
From Broke to Six Figures and Back: Jason Brown on Options Trading, Risk and Rebuilding Wealth
Jason Brown turned a $10K student loan into six figures, lost $250K on one trade, and rebuilt. He shares his options, risk and wealth roadmap with Ryan
- Jason's first professionally managed account turned $2,000 into $700, which pushed him to learn to trade himself with the remaining $500.
- His first profitable trade came from spotting a repeating price channel in Sprint stock between $4 and $5 — pattern recognition before fundamentals.
- He grew a $10,000 student loan refund into roughly $113,000 by age 21, then to $300,000, then lost about $250,000 on a single trade.
- The core mistake was having no 'I'm wrong level' — a predetermined exit point — and no put options in place to protect the position.
- Read the stock chart first to see if a stock is in an uptrend, downtrend, or sideways, then use fundamentals to explain why.
- Options let small accounts control higher-quality stocks and protect against losses, rather than waiting decades for compounding.
- Vet a financial advisor with actual knowledge: Jason passed the Series 6, 63, and 7 and found the role was selling pre-packaged funds, not managing money.
- The Five-Year Millionaire math: $4,000 growing at 10% a month over 60 trades gets to roughly $1.2 million, but only with education and paper trading first.
- Free Stock Market Starter Pack and Stock Option Starter Pack PDFs are available at thebrownreport.com.
so I spent $200 on some Jordans. I was like, if I lose this other $500, at least I got some gym shoes out of the whole deal.
I was risking a quarter million trying to make half a million. I was actually up $100,000 in that trade before it went against me. And I remember saying $100,000 is not enough. I'll never say that again, by the way.
I didn't have an I'm wrong level. So I didn't have a level of say, hey, if this goes against me, when am I going to get out?
Look at the MAG7 stocks and just follow the money. Money is going into AI, infrastructure, cloud, storage, data centers. I would tell people to look there, at least at the time of this recording. You don't win by following the playbook. You win by rewriting it. 700 episodes deep with the people who actually built something real. No theory, no fluff, no shortcuts. This is Right About Now with Ryan Alford.
What's up and welcome to Right About Now. We're always talking about what's right and what's now. We can talk about last year, we can talk about next year. No, we're not about the windshield looking too far ahead. We're not about the rear view mirror looking too far behind. We're actually about taking notice of what's here, what's now, and how to get ahead in business and in life. And that's why we bring all the experts. We got my friend, my buddy, downtown Jason Brown. I gave him a name he didn't even ask for. That's what I do, Jason, but welcome to the show. Ryan, good to be here, man. I love it. I love it. I receive it. Good. I appreciate that. Some people are like, I don't think they know how to tape me.
I give everybody pet names. It's love. I don't know. It's just what I do. I love what you're doing, Jason. Little options trading. Power Trades University, author of five-year millionaire. Damn, I'm going to be a five-year. Yeah, everybody likes to get in a hurry, but five years now is pretty good, Jason. It's a good, reasonable time frame. That's why I like it. It's doable, and it's not 40 years out. You're not looking at retirement. It's within your lifetime where you can still enjoy it. I know. Hey, man. I had student loans, and I wouldn't say I used every dollar wisely. Some might argue using them for college isn't even wise, but we'll save that topic for another day at another guest. But no, no. I got the attention of taking out the student loan, throwing it in the stock.
It actually seems smart. It's like, at least you're going to get a higher return. You would have hoped. I'd love to start there a little bit, Jason, and then building towards what you're doing with Five Year Millionaire. Yeah, absolutely. So what happened when I was growing up, we were poor, sleeping in sleeping bags, and I was trying to figure out how to change our family's financial tree. And I actually took $2,000 to a bank at 18. That was my graduation money. And I said, like, I want to invest. The girl asked me, like, why? I was like, I want to be rich. Like, why else do people do this? And so basically she said, you want aggressive funds. I'm like, yeah, that sounds about right.
I need aggressive growth. And I'm thinking, OK, I'm going to come back two or three years later. I'm at $6,000. You hear people say, just put some money in, leave it, come back, it'll grow. Yeah. came back about two, three years later, and it was down to $700. And so they lost majority of my money. They lost $1,300. So I'm like, I could have lost my own money. What happened? And pretty much, she's just like, I don't know what to tell you. Market goes up, goes down. I was like, I know what to tell you. Give me my $700. I can do this myself. And so I spent $200 on some Jordans. I was like, if I lose this other $500, at least I got some gym shoes out of the whole deal.
