
Loading summary
Windows 11 Advertiser
Study and play come together on a Windows 11 PC. And for a limited time, college students
David Leiter
get the best of both worlds.
Windows 11 Advertiser
Get the unreal college deal. Everything you need to study and play with select Windows 11 PCs. Eligible students get a year of Microsoft 365 Premium and a year of Xbox game Pass ultimate with a custom color Xbox wireless controller. Learn more@windows.com studentoffer while supplies last ends June 30th terms at aka mscollegepc.
Travis
You're listening to the Travis Makes Money podcast presented by gohighlevel.com for a free 30 day trial of the best all in one digital marketing software tool on the planet, just go to gohighlevel.com travis what is going on, everybody? Welcome back to the Travis Makes Money podcast where it's a mission to help you make more money. On this episode of the show, I have a new friend, David Leiter. He's the author of Stop Making Stupid Investments. He's been a private investor in stocks and multifamily real estate for the past 30 years. He's the founder of the Ultimate Investor, which publishes content on being a great investor, focusing primarily on the principles and strategies of Warren Buffett and Charlie Munger and how average investors can use them to succeed. So, David, what's up, man? Welcome to the show.
David Leiter
Thank you. It's a pleasure to be here.
Travis
So let's go back in time. First off, man, tell me the first time, the first time you ever made a dollar that you were excited about or shocked by.
David Leiter
Well, I think the first, the first, when I bought my first property, this was pretty incredible because at the time I was just working. Like many people, you work a job, you get a check. And then I, I just, I got interested in actually real estate first before stocks. And I, I just thought to myself, this would be amazing if I actually did this right and I bought this property. I could get paid forever, potentially. Like, if I bought a property and, and it worked out. So I just loved that concept. And when I actually closed and did it and then I started, I renovated the property. I got it leased up and then I went to the bank. After six months to the day, I knew exactly, like, I had to wait six months to refinance, take my money out. I had bought something cheap back then. It was foreclosed, actually in Queens, New York. And, and then I bought another one. And that was the first time I really felt like, wow, I'm actually building some wealth, not working hard for money.
Travis
There's like a, there's a There's a path here. There's a, there's an end goal on this journey and I can get started on it now.
David Leiter
Yeah, it was like I, I felt like the, the possibility of.
Travis
Yeah.
David Leiter
A different life than just grinding it out.
Travis
So did you keep buying more houses? What would, what did you do from that?
David Leiter
This was a small apartment building. It was $178,000 in Queens, New York in 1998.
Travis
$178,000?
David Leiter
Yes.
Travis
Holy crap, man. In New York?
David Leiter
Yeah. Queens, New York. Sort of a working class neighborhood in Queens, but not too far from the city. And the economics of it just worked, you know, Like, I just did the work on it. I had looked for six months, mind you. I asked people many, many questions. I didn't really have guidance. Like parents weren't like investors. I just was reading, thinking, and like that I wanted to change. That's where it all starts, right? You sort of have a vision that you want to make more money and then it's like, you know, how do you do it? So there was a path before that where I went broke. So I didn't like that path.
Travis
Wait, wait, wait, what was that path?
David Leiter
No, that path was a few years earlier. Well, so when I got outta college, I got caught. You know, I, I didn't. I realized I didn't really have any skills to make money, really, even though I got into school. So I got.
Travis
That's a good place to be right out of college.
David Leiter
Yeah, right, right. So I got a sales job, which was a brutal sales job in New York City where we'd like sell on the street, we'd stop people. And it was so. But it was so good to do that because I was afraid every day. And then I did it. And I did it. I did it. I got rejected. Rejected. And I learned to sell and I learned to talk to people. And then. So. But then I got caught up in some things, a lot of get rich quick type things because. And I just extended my lifestyle way farther than was appropriate for me. So I got sort of. I've gone broke before that. Then I got smart. So the pain of going broke was actually a great lesson because it was. I like to say I hit ground so hard that I bounced. I was like, I didn't want to. I didn't want to be there anymore. It's like the pain of it. So. So that's what a lot of people do in the beginning when they, they make money. They're actually running away from the pain of something. And then. And that's a great motivator, actually.
Travis
Yeah, it is, it is. When, when you made that investment, what were you doing at the time to make more? You still in sales at the time?
