

30 Sep 2026 · 51m · 20 chapters

Building generational wealth through entrepreneurship, uncapped earnings, and scaling a financial advisory platform (not just investing). Jason argues “saving your way” is insufficient; true wealth comes from investing in yourself, owning revenue-producing assets, and building teams that compound.
Jason McCool is a nine-figure entrepreneur and owner of a financial advisory platform. He grew up in a blue-collar Massachusetts area with military parents; his father was a pastor. He dropped out of college, started in entry-level business processing, got licensed after meeting a financial advisor, and later built a platform with 800 financial advisors across 28 locations in 17 states. He says he’s been fired from every job he ever had. He sold part of his company for about $100M (reported total ~$130M) and still owns 20%.
“Enemy number one is the paycheck.” Wealth comes from ownership and uncapped compensation; risk is emotional. Rich clients often don’t spread referrals; working-class clients do. First five hires set culture; hire Gen Z and let them own a “book of business.”
“Kitchen table” startup of Sweetest Gifts (failed) and J.E. Bentley (failed) before scaling. First hire was a recruiter who produced nine people, then coached compounding growth. Mentions Larry Post as a mentor; Tom Brady as an example of needing the right team. Real estate strategy: buy tenements, tenants pay debt, repeat.
Written by AI. May contain mistakes.
Discussing Jason's upbringing, family background, and early career aspirations.
“Welcome back to the School of Hard Knocks podcast.”
Jason shares the pivotal moment that led him to become an entrepreneur instead of seeking traditional employment.
“But let's talk about, I want you to take me back to the exact moment that you realized that you were exposed to the fact that it was possible to create a nine figure business and ultimately build a nine figure net worth.”
Jason outlines the early days of starting his first company and the challenges they faced.
“I'm like, all right, this is my opportunity to compete with people at a different level.”
The importance of recruiting talented individuals and creating a strong company culture.
“You know, we call it the kitchen table, right?”
Explaining the concept of building a platform for others to generate profit and grow.
“Who are some of those initial hires that you brought onto the team to really start to take the business to the next level?”
Jason shares insights from his past experiences and discusses financial strategies for success.
“Well, that's the whole process of a platform.”
Discussing investment strategies tailored for individuals at various wealth levels.
“good at building relationships for people to be able to trust you with their money.”
Learn effective investment strategies for growing wealth from $100K.
“I definitely, they don't want to share it.”
Understand why saving alone won't lead to generational wealth and the importance of investing in oneself.
“So you find me successful and you decide you're going to pursue a business that I have.”
Explore valuable lessons learned from early job experiences and the importance of mentorship.
“You know, your parents probably wanted you to go in the military.”
Exploring the potential of blue collar businesses and personal experiences.
“So I think these blue collar businesses are ripe for opportunity where they're simple businesses to get in.”
Discussion about the Take the Power Back job board and its mission.
“And Take the Power Back is really a passion product.”
Comparing investment strategies in real estate and the stock market.
“So, you know, if you're, if you're part of a group or club organization, you can basically go and you can, you can request to have a successful person speak.”
The importance of associations and influence in achieving success.
“Who you associate with is just as important as who you don't associate with.”
Personal stories behind car purchases and their sentimental value.
“Well, you can steer that into a really great business for yourself.”
Advice on wealth building, financial decisions, and entrepreneurial paths.
“Like, do you kind of have a typical rule of thumb where it's like, hey, you know, you should have this much money in the bank, this much passive income?”
Discusses financial decisions, the value of education, and alternative paths for young people.
“One owns the business, but you can do both, right?”
Explores different definitions of wealth and the importance of cash flow over net worth.
“Let the kid get paid minimum wage or whatever it is that you have to do, but give the, give the person a shot.”
Shares insights on tax strategies and deductions for real estate businesses.
“So I want to talk about something he just said right there, though.”
Jason shares his vision for inspiring Gen Z to embrace entrepreneurship.
“That's why most really wealthy people are in the development business because you, it eats, you're building your net worth while you're eating away your taxes all at the same time.”

Get the gist, explore an idea or ask about something said.
On School of Hard Knocks Podcast, what are the key points of this episode?
Automatic transcript. May contain errors.
0:00Jason Mickool: Jason, I want to talk about money. I want to dive into it right now. Talk about money. You're broke at 500 grand. You consider them broke? I consider them broke. So at what point financially does somebody have f***ing money? If you have a net worth,$250, you can kind of do whatever you want. $250, what? No. Yeah, yeah. So what about$25 million? You could have a bad summer and blow$25 million. What? I get paid quarterly today. I think today is a payday for me. It's like$4.9 million. Decent payday. Different day day. Yeah. 90 days later, if I was young again and I was telling people, you know, what should I do?
0:35Don't ever go work for a p***. Your wife pushed you to be an entrepreneur. My wife is a very kind, amazing human being. And I was trying to get a job. I was looking for a job. This faint look comes over her face and she says, can I be honest with you? And I said, yeah, of course you can. I would expect nothing else. And she goes, you're just being a p***. Wow. Let's just start.
0:52Jason Mickool: You do it yourself. Mr. Jason McCool. This was an incredible conversation. Is this a good conversation or what? I loved it. The only way to true generational wealth, as you put it, James, is to... What's going on, everyone? Welcome back to the School of Hard Knocks podcast. I'm James. I'm here with Jack and Josh, and we have an incredible guest for you all today, an expert on building generational wealth, Mr. Jason McCool. You sold a part of your company a couple of years ago for about$100 million. Is that correct? Yeah, just about, right? When it's all combined and everything. It's probably in the 130 or so amount.
1:28And I still own 20 % of it.
1:29Jason Mickool: Jason, did you come from a rich family? Did you? No, sir. No, sir. Did you come from a rich family? Not really. No, not really. Military parents. Oh, military parents. So no, my, my, my dad was a pastor. And before that, my grandfather was a Lebanese immigrant, came across on the, on the boat and built a boat business, lost it in 1980. We literally ate tomato sandwiches. So when were you initially exposed to the fact that you could build a hundred million dollar company? Because correct me if I'm wrong, right? And for context, you know, you're one of the biggest, you know, financial planners in the entire world.
