My First Million - Brutally honest guide to not losing money in the market

Episode Date: June 10, 2026

Get our Investment Guide: https://clickhubspot.com/klsr Episode 832: Sam Parr ( https://x.com/theSamParr ) and Shaan Puri ( https://x.com/ShaanVP ) talk to legendary fund manager Barry Ritholtz( https://x.com/Ritholtz ) about the behaviors that destroy returns for investors and how to avoid them.  — Show Notes:  (0:00) Intro (2:19) christmas tree portfolio (4:43) the cowboy account (9:51) day trading (11:09) Barry yells at Lloyd Blankfein (13:46) panic selling (16:45) sam picks a fight (18:46) direct indexing (21:43) Great investors  (27:25) 90% of everything is crap (36:14) Elon's foray into PE (44:02) Predicting the housing crisis (46:01) spending a year as the dumbest guy on wall street (49:01) Why bubbles are good for the economy — Links: • How Not To Invest - https://www.hownottoinvestbook.com/ — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com  • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies! Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

If you could tell me something in the next 15 minutes that would make me a better investor, what's the first point you would just hammer into my head? Oh, my God. Put the fucking phone down. Stop trading. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off.

On a road, let's travel. Never looking back. So I think the interesting place to start is we've had a few different people from the school of investing wisdom come on. sort of the value investing genealogy. And me and Sam, although we are not investors, we're definitely like entrepreneurs first and then investing as a sort of hobby, sport type of thing, we're so attracted to it.

We love the sort of investment wisdom, especially your version, which is the awshucks common sense version of investing, which is less about how to be super smart and do advanced things and just how to be less stupid than you already are, and don't worry, you'll be fine. And so I'm excited to talk to you.

You have a cool story. You started off really in the content game, in the media game, blogging back in GeoCities, early on with podcasting and built a large investment advisory shop called, named after yourself. I think you guys got to what? That was a placeholder, by the way. That was not supposed to be permanent. Like, let's just call it Ritt Holtz for now. Someone else said, and we'll find a better name, and then we never found a better name. The background is go to law school.

really well, hate being a lawyer. A client is running a trading desk that was a predecessor shop to e-trade. And so I started on a trading desk and found it was just mayhem. It was just random and volatile. And I was more fascinated by why the people around me, some days were killing it, some days were getting killed. Like, what's going on with their process? And that sent me down the rabbit hole of behavioral finance. It just was the only explanation I found as to why the same person could be doing really well one week and applying the same process gets shellacked the next week. It's decision making, it's emotions, it's cognitive biases.

Can you explain your Christmas tree analogy for constructing a portfolio? Sure. That's really easy. So we know that historically, very few people beat the index on a regular basis. In any given year, less than half of active managers beat their index. You take that to five-year, it's something like 21%. You take it to 10 years. It's less than 10 percent, one out of 10 people.

So that includes, like, huge firms. Includes everybody. Any active mutual fund, ETF, hedge fund, whatever. and then go to 20 years and it's a handful of names you know, Peter Lynch, Warren Buffett, etc. So if the core of your portfolio is a broad index, you know, you can't get alpha, meaning outperformance, if you're not at least starting with beta.

And when we say people don't beat their index, it means not only are they not getting what the market gives them, they're getting less than that. So forget beating what the market gets. They're not even getting what the market gets. So pick a number, 50, 60, 70% of your portfolio is that core. And by core index, I mean U.S. Broad-Based Market indexes. Vanguard's VOO last week became the first ETF over a trillion dollars.

And that's just a super low cost, broad index. You want to own some overseas stocks that overseas indexes. That's fine. Now, the tree is the garland, the decoration, the lights, the tinsel. That's whatever stink of your. own you want to put on your portfolio. So if you like momentum, great. You want a little more tech. However you want to decorate it, you know, we've looked at these assortments of different portfolios. They all more or less end up in a similar place. Some are a little better, some

are a little worse. They all end up trailing the index. If two-thirds of your money is in a broad index, well, at least you know you're starting with that basis point. And, hey, I I think Japan is great. I'm going to own EWJ, or I think India is the next big country after Korea, so I'm going to own that ETF. If you want to have a little bit of decoration on the tree, that's fine. Just recognize you're aiming to outperform, and the odds are very much that you're going to underperform. So is this a little bit like when you do a diet and they're like, yeah, we're going to do a cheat meal on Sunday. And it's not that the cheat meal is good for you.

It's just that it's probably the only thing is going to keep you. on the guardrails of the other six days of the week being on track. Is that why you even have the decorations, or would it just be better to be 100% in the passive index, it's call it a day? So my cheat meal is the cowboy account. We have clients, listen, what's more fun, what's sexier than talking about investing in startups,

investing in the hot new publicly traded technology? You look at all the things that we talk about, the media, television, print, web. it's never about own a broadly diversified portfolio of low-cost indexes, rebalance every few years, seeing a few decades. Now what do you do with the other 23 hours and 59 minutes a day? You have to fill it with content. So all this sexy news, all this exciting stuff, that's 90% of the fire hose you see.