David Leiter
No, no, no. What happened was, right, right after I sort of. I went broke. I got a temp. I said, you know what? I have to get a job. So I went to a temp agency and, you know, I could use, I could type, I could do things. So they put me in a like, office job. And I was very lucky. I, I got put at Credit Suisse, which was a big investment bank, which just went bankrupt, by the way, and they got taken over by ubs.
Travis
Oh, really?
David Leiter
But back then they were merging with First Boston in New York City, and Wall street actually was in Madison Avenue a little farther up. But I, I got a temp job and then once they merged, they really liked me and they had a sales assistant job on the trading desk of called Syndicated Finance. So it was just pure luck. I mean, you know, I worked hard and so they liked me. They gave me a shot and put me on that desk. That's where I really started to change my mindset. Because everybody I was working with made a lot more money than me. It wasn't like double the salary. I was the junior guy on a desk where, you know, this is late 90s and the, just the, the salespeople were making, you know, 5, 6, 7, 800,000 a year plus, you know, and then several people were making multiple million. That's a long time ago, you know. Yeah, it was a lot of money. And so that really opened my eyes to like. Okay. And then they, they actually taught me how to evaluate businesses, how to look at companies to invest in. So it was a great, lucky experience.
Travis
Yeah, no kidding. You feel like you learned more there than you did in college?
David Leiter
A hundred percent. I mean, between the sales job and that, a hundred percent more on how to make money than anything I learned in school.
Travis
I mean, that's sort of like a real life NBA mba. Between those two things, you know, drowning in rejection on the streets of New York City and having to learn that and learning how, like you said, learning how to talk to people, all cultures, all backgrounds, walks of life, languages. Like, all those things that you have to overcome when you're talking to random people and trying to sell them stuff, and then learning about the financials of businesses and what makes a good investment like that. I mean, those two jobs right there, man, that's insanely valuable. What did you do immediately following that? Did you try to like, kind of work the corporate ladder there for some time.
David Leiter
Well, so that was like 1996. By 2000, so I was living through the dot com bubble, which gets sort of circles back to the book because that was the. My first experience of a wild bubble. And like. And so meanwhile, okay, so I've gone broke. I'm at Credit Suisse now. I'm reading. I read a book, the Making of an American Capitalist. It was about Warren Buff, about Warren Buffett. Roger Lowenstein wrote. It was a great book. And it really changed my mindset. So now I'm learning. They're teaching me at Credit Suisse. They say I can go get my mba. I said, I don't know if I want to do that by, by the year 2000. The, the bubble, you know, NASDAQ bubble topped in March 2000 and crashed. But I was so good. I was like keeping discipline. And then in January 2000, I jumped in. I couldn't take it anymore. And I bought some stock healthy on. It was called HLTH. I think it later became WebMD. I wrote it from 63 to 11 and I lost a bunch of money. It was really painful again. But it sat in my mind that people do this over and over again. And I took the. I think the great thing about it was each time I had some. Well, I had that happen. I kept in my mind so I didn't get caught up. Later on, you see this pattern. Even today, you see stocks going crazy. And so, you know, after that, I left. I left in and I went to a trading firm and actually traded stocks for three years. But in the meantime, I had bought a couple more properties. And then by 2003, I just went out on my own. And so I just quit all the jobs.
Travis
Yeah. Was it. Was it your goal to just buy and hold these properties? Do you still have them today? Did you sell them along the way?
David Leiter
Well, in 2003, at that time, I sold the initial properties I bought and I rolled them through a 1031 exchange, which some real estate folks might know, and into another property in. In Brooklyn, a better neighborhood. And yeah, those properties I hold today. So the idea was to hold them forever. The initial thought, if I do. The initial thought was if I do something, if. This is what I love about investing is if you do something right, you've done the work, potentially, it pays you forever. That's the ideal world. Now, it doesn't always work out that way, but sure. But in this case with real estate, it's actually, you know, it's one of the best ways to do it. But I also, with stocks, you know, things change, technologies change, companies come and go, but you still can find those as well that you can hold.
Travis
Yeah. What do you think about now versus this time? Like you mentioned, buying an apartment building in Queens for less than 200 grand. Do you feel. Do you feel like it is as good of an opportunity as it's ever been to jump into real estate? As a first time investor, do you feel that maybe stocks might be a better pick right now? Is there any advice that you could give to somebody who's sort of looking at this right now?
