Entrepreneurial Leverage: How Jason Schappert Turned Passion into Profit
19 Nov 2025 · 48 min
Jason Schappert built an aviation training YouTube channel into a multimillion-dollar business, then sold it and launched Moolah, an AI platform for personal finance. He emphasizes owning your customer data, preparing financials early for a potential exit, and using AI to scale personalized guidance.
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In my mind, I thought I was selling to someone who was. They were gonna be an airline pilot. You know who I talked to? I talked to the dad who it was his dream to learn to fly, but he just had to put the kids through college. So his dream took a back seat. And now it's his turn. Now it's his turn to pursue his dreams. My channel was deleted by these hackers. All subscribers lost, all views, lost everything. Completely lost. And that's when it dawned on me. I had no email, email list, I had no phone numbers, I had no way to get. My only method of marketing was organic YouTube. And I lost everything. What is the one thing that's going to have the greatest impact to my most important KPI?
Good day everybody and welcome to the Wealthy Entrepreneur Podcast. I am your host, Bob Govreau. It is a pleasure to have you join us today and I've got a very special guest that we're going to get to in a minute to share his story and some really valuable insights about entrepreneurship, exiting, scaling, and maybe even some of the future of technology and how it can be adapted into our own business. But I want to remind you before we get started that this is the place where we dissect the elements that contribute to entrepreneurial success, from mindset and leadership to profits and revenue. This specific episode we're gonna re, we're gonna call from startup to sellable, building and exiting a business for maximum value. And our guest is Jason Schappert. Now I wanna give you a little bit of a background about Jason, but he's gonna share with you his story, which you're gonna pick up on this immediately. But Jason is a serial entrepreneur and a financial technology visionary dedicated to empowering individuals to achieve financial freedom. He's the co founder of Moolah, an AI driven investment platform that simplifies complex financial concepts and provides personal insights and recommendations to help users make informed investment decisions. I know for me I'm going to be checking out Moolah and learning a little bit more Jason and he's going to share a little bit more about this, but he gives away a lot of free content to help people understand their personal finances component of their lives and of their, you know, to support their business and makes maybe the investment side of things in everyone's life a little bit easier. So guys, I'm going to just go right ahead and I'm going to bring Jason in and so let's kick this off. Welcome Jason Schappert to the Wealthy Entrepreneur Podcast. Okay guys, so I'm excited to welcome Jason in here. And before Jason, I get you sharing some of your story. I wanna say, you know, from start to finish, it seems like you've explored so many different areas of entrepreneurship, including, you know, the startup phase, the. The exit phase, the. The private equity, venture capital. It sounds like you've got that I know are super valuable to any entrepreneur who's out there. So, Jason, I would love to invite you to maybe share your story all the way back to the beginning of how you got started and where you are today.
Bob, really excited and thankful for the opportunity. And a lot of what you said, you kind of stumble into it in entrepreneurship at the end of the day. I initially just kind of made myself a job at the very beginning. And even I, you know, you hear about, write your business plan, do all this stuff, and even I didn't have all the vision of where we actually ended up sometimes. And that's how business works ultimately, sometimes. But the story goes way back, like, having a job was never really an option. I grew up in an entrepreneurial family. My parents still to this day have a pest control business killing bugs. So I was actually born in Maryland. And again, this is how my parents entrepreneurial mind think. They weren't making money in the winter because there's no bugs to kill. You know what winter is? You really know what winter is like.
I know, unfortunately.
Yes, exactly. So my parents literally said, where can we move that we can kill bugs year round? So we moved to Florida. And no joke, that is how we ended up in Florida is we moved for the bugs. So that is like the. That is the scrappy family I came from. It's like, hey, let's pack up the family. We, we're moving to Florida for bugs. Like, that's where all this came about. Now, at the same time, growing up in my father's business, I learned so much. And to see a husband and a wife do business together was really unique. But my dad said something very profound. He said, hey, the bug business is not for you. Like, you are called to bigger things. I'm not gonna give you this business one day. Like, this is my business. You need to go figure your own thing out. You can work here, but. But this bug business is too small for you. I thought, wow. I mean, and in your mind, you're a kid. Like, you idolize your parents, right? So for my dad, I thought the bug business was like the creme de la creme.
The be all and end all.
