The Motley Fool Interviews Barry Ritholtz: How Not to Invest

In this podcast, Motley Fool Chief Investment Officer Andy Cross and analyst Jason Moser talk with Barry Ritholtz, author of How Not to Invest: The ideas, numbers, and behaviors that destroy wealth -- and how to avoid them.

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A full transcript is below.

This podcast was recorded on Oct. 05, 2025.

Barry Ritholtz: The other mistake that leads to more mistakes is simply not having a plan. Like, more money for the sake of more money doesn't really do anything. It's got to be, what do you want this money for? Once you figure out your goal, hey, then you could figure out the appropriate risk tolerance to get to that goal over time.

Mac Greer: That was Barry Ritholtz, author of How Not to Invest. I'm Motley Fool Producer Mac Greer. Now, Motley Fool Chief Investment Officer Andy Cross and Analyst Jason Moser recently had a chance to talk with Ritholtz about how to invest and well, how not to.

Andy Cross: Welcome to another Motley Fool conversation. I'm Andy Cross, joined here by fellow investor at The Motley Fool, Jason Moser. We're really thrilled to be joined by Barry Ritholtz. Barry Ritholtz is the co-founder, chairman, CIO of Ritholtz Wealth Management and Financial Planning and Asset Management firm with cash now $6.4 billion under management. Barry was an early financial blogger, pioneer, along with the fool around the same time, launching his Big Picture blog in 1998 over at GeoCities. It's still ongoing. I'm glad to say, I love reading that, Barry. He's also the creator and host of Weekly Masters and Business Podcast Series, which you can find on Bloomberg. His book, How Not to Invest, I hold right here in my hand, published in March of this year. Welcome Barry Ritholtz to the Motley Fool. Thanks for being here.

Barry Ritholtz: Well, thanks so much for having me.

Andy Cross: Barry, the book is just chock-full of great stories. Investment wisdom is as much as a behavior of finance book, I think, as almost anything, and we'll get to it. I do want to say, really, you've distilled this wisdom in this book from over those thousands and thousands of words you've written, articles, blogs you've written, podcast you've given. You really chose mistakes to zone in on to start this book. Why that approach around mistakes as opposed to writing another how to book on investing?

Barry Ritholtz: Well, the ugly truth is there have been thousands, maybe tens of thousands of how to books written over the past I don't know, 50, 100 years. Despite all of this information telling you what to do, most people are still pretty mediocre investors, and it's not because of the things they're doing right or failing to do the things that are right. You could do everything right. But if you make just a handful of small mistakes, they have devastating consequences. Bailout Nation came out in 2009, and I've had publishers harangue me for a while. Hey, let's do another book. Hey, you should do a how to book. My answer was always, what good is that going to do? It was really during the pandemic, just going through notes, we all had a little extra time on our hands, that it dawned on me, the last thing in the world that anybody needs is another how to invest book. But hey, how about how not to invest? How about if you could just avoid these mistakes, how much better off you'll be? Once I came up with the framework of bad ideas, bad numbers, bad behavior, I don't want to say it wrote itself, but it laid itself out very nicely.

Andy Cross: It's funny you quote Charlie Monger at the very beginning. Don't try to be smarter than anyone else. Just be less stupid. I feel like I'm eating my spinach before I get to my dessert. You're giving me these kinds of, my gosh, these great lessons I've observed, you've observed over your years and years of investing wisdom to start with those mistakes, and you make the parallel with tennis. It's about making those unforced errors that we have to be very cautious about in investing.

