201: From Rap Star to Wall Street: How to Invest Like a Pro
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Welcome back to another episode of The Richer Geek Podcast! Today, we have a very exciting guest, Kevin Davis. Kevin's journey began as a recording artist signed with Warner Brothers Records, but his passion for finance led him to Wall Street, where he gained experience as a stockbroker. Seeing a need for accessible investment education, he created Investment Dojo, a gamified stock simulator app that helps people of all ages build confidence in investing. In this episode, Kevin shares his inspiring story, discusses the importance of understanding your investments, and explains how Investment Dojo is empowering families to learn about the stock market together.
In this episode, we're discussing:
Challenging Start: Kevin was kicked out of his house at 17, living place-to-place while juggling part-time work at UPS and college.
Wall Street Entry: Inspired by the movie Trading Places, Kevin began his Wall Street career at Stratton Oakmont after a serendipitous conversation with a neighbor.
Research Skills: Kevin mastered stock research by focusing on free cash flow and business models—skills that became the cornerstone of his success.
Founding Investment Dojo: During his retirement, Kevin recognized the lack of accessible financial education. He founded Investment Dojo to teach others how to research and build wealth.
Education-First Approach: Kevin emphasizes teaching people how to analyze stocks and make informed decisions rather than relying on stock picks.
Resources from Kevin
LinkedIn | Investment Dojo | Who's Your Daddy by Kevin Davis
Resources from Mike and Nichole
+ Read the transcript
Kevin Davis
Everybody, welcome back to The Richer Geek Podcast. Today we have a very exciting guest, Kevin Davis. We're going to have him go through his background a little bit, but I bet we haven't had a Warner's Brothers rap, almost superstar East Coast guy turned stock broker, and of course, he worked for, The Wolf of Wall Street's famous Stratton Oakmont. Now he has his own app called Investment Dojo. The guy's done a little bit of everything. He's experienced a lot, and he's learned a lot. Welcome, Kevin Davis, how are you doing?
Kevin Davis
I'm doing great. Thank you, Mike, appreciate you having me.
Mike Stohler
Absolutely. So let's talk a little bit. I always start the podcast, your background and how you got to where you are when you finally realize that you know what I need to do at the Investment Dojo. But go through your background a little bit. It's very colorful. It's a very exciting background.
Kevin Davis
Yes, it says the least. So where does it start? It starts out when I get kicked out of my house at 17 years old, right to pass it, Mom goes, "You know what? I got kicked out of my house when I was 17. You're no different. Get out." And so therefore I'm scurrying. I'm living from place to place. I bought a new car. That's probably what spurred it on, and she didn't have a new car. So that was hilarious. At that point, I didn't find it so funny then. Anyway, so I'm staying with friends and bouncing around. And then my buddy says to me, "You know what? You're really good at this rap thing. You should make a record." I'm working part time at UPS and going to college." And I'm like, "Rap. What do you mean?" I'm in the park every month, every week, doing my little battle rhymes, so I was living in Queens at the time, or from Brooklyn, but LL Cool J lived in Hollis. I was in Springfield Gardens, and so Hollis was maybe 20 minutes by car away. So Run-D.M.C was in Hollis. And you had all these rappers that germinated, it seems, from Queens. But anyway, so I started to rap in a park about maybe three years later. I wanted to get a record deal with Warner Brothers. I had a hit record, traveled around the world, did some things and gained some experience outside of the neighborhood. I remember my first time getting on a plane. I was terrified, and I flew five times in one weekend, which was my first introduction. So I'm surprised I still get on planes to this day anyway.
Kevin Davis
The music career was great, but then when it was over, I realized that I made a ton of money in the music business. I was making like, $90,000 a month. As a 21 year old, it didn't really, it didn't click. Because back then, the 80s, early 90s, because '89 the record came out. So it's really early '80/early '90. So that was a decent amount of money at that time. Then I saw this movie Trading Places, and I said, "oh, $1 I want to do that." And I didn't know it was commodities. I thought it was, I had no clue. So, meanwhile, my grandmother lived in Kew Gardens, Queens, and I'm sitting in front of her house, in front of my car, and my next door neighbor, her neighbor, sitting on the step, and she saw me looking at one of them. She said, "What are you looking at us?" "I'm looking at these stock work ads." She says, "You can make X amount of dollars. And I was like, "No." "Well, you can come work for me. Well, at my job. I was like, "Okay." And she took me to Stratton Oakmont.
Mike Stohler
Wow.