Would that be the best finance channel? They just say that at the top of every hour, and then they just play like home alone reruns for the next 15? 59 minutes. And actually those investors would do way better than anybody watching the NBC. I tell the metaphor of this little gardening channel and they have a tree cam. They plant a tree and it just, it's very bucolic and relaxing. And it's just there and everybody is happy with it. And then the channel gets bought by private equity. And now they got to sex it up. So everything becomes a fake conflict. That's the wrong tree for this area. Too much water. You planted a two deep. No, it's not deep enough. It's not getting enough. And meanwhile, the tree could not care less

about what they're saying. It just quietly grows. And that is how I think of the media and the broad index. Say what you want. Vanguard and BlackRock have between the two of them have $25 trillion in assets because they've dominated low-cost indexing. And I think the financial crisis was very much the last straw for mom and pop investors. Now you have a whole new generation of people on draft kings and Robin Hood speculating, but everybody who's over 40 kind of lived through this and said, you know what, I'm going to take my ball and go home. And by ball, I mean capital.

And by home, I mean Black Rock and Vanguard. And, you know, before 0809, Vanguard was under a trillion dollars. They're like $11 or $12 trillion. dollars, Black Rock is 13 or 14 trillion. Like, these are giant, giant firms. And so that's kind of what happened. That's the base core. And, you know, the tree just keeps growing.

What's the biggest return one of your clients has had via their cowboy account? So we've had people that have had some Bitcoin when it skyrocketed. We've had clients that had a lot of Tesla that blew up, you know, in 20 and 21. it exploded, heading into the pandemic, the people that in their account had like Teledoc and Zoom and Peloton, and they just exploded. But what always happens, it's so hard to sell something because most of our cells, like I owned Apple when the iPod, not iPhone, iPod came out. It was $15 a share, 13 cash.

There's no downside. And it tripled. It went up to 45. And I thought I was a genius selling it. And then it proceeds to gain another 9,000 percent. But we've seen that. You know, one of my favorite stories in the book is the CEO of Peloton wasn't getting especially great advice.

At one point on paper, he was worth, I don't know, two or three billion dollars. And just leveraged himself to the health, bought a whole bunch of stuff. Then, of course, as the pandemic starts to, as the vaccine starts. going around and we start to see the light at the end of the tunnel, Peloton crashes. He must have taken a whole bunch of stock loans against that capital, had a $60 million place in East Hampton, had to sell that, was just liquidating everything. And just, you know, it's always a shame when you see that. I mean, how many disasters do we have to live through before you realize any stock can go to zero? So anytime you're trading an individual name,

The odds, Hendrick Bessonbinder at Arizona State Business School did a couple of studies, and he basically found out that the entire value in the market comes from between 1 and 2% of stocks. So what are the odds, 50 to 1, 100 to 1, that the company that you love so much that's run up so much this year is going to do it for another 10 or 20 years? You want to hear something funny? Sean, we did a podcast with Lloyd Blankfine the other day. You know, the... Yeah, he's got a book out. Yeah, it's a great book.

And he's, you know, for the listener, he's the former CEO of Goldman. He's a big shot, a great guy. He told me, I was like, you're retired. What do you do now? He's like, I love to day trade. He was like, he goes, in fact, I knew I was going to do this podcast for two hours. And it kind of made me anxious because I'm always grabbing my phone to look at like my stocks. And so I had to put all my orders in advance in preparation.

because I'm not going to be available. And he's like, right now, I want to look at my phone right now. And then after the podcast, I was like, well, what do you going to do now? He's like, well, market's closed, so I don't have anything else to do. I guess I'll walk home. And I don't know how his portfolio, he said 70% of his net worth. I think he said that. Don't quote me, but something like that is in his pickings.

And so he said he's doing good. But it was just so funny. And what's interesting is that I'm sure he's doing great. If anyone's going to do great, it's probably someone like him. That said, it's like even if you're a titan of industry, you're on top of the world, you know everyone, you're a who's who. There's probably a world where he's going to make every single mistake, the same mistake that an 18-year-old degenerate Robin Hood trader is going to make. And I find that's interesting that we all still do these things. Lloyd, listen to me.

Put the fucking phone down. Stop trading. 70% of your net worth should be in muni bonds, paying you a huge tax-free yield. you want to dick around with a few million dollars, knock yourself out. But if you're actively trading 70% of your net worth, which is a couple of billion dollars, I am disappointed to tell you that you are making the biggest risk-adjusted mistake of your career. And the schmuck that used to run Goldman Sachs should know better. Stop day trading.

Looks like I'm not invited to, I'm not invited to Shabbat dinner anymore. So thanks, Barry. Oh, my God. I hope your memory, your numbers are wrong. So here's the fascinating behavioral side of that. On this show, we have spent hours talking to some of the best investors alive. Well, lucky for you, the team at HubSpot, they have pulled out the principles that matter most and turned it into a very simple, easy to read, wealth guide.

It's 35 principles from the top investors. We're talking guys who have been on the pod like Howard Marks, Manich Perbri, Morgan Housel, Kathy Wood and a ton others. So these are all their frameworks, their mental models, their rules, basically how to play the long game and how to avoid ruin. You can get it in the link below.