David Leiter
Yeah, well, just to be clear, I'm not a licensed financial advisor. I talk about this stuff just to be clear. But what I would say is that the, the patterns. When I bought real estate in the late 1990s, no one cared about real estate. I bought something, I told you the price, it was cheap, and it was sort of easier in a way because not as many people cared. Then real estate became very popular. And then, you know, 2008 happened, and then actually no one cared again about real estate. You could buy things very cheap. So now where are we? Real estate kind of blew up in 21. For people who are doing apartment buildings, multifamily syndications, this was super popular. And then a lot of those, you know, everybody wants to buy real estate, and so it's not always the best time. I do think now that it's getting better for real estate because it's sort of. A lot of people had pain, so that comes to sort of a theme over. That goes throughout the rest of everyone, every listener's life. You will see these patterns where everybody gets pumped and excited about an asset and the prices go crazy. And that's when you feel, oh, I gotta get in. And there's all this emotional thing about like, you see your neighbor getting rich and you're like, well, my neighbor's an idiot and he's getting rich and I'm not. And you're like, I gotta get in. And like, this is so bad. And that's what the Stop making stupid investments book title is sort of about to happen. It's like, you know, and. And so now stocks have a lot of that going on, you know. AI. So the idea with any investment is to. One of the rules in my book is, you know, be a contrarian.
Travis
Yeah.
David Leiter
You know, try to think what people are not paying attention to, because often that's when prices are better. And it's all about the price you pay in the end. For any asset and about how to value it. And this is where people get lost a lot. But it's worth skill, worth knowing.
Travis
Yeah, that's sort of where I've come along the way. I always like to ask people who are more experts than I am. We buy some real estate here and there, but we're not like, super active. But I grew up in a real estate household. You know, my dad was an agent from the time that I was like three or four. So I always saw them buying properties and doing flips and whatever. And that was always, that's always been. My thing is like, yeah, it's a weird market right now, but a good deal is a good deal. You know what I'm like, it's never, it's never a bad time to buy a good deal, and it's always a bad time to buy a bad deal even. Even if the market's going well. You know what I mean? So it's more just like, well, you're probably just going to have to learn more. You're probably just going to have to invest into becoming a better investor. Or like, if you're, if you're wanting to choose that as a path to freedom.
David Leiter
Yeah.
Travis
Then you just got to know what you're doing so that you don't, you know, lose your ass. And then you mentioned the one thing which obviously comes directly from Warren Buffett as well, which is the, you know, I'm going butcher this statement, but it's something like, be bold when everybody else is timid and timid when everybody else is bold, or something like that. Yes, but that, that's typically what it is. Is it? You know, I knew a lot of people who, smart investors, but they lost a lot of money even in, like, stuff like crypto, because they waited too long to jump into it. And then they saw people getting rich off it, and they're like, okay, let me put some money in there. And then they inevitably put it in when it's at the highest point, and then it starts crashing and they go like, oh, crypto's going to zero. And then they panic, sell everything. And then six months later it recovers. It was before and goes higher. And they were, you know, it's just like, what are we doing here? People like, you're so smart when it comes to these other investments. And then you, you jump into this other asset class, and now you're. You're pretending like you've never made an investment before. I don't understand. Yeah, what, what are your, what are your thoughts? On crypto as a whole. And I know, again, you're not a licensed financial advisor. I am not either. But, you know, these are fun conversations.
