
54 segments available
Barry Ritholtz — Make Fewer Errors, Make More Money | Episode 261 My friend Barry Ritholtz has spent his career being an astute market observer, investigating behavioral finance and data analytics. He runs Ritholtz Wealth Management which has been named ETF Advisor of the Year, Financial Times Top 300 Advisors, and one of America’s fastest-growing RIAs. He’s also the host of Masters in Business, Bloomberg Radio’s most popular podcast (50+ million streams/downloads), which he started way back in 2014. In his new book, How Not To Invest, Barry emphasizes how avoiding rookie mistakes can significantly help you do better financially. He blends engaging stories with data-driven insights, and explores overlooked aspects of behavioral finance, psychology and the market. Reading his book is like having a casual drink with an experienced, wise, and honest friend. I hope you enjoy this conversation as much as I did. For the full transcript, episode takeaways, and bucketloads of other goodies designed to make you go, “Hmm, that’s interesting!”, check out our Substack - https://8ca54796.streaklinks.com/CJPd0z7cXCh07hc4JAiMaKTC/https%3A%2F%2Fnewsletter.osv.llc%2F. Important Links: - Blog - https://ritholtz.com/ - Twitter - https://x.com/ritholtz - LinkedIn - https://www.linkedin.com/in/ritholtz/ - Ritholtz Wealth Management - https://www.ritholtzwealth.com/ Show Notes: 0:00:00 Intro 0:00:43 Main podcast 0:04:36 How Amateurs Win 0:11:36 Managing Emotions When the Market Goes Down 0:22:02 If You Can't Afford a Financial Advisor Yet... 0:37:25 Notable Financial Innovations 0:48:35 Barry’s Transition from a Trader to an Investor 1:01:17 Varieties of Investor Personas 1:07:02 What to Do When Randomness Derails Your Plans 1:13:37 Finding Your Own Maintainable Processes 1:17:43 Having Reliable Information Sources 1:25:03 Barry As World Emperor Books Mentioned: - How Not to Invest: The Ideas, Numbers, and Behaviors That Destroy Wealth - And How to Avoid Them; by Barry Ritholtz - Winning the Loser’s Game; by Charley Ellis - How We Know What Isn't So: The Fallibility of Human Reason in Everyday Life; by Thomas Gilovich
Barry Ritholtz discusses the pitfalls of amateur investing, comparing it to the experience of a novice winning at a casino. He emphasizes that successful investing is about avoiding mistakes and letting the market work for you, rather than trying to time the market or chase trends. The key takeaway is to stay out of your own way and allow compounding to take effect.
"The worst thing that can happen to someone who steps into a casino for the first time is that they win. Good investing is simple but not easy. Everybody's trying to find the next Nvidia. Everybody wan..."
Jim Oessy introduces Barry Ritholtz, highlighting his extensive experience in the financial industry as the chairman and CIO of Ritholtz Wealth Management and the host of Bloomberg's Masters in Business podcast. The conversation sets the stage for discussing Barry's insights on behavioral finance and his new book, 'How Not to Invest.'
"Compounding will take care of itself as long as you don't get in the way. Well, hello everyone. It's Jim Oessy with yet another Infinite Loops. Today I have my good friend who I think I've known you f..."
Barry shares his journey as one of the first financial bloggers, reminiscing about the early days of blogging in the late 90s. He discusses the challenges of coding and how advancements in technology have drastically improved productivity for content creators, emphasizing the importance of adapting to new tools.
"also one of the first bloggers. 2003. Actually, 1998 was the blind really on Geio Cities. And to tell you how old I am, Wow. I had to teach myself HTML to be able to post. And back in the '9s, it woul..."
Barry introduces the core concept of his book, 'How Not to Invest,' which focuses on making fewer errors to achieve better financial outcomes. He references Charlie Ellis's work on the 'loser's game' in investing, drawing parallels between amateur tennis players and novice investors who often lose by making unforced errors.
"when typad reached out and said, uh, six apart reached out and said, "Hey, we have this new blog software called Typad. It's Wizzywig. You don't have to do any coding." I'm like, "All right, I'll I'll..."
