We Study Billionaires - The Investor’s Podcast Network - TIP463: Investing for Profit and Joy w/ Howard Lindzon

Starting point is 00:00:00 You're listening to TIP. My guest today is Howard Linson. Howard has been everything from a hedge fund manager, an entrepreneur and multiple startups, an angel investor, and a VC. It's not often you get a chance to speak to someone who has been on all sides of the table. In this episode, you will learn why Howard thinks the stock market is rigged, why you should invest in companies you know and love, much like the style of Peter Lynch, Howard's 8 and 80 rule, how to treat investing in business like a game, how to create a network of brilliant people, and why you should cultivate joy in investing. That and a whole lot more.

Starting point is 00:00:33 For as laid back as Howard comes across, his career is anything of the sort. He's accomplished a great deal already, but he's still creating startups and investing at full speed. This is what makes Howard inspirational to me, and I hope you enjoy learning from him as much as I did. So, without further ado, please enjoy this conversation with Howard Linson. You are listening to The Investors Podcast, where we study the financial markets and read the books that influence self-made billionaires. the most. We keep you informed and prepared for the unexpected. Welcome to the Investors podcast. I'm your host, Trey Lockerby, and today I'm super excited to have on the show, Howard Linsen. Welcome to the show, Howard. What's happened? I don't think I've ever interviewed anyone who has been

Starting point is 00:01:26 a hedge fund manager, an entrepreneur, multiple businesses. Some of them have exited an angel investor, a VC. I mean, you've literally sat on all sides of the tape. Of all of those experiences, I'm curious, which role have you enjoyed the most? Thanks for having me on. I think the role that happened most because it happened so infrequently, but you know, I've probably written a couple hundred checks into founders, but just those few that I've known, as soon as I wrote the check, I was going to make a lot of money. Whether the founder believed it or not, you know, I knew enough about the industry or what I wanted to see in the world that the investor was presenting to me, like I knew they were going to be billion-dollar companies.

Starting point is 00:02:08 I think that's, you know, as a non-talented person myself, non-talented operator, sitting across the table and seeing like someone presenting something that you know is going to work is pretty cool. And then seeing it happen, obviously. That's actually really interesting. So is there something maybe a common denominator between these founders that you see? Is it just a certain level of grit or just an energy level of intelligence? What kind of stands out to you the most? So I've had good mentors who have seen the goal line themselves.

Starting point is 00:02:38 You know, I do a lot of sports analogies. But generally it's a founder that has unbelievable, you know, they get the timing right. They get the platform right. The, you know, a few examples are LifeLock, which was an identity theft insurance company, Todd Davis, when he pitched it to me back in 2006, I like, as soon as he pitched it, and it was going to be like a home run idea. And there was all kinds of headaches along the way to a multi-billion dollar company. But just the general kernel of the idea that, you know, was a home run.

Starting point is 00:03:09 Same with Robin Hood. Same with E. Toro. Same with a few that I've passed on, Carter, Twitter. But the ones that I've gone right on and the ones that I should have done all had this very simple product market fit idea. And it was at the right place, at the right time, at the right founder. And that helps a lot. That kind of like impact right at the beginning when all those. forces come together can create some kind of explosion that you can get a lot wrong and still

Starting point is 00:03:39 build a huge company. The day-to-day grind of building it yourself, that's somebody else to it. What a headache. I can relate to that. Yeah, so it sounds like this sort of a Venn diagram where all these things kind of merge and right into the middle. Very interesting. I'm curious on that point, have you ever felt that feeling and then it not work out?

Starting point is 00:03:56 You're like so convinced, hey, this is a sure bet. And then it just didn't pan out either due to timing or something else. Yeah, I mean, there's a couple of TBDs. I say the one that like, there's a lot of deals in the last five, six years that have been screwed up out of a soft bank. They got too much money. You know, they went too fast. You know, you had everything right, except you didn't take your time, right?

Starting point is 00:04:19 Like the art of startups is, you know, the pace. And there's this been this period of the last six, seven years. It's ended, I guess, over the last six months. But finally, for good and for bad. There was this pace of capital that was getting thrown at these ideas that seemed like they were working. But a lot of money thrown at a business that's not quite fully tuned. I have been the ones that I'm like, you know, these guys, like, you know, it reminds you that like too much money can destroy things. So this company that we invested in called Wag, which we were the seed investors out of L.A. as a dog walk.

Starting point is 00:04:57 It's kind of Uber for dog walking. And it was like, no brainer. You know, everybody wants to walk dogs. Families have two working parents, really good founders. Everything was lined up perfectly and it was working very well. And then SoftBank came in and put $600 million in like the third year in business. I'm like, what could go wrong? Well, some businesses just aren't meant to be Uber.

Starting point is 00:05:16 So I would say a lot of my disappointments and they're very limited. Because once an idea is working, it's really hard to screw it up. But we're seeing here in 2022 that too much money can screw up a lot of businesses. Well, I know that one of your operating beliefs is that the stock market is rigged. And I think a lot of market participants these days would agree with you, given all this attention around the Fed, for example. That said, you've had this belief since you were starting out in the markets. I'm curious how the markets were rigged back then and how does it compare to today?

Starting point is 00:05:49 The idea of it being rigged is, you know, in the 90s, when I started it out before Reddit and Twitter and stock twits and the internet for that manner, YouTube and TikTok. Quotes were delayed 20 minutes. Our first go around to Robin Hood and Reddit, there was Yahoo finance and there was E-trade. Imagine like seeing a quote on Yahoo buying the stock and from 20 minutes delayed data. And we were thrilled. We thought, ooh, we are yoloing to the moon.