Yeah, Right. So to have your dad Say, hey, this isn't for you was very profound. And I grew such an interest in aviation. You know, the kind of kid airplane flies over. You're looking at it, you can identify it. Like I was that nerdy kid. But aviation and still, unfortunately, even to this day, has like this country club type vibe. Like if you're not a member, it's kind of hard to get into. It's expensive. You gotta speak the right language, know all their acronyms. Everything else, I didn't know how to break into it. And back to dad, he said, listen, I have a customer who I see all these airplane books and airplane models, I'll ask him. Well, it turns out the guy was a flight instructor. And he said, hey, if you do my pest control service for free this month, I'll take your son flying. And that's all it really took. So I got started in that and just jumping forward to get in the business aspect of things. I'm now 18 years old, let's say I'm a flight instructor at this point. And capitalism really hit for me the very first time when I walked into the flight school owner's office and said, hey, I'm an instructor now. I'd love to finally work here. I've done all my training, like four years of training at this school. I'm thinking, I'm finally ready to work for you and be an instructor for you. He said, jason, that's so great. We're going to pay you 11 bucks an hour. And that's when everything kind of clicked. I said, wait a second, for four years I've been paying you $25 an hour for an instructor. You sit in your air conditioned office all day. And while I'm out there in Florida in August, sweating in these 1970s airplanes, thinking, I'm on the wrong side of this deal. And again, that's when entrepreneurship and capitalism, everything really clicked. For me to say, wait a second, how do I get his job right? How do I get to do what he did? And I began just diving into all the same books you've read, right? Jim Rohn, Tony Robbins, Zig Ziglar, John Mack, all these different thought leadership, Les Brown. And they're all saying the same thing. You've got to get leverage in your business. Thinking, how do I get leverage in my business? It's like, I'm a dude.
Do I even have a business?
Do I even have a business? Yeah, you're exactly right. I've got to sit in an airplane with people. Like that's not leverage. I Guess leverage means I need to start a flight school. I need to have airplanes and insurance. I'll just see liability and fuel and everything else.
It's scary.
And it was very interesting about this time. Living in Florida, you go to the beach every weekend. And this is 16, 17 years ago now. And I saw these surfers and they had these cameras on their, on their surfboards. I said, what are those things? So These are called GoPros. They're like indestructible, they're waterproof, they're smash proof, they're all these things. I said, whoa, I bet I could put these on my airplane. So I took like the last $500 I have, I bought two Hero One GoPros. Like, remember the original GoPro with the plastic housing? They're ugly, right? And I put them on.
But innovative.
But innovative is right. And I put them on, on an airplane. And I said, you know what, there's this thing called YouTube, right? Like, and again, 17 years ago, YouTube wasn't owned by Google yet. There's no advertising, there's no really monetization. I said, I'm going to film a flight lesson and I'm going to put it on this YouTube thing. And the first video gets 12 views and the next one gets 24 views. And it kind of grows from there. And it got me thinking, wow. Traditionally, ground school was taught in person. Every Wednesday night, you'd come to the airport, you'd listen to Jason talk two hours and then we'd go, you know, fly. During that week, I thought, wow, what if I could take everything I'm teaching on the ground, plus what I ultimately teach in the air, film it and put it behind a paywall and charge for it? I said, that is the leverage in the business. When the business grows beyond Jason, when you're just a guy, when you're just a flight instructor and you can't be in every airplane everywhere, all days, when good weather, bad weather, what if I can make these courses and sell them that way? And that's really where the whole idea came from, was from a divine day at the beach where you just see these cameras and go, there's an idea here. I think many businesses start that way. I didn't have the four page business plan. I'm a college dropout, by the way. Like, I didn't have all the structure. I just had an idea.
Yeah, pretty, pretty impressive. And you know what, it's one of those things. Ever since I've been a kid, I've wanted to get into aviation. So Like, I'm getting. My heart rate's getting up little bit here. I'm like, oh, damn, I got to go watch these courses now. I got to find this business. Check it out. But I remember when I was a kid, I always had a dream of flying a helicopter and getting my helicopter pilot's license. And, you know, as I'm in my 40s now, talking to my wife, I'm like, you know, I am going to get my pilot's license here at some point. And she's like, oh, like, you know, I'm never getting in a plane with you, right? Like, why? Why not? Yeah, so we heard that a lot. She'd get in. Yeah, she'd get in. The kids would anyway. But super cool. It's super interesting. And, you know, you're exactly right. We think of how we leverage, and I think you've taken a different path to leveraging in that particular business, right? Where people think, oh, we have to hire people to do it, or if you can actually create a system where it can be delivered without people, like, even more efficient, even more reliable, even more on demand, direct. You know, the client experience can be even greater. So that's pretty cool. I like that a lot. So where did it go from there?
