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

Click here to download the podcast on Apple Podcasts

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:


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 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 history, we've grown where about one third of all the restaurants and hotels in this country use some form of Shift4 technology.

But we've always wanted to diversify from there into more everyday commerce, where everyday people could create a business and have an opportunity to thrive, and grow, and expand. You got to pull yourself out of the complex world. In order to do that, you got to put yourself into a more simplistic product.

And that's what we've created with Shift4Shop, because it enables literally anyone who has an idea for a business to create one. It doesn't cost anything to use it or create your web store. And then you put it out there to the world and you see what happens. And a lot of e-commerce businesses began just like that.

So that's what #Shift4Shop shop is. Very similar to some of the other shops that people may've heard of, that enable people to create these e-commerce businesses. But we approach it with a much different more disruptive pricing model, where we make it accessible to everyone. And we're pretty excited about it.

TJ Hoisington:

I did notice that online is that you get a lot. Even for signing up for the free version, there's a lot of benefits there, that maybe some of your competitors don't offer. Before we move onto your flying, and piloting, and so forth, what advice would you have for any person maybe graduating from high school, maybe their first couple years in college?

They want to start their own business or they want to be an entrepreneur. Do you have any core principles of success as a piece of advice to the listeners?

Jared Isaacman:

I mean, jeez, I could talk all day on that. First, I'd say, don't be too quick to get off the well-worn path, because that's giving people exposure and opportunities to learn things that they might not be familiar with, because it's easy to say, follow your passions. Follow your dreams. If you love what you do, you never work every day.

There's a lot of cliches like that and stuff too, but you don't know everything. The world has a lot to offer, right? You could wind up being one of the best at a profession that you know nothing about today. And if you depart that path early on, you may never get those opportunities.

So first, I'd say, I've met a lot of entrepreneurs who have been very successful a little bit later in their careers, after they've got a lot of experience and exposer, even a little wisdom, from just progressing on the path that, again, it's well worn, but it does work to some degree.

So I'd say, don't be too quick to jump off the track a little bit. But when you do find something that you're very passionate about, and most importantly, has real opportunity behind it, because that's also another mistake I've seen. People who have a passion for, I don't know, auto racing or something. They're going to open up an auto race modification store.

But they're putting it in the same place that there's three others. There might not be a lot of opportunity there. So not only do you have to have passion about it, but you have to know that there's something wrong, something you can fix, something that you can make better, right?

And then, I totally believe you should give it all. It should be one of your top priorities in life because starting a business is hard, and many do fail along the way. So it doesn't leave a lot opportunity for other things in your life to be a distraction, if you want to be part of the smaller percentage of the odds that actually overcome and prevail. You got to be very focused and give it everything you've got.

And then, the last thing I'd say is, really obsess over your decision making, right? One of the worst things you can do for sure is being indecisive. Not making decisions can be one of the worst decisions, right? But when you do, learn from every one of them.

Still today, I'll go back and look at emails I wrote 15 years ago, 10 years ago, to see if the decision was right, how it played out, and how it can shape my thought process going forward. And I think that's how you move from being in a top 5% in your particular category or industry or vertical.

And you continue to progress up to the top because you refined your thinking constantly. Those are just a couple things I would suggest.

TJ Hoisington:

And what I heard in the sprit of that last point is, that constant and never-ending improvement. And being able to look at the mistakes you've made, learn from them, and the successes. And what things can be pulled out of that to learn and grow in the future? Wow, that's really good. Thank you for those points. Very good. You said, I read in an interview, "I really never had a hobby outside of work. It became a 100-hour work week."

And that's why, correct me if I'm wrong, but as part of that conversation, you said, "Making a lot of money isn't enough," and so it was your childhood dream to go to space. So you ventured into becoming a pilot. Give us a little bit of that story of how that all came about. That's pretty cool.

Because you were flying fighter jets. I just find that amazing. When I read that you're flying in unison. And then your team sent me some video you flying in unison 18 inches apart. You've got to give us the overview of that.

Jared Isaacman:

Yeah, sure. It's totally true that I needed a hobby. I always had a childhood passion for aviation. I mean, when I was a kid, I was playing flight simulators on computers I built, and such. It was always there. But then, my true love and my passion immediately became the business, once you create it.