You know, I got something to show for that money. Yeah, your own heart. Right? Yes. I had 500 bucks. I'm working for Sprint PCS making $8 an hour. I make 64 bucks on a Saturday, $50 after you take out taxes. And I was like, I could just make 50 bucks with this $500. I wouldn't have to work a weekend. What I did was I bought Sprint at $5. It fell down to $4. I was like, oh man, I'm not that good at this. Maybe I'm not as smart as I thought. Sprint went back up to five. I thought, OK, I just need to go to 550. It fell back down to four again. I thought the stock market's rigged. That's why they asked for your Social Security number.
They won't let it go to 550. I just had all these thoughts. It went back up to five. And I said, I've seen this before. I got out at five. It fell to four. I got back in. It went up to five. I got out, made my first hundred dollars. I tell you that story because that was the first time I started to learn about patterns. If you drew that out on a paper, it would be called a channel and stock pattern. So I got really good at these patterns and start studying what other patterns there were. And I said, how do I get more money into the machine? And so I had a scholarship to school, the Mike Illich School of Business, Wayne State University here in Detroit, Michigan.
And I knew that I went and saw financial aid. I saw my buddies getting student loan refunds. And I found out that because I didn't live on campus, she was like, oh, you can use the money to live on campus. I said, well, what if I live at home? She's like, well, you could move on campus, use it for living expenses. So I'm like, basically I can use it for whatever I want. And for me, I saw that as an opportunity to get more money into the stock market machine. So I took that $10,000 student loan and I grew it to like $113,000 as a 21-year-old college student. Amazing. What a great story that would be if that was the end.
But I think there's a part two coming. There's definitely a but to that, right? Because what happened was I dropped out of school after that. I made more money not being an engineer. And then I grew the account to about $300,000. And about three years later, at about 26, 27, I actually risked a quarter million trying to make half a million and I lose it all. So by the time I'm 27-ish, I'm flat broke, had to move back home to the neighborhood with drugs, gangs, bars on the window and really reset. But that's where this whole new Jason Brown was born. That's when I started documenting my life and saying, like, I know the stock market works. I've made money from it before. I just got to figure out what I did wrong.
And that's kind of how I got into YouTube and teaching. And I was rebuilding my account and kind of recording and documenting the whole process along the way. Hey man, I admire just the gumption of it all because I love people that take chances. You're watching your surroundings. You maybe not have known everything and we don't always know everything, but you're watching, Hey, people are investing in doing these things. You get interested, you put 2000 in the bank, you realize what a facade that is. And what happens is you get put into one fund where some guy that gets paid 30 grand a year, pays attention to it for about 10 minutes a month. the aggressive value fund here at Liberty Mutual Bank. Well, I'm making up bank names, but I mean, I could see it.
And we'll get you in the aggressive fund, son. We'll get you in that one. We'll see how it goes in a couple of years. Yeah, how it goes. Oh, I remember starting in school and they want you to get in the 401k plan. They give you four boxes to check. And it's like, I'll give you, I took that aggressive one. I don't think it went as bad as yours, but it didn't go wonderful. Then I realized, okay, I can diversify this thing and do it like I want. But admire, again, you're wanting to get ahead. You're wanting to do the right things. You're hearing the signals. This is how you do it. And then you earn it up and you took a little bit of the slow path.
And it sounds like you got a little greedy. And I'm just going to say, I don't know. I mean, every detail of that. But maybe it was oversold to you, misrepresented. There's probably a lot of details to that. But it sounds like maybe you tried to get in a hurry. When I saw the opportunity with the stock market, I counted $300,000. When I started to lose it, there was a lot of different things wrapped up into it. A, I did get greedy. I was risking a quarter million trying to make half a million. I was actually up $100,000 in that trade before it went against me. And I remember saying $100,000 is not enough. I'll never say that again, by the way. But at that moment, I was like, $100,000, what am I going to do with that?
Because I was trying to make half a million. In my head, I was trying to make half a million in one. investment. Not really, I could have made a hundred thousand four more times, but that was part of it. One of the principles I learned from it that I talk about in my book, Five Year Millionaire, is that I didn't have an I'm wrong level. So I didn't have a level of say, hey, if this goes against me, when am I going to get out? How am I going to save my account? I didn't have any protection. Now I talk about how to use put options as protection. It's like I should have took a portion of that money and protected that quarter million. I didn't.