Wow. Yeah. Great question. So it wasn't a business overnight, right? I'm just. I'm putting things out on YouTube. People are starting to consume it, and you've got this idea. And I started, obviously, in aviation, I had some successful clients because it takes money to learn to fly. So I was surrounded around, really, the right people, business owners and stuff. And I began to ask them, hey, is this something you would use? But then the size of the task, Bob, became daunting. So the FAA, who regulates our pilot certification here, requires 20 hours of ground school, not including quizzes, books, everything else. So I'm thinking imagine, and you create content, right? Imagine 20 hours of edited content, right? You know, how many cuts and everything else, like, so imagine you have created content perfected for one course, by the way, and there could be up to seven or eight courses. So I'm like, wow, 20 hours of edited content, Plus I got to create question databases. There's no AI to help with this sort of stuff, right? This is 17 years ago. How do we. How do we go about this? And I'm having this conversation over lunch with one of my flight students, and he said to me, you don't have to get it right. You just have to get it going. And I'm like, a perfectionist at heart. Probably like yourself and everything else. Like you just want to. I want to do everything. I always wanted to be the A student. I always want to do everything right. But you don't have to get it right, you just have to get it going. And he said to me, he said, go make two lessons and try to sell the course. And if you sell the course, you've got a two lesson head start to go make the next two lessons and the next two lessons. I mean, the whole course ended up being like around 25 lessons. I'm thinking, what do you mean? Just make two lessons of a 25 lesson course and it, just sell it, like sell 5% of a course. He said, yeah, you have to test the concept before you invest a year of your life in this thing, test this thing out. You don't have to get it right, you just have to get it going. I said, wow, okay. So I, it's, it's funny to, in order to even graduate again. I'm 18, 19 years old at this point. Just graduated high school. The only way I graduated. I actually had very poor grades just because, not because of lack of knowledge, but like a lot of people, I just wasn't interested. I wanted to fly. That's all I really wanted to do and to take an easy course. I took television production and the professor literally told me, hey, if you get on camera and do these morning announcements, it's a guaranteed A. Everyone's afraid to get on camera. They're afraid to do the morning show in front of all their peers and be embarrassed. If you do this, you'll get an A. I'm like, I'll stand in front of a camera for an easy A. Sure, whatever. And I didn't realize that's what I ended up doing for a living, right? So in high school, I'm thinking I'm there for the easy A. I'm really, I'm at the gym getting my reps in of camera time and being charismatic and reading off a teleprompter and all these things and getting over that fear of embarrassment. So when I set out to make the course, I knew how to edit video. I knew how to be on camera. It was my first time ever dabbling with a Apple computer so I could edit. It was imovie back then, but I could at least edit. And again, I didn't have to get it right, I just had to get it going. So thanks to YouTube, I began using YouTube as my marketing because I already had a little bit of traction there and said, hey, I'M launching this course. It's just the first few lessons right now, you know, if you're interested, here's the URL and all these things, like, just a little bit of traction. I sold to one person and one person becomes two people. And now all of a sudden you're like, okay, I've got two people in a course with only two lessons. Let's go make the next two lessons. And as those people progress and some other people came in behind them and like, there is no overnight success. Like, we made a beautiful, amazing eight figure exit from this business, although it doesn't sound like it right now. You're like, this is just a kid with a YouTube channel and two customers.
You missed a step.
Exactly, exactly. It was not an overnight success. It was 16, 17 years in the making to do that a customer at a time. And I don't know who taught me this or where this came from, Bob. And I'm sure you've done the same thing because you're very involved in with everything, literally intimately with your clients. I began to call every customer and they were, they were genuinely surprised, like, who's this stranger from the Internet? Because I didn't know them. Who's this stranger from the Internet? I've seen him on YouTube. I bought his course, now he's calling me. And we would have 30 minute conversations and I'm over there just taking notes. And in my mind I thought I was selling to someone, Bob, who was like, I'm going to work for Delta or Canada, or I'm going to have, you know, they were going to be an airline pilot. And you know who I really talked to? I talked to the dad who, it was his dream to always learn to fly, but he just had to put the kids through college. So his dream took a back seat.
And now it's his teacher.
You're exactly right. And now it's his turn to pursue his dreams because he's been so busy with his family. And I'm like, oh, I thought you wanted to go work for Delta. No, no, no. This, this was just, this is a passion. I've loved aviation since I was a kid, and now it's finally my turn. My finances are in order. I've got the time. And I'm like, wow. And if I had never taken the time to do that, I would always thought I was selling to a future airline captain. In reality, all this guy wanted to do was put his kids in the backseat and fly them to go get a hamburger at, you know, some other airport. One day. And I'm like, and it changed everything I did. It changed how I marketed it changed how I created my content. I began to say in my videos, you know, hey, listen, we. Aviation is the freedom to go where you want with your family, you and your spouse going on a weekend date, a weekend getaway. And that changed our business because now I was, I knew who I was talking to as a customer, and that changed everything for us.
And, and I think you said, you know, back to your. It doesn't have to be perfect, it just has to get started. You know, I can relate to that in so many different ways that every time we do a service offering, it's like we're testing the market to say, is this something that you want? Right? Is this something that you really want to have? Is this going to help you in your life and your business or whatever? And I know when we first launched our coaching business, we did the same sort of thing. We did a live event and we thought, okay, off the back end of this event, we're going to share three days worth of content. We're going to teach, we're going to train, we're going to inspire. And then if you want to continue with that, then, you know, let's, let's continue into this coaching program, course offering. Right? And we didn't have the courses built, right? So we were selling the idea that we've got these courses, but we hadn't built them yet. And to your point, it's like, okay, do you spend the time, the months, the years, potentially building these courses, perfecting them to not have anybody want them? And I, you know, get started. Not perfect, I think is a perfect sort of process, market test for us to get things live. Okay, so tell me a little bit too about your YouTube. So I'm imagining as you evolved, you got past the 24 viewers, you probably built a pretty substantial presence on YouTube. Any insights from building a YouTube channel that would be valuable for people?
