Howard Lindzon of Stocktwits and Social Leverage
Transcript of a Tacos & Tech podcast episode (host Neal Bloom) featuring Howard Lindzon, General Partner at Social Leverage and CEO of StockTwits. The conversation covers Lindzon's journey from finance to tech and media, the emergence of Web2 and social finance (including the origin of the cashtag), founding StockTwits, reflections on startup economics and investor behavior, and promotion of the Stocktoberfest event in Coronado. The tone is conversational, anecdotal, and reflective, with local San Diego color (tacos, Coronado) woven throughout.
Because if you give someone like Chamath the balance sheet, that'll make it say whatever it wants or. Or Bernie Madoff or whatever, right? So. So. So it's also the most dangerous tool in the world, right? So I don't trust them. I know that they work, but I don't trust them because I assume someone's just going to put in the wrong number and make it say what it wants to say. Right? It's almost like art.
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To the Tacos and Tech podcast where we interview tech leaders in the San Diego tech ecosystem. We also read the latest tech news on this Week in San Diego Tech news. Follow us and subscribe online to your favorite podcast network. Hello and welcome back to the Tacos and Tech Podcast with your host, Neil Blum. Here I am so fortunate to have on a longtime friend here in the San Diego community, Mr. Howard Lindsin, General Partner of Social Leverage and CEO of StockTwits. Hey, Howard. Good to have you on.
Check, check. Not kidding. Yeah. Hey, buddy. Tech idiots.
Yep. Yep.
What are we doing here? Talking to microphones. But when you're here in Coronado and I'm in Del Mar area, but this is how we do it sometimes.
That's the beach.
Yeah.
The porch office is open for another few. Another few months. How's. How's your summer been?
I tell you what, Nip is gonna pay taxes. I don't mind paying taxes. I definitely would mind paying taxes if I was inland California. But if you're going to pay taxes in the free world, Coronado is where you were underpaying. I'm very lucky. Coronado's special place.
It's a very special place for sure.
It's not for everybody. I don't get it. But that's cool. But it's the only place. It's definitely. I feel like it's my, like my best self here.
Yeah.
Oh, I love to hear that. What's funny is that, you know, I'm every day somewhere in the San Diego community except I'm not in Coronado a lot. Except when you're in town I feel like it's like Howard's domain but otherwise.
Feels like you have to invite people. It feels like. But when they come, they're always happy they came because the bridge is I guess intimidating. But it's so silly. It's a piece of, piece of modern art that you get to drive over and you know in the world of Google Glass and iPhones you should. It's something to appreciate. It's a magnificent structure. It's at a time when they had told you they paid it off very quickly as a tool. It's a real gift to have a place in America that feels that safe but yet that you don't know why because you don't see the military. And it's, it's all the best thing about, you know, being conservative, which I am, even though people call me a libtard. It's because it's just like, okay, like the war's the war. Like if there's. You respect the military.
Yeah.
Not some great job. Like it's just, you know what I mean? So I think like having that kind of perspective, raising kids here is just like a special place.
Yeah.
We're going to talk about how you found it because it is a special place and it is hosting a special event, Stocktoberfest this October, which we'll get to in a second. But you have a long history both in finance and in tech and I don't know actually when they blurred and blended together. Can we take it back a little bit? Like when did you, when did you first. Getting kind of more.
Yeah, I mean I, I still don't think I'm in finance. I don't look at balance sheets. My wife's a bankruptcy attorney and I'm very poo poo on finance because to be honest, like so when I was a kid for Excel, like people don't realize there was pencils and you would take, you would Take my stupid note. But like you know I would know that you had to take to do books back in the day for a company you had to take paper together to just do ledgers. You know what I mean? There was no Excel, there was no before Excel, Lotus 1, 2, 3. But. And I hate account. I don't understand accounting. Like I don't understand. You put a number here and it goes over on the other side. That just means that someone can cheat. Like when you're making up numbers on two sides of a letter. So it's like cash accounting makes sense to me. How much cash do I have? What's my spend? Which is what made Web2 so interesting. It was just cash based invest and you have your money to spend and you better do more profits revenue. It wasn't a balance sheet business. You know pre the Internet it was everything was a leveraged balance sheet business. So you had to take paper together and, and how can you do acquisitions? There's no Excel, there's no, there's no models. And Excel came out and I'm like as great as that was for the world, like probably the most under other than maps, probably the most undervalued one product of all time. Because everybody think about public companies and think about the, the capitalism and acquisitions and what we all benefit from today is fucking Excel spreadsheets. But at the same time I totally distrust them because if you give someone like Chamath the balance sheet, that doesn't make it say whatever it wants or, or Bernie Madoff or whatever. Right? So. So, so it's also the most dangerous tool in the world. Right. So I don't trust them. I know that they work, but I don't trust them because I assume someone's just going to put in the wrong number and make it say what it wants to say. Right. It's almost like art. So it's just become a financial art project. So I'm not a finance gu. There you go.
Okay.
That's what people like to say because I did a hedge fund and I, I was educated in finance MBA and, and, etc but so the stock market started make sense to me because it was more like an art project. You had price, you had volume. You could study patterns of great companies and it really has never no fundamentals matter. But it, if you really think about it, they don't great companies and great products and supply and demand and if you watch the markets long enough as I have like very little makes sense. Once or twice a year the markets make sense and in between all that, it's chaos as everybody aligns their positions. Kind of like a football game for those one or two days a year where everything kind of, oh yeah, that's worth that. But in between, it's a scrimmage. And so not finance, but like money and, and behavior and then not tech, because I could barely make this podcast today with the sound like I get nervous as soon as something doesn't work. So. But it was that meld of financial world in toys and consumer and investing and Web two came along and I was a little old, but web two came along and the Internet started making sense to me. You could plug things in, you had YouTube, you had Twitter, you could talk, you could write, you could find your doppelgangers, use network. And that's where social leverage came about. So it's just like participating in finance by like using Yahoo Finance Excel. Knowing what I liked, what I didn't like, seeing the incumbents build products. And then web two came along and everything kind of made sense to me.