In this segment, Barry elaborates on the differences between amateur and professional tennis players, using it as a metaphor for investing. He explains that while professionals score points through skill, amateurs often lose by making mistakes. This analogy serves to illustrate how investors can improve by minimizing errors rather than trying to outperform the market.
"favorite Charlie's. A sentence that isn't said uh I don't think uh ever. So, so, uh, you go back to the 1970s and I know you are a market historian and a data junkie as am I, but um, Charlie Ellis was..."
Barry and Jim discuss the persistent challenges of human behavior in investing, despite having access to extensive data and historical insights. They reflect on the common traps investors fall into and the difficulty of recognizing one's own biases, emphasizing the need for self-awareness in financial decision-making.
"We double fault on a serve. We hit it into the net. We hit it wide. We hit it long. We hit it with not enough spin so it just bounces right up to the sweet spot of our opponent's um swing. And so if y..."
Barry shares a personal story about his biases as a Knicks fan, illustrating how emotional attachments can cloud judgment. He emphasizes the importance of recognizing one's own biases and blind spots in investing, encouraging listeners to reflect on their own decision-making processes.
"always have, Barry, is you and I have been saying this to people for 30 plus years. Sure. And yet human OS seems to be impervious to much of this what we think of as self-explanatory information data...."
In this segment, Barry discusses how investors often lack context when reacting to market fluctuations. He highlights the significance of understanding market history and the relationship between margin levels and market performance, stressing that context is crucial for making informed investment decisions.
"like 2011 2012 something like that. And um it was very eyeopening cuz up until that time it was everybody else. You're you're 100% right. It was well first of all frequently when clients call up freak..."
Barry explains how he and his team manage client expectations during market volatility. He emphasizes the importance of proactive communication and setting realistic expectations based on historical market performance, helping clients navigate emotional responses to market downturns.
"maybe it'll be a little easier to recognize those mistakes in yourself. Yeah. And uh it's sometimes uh I think we would both feel like Don Coyote, right? tilting at windmills because like I remember c..."
Barry discusses the reality of market corrections and how investors should view them as opportunities rather than setbacks. He encourages a long-term perspective, particularly for younger investors, and emphasizes the importance of being prepared for market fluctuations.
"I'm walking I'm walking into his office Barry this is February of09 okay so you you know what happens afterwards right I'm walking into the office. He's got a beautiful office in DC. He stops me. He's..."
Barry draws parallels between military training and investing, highlighting the importance of preparation and having contingency plans. He shares insights from senior traders about the necessity of being mentally prepared for unexpected challenges in the market, reinforcing the idea that emotional control is key to successful investing.
"How do how do you and your colleagues uh at your shop, how do you stop your clients from doing this? So, there's there's a couple of ways to bring people to a headspace where market turmoil doesn't af..."
In this segment, Ritholtz explains how financial advisors can help clients avoid panic selling during market downturns. He discusses the concept of 'advisor alpha' and how effective guidance can prevent costly mistakes. Ritholtz emphasizes the value of having a trusted advisor to navigate emotional challenges in investing.
"insightful and helpful to say not only do you have to in intellectually anticipate the ordinary course of events where markets will fall 3 4% in a day, 20% in a quarter. But you have to imagine what y..."
Ritholtz delves into the concept of market capitulation, explaining how it signifies a point where many investors give up and sell their holdings. He notes that a significant portion of those who panic sell during market lows never return to equities, which can have long-term consequences for their financial futures. This segment underscores the importance of maintaining a long-term perspective.
"them, they are deep into that. They spend a lot of time um Josh had a had a really great comment in the morning meeting today. This sort of environment is where advisors earn their keep. It's where ad..."
Ritholtz offers practical advice for young investors who may not yet have the resources for a financial advisor. He encourages them to utilize his book, 'How Not to Invest,' to understand the basics of investing and to build a diversified portfolio. Ritholtz stresses the importance of managing behavior and staying informed to avoid common pitfalls.
"sticky wicket. Uh I used to when I started my career I was going to publish these books say here's a level playing field here's how you can do it you can do it yourself and then I had you know years a..."