Sure. So we were very early in YouTube. We were one of the first channels to get. I don't know if anyone watches this in the video. I still have the YouTube award behind me there to hit the hundred thousand mark. That was years ago. But I made a big mistake with YouTube as well. And it's important, important that people understand this because we get tied up in these vanity metrics of subscribers and views and everything else. At the end of the day, if people aren't opening up their wallets, it really doesn't matter. But the mistake I made was I kept the business model going of I give away content on YouTube. Every YouTube video has a call to action. Hey, come check out our course. And that's a fine model. And I didn't realize the flaw in that model though until I don't know the year, but I'm probably about a year, maybe two years into business. So maybe about 15 years ago YouTube before it was owned by Google again had a site wide hack where a lot of the channels were affected. Again they're a young business but they were growing. They were a target for hackers. My channel was deleted by these hackers. All subscribers lost, all views lost everything. Completely lost. And that's when it dawned on me. I had no email list, I had no phone numbers, I had no way to get. My only method of marketing was organic YouTube. And I lost everything. It was like, you know, it was like MySpace was your marketing. And MySpace went away one day, right? In this case, YouTube came back and I had to make a new YouTube channel and was, and literally start over and you can actually still see that video. It's called Mzeroa Restart where I'm like in probably my parents bedroom still or my parents spare bedroom explaining the story of what just happened. And that was a big eye opener for me. And from that moment on I say I am going to be. This sounds bad to say but it's true. I'm going to be in the data collection business. There's a reason Facebook changed their name to Meta, which meta means data and there's a big uproar about that. But they're right, they're a data company and it's important for me to collect that data. Obviously doing the right thing with it, I'm not sharing it, I'm not doing anything like that. But whatever data, emails, numbers, what I can collect because these are my customers at the end of the day the same is true. There's people who sell on Amazon right now who don't know who their customers are because Amazon keeps that data. There's people who sell on TikTok shop, they don't give you that data, right? So just be very mindful. Are you actually building a database of customers? Because MySpace went away one day, YouTube got hacked one day like TikTok goes on the verge of being shut down every few weeks. It seems like, like if you have all your eggs in one basket you may not really have a business and it's important to be collecting that data. So that was a big change for us and how we did that is we went, it's still popular today. But back then the idea was we're going to give away these ebooks in exchange for an email address. Like that seems so. That seems spammy now, honestly. But 15 years ago, that was like, revolutionary to think someone's going to give me something for my email. And that's what we really did. We would do, like yourself, we would host webinars, we would do all these things. And by the way, I needed your email to get on that webinar. And that is how we began to build the database.
I got a quick one, quick story for you that's very similar. We did our first major event and it was the first time I spoke in front of multiple thousand people. Nerve wracking, right? The whole I shouldn't be there. We had, we had that going on, overcame it. Of course, Kevin o' Leary was on right before me. And so Kevin o' Leary opened for you? He did. He opened for me. That's usually how I present it.
Yeah, of course.
Yeah. So. So I do this. I do this presentation. It goes extremely well. I have this lineup of people. We also had a booth at the event. We actually had a lineup for about 5, 6 hours. Our entire team, everything that we had at the trade show booth, gone. Business cards, brochures, books, everything, gone. And at the end of the day, we were all exhausted and we were like, this is amazing. What an incredible day. Like, we gotta do this again. And I had the same realization that you did, Jason, where I went, oh, my God, who took all of our stuff? I don't know who they are. What do I do? We blew this, right? And so all of a sudden we transformed that where, you know, every time we have a QR code, there's a download, there's a book, a meeting, there's a call like, get in our database so that we can follow up with you and make sure that we can help support you. Because on the other side, you get a business card, a brochure, it sits on a desk in a. In a drawer somewhere, and we lose it. And so I can appreciate that so much. And it's such a tough lesson to take in, but man, oh man, listeners, you know, avoid those mistakes because it is. It's the data business. And for us, again, we have, I think, a database of about 40,000 people that we have their email contact info. And all we do is we continue to add value. And when people are ready to engage with us, they do. And that's how we do it. But at least we know who they are. And that we can stay in touch with them. So. Okay, Jason, so you, you built the YouTube channel, you've built this business, you're selling online courses. You know, you realize a certain level of success, which I would love to hear about that. And then you made an exit. So tell me, you know, where you took that business to and then how the exit really started to take form for you.
Sure. So what really scaled that business for us? Yes, we did very, very well. B2C, life was good. But then all of a sudden, these colleges started knocking, right? The. The big embry riddles of the world. And these big aviation institutions are going, hey, all our students watch your stuff. They buy your books. They're paying 300 grand to be at our school. Why are they still watching your stuff?
Right.
And that was kind of an interesting conversation to have. We would like to use your curriculum. Well, of course. But we want you to link into our Canvas LMS and our blackboard. And I'm thinking, I have no clue how to pull this off. Right. So you run into these obstacles sometimes and even how can I service these clients? But where the business really began to scale is when we migrated. Yes, B2C is still the largest part of our business. But what really attracted the PE firms to us, they all love B2B business. B2B, it's just, it's contract based. You know, we renew the contract every year. Life is good. In fact, when we, when we sold, they were mostly interested in the B2B. And still that, that's their main focus is growing B2B. Yeah. You know, to this day.