2:01Jason Mickool: You're managing hundreds of millions of dollars for some of the wealthiest people alive. So I want this podcast to serve for the people watching as a blueprint on how to build generational wealth. Can we make that happen today? I think so. I think so. You know, it's clear. I just want to, I'm not a financial advisor today. I own a financial advisory platform, which is different. I am, we have 800 financial advisors in 28 locations in 17 states across the country. And my wife and I started it from scratch. But let's talk about, I want you to take me back to the exact moment that you realized that you were exposed to the fact that it was possible to create a nine figure business and ultimately build a nine figure net worth.
2:39I didn't know that that was actually possible. I dropped out of college. Did you finish school? I did finish school. You did, right? That guy did right there. I'm going to drop out right there. Come on.
2:47Jason Mickool: Thank you. So I grew up in a shitty town in New Bedford area, Dartmouth, Massachusetts. I always say if this is the Cape in the Boston, that the armpit would be where I grew up. You grew up in the armpit. Most of my friends are great people. I still hang around with them all the time, but they are, you know, it's a very blue collar community. Never liked school, never liked passing exams or taking exams. I like to work. You know, I like to make a buck, right? So if I could make a buck, if I could wait tables or bartend or cut a lawn, that was where my passion was. And I didn't think, you know, and I dropped out of school, so I didn't think I had an opportunity to get into finance.
3:28Took an entry level job in doing new business processing. My dad went from the cloth to selling boats. So I used to sell boats part-time. So I had a little bit of sales experience. And I got lucky once and found myself introducing to a financial advisor who took a liking in me and taught me the way to get my licenses. And I went and got my licenses. I went into sales. And then that was my rock. So I wasn't going to give that up. I'm like, all right, this is my opportunity to compete with people at a different level. So I ended up outworking everybody. then I went into leadership, went into executive leadership.
4:02And a fun fact for you, I've been fired from every job I've ever had. Every single one of them. And only nine years ago, my wife and I, I had been getting fired from my last job before I, before I decided to start the company. And we were out doing what most people do contemplating life, day drink. So we went out, we were pounding some liquor. And my wife is a very kind, amazing human being. And I was trying to get a job. I was looking for a job. And she said, this fake look comes over her face and she says, can I be honest with you? And I said, yeah, of course you can. I would expect nothing else.
4:34And she goes, you're just being a pussy. Her words, not mine. So for anybody that's out there, I didn't want to offend anybody. And I was like, what do you mean? And she basically went on to say, why are you going to seek a job? We can go bartend if it doesn't work. Let's just start. You do it yourself. Why are you trying to chase an opportunity that somebody else is trying to give to you, bet on yourself and I'll be by your side. And nine years later is crazy how it worked out. And, um, you know, your wife pushed you to be an entrepreneur. My wife, what I say is she gave me permission to fail.
5:09The responsibilities I, I, I had built a career where I made decent amount of money. We lived in a big house and did nice cars and took nice trips and stuff. But I wasn't going to build any generational wealth that way. Um, and I, and I wasn't going And the security that I had in that ended up becoming my personal lid. That became the block that I had in my life from being able to take a chance. What ultimately led to the skills that I had developed in that role was to get us to where we are today, which is kind of nuts to think about. For us, we're like, wow, this is crazy. You need to tell us about that first day.
5:44You're like, okay, I am going to go all in. What did those first couple of days look like when you were starting your first company? You know, we call it the kitchen table, right? We've started companies prior and failed. So I want to be upfront about that, right? We decided we were going to do an online gift shopping called Sweetest Gifts. That failed. Her and I had done something called J.E. Bentley. We were selling insurance through bank channel. That was a failure, right? And we always kept our jobs. We were never 100 % in, and that was probably the reason why we failed. But we sat at the kitchen table and, you know, now you have AI, but we didn't have AI.
6:23So it's like, we got to write the content. I hate writing. Like, it's like the worst thing for me personally. We had to build a website. We had to build a brochure. We had to figure out the Google pages. But most importantly, and this is the difference why most financial advisors don't reach the level that we have done. I didn't go after one client. I wasn't looking for a client. I was looking to do what I had always done as executive, which is to recruit people that were talented, train them, and develop them. So my first hire when I did that was a recruiter. So therefore, that person got me nine people, and then I coached those nine people, and those nine people coached nine people.
7:04And then ultimately, we opened different offices in different locations, and that scaled the business. And just the compounding effect of doing that really well is what built the business.
7:12Jason Mickool: So I want to talk about, you know, after, you know, you started to kind of compound and get some initial success, you are an expert recruiter. That's another one of your superpowers. Yeah. Who are some of those initial hires that you brought onto the team to really start to take the business to the next level? Well, honestly, and this is why I appreciate what you guys do so much, because I have a passion and my passion is Gen Z. You know, I think people my age have this wrong outlook. They think they're lazy. They think they're entitled. They think they don't work. They think they don't do drugs.
7:42They think they don't have sex. They think they're all screwed up. And the reality is they're the hardest working. They're the most intelligent. They have sex. They do drugs. They just, you just don't see it. Right. And the narrative from people in my generation is terrible about people in your generation. And you guys are proving that every single day. I think what they're doing is the Gen Z needs leadership and needs vision. So what I do is I hire kids out of college for the most part. I give them a very clear track where they can make an unlimited amount of money, where they can own their book of business, where they can actually build generational wealth from the day right out of college.
8:19And those first five hires, I call them missionaries. So I wrote a book called Built to Lead, Built to Scale. And the whole thing is about those first five hires are the most important that because they become a reflection on the culture of what you're building as a company. So, you know, I'm not looking for Tom Brady. I'm not looking for the best recruit out of college. I'm looking for the person who is committed, qualified, with aligned values, and I'll teach them the rest.
8:47Jason Mickool: You said something right there that stood out to me because I don't think we've actually ever dove into it on the podcast with all the different guests we have is that you bring people in out of college and you let them own their own book of business. This concept of book of business, you hear it oftentimes in like the insurance business. In this case, you know, financial advisory. Can you kind of break down exactly what that is like where it's kind of like you're giving people the ability to be an entrepreneur within your company? Absolutely. Explain what that is. Well, that's the whole process of a platform.