It's just like I said before, you got to really try and minimize distractions and outside interests, because odds are stacked against you right from the start. But I can think about, I was probably three or four years into the company. And you're just waking up on your keyboard every, and then you're doing it over again.

For as many successes we had, I felt like, "Geez, there has to be more in my life than just this." So I picked up flying. And I started flying in 2004, and I never slowed down. I looked for any reason to fly. It was therapeutic. If it was night, I could just go up and just chill, and look out in the sky.

And that led me very quickly to flying jets, which led me to flying ex-Military aircraft, which led to airshows. Even then, just talking about business and entrepreneurship. When we were flying airshows, that was purely a hobby event. Relatively high-risk one at that.

And it was, "How do we pivot this into something commercial? This is unique. Civilians don't fly fighter jets. There has to be some need here, some problem to solve." And it turned out there was a huge one inside the Department of Defense, which led to creating a defense aerospace business that went from, when we first started, the Air Force said, "There's no problem here for you to solve."

We thought otherwise. It became a $6 billion intuitive by the time I left the organization just a year ago. Anyway, that's just an example of, you got a passion, but you spot opportunity, and you can turn it into something commercial.

TJ Hoisington:

You are a master problem solver, it seems like. I mean, you see a problem in the marketplace, and you go, "There's probably an easier way to do this." I had that thought that you just answered, "Did the Air Force even think that they had a deficiency?"

Jared Isaacman:

No, they did not.

TJ Hoisington:

And here, you filled that because you had your eyes open. You had a passion for something. Did it just come to you late at night, or was it your team that gathered around, and as you got involved, you started to notice, "Hey, there's an opportunity here"? Is that how that came about?

Jared Isaacman:

Yeah, it was definitely a team effort for sure. I mean, you're totally brothers with everybody when you're flying airshows, because you are 18 inches apart, and you have to have immense trust, because obviously a lot can go wrong. And we had plenty of time to sit around the table and discuss this, and say, "There is an opportunity here with the Military," because just simply, you know, well, first, it's a good assumption in general that the government is not going to be very cost-effective or efficient on anything they do. It's a good starting assumption-

TJ Hoisington:

I agree. Yes.

Jared Isaacman:

And then, you look at budgetary environments and some of the [crosstalk 00:22:41].

TJ Hoisington:

Bureaucracy, yeah.

Jared Isaacman:

There was a lot there to support our position, and then you just had to take some risks. And we did. We went out and we started buying fighter jets from all over the world. But the Air Force told us, "No." I still have a copy of the letter where it said, "There is no requirement what you're trying to accomplish here." And that was in 2014.

18 months later, we had our first contract with the Air Force. 18 months thereafter, it became a $6 billion industry. So it can happen really quick once you prove it out.

TJ Hoisington:

Wow, that inspirational in and of itself. You said this in an interview, "My 6,000 jet flight hours, most of the training came down to about 6 hours of it. And those are the things you don't expect, that you need to prepare for." Give us a little bit more of a vision behind that, because I think there's a lot in that little statement.

Jared Isaacman:

Yeah, for sure. Just to give a little more context to it, people were asking me about flying the Dragon spacecraft in orbit. And it's a product of Elon Musk and SpaceX, so you know it's good technology. It's going to work. There's a lot of automation there.

But it was, "Are you prepared to manually operate it?" Or if there's an emergency or a contingency. Look, you prepare for that point .01% chance. It's the same flying an airplane. Flown 6,000 hours, and 99.9% of that time, the autopilot did what it was supposed to, and all the systems were good. And the lights were out. There's no warning.

But you do train for the possibility that something goes wrong, something unexpected. And that's not different in my normal aviation career as it will be flying in outer space. 99% of the time, everything does what it's supposed to. It's just that small percentage that you need to prepare for.

TJ Hoisington:

Okay, let me pull something out of that. So when I heard you say that, my thought was, Richard Bandler once said, "The mind likes what's the same, but it learns from what is different." So I think that, based on what you've said, there's a even bigger principle that anyone could apply, and it's this principle.

And feel free to adjust anything that I say here. But I'm thinking you can't grow inside of a comfort zone. The real learning, I think, in life happens in those anomaly situations, right? You learn from what's not normal sometimes.