Starting point is 00:06:18 That was what yolowing to the moon meant in 1998, 1998. And there was no mobile phones, there was no smart phones. We were just dumb idiots. But it just felt like we were close. You know, that's how far away. That's, you know, there were institutions and there were newspapers and then there were the retail idiots like myself on Yahoo finance. So, I mean, come on, the market was rig.

Starting point is 00:06:40 We didn't have the data. Alan Greensman used to come on. They used to have a whole, like, day dedicated to Alan Greenspan where he had pictures of his briefcase and they were trying to figure out what was in his briefcase. Like, it's not even like, you know. Everybody knows everything in real time. Everybody can trade for free. And now the Gen Zir think the market's rigged against that.

Starting point is 00:07:00 Well, let me just explain to people. The market is rigged. And if you invest with that in mind, knowing that you're the last guy to know and that you're paying the highest price, and that'll make your investing. You'll start out with a less of an aggravated mind, meaning, you know, invest accordingly. Like, assume that Warren Buffett and Coleman Sachs know no more than you. assume that no matter how many great tools you have or how good your network is. There's people more in the know and invest a quarter of it because it's really,

Starting point is 00:07:29 because if you get upset about the whole thing, you'll just go down a rabbit hole of like, you'll end up saying the earth is flat and that's not a good rabbit hole to go down to. So much like any kind of sport, the sport of investing requires you to like understand how the playing field is set. And, you know, bringing the fees down to zero, fantastic. Bringing, or close to zero, bringing Twitter and Reddit and stock to its real-time information and social networks, fantastic. But the game is just as hard because everybody has the same tool.

Starting point is 00:08:00 And so, you know, invest according to that. And I think you'll enjoy it more. I love this because, you know, you did mention Buffett there. He's got that quote about if you can't, you know, you're sitting in a poker table. If you can't figure out who the Patsy is in the first five minutes and then you're the Patsy and what you're saying is like, hey, we're the Patsy. We know it. Yeah, I know that you look at investing also like a game.

Starting point is 00:08:22 I'm kind of curious how you would exactly define investing as a game. Is it just simply betting on probabilities? Is there something else to it? And how did you kind of own the patsiness of your investing strategy? Well, you have to own the patsiness. So right there, you got to be able to laugh. You know, CNBC was always my, you got to have an arch enemy. First of all, if you're going to start a business.

Starting point is 00:08:42 It helps to have an enemy made up or real. My enemy was always Wall Street Journal and CNBC. They were easy enemies because they're evil. You know, they call it entertainment, but it's not entertainment. It's misdirection. Everybody has, and this goes to my, you know, everything's rigged. Why are they talking about why they are talking about? Someone produced the show.

Starting point is 00:09:02 Someone whispered in someone's there. This is a good topic. You know, something bubbled up to the top. And then, you know, the machine gets going as is media. And so the game for me was, you know, when I was a kid, we played a game called Risk. It was a flat board game. It was about world domination. And what was great about risk is once you played enough, there was a game, there was some chance, obviously, a roll of the dice.

Starting point is 00:09:26 And the same thing goes in the markets. There's probabilities. And you got to stack the odds in your favor. But how you started the game and where you started the game and how you moved to take over the world was very much like, you know, you could see people's different risk profiles and strategies based on how they played this board game pre-internet pre-a-anything. You sit around for six hours and they spoofed it in and Seinfeld. for a while with Kramer and Newman had this hilarious board game where, you know, they had to have people watching the board. But we would play these games. And depending on where you started, if you started in the middle of Europe, you were doomed because you had to protect all these

Starting point is 00:10:01 borders. Everybody's fighting for Europe. But if you started in Eastern Indonesia, and that's the same thing with startups, if we start doing one thing really, really well and kind of polish it and hone in and build up your armies, then you can move up into India through Siam and then you can kind of spread out that way, and you're protecting less borders. So the whole point of investing a business is, and this is where too much money came into everything, everybody was starting with global domination three, four years ago because of all the money. And Uber was an Airbnb with the examples.

Starting point is 00:10:31 You know, if they had a kernel of growth, you threw a lot of money on it and became, let's go to China, let's go to Europe, let's just win, win, win. And if we flash forward to 2022 and NFTs and crypto, it's back to the art of building a business, which is how small can you be? How small can the team be? How fast can you polish it and then kind of, you know, go out into the world with an idea. There's some sort of art to that. And so that's how I feel like it's a game. And there's many ways to play the game. But with investing, you also have to stack the probabilities, right? You can't just, every trade can't be the same size. Every trade can have

Starting point is 00:11:07 the same risk return profile. But if you're disciplined, you can try and find trades or investments that line up in your favor, like a three to four to one upside. And so if you really are patient, which is hard to do and discipline, you can line up higher probability investment. And that's kind of the only way to get ahead. And then it's constantly like stacking and filling. You know, if you build your own business, still the greatest way to wealth. But if you're trying to become a billionaire just from the stock market, I don't know what book you read or who's lying to you, but that's just not what it is. The stock market is for growing your wealth

Starting point is 00:11:46 and preserving your wealth and compounding your wealth, but in terms of like building your wealth, pre-internet, we were told that like a hedge fund was how you did that, which is why I started a hedge fund. And the reason a hedge fund theory could work is because you're getting paid fees, whether you beat the market or not. So it really was an interesting model,

Starting point is 00:12:04 that a completely unfulfilling way to make a living. But if you're just trying to make money in the market for yourself, very hard to do. And so a lot of people have come into this market recently thinking they can just get rich in the market and we're learning that's just not possible. You mentioned the hedge fund there. I'd like to go there next. You said it's unfulfilling and yet you did it for 18 years. So I'm kind of curious about that experience and how it kind of led to all these others that we're going to talk about. I'm curious about, you know,

Starting point is 00:12:35 taking that mindset of being the Patsy and then going into the hedge fund world. Was that in a way to obviously increase the odds in your face? were you using kind of retail-esque strategies early on and did a change over time? What maybe walk us through the strategy and the thesis for starting the hedge fund? Yeah, well, it was probably closer to like eight years. The fund is still exist because I made a lot of investments in private markets that continue on today. So it's still kind of an entity.