David Leiter
Yeah, for sure. No, I mean, I've got a, a chapter in the book called I've got 99 problems but crypto ain't one. And I just. So when you buy crypto, you just have to determine like there's two types of investments. There's productive and unproductive assets. There's two types of assets. A productive assets. If I buy an apartment building, I collect my rents every month. That is my return. I get my return from the rents. I don't have to sell to you or anyone else to get my return. That is a productive asset. If you buy a stock in a business, a company that is growing its earnings, that's. People get confused with stocks because they don't send the shareholders all the earnings. They don't like, send it to you. When you own your own apartment building or whatever, the rents come to you and you do what you want with it. So people get confused with stocks. But a stock is a piece of a business that's a productive asset and you try to determine what are the earnings going to be of that business. That's the Buffett way to do it, in the best way. Now when you talk about crypto, it's non productive, so the asset itself does nothing. So the only return is if you can sell it to someone else who believes they're going to be able to sell it to someone else at a higher price. And then that person has to believe they're going to sell it to someone else at a higher price. Now it's ingenious Bitcoin, for example, because they reduce the supply. So it's designed to create a frenzy. It's an ingenious product and it has worked to some extent. But the problem is if sent, it's all based on sentiment. All of these things are based on sentiment because you can't do anything. The Bitcoin or the crypto doesn't do anything. It doesn't produce anything. So that's unproductive. So it's really important if you're going to do it. I'm not telling people, don't do it, whatever. But I'm just saying if you're going to do it, you should learn. Okay, this is what I'm doing. I'm playing a game of sentiment that everyone else is going to believe that the supply is going to reduce and it's going to be this huge hype. And it can go crazy. And it did go crazy and then it went down. So it's not my game. I don't like it. And frankly, I think you can get plenty wealthy. And I proved it myself through investing in productive assets.
Travis
Yeah, it's a, it's a speculation. It's not an investment, just speculation. What are you seeing? Like if you're going to, if you're going to, you know, again from, from the position of not being a financial advis. If you would be giving financial advice to people in terms of just like, hey look, I've been around a lot of investors. I've seen a lot of people lose money. I've lost a lot of money. I've played here, I've put money in that and I've tried these things and I've tried day trading and all this other stuff. But for most people, this is probably what you're going to want to do. Pick a couple of these types of funds or assets or ETFs or something like, do you have sort of like a playbook for people to follow if they're not going to become, you know, full time investors?
David Leiter
Yeah, I mean most people get into trouble. Which is why I wrote the book. It was purely a mission based thing because I got, I saw people get screwed over and over and over again through my whole career. I saw friends, acquaintances do these deals that seemed like great, but they weren't to me. They seemed silly and they would lose money. And I saw really horrible cases where people lost their whole life savings. Like a lady was 60 years old in a real estate sort of scam. And so the, the biggest thing is that if you're starting out and you don't want to spend time to learn about some of these things I talked about like productive, unproductive assets. How do you value a business? You have to understand how to value assets if you're going to buy them directly. If you're going to buy a stock, don't, don't play the stock market game like a casino. I'm buying the stock because it's going up. You don't even know what the business does. Now that can work for a while by the way. And stocks have gone up and then you think you're a genius. That gone up.
Travis
You're a genius. Yeah, exactly.
David Leiter
Oh, something just happened to my video. Oh, there it goes. And so anyway that's. So if you're going to start out and not want to learn, then you know, get, get yourself somebody who's a good advisor, like A real licensed advisor. Have a plan. How much money do you make a month? You know, what can you do to increase your income? I know that's. I think that's what you do with your folks and try to help them make more money, try to increase your skills. It's really like your communication skills, your marketing skills. Make more money if you're not. I think investing is the great. I always say there's three. Three great skills to learn. Communication, you have to learn how to talk to people. You can't get your ideas across. Marketing, you need to learn how to share it with others that they care. And three, once you have that and you've done it well, you'll probably have money and you need to learn how to invest it. So I think investing is the greatest skill of the three, once you have the other two down, because the returns can compound way more than your efforts while you sleep.
Travis
Your returns can compound. Yeah.
David Leiter
So I don't know. It's a kind of roundabout answer, but I just think if you're not going to learn. In my book, I tell people the framework, how to pick investments, but I say you probably shouldn't because most people do it like a hobby. And so they win here, they lose here, they win here, they lose. And that doesn't really build wealth.
Travis
Yeah, I was gonna say. Which is fine if you also embrace the idea that it's a hobby, just like you would sports betting or playing poker or something. It's like it. It don't. You can't play. I mean, you can, I guess, but you should not play with your entire nest egg with stuff like that. It's more like, hey, I put. I put, you know, this amount in, like, T bills. And then I got some money over in, like, the S P and I have this ETF over here. And then like 10, 20. I go play in some crypto things and I do a little bit of day trading to have some fun because I like it and it's entertaining to me and I like learning about that stuff. But if you're putting all your eggs in that basket, I think you're gonna be sorely disappointed given, you know, at least two years, three years of doing it.
David Leiter
Yeah. Yeah, I think so. In the end, I've seen a lot of people, they win, they lose, they win, they lose. The biggest problem is if you're a young person, whatever, and for anybody is time. If you don't, you. You. You're losing time of compounding.