Kevin Davis
Yeah. And the interview was even more nuts, Bobby Koch. Bobby Koch pulls me to the side. He interviews me in the cafeteria, and he says, "Well, what makes you think you could be a stockbroker?" The funny thing about me is, I had a little street decorum, so he did not scare me. So I stood up and said, "What makes you a stockbroker?" And he laughed. And I was just tough. I was rough around the edges. I don't think I was speaking the King's English, but he saw something, and he hired me on the spot. And I think I stood. I got there at five in the morning, and I stood all day until about nine o'clock at night and sometimes until 12, and they loved me for it, but I'd known it better. Yeah, that's the first part. That's how I got to Wall Street from the music.
Speaker 1
It's unbelievable. I mean, what is the story? It's like, the right place at the right time. It's absolutely unbelievable. So you're doing this, and then you go to another small research shop, and then you're building up your experiences. And then 25 years later, what clicked has just said, "You know what? I need to do, Investment Dojo."
Kevin Davis
Well, I got tired of Wall Street. I was there when the dot-com blew up, and then I decided that I wanted to move to Florida in O Five. And my firm, the research firm, where I really learned how to really do the research on stocks based on free cash flow, business models, all this stuff, they allowed me to work for a few months in Florida without supervision. I didn't want to take my 24 and become a principal. I had an interest in mortgages, so I decided to open a mortgage company. I went to work for a small firm for six months, and then, because of the stock broker side of me, we cold called every day like animals. So it's so easy to get business. I would get like 20 mortgages in a day. It was just nuts, because refinance was big, and people's mortgages were going up from like 6% to 10%. So it was easy to get them to do refinances. And I knew where to find them. I knew how to get them on the phone. I knew how to write a script. So that was cool. Did that for, I guess want to say three years. Made a ton of money doing that. Then that went out of business. So then I went to an insurance company who said, you can have your own franchise as a unionized shop if I write X amount of dollars. So I wrote an extra amount of dollars, and I got my own franchise, and I moved from Florida to DC. I didn't want to move, but I did. And I was a state general agent for Maryland, DC, West Virginia, North Northern Virginia. And, you know, I did that. I knocked the ball off the cover. And I retired in 2016, right?
Kevin Davis
Came back to Florida 2017 and then I'd realized something. I remember calling my buddy. I think it was 2014, I think Apple had split seven for one. And I said to him, "Listen, you should get some Apple." He was like, "Ah, man." And this time he was managing A$AP Rocky
which is Rihanna's, you know. So I was like, "Yeah, that's what I would do." And it was like, $94 a share. Oh, don't worry. I was pitchy. I was recommending Apple at 18 and 95. I let that out. But anyway, so I couldn't do it, because my expenses were 22k a month, and I was running the business, so I couldn't have any free cash flow going into the business, you know? So when I retired in 2016 and came to Florida again, I said, "You know what my wealth is inside of me?" I remember walking through the house like, my wealth is inside of me, and it just turned off, and it was like, "Okay, start researching again."
Kevin Davis
So I started researching stocks, and all of a sudden I was picking, I must have picked up 11 stocks. And out of 11, like eight or nine of them tripled. It was, but it was because we were in the biggest bull market, 2008 going forward, right? So this is 2017, we really didn't get any hiccups until like into 2018-2019, right? So I've told my friends as they were, they were pushing me, pushing me to teach and coach. And I was like, "No and no and no" .So when the pandemic hit, everybody said, "Okay, what are you going to do?" I said, because my son was two years old, and I was like, "I'm retired, so I was pretty okay financially. But I said, "Okay, I'll start the group."
Kevin Davis
So I started the group, Investment Dojo. I had already had the incorporation in 2019 and the group went from 29 members to like, 6,000 overnight. And I got this reputation because I always tell people, I rather teach you how to research and tell you about a stock pick. I'd rather you not take the word or even my word. I'd rather you know how to quantify and qualify. If you could do that, then you can have some way to build wealth for your family. If not, it doesn't make sense to take. It's like the movie, Dumb and Dumber. If you listen to them. You're the dumbest, right? So it was like, "Don't take your word to somebody." And so the light bulb went off for me in 2016-17, and it's been charging and charging, and it led up to this moment.
Mike Stohler
So let's talk about Investment Dojo. We've kind of talked about it. What is it? And explain to me the concept behind the education part, and what are the different levels of Investment Dojo. What's what's in it?