9:13So the difference between a business, right, as a business is I generate a profit for me. A platform is I create a platform for other people to generate profit, right? And they own that. They have the ownership in that book of business. And there's a lot of businesses that are out there. Insurance is one of them. Financial advisory is one of them. You know, certain types of recurring revenue, you know, routes, if you will, like snap-on tools or something like that.
9:38Jason Mickool: Did you have that experience within a prior company that you worked for? Yes, sir. you took the expertise that you had and that helped you start your own. Yeah. You know, the best thing they ever did was fire me, right? They trained me. They gave me all of the expertise and how to do it. Paid training, they call it. Paid training. It was called paid training. I didn't know it was paid training and they made me feel like I was bad at it. When the reality is I'm way better at it than they are, you know, proven. I was always a top performer and a lot of times people get stuck. I was a top performer.
10:04My best year, I made 860. and I was 32 years old back in the 2000s, I thought it was a big deal, right? Never in my wildest imagination did I think that that's not even a month's pay, right? So it's just a different dynamic that you start to go through.
10:20Jason Mickool: How much money did you have at the time you started this business? When you and your wife were day drinking, how much money did you guys have? I mean, I had a few million bucks. I wasn't broke by no means. You had some runway to - I had some runway. I wasn't starving. I had been an executive for, you know, at that time, 16 or 17 years. And I was very effective at it. I just got fired all the time. Yeah. So this is definitely a lucrative business to be in is what you're saying. I hate to tell you, there's a lot of businesses and, you know, if I was young again, and I was telling people, you know, what should I do?
10:49Don't ever go work for a paycheck, right? Because you're, you're, once they give you a paycheck, then they get to give you three or 5 % raises. Go to work for a place where you have an unlimited, don't even take a paycheck and say, Look, can I get more of the revenue if I don't take a paycheck? And then I'm never limited by that. That is where you make all of your money, right? And then if you can get ownership, which we allow to do, that's even better. But uncapped earnings is the way to do it. If I work harder than you, we shouldn't make the same amount of money, right? And in most jobs, I can work twice as much as you.
11:25You still get the same raise that I do, and I don't think that's fair. And if you're a college kid or young, you should stay the hell away from anything that even resembles that.
11:33Jason Mickool: Guys, we're about to get right back to the podcast with nine-figure entrepreneur Jason McCool. But before we do that, look, guys, one of the biggest things Jason talks about in this episode is the difference between simply finding your next client and actually building a business that can scale. For him, that meant building a team, creating the right structure, and putting systems in place that allow the business to grow beyond just one person. And the same exact thing applies to your sales and marketing. And that's why we use HighLevel across our businesses at the School of Hard Knocks. And it's not just myself and my two other co-founders that most successful entrepreneurs I know and meet in today's world are using HighLevel as the all-in-one sales and marketing system to help scale their business.
12:12Jason Mickool: Because HighLevel helps you manage your CRM. It helps build out your calendar. It helps automate text messages and emails. It automatically follows up with prospective clients. So that way you're not having to chase them down. And guys, look, it's easy to have five, 10 different things going on. but this automates it all for you and systematizes your business. So waste no more time and start using HighLevel right now in your business by going down, clicking the link in the description of this video and start your free trial with HighLevel today to automate the sales and follow-up process in your business.
12:38Jason Mickool: Now, with that being said, let's get back to the episode. Jason, obviously working and building a business in wealth management, you have to be really good at building relationships for people to be able to trust you with their money. What would you say is your best key to success for building a relationship? with a customer, especially those that have a lot of money? In today's day and age, it's really tough. We didn't really focus on the people with the most money. We went after working class Americans, the mom and pop people that are still working. They're, you know, you're from a military family.
13:08You know, they've got a pension. They have a, you know, a thrift savings plan. They're hardworking people that have put away money and they're not getting the level of advice. So the best thing that you can do with those is give them a value proposition that they can understand in simple terms and nobody else is marketing to them, right? So if you go after middle America, you go after a working class America and you do a really good job, one of the things I know about hardworking people is when you do good for them, they want to tell as many people as possible. Rich people, you can do well for them.
13:40They're not going to tell anybody, right? And that's not universally true, but I find that those people are a lot better. So how you win them over, right? Is you meet them, you're very kind to them and you do a really good job and the rest will build itself.
13:54Jason Mickool: Is it because rich people are gatekeepers? They are to a certain extent. Don't you agree with that? You think they're gatekeepers? I think so. I definitely think so. I definitely, they don't want to share it. They don't want to share that. No, you know, it's like, if I give you that, then it takes from me type of thing. 100%, right. And the weak protect, right? So that's something I learned a long time ago. You know, give, give, give, give. It's the religious background and it comes back in spades. Jason, I want to talk about money. I want to talk about money and I want to talk about the different levels of wealth that people currently have and what you again, we understand that for the purposes of this, you can't necessarily, you know, be a financial advisor, but I want to talk about what you've seen the most successful people at each of these levels do, you know, in terms of building their portfolio.
14:38Jason Mickool: Right. So let's first start talking to that person out there that they have$100 ,000 saved. They have a little bit of active income coming in, let's say$10K a month. If I gave you that person right there, what's the investment strategy right there? How are you taking that person to a million as quickly as possible? Well, and it's weirdly enough, it's not in the stock market. It's not in any of that things. Right. So I think what you do is you systematically save in 401k and retirement plans and you get a pension if you're if you're an employer. But what you do is use that extra nest egg, if you will.
15:09And you try to build assets that actually will help build a business for yourself. I take a hundred, I'd go borrow a million. I'd go buy a tenement, some kind of building that rents income. And ultimately the tenants pay off the debt, right? The 900 grand. And then now I own a million dollar asset. And then that just goes and goes and goes. And then you take the equity from that one and you do another one. But is it easy to get that loan? It is, right? If you've accumulated 100 grand, you probably make two, right? Something like that. In order to be able to get to that place, you got to focus on building your income because your income gives you the opportunity to get credit.