Here's the beauty of the B2B. Right. Is that the, the B2B. The B has C. Yes. As well. Right. So, yeah, you know, the one business has a network of. Let's just say it's me, 40,000 people. So they can sell to me. They can likely indirectly get to those consumers as well. Anyway, sorry to interrupt.
No, you're exactly right. So we're growing our B2B business. Life is good. And all of a sudden, at this point, by the way, we're probably about 24 people on payroll doing a couple million dollars a year. We've created a very good lifestyle. Yeah. Solid business. A very good lifestyle for my wife and I. But like a lot of mom and pop businesses, and Even at a 24 person business, we were still husband and wife running it like a mom and pop business. And I'm sure nobody from the Internal Revenue Service is listening to this in America, because I'm sure I'm the only person who. Whoever did this. In business, you go to the local grocery store and you use. Yeah, cover your ears, please. As the accounting professional. Cover your ears. You go to your local grocery store and you use the business card. And in QuickBooks, you reconcile it as it was an office meal, right? You go to a conference. And we stayed in the Ritz Carlton instead of staying in the regular old Spring Hill Suites Marriott or whatever it may be. And this private equity company came to us, and we were so excited. They wanted to buy us. It was a search fund, so we were not prepared. They were seeking us out. Like, you always hear, oh, you're building to sell. You're doing this. And, yeah, that's an idea. But, like, they reached out to us cold and we got excited. They're throwing numbers around. We're under NDA, we've got Lois. All this is happening. My wife and I are thinking, like, we've already got the money spent in our mind, like, where we're gonna go, what we're gonna do, what. Where we're going to retire, all these different things. And then they get into tax diligence and financial diligence, and they're going through everything. And remember, you sell these businesses based on ebitda. I mean, yes, there's. There's ip, there's a lot of other things, but at the end of the day, EBIT is what really matters for a multiple for these businesses. And they begin looking at the books. And I'm going, well, yeah, well, that. That's a grocery expense. It was really. It was our personal groceries. And I'm trying to explain, Explain all this stuff. There's all these ad backs and everything else. And they, they literally. It was over zoom, but they looked at me and said, hey, Jason, it is clear you have a very great business here. However, based on QuickBooks, we cannot make heads or tails of it. So, unfortunately, we. We need to walk because we don't know if you're sending $3 million to the bottom line or $300,000 to the bottom line. We don't really, really know. There's ad backs and this. And this story, and I'm sure it all makes sense, but we don't have the time to uncover this spider web. So we're going to walk. And I was devastated. Like, I'm thinking like this again. We already planned the vacations. We're like, we're all in on this thing, like, and because of how I was running the business. And by the way, Bob, this is a Again, multimillion dollar business. Multimillion to the bottom line as well. And yet Jason was still reconciling QuickBooks and Jason was still basically the CFO and I was the bookkeeper and I was still wearing all these hats because sometimes as entrepreneurs we believe the lie that, well, nobody will take care of your money like you do, nobody will manage your business like you do, nobody will do customer support like you do. And when you believe that lie in business, it will hold you back. And I believe that lie. And literally that same week we went out and we hired a part time CFO. We didn't need a full time CFO, but did a fractional CFO for 25% of their time. And they came in and loved on our business during that time period. We're available for questions. We went out and hired a full time bookkeeper to clean up the books. And I kid you not, nine months later, history repeats itself. A different PE firm reaches out. This one at a higher multiple with, you know, with more firepower, with everything else. We sail through tax diligence, we sail through, you know, financial diligence and everything else. And we ended up getting, you know, I'm not able to share numbers, but we, we did significantly better than we would have ended up making a great eight figure exit and sold the business. It was, you know, Napoleon Hill says something in the book, think and Grow Rich. He says, in every adversity, there's the seed of a greater advantage. And you could have looked at the first PE firm and said, oh my goodness, the sky is falling. The world is over. No one loves me, right? Or you could say, hey, this stinks. Let's learn from it. Let's clean up the books. Let's run this like a big boy business and stop running it like a mom and pop business business. It's time to put our big boy pants on. And sure enough, that prepared us for an even higher multiple, you know, and did better for ourselves, for our team members, for everybody from that standpoint.
So tell me a little bit and congratulations on that by the way. You know, I do feel like things happen for a reason. And, you know, another lesson I think shared is making sure that, you know, even if you're not looking to sell, you know, keeping in mind that if the right buyer comes in, they're going to want to see a certain level of proficiency and professionalism, you know, whether that's, you know, higher level assurance engagements as well, to have greater disclosures. Anyway, it's something to just be thinking about, guys if you get into a business where you've built a business that is now able to get sold, you probably want to look at those things just to be ready for it right now. In Jason's example, it was better that the first deal didn't happen anyway. So that was probably set up for success, Jason. Probably self sabotage that knowing that a better deal was coming as well. It seems like you've got, that, you've got that level of intelligence for you. But talk to me a little bit about the emotional component of that exit. And did you and your wife go do those vacations and enjoy that time and, and then what happened after that?
