attention came along with it.

This is the former Ukrainian Air Force MiG-29 that was owned and restored by Paul Allen?

Yes, it is a MiG-29 UB model from Paul Allen’s estate.

In terms of operating the MiG-29, next to the L-39, I’d say it’s the safest, most stable fighter aircraft I’ve ever flown. You have two engines, and it’s a fourth-generation platform, so you know obviously a lot of lessons learned in fighter jet design have been incorporated into it.

I was very lucky obviously to buy it from Paul Allen’s Estate, who was a man that had a great appreciation for aviation and spared no expense with maintaining this aircraft. I couldn’t have been better positioned to be in an optimal position to learn the aircraft and operate it. It is incredibly safe; it has two engine reliability right from the start, something I have never had in any ex-military aircraft.

How do you maintain a MiG-29? Is it much different than any other jet aircraft, or is it very similar to your other aircraft?

It’s different, it is not easy, and it is not the same as other aircraft. Paul Allen had owned this aircraft for a long time before me so, and he had already trained maintenance technicians. He already established a supply chain back into Europe, so I benefited from all his groundwork.

This is not a plane that can fly 300 hours a year like an L-39. You need a team of people to launch it, and there are a lot of advanced systems. It is a fourth-generation fighter aircraft, and when things break, you’re just not going to have all the same stuff on the shelf you have with other aircraft. But you know all of that is worth it to be able to fly such an extraordinary aircraft.

I have read that John Sessions did a remarkable job of restoring it.

It’s the nicest MiG-29 in the world.

John Sessions had reported that it had a total of five hundred-seventy hours on the airframe, and only sixty of those hours were after his restoration.

Yeah, it was not many hours at all under Paul’s ownership, but everything you just said sounds correct.

The MiG-29 is capable of a top speed of Mach 2.25. Are you ever going to be able to take advantage of that?

I don’t know if it’ll get that. Many fighter jets have top speeds that the airframe can never get to unless you pointed it straight at the ground. Even the F-15 Eagle, to hit its maximum speed, they had to strip off the paint and clean off every bit of drag on it. It’s really hard to do that, but mine is in its cleanest form. There are no tanks or pylons on it. I operate it in Montana, which is often chilly, so I do have great performance. There will be opportunities, whether it’s supporting some class or student pilots.

I was reminded of the passing of Chuck Yeager this past week, and my question to you is, what is it like to fly Mach and break the sound barrier?

Very anti-climactic. I think you’d probably hear that from almost any pilot. It is not like the movie The Right Stuff. The plane isn’t shaking, and the nuts and bolts are not falling off or gauges cracking. It just happens, you don’t hear anything. It’s actually very benign in the MiG-29.

Now in the A-4 Skyhawk, even though it’s not an afterburning aircraft, you can go supersonic in it. We have done that at Draken during some research and development flights with the Department of Defense. I’ve gotten the A-4 to very high subsonic speeds. Some of our pilots did get the Skyhawk supersonic by pointing their noses down at the ground.

The A-4 has some interesting characteristics when going supersonic. Again, it’s nothing like the movie The Right Stuff, no gauges are shattering, but you will see the nose wondering as it goes through the transonic range before going supersonic. The MiG-29 exhibits none of those characteristics. It just happens.

There is word spreading around among aviation enthusiasts that you’re planning on taking your MiG-29 out to some air shows. Is that in the works?

Yeah, my day job keeps me incredibly busy at Shift4 Payments, but I hope that next year for the world to be a healthier place, and I can find the time. It won’t be anything like 45 shows, nothing like the good old days, but I definitely want to share the aircraft with other aviation enthusiasts.

Is there still an aircraft type that you still want to pilot and have not been able to as of yet?

Yes, the F-16. As I mentioned before, I was a Falcon 3.0 flight simulator kid, so I’ve always wanted to fly that jet. I would say that and the Flanker SU-27 family that shares my interest.

I will miss the L-159, that’s Draken’s primary workhorse. It looks like an L- 39, but it’s very much different. It has twice as much thrust with modern radar and an all-hydraulic control system. It is a very westernized aircraft. I actually flew the first delivery flight of the L-159 into the United States.

Not being part of Draken anymore, I’ll miss flying that airplane. Hopefully, I’ll get some opportunities again in the future. But in terms of stuff that I haven’t flown that I’d love to see happen someday, I think the F-16 and SU-27 would both be up there.

My closing question has to do with something I read that was attributed to you. Many people dream of ‘what if.’ However, your ideas don’t seem to have a glass ceiling that stops you at ‘what if.’ Is it a fair assessment that your drive to push through that based on your belief that everyone has a “useful fatigue life”?

My brother was the one who conveyed much of that. I would never have said it like that. That’s obviously over the top aviation terminology. I would have definitely said it a little bit differently because I don’t think the average person can relate to fatigue life and how many hours you have lived.

I do try and take advantage of whatever opportunities are presented to me. I believe in the concept that we only get one chance on this planet. You just want to be able to make the most of it. If you can, and I’m trying, do some good along the way. I actually very much believe that.

A very special thank you to Jared Isaacman for his time and for sharing his personal collection of photographs for this article.

All photos courtesy Jared Isaacman, except where noted.

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