15:44The credit gives you an opportunity to invest. The investment ultimately produces the wealth that ultimately that you'll be able to do. The other thing is, you know, you got 100 grand and you're working for somebody. You've got a runway right now to invest in yourself. Another better strategy is to say, you know what? screw the nine to five, 50, 60, 100 ,000 all year job. I'm going to go and sell real estate. I'm going to go be a financial advisor. I'm going to go sell insurance. I'm going to go bet on myself, right? In terms of if I work something that produces lots and lots of revenue as a career that nobody is going to give me a raise on, I'm just going to be able to build my own wealth.
16:23Jason Mickool: Wow. How big of a factor is risk in the portfolio and the clients that you manage? the wealthier the clients become the less risky they become you know so if you looked at my portfolio you know i've got a couple hundred million or more built into the equity of my business right so why would i risk the stock market stuff why didn't i put all of my energy into the biggest asset that i really own which is producing revenue for myself on a on an everyday basis so i think a lot of people don't really understand risk and when they say things like I want to be aggressive. I go, what does that mean? They don't really know what that actually means, right?
17:01So a risk is an emotion. So I always say when I'm making money in the market, you know, I'm aggressive. When I'm losing money in the market, I'm not aggressive, right? And I think that most people investing in these types of things don't really fully want to be really aggressive. What they want is somebody to help them hold their hand to make decisions when their emotions are high. And that's really what a financial advisor does. I feel like a lot of people, they know to invest in their 401k. They know to invest into their retirement accounts. But what's the most non-traditional way you've seen someone build their wealth?
17:36I mean, it's opening their own business, right? If you took the lump sum of all the millionaires or the wealthy people that you have, they're either entertainers, meaning they have a skill, they're athletes or they're actors, and the percentage is very small. But the lion's share of them are business owners and entrepreneurs. What happens in the first few years of you getting out of school is you have to learn a skill, right? And then once you learn that skill, what you have to do is you have to steal that skill and then go bet on yourself to go do the exact same thing that the business that you're learning from is doing that the person that's there has all the wealth, right?
18:14And that's the way to invest your time and energy is in you, right? And don't be a participant in the job that you have. Be a student of what is actually happening around you and how that person built wealth. Success is a copycat business. We're in a podcast studio. I was asking these guys before, how much is it? I think it's a pretty nice podcast studio. They say, yeah, it's$360 an hour. There's only a certain amount of hours in the week. What I'd be thinking about is, how do I have 50 podcast studios all across the country? How do I sell franchises of those podcast studios? How do I get other people to buy them from me and pay me just to participate in those?
18:54That's the vision that most people have. What happens in life, I think personally, is you end up, even successful people, their identity gets screwed up. So you find me successful and you decide you're going to pursue a business that I have. And however my level of success is that you perceive that to be will become my lid. So what I'm doing is I'm pursuing a level of success that has a ceiling that is defined by whatever it is that I view your success as. That becomes your limiting capacity. So make sure you choose the right endpoint. Find somebody that you think is wildly successful that you would like to emulate, and it's a copycat business.
19:36Just do exactly what that person did. Who did you emulate? There was a gentleman by the name of Larry Post. He's a mentor of mine. And when I was growing up, I saw this guy and I saw him speak, you know, and he drove a BMW, drove a nice car. You know, today he's worth a hundred million bucks. You know, he was in at the time he was probably worth 40 or 50 million. And I thought to myself, wow, I will never, you know, if I could. And he and I and I trusted him enough and I would ask him for feedback. Feedback's a gift, too, by the way, as a non-sports guy. if you gave me feedback, I thought it was criticism, right?
20:16I think sports people get this differently. If you play sports, they're like, don't do it this way, do it that way. You're like, okay. But as a kid that wasn't a sports person, and what I was smart enough to be dumb enough is I would ask him for feedback and he would tell me, I would do it. He would say, cut your hair, shine your shoes, wear a white shirt. Don't say this, say it this way. Do this, come in at seven, Work till eight. Do those things. And I was just like, look, you did it. So if you're telling me to do it, right? And who am I to say no to that? But if I picked an aiming point with a person that was worth$100 ,000 or even a million bucks, that would become my problem.
20:57The feedback that I would receive from that person wouldn't allow me to grow to the place that I would want to be able to get to. Is that the trait you've seen amongst a lot of the top performers within your company as well? Is that they're incredibly coachable? Correct. And would you say they have a back on, whether it's in sports or some sort of entertainment of like, you know, team, like a team environment where someone does have to get feedback in order to get better? Yeah, this is an important delineation. And I always say, I call it the 50-50 rule, right? 50 % of your success as a young person or any person has to do with what you bring to the table.
21:33Hardworking, coachable feedback. But no matter how much that is, right? you're only as good as the team that you play for. So think Tom Brady. I know you're a New England Patriots fan, 199th pick. I don't care what anybody says. He's the GOAT, right? There's no question about it. But if he was drafted to the Browns, he would not be the GOAT because he would have never learned what Bill Belichick and all of those teammates that were working together were able to show them, right? So it's not about the sports. It's about making sure that when you make a decision, first of all, you have to bring what you have to the table, right?
22:10But it doesn't matter. You need to make sure that the table that you're going to decide to put your time and energy and development is the right table, the right people, the winners, the people that you have, that have aspirations and that, that have a vision that are bigger than what you could possibly dream of because they're going to drive you up. You know, I, I like to snowboard when I snowboard with somebody's terrible. I play terrible when I snowboard with somebody who's good. I play at a different level and everybody does, make sure that you play at the right level. Jason, what is the biggest lie that the general public thinks about money that the wealthy know?
22:45The biggest lie that people think you can save your way into becoming generationally wealthy, it's a lie, right? It's just not possible. You can save 20 % into your 401k, you can make$250 a year, you can dollar cost average, you can put the money in an asset allocation fund, and you still will never be rich beyond your wildest imagination. The only way to true generational wealth, as you put it, James, is to invest in yourself. And that's just it, right? Find yourself a seat at the bigger table. Get coaching from people that have done it. Don't listen to people who love you the most. It's terrible advice.
23:23The worst advice that I see young people take is from their parents or the careers that they decide to go pursue in their own lives or what their parents did. Can you imagine if you decided to go pursue being a government employee? James has always been a soldier. Were you really? My dad went to West Point.