Great question. We still haven't done the vacation to cut to that, that ending. Yeah, I know. The first day was very exciting, right. We refreshed our bank account so many times waiting for the wire. We got locked out because we were that excited. We just kept refreshing.
Is this real? Is this real? Yeah, yeah.
And then it was really there after we got our password reset by the bank. And then honestly, that was exciting. And the next day was kind of sad because like yourself, I'm a person of routine. I had this one to one every, you know, every Tuesday or whatever the day was. I then I have this person and I have this meeting and I do this and I just like. And now I'm like, well, what do I do today? I don't really, I don't really have a job. I don't own the business. It was like, it's wrong to do this, but it happens. I had 16 years of my life tied up in this business. Like I had my identity in this business. And that's not right.
Right.
You need to find your identity in other places other than your business. But that's very hard to tell these A type personalities, these high performers to not do that. Right. Yourself included. Right. We tie up our identity in our business and 48 hours later I was kind of sad about it. And it was actually my wife who kind of, kind of pulled me out of it. Right at the time I was 35 years old. She's like, listen, you are too young to retire. Like, you have a fiduciary responsibility to use these skills that you've been given to go do. The next thing I said, okay, well great, what am I going to do? I signed a non compete that said I'll stay away from airplanes. I'm like, what am I going to do?
I know airplanes.
I know airplanes. I'm a flight instructor. She said, time out for a second. What you are really good at is taking complex subjects like aviation and explaining them into plain English for other people to understand. I said, okay, well, what should we do? She said, you know, over the past however many years, you have stewarded this family's finances from the brink of broke. Like, I'm talking tow truck at the end of the driveway, broke. To riches, to wealth, to losing a bit of that, to building it back up again. Like, you're budgeting, investing these systems you put in place. Like, it's been amazing to watch you do that. She said, that's what you need to teach. You need to teach other people who are stuck living paycheck to paycheck how to break free like we did. I thought, wow, okay, so it's so funny, Bob. I started over again with the exact same business model. I went to my office, I grabbed a camera, and I made a video on how to break free from the paycheck to paycheck cycle. I made a YouTube channel called Moolah. I uploaded there. I said, let's go back to the basics. Let's see if there's any interest in that. You know, that original video, also launched on TikTok today, has 2 million views. I said, okay, unbelievable. We're onto something. We're onto something here. Right? There is. You know, aviation's a very small niche. There's only about 400,000 pilots in the United States. How many people are living paycheck to paycheck? It's a lot more than 400,000, right? And the video went viral. And I said, okay, there could be something here. And that is really where Moolah was born out of. Again, it wasn't the sexy Stanford, you know, business plan and VC Silicon Valley capital. It was just, let's test the idea. Let's put one foot in front of the other, and let's go baby steps to this thing. And that's exactly what we did. And here we are. You know, Moolah is launched investing, saving, debit cards, everything else, you know, seems like an overnight success, but. But it wasn't. It's that business model. And you follow the same business model, Bob. It is give valuable content on the premise of you, like this free content I'm giving you. See how good the paid stuff is. Come to this seminar, Come to this coaching, download this app, buy this book, right? It is beautiful advertising disguised as content. And that's not nefarious or anything like that, is just great content marketing. And that business model will be around, right?
Forever, 100%. And I think you know, now more than ever, and even hearing you talk about this back, you know, whatever that was 20 years ago when you started putting yourself in front of the camera, right? There's a certain type of person, like my business right now we've got about 170 people that work for me. I can tell you that there's maybe one other person that would be willing to get in front of a camera. Right? And so it is. It's unique, right? And. And it's not easy, believe me. I. I wasn't the person who necessarily wanted to be in front of the camera either. But is one of those get out of your comfort zone, and if you can do it, personal, brand and identity is just so powerful. And to be able to get a digital message out to the masses, like, if you want to reach more people, it's not going to be the cold call. You know, you might be good at that, but, you know, to get out, to give value, to teach, to share, you know, build trust and awareness of who you are and how you can maybe support is super powerful. Don't forget that guys like this, obviously, Jason's done this multiple times in an incredible way. But, you know, we all need to be able to take advantage of this power that we have, of the knowledge and experience that we have. And Jason, I'm sure, you know, if you start 10 more businesses down the road, they're going to be equally successful, built on a similar foundation of what, you know, but over the last, you know, 20 years of knowledge, blood, sweat, tears. And they're going to continue to excel faster because of that knowledge and experience. So congrats, man, that's so happy to hear that. Now give us maybe an update of where Moolah is at in the stage of its infancy. And, and I know it's been launched, but what does it look like now and what are you looking to accomplish in the future?