Starting point is 00:13:03 But I was smart enough after eight years to go, I give up. I threw up my hands and I was like, there's no way to beat the market. So in 96, 97, as the internet was just started, a pre-internet, pre-cloud, basically opened a store. You know, there was more, you could be an expert or you could think being an expert because there wasn't that dissemination of information. And so being an entrepreneur around the stock market was starting a hedge fund. You could be a stockbroker and invests like that, or you could start a hedge fund, which was more of an entrepreneur always, like convinced a lot of your wealthy people around you to invest and take a fee. What I learned very quickly was I didn't know what I was doing. I wasn't doing anything wrong.

Starting point is 00:13:45 It was just that, you know, Vanguard came along. And you could realize no matter what you did, it was very hard to beat the market. And so in 2005 is when I started to make some private investment. So the way at work was I knew, and a lot of this goes to War in Buppetoo, you couldn't beat the machine, right? Like Vanguard was this great, simple, you know, disciplined, kind of momentum. you know, market-eating strategy. What really was the market. And once you started competing against that machine, like 2005, I was like, what am I doing?

Starting point is 00:14:19 You may be able to beat it for a while. And the latest version is Kathy Wood. And when I was growing up, it was Gerrude von Wagner and Peter Lynch. There are a few people that do beat it, right? Just like there's a few athletes, like Tom Brady, who defy all the odds. But, you know, it's not a good strategy to bat your head against the wall and think you can beat everybody. And the market, you're competing against globally 24-7-365. There's no like season off. There's no, so the market is like grueling like no other kind of sport or game in that you're

Starting point is 00:14:51 competing against everybody in a multiplayer game 24-7, 365. And then they're constantly throwing twist. Now it's crypto. So now you've got like a whole other asset class that you've got to learn and all the correlations between them. So, you know, forget about it. I've long since said that if you want stock market returns, you know, be in the market and manage your expectations to those market returns. Venture capital became exciting to me because there was no index, right? And it felt like you had an edge because you had some domain experience. And I like the idea that I couldn't see the price of my portfolio every day. And we're seeing that now with crypto. Seeing the price of your portfolio really messes with your mentality because it affects your mood.

Starting point is 00:15:35 and it affects your how much risk you want to take. And it makes you do the wrong things at the wrong time. And so for me, investing in startups 2005 and onward, it allowed me to be better investor because I wasn't worried about the day-to-day and month-to-month fluctuation. You know, every company has these incredible gyrations, whether it's from bad hires or mislaunches. And if you're a public company and you're marking yourself to market every day,

Starting point is 00:16:02 you're going to end up zicking when you should zag, way too many times. And, you know, the private market kind of smooth out those type of mistakes. It's not perfect, but I felt like it truly gave me an edge. And that was when I started doing that full time. Let's take a quick break and hear from today's sponsors.

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Starting point is 00:20:32 I kind of want to start there. So basically, as I understand it, you made an Apple investment very early on that you've held on to. But you came about it in a very Peter Lynch kind of way. I'm wondering if all of your best investments kind of came from that, you know, scuttlebutt approach, if you will. And is that your kind of golf swing, if you will, or I can't think of a better of analogy, but sort of your style that's worked out best? Yeah, Peter Lind, there's been a few books that are. really, even though they're not necessarily stock market books. I don't know a big book reader in

Starting point is 00:21:01 a world of the internet. I never really had the concentration to read books. But Peter Lynch's went up on Wall Street and the tipping point, which was not a stock market book, but it was basically a book about tipping points based on like what happened in Soho and I was a big Soho guy. Like I loved hanging out in Soho and shopping stores in mid-2000s and I was building Wallstreet. And so I really kind of believe that you can immerse yourself in these trends. And first of, I was lucky, you know, at the time that Apple first started launching stores, that was considered a joke, right? There had been gateway stores and Dell stores, and they're continually been flubbed,

Starting point is 00:21:39 like computer hardware at retail. And so it was like, I'd written off before it started that Apple opening Apple stores would be a disaster. And I wasn't even thinking about it as an investment, But where I worked in Phoenix at Camelback and 24th Street, happened to be one of the first Apple stores. It was a high-end neighborhood, office neighborhood. And for whatever reason, and I wasn't even an Apple user. This is 2002 at the time, you know, to run a hedge fund business, you were using Windows. Like, there was no internet software to run your trading programs.

Starting point is 00:22:10 And all the banks were hooked up to like proprietary software. So you didn't use the internet. You didn't use Google Chrome. You didn't use Safari. So I was not an Apple user. obviously. And I went over to the Apple store and the iPod was there and, you know, it was really well done in the way that you could take it. And like, it wasn't like, you didn't have to put it behind a glass that everybody was doing. And, you know, I bought my first Apple product,

Starting point is 00:22:33 which was an iPod and I, you know, I put the earbuds in and I was like, everybody's going to have this, you know, and I just had one of those moments. And it just kept self-reinforcing, the more you saw the white earbuds and the AirPods, you know, the more bullish I became. And the fact does, I was becoming an Apple user for the very first time, even though I was in my 40s. So, it just dawned on me that the market was massive and that the stores, if they could execute, obviously a lot of risk, was going to be a home run. I thought there could be thousands of stores. And here we are today where they've executed beyond all those things. But that was just stumbling, bumbling into Apple. So yes, all my best investments have come from me, kind of Larry David and