In this segment, Ritholtz outlines the fundamentals of creating a diversified investment portfolio. He advocates for a core strategy based on low-cost index funds and discusses the importance of rebalancing. Ritholtz also addresses the role of fixed income in a portfolio, particularly for younger investors, and encourages them to focus on long-term growth.
"you know, it's an old joke, uh, gamblers joke. The worst thing that can happen to someone who steps into a casino for the first time is that they win. And similarly, the worst thing that can happen is..."
Ritholtz emphasizes the significance of compounding in long-term investing. He explains how dollar-cost averaging can help investors navigate market fluctuations and ultimately benefit from market recoveries. This segment highlights the importance of patience and maintaining a long-term investment strategy to achieve financial success.
"know we've been looking at Europe as a perennial lagard. All right now the US seems pricey enough and Europe seems cheap enough. If you want to add a a Europe ETF, go ahead. And you know, the idea is ..."
Ritholtz discusses the dangers of emotional trading and the impact of media on investor behavior. He stresses the importance of sticking to a process and not letting short-term market noise dictate investment decisions. This segment serves as a reminder to focus on long-term goals rather than reacting to immediate market conditions.
"way, if you continue to dollar cost average as some people did from 20 to 2013 and the stories abounded in in ' 66 to 82, think about how frustrating that must have been for the 13 years between the d..."
In this segment, Ritholtz shares insights on assessing a potential client's risk tolerance. He explains how recent market events can skew perceptions of risk and emphasizes the need for a broader context in understanding an investor's true risk profile. Ritholtz highlights the challenges advisors face in accurately gauging client attitudes towards risk.
"probability for successful outcomes. Yeah. And I've I've often said uh good investing is simple but not easy. And it's that part where I just continually try to come up with ways and you're very good ..."
Ritholtz reflects on the changes in financial media over the years and how they affect investor behavior. He contrasts the past with today's 24/7 financial news cycle, emphasizing the importance of maintaining perspective and not getting caught up in daily market fluctuations. This segment encourages investors to focus on long-term strategies rather than short-term noise.
"you have a sense of okay, this is going to be a great client or oh my god, this is not going to be a great client. So very often every the recency effect colors everything everybody says and done does..."
Ritholtz introduces the concept of 'time travel' in financial planning, urging investors to think about their future financial needs rather than getting caught up in short-term market events. He uses a humorous analogy of 'morning Barry' and 'nighttime Barry' to illustrate the importance of planning ahead for retirement and long-term goals.
"you know I I'm a um I'm a big watch guy but not for the reasons you would think. I became a watch guy as a kid because I was fascinated by the concept of time, right? So, we see each other because pho..."
Barry highlights significant innovations in the financial sector over the past decade, particularly the rise of ETFs and the ability to trade with minimal costs. He discusses how these innovations have improved investment strategies and tax management, while also cautioning about the potential downsides of free trading platforms.
"And the way you time travel is not getting into HG Wells time machine or or a TARDIS and travel um somehow always back to London. But um but just picture yourself what's the world going to be like in ..."
Ritholtz elaborates on the implications of free trading, noting both the advantages and risks associated with it. He reflects on how the ease of trading has led to reckless behavior among inexperienced investors, emphasizing the need for education and awareness in navigating the modern investment landscape.
"What do you think about what another thing that we have seen uh I think some of it very good some of it really not great for investors is over the last 1015 years there has been a huge amount of innov..."
In this segment, Barry discusses the evolution of tax management strategies in investing, particularly through direct indexing. He explains how this approach allows investors to optimize their portfolios by realizing losses without affecting overall performance, ultimately leading to significant tax savings.
"Sure. And and and by the way, the genesis of this section in the book comes from the very amusing quip from former Fed chair Paul Vulkar who said, "There's been no innovation in finance other than the..."
Ritholtz emphasizes the importance of client education in the face of increasing cyber threats and scams. He shares practical advice for clients to protect themselves from fraud, highlighting the need for vigilance and awareness in today's digital investment environment.
"a buyer at 24 and an eighth and I'm a seller at 24 and 78 and you would get filled and eventually the market shrinks those um spreads. Now the spreads are tiny so you're not paying up when you want to..."