We see this all the time. I mention the clients, hey, do I buy a Ferrari or not? The folks who are, and I mean this in all seriousness to Lloyd, people who, a guy like him, works really hard his whole career, constantly striving and saving

and investing and putting money away and accumulating stock options and going through all this, it is really difficult, even for people who are, you know, masters of the universe, billionaires, to recognize and just stop and say, I won.

Hey, I won. I don't have to put this much capital at risk because over the decades, I have just seen that story play out and end badly. Hey, I'm sure Lloyd will be fine. He doesn't have to take financial advice. from little o me, but anybody who walks into the office with a giant portfolio, the challenge is how do we convince you that you've won and how do we make you create a portfolio that is

highest probability of reaching whatever your goals are? And P.S., if your goal is just more, well, then you're going to be disappointed both in your portfolio in your life. You mentioned something about selling, and I thought there was two interesting things in your book about selling. One was about panic selling and the data around what happens for panic selling. The other was that there was some study about hedge fund managers where their buys were actually good, but their sales were terrible. And I wanted, can you explain those two ideas around selling? So again, a lot of behavioral finance research behind this. It turns out that people panic sell into a market crash, something like a third of them never

returned to equities. So let's just use either the 2020, 34 percent pandemic sell off or more likely the 0809, 57 percent market crash. Imagine selling down 57 percent, not getting back into equities and watching 15 percent a year compound over that entire period. it's shocking. So you take a million dollar portfolio, you're out at like of 450,000 net worth. If you never would have sold it, it would be worth 10x today. It would be 4.5 billion. And to be fair, you are getting a percent or two up until 2022. Now you start to get 4 percent in a money market,

3.7 percent today. But that doesn't compare to a 10x and it doesn't keep up with inflation. So that's the first data point that's shocking. Panic sell into a portfolio, one and three people never get back into equities. The hedge fund, the buys are good, but the cells are worse than just if they sold at random. So I love this study. It's by Alex Emus, who is a University of Chicago professor, but they did this study where they looked at all these buys. And my explanation is the buys a rational spreadsheet database. The cells are always emotional. But the clever thing that Professor Emis did was, hey, how can we tell how good these cells

were? I know, instead of selling the company that the manager wanted to sell, let's randomly pick anything else that's in this manager's portfolio and sell that instead. And it turned out that the random cells outperform the manager's. collected cells by something like 150 to 200 basis points. Maybe it was even more. It was some crazy amount. And it's like it makes sense that the buys are thoughtful and logical.

But the cells very often are emotional, impatient. You know, sometimes the stock doesn't work out right away. People sell it, even though the underlying thesis was correct. Sometimes something else bright and shiny comes along and you got to sell something so you have money to buy that. It's an amazing data point, and it just goes to show you, most of our decision making is bad, and so one solution, make fewer decisions. Hey, can I, I'm going to pick a friendly fight with you. Sure.

So you say buy low-cost index funds. I'm on board with you. Anyone who's listening to this pod knows you're speaking my language. But why would I pay you a fee then to do that? You don't have to. Our whole business model from day one has been, so we've been writing in public, myself and my partners. Hey, you could do this yourself. You don't need anybody.

You just need put together a broad portfolio of low-cost indexes, manage your own behavior, stay out of your own way, and, you know, check in on it once, twice a year. That's it. And there are a bunch of people who said, well, I like the advice, but I have a little more complexity in my portfolio. I have tax issues. I have state issues. I have whatever. I need some help with this. We don't have minimums.

We set up different levels of, we have two digital platforms, one for under a quarter million dollars, and one for a quarter million to a million. But our whole, our whole, you know, line of bullshit has always been, do it yourself.

You don't need our help. And it turned out, something like 0.01% of our readers said, I don't have the time. I don't have the discipline. I'm not interested in this crap. I pay someone to do my taxes.

I pay someone to mow my yard. I'm going to pay you guys to manage our money. I did a post a couple of weeks ago about organizational alpha. And if you beat the market by 50 basis points or below the market by 50 basis points, clients could not really care less about that. However, if you manage to quarterback their finances in a way that our tax team has done a great job minimizing capital gains taxes. We use a couple of complex products,

and I always think simple is better than complex, unless it really solves a sticky problem. So direct indexing really helps with that. Sam, do you direct index or do you know what that is? Yeah, I know what it is. I don't do it. Sean's people make fun of me, Barry, on the show, because I am a very strict, like at this point, it's a little bit like 90-10 equities and bonds.

But I don't even think you need the 10. 30 years before you need the money, why drag the portfolio down with bonds? Which, by the way, is somewhat controversial. It just helps. It's a mostly emotional decision, but direct indexing. It's summarized as instead of buying an index fund, you have a program that basically buys the stocks of the index. The components, right.

The components of the index in the same proportion. It seems like over the course of, like, for example, the way that my personal finances are set up, I don't intend, I live off my income. I don't ever intend to sell my direct or my index portfolio in case, I guess I would sell an emergency. But why would I do direct indexing if I don't intend to sell it? I love that question. So you guys have both sold startups and ended up with substantial capital gains. And so in any given year, even when the markets are up, there's some 20, 30, 40 percent of stocks that are down.