23:42Jason Mickool: He had an amazing career in the military. But my life would have been completely different because I almost went there. I mean, there's nothing wrong. Obviously, I love the veterans of our country and people that serve the country. Absolutely. There's no question about that. But it's very unlikely that that would have turned into generational wealth, what you're doing today. What you guys are doing today likely has the possibilities for you to create wealth for yourself that only can be imagined by most people. You know, your parents probably wanted you to go in the military. Yeah. You know, I interviewed this kid the other day and I was like, well, you know, what do you think you want to be in five years?
24:19I want to go get my CPA. I want to be an accountant. I'm like, that may be the worst decision in the whole entire world. I'm like, why do you want to do that? He goes, well, my mom's an accountant. I'm like, well, that's not a reason you should pursue that career, right? Why is that such a bad decision? It's a terrible, it's a terrible, terrible, terrible decision in so many ways. Number one, right? When you get out of, when you, let's assume you get out and you go work for the big five. Well, now you work for paycheck. You have capped earnings. You're working for a 10 % raise. Or let's assume you do that for a bunch of time and then you decide, well, you know what?
24:53I'm going to go start my little accounting practice. What do you think AI is going to do to that in the next five years? Right? Right. You know, there's no value. It's not a relationship based business. People are pumping out tax returns left and right. So Jason, it's safe to say enemy number one is the paycheck. Was that enemy one? Well, please, you don't even get me started. You couldn't, you want to be paid for your value, not your time. You want to be paid for your production, right? Not the pity of the person that's paying you. What they want you to do is they want you
25:22Jason Mickool: to work hard and get paid less so they can make more. That makes no sense. Did you work any interesting jobs growing up? Like, that's always an interesting question to ask. Like, we both worked at Chick-fil-A. I know you cut lawns. You know, I worked construction for a little bit. Did you have any jobs? I did all of those, my man. Yeah. And I got fired from every one of them. Right, as I told you. Unemployable. Yeah. Unemployable. I always like to ask, though, were there any valuable lessons that maybe you took from some of those early jobs that you worked? I mean, every job, you know, which you don't realize in hindsight is in every failure that you have is an arrow in your quiver that you end up taking from it.
26:00And, you know, I worked in a dry cleaner. I worked in what I learned was the bookkeeping. So the guy used to let me run all the books. So I ran the P &L of the dry cleaner. You know, years and years later, that application inside of a business I was able to learn from.
26:14Jason Mickool: What do you think, being that you are in the business that you're in? And it seems like, you know, your golden rule goes back to the most important investment people can make is back into their own business, right? Like you mentioned, you've got hundreds of millions of dollars in your own business right now, which is powerful. But what are you seeing are some of the most profitable, underrated businesses for people to start in today's world? Oh, you know, so like, I mean, I could just go on and on. But obviously, a financial advisory business, the multiples that you get for having that type of business, the bigger you are, the bigger the multiple.
26:43So like a 7X? No. No, you know, the bigger, like a business like mine gets a 15X multiple.
26:49Jason Mickool: Wow. Goodness. Yeah. That's crazy. Which is insane. So you're saying that we got to launch our firm for all the billionaires we interviewed. Well, you know, I think you got to, again, if you built a wealth management firm, the bigger you are, the bigger it gets. I would turn this into, I would turn this, you know, I have a friendly relationship with Grant Cardone. You know, he's got the coaching program, but really wants to do is invest in the real estate fund. So he wants everybody to put that money in the real estate fund, right? Because that platform gets big and he's funneling people in terms of monetizing his person of interest score.
27:20Right. Right. You know, what's funny? I have a nephew and I don't know all the particulars because we're not really tight, but he went to school for mechanical engineering. And when he was in school, like the three of you guys, he basically was like, I need to make some extra money. Right. So he goes and he starts a commercial cleaning business. Right. Senior year comes, he graduates top of his class. He's not a mechanical engineer. He's making more money. He's got 30 employees, right? And he's got a business with a commercial cleaning. Now, do you take that? And now what I would say to him is I'd like, okay, why don't you go open 20 of those commercial cleaning businesses around the country, hire people for a paycheck, make a margin on that profit, scale it and sell it.
28:02So I think these blue collar businesses are ripe for opportunity where they're simple businesses to get in. AI is never going to clean your building. Sorry. It's just never going to happen. Insurance sales, right? Insurance sales is a very simple business for people to get into. It has a low barrier of entry and you can kill it selling Medicare. I know a guy in Medicare. He makes$14 million a year selling Medicare. Crazy. He's got 2 ,000 downline people, you know, and he's a great guy.
28:32Jason Mickool: Do you personally own any other unsexy businesses? I do. I own a restaurant. The worst business you could ever get into in your life. How does it do? um it's terrible it's amazing you should come tonight you guys should come i'll buy you dinner the food is incredible the service is amazing i heard a celebrity chef last month i lost 100 grand the margins are like so thin it's the it is so complicated i don't i don't go there and like wait on people or do anything i'm not that involved um but it's terrible it's a terrible business. I own the Take the Power Back. And Take the Power Back is really a passion product.
29:13Do you know what Handshake is? You know what Handshake is? Oh, I hate these people. I know what a Handshake is. Yeah. Handshake is the website that probably where you guys went to school, when you applied for a job on your website, it was actually Handshake behind it. So it's the infrastructure that students apply for jobs. I hate these people. They're the worst humans in the whole entire planet. I want them to hear it. If you guys hear this, you hear it loud. Why is it? I'm going to tell you. They basically are the intermediary between the school and the employer. What they do is they give the power to the career services department to decide which school, which jobs the students should be applying for.
29:57Can you imagine that? Have you guys been to a career services department? Thankfully, no. I didn't go to the one when I was in college. I just didn't go at all. I was like, I'm not doing this. It's worse than you could have possibly imagined. I'm sure. You've got a very low level person who makes no money, who thinks all rich people are stupid, probably, you know, political aside, not on the entrepreneur side. And they're saying we don't allow 1099 jobs, right? We don't allow jobs that are commission-based. So there are schools out there that I'm not allowed to post my job when I can introduce you to thousands of millionaires in financial services who started with nothing, right?