Barry reflects on the current state of investing, describing it as a golden age due to the accessibility of information and trading. He encourages investors to take advantage of these advancements while remaining cautious of the inherent risks that come with them.
"sitting on you know if you're in any of the forget even magnificent 7 it's like the top 50 stocks you're sitting on massive gains uh founders stock IPO shares low cost basis inherited stock employee s..."
In this segment, Ritholtz discusses the alarming rise of voice scams and the implications for public figures. He shares personal anecdotes about the dangers of identity theft and the need for heightened awareness to combat these sophisticated scams.
"straightforward. So, that's another innovation. Um, just to show you how how much the world has changed. And let me again reiterate the free trading and on apps like that have gified trading like Robi..."
Barry shares his personal journey from being a trader to adopting an investor mentality. He reflects on the skills required for each role and the gradual transition that shaped his approach to investing, emphasizing the importance of self-awareness in this process.
"crap. The IRS literally put out 42 things or 39 things that are not true that keep showing up on social media. You I I linked to uh I think it's a footnote, the actual URL uh in the book. Um, but ther..."
Barry Ritholtz discusses the increasing risks of fraud and scams in the era of easy access to trading and financial accounts. He highlights the dangers of voice cloning technology and the importance of verifying communications, especially for public figures. This segment emphasizes the need for vigilance against sophisticated scams that prey on vulnerable individuals.
"aware of the risks that happen that are the other side of the double-edged sword. The excrading for for free trading or the fact that you can so easily see your accounts and access money and move it m..."
In this segment, Barry reflects on his transition from a trader to an investor, sharing insights on the different skill sets required for each role. He recounts his experiences on the trading floor and the emotional challenges faced by traders, illustrating how understanding behavioral finance shaped his investment philosophy.
" Because half the time these are, you know, public figures and AI, you can make them say anything. Yeah. And uh I' I've I've had that demonstrated and it's really freaky. Uh little scary. and an acqua..."
Barry Ritholtz delves into the emotional errors that traders often make, referencing the book 'How We Know What Isn't So' by Thomas Gilovich. He discusses the psychological factors that lead to inconsistent trading results and the importance of self-awareness in making better investment decisions.
"trader mentality, which requires a really different kind of skill set than an investor mentality? H how did you walk me through that transition? Did something happen? What was it? Was it was gradual. ..."
This segment explores the risks associated with doubling down on losing trades, as Barry shares a vivid example from the late 90s involving the collapse of MicroStrategy. He emphasizes the importance of risk management and the existential risks traders face when they ignore warning signs.
"um in I want to say it was like 96 or 97 I read a book from Cornell professor Thomas Gillovich called great book how we know what isn't. So certainly the first twothirds of it is just a deep dive into..."
Barry discusses his decision to move from trading to research and analysis, highlighting the importance of stability in investment strategies. He reflects on the lessons learned from his trading days and how they informed his approach to becoming a chief investment officer.
"isn't US. This is And the guy who actually released it eventually got arrested and the stock was like 120 and it had fallen to 20 or 30, some crazy number. And it recovered to like 60 or 70. There sti..."
In this segment, Barry explains the concept of beta and its significance in long-term investing. He contrasts active management with a more passive approach, arguing that simply capturing market returns can lead to better outcomes over time, especially when considering the sequence of returns.
"trading desk. So, so the decision was made. I moved into research. I worked for a guy named Larry Hart, who was a former software programmer at the predecessor to Lucen, uh, Bell Labs. This was at Pri..."
Barry shares insights on the nature of investing, quoting Nobel Laureate Paul Samuelson. He argues that successful investing should be a steady, boring process rather than an exciting gamble, emphasizing the importance of patience and long-term thinking in achieving financial success.
"statistically in any given year, statistically you're going to end up bottom 10 or 20%. There's no way around it. Your geography, your style, your um investment focus, everything comes in and out of f..."
This segment highlights the importance of proactive communication between financial advisors and their clients, especially during market downturns. Barry discusses strategies for keeping clients informed and reassured, emphasizing the need for transparency and support in challenging times.