Starting point is 00:23:15 Curb Your Enthusiasm, you know, a modern version of like, like Peter Lynch, which is like a little bit more like self-aware, a little bit more anything's possible and a little more like now that I've seen it happen in my life, I'm kind of looking for it for those aha moments where my own experiences interact with trends. It gets harder as you get older because now I'm 56 and I have different interests than a 30 year old, meaning TikTok like I didn't see it because I didn't use it. Tesla, I didn't see it because I wasn't a Tesla customer. So a lot of it is you have, it's much easier if you're the customer and you're in a demographic that is so big that it's like impossible to ignore. So it's very hard to do over and

Starting point is 00:23:59 over again because you get older and the context of which you see trend changes. Let's talk about that demographic that's so big you can't ignore. You have this eight and 80 rule. And originally I thought this to mean, you know, invest in small caps that become large caps, like a 10 bagger, as Lynch would say. But you're actually speaking about, products and markets, walk us through this 8 and 80 rule and how you arrived at it. Yeah, I'm not very good at marketing, but the concept about 10 years ago was that, you know, if you're going to buy growth companies, especially once the internet came along, you want to try and find these markets that have 8-year-olds and 80-year-olds used to go.

Starting point is 00:24:36 In some point, really, it's 2-year-olds and 102 years old. If Google has something for the masses for anybody between 2 and 1002, you see a 2-year-old, 4-year-old with an iPad, they're scroll. going on YouTube. You see an 80-year-old, they got an iPad, and they're using Gmail or their, you know, so Apple and Google really kind of are those 8-80 brands. They're really, you know, 8-to-80 theoretically could be Exxon. Don't get me wrong. A 5-year-old knows what Exxon is and a 100-year-old knows what Exxon is. So you can prepackage. It's not a perfect thing, but I try and find companies that have these massive demographics working in their favor. And that, you know,

Starting point is 00:25:18 just helps. Like, if you're not trying to beat the market, or if you want to be trying to beat the market, try and go with companies that have massive, massive markets, and they're not subject to the same cyclicalities as other people. And so it's just something like a little gimmick that I try and categorize companies that I'm looking at and want to own. And then there's obviously risk management around that. And I have this other term called fasciology, where if you look at today in a world of technology, you know, LVMH is one of the biggest companies in the world. And Nike, you know, are they technology companies or are they fashion companies? So I think as technology continues to permeate everything, I think fashion and technology meld

Starting point is 00:25:59 and some of the, and if not the biggest companies in the world will be companies that do that well. You know, Motorola was a great company, but you weren't going to buy Motorola sunglasses. I mean, they tried. They had partnered with Oakley. And you're not going to buy Apple sunglasses, but you wouldn't buy Louis Vuittaran sunglasses powered by Apple, you know. And so there's all these different meldings that are going to happen now that technology permeate. So we talked about how you held Apple for a very long time. There's this quote that I love about, you know, how did you get wealthy? Well, by selling too early.

Starting point is 00:26:29 And so I kind of bring some mind any positions where you sold too early and watch something run on much farther than you thought. Yeah, pretty much everything. I try not to get mad anymore because my mentors are the same way Fred Wilson, Brad fell. Like, you can't, you know, if you're not running the company and it becomes too much of your portfolio and you know, and you're not managing other people's money. It becomes almost irresponsible for you to have too much in one position. And it happens to me all the time, whether I invests a

Starting point is 00:26:57 little bit in crypto and it becomes a huge part of my portfolio or Robin Hood, which then becomes a huge part of your portfolio and it stresses you out and you're not going to call the CEO every minute because you can't. So, you know, I generally am pretty disciplined about selling Apple, obviously. If I had bought shares every time I sold a little bit to think that I was like diversifying, I'd be a lot wealthier than today. The odds of staying, if I could have predicted the iPhone and services and the AirPods, then, you know, I couldn't. So along the way, you know, risk management, unfortunately, has forced me to sell my winners down.

Starting point is 00:27:34 And those have been mistakes. But, I mean, that is investing. The most important thing for investors to know, because you're not competing against anybody. You know, when you watch an investing show or you're online, you're on FinTwit, everybody's competing. My portfolio is better than yours. I'm making more money than you. I don't even know what that means. Like, you're supposed to invest for the joy of investing

Starting point is 00:27:52 and the art of trying to compound capital. And so everybody has different time horizons. Everybody has different risk profiles. So I think people need to get in the habit of, like, managing to their own risk. And that involves diversification. And you're going to make mistakes. I just have a good ability to move on. Maybe that's not a good ability.

Starting point is 00:28:15 Maybe that's why I'm not a billionaire. but I also have my sanity. And you can sleep well at night. I'm curious how you define risk. You know, say a position has gotten so big in your portfolio, you don't really have a thesis that the company is going to do anything to not keep growing, but it's just a position thing? Is it just the sheer volatility that's coming into play or the potential of loss?

Starting point is 00:28:36 Walk us through how you think through risk. Yeah, there's been a couple recently, and an investor in a fund called Multi-Coin, and they had a big position in Salonah. And it worked in my favor because I couldn't sell. And so for a couple years, I would have, I know if I had owned the position myself, I would have sold so much earlier, you know, for whatever reason, mainly because I didn't understand it. I wasn't a user of the product.