And of that group that's down, there are some that are down substantially. So if you have Voo, I think, is 700 or 800 positions, the S&P 500 is 500, you look at the bottom desile, the bottom 10% of stocks. And all right, this small cap biotech is down 40%. I'm going to sell it and replace it with something that looks very similar, another small cap biotech that's down in the same space. I harvest that loss, the portfolio value doesn't change. The way the portfolio trades doesn't change.

But if you do that every year, you could pick up 75, 85 basis points. In Q1 of 2020, when the market was down 34%. O'Shaughnessy did a research study on direct indexing. Their study said that it was 400 plus basis points of losses harvested and replaced with very similar companies, and when the recovery happened, it matched the performance of the index because effectively it's the same thing. So founder stock, IPO stock, sale of a business, inheritance, high concentration positions, every now and then someone comes in and says, hey, I have a $10 million portfolio.

And when I've owned fill in the blank Apple for 15 years, and now it's 90% of my portfolio. How do you get them out of that position without paying a giant cap, gains tax. And so this has been like a very effective way to, uh, to do that. Uh, it's not for everybody. It adds complexity. It adds a little bit of cost, not much, but some. Um, but it's definitely useful for that. For most people, I don't think it's necessary. Hey, let's take a quick break. You know that feeling when strategy is done, the brief is written, everyone's aligned, and you realize someone still has to sit down and actually create all the content. That someone is usually you and it's due tomorrow. Well, the breeze assistant from Hub,

can help. It works right inside HubSpot. You can draft campaign copy, blog posts, emails, all in your brand voice, all using your actual customer data. So you don't create just content. You create content that converts. Check out HubSpot.com, the agentic customer platform for growing businesses. Can I ask you a bunch of stories? I want to do a story time thing because the cool thing about you is you've been doing the content game for so long. And so I know you've met some incredibly interesting people. I want to do a little rapid fire bit. Of all the people you've had on the podcast or interviewed at conferences or through work, who's the person who you think our listener should research and someone you admire? So you mentioned Ray Dalio and Howard Marks.

Those are obvious. I'll give you a couple of really interesting names. Richard Barton is this former Microsoft employee who founded Expedia and Zillow and just one crazy company after another. He's got this crazy framework. I think Sean and I have talked about it. His whole, I think I'm summarizing this correctly, Sean. I think he said his whole career is taking messy data and organizing it. Or I think he even said, I free the data. Yeah, he calls it, give the power to the people.

It's basically take data that exists that is just not transparently, easily structured, and available, and make it transparent, easily structured, and available. And so if you look at what he did with housing, you know, the housing data, that's the MLS data. he made it more easy to access through Zillow. They did it with Expedia. He did it with Glassdoor. And it's the same thesis he's just played out in like four, you know, plus different companies at this point.

I'll give you a couple other names that are a little below the radar, even though they're all kind of known to the industry. I think David Rubinstein of the Carlisle group could be the best human being I've ever met in my life. That guy's awesome. Have you seen a show, Sean? Yeah, of course. I'm just saying this.

I didn't know he was such a legend. I just thought he's an interviewer because I had just only ever seen him doing interviews. I didn't realize he was the founder of Carlisle. And he's like a, he's a, I knew him as like a historian. He has these amazing books. I'm reading one of his books on Washington and Lincoln

and the rest of the presidents. I don't even think of him as a money guy. So he started out in the D.C. area when Carlisle started. And he would put together these, off the record conversations with experts in spaces that were being debated by Congress. And then he would invite a whole bunch of congressmen and senators and staffers from both sides. And the idea was, this isn't partisan, this isn't political. This is just a way for you guys to hear from an expert who you may not come across.

And why did he do that? He was in politics? No, he just wanted the Congress of the country he lived in to be better informed and make better, more knowledgeable. But was he a big shot when he did that? No, he was, Carlisle was a tiny little company that was specializing in a telecom, and that's why they were based in D.C. And eventually expanded to everything else. So later on his career, he's super becomes wealthy. And the Washington Monument starts falling apart.

the cement starts cracking. It's a couple hundred years old. And Congress being paralyzed and incompetent, he's an idiot and a congressman, but I repeat myself, is the Mark Twain quote, they couldn't get their shit together. So he steps in and says to Congress, hey, I'm going to fix this. See if you idiots can get around to passing legislation. I'm just going to patch it up. See if you can do a permanent fix. And I'd appreciate if you pay me back one of these days. and he basically guilted them into fixing all the national monuments. This was in like the 80s and 90s. And then he's a kid who grows up in Baltimore.

And Baltimore's a city that's having a hard time. He buys the Baltimore Orioles, promises the city that it will not move over the next 20 years. And I think he said, and I'm going to keep the beer and hot dough costs the same for the next 10 years. Not what you think of when you think of as private equity. What personality attributes do you think? made him great as a business person because he sounds like a warm and lovely guy, but he's in PE, which is not particularly a warm and lovely industry. He is really, really good at finding a space that is being ignored by the rest of the market

and not just ignored, but undervalued. So telecom wasn't sexy in the 80s. There was some post-Ragan deregulation, and it kind of got ignored for a while. So, and not just like the big names, but the, you know, the block and tackling or all of the fundamental pieces, just the ability to, it's not even see around corners. It's identify a spot that the markets have missed. Was he prolific in his extracurricular activities in the upswing of the business or is this like a post-wealthy thing? I think they were on parallel tracks. I don't think...