"Yeah. And and I just keep coming back to that because, you know, I've thought of many different stories, many different ways to explain that. And some of them land, most of them don't. And you you kno..."
Barry discusses the current economic landscape, addressing concerns about potential recessions and market volatility. He emphasizes the importance of being prepared for various scenarios and the need for financial advisors to stay engaged with their clients during uncertain times.
"saying, "Hey, we don't know where this ends." Maybe this is a quarter to a third of the way through. Who knows? But it it, you know, otherwise the economy is doing fine. And even if all of this crazin..."
In this segment, Barry reflects on the characteristics of successful investors he has encountered throughout his career. He shares insights from his extensive podcast interviews, highlighting common themes and traits that contribute to their success in the financial markets.
"because we know we're not selling alpha. We know that this is what happens. Markets go up and down. And it's why in the beginning of 2025 we said lower your expectations for when you have back-toback ..."
Barry Ritholtz shares insights from his extensive interviews with top investors, highlighting the diverse characteristics and strategies that define successful investing. He discusses notable figures like Howard Marks and Bose Weinstein, emphasizing the common themes of adaptability and insightfulness in their approaches to the market.
"Right. Um who over your career uh you've written a lot of books, you've uh met a lot of really fascinating people. who in your mind who are some of the better investors that you've met over your caree..."
In this segment, Ritholtz reflects on the importance of luck and serendipity in the careers of successful investors. He recounts how even the most accomplished individuals attribute part of their success to fortunate circumstances, underscoring the unpredictable nature of the market and the necessity of being prepared for unexpected opportunities.
"So, let me just throw a couple of names out because they're so different in in what they do. So, you know, I take a Howard Marx who is a distressed fixed income investor and put up like an amazing tra..."
Ritholtz discusses the intersection of preparation and opportunity in investing. He emphasizes that while randomness plays a significant role in success, being well-prepared allows investors to capitalize on unexpected events. This segment highlights the balance between hard work and the unpredictable nature of the financial world.
"on things like Nvidia um you're you're ahead of of everybody else And then you know there's some other really fascinating people. Bose Weinstein runs a hedge fund and he is constantly looking at inter..."
Barry Ritholtz elaborates on how randomness affects market predictions and investor behavior. He argues that many fail to account for random events that can derail plans, such as geopolitical crises or economic downturns. This segment encourages viewers to embrace uncertainty and prepare for the unexpected in their investment strategies.
"but I'm kind of fascinated by that. Um I've I've interviewed Steve Cohen once or twice. certainly an intriguing guy. Dimmitri uh Bolosni, another really intriguing guy. But here's the thing that I fin..."
In this insightful discussion, Ritholtz explains the concept of 'cost of admission' in investing, where market volatility and downturns are part of the journey. He reassures listeners that experiencing losses is not a personal failure but rather an inherent aspect of investing, emphasizing resilience and understanding in the face of market challenges.
"That's just table stakes to enter the arena. He goes, I I've been really fortunate, right place, right time, certain things went my way and there was this event and this meeting and this coincidence a..."
Ritholtz shares personal anecdotes about navigating market volatility and the emotional challenges that come with it. He reflects on moments of doubt in his career and the importance of maintaining a philosophical approach to investing, which helps in managing stress and uncertainty.
"down the list of these, you know, amazing people who have built Bill Gross and, um, uh, Jeff Sherman over at Double Line and Jeff Gunlock and, uh, Jeremy Seagull and and Jeremy Schwarz at Wisdom Tree...."
In this segment, Ritholtz discusses the significance of having a personal investment philosophy. He emphasizes that a well-articulated process can guide investors through turbulent times, allowing them to remain grounded and focused on their long-term goals, regardless of market fluctuations.
"a lot to be said for I don't love the phrase creating luck, but being prepared for when opportunity presents itself because, you know, every now and then there's a situation where something happens an..."
Barry Ritholtz stresses the necessity of having reliable information sources in investing. He advises against being overwhelmed by media noise and encourages investors to curate a trusted network of experts to guide their decisions, enhancing their understanding of market dynamics.
