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Billionaire JARED ISAACMAN Talks Life, Leadership, Entrepreneurship, and SpaceX Flight



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It was a privilege to interview high school dropout turned billionaire - Jared Isaacman. I am impressed with his story, humility, and confidence. In this interview, Jared and I discuss life, leadership, entrepreneurship, and the SpaceX flight later this year. Inspiration4 and SpaceX will be the first all-civilian crew to go to space EVER, with Jared will commanding the mission. Sign up today and win your chance to go to space!


[Interview Transcript: February 16, 2021]

Jared Isaacman:

What we're doing is, we're going to sit on top of a #falcon9 rocket, and it's going to take us all the way to outer space where we're in orbit, flying around the earth at 17,500 miles an hour. And we're going to stay there until we actually turn this spacecraft around and fire a rocket to slow down. And then we re-enter the earth's atmosphere. And that's very hard to do.

TJ Hoisington:

Hey there. I am super excited. Today, I have a new success interview for you on my Unleash Your Greatness Within podcast. Today, it was my privilege, and I really mean privilege, to interview Jared Isaacman.


You see, Jared has an amazing story.

Let me take you back a few years. When he was 16 years old, and he wanted to start a company. He went to his parents and says, "Mom, Dad, I'm going to start a company, and that's going to require me to quit high school." And that's exactly what he did.

So from the basement of his parents' house, he grew this company that would soon become a multi-billion-dollar company. And now, his company is listed on the New York Stock Exchange, and the name of the company is Shift4 Payments. Let me tell you, it was great to have him on the show.

And we talk about leadership. I ask him, "Hey, what's the makeup of a great leader?" I ask him, "Well, what if someone wants to start a business or become an entrepreneur? What advice do you have?" He gives several pieces of advice. I ask him, "Do you believe in luck?" And he gives his response with that as well. Just a great interview.

But the one thing that brought us together ... And by the way, let me just mention, he did go back and get his high school diploma, and also a college degree. He did say that, that was important as well. But one thing that brought us together was this whole #SpaceX and Inspiration4 mission.

And he's going to talk about that, but let me just lay it out for you. This #Inspiration4 mission is going to be pretty cool. It's the first time in history that four civilians are going to go to space and back. Not only that, they're going to go space and orbit the earth. Unbelievable.

And guess what? One thing you're going to see in this interview, is all the early decisions that Jared made that brought him to this point of meeting and Elon Musk and SpaceX, and then being chosen to be the pilot and the commander of this first full-civilian rocket that's going to go into space, and back home again.

And I tell you what, he talks about that, and also his connection with St. Jude, and wanting to do whatever he can do to eradicate childhood cancer. That's humbling in and of itself. We're going to talk in this interview about life, about success, about achievement.

If you've followed me for any length of time, you know that I get the opportunity to interview some of the highest achievers in the world. We're talking New York Times best-selling authors. We're talking thought leaders, business owners. We're talking about celebrities and professional athletes, I've had the opportunity to interview. And Jared was amazing.

Now, if you're watching this on my YouTube channel, hey, I invite you to subscribe, and also, make you click that notification bell, so that you're the first to be notified when I come out with a new success interview like this one, or a motivational message.

Also, make sure you go over to iTunes of Apple Podcasts. Type in my name, TJ Hoisington, and I humbly invite you to subscribe. Now, without any further ado, you're going to be inspired by this interview, all right? So let's jump right into it. Jared, welcome to the Unleash Your Greatness Within podcast.

Jared Isaacman:

Oh, thank you for having me. I'm very excited.

TJ Hoisington:

I am super excited. When I saw your name pop up in the news, I immediately started Googling you, and finding out all I could about you and your story. And I got to say, it's a privilege, and I truly mean that, to have you on the Unleash Your Greatness Within podcast. And I'll say for the record, your staff was amazing to work with. So I really appreciate you being here today.

Jared Isaacman:

Oh, I'm glad to hear that. Again, we love telling the Inspiration4 a story, and getting a good word out. So it's great to be able to connect with you, and share it.