How does one do that? So I just put up Carlisle, by the way, Carlisle, by the way, Carlisle $500 billion, A-U-M. How does someone build one of the most... You know, if they keep plugging away, they'll get there someday.

How does one do that? Like, did you know when he was younger? How on earth do you do all these amazing... No, I did not. I met him, I met someone who worked for him, and I said, hey, tell your boss,

he's stealing my gig at Bloomberg. What's the hell? I've been doing this podcast since 2013. You know, he comes in and Bigfoot's in and takes the video version of it. And I was joking. It got back to him. And I got an email and I said,

once you come on the show, let's talk about your career. So he did. What about the other end of the spectrum? You know, finance and money attracts a lot of other people who will say things that are either, you know, inaccurate or bad advice, you know,

maybe self-interested advice. You know, who do you think has done some damage to the space, put a lot of bad advice out there or a bad philosophy that is, not one that somebody should follow, even if it is popular or visible. So those people don't get the invites to show up on the podcast. I've been having an ongoing fight with Zero Hedge.

Zero Hedge is, is that a blog or is that a community? It's sort of a cross between Reddit and a blog. It's got a lot of contributors. Eventually, they tapped into Bitcoin and to gold, and, you know, that was their, their argument. Listen, there's a Ted Sturgeon quote in the book. Sturgeon was a science

fiction writer in the 50s, and he used to get this question, how come so much of science fiction is not good? And his answer was 90% of everything is crap. And so that's become Sturgeon's law. And so most of the

stuff you see in print, on television, on social media, on substack, most of this stuff isn't worth the time or effort to get it. You know, people send me subscriptions to stuff all the sign. Hey, I sign you up for my substack. You unsubscribe me, block me. I didn't ask you to do that.

Stop sending me your digital shit. And the reason for that is simply this. You know, my mom taught me never take candy from strangers. And that includes research, writing, commentary opinion. Before I read something from somebody who I'm not familiar with, it's a research lift to decide, is this person worth the time, effort, energy? What's their track record? What's their process? Did they just get lucky once? And that's it? Or do they have a defendable approach to this? Have they lived through a few cycles? Have they seen ups and downs? Do they have a good

temperament or every day like Friday where NASDAQ is down 4%. They run around with the hair and fire. This is the big one. It's all over. Like if they have that sort of attitude, I don't have room for them. I think you would probably, guessing you have an opinion, either positive or negative on the, what's his name, the rich dad, poor dad guy. I forgot of his name is.

Oh my God, Kiyosaki. He's been, he's a chapter in the book. And I never read the book. I didn't know anything about him. and my colleague, Ben Carlson, does a post about some of, this is like 10 years ago, about some of his tweets. And they're terrible. Sell, sell equity, sell this, sell that. Like, he is just super bearish the whole 2010s.

And then my favorite tweet of his, which I reference in a chapter in the book on him, was 2018, get out of U.S. housing. U.S. single family home market. The financial crisis was the warning shot, sell housing. And ironically, there has never been a better time in recent history to buy single family homes in the U.S. And when I, someone asked me the question, they said, well, how could he have known the pandemic was going to happen and all these things happening in housing? And that's the point.

That's right. He couldn't have known. What are you telling me? You're defending his shitty forecast by saying he couldn't know the future. That's why you don't make forecasts. You don't know the future. And the takeaway from this is all of Wall Street, all of finance, has a humility problem. And I say this, I have a lot of my biggest mistakes in the book.

I famously passed on or infamously passed on Robin Hood in 2014 at an 80 million. dollar valuation. An app that lets millennials trade for free, that is the dumbest idea I've ever heard in my life. Aside from the fact that it's totally off brand with the indexing thing, millennials don't even have money. If this is, you know, payment for order flow, the dumbest idea I've ever heard. My buddy Howard Linson made $100 million on that investment. And I'm an investor in other things Howard has done.

And I was just like, oh, so stupid. So I'm not just saying everybody is dumb and I'm smart. I'm as dumb as everybody else. But at least I'm kind of aware of it and starting to from the place of we all need a little humility because we don't know what's going to happen. We barely know what's happening today. Our recollection of what happened yesterday is always tinged with a little glow of rosy nostalgia. our expectations for the future is mostly hopes and wishful thinking. Like, the whole human condition requires a little more humbleness in admitting how little we know about what's going on.

Help me a little bit here. I love, like, you have this post that I love. It's called Nobody Knows Anything. And you basically, like, say this one's about SpaceX, but the premise of a lot of your post is like Goldman, whatever, the big shots, they make these predictions. and the truth is, is it's just so hard to forecast. And you said that 90% of information out there is garbage. Right. What's your 10%?