30:37That have 20 and$30 million businesses, but the career services department has decided that I'm not allowed to put that on there, which is like, it drives me bonkers. So I started this business called Take the Power Back. And I do, I basically, it's a job board for, I don't make any money at it. I don't care about making money at it. I'm just trying to make a difference. And it's, I do a podcast for, to try to inspire Gen Z, right? And it's a job board. And then we have a speaking bureau. So, you know, if you're, if you're part of a group or club organization, you can basically go and you can, you can request to have a successful person speak.
31:15And then it's an incubator, meaning my friends and I will give money to people that want to be able to start a business, young people that are looking for, you know, advice and or capital that they need in order to scale a business. I own U.S. property insurance. I own McCool Properties. We do real estate development. I own the restaurant business. We've got all kinds of stuff going. Real estate or the stock market? Real estate. Why? Because you can get the leverage, right? And ultimately it pays for itself. If I can go, if I get 200 grand and I can go borrow a million or a hundred grand, whatever the number may be, and somebody else makes the mortgage payment, yeah, it's a little bit of pressure, right?
31:54But ultimately what you're doing is a cap rate. So a cap rate is what you pay for at times your net profit, right? Before debt service. So when the debt service is paid off, you're gonna get a six or 7 % dividend plus the appreciation of the growth and then you can leverage it. I don't think the stock market is where people get rich. The only people to get rich are the people that are selling the funds or the strategies of, right, of the people that are buying. But the people that are buying it, you know, you can't accumulate enough money, right? You can't accumulate enough money to build generational wealth by saving just one stock at a time.
32:34I want you to let me know if this statement's true. People say that the first generation that makes money is the hustler, you know, they're the generation that comes into money. The second generation keeps the money, they maintain it. And the third generation, they destroy it. Have you found that to be true? No, I don't find that to be true. You know, I find it all has to do with who you hang around with in whatever generation that you are. It's about leadership, right? It's about good parenting. But ultimately, you know, I've had people that have come to work with me that came from very wealthy families, right?
33:10You know, and they've been lazy. I've also had people that come work for me that have come from wealthy families and they're animals and they've built twice the wealth of their parents. Right. So I don't think that really has to do anything. I think the decision that you make in terms of who you surround yourself with will dictate the behaviors you are as an adult. So your parents get you to a certain point. Right. Now, if you're a rich kid and you end up hanging around with a bunch of druggies and trust fund babies, well, yeah, you can become a loser. But if you're a rich kid and you end up being in a culture and environment where people are trying to win and grow and become better and they're building wealth for themselves, that's what you become.
33:48You are who you surround yourself with, right? One of the advice I give to people all the time is don't hang around with losers. And you know who they are, right? And if you don't, you're probably the loser. Who you associate with is just as important as who you don't associate with. 100%, you know?
34:06Jason Mickool: John Morgan, who's not too far from here. The Morgan of Morgan. Yeah, Morgan of Morgan. We love John Morgan. He's a great friend of ours. And, you know, he says that some of the greatest piece of advice he ever received is that your children are one bad friend away from total disaster. Great advice. So true. They're also one good friend away from making a difference in their lives. Couldn't agree more. You know, that's the, and I think that's the opportunity. We need to spread that word is to say, go find the group of people that are out there and surround yourself. Hey, go get around the McCools.
34:40Come to us. I mean, we hire kids out of college and we make millionaires. Like we're kingmakers. So it's because you're attractive to money though. What is that?
34:48Jason Mickool: You're attractive to money. I'm attractive to money. I think so. I don't know. You got to say it with a smile on you. I like it. I like it. I'll tell you, Jason. And so this is a, I don't know if we coined it, right. But we have kind of this saying about people, right. Where like, you can just conversate with them and obviously see their track record. And it's like, that guy's just, he's just attractive to money. Yeah. Right. Like, you know, we've been getting, you know, more investment opportunities recently. We're about to buy our third investment property, real estate. And, you know, the people that we partner up with were like, you know, that guy's attractive to money.
35:18Jason Mickool: You know what I mean? So it's a compliment for sure. Well, you guys get, you guys have something really unique. I think you probably know this, but you need to monetize your interest score in a different way. What do you mean by that? You know, you've got fame, right? And, you know, fame doesn't mean money. Fame just means opportunity. Because like you said, things are coming towards you on a left and right basis, you know, and what you got to do, it's my opinion. So when you want to take a quantum leap in life, right, you need – two things happen when people do that. They usually are provided new information, right?
35:53Or there's a relationship, a new partnership that they're able to form. So you think of Grant Cardone, right? Why is Grant Cardone so rich? Is it because of Grant Cardone? He has a 50-50 partnership with a guy that was a real estate guru. Okay. Right? So Grant used his fame. I know Brandon Dawson. Dawson. Is that Dawson? That's Dawson. That's right. So Dawson is the guy who brought the real estate.
36:18Jason Mickool: Hearing aids, right? He sold a hearing aid company, I thought, for like$150 million or something like that. I think so. Yeah. But where the real estate came from is Dawson. Okay. So Dawson is the real estate guru in that relationship. So Grant doesn't know a lot about, I mean, I'm assuming he knows a lot about a lot of things, right? Very smart guy and he's a very talented guy. He's a marketer. He's a marketer. That's right. He brought, and what he brought to the table was, Dawson brought to the table was the REIT and the infrastructure associated with it. Grant and I have been going back and forth of starting Cardone Financial Advisors, which would really be Florida financial advisors.
36:54So he would use his fame to be able to brand our company. So we would have a business partnership where he would bring in leads of people, right? He would have an infrastructure, but we would really be a private label for him.
37:09Jason Mickool: Do you know Robert Duggan? I know the name. I don't know why I know the name. Okay, because he's also done speaking with 10X and we had him on yesterday. He's a pharmaceutical billionaire. He's worth, I think, 10,$12 billion or something. Crazy. That's a crazy amount of money. But that's where your opportunity is, man. You guys could all leverage your brand, right, to put people into business slots, right, that has an infrastructure by partnering. That's your quant partnerships. Yep. Definitely. Remember, you know, 25 % of something is better than 0 % of nothing, right? I mean, that's the reality of it.
37:45Because you have so many, and what you're doing is making a difference, you know, and making a difference in the lives of young people that look up to you guys because you bring those. Well, you can steer that into a really great business for yourself.