Travis
Yeah.
David Leiter
So if you can even, you know, it's so boring to say. But even like an index fund, which there's a lot of arguments why people, if you buy an index fund at this level of that your 10 year returns will be quite low. Like historically speaking. But if you dollar cost average into something like that, at least at one part of. So you're participating in the growth, all you have to say is do I believe in America and these businesses are going to grow. If you can say that and you believe it, you want to participate in it. And then if you want to learn skills about real estate, you have to learn more. If you're going to pick your own stocks, you have to learn more. But like you said, if you wanted to take a percentage and do it, it's not my game. I understand why people do it and eventually I think if you get whipsawed around enough, you start to think okay, maybe I need to get serious. And you know, but that's just everyone's own evolution on what they want to do and what they're interested in.
Travis
What about buying your primary residence?
David Leiter
Yeah.
Travis
Do you look at that as an investment? Do you look at that as a lifestyle thing? How do you, how do you look at that?
David Leiter
Yeah. So this is a really interesting one. I know people talk a lot about it. A house is not typically a great investment from a dollar and cents perspective because it historically keeps place with inflation what it is, how it can be valuable. A, it gives you, it locks in your biggest expense, which is housing. So it locks it in to if you get a fixed mortgage. And so you lock that in so you're not subject to the rent. It's also, but there's also to me there's on sort of off the spreadsheet values of a house. It's like if you love your house, you feel good at it with your family and you might be a more productive person. Yeah.
Travis
Sense of ownership, like pride in your community, things like that.
David Leiter
Yeah, yeah. You might just be more productive. You come over, you know, you just, it elevates your perception of yourself, who you are. You look out, you like, you like where driving into your driveway, you see that house? There's un. You know, people don't talk about that. Everybody's about dollar sense. This what annoys me about a lot of sort of investment gurus. It's always like cut and dry. It's like a house is stupid. You're stupid if you don't do like they like insult you. And like, you know what? It's not that cut and dry. Right. What is there, there are some things that do work. And then the other thing about a lot of investment groups, they do. Some of them have, like, conflicts. They're selling real estate, so they talk about.
Travis
Exactly. Yeah. That's always the big thing. That's. That's the red flag. It's like, doesn't. Does not necessarily mean that the advice is wrong, but it does mean that you should get a second opinion if the person's advice that's giving you advice is like directly benefiting from the advice that they're getting giving you.
David Leiter
Right. Yeah.
Travis
Maybe take a second peek. Ask somebody else as well. Yeah.
David Leiter
Yes.
Travis
Well, listen, man, I appreciate you taking the time to come on the show. David, the book. Stop making stupid investments. If you are somebody looking to become a better investor, you owe it to yourself. Go pick up a copy of David's book. Where else can people go to get more from you, David?
David Leiter
Well, theultimate investor dot com. The ultimate investor with the. I have things there. I have packages around the book, actually, where you get like a course online. Great. And I just teach all this stuff. And a lot of people like the way I teach this. They. It's not super complex. You don't need to be a financial analyst or something. And so that would be one way. I also have a YouTube channel, the Ultimate Investor. I just kind of started doing social media, so I'm on there. And Instagram as well.
Travis
TheUltimate Investor. Com. Go check out some of the stuff that David's been putting out. Pick up a copy of his book. David, I appreciate you taking the time. I know you're a busy guy. I don't take that for granted. Everybody else tuning in, remember, money only solves your money problems. But it's usually easier to solve the rest of your problems when you got money in the bank. So let's solve that one first here on the Travis Makes Money podcast. Thanks for tuning in. Catch you guys next time. Peace.
Air Date: June 15, 2026
Host: Travis Chappell
Guest: David Leiter, author of "Stop Making Stupid Investments" and founder of The Ultimate Investor
In this episode, Travis Chappell welcomes investor and author David Leiter to dissect the principles of smart investing, inspired by Warren Buffett and Charlie Munger. The conversation centers on avoiding common financial pitfalls, learning from past investment mistakes, harnessing productive assets, and developing the mindset necessary to build lasting wealth. David draws on personal experience in real estate and investing, sharing actionable—and often contrarian—advice tailored for everyday listeners.
This episode blends personal narrative with practical financial wisdom, making it a useful resource for both novice and seasoned investors.