And you do want to be prepared from them, and so I love the idea that you can have all these 6,000 hours of flight training and time up in the air, but really, it comes down to those 6. I think, I would imagine, that, that's where people really grow, is in the parts that aren't familiar. Any thoughts on that?

Jared Isaacman:

I agree completely. I mean, I'm actually here in Montana right now, and my kids, who are four and seven, are learning how to ski. My comment to them is, "If you continue to go down just the green circle every single time, sure, you may fall, but you're not actually growing as a skier."

And I think you can compare that to anything in business, right? If you're staying completely on the path the entire time, getting very caught up in the status quo, you're not going to grow as an individual, an entrepreneur, as a leader, because you're not challenging yourself.

So yeah, I think that, that one example on flight hours, you can probably take in a few different directors.

TJ Hoisington:

Yeah, you can. I just we say for the audience, make sure that if you're ... I imagine a lot of people are not comfortable right now, given the pandemic that we're in right now. But just generally speaking, if you feel pretty comfortable on your path, maybe you should disrupt it, right?

There are no sacred cows. Make sure that you're looking for more opportunities. Make sure that you're growing, you're educating yourself, stretching beyond who you were yesterday, to continually grow. I get the sense that's the way you think about life.

Jared Isaacman:

Yeah, and those that I admire as well. I mean, if you take Elon Musk for example, he has the most efficient rockets to put Payload in orbit. He was disruptive to the entire industry. No one can compete in the United Launch Alliance. No one else.

He didn't have to make the rockets land on ships. He didn't have to have that recovery. He probably took ... And this is just a guess. He might've had 20%, 30% into the margins. The moment he built in reusability, could've gone to 60%. He can then take the cash flows that come from that, reinvest it back into his business to build even more competitive differentiators, to build higher walls and deeper moats to make anyone else who's even thinking about encroaching on space, to have that much harder of an equal battle.

I mean, you can apply that into any number of industries, of pushing yourself and not getting comfortable, to give yourself the edge, to reinvest back, to make yourself an even bigger and stronger business.

TJ Hoisington:

Love it. Okay, give us the story about how you connected to Elon Musk. This is great because this all leads into Inspiration4, and the work that you're doing with St. Jude. So give us the beginning. I mean, was it easy? Did you just call him up? Did you have his phone number? How did that work?

Jared Isaacman:

Well, I'll avoid naming specific names in this. But I will say that I was first exposed to the commercial spaceflight industry in 2008 after I flew the world record flights. Basically, there were those in that industry who ... It was still very immature at the time.

Elon and SpaceX were still in the very early days commercial space exploration, and commercial rocket development and such. But they suspected that I might have an interest in what they were doing, and it was totally true. I was invited to go to Baikonur, Kazakhstan, to see the Soyuz go up. That was an incredible experience.

And I basically said, "Look, I'm in. Whenever the opportunity presents itself, please keep me in mind, because I know we have to solve some US responsibilities first. We've got to ensure there's this next vehicle for NASA to get to space once the shuttle retires.

"But when the timing is right, I'd love to be there as everybody works towards this broader ambition of enabling everyone to go journey among the stars, right?" Now, it took a little bit of time, and I had to knock on the door and remind them from time to time that I'm still very interested.

And just about three months ago, the opportunity did present itself. Now, what I had no idea was, is that it was going to be the first, or that it would come so soon, because this was presented to be even before NASA's Crew-1 flight. So the US had only just returned two people to space on Demo-2 when this opportunity was presented. And that was nearly 10 since the shuttle retired. So it was pretty early on, and I was all in.

Knowing that it is the first, and that it has some historical significance, then you just got to be very thoughtful about what message you want to sent to the world. And that came down to how we're picking this crew, who's going to represent this mission, and what organization should stand to benefit, like St. Jude.

TJ Hoisington:

Love it. Through the years of doing your piloting, and training, and so forth, and flying, did you always have in the back of your mind, "One day, I'm going to space"?

Jared Isaacman:

I did. To be honest, I felt like there was going to be some chance at some point, which is why, actually, when I went to Crew-1's launch at Kennedy Space Center, and I watched the four of them go up on the Falcon, and of course, I definitely said, "Some day, that's definitely going to be me on that rocket," I was also thinking about ... because we already knew this crew selection process, that we were going to find everyday people to join us.