Starting point is 00:29:00 You know, so at some point last year, I couldn't sleep. I was like, what? This is silly. Like, I'm excited. I'm too excited. And I sold enough that would let me feel not like an idiot if it went to zero. I will tell you that that's never enough when it does go down. I'm 90%. Now I feel like I should have sold more. So it just has to be like a consistent being

Starting point is 00:29:21 honest with yourself. And I found that writing every day in journaling helps me stay accountable to how I'm feeling about these things. If I'm too excited, it shows up in my writing. And that's a good time to sell. If I'm too miserable in my writing, it's a reminder, maybe I should be buying something. And so that discipline of writing it down and journaling has really helped me kind of trim. In the end, it's not a perfect thing. You're gardening at the meantime, and sometimes you sell too much, and sometimes you won't sell it enough. I think the art of consistently doing the right thing, but gardening your portfolio, is going to pay dividends. Are you better off at the beginning of this bear market than you were at the beginning of the last bear market?

Starting point is 00:30:01 And that's the game. Like, you stack your chips, you move forward, you know that you're not going to perfectly time getting all your chips off the table. But what can you live with if the market were to change completely the moral? And I think if you asked a lot of people now, you know, like, hey, in March 2, that 20, when everybody's doing SPAC, guilty as charged myself, if you look back and said, listen, and I had these conversations with a lot, a lot of smart investors that were like, I don't want to sell. I want to owe 30% in taxes.

Starting point is 00:30:30 And, you know, if I sell it at 200, it's really like selling it at 140. And I would say, yeah, but you own it at like 10. But, you know, you can only try and talk to people. And now it's at 50 or 40. that $90 spread of where they would have paid tax. So you have to, like when it gets so good that you're not selling for taxes, that's generally a good sign that you should be selling. So there's no perfect rule,

Starting point is 00:30:54 but I think people have to be honest with themselves about how they would feel if the stock did this. And generally, they can't see that. They can't see something dropping 70% for no reason. Well, here we are. And it's happened to like 80% of the tech stocks. And no one can explain why. And guess what they're blaming?

Starting point is 00:31:10 They're blaming Biden and they're blaming the Fed. I'm like, blaming one guy for an 80% drop in your portfolio. That's just crazy. But that's what people do. You know, some people have these very rule-based approaches to selling. They'll have a checklist. They'll say, hey, the missed earnings that they're doing XYZ. And I've just never felt like that was the thing for me or the approach for me.

Starting point is 00:31:33 And what you just described is way more qualitative. Or you can drive yourself insane. But if you think you're a quant, I'll introduce you to a few quant. So you have a lot better chance being the Larry David of investing or the Peter of being a qualitative investor than you do of being a quantitative investor because all the smartest people in the world have gone into quant because it's mathematically based model. And if you think you can be as iron cold as a machine, I'm going to tell you, you're not.

Starting point is 00:32:02 In a world dominated by quants and AI, the edges are still qualitative. I'd like to talk about your experience with Amazon as well, only because, you know, I know you've held that for a long time. That was one of those bulls that was bucking nonstop the entire ride, it would seem, and you've held on for quite a while. What I'm curious about most, I guess, with that, is the optionality you saw early on, meaning they did what you said on the risk board. They were starting in a very specific part of the world.

Starting point is 00:32:28 They weren't boiling the ocean. They were selling books. At what point did you get in and what were you seeing along the way as far as the optionality there? 2006, when I started Wallstrip, I was doing one of my shows. We were talking to a friend, forget his name. It started a music company, like a database company. And we were interviewing about AWS and how it was started by Amazon and they're

Starting point is 00:32:49 powering all these startups. And I'm like, if you sell picks and shovels to startups, that's a good business, especially as Web 2 was going around. And then my daughter was using the Kindle. So it really wasn't about e-commerce when I invested. It was really about AWS. And hearing their name over and over as a startup guy myself, an angel investor. and started stock twits.

Starting point is 00:33:10 We were all hooking everything up to AWS. We didn't have to buy computers. We were just outsourcing all that to the cloud. It was like a no-brainer. Like projecting my business across millions of businesses, I felt like I had inside information. And so really wasn't about e-commerce at all. Never still isn't.

Starting point is 00:33:26 It's still a bit about AWS. And obviously now it's different because people have choices between Azur. They have DigitalOcean. They have Google Cloud. So Amazon, you've got a lot of competition. It's not, you know, now they're a fangstock and everybody loves them. I still own a lot, but it's not like I'm as excited about it as I was in 2008.

Starting point is 00:33:47 2008 felt like the Apple AirPods. It felt like I knew something that everybody was going to know. And I knew it because not that I had inside information, but I was talking to hundreds of startups that were all hooking up to AWS. And everybody was talking about Amazon as a bookseller. Let's take a quick break and hear from today's sponsors. No, it's not your imagination. risk and regulation are ramping up, and customers now expect proof of security just to do business. That's why VANTA is a game changer. VANTA automates your compliance process and brings compliance,

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Starting point is 00:37:20 This is a paid advertisement. All right. Back to the show. Another company where I feel like you knew something other people didn't. When investing in private companies like Robin Hood way before people even know what it is, what it was, what were you seeing there that others weren't? For the aggravation of trading and all the headaches from like the last cycle, no kids were building an e-trade 2.9.

Starting point is 00:37:45 So it really wasn't until 2013 that I got shown Robin that I was up in the valley and they had pitched me, they had called me because I had stock twits. It wouldn't be interesting if you could buy the shares, click a button on Twitter, and the link would go right to your brokerage account, and you could buy shares, and then reshare the trade. The social trading. That was like a 07-08 idea that I wrote about. And when I saw Robin Hood, I was like, finally, it was like a no-brainer to me to do it. I didn't know it would be worth multi-billion, obviously the first investor, but I knew that if they build it, they will come. And it wasn't about thinking through the business plan or how they're going to make money. It was an $8 million value. It was just yes or no. And they delivered on that basic premise, and that's why it was a no braver. And I was right. Like, I mean, in the end, I was, I was right. People like to think they can beat the market.