TJ Hoisington:

One of the first things that I like to do with all my guests is to have them share their biography. Share a little bit of their background. If you could give our audience, as we have all types of different listeners, but a lot of entrepreneurs. We have a lot of business owners, leaders, and so forth. It'd be great to hear the early years. Would you give us some of your story, please?

Jared Isaacman:

Sure. First, my parents are completely responsible for this. There is a huge age gap between myself and my older brothers and sisters. So my older brother is 15 years older than me. My sister is 12 years older than me. My other brother is 10 years older than me.

So I came along a little bit later in life. By the time I'm in middle school, I'm watching them at college or beginning their careers. And I was saying, "How do I accelerate this timeline a little bit?" I guess, in high school, raising your hand to get permission to go to the bathroom or something, none of those really, I think, fit with me.

And I wanted to get out and start experiencing the world a little bit earlier in life, just the way that my older brothers and sister was doing things. So I left high school when I was 16 years old to start a company in my parents' basement.

I had some exposure to this payments industry from a part-time just that I had just prior to that. And I worked there for about six months and saw a lot of opportunity within the world of payments. Maybe just to expand on that a little bit.

TJ Hoisington:

Yeah, do.

Jared Isaacman:

1999 to 2000, if you're a consumer and you wanted a credit card to go spend, that's no problem. It shows up in your mailbox in like a week. But if you were a business, say you're a pizza place and you just want to accept credit cards, the paperwork process to do that was comparable to getting a commercial mortgage.

It was just ridiculous. There was no efficiency, no optimization. So this was the opportunity I saw early on in life. Great basement startup story. Lived in the basement. In fact, that was all I did for like three years, and was actually getting a little bit burnt out.

I needed a hobby. I needed something else in my life. That's where I picked up my childhood passion for aviation. I started flying in 2004. I just sprinted at it. I went right to jets. Ex-Military aircraft airshows and such. And built up ... went on a number of really great adventures for sure. And I've had aviation and my company has been pretty much my entire adult life.

TJ Hoisington:

No, that's really great. It's been amazing to watch some of the things you've done in the aviation world. Just unbelievable. We'll talk about that in a second. But digging into your backstory just a little bit. You're looking up to your brothers and ... One sister? Two-

Jared Isaacman:

One sister.

TJ Hoisington:

One sister. And you're seeing their life progress. And then you get this idea that life is maybe moving too slow for you and some of your dreams, so you step out. I did read this, I think, on CNBC or somewhere, that you were working at an old company called CompUSA.

Is that six-month tenure that you had? Was that it? I mean, I guess what I'm really getting at is, where did you discover that there was a problem in the [crosstalk 00:08:05]?


Jared Isaacman:

Yeah, I gave you the abridged version. I mean, to expand on it a little bit more, when I was in high school, myself and another friend of mine, Brendan Lauber, we created a teenager computer business. We called it Deco Systems. And we were just doing web design and basic computer work.

So I worked at CompUSA, which is a big computer retailer at the time. I think they've since gone out of business. And what I did was, I basically poached customers. I did my job selling what I was supposed to, computers and such. But if somebody came in and said they had an issue that I thought I could be helpful with outside of work hours, I did that.

And one of the customers who came in was from a company called MSI (Merchant Services, Inc.). MSI did early years credit card processing. They enabled businesses to accept credit cards as a form of payment. I did what I was doing, which was, I proposed that I would be able to help them.

And I wound up working there a little bit on the side, and solved their problems. And then they offered me a job, and I worked there for six months. I left high school. I got my GED. Later on, I got my college degree, so I still believe [crosstalk 00:09:13].

TJ Hoisington:

I was going to ask you about that. Okay, you did.

Jared Isaacman:

I still believe in the track. I think it does work. But anyway, I worked at that company, MSI, for six months. And then that's when I eventually left and said, "There's probably a better way to do it," and created my company.

TJ Hoisington:

Well, unbelievable. And MSI, they went on to be bought by UPS, I think I read, or something like that.