38:00Jason Mickool: What's the saying we always have? It's better to have a slice of a watermelon than 100 % of a grape. amen to that amen to that that is a true statement jason how many cars do you have 11 i i i say that reluctantly because i have two being built right now what cars do you have ah jesus you know let me list them out tell us some of your favorite ones you have i you know i have a phantom i just got my wife and i um i had bought i bought her a cullinan i had a ghost and I bought her a Cullinan last year. And the Cullinan and the Ghost were kind of two similar, two big cars, right? So then I got a Spectre and I hated it.
38:40So then I was mad at the dealership and I have the Phantom that you saw outside. So we have two really nice Rolls Royces. I just have to go through my garages. Then I have a bunch of classic cars. I got all Restomods. I got a 69 Camaro SS. I've got a 59 C1 Corvette. You ever see Kevin Hart's Corvette? Yeah. Yeah. So I built it just like his, except black with gray.
39:10Jason Mickool: It's badass. Can you tell us a story about how significant one of those purchases were? Because you hear all the time about, you know, people, you know, sold a company for$70 million and they went out and got their first Rolex or something like that. Do you have a story behind one of those car purchases that you bought? Yeah, yeah, yeah. The one that means most to me is a 911. 11. My dad was a nine 11 fanatic, always wanted one. I, if he was alive, I would have bought him five right now, you know, but he, but he passed. So that was my first big deal. My first big car was my, was my nine 11. Um, you know, and that was just today.
39:45I'm like, that's not, that's a nice car. It's okay. Um, but that was the, that was my dream car. Cause it meant a lot to my dad.
39:51Jason Mickool: And at what point do you think people should start spending money on their lifestyle? Wow. Like, do you kind of have a typical rule of thumb where it's like, hey, you know, you should have this much money in the bank, this much passive income? Like, is that kind of your rule of thumb now where it's just don't finance it? You know, when you buy in a depreciating asset is really stupid. Right. So I wouldn't go make three thousand on a month payments no matter what. But if I had enough money and cash flow coming in and I could pay cash for it, you know, I get paid quarterly today. I think I think today is a payday for me.
40:22It's like four point nine million dollars. um you know i'll usually go buy a car or you know a watch or whatever it may be decent payday different payday yeah 90 days later 90 days later it comes rolling in again so you know i always we we rented a um we rented a 120 foot big mega yacht out of miami with a few of our friends and wives and you know just took a four-day trip i was like well i'm gonna do something with this money what what are you going to do with it? Right. So we just kind of throw money around with that stuff. We got to play a quick game. All right. Okay. We, we, we gotta, we gotta do a rapid fire section for you.
41:00Okay. Is work-life balance real for someone trying to build a hundred million dollar company? No. Work-life balance is actually never real. Um, it's a, it's a state of mind. Right. And if people say, you know, if you love what you do, you never work a day in your life. That's bullshit too. Right. It's called coping. Meaning, you know, um, if you ask me how hard I work. I don't really work at all, I don't think, but I'm constantly working, right? So when I get in the car, I'm going to be on the phone all the way home. I just got to have an executive team meeting. Then I'm going to go head over to the restaurant and go yell at a couple of people.
41:31Then I'm going to go do emails for an hour. Then I'm going to go play nine holes of golf, you know, like it's, I just think you can't. So no, you have to keep working. Not work-life balance is work-life integration. That's actually, I love that. Stealing that from you, Josh. A 25-year-old has$100 ,000 cash, real estate, index funds, or starting a business. Where does the money go? Starting a business, no question. You can't build wealth. And you're either an entrepreneur or an intrapreneur, right? Do you know the difference? One works in the business. One is owning the business. One owns the business, but you can do both, right?
42:03So if you're an intrapreneur, I mean, you have no capped ceiling in terms of your income, right? Or you get stock in the company that you can actually cash out someday. Real estate businesses, insurance businesses, financial advisory businesses, that's where you should go spend your time. Someone making$500 ,000 a year buys a$200 ,000 car. Smart reward or stupid financial? Stupid. Stupid financial decision. Come on, man. You know, you're broke at$500 ,000. Last one for you is you meet a 22-year-old making$300 ,000 a year with no college degree and a 30-year-old doctor making$300 ,000 a year with$400 ,000 in student debt.
42:42who made the better financial decision. I don't even want to, I can't imagine being a doctor. What a terrible, it's about, it's a great profession to help people, but they're underpaid. They're over litigious. They're over sued. And they really don't have a lot of upside. Now you can take that and you can go start your own business or create something. And I think that's amazing. But the young 22 year old, and that, I mean, that's what the takeaway is, right? When knowledge is free, what are you paying for in a university? Right? That is not okay. in this day and age. And some days we got to smarten up and it starts with the parents smartening up and not saying, I'm going to go give you a$50 ,000, you know, liberal arts degree and get instead take the$400 ,000, invest in a business, right?
43:26Buy some real estate, get the kids some coaching. Let's get them to work. How would you change the education system? I would, I mean, it's, I demolish it candidly. I would stop teaching.
43:40Jason Mickool: I love how to see. I mean, I would. I would demolish it, right? I mean, 70 % of adult learning is experience, right? So what happened to trade schools? What happened to, why don't you, instead of sending them into school, we're talking about doing a program for high school kids where they can come right out of high school and they can come work and be on a financial advisor for four years as an apprentice. So that to me, you know, the kid will get out of school, quote unquote, he'll have a series seven, he'll have a license, he'll have worked in the business, he'll understand more. about financial literacy than people that are in there 40 years old, and they're going to build an amazing career.
44:17Like do that, right? Do that. Let the kid get paid minimum wage or whatever it is that you have to do, but give the, give the person a shot. Don't teach them how to read and write. And like you can, I mean, reading obviously is important, but writing skills, you need, you don't need writing skills anymore. Are you telling me that learning algebra and solving for Why? Didn't help you build a$100 million company? No, sir. Did it? No, sir. It did not. And I don't think it will. What's cool about AI is the knowledge, right, is not the differentiator between people's ability to be successful anymore.
44:53What's cool about it is, is the person that can go take that knowledge that's already in front of them and then go do shit with it is a race to being worth hundreds of millions of dollars.