Starting point is 00:38:36 And Robin Hood provided an on-ramp to tens of millions of people to do it. I'd like to talk about Howard, the entrepreneur. And I'm going to stick with this kind of Larry David or like Forrest Gumpi and kind of a framework. But I know you're way too smart for that, but we're going to play along. Larry David's really smart. That's true. Larry David is very smart. Okay, so we're going to stick with the Larry David metaphor here for a minute because it seems

Starting point is 00:39:00 like you kind of stumbled upon stock tweets to a degree. You're on Twitter. You use the dollar sign next to a ticker. What happens next? So when Jack and Ev, like I said, I was, when YouTube came out and my mind was blunt. So I'm a hedge fund guy in 2006. I hate my life. I'm trading.

Starting point is 00:39:19 I'm not going to win. I'm thinking about what I'm going to do next. and yelling at the TV, like everybody who watches CNBC does, they yell at the TV. But you're in a room by yourself. You're literally going insane. And then YouTube came out and I was like, oh, my God, this is the future. And I'm going to create, like, everybody could create their own CMBC. You know, that was my vision.

Starting point is 00:39:40 And at the time, no one will remember this, but in 2006, when YouTube came out, everything was cat videos. People would just put a camera on their cat and take a picture of their cat doing silly things for hours. And that's what people use YouTube for at the beginning. So there are two things they used it for, women filming cats and people filming TV shows and putting them on the internet or whatever they were going to do. And the media companies do what the media company is doing. We were left with cat videos. That's what led me to start Wallstruck.

Starting point is 00:40:05 Anyway, sell Wallstrip, go to CBS. Twitter comes out. And I'm like, that really is the future of trading. And so I dropped over there. I quit CBS. And I went to Jack and Ave at Twitter. I said, why don't you guys do Twitter of finance? You know, Twitter.finance.com.

Starting point is 00:40:23 And they were like, what? We have an open API. You should just build it. And I remember, you know, back then we had BlackBerrys. We didn't even have iPhones. I remember Fred Wilson was a friend of mine. And I tweeted him on my BlackBerry. I was like, ooh, you know, what do you think of this?

Starting point is 00:40:38 You know, I bought Apple, you know, dollar sign AAPL. And Fred wrote back a message saying genius. And if Fred writes you back a message saying genius, you know, you're on your way. And I really didn't want to start a company. You know, I was 44. But Twitter didn't want to do it. And so I started Stock Twitch, which was just Twitter for Stock. And here we are 12 years later.

Starting point is 00:41:02 It's got about a million daily active users. It's a profitable business. It's a great little business. And it's really just Twitter for stocks. It's just for people who want to talk about stocks. And we came up with the dollar sign as a way to at the beginning. Like if you're, you know, if I'm searching for Apple and I go hashtag, Apple. It's like, oh, I bought a green apple versus, you know, people in stocks talk about it in this

Starting point is 00:41:23 domain experience. For me, I knew, I spoke in tickers. Like, I don't know, I'm demented. That's how I saw the world. G-O-O-G, BlackBerry was R-I-M, you know, Citibank was C. So the dollar sign was our way of making sure Twitter, we could separate who was talking about stocks versus something else. So that's really, it was just a hack idea that we did. That kind of raises this question. I mean, Twitter's been in the news a lot lately. They can't seem to make money. I'm curious if the business model with stock twits is a bit different. Is there anything Twitter could learn from stock twits about how to make a buck? Well, they have a lot of cash flow. They also have about 4,000 too many employees. I've

Starting point is 00:42:06 been giving out free advice to Twitter on Twitter for about 12 years. No one's listening. Listen, they made a decision early on to raise bucket loads of cash. When you raise bucket loads of cash, you then have different pressures than you do. I have a few. I've a few things. I've you do it yourself. And they had hundreds and millions and billions in the bank. And it came time to make revenue. And training is a very small business. You know, even Robin Hood has proved that it's very hard to make money. But Twitter should be free for everybody, not even ads. And if they monetize, you know, trading and betting and data from real time, from the people that want to pay for the data, they will pay the most. So in the right world, Twitter is a pipe. And they should charge

Starting point is 00:42:47 J.P. Morgan, Goldman Sachs, Reuters, hedge funds, Bloomberg, billions of dollars a year, and let every company sit from the fire hose and charge accordingly. Then they would have this great utility business. But when you raise billions of dollars, it's very hard to tell your DCs, hey, we're not going to hire any employees and here's our business model. And so it was just like early mistakes around raising money and expectations that set them on this path. It's a disaster. I mean, one of the greatest products of all time may be the best. And it's not used by hundreds of millions. It's used by a few hundred million people.

Starting point is 00:43:21 It's not YouTube. If Twitter had done the same thing and just focused on Bloomberg, the company would be worth $150 billion without selling ads. And they didn't know that business. So they didn't see that view. And I'll tell you who's breathing the biggest side of the leaf is Michael Bloomberg, because Twitter could have destroyed him. And instead, he let Bloomberg sip from that fire hose insert it into the terminal.

Starting point is 00:43:46 And now all those hedge fund guys get Twitter. Let's talk about some of the pros and cons, the balcony and basement of VC, because you kind of mentioned earlier, illiquidity can be somewhat of a blessing. It's kind of like leverage, though. It can cut both ways. And I'm kind of curious about the name of the fund, actually, is called social leverage. What is the difference between social leverage and financial leverage? How would you define the two? Social leverage is about using your network.

Starting point is 00:44:13 Obviously, the risk of social leverage is time because you can get so many things done. You have too many projects, and that's a lot less dangerous than financial leverage. So you may have some more unfulfilled relationships from all this social leverage, and you may spread yourself too thin from all this social leverage, but you're not taking down the whole economy. What takes down the economy and what takes down industry is financial leverage. Let's talk about relationships. You just brought that up.