Kevin Davis
So if from face value, it's an app, right? And it's a simulator, stock simulator, right? And it's moderated, moderated by me and my team. So what does that mean? So let's just talk about what's the app first, and some of the features, and then you get into the moderation. Okay? So you can have group chats, you can play in a public room. You can play in a private room. You can play against 100 people or 1,000 people, friends or family, whatever the case may be. We moderate the game so you can reach out to us. We teach you how to play the games. When we moderate, we do master classes. So we'll teach you about the bond market and your 401(k)s. We'll teach you about the daily macro and micro environment in the stock market as well, if you're in a moderated game. And so I use it as a vehicle to teach, but then I became a financial coach. So what happens is, it's become my filter, too. So unlike most people, have a product and want to sell something, I kind of try hard not to. I only want to deal with the people that I really, really want to help.
Kevin Davis
It's different. I don't know, it's just me, right? But it becomes a filter of some sorts, but it allows me to really impact a lot of people, and I started it in 2020 because we were playing on an app called Investopedia. And Investopedia has a simulator, and their simulator was going good for a second. I had 21 games with them, but then the game went down. So my buddy was like, "Kevin, why don't you finance your own app?" I was like, "Oh, that makes sense, I guess." And so my wife was a marketing guru. She goes, "Well, I'll find you the company." So she found me the company, and they told me six months, but it took three. And when it comes down to the app itself, it's been a vehicle for people to learn the market. But what I found is that people have so much fun competing and learning at the same time they forget their inhibitions and apprehension to the stock market, and at the end they build a habit. So I put on two week competitions and at the end of that competition, if they qualify, they can get into coaching, if they want to get into coaching, if not, they can continue to do what they're doing and keep learning and a process. And I do meetings every Wednesday on the page for them, as they call it. It's immersive and it's wildly educational.
Speaker 1
Absolutely, we were talking about this a little bit earlier. I mentioned this to a financial advisor who's doing well. And I was like, "Oh, you should check this out." And he was talking about how it was finally a concept that kind of went off in his head, that he could teach his middle school-aged children how to live. You know, this is the real world. This is what happens. He was like, you keep hearing me yell and scream about the stock market and all these different things and, well, this is exactly what it is, and why I'm we're doing this. So, talk about the importance of, not only for just people getting educated about this, but it's and it's also something that parents can do with their children. It's a bonding time. It's a learning experience. Talked a little bit about how it can affect the entire family dynamic.
Kevin Davis
Yeah, everything's about family. Everything I do is purpose drilled. Do you know about my son or my and my daughter? So if you're playing with your children, the one thing about the market is no day is the same, so you never get bored, and it's so competitive, and once you know how to play like we have these games that are 15 minute lags, we play with a 15 minute window. You can play in real time, but you gotta be decent to do that. But playing with a 15 minute window allows you to see the market in advance. So if Apple's trading at $200 on the app and it's trading at $218 in the market, you could buy it in the mark on the app at $200 and sell it 10 minutes later at $218 so now you don't have to be good at the market. So what's happening is you're just finding and exploiting so people go. Well, how do you learn that easy stocks go up for a reason, and they go down for a reason. And your job is to find out why. In that cost of finding out why, we tell you where to go, investors, relations pages. Do this. Do that. Okay, this is how you look at where the next earnings are coming out. Yahoo Finance, 16 analysts are following the revenue expectation, earnings expectations. They're getting this information while they're playing right.
Mike Stohler
Wow.
Kevin Davis
So now, if it's during earnings season, they know how to go to Yahoo Finance, go to markets and see the calendar and see what's happening. And so it's just about market awareness, knowing what it is. And then, Peter Lynch, he's one of my heroes in the market, right? So by what you know is his main mantra, make it simple, so a seven year old can understand it. So I always say baby food, right? And so my thing is, monetize what you patronize. So if your kid is watching spending all his time on his phone, do you own Apple? If you're and not say to go out and buy Apple, meaning, do some research. Make it make sense. But when you're looking at YouTube all day, do you own Google? If he's got a computer all day in front of me, he's always writing whatever, does he do? You own Microsoft, right? If he's on ChatGPT, does he own Microsoft, right? Do all these little different things, and you can center allowance around these things too, which is so cool, because what happens is you can create a point system that says, "Okay, your chores and your duties to be fulfilled are going to give you 20 points." And every point equates to $5 or $1 or $2 whatever the case you want to do, right? And you'll never get all of the money if you hit all of the points, meaning, let's say it's $100 a point, right? One point up to $100-$50 is going to go to you, right? But the other $50 is going to go to the things called investment, right? So this way you're working, you're learning, and we're going to sit down and we're going to discuss these things, because we have to sit down and decide what our free cash flow is going to go to. So our free cash flow is the extra $50 right? What's for me, is the $50 now, when you get into the real world, it's going to be different. You're going to have to take a third of your money, right? Each dollar, a third, and you can put that on the side, another third, pay your bills, another third. Well, you can have the life that you want just live your life with it, right? Or you could take two thirds and plan to work hard upfront so you can have the life you want later. It depends on how you want to do it. You make the choice. But it's so many lessons there. But this all spawns from Investment Dojo, because I push this narrative right. Because, like I always tell people, I come from a standpoint of want, not need, so I'm always going to be pushing education. Because I did not know what I meant. I remember I thought Johnson & Johnson was baby powder. I didn't know so it's funny how we think about it, but it took me so long to get around to this is important to actually using the information. I was an order taker in the first 10 years of my being a stockbroker. I wasn't researching. I wasn't bringing them my ideas. They were telling me this made sense. Gave me a report, and this is what I bought for my clients. Once I realized that I knew, "Wow, okay, growing at 25% CAGR, this earnings, "Oh, wow. Free cash flow." And I can factor it out based on the yield. I was like, wait a minute, wow. I actually know how to do this. And when I discovered that made more sense, and it made a lot of money, it's like the kids are in very nice positions financially, because I learned, soon as they got a social security card, we going to open up a stock account, a custodial account, and it's going to be every single month, it's a no look pass.