Barry Ritholtz: That's right. Tennis is a good metaphor. Driving a car on a race track is a good metaphor. Investing, basically, the problems happen when we try and operate out of our skill set and expertise. The example the other Charlie gave, Charlie Ellis, in Winning the Loser's Game was, it's really two games in one. The games the professional play and the game that the amateurs play. We're recording this. Djokovic is on pace to possibly winning yet another Grand Slam event, and folks like him win by scoring points. They have incredibly powerful serves. They hit with great precision. They use all sorts of fancy spins. They kiss the line. That's not how I play. When I lose, it's because I double fault on a serve. I hit it long, I hit it wide, I hit it into the net, or I hit it right back to the sweet spot of my opponent. All those mistakes lead to unforced errors and points for the other side. If you want to win when you're playing the amateur game, not the professional game, just make less mistakes. Just don't try and overpower the ball. Don't try and be too fancy. Keep it away from your opponent, but don't think you're going to just kiss the line. You don't have those skills. We see when people operate outside of their own ability, that's where they make mistakes that cost them money. In the markets, that means, hey, I'm going to create an all personally picked stock portfolio. I'm going to time the market. I'm going to follow this news flow and bet on my understanding of what's going on and what it means for the markets. When the reality is that news is already in the price. There's no advantage to taking public information and thinking that you're going to be able to trade against the professionals. Trade against the guys with 150 mile an hour serves.

Jason Moser: Barry, forgive me, I probably would have gone with golf as the metaphor, but that's just me. But the lesson rings true. You just avoid the silly mistakes, the unforced errors. I really enjoyed the book. It seemed like a predominant theme in the book leaned a lot more toward passive investing versus active. To be sure, you presented data to back that up. But I guess I wanted to ask, what's your general view on active investing, and what would you say are the keys for active investors to outperform?

Barry Ritholtz: Sure. The first step for assembling a broad portfolio is, hey, you can't get Alpha if you aren't at least starting with Beta. You'd be surprised how many people just neglect that. I love the idea of making the core of a portfolio. I describe it as your Christmas tree should be your passive portfolio, and your active selections are the garland, the lights, the ornaments, all around that. But if you at least start with Beta, hey, you're at least going to get what the market takes. We've learned that active does much better on the bond side than passive does. You have to be really selective where you're applying passive investing. You have to have a degree of awareness. Stock picking is so hard. In fact, the data shows professional managers are really good stock pickers. They're really bad stock sellers or stock holders. Look at the biggest companies out there, the leaders in the market, Microsoft, NVIDIA, Apple, Amazon, go down the whole list. They've all had incredible drawdowns on their way to becoming trillion-dollar companies. When AI came out, we heard that this is the end for Google, and a lot of people lightened up on Google. It took a big hit, and now Google is double what it was when, I think, Anthropic first launched in 2022. Just because something rolls over and draws down doesn't mean it's the next Enron WorldCom, Lehman, Bear Stearns, whatever. Recognizing that, it's really a challenge. Look at the drawdowns you saw following the dotcom implosion in Microsoft, Apple. Amazon was a $5 stock. In the early 2000s. It's unthinkable. Apple, when the iPod rolled out was a $15 stock with 13 cash, and nobody wanted to touch it. You really have to be very aware of what your ability is. Hey, if you want to pick stocks, well, knock yourself out, just do so with a smaller portion of your portfolio and make sure you actually have some skill at it, not just finding the winning stocks, but understanding how to hold them and when to finally cut them loos.

Getting back to mistakes because that is really what the book is all about, how not to invest. You had a nice section of the book on investing mistakes, and given this is a conversation about how not to invest, what would you say are a few of the more common mistakes you see investors make today?

Barry Ritholtz: It depends on where people are in their investment cycle, how old or young they are. I'm going to give you a lot of stuff that comes straight from the data. What we've seen in the 2010s, it started to change in the 2020s, young people were taking too little risk. They were underinvested. Hey, if you're 25, 30, even 40 years old and you have a time horizon that's measured in decades, not years, if you're 25, you have a 40, 50 year time horizon. Why would you be sitting on a pile of cash and. Or bonds? You should be pretty much, if not all equity because some people that's a little too aggressive, mostly equity for the long haul. A combination of a broad index and pick your favorite stocks for the next 20, 30, 40 years works better. That's one issue we see. People wildly underinvested when they should be embracing risk. The other end of the scale, we see people in their 50s and 60s heavily concentrated portfolio, lots of wealth in a single stock. It could have been an employer, it could have been inherited stock. Hey, why are you taking all this risk? You're already sitting on a giant pile of money enough to last you the rest of your life, throttle back.