Starting point is 00:44:39 Over the years, you've built this unbelievable network of brilliant investors and business people, entrepreneurs. Who are some of the people that stand out to you that have made the greatest impact on the way you think? There's Roger Arenbergh is a great investor. Bradfeld. They all kind of came up together. Some people that these people understood tech. They had been through a crash.

Starting point is 00:45:00 They'd seen winners before, right? They'd experience defeat. I mean, that's who you want to be mentored by. You don't want to be mentored by someone who's only seen. victory. It was the right time with the right mentors on the right platform. You could have just shown up in 2007, 2008, 2009. As long as you didn't blow up, you're going to get rich. And that's where we are. And now a lot of people just think they're smart. But like, when you have that many platforms launching at the same time, forget about it. Are you finding people that really

Starting point is 00:45:30 change your way of thinking? Or do you kind of look at and say, I respect that, but, you know, I view it differently? So I really look to comedians and the comedian community is coming back together and getting a handle on the woke community and the right, and they're getting a handle on how to manage phones as you come into a club. And they're starting to push back against, like, the cancel culture. And when they start pushing back, when you have people that are that smart and that creative, finally just pushing back, we need more George Carlin. Like, we need more Ricky Jervais. They may be rich and they may be affected, but they really have a way with their words of defining moments in time, I think that whole area is very important to me because it's a

Starting point is 00:46:10 very strong community. You mentioned joy earlier, and I know you've thrown this into some of your projects, investing for profit and joy, and the joy really popped out at me. I mean, it seems obvious when you just kind of gloss over it or read it. You say, yeah, you want to make money and be happy. But that word in particular is such a choice word. It's kind of interesting. It's not happiness.

Starting point is 00:46:30 It's joy, right? And so I'm kind of curious over your career, which part of investing has brought you the most joy. For example, Warren Buffett says he tap dances to work. He doesn't need any more money, so it's not really that. Is there something in the process or is it the idea that has come to fruition? What gives you the most joy when you're investing? You know, when I was young in the 80s, if you were like, and I grew up Jewish, like Jewish community, you got to be a lawyer-doctor account.

Starting point is 00:46:57 Not a lot of pressure. That means you got to do school. You got to go to graduate school and you got to go build. by the hour. That just was not appealing to me. Today, that's truly what AI is disrupting. Everybody says, tech's coming for my jobs. Text coming for lawyers, doctors, and account. Right? Like, there's three paragraphs you need in a contract, right? And that smart contracts will start taking care of that. Doctors, let's be honest. No one trusts their doctor. We didn't trust Dr. Fauci. Now, I'm not saying good doctors aren't good, but like we're open to new ideas. And then accountants,

Starting point is 00:47:27 I mean, everything's cash-based account. Like, you know, we've already blown up the idea of of what accounting is because everybody can work for themselves and figure out how to be cash flow positive. So in a world like that, people can actually pursue their passion. In a world of TikTok and YouTube and Twitter, so for example, my kids are not a lawyer, doctor account. My daughter's living in New York as an entrepreneur. My son's living a golf life. And 30 years ago, that wasn't a choice for any kid. And so that's joy. Like kids, they have other kinds of stress and they have other kinds of, I mean, say depression, but anxiety that the phone brings and all these things, but that's just, that comes with the territory. But with the smartphone and with the cloud

Starting point is 00:48:09 and with the internet, comes these unbelievable ways for people at a much younger age to find their calling and to do stuff they love. They'll still screw it up and they'll still make mistakes. But the fact that it took me till my 40s to figure out my calling, if we can help people speed that up and do it in their late 20s, that would be. do an incredible amount for both behavioral good of the world and just wealth, because that extra 15 years of the grind, if we can get that out of people, is an important kind of message of what I'm trying to do is like, and I'm trying to lead by example. A lot of people that read me just go, oh, I want to live your life. And I'm like, well, if you're going to live it, try and do

Starting point is 00:48:49 it in your early 30s. Don't wait until you're 50 like me. Because I think it's possible. You know, happiness is a weird word. So the only joy we're going to get is that. when we're not doing those three things, which is our work life. And if we hate our work life, we're screwed. So being able to find what you like doing has been a gift and like showing other people the way is really fun. Okay. I have a bonus question for you as well here. So, you know, you mentioned NFTs and you're leaning into that world of Web3 moving forward. And I am in my early 30s and and I feel like I'm one of those people that was excited about it to a degree and then I kept looking into it following it and I was like I just can't find a use case for this and

Starting point is 00:49:34 there's this clip going around with Andres and kind of fumbling his way through a elevator pitch on web three and I guess you know I've just been around it a long time and I'm struggling here I'm struggling for the use case can you walk me through or give me a proper one yeah it's not going to make people happy but I'm very I feel like finally have an idea of what it is And that's the problem. If I can't explain it, I'm supposed to be an expert, and I admit that I don't know it, how can you invest in it? This goes to all the money that was going around, right?

Starting point is 00:50:03 Everybody's looking for a new platform, right? If you had started, when Google Glass came out like 2012, like they bury those magazines of market entries and et cetera. These are very smart people. I know these people, they have best with me, the top of the food chain in terms of what they read and how they think, but they're wrong, just like everybody else. And when they're wrong, they're really wrong. So if you remember, there was Google Glass.

Starting point is 00:50:26 Everybody was going to wear glasses. And that was going to be your search engine, blah, blah, blah, and Nirvana. And if you had started, and Andreessen did, if you'd started a Google Glass fund in 2012, let me tell you, there's a lot of donuts in that fund. Okay. So Web 3 feels like Google Glass in that. It's just the web. And people have built it into being, like, who's going to benefit from Web 3?