And I was like, "Now, imagine them. They're not thinking about this at all. They're going about their lives every day. And one's a great healthcare worker and such. But in a very short period of time, a couple months from now, I'm going to be inviting three people, who never would've thought they would have a chance to go to space to take part in this epic mission."

And I was thinking about them, and what was going to go through their mind when we have that first conversation. Anyway, cool part of this-

TJ Hoisington:

No, that's way cool. That's really cool.

Speaker 3:

(singing) This fall, Inspiration4 launches as the first all-civilian mission to space. And you could be on board. Visit for your chance to go to space.

TJ Hoisington:

When you shared that you kept knocking the door, over time, checking in with Elon Musk, or the team, or whoever it was, it made me think of, in 2004, my back was against the wall. My world, business-wise, was falling apart. I had left the Tony Robbins Organization a few years earlier in the year 2000, or so forth.

And I thought, "I'm going to go out in the world, and I'm going to become what I've always dreamt of being," which is what I'm doing now. But I remember my darkest moment was 2004, when we had to move in the basement of my parents' house, and had two kids at the time.

I have four now, but two kids at the time. They were little ones. And I told my wife. She said, "Maybe you should go get a job." And is said, "You know what, honey? I think before I go get a job, I have to exhaust every idea I have for living my dream, if you will."

She says, "Well, what are you going to do?" I said, "I'm going to write a book." She says, "You're going to do what? You're going to write a book? You've never written a book before." She wrote me a four-page letter. I took the one car we had at the time, because one was repossessed back then.

And I drove down to a parking lot at a grocery store. And for two months, I typed. But I remember, at the end of those two months, sending out a three-ring binder of my book to a bunch of best-selling authors, and thought leaders, and so forth. I sent out 20 copies of my book.

And one of them happened to be a business owner for a publicly-traded company at the time. And I remember for two months, I sent it to him, and I called his assistant every day. My wife says it was like 80 times, I called, checking to see if he had read my book, what page he was on, so forth.

Long story short, through that persistence, that's when I got my breakthrough, because he called me up one day and he says, "I've read your book, and we have a big conference coming up with 15,000 people. Would love to have you come speak in front of our audience and make your book available for everybody."

I said, "Well, how many people are you going to have there?" He said, "We're going to 15,000 there. You should probably have 15,000 books." I said, "No problem. I can do that," as I was thinking, "There's no way financially I could do it." I called my brother. I said, "Can I borrow the money?"

We print 15,000 books. I went and spoke. Sold 15,000 copies. And then it was a couple of months after that, that Charlie "Tremendous" Jones called me and said, "A company needs 25,000 copies of your book." And it just took off. I look back on that time and I just think, "Persistence is the key."

You could have a dream all you want, but if you're not willing to walk on the door, if you're not willing to remind people, if you're not willing to bring value, like you've done, bring value to the marketplace, so that you're believable, right? And credible.

But I will tell you, once that book was printed and sold, almost 100,000 the first year, it just took off. My whole business took off. And it was in that painful experience that I found my voice. And I found out who I really was, through pain. Any thoughts around any of those concepts from you?

Jared Isaacman:

I have a lot of thoughts around that. I think that you learn an awful lot in those really dark moments in a person's career or their business journey. I think you can learn just ... I mean, there is so much wisdom that is built through those challenging times.

It made me think of just my mentor that I had throughout my business career. Actually, he was the CEO of MSI, the company I worked at and later acquired. And it was tough love. I know that a lot of my approach to problem solving and challenges today in business in general came from not having an awful lot come easy to me, having to fight for a lot.

My mentor had a big belief in that. He had somewhat of a street upbringing. It was like, "If you get to eat at the table, it's because you fought through a lot of other people to get there." It did help me in a lot of ways. I'm not saying I apply a lot of his thought process now to everything.

But I do wonder too when I think about today's generation of entrepreneurs and business leaders, having it maybe a little bit more of an easier path, because it's almost, from a society perspective, expected. There's a more perks and such that come earlier on in a career.

And I do wonder how that's going to impact people as they grow as leaders, and mature in business, where they haven't faced some of those dark moments that you referenced, because I do think there's so much learning that takes pla