Who can I read right now and get my information from, whether it be news or evergreen stuff, that is the 10% in your opinion? Sure. So I'll give you my list, but the caveat is the process of you figuring out who should be on your list is very helpful, going through the process,

thinking about it, what do I need, what do I need help for? So let me throw out a bunch of names. We want the whole information diet, yeah. And by the way, obviously my whole team is a big part of this. Josh Brown, Michael Batnik, Nick Majy, Ben Carlson, Blair Dukesney, go through the whole list. There's a lot of us writing. So I don't want to just talk about my group. It's a little too self-promotional.

Let me talk about others. So let me start with just broad. economic analysis. It's hard to do better than Ed Yardini. He is very thoughtful, very data-driven. He's been very constructive and bullish during this market. He very constructively said, hey, you know, the U.S. has had a great run. We're starting to see signs of overseas doing better. He's just been a solid, solid guy. He's been doing it for 40 years. He started at Deutsche Bank. really solid. It looks like Ed Yardini's paid, right?

That's not a free one. Yeah, Ed Yardini is paid. If I want to look at market dynamics and structure, that's Sam Rowe. Sam Rowe, you could do the free version, you could do the full version and is a little more expensive. On the behavioral finance side, it's tough to beat Morgan Housel. He just is a great storyteller. Really gives a lot of insight with that.

Real estate is Jonathan Miller. I've been tracking Jonathan for forever. I'm friends with him personally. Here's a guy that really understands what's happening with both residential real estate and the state of prices in the industry. You know, as you go further and further into the weeds, so Jim Chanos for all things short selling, Michael Lewis for all things, Wall Street culture and psychology. He has a new book coming out in the fall on Doge. I'm really looking forward to it.

By the way, Michael Lewis is one of these guys that you think you have an idea of who he is from his books. And then you hear him speak. And he's just hilarious. Dick Thaler is the other one, Richard Thaler of Chicago, on the real hardcore research on behavioral finance. There's so many people. I'm leaving so many people out. Man, I'm shocked autism capital. The Twitter handle hasn't made the list so far.

You know, there's actually some academic research that has found neuro-a-typicals do better at market timing because they are not subject to the same social pressure and emotional trading. Speaking of SpaceX, have you read the story in his biography of Elon's quick foray into finance, his internship? What happened? This is a great story. So he goes, I mean, I'll try to call it off top of my head here, but he, he's in school in Canada. He starts cold calling, like, to get an internship or to get a job. He calls, like, you know, the CEO of some investment bank or some bank out there.

And he goes and he gets a job. And he's supposed to be doing whatever he's doing. But he starts going really deep on, like, some South American oil companies or something like that, something where there was, like, a political issue. and he saw almost like a Buffett-style thing where he's like, look, they've completely mispriced. These assets are mispriced. They're trading at the wrong levels

because even in the worst-case scenario, you're safe. And then there's all the upside of if it actually gets opened up or whatever. He pitches the guy and the guy's like, okay, go find out what we can do. So he calls, he's like, hey, I'm Elon Musk and I would like to place an order or trade. Like, how much volume can I do?

And they were like, you could do whatever you want. And he's like, so I could. buy five million dollars of this right now? They're like, son, you could buy $50 million of this if you want. So he goes back and he tells the CEO, hey, I think we should make this huge trade. And then basically it gets shot down for just like, because they're just risk averse. And he sees that it would have played out well. And he just decides like, this whole thing is stupid. Like, hey, I'm never going to work for other people because I presented a completely logical argument and it got shot down for illogical reasons. And so I just never want to be in that

position again. And also, I should just go build things instead of just do this financial engineering stuff. I should go do actual engineering. And he leaves and he never, never comes back. He was a failed retail stockbroker. Is that what you tell me? There's no financial engineering there. He had no track record. He was a rookie. Why would anyone listen to him? That's, that's the amazing thing. You look back at Warren Buffett in 1967. I think half the people who heard his pitch would like, yeah, why do I want to listen to this guy? I started out as a math and science student at Stony Brook undergraduate. The outgoing department chair, mathematics department chair, was this guy named Jim Simons, leaves to form Renaissance technologies, the most successful hedge fund in all of history.

If you would have met this guy in 1979, you would say, this guy looks homeless. Yeah, I saw him. He looked like he was, he looked like a messy student. he was smoking sigs all the time. He kind of looked like a filthy animal. You would think this guy, I'm like, I'm not giving this guy my money. He's going to smoke it. Sean, what are you pulling up here? You're breaking out the textbook.

I got the story. All right. This is about Latin American debt. Banks had made billions in loans to countries such as Brazil and Mexico. They could not be repaid. The secretary of Nicholas Brady had packaged those debt obligations in something that's Brady Bonds. Yes, exactly.

They were backed by the U.S. government. Must believe they would always be worth at least 50 cents on the dollar, but some were selling as low as 20 cents. He figured that Scotia Bank could make billions if they bought these at a cheap price. So he called the trading desk, and he asked, you know, the stuff I said, he thought to himself, Jackpot, this is a no-lose proposition.

I run and I tell Peter, the CEO about it. The bank ends up rejecting the idea. They said they already had too much Latin American debt. He said, wow, this is insane. Is this how big banks think? He goes, it was a good thing. It gave me a healthy disrespect for the financial industry. And that gave me the audacity to eventually start what became PayPal.