Mike Stohler
Wow.
Kevin Davis
And that's it, yeah.
Speaker 1
And it's just teaching them, instead of like, "I want, I want, give me, give me." Like the kids now today, you know, we won't get started on that, but, you know, it's entitlement, right? So if you teach them at a young age that this is how life works, and this is how you get money. This is how you keep money. This is how you respond to situations. I mean, this is just absolutely fantastic, I don't know the original reason why you did this Investment Dojo, but just the implications that it can have for generations, throughout the United States, perhaps to the world just teaching, "Hey, this is the US stock market. This is how you do things." Where do you see this in five years when you think about Investment Dojo?
Kevin Davis
So upon the platform. As I said to one of my buddies, very smart. I mean, super smart guy. There's no university. People don't learn this in school. So I really want to use the app. It's like theAngie's List of investing when you go find out about the stock market, and you get the resources as well. So later on, I have this Rolodex of financial advisors all vetted, right? Real estate guys all vetted. And I mean, when I say vetted, I mean vetted.
Mike Stohler
Yes.
Kevin Davis
If it comes from the source, it's gotta be, right. Like your state attorneys and building out an educational platform that allows people to say, "Okay, well, I don't want to be in probate, so I need to have my trust."
Mike Stohler
Yes.
Kevin Davis
Right? My child is autistic, so one of them is and so I need to make sure I have a special needs trust. And so I gotta make sure that knowing it's one thing not to know, right? But then when you know and don't do well, that's negligence, right? And if you have children, you know how our heart is on the other end of our we wear it on our sleeve for our children. So if you have children, you breathe to make sure they're okay. So you have to get the information and do so. So I just try to make it as available and as easy to understand. And you know, it is not because information is already threatening enough, it's the delivery and method that makes sense and just walk people through. I have people that are doing extremely well. I'm a financial coach along with it, but I always tell people I can't tell you what to buy. I can only tell you what I'm buying for my son. But here's the reality, I'm going to teach you how to research it. If you decide to buy it, you better know what you're buying, because I know what I own, right? And so the accountability. Like I tell people, if it happens wrong, it's my fault. If it happens right, it's my fault. It's called accountability. It's my fault. So I'm either going to fail on purpose or I'm going to be successful on purpose. So that's what. And then they get that whole thing too, because I think we're in this in a time where we're pointing fingers, and it's me too, and it's the emotional Well, here's the reality. I don't watch the news for that reason. But the main thing is that I'm so busy doing research, I'm always looking for something that's going to be like I always tell people they are chasing a tail. I'm moving forward. I'm just taking steps while people keep running in circles. That's all.
Kevin Davis
And I'm not better than I'm just trying to better myself. So if I can help people. I recommended the book, 7 Habits. I think it was. It talks about masterminding by Carnegie, but it's just one of those things where just having your circle and giving them a place to have a role model, so to speak, of what they should know, what they should do, and where they should start. And the last thing I'll say is this, my friends can't do this. This is one of my good friends. He inspired my buddy, John Sparby. He inspired me to do this. He's also a state general agent. And he goes, "Kev, I got 300k. I want to learn what you're learning." I said, "Well, here's what you're going to do, buddy. See this thing called Vanguard. You're going to go find yourself a financial advisor if you want to know what I'm doing, take 2% of that, and then I'll help you learn what I'm doing. But I can't tell you what to do. You gotta be responsible for that." He's like, "Okay, I outperform his Vanguard guy every time."
Speaker 1
We've been talking about the children, a lot about legacies and things like that. Do you have a book? It's called, "Who's Your Daddy?"