45:03Jason Mickool: Jason, you said if somebody has$500 ,000, you consider them broke. I consider them broke. So at what point financially does somebody have fucking money? Does somebody, like, is somebody, at what point is somebody wealthy? Yeah, I think that's defined differently, right? I think, like, FU money is if you have a net worth,$250, you know, I think you're kind of, you can kind of do whatever you want. Yeah. $250 what? Million. Yeah, yeah. I think that's a million. I think that's$25 million. You know, you could have a bad summer and blow$25 million.
45:45have you seen something like that happen i not personally but i you know you you see it you see these athletes who get these big contracts and they're just i think like odell beckham jr was like on a podcast one time was just like yeah i've made over 100 million dollars in my career that's not a lot of money he's just he's just he's like he's like man like you guys don't understand we got agents and we got taxes and he said he was just basically saying that this like yeah i've made a hundred million dollars but like i like are you telling not really are you telling
46:12Jason Mickool: us you're worth more than 250 million uh yeah i mean it's like you know that's uh um it's one of those things where it's not really the money net worth that matters right the the the fu part of it comes for me personally is from the cashflow. Right. Right. So the business still drips me, you know, 20 million a year. Yeah. So I want to talk about something he just said right there, though. Taxes, business owners, number one expense. Do you have any tax hacker tax strategy for anybody trying to? Yeah, I got a bunch of them. So, um, we do, we do, there's two different, there's real estate type of businesses, right?
46:52When you think about real estate, I'm considered a real estate dealer. Most people don't think about a real estate dealer.
46:59Jason Mickool: You're the professional. I'm the professional. So no, so there's professional, right? So that means you can deduct the depreciation of the asset. A dealer gets to deduct the basis of the purchase. Does that make sense to you? So if I buy a million dollar property, right, I actually deduct a hundred percent of the million dollars as cost of goods sold. So now when I sell it, I recognize it as an ordinary income. But I can keep doing that. So I buy real estate like crazy. We bought the building for the restaurant. It was$2 million. Why? Because I'm eating away sales of other properties that we had that are recognized as$2 million of ordinary income.
47:40So that's a hack. We've had properties that haven't sold. you know how do you how do you claim to be like a real estate dealer yeah you have to buy and sell properties regularly and develop them so i don't do flips right um we do developments i'll buy a piece of land we'll build a house on it takes two years so that that all that money that went into that property has been now is coming off my income so all of that and all of the expense that goes in there and all the expense of running that business, flying private, you know, having trucks and cars and all of that stuff just gets buried inside of that business, which is, which is, you know, kind of a tax hack, um, a little bit.
48:22That's why most really wealthy people are in the development business because you, it eats, you're building your net worth while you're eating away your taxes all at the same time.
48:31Jason Mickool: Jason, we like to end these podcasts off with two questions. I'll start and Jack will finish it. I first of all want to say this was an incredible conversation. Was this a good conversation or what? I loved it. I love how raw you are. You guys have to say that. No, no, no. It's very entertaining, honestly. I typically don't even say this before the podcast ends until the at very end, but like this is genuinely, this was class. Oh, thanks, man. I appreciate it. This is great. I appreciate what you do, brother. Thank you, my man. You too. I appreciate that. I'll start us off here. Jack will end.
48:58Jason Mickool: But Jason, if me and you were to die tomorrow and you could leave one last message with the younger generation that's watching this right now, you're doing a lot of work. You're giving back to Gen Z, but if we could give them one more message. With all the experience, the knowledge, the wisdom, the pieces of advice you've had, what's the best message you can leave with the younger generation? Don't listen to your parents, right? Unless your parents are telling you to go bet on yourself and be an entrepreneur, then don't hear it, right? Go surround yourself with somebody who's done something big and then go copy what they did.
49:26And Jason, when it's all said and done, how do you want to be remembered? I want to be remembered as somebody that's helping Gen Z become entrepreneurial, right? That's the way that is to me, the, you know, I think the Charlie Kirk thing as in general, he was, it was interesting, but it was terrible for what it did for the perception of people in my age. They basically made, he just kicked puppies. That's all he did was take stupid people and he's a brilliant man and he just made them look so damn foolish. And then all of a sudden that painted the generation as these liberal people that don't want to work and that are really screwed up values.
50:04That's not true, right? What I have been able to see in my life is that the young generation adapts to the surroundings that they have, right? So what we have to do as people in America, I want everybody to remember me as the person that said, hey, let's provide some leadership. Let's provide some vision and let's believe in that generation, which you guys are doing in an incredible way. And I can't thank you enough because it's carrying that message and you're actually reaching them right at the heart, which has given them the platform
50:37Jason Mickool: to see what's out there and available. We appreciate that, man. We appreciate your time and thank you for the great conversation. Thank you, my friend. Appreciate it. For everybody tuning in right now, be sure to like and subscribe for amazing content, amazing episodes coming every single week to the School of Hard Knocks podcast. We're bringing on the 8, 9, 10, 11-figure entrepreneurs that you see us interview every week on the School of Hard Knocks. We're going to put the link down in the description for you guys to get access to follow along with Jason across all of his social media platforms, along with check out his company and the great stuff that he's building.
51:06Jason Mickool: And lastly, we're gonna put a link down in the description to join the number one community for entrepreneurs in the entire world, the School of Mentors, where every week, we host live calls with the eight, nine, 10, and 11-figure entrepreneurs we interview on the School of Hard Knocks, where you ask your questions directly to them. So we can't wait to see you on the inside. With that being said, we'll see you in the next episode.
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Jason Mickool is the Founder and CEO of Florida Financial Advisors, a financial services business he started from his kitchen table after years in corporate leadership and repeated firings.
In this episode, Jason shares his philosophy on ownership, uncapped income, recruiting, real estate, entrepreneurship, building scalable businesses, and creating generational wealth. He also explains why his wife pushed him to bet on himself, how he thinks about risk and cash flow, and why he believes the people you surround yourself with can determine the trajectory of your life.
Follow Jason:
Website: JasonMickool.com
Instagram: @jmickool
LinkedIn: Jason Mickool
Florida Financial Advisors: Florida Financial Advisors
Take The Power Back: Take The Power Back
Greatness Lab: Greatness Lab
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