"serendipity. And so after the, you know, the hundth wildly successful finance person says always be grateful, you know, Scott Galloway at NYU who's, you know, by any measure wildly successful. His lin..."
Ritholtz reflects on the randomness of success in investing and life. He discusses how acknowledging the role of chance can help investors maintain perspective and resilience, especially during challenging market conditions, reinforcing the idea that not all outcomes are within one's control.
"economy in geopolitics. I think the reason year out forecasts people do so poorly with them is that they completely underestimate how often a random event like a pandemic, like the Russian invasion of..."
In this candid segment, Ritholtz shares a personal story about a pivotal moment in his investing career during the MCI WorldCom merger. He recounts the stress and uncertainty he faced, illustrating the real-life implications of market events and the lessons learned from navigating such challenges.
"the screen, it it's what the price the the hard part, the uncomfortable part is the cost of admission for the gains. And it's nothing that you did wrong. It's just something you have to tough out for ..."
Ritholtz discusses how his investment philosophy has evolved over time. He reflects on the importance of adapting one's approach based on experience and understanding, highlighting that there are multiple paths to success in investing, each requiring a thoughtful and articulated process.
"you recall the MCI WorldCom merger does Oh yeah, sure. Yeah. So, it was one of those days where half the office is out and hey, let the newbie, let the rookie man in the terminal. So, I'm watching all..."
In this segment, Ritholtz addresses how to support investors who are experiencing doubt and uncertainty. He emphasizes the importance of clear communication and understanding, encouraging investors to focus on their processes and the value of reliable information sources to alleviate stress.
"you. You're going to handle the taxes and everything else. You're just going to give me, you know, here's here's a hundred grand. Give me 30. Deal with the rest. He's like, done. So, I did that with a..."
Ritholtz concludes with insights on the importance of effective communication in investing. He stresses that not all investors are ready to hear certain messages and that understanding this can help in guiding them towards better investment practices without imposing one's beliefs.
"you know this is the way, this is the future, this is what you've got to do. And then I realized that there were many more paths to heaven. But what underlay all of them was an articulated process tha..."
Barry Ritholtz discusses the difficulty of changing entrenched beliefs in investing. He emphasizes that not everyone is receptive to new ideas, regardless of how well-articulated they may be. Ritholtz highlights the importance of selecting reliable information sources and building an 'all-star team' of experts to guide investment decisions, rather than succumbing to the noise of media and social platforms.
"happened. The new book I'm like, hey, you know what? I understand there are people who are going to want to believe stuff regardless of whether it's right or wrong. They have their their uh I almost w..."
In this segment, Ritholtz reflects on the feedback he receives from followers who successfully navigated market downturns by heeding his advice. He shares anecdotes about the importance of recognizing what is in one's best interest and how some individuals are more receptive to learning from past mistakes. Ritholtz also discusses the challenges of writing about complex financial topics and the joy of sharing valuable lessons through storytelling.
"you know, you could put them on your all-star team, and it doesn't have to be anyone masked head. It's these people at Barrens and these people at Bloomberg and these people at the Wall Street Journal..."
Barry Ritholtz emphasizes the significance of humility and the power of compounding in investing. He explains how understanding the limitations of our knowledge can lead to better investment decisions. Ritholtz illustrates the compounding effect with a metaphor about two individuals investing money, highlighting the vast difference in outcomes over time. He encourages listeners to start investing early and to allow the market to work its magic without interference.
"everybody to understand what's in their own best interest, but some people will pay attention to this. Maybe some people will be somewhat entertained by it. I tr you know, bailout nation was kind of a..."
In this concluding segment, Ritholtz shares his key takeaways for successful investing: the importance of starting early and not interfering with the compounding process. He discusses how even small, consistent investments can lead to significant wealth over time, using historical examples to illustrate his points. Ritholtz encourages a mindset of patience and humility in the face of market fluctuations, reinforcing the idea that compounding can lead to extraordinary financial outcomes.
"gravy. For us that gravy is tax alpha advisor alpha and the ability to educate people about what is real and what is not. What made this book such a pleasure to write? It was really a joy to write aft..."