Kevin Davis
Yeah.
Mike Stohler
What prompted that? And tell us a little bit about that book.
Kevin Davis
So that was an emotional journey. My first son at 51 years of age, I decided to have my first child. He's six now, and I was saying to myself, "God forbid something should happen to me before this guy turns into a young man, 18 years old, right?" So I said, "Let me write down my life story, all my finances, fixes, everything that I've learned." I've owned a mortgage company, I've owned an insurance company, I've been a stockbroker. And so I said, "Let me give him all these financial doorways." And I wrote all of those. I wrote the personal part of me so he understood who his father was and what he went through, the struggle on the relationship with my mother and my stepdad, who became like my real dad, because I never knew my dad and so I didn't like him in the beginning, which is crazy. It was a story of how, and I bring up that point for a reason, because it's about maturity. Well, my stepdad, but my dad was 30 years old when he met my mom. And at 30 years old, when you think of a 30 year old these days, oh my god. They're not mature. They're crazy, right? You know? But at 50 something years old, he was like this amazing difference. I couldn't stand him. From 30 on to then, and then all of a sudden, I found myself where I needed to reconnect with a male figure, and it was him. And he helped me get my cars. He helped me get my life right. He did, it's like the maturity in it. And he reached out for his son, and so I wanted him to see that relationship. So I wrote that I wanted to see me fail forward. He saw me conquer a lot of different things, but I wanted to see me fail forward. So he knew that was a real thing, right? The relationship with my mom was turbulent, but we did, we did. We took care of her so we made sure he saw that as well. So the book became a financial journey and a biography at the same time. And it writes a patch story. So it's a pretty cool book. Everybody raves about it.
Kevin Davis
Wow. I mean, you get goosebumps just even thinking about it. It just had to be such, just physical, mental, emotional, spiritual journey, all those wrapped in together, put down in words, and that's fantastic.
Mike Stohler
Before I let you go. Sometimes I miss things. Have I missed that you would love to share with our listeners? About Dojo, about the book about life lessons learned, anything that I haven't covered, that you'd like to share.
Kevin Davis
I think we hit it all. I guess the only message I would leave is that you gotta play with the scoreboard and the time clock. And what I mean is, I look at it like, so I'm 57 if you look at in terms of days, if you live to 80, you get 29,200 right? So if I did my math, if I take the 23 years from now until 80 I have 8,395 days left, I gotta live them to the fullest. And then the part about this is, don't get wrapped up chasing money, because you have a health scoreboard too, and if you don't check into that, I don't care how much money you have. Know you can't buy yourself out of death.
Mike Stohler
That's right.
Kevin Davis
So you gotta make sure you take care of yourself too. So, pay attention. It's more to life than money and chasing things. So if you're going to do it, build it on purpose. That's why I say, I live life on purpose, on purpose. If that makes sense.
Speaker 1
It does. You know, one of my models that's over my desk is "Build a life that you don't need to vacation from." I see that every day, and it's like, "Look, it's not about the money." The money will come if you do things properly.
Kevin Davis
Correct,.
Mike Stohler
Correct? But what's more important is spending time with family, spending time whenever I can work anywhere in the world that I want to, and it's just the stress release and doing things without just constantly being scared about what's going on in life, paranoid. He's saying, offended, all those things. But people are like, "Wow, I want to do this. I want to do this." How can people find you? What is the website?
Kevin Davis
So the website is investmentdojo.com but you can find me on Facebook. Investment Dojo Facebook, TikTok, Investment Dojo on YouTube. I'm pretty easy. If you want to get involved with one of the contests, you can just join the Facebook group. I post them every single month, and you'll be able to take advantage of a moderated game.
Mike Stohler
Perfect.
Mike Stohler
Kevin, it's been such a pleasure getting to know you and have you on this episode. Everybody, this concludes another episode of The Richer Geek Podcast. Check it out, Investment Dojo. I think you learn so much. I'm going to check it out myself. Kevin, thanks so much for joining us today.
Kevin Davis
You're very welcome. Thank you, Mike, appreciate you.
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ABOUT KEVIN DAVIS
KEVIN DAVIS, a Brooklyn native, began his journey as a rapper in the late 80s, landing a deal with Warner Bros. Records and scoring a hit with "Stomp" at age 23. After touring globally for five years, he pivoted to finance, inspired by Trading Places. Starting as a stockbroker, he worked at Stratton Oakmont and other firms before gaining decades of industry experience. This journey inspired Investment Dojo, the world’s first social trading competition app, launched in April 2024. The app gamifies the stock market, making it fun, exciting, and highly educational.