Those are two of the bigger allocation mistakes we see. The other mistake that leads to more mistakes is simply not having a plan. More money for the sake of more money doesn't really do anything. It's got to be, what do you want this money for? Once you figure out your goal, hey, then you can figure out the appropriate risk tolerance to get to that goal over time. When we see hedge funds that just lever up 10, 20, 50X leverage in pursuit of more, they invariably blow up. If your goal is more, then how much risk is too much risk? That doesn't guide you. But on the other hand, if you say, hey, I'm saving for retirement, generational wealth transfer philanthropy, you could create a plan and then marry that plan to an allocation that accepts as much risk as you're comfortable in order to achieve your goals. Now, the challenges risk and reward are two sides of the same coin. If you want high reward, well, then you're going to have to take more risk, and risk means you may not get what you want. I love the definition of risk is risk means more things can happen than will happen, and some of those things that can happen aren't good. How much more risk do you want to assume? We feel you want as much risk as necessary to get to where you have to go, but not a whole lot more than that.

Andy Cross: Barry, you mentioned the fascinating fact that it's not so much the buying, it's the selling where investors fall down. Just a quick study that you've referenced in your book looked at what they call the counterfactual portfolio of random sells of more than 780 institutional portfolios, and the random sells outperform the portfolio of active sells by 50-100 basis points over the following year. My question to you is, why do you think that it's the selling part that investors tend to get so wrong? Because you juxtapose that against the study from Henrik BESS and Binder that shows that 1% or so of the stocks in any given long range period drive almost all of the returns in the stock market.

Barry Ritholtz: The BESS and Binder study found depends on the country, 1.5, 2, 2.5, depending on what part of the world you're looking at. But the good buyers, bad sellers, I think my explanation makes a lot of sense. The buying process is quantitative and rational. You look at the world, hey, what stocks are reasonably priced? What momentum is going up? Who has a moat, who has a good product? There are a lot of different schools of thought you can sift through to try and identify those tiny percentage of stocks that do well. Historically, managers have been pretty good at that. I keep coming back to, it's rational, it's logical, it's quantitative. The selling part becomes really squishy. First, every manager has a finite amount of money. Nobody has an infinite amount of money. Very often when something else comes along, well, we got to sell something to get the capital to buy something. You're selling early, you're not giving that stock that you put all this time and effort into researching enough time to develop in the fullness of its revenue and earnings growth. That's number 1. Number 2, we see a lot of fund managers when there's a little bit of a squiggle, when there's a little bit of issue, when a stock falls somewhat, they either panic and sell, or as we've also seen, when it's not just a modest pullback, when there's a fundamental change in the business model, when there's competition, when something happens that should make you go back to your original thesis and say, hey, the reasons I bought this are no longer in effect. We see other managers writing these stocks down to single digits from giant gains. All of these seem to be decisions that are emotionally driven. You have the hard mathematical buys, and you have the soft emotional squishy sells. That's why knowing how long to hold something and when to sell it. I feel like it's a lot more art than science, whereas the selection process seems a little bit of art, but a lot of science, as well. Selling is just much harder.

Andy Cross: Interesting. Sorry, Jason. Just a quick follow-up, is that the behavioral side to the decisions on the selling side is arguably more important than on the buying side.

Barry Ritholtz: That's right, because you can take a winning trade and give up the big wins, I described my terrible trade in Apple, which was a triple, worst trade I ever made. On the other hand, if you allow either your emotions or your just failure to understand why you own something to get in the way. Look, the reality is all of us investors are humans and we're filled with flaws. We weren't built for this. We adapted and evolved to survive in a hostile world, deciding how long to hold the stock was not part of our evolutionary history. When your fight or flight response kicks in. Someone just asked me, I don't understand. Investors underperformed from 2010-2020, a little bit, but they wildly underperformed in the 2000. Why is that? My takeaway was, well, 2010-2020 was pretty much straight up. 2015, Q4, 2018, not great. But it was a robust bull market. You just had to be invested and not make mistakes. Maybe people weren't fully invested, maybe they made some mistakes over that decade. The underperformance was almost triple in the 2000, and so you're coming off of the dotcom implosion. My experience, I just know firsthand, a lot of people entered '02, '03 wildly underinvested. They panicked out in '08, '09. We saw a capitulation, the bottom formed in March '09. Capitulation means surrender. People panic-sold in '09, and there's another study I referenced in the book that says, when people panic-sell, about a third of them never return to equities. If you want to know how you underperform by 5, 6% in 10 years, hey, tap out and miss the entire recovery that followed from March '09 forward.