Jared Isaacman:

Actually, we acquired them in 2014, so it came back full circle.

TJ Hoisington:

Oh, you're kidding.

Jared Isaacman:

Nope.

TJ Hoisington:

Oh, isn't that wild? That's awesome. So here you are, a 16 year old in your basement with a good friend of yours. You build this company. You're working at a company and you're poaching customers. You're at least doing ... I imagine your nature is to do a good job working.

But as you were working with customers, you started to find this deficiency in the marketplace. And it was from there that led to merchant services and so forth that got you off the ground, right? I mean, it's just pretty cool. What I see in that is, from an early age, you were an entrepreneur.

You were always looking for that opening somewhere, and I just think it's amazing that you saw this. As you were doing transactions, you saw this little problem or difficulty that was going on, and you thought you could streamline it. I think that's amazing story.

Jared Isaacman:

Yeah. Look, I think there is an element of luck to it also, right? I think the ball certainly bounced my way a couple times over the years. If that person from MSI didn't come into CompUSA that day with a problem, I might never have been able to identify the opportunities that existed within the industry, and never would've been able to create a great company to support it. So definitely have been very fortunate in my career.

TJ Hoisington:

What would you say ... Maybe I'm putting you on the spot a little bit, but how would you define luck?

Jared Isaacman:

Well, I think you have to be prepared for the opportunities that are presented to you in life, right? And just hope that you are well-prepared to capitalize on when it happens. I mean, there is a degree of randomness, right? I mean, there are things that happen every single day.

And if you're in the right place at the right time, and well-prepared, you can capitalize on them, or benefit, which I certainly did throughout my career, on more than one occasion, right? I do often reflect back on a lot of things that have happened throughout my career, and decisions I've made, and opportunities that have been presented.

And I know some of them, myself and my team helped create those opportunities. And some of them, you're just in the right place at the right time, and you have to be fortunate for that when it comes around.

TJ Hoisington:

I love that. My daughter was asking, as I was taking her to practice for her school, she was asking, "Could you ask him, was he ... " what did she say? Were you a tech genius, or were you more of a visionary, would you say?

Jared Isaacman:

Oh, I certainly wouldn't try and categorize myself as a genius. I think I try and apply a lot of critical thinking to problems that I see, and challenge, is there a better way to do it? One of the differences I've seen between entrepreneurs that have been successful in their career, versus those that aren't, is the willingness to challenge conventional thinking, or accepting that things are just going to have to be a certain way forever, because that's the way they always have been.

Those who trick themselves into believing that's the way it is, sometimes it's like the can't-do type of attitude. They have a harder time progressing in their careers, I think, versus seeing problems for what they are, or accepting, or looking at inefficiencies and saying that there's a better way to do it.

That's the approach I've tried to take throughout my career, and I think it's worked really well for me in the early days of the business. And now, as the problems that we try and conquer and solve are much, much grander than our basement days, you're still trying to apply the same type of critical thinking and way to work through those issues.

TJ Hoisington:

Huge. I mean, to that you were 16 years old. If I get the numbers wrong, please correct me. But you built a $200 billion company, Shift4 Payments. You now have a new product unveiled called www.Shift4Shop.com. And what is that? Would you mind telling the audience what that is?

Jared Isaacman:

Yeah, sure. Throughout our history, we've tried to focus on, as a payments company, the more complex end of the spectrum. And what I refer to that spectrum, say, most people are familiar with Square or PayPal. And they excel in the most extreme simplistic end of the payment spectrum, coffee shops, and food trucks, and such, where there's not a lot of commerce-enabling software going on.

Well, throughout our 21-year history, we've gravitated towards the other end of the spectrum, where everything is super complicated. So our customers are Hyatt, or Caesars Palace, or pretty much every major ski resort you could think of, where there's a lot of things going on.

Pebble Beach, for example, you've got three hotels, three spas, three golf courses. They all have to integrate and sync together. That's complicated stuff. As a result, throughout our hi