It is still, right, an infant. Right? It's still being nursed, it's still being babied and everything else. And it's in a different spot, though. The aviation business, we bootstrapped here. We have our own capital to put behind it. Like you said, business is business. These foundational principles just work no matter what. When you understand business, my wife always gives the analogy, like, this is our sport. We don't really play sports, but business is our sport, right? This is our fun thing. This is our ice hockey, this is our whatever. Like, this is what we do every day. And when you understand those principles and those fundamentals, it makes Everything just exponentially. I don't want to say easier, but everything kind of falls into line better from that. But at the same time, you know, one trap you have to avoid falling into. And this will seem like an odd segue to take this question, but sometimes success can lead to making mistakes. It was very easy at the beginning of Moolah with a big bank account and this feeling like you've got the Midas touch or something like that. And, boy, that personality will get you hurt in an airplane. It'll get you hurt in a car going too fast, and it'll get you hurt in business most definitely, too.
You think you've got the crystal ball figured out, man?
Yeah, and I made some of those mistakes. I got. We got a little bloated too early hiring because we had the money now, right? It's different when you're bootstrapping. You've got nothing and you're eating ramen noodles. But when you have a couple million dollars in the bank, you start throwing money at problems. You go, wait a second, wait a second. This isn't the solution, right? Let's get back to the basics and let's get a little more humble. By the way, whether your bank account is big or small, it doesn't matter. If you take a humble approach to business, to decision making, to payroll decisions, to all of these things, you will find success. But if you think you've got a crystal ball, if you think you're Midas and you've got the golden touch, like you're. You're going to get yourself hurt and you'll be humbled. Rather, it's much easier just to humble yourself than be humbled by the marketplace.
Yeah, absolutely. And so as you've built Moolah out, I know you talked about your first business saying there's no AI. There's nothing like that in building the first one. Now that AI is involved, how are you incorporating AI and Moolah?
It's been a game changer. I mean, you gotta think about it like we essentially built a bank, right? It is your debit card, it is your checking, it's your savings, it's your investing picture. Like if Robinhood had a debit card and IRA and everything else. It's like all these things combined into. Into one.
Are you robbing from the. From the rich and giving?
No, no, gosh. I mean, the app. I mean the app. I mean the app. They're a competitor, right?
I'm just kidding. I'm kidding.
I know, I know. I'm teasing you Too. So isn't that kind of a silly name? I thought about that. Like you're like I'm competing against someone. Like, do they really know what Robin Hood did? Like, I don't know. But anyways, hey, they're publicly traded and I'm not yet. So I got a lot of work to do. That's why I look good for them. And that's what I have to do from this standpoint. That is the long term vision, by the way, is the ipo. But anyways, to that point, I look at what we've done, I share all that. To say we did all that with like six developers, do you know what it would take, how many payroll dollars it would take 15 years ago to say I'm going to build a bank. And by the way, I want investing and I want to trade and I want to do crypto and I want like it would have been off the chart, the size of the team you need and how long it would have taken. I did this with six scrappy people. Yeah, we put in some long hours and everything else, but we just figured stuff out, right? Including even going back to we release a piece of content every single day. You know, back in the aviation business, it took all my effort to do a piece of content a week. Now if you go on any of the Moolah social media channels, there's at least one piece of content, high quality, every single day. And again, we do a lot of that. I mean the team is using AI to edit, we're using AI to post. So not only from our standpoint, like our it's a content machine, it's a development machine, but how we're using that to help our customers as well. Right. I can look at a customer and say, okay, Bob, or let's say there's someone named Bob that lives in Toronto that's renting a two bedroom house. And I know you're paying 2,500 bucks a month for it. And how do I know all that? Well, I'm your bank. You went through the KYC process. I know where you live, I know all these things. I run all that through a language model and say, hey Bob, you're paying way too much. Because the average two bedroom rental according to this is actually $1,800 a month. But the cost of moving costs this. So we're running all these different scenarios for these clients who are living paycheck to paycheck to help them find the small wins to break free. That and it's not even what I Expected people are asking us these like questions that you and I would seem silly. Should I, should I lease or buy a car?
Oh, I get it all the time.
Should I buy the BMW or should I buy the Ford Ranger? And like, please don't buy the BMW. You're living paycheck to paycheck. Like, but these are the questions people ask, should I rent my house or buy my house? Like, it's not what. I just like the aviation business. I expected all future airline pilots. You know, in Moolah, I expected it was all a bunch of Gen Z kids just getting started. At the end of the day, it's a 45 year old nurse who's making really good money, but doesn't understand why she has more month than she has money. And Moolah is giving her the financial intelligence to show her why and show her that she's making good money. You just need to make these changes and stop going to Best Buy and buying the new TV and the new iPhone every time it comes out. Right. Like these are the changes we have to make and that's what we're able to show people. You know, the business you start and the client you chase isn't always the one you end up with sometimes. And that's why it's important to always be developing that avatar.
Yep. And testing the market to see who is really benefiting from this. So you talked about six people really hunkering down, rolling up their sleeves. Now I know as a business owner, to get six people to put in that much work and effort, you've got to have a pretty strong purpose and culture. What does that look like for you, Jason? What is it that you're able to do in building this team that really brings everybody in and gets them passionate about what you're doing?