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Jason Moser: I was fascinated at that statistic that so many people just don't even bother getting back in. I was taken aback by that. One of the things I really enjoyed about the book, I enjoyed the psychology, the behavioral aspects of it, and I like that you dug into the Dunning-Kruger effect. For those who are unfamiliar, can you explain what the Dunning-Kruger effect is and how it applies to investors?

Barry Ritholtz: [laughs] It's funny. I have family at University of Michigan, so I dropped a little footnote, and I'm shocked at how many people picked up on the go blue reference. David Dunning and his University of Michigan psychology professor and his grad student, Justin Kruger, did a study to determine if our metacognition, which is a fancy word for how good are we at evaluating our own skill set? The assumption tends to be that if you're good at something, you're pretty good at evaluating that skill set. It's not quite right. It's not quite a one for one curve. In the beginning, our metacognition of our skill set, when we have really poor skills, is awful. Even as we continue to develop skills in that, we're still far below where the experts are. It's more than just overconfidence. It's how hard can it be? I love asking a room full of people, how many people here are above average drivers? Three-quarters of the hands in the room go up, maybe more. I'm a car guy. I've taken every high performance advanced driving class there is, and they're all just thinly disguised defensive driving classes that try and teach you, stay within your own ability, stay within the car's ability. If you operate within yourself, if you make fewer mistakes, you'll just do so much better. Dunning-Kruger is not only the tendency for us to misevaluate our skill set and underappreciate how difficult a subject is. But then when you go to the other end of the scale and you talk to experts and you have them self-evaluate, they know how difficult things are.

They tend to underestimate their own skill set because they're aware of how random the world can be, how challenging and complex things are, that everything you do is dynamic and affects everything else, and then there's this feedback loop. The idea of Dunning-Kruger is our ability to self-evaluate improves over time, and it starts out really bad and eventually catches up as our skills get better. Now, apply this to investing. Look at what took place during the pandemic with Nubi traders and the checks that had gone out from the government and meme stocks and just, hey, how hard can this be? Those guys are a bunch of idiots. I can do this better than them. You see just the classic errors more than overconfidence, where the species as a whole is over confidence. We can't help it. If we weren't, wait, a bunch of us are going to go down with sticks and try and take down that mammoth. The cave that's overconfident goes down and does that, and they have fur and meat for the weekend, for the winter. Hey, maybe not everybody else comes back to the cave, but most of us are going to do better. The folks that lack that initiative tended not to survive. Pop Psychology 100, evolutionary biology, we have this tendency to a bias toward action. Of course, I think we could do this. Why wouldn't I? How hard can it be? That bias toward action leads us to doing things perhaps beyond our own ability. Takes a while for your metacognitive skills to actually develop so that it's not just that you have really good skills, it's that you're really good at evaluating where you are on that scale.

Andy Cross: Well, great words of wisdom from Barry Ritholtz. The book is How Not to Invest, Barry Ritholtz. Thank you so much. Really appreciate it.

Barry Ritholtz: My pleasure. Thanks for having me, guys.

Mac Greer: As always, people on the program may have interest in the stocks they talk about, and The Motley Fool may have formal recommendations for against, So don't buy or sell stocks based solely on what you hear. All personal finance content follows Motley Fool editorial standards and is not approved by advertisers. Advertisements are sponsored content and provided for informational purposes only. To see our full advertising disclosure, please check out our show notes. For the Motley Fool Money team, I'm Mac Greer. Thanks for listening, and we will see you tomorrow.

Andy Cross has positions in Alphabet, Amazon, Apple, Microsoft, and Nvidia. Jason Moser has positions in Alphabet and Amazon. Mac Greer has positions in Alphabet, Amazon, Apple, Microsoft, and Nvidia. The Motley Fool has positions in and recommends Alphabet, Amazon, Apple, Microsoft, and Nvidia. The Motley Fool recommends the following options: long January 2026 $395 calls on Microsoft and short January 2026 $405 calls on Microsoft. The Motley Fool has a disclosure policy.