He didn't really start PayPal. He started a competitive product and eventually it was merged to PayPal. But let's not let that get in the way of the story. All right. So he had a good idea. Do you have a lot of enemies? A few? I have no choice.

I can't help it. You just came here spitting fire, man. Someone says something that's bullshit. I can't help. But I know discretion is the better part of valor. But when people are out there saying stuff that is nonsense, that ultimately leads people to lose money. Do you think you ever have to get security?

No. Listen, if someone wants to me dead, I would have been dead a long time ago. That's not a... And who wants to live their life that way? What did he say that makes you think he needs security? From who? Guy Kawasaki?

No, man. No, not that nerd. But I'm just saying that like when you deal with big numbers and you have a big audience and you're dealing with people's money and stuff, I sometimes I think of like the risk reward of just like having someone on, you know, around you when you go to the city. Nobody cares. I got bad news for you. Nobody cares that much about me. I'm not, I'm not that important. And look, here's the reality. I've gotten in the $8 billion. I mean, that is impressive. But it was, I mean, you have a microphone. You have an audience. Yeah. So in the modern world, it's a cacophony of voices. No one voice is dominant. And, and, you know, Elon must bought Twitter.

And so his voice is amplified. When you look at the value he's created over the years, all right, so whatever the PayPal merger ended up being and then Tesla and now SpaceX, he doesn't have to exaggerate. This guy has changed the world, right? Tesla completely changed the automobile industry. SpaceX completely changed a number of industries. aerospace, the concept of getting anything into Earth orbit, satellite. I mean, he's had such a giant impact. You don't need to polish the hagiography.

Your accomplishments speak for themselves. So I have to burnish my crappy undergraduate and graduate career. I don't have that much to brag about from then. And when I see a guy like that, like he didn't found Tesla. He joined Tesla later. His genius was recognizing, oh, no, what you need to do is sell a car that's just miles away from everybody else and don't think like a traditional car company. This is a technology appliance, not an internal combustion engine.

Like, I give him credit for the stuff he's done. That's move the needle. I'm not a fan of the SpaceX IPO, but I sure as hell don't want to. bet against him. He's just proven himself time and time again. You know, he's a tough guy to be on the opposite side of the trade front. Today's podcast is brought to you by my friends at Mercury. They make the world's best banking product. I think you know this already. I use Mercury for all of my businesses. I think I have like maybe seven or eight businesses. We use Mercury as our business banking across all of them. And now they actually just launched a personal banking account. So I have

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Go to mercury.com slash personal and learn more. Mercury is a fintech, not an FDIC insured bank. Banking services are provided through Choice Financial Group and column N. members FDIC. I want to go back to the bragging question. Sure. Because I know you've been doing this forever. I've listened to your podcast and read your blog,

but I still want to know as an entrepreneur the business. So can you give like a short answer to like just some of the numbers about how big the firm is? So the last 80V update we did with the SEC was December 31st. That was $7.6 billion. But when we launched in 2013, that was the start of the third best 15-year run in history. Does that mean like it's a $50 million a year company? We don't, because we're private, we don't disclose our revenue and stuff.

But, you know, we average somewhere around 70 basis points in terms of our fees. When we were a billion dollars, we had like 35 people. The typical billion dollar group at a big bracket firm is two salespeople. a sales assistant and someone helping on portfolio. So that would be four people. We were almost 10x that. So we've always been building as if our growth rate is going to continue. And we've been growing about 30% a year since we launched.

So you said you famously called the housing crisis. And from what I understand, there's an interesting story there. So first, and this is so dumb, my mom was a real estate agent. And so in 03, 0405, we were having all these conversations about how weird the real estate market was. And the normal cycle is come out of a recession, the economy begins to expand. And when I'm looking at all that data pre-financial crisis, nothing lined up with what you typically see. It was very much a backwards real estate-driven economy. In other words, instead of real estate being the beneficiary of an expanding economy,

more hires, better income, it was the opposite. And so anytime you bought a house, you could refinance a few years later at a lower price. And some people were doing home equity lines of credit and taking cash to subsidize their lifestyle. Because in the mid-2000s, middle-class workers hadn't really seen raises above inflation for decades. And so people were spending the equity in their homes. And so I started hunting for some data and for some academic research. And in 2006, Ryan Hart and Rogoff did a white paper that eventually became the book, this time is different 800 years of financial folly.

And the white paper said, when you have a bubble driven by credit, on average, we see real estate dropping 32%. And I use that as a leaping off point to say, all right, I'm too lazy to do all 500 S&P stocks. But let's look at the 30 Dow stocks. And what does a 32% drop in real estate mean to their business, to their revenue? And long story short, I kind of spitball the price of $6,800. How contrarian of a belief was that? All the stuff I had been writing about housing and subprime and derivatives, it was all up on the blog. It was all very public. So, you know, and I spent about a year being the dumbest man on Wall Street, which was kind of fun, all of 07. It's like, you're obviously an idiot. And even the piece that talked about 6800 said, look, the market is in an uptrend. We continue to

see multiple expansion. You don't put on a short. You don't get out of stocks if you're an institutional trader until that trend line breaks and that trend line didn't break for for a solid year and change. So I spent a year being pretty much the dumbest person on Wall Street starting in January, February, March of 08, Cudlow started having me on every week and then twice a week and then it just got to be mayhem because, you know, nobody saw it come. I should say very few people sort coming. I recall being on CNBC with Peter Bookvar, and they literally, when we talked about, you know, the potential downside, and I want to say this was late, 07, they literally, literally laughed at us.