I just thought it's going up and I'm going along for the ride, never thinking that it can go down. So It definitely humbled me, but I wouldn't be the same guy I am today if it went right. Number one, you wouldn't like me because I'd be super arrogant, think I knew everything. But number two, when the times get tough in the market, I'd realize I didn't really know anything. I don't think I knew as much as I thought. I was just riding the wave of the market going up. And I think a lot of people invest like that. They get a little bit of success, but they don't really know what they're doing until they've been through an up market, down market and a sideways market.
Tariffs, COVID, all that. Yeah. No kidding. Talking with Jason Brown. He is a stock market expert, options trader, and author of Five-Year Millionaire. So Jason, we got the good, the bad, the ugly, and we came on the other side. This is the quote from the book, the roadmap for investing in the stock market, wealth accumulation, and financial independence. We want that plan. Yeah, the plan starts with you got to be educated. First of all, everybody wants to invest in the stock market, but it's hard to invest if you're not educated about how it works, when to buy, when to sell. And the first thing I tell people, or at least the roadmap that we talk about in the book, It's number one, you got to have an account.
You got to have access to the market. And we want you to practice before you ever put real money down. But then that goes into the education piece because it's like golf. If you don't know what to practice, you start to develop a bad swing. You want to be educated to the point of what am I practicing and how do I know I'm practicing in it the right way? And the steps you want to take, or at least that we teach, is number one, you want to be able to read stock charts. A lot of people start with fundamentals first, but the reality is if I look at a stock chart, I could tell just by looking at, is the stock in an uptrend? Is it in a downtrend?
Is it in a sideways? If it's in a downtrend, then I can go look at the fundamentals and find out why it's in a downtrend. If it's in an uptrend, Then I can go look at the fundamentals and find out why. But initially, that chart is going to tell you if you're in a stock that's going up, going down or is going sideways. Then from there, just taking a look at the fundamentals and saying, like, well, why is it going up and why do I think it's going to continue to go up? And then the third piece of it is using options to supercharge your results as well as protect your account. Most people don't get excited about investing because they say, oh, I only have 500 bucks.
I only have a thousand dollars. I only have four thousand dollars. That's not going to do much. And depending on who you're talking to, some people say, oh, just put, keep adding money to it. And over time, it'll grow. But if you understand options, you can actually control some of the higher quality, better stocks and get an exponential return, even with a little bit of capital. So it's really key to learn about call options and put options and how you can supercharge your account as well as protect it from losses. Talk to me, Jason. I'm going to play. I'm not always like devil's advocate. That's not the right word here, but more. I try to play reality. You and I would probably think we're probably cut out of similar, similar cloths being aggressive, wanting to make our own path, that entrepreneur type spirit.
Some people just don't want to take the time to learn it. As crazy as that might sound, and it might sound lazy. It looks like Chinese checkers or something on the board. How do you navigate this? Is that just when, hey, you need to find a good financial advisor that you trust? Or is it stop fooling yourself, learn this stuff. It's important. Get over it. Which one? It's both and, to be honest with you. And I would never shun someone who doesn't want to learn this because you do have to have an interest. I don't have to say you have to be passionate about it, but you have to have an interest to want to know how do I grow my money? You know, what are they doing with my money versus just me signing this paper and I'm sending me a statement every month that I don't know how to read?
So you have to have some interest. And I think it's very important that we're not trying to take people who aren't interested in the market and make them interested. If you're already interested, we're saying, hey, here's a roadmap and a blueprint to help you get better and understand it. If you're not interested in managing your money, you are left to finding a good financial advisor or a person you're trying to. trust. I think what's important there is that you understand no one's going to manage your money like you are. So just make sure your expectations are in alignment. People say, well, I don't really want to learn it. I just want to give it to somebody and I want them to give me the 100% returns or the 50% returns that I see sometimes you make.
And I said, unless you got a 10, $20 million account, your account ain't big enough for someone to focus solely on you and your money and to grow it like that. They're going to stick you. You got 100. I'm going to check that box at the end of the sheet. Yeah. And they're just going to stick you in some fun, right? And go find 100 more people like you because they only make 2% off of it. In order for them to make their living, they just got to find a bunch of you who don't care. Just as long as your expectations are aligned. And I think the other thing that's a little bit dangerous about that is people say, I want to find someone I trust.