Starting point is 00:50:49 Google, Apple. You know, why is Warren Buffett by Apple? Why does he think Bitcoin is silly? I mean, he's soundbiting, but if he really believed it was stupid, he wouldn't have 42% of his money in Apple. Basically what Warren Buffett's saying is if Web 3 something, Apple will be part of it, right? And it's smart because he's hedged. You know, five years from now saying he's not going to miss the crypto chain because Apple's going to have a wallet. Because this whole thing won't work.

Starting point is 00:51:16 You and I don't get it because it needs to work with Apple wallet. And by the way, we need to be able to pay for an NFT with Apple Pay. Like, I shouldn't have to go and do Ethereum. So technology and all its wisdom has complicated this whole thing, which is a feature, which is a beautiful feature. The whole point of Web3 is for it to be complicated so that people, it's not for everybody. But then the VCs came in there and said, we're going to make this for everybody. Well, 10 years later, it's for nobody except crazy people.

Starting point is 00:51:46 So the way I think Web 3 is, is it just augments Web 2. If you have a Shopify page and you have a great little store, there should be an easier way to build community around your product. And that's where NFT is coming. But an NFT is not really going to work if your 60-year-old cousins got to download a metamask and then transfer 60 bucks into Ethereum and pay $100 for that transaction. No offense to the crypto people, but that's just mathematically dumb and like eight steps too many when they have an iPhone in their hand. So I think we're going backwards. And I think the way to think about NFTs is the opposite of Web 2.0. So in Web 2.0, the two hottest companies were Groupon and like a class pass.

Starting point is 00:52:32 And the whole idea of Groupon would like take the whole internet and turn it onto your sandwich store. And Frank, the sandwich guy, could go pay Groupon and have a million people show up on his door at the same time. Let me tell you what happened. It happened. And then Frank went out of business because he got all the dregs of society. coming for their cheap one-time sandwich. That was the Web 2.0 version of NFTs, Groupon, and ClassPass, and Flash sales, was magnificent.

Starting point is 00:53:00 From an entrepreneur's perspective, I can channel everybody on the Internet and make them go to one place at the same time. Unbelievable. Web 3 is the opposite. If I could send you the best people at the right time with the right way to enter the club with my NFT, and there were rewards built into that so that the right people are using your product and they can form community around that, that's Web 3. What everybody's got wrong is they think it's the same as Web 2.

Starting point is 00:53:27 And Web 2 is about traffic. Web 3 is much more about the right traffic. And so I think it's more of an extra feature of the web. And that's why we're having, like, no one's having that real discussion, but like Groupon was a very Web 2.0 thing. And that didn't work. I mean, it worked for the founders of Groupon. But it needs to work for the Frank Sandwich Shop.

Starting point is 00:53:51 And I think Frank Sandwich Shop needs this to work with Apple Pay. And it needs to be able to give out a card that nobody loses for loyalty that's just an NFT. And that NFT can do many more things for that customer, right? And the more information you plug into your NFT, the more information that you could help your customer when they come in the door. So I don't think it's as big as what everybody says. But at the same time, the companies that are going to now build using NFT,

Starting point is 00:54:17 are going to be better. And I think Apple and Google are probably the biggest beneficiaries of it. What I think you're saying there is that Web3 will alter Web 2, not necessarily change it. So, Howard, this has been so much fun. Thank you so much for taking the time. I've really enjoyed it. Like I said at the top, I'm so impressed with everything you've done. And it takes a certain, I don't know, flexibility, elasticity, something that to kind of keep your mind as open as you have to play all these different roles and to fit into all these different scenarios and or opportunities. So a lot to learn from. Thank you for putting out a lot of content on it as well. I highly recommend people check it out. Before I let you go, please hand off to the audience where they can learn

Starting point is 00:54:54 more about you, find your podcast, find your research, anything else you want to share. Yeah, three things. Thank you. Howardlinson.com, my name, just search it. I write pretty much every day. It's about the markets, my trends, my prostate, my family. And then Twitter is generally the silly dissident Howard, which is can I get kicked off? the internet. I'm trying to, you know, it's a fine line between getting kicked off and not. So, you know, it's definitely a more edgy part of me. And then my podcast is just lean back with my buddy Canute. We've done, I don't know, 300 episodes called Panic with Friends. You can search it on Spotify or Apple. And I sit down with like my favorite entrepreneurs, the people I look up to.

Starting point is 00:55:38 And I don't ask them, you've run a professional interview. I literally do not run a professional interview. It's a mix between how Conan and Brian, like he talks about himself all the time. I kind of do that. It's hard to get me to shut up. But it's really just a wacky look into how I think about things and trends. And that's one a week

Starting point is 00:55:57 called Panicap of Friends. Fantastic. Howard, thank you so much again. Let's do it again. Thank you. Great to meet you. All right, everybody. That's all we had for you this week. If you're loving the show, don't forget to follow us on your favorite podcast app and maybe even leave us a review if you'd be so kind. You can always reach out

Starting point is 00:56:13 with feedback or questions. I'm on Twitter at Trey Lockerby. And if you're looking to up your investment game, be sure to check out the investorspodcast.com or simply Google TIP Finance to find all the resources we've provided for you there. And with that, we'll see you again next time. Thank you for listening to TIP. Make sure to subscribe to Millennial Investing by the Investors Podcast Network and learn how to achieve financial independence. To access our show notes, transcripts or courses, go to the Investors Podcast.com. This show is for entertainment purposes only. Before making any decision consult a professional, this show is copyrighted by the Investors Podcast Network. Written permission must be granted before syndication or rebroadcasting.

We Study Billionaires - The Investor’s Podcast Network - TIP463: Investing for Profit and Joy w/ Howard Lindzon

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