You have to be in there and roll up your sleeves with them. Right. Like you have to. I always say a leader is not afraid to take out the trash. You know, like you have to be willing to do everything. And I'll give an example. And unfortunately it's become a polarizing example just because of the media and stuff. But put politics aside, look at like an Elon Musk, right. When he first acquired Twitter, like if you read his biography, like he was in there with the team, sleeves rolled up, saying, hey, because he knows how to code, because he knows programming languages, because like he knows how to do every aspect of those businesses. So again, politics aside, that dude is not afraid to put in the effort, get his hands dirty, make a cup of coffee, with you and let's just pound it out on a keyboard till we figure this thing out. And that is the same approach we took. And again, it is challenging. We have three children, we are, you know, I'm married, all these things, but the kids get it right. The kids are now homeschooled and half the time they're sitting right over there doing their homeschool while I'm over here, you know, working on a Python script with the guys. Like, and I'm not as tech savvy as they are, but I know how to talk the language, I know how to lead the team. Just like you don't do a lot of the things you used to do in your business, but you still know how. Right. You still got it. So you can lead them.
Yeah. It's one of those things. Yeah. That almost as you become the leader, you have to give up a few of those things too. Right now, I think foundationally it's imperative that you know how to support and ask the right questions and be able to do it. But at some point you almost have to give up being that expert and empower others to do that, which sounds like exactly what you're doing.
Awesome.
You know what, Jason, I'm so excited to hear your story. I'm excited to see your success. And I'm definitely going to be your next subscriber, Amula. That is if some of my viewers don't get on there before me. But I wanted to maybe just end with, with one last sort of question for you. And I usually end with this. You know, if you had to think back of being an entrepreneur fairly new in your business, or looking to grow and scale, what would you know? One major piece of advice be that you would want to give your former self.
Always be looking for leverage.
Right.
How can I? We just talked about a few points at the beginning, but that business didn't go from zero to an eight figure exit just by one thing. Right. It was a series of finding leverage. Sometimes that leverage is taking your courses and put them on the Internet. Sometimes it's making the strategic hire, sometimes it's implementing the software. So it is finding leverage in everything that you can do. How can I, what can I do today? They can have the greatest impact on top line, bottom line, this KPI, whatever you're trying to attract. Like, I would just challenge anyone listening today, look at your to do list and say, of the things on my to do list today, what is the one thing that's going to have the greatest impact to my most Important KPI, right? Or the bottom line.
Right.
Top line, however you want to look at it. Because I guarantee there's a lot of junk on there, there's that you can farm out to somebody else. Because at the end of the day, as the leader of your company, you should be honestly working on two or three, like big things. Right. You shouldn't be in Google Ads making every little pay per click campaign. There's people way smarter than you that can do that. Right? You feel you need to.
No, there's nobody smarter than me. Right. Isn't that the feeling?
That's what people believe. Right? Like just go on upwork, go to your marketing department, whatever you gotta do. There's somebody who knows Google people PPC better than you do. Stop trying to figure it out. Right. And go work on the bigger picture thing.
Yeah, absolutely. Guys, this is Jason shepherd, CEO, founder of Moolah, amongst many other things. Jason, where can people find you? Obviously, Moolah. Check it out on all of the social platforms, start with YouTube. Sounds like there's a really great framework there. Where else can people get a hold of you, Jason?
Well, and that's exactly right and exactly where I want them to start. That we are in the business, just like yourself, of we give away great content first. Fall in love with us first before you even consider downloading the app. So we're across the four big platforms, TikTok, YouTube, Instagram, Facebook. It's a Moolah copilot. I had to work in the aviation term in there. Moolah copilot across all four platforms there. You had to. And now Copilot's like a, like a sexy AI term. I'm like, this is like again, futuristic stuff here.
Hopefully you had that trademarked.
Yeah. Before Microsoft. Yeah, I'm sure I'd want to take them on. Right, so it's Moolah Copilot across those four big social media platforms. Find it there. And of course, if they want to download the Moolah app, they can. Right now it is only in US app stores, but we are persistently pursuing our northern neighbor to get approvals. But it's a little challenging. I'll leave it at that. I'll leave it at that.
Fair enough. Yeah, fair enough. I'm sure permissions and allowances are maybe a little bit more strict now too, than they have been in the past, but we'll all get over that together. Guys, this has been a thrill. Jason, thank you so much for joining me today, sharing your story for everyone else. Just a reminder, I'M Bob Govreau, the host of the Wealthy Entrepreneur. We're here to empower business owners with the financial confidence to make informed decisions so that we can change the world together. If you found some valuable insights, which I know you have, I have found some incredible insights from Jason. Make sure that you're sharing these with people. Right. We know business owners, we know individuals who need this sort of support and insight. If there's something that's triggered, you help others by sharing this out. Make sure you give us a like and a follow so that you can be here next week when we release our next episode. But once again, Jason, thank you so much. And to everybody, thanks for joining me today. We'll see you again next time.