But how do you know who to trust if you don't understand it yourself? And most people don't have an answer for that. They say something like, oh, this person went to school for it. Going to school does not equal trust. Going to school just means you know how to pass a test. Taking a series 6, 63, or 7 just means you know how to pass a test. I found when I went to study to become a wealth manager, I studied to become a financial planner. planner past the six, 63 and the seven. And right before we filed it with the state and the SEC, you got to get sponsored and all that stuff. They wanted me to shut down my own website. They said, I couldn't talk about stocks anymore.
Then I said, OK, no problem. How does it work? When do we actually pick the stocks and help people? Oh, we don't pick the stocks. We pick from these three different funds from American funds, Fidelity. And I forget who the third company was. It was like, oh, they just supply everybody these funds and they change one letter or one ticker symbol. And now it's like our custom fund. I'm like, so we don't even manage the money? Like, no, like you just got to be licensed in order to sell these securities and make a list of all your friends and who's their financial planner or who they use and see if you can bring their account over. And I thought that's interesting because people would have thought they could trust me just because I had a license and I wasn't even managing the money.
I was basically a licensed sales rep. You have to have a little bit of interest in this and you have to be educated enough to the point to understand how do you even pick somebody that you trust and is knowledgeable. Yeah, good advice. And I'll say this, as you were talking, Jason, I was thinking back to college or to my education. Why are we teaching sixth graders this? We should have another finance and stuff once you get in college and even high school a little bit. But we should be teaching our youth this from the get go. I mean, should we get financial excellence in sixth grade? I feel like we should be starting earlier. You know, that's interesting conversation. I got so many thoughts around that.
You'd have to make it corrective for that. We should be introducing this stuff earlier. There's so many problems with trying to do it. You got the parents who don't understand it, so they can't help at home. You think there are 10 hours of rejection? Come on, man.
My wife's a principal and was a math major. Daddy's pretty good at a lot of things. Mommy's going to have to help you with that math. Look, send them same kids home and be like, we want to buy some stocks and invest. The parents are like, what? Huh?
True. But yeah, there's a balance there, but I'll let you finish your thought. The school's trying to cater to the average student. So maybe in affluent neighborhoods or unique schools, able to introduce some of these extracurricular or non-traditional learning paths. But when you try to look at school as a whole and they're trying to teach a broad spectrum of kids, I just don't think they have the bandwidth to introduce investing and investing concepts, A, if the teachers don't understand it themselves. And then B, they're trying to just kind of block blanket, teach it across all students. Although I believe all the students could learn it, I just don't know that the schools are ready to kind of take on that task. I like big challenges, Jason.
I like big on it big. Hey, we're doing enough of the same shit for too long. My wife, she's middle school principal, talking about a tough job. She agrees with it, but it's more than she has. She's got enough problems that I'm like, man, we keep what they say, stay the same, stay the same. There's something there. There's a balance. I don't know if we're going to solve that today, but it may be. No, I think there's a huge opportunity there, though, for sure. If we had Financially secure, at least knowledgeable kids in those areas. And maybe it's not stock options, but it's something. I mean, just teach them how to use credit. You know, let's start there. Let's teach them how to balance a checkbook or create a spreadsheet with a budget.
The whole gamut of financial literacy is just missing from school at an early age. Teach them how to pay taxes. Most kids probably don't even know that they don't even get to keep 100 percent of their paycheck. especially if they started a business. There's so many things in the financial literacy space that could be taught in schools. But like you said, I don't know that we go solve that today. But maybe, maybe somebody's listening and we go create some type of cool partnership. There you go.
As we close out here, Jason, talk to me about the Brown Report. How do people, what's the first step here, both with you and in general, how you guide people? Power Trades University, I know we got that, but walk me through some practical steps for our audience. Yeah, there's two things that we like to start people off with. So at the Brown Report, we have the Stock Market Starter Pack. Those are for people who say, I don't even know where to open an account. I don't know how to read a chart. I don't know what I'm looking at. I don't know how much money I need, how much I want to make. And the stock market starter pack, we walk you through all that, how to get your first account open, how much money you need, how much you can expect to make, how to read the three most profitable chart patterns.