And I remember walking our offices were not that far. And I'm like, either we're really right or we're really wrong, but there's nowhere in between. Do you guys remember the book Snowball about Warren Buffett? Sure, absolutely. I just started reading it. And the very first scene is basically Warren Buffett at the Allen Coe conference, which is the who's who. So it's always like the hottest new kids plus like the old guard in the room together. And at this time, it was all the best.com companies.

And they're all there thinking they're the hot shit. Sort of like how AI companies are now. They think they're the best. And Warren has this famous line. I think he says, only criticize a category, never criticize like a particular name. And I'll compliment particular name. So he tries to be, the point is, he tries to be really polite about it. But he basically says the dot-com thing, it's going to be bad.

And if you look at like car companies in the 1920s, you would have thought that you knowing how cars are going to end, the place to be is in cars right now. We've got to start a car company. But of the 2,000 car companies who launched right when the boom was happening, basically like three still exist and most went out of business. And he basically said, this is what's going to happen with dot-coms. And he tried to do it very respectfully, but it was still very insulting to the audience because they were there.

And I think he even made like a bunch of jokes. He was like, you guys, I think he even said something like, you guys all even have mistresses probably right now. You think you're, you think you're the best. But it's going to come. It's going to come. And it's sort of interesting to figure out inside of someone's head when they see this one bit of data and they make this very contrarian bet. And how even Warren Buffett was like quite nervous about that. He goes, I know I'm going to be right, but if I'm not right soon, then I'm really going to look stupid here.

And I think that's like that behavior of like making that call is actually quite fascinating. There's a famous technical trader from, you know, the 1920s and 19t teens called Richard Wyckoff. And he wrote a book, How I Trade and Invest in Stocks and Bonds. And if you would go back and read that book, everything he talks about, just substitute AI for internet, for telegram and dot coms for railroads, and it could have been written last year. It's over 100 years old, and it's as fresh as nothing ever changes. There's nothing new over the sun. Yeah, the technology is different. But what's the takeaway, which is that like new stuff can get overhyped? Not can get overhyped. Always will get overhyped, which isn't, by the way, a bad thing. That's a feature, not a bug.

There's a great book called Pop, Why Bubbles Are Great for the Economy. And think about it. about the dot com era, think about all of the fiber that was laid, global crossing and metramedia fiber and hundreds and hundreds of millions of dollars, billions of dollars in fiber laid. One point in time, I want to say it was like over $1,000 a mile. The dot com collapse comes, all these companies go belly up, and then the legacy cable companies and the legacy phone companies buy it up for pennies per mile. And because it was so cheap to own at that point, all the things that came afterwards, YouTube, Facebook, Instagram, all of the bandwidth-intensive technology, well, they wouldn't have been viable if it was $1,000 a mile to lay fat pipes.

But for pennies a mile out of bankruptcy. And so I'm not predicting this is going to happen with AI, but it happened with railroads. It happened with televisions. It happened with radio, internet, electronics companies, semiconductors, internet, mobile, cars, go down the list. Every new technology that comes along seems to go through this process. Every new technology is innovative things that are not stuck with all the sunk costs and all the legacy platforms. And so they get to move forward, faster, cheaper, better. So I don't know what, who are the winners in AI are going to be.

But when we look back at it, 20 years from now, look at the computer industry. HP, Gateway, go down the list of companies that had billion-dollar valuations and effectively went down to zero. You could do the same thing with mobile phones. How's that Erickson phone do you have? Are you going to replace it with the new Nokia? Oh, wait, nobody buys that shit anymore. Even Motorola. They're gone because between the iPhone and Android, everything else has been replaced.

It's nice to talk to someone, Barry, who doesn't hold back. I think we thoroughly enjoy that. And, you know, Sean and I have been seeing your stuff pop up for years. We're happy we're able to talk. Appreciate you coming on. Shout out the book. Sure, how not to invest right over there, hardcover paperback. You know, the last book was bailout nation was 15 years ago. And I just, it was a slog. It was tough to write. This book was just a joy. It was so much fun to go back overall. all these conversations I've had and all this research I've done over the years and published one knowing who the hell I was. You're a gem of a guy, man. We appreciate you so much. Well, thanks so much for having me. I really enjoy this sort of stuff. It's what keeps me going every day.

All right. That's it. That's a pod. I feel like I can rule the world. I know I could be what I want to. I put my all in it like no days off. On a road, let's travel, never looking back. All right, let's take a quick break to talk about a podcast. Because if you're listening to this, you like podcasts. And what's better than one podcast? Another podcast, another podcast you should check out. It's called Success Story.

If you like hearing about different success stories and hearing Q&A sessions with successful business leaders or hearing keynote presentations or just checking out conversations about sales and business and marketing tactics, this is a great podcast for you. So check it out wherever you get your podcast.