And it's completely free PDF download. The second one is the stock. option starter pack. So maybe you've already been investing, but you want to know how to supercharge your account or your returns, as well as protect it when the markets dip or learn how to make money from stocks in the market falling. We got the stock option starter pack. So both of those are available at the brown report.com. One of the best free resources to get anyone from a beginner to someone who's even been experienced to the next level. I love it, man. I mean, what's realistic if someone coming in, they said they don't have a million dollars and how to become a billionaire in five years, but like or a multimillionaire. What's realistic year one following something like this?
And no guarantees, you can't control everything, but generally speaking. In my book, Five Year Millionaire, I break down how you can start with $4,000 and if you can earn 10% a month for 60 trades or five years, you'd actually have $1.2 million. Most people think to become a millionaire in five years, they got to start with 100,000 or they got to start with half a million. But really, if you can start with four thousand dollars, you could grow it to a million, 1.2 million in five years. When you say what's realistic, I like to answer that two different ways. What's realistic for people who are knowledgeable and what's realistic for people who are not knowledgeable? When people are not knowledgeable, they don't believe you can earn 10 percent a month.
Most people don't make 10 percent a year in the market because the S&P 500 returns on average 11 percent. For those of us who are using options, reading stock charts, I have those trades where I earn 10, 20, 30, 40, 50 percent a month. And so that is realistic, but it's not realistic without knowledge and without practicing and without learning the industries. I know that 10 percent is doable. And what I love about. What we do, all our trades are recorded. Everything is time-stamped. You can go back over the years and say, do these trades really make 10% on average a month? Do a segment on the Charles Schwab Network live from the New York Stock Exchange. I do a segment called Three Stocks, Three Options.
Those are public stock picks that I give with the option trade. You can also go see those trades and see like, whoa, It went up 50 percent. It went up 30 percent, 20 percent in a month or in two months and average 10 percent. Knowing that is possible and then getting the knowledge. So I think you can realistically expect 10 percent a month, but you have to grow until that 10 percent a month. You set an open account. You got to learn. You got to practice. Fair enough. Lastly, Jason, any hot stock tips, anything on the radar that somebody should be aware of? I like to say, follow the money. At the time of this recording, the money is going into AI, is going into semiconductor stocks, is going into cloud and storage.
Right now, follow the money. The simplest way for most people listening, look at the MAG-7 stocks, you got money. Microsoft, who's crushing it with their Azure cloud services. You have Apple, who has yet to do the Siri refresh, but they also haven't really made their big splash in AI. But that stock's moving higher. You got NVIDIA, who's just crushing it, making the chips and building data centers. Look at the Mag 7 stocks and just follow the money. Money is going into AI infrastructure. cloud storage data centers, I would tell people to look there, at least at the time of this recording. Jason, jam-packed action value all in one. Where can everybody learn more? You mentioned it, thebrownreport.com. I think I heard, but give those digital digits.
We're the digital... locations. The best place is thebrownreport.com. From there, they can connect with me on LinkedIn and connect me on Instagram. I'm thebrownreport on Instagram, thebrownreport on YouTube. I'm pretty much thebrownreport everywhere. So they just go to thebrownreport.com and check out free PDF and all things Jason Brown. I know. Downtown Jason Brown. I like that though. Especially Detroit too. Detroit man. Downtown Jason Brown seems to fit. I love my Detroit people. They're like gritty, but fun and nice. The ones I know, some of my friends are all from Detroit that way. That's funny. I also have a place downtown Detroit, too. Hey, see? Downtown Detroit, Jason Brown. I love it, man. I appreciate you coming on. Ryan, I appreciate you, brother. Hey, man, you know where to find us.
Ryan is right.com. I'll have highlight links, everything from today's show. The Brown report.com. We'll have links there. And of course, where to find us anytime, anywhere at Ryan Alford had that blue check before you buy, baby. We'll see you next time. All right. About now. Here's the truth. Information doesn't change your life. Execution does. So don't just listen to this episode and move on. Take the idea. Make the call. Launch the thing. Fix the problem. Build what you keep talking about building. For more, follow Ryan Alford on Instagram, at Ryan Alford. And watch or listen to every episode at ryanisright.com. This is Right About Now. Now quit waiting. Go win.

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