But along the way, not only making sense to you, I think you've always had this sense to also talk about it and broadcast about it too from, I know, from wall strip days. I don't know if you had even before then. Like, it's one thing to ingest it, understand it and do something about it, but you actually te and mentor and bring and. And you have a famous quote about being a pilot fish alongside a shark like that. That doesn't necessarily come hand in hand with money. Finance, technology as well too. So why the media angle with all of it for you too?
No media.
Right.
Like in Toronto in the 70s where I grew up, it's kind of like Stanford for the web era for engineers. If you were in the seventies in Jewish Bunny or Weird, the club. Comedy clubs were where weird kids went. There was no coffee shops, no sushi. It was just like, you know, comedy was like a, A weird owl place for. And. And you also had Second City and you had. Which is, you know, Second City Toronto, which is better than the Chicago version. John Candy, Eugene Levy. And then you had Jim Carrey and Mike Myers doing stand up and they were coming of age, so it was like the thing. And so, so, so my friends thought it was funny and I went and did open mic nights and you know, 15, 16 years old. It wasn't good, but good enough to at least survive, you know, in not making money, but just go hang out with comedians and really, really traumatizing type experience, you know, because. But it shaped kind of who I was. Like, I always had this gift for like hanging out with comics, but I just didn't have this thick skin or there's just no experience in life to tell stories like I can do now because I'm a storyteller, not a joke teller. So. And the real skill that I developed back then was because it was, you know, bombing was not fun, was writing jokes for other people, like just listening other. If you're at the clubs all day, you're just like, if you change that. So I wasn't a writer, but I was a good, had a good ear for, for rhythm and so I could fix other people's stuff. Yeah. I was loved amongst the comedians for just fixing things for them.
Yeah.
And I was such a fan of common. But, you know, I went to college because, you know, you're Jewish and you have to go to college and back then you, you had to be a lawyer, doctor, accountant. In the 80s there was no Internet. There was, you were a professional. Your parents came for the Holocaust or the grandparents came from the Holocaust and you're going to be a lawyer, doctor, accountant. And that was not for me. So I moved to Arizona and just kind of became an entrepreneur. Luckily, at a time when being an entrepreneur was. Being an entrepreneur before, the Internet was not, not a cool thing because it was a slog. But being in the. You had Excel and the, and the Internet, being an entrepreneur, you'd be stupid not to be an entrepreneur. So we've got, we went from. It'd be stupid to be an entrepreneur because what did an entrepreneur mean pre Excel? Pre Internet meant opening stores, doing inventory. It was hard cost of goods sold payables, receivables. A million things could go wrong.
Yeah.
And then, then you compare that today with the cloud and AI and whenever it's like you'd be stupid not to start a business. Doesn't mean you should, but I would just say you'd be stupid not to start a business. Would be stupid being a lawyer, a doctor and a camera.
Yeah.
Especially in the AI.
That, that's a big switch in 40 years.
Yeah, totally be interesting what we are going to be telling our kids what they should do when they grow up.
But why do we have kids? We'll just birth robots.
True.
Have a kid. No, I mean, I don't know. I don't know. It's too hard to predict based on what I just explained about, you know.
Yeah, yeah.
It's too hard to, to predict that far ahead. It's part of investing. It's like how far ahead do you. Of the world do you want to be? Do you want to be? You can almost be behind. Like, being far ahead is. Is. Is probably stupid.
Yeah.
You chart one path and you say you're headed here for 10 years and you can completely in the wrong direction.
For sure.
Yeah. As. As a. As a successful seed investor, I guess I would say that reaching too far into the future is a bad idea.
Interesting.
Yeah. Yeah.
So we're already on topic. What We're.
Yeah, it's okay. That's. We're. We're talking your financial journey and where that manage. Melded into media and tech. When you were in Arizona and then eventually San Diego, which I want to hear those stories. Was there a community for people like you? Like entrepreneurs Interested in Web 2.0 or anything like that at all, or how'd you find people?
Definitely not Arizona. It's just like I said, webg. I started writing a Google blog because I had. I had Google Blogger was a great product that was ebbs. Sold it to Google. That was the original OG blogging platform. I guess GeoCities. But I wasn't. Maybe back then you didn't have a live journal, so. No, okay. No, no, no. I was just a straight entrepreneur and didn't have time for that, kids. You know what I mean? Like, it wasn't like something I thought about. I not. I wasn't into comedy. I was into trading stocks and like making a living. And. And to be honest, before the Internet, like, hedge fund was like the closest thing to being like an entrepreneur. You survived based on the profits. You made really a dumb business, but it was an entrepreneurial business, which is what I started. It's like, okay, if people trust me with their money, I'll make more money. Back then, you didn't have to compete against the S P. Like it wasn't like a thing. Right. That came. And that really is why I quit being a hedge fund manager, because I quickly realized it's pretty good way to invest and I'm ripping people off. Like most people are ripping people off with the hedge fund. So this is like 2004, 2005, but in the 90s, like, being a hedge fund was like the frontier kind of entrepreneurship. You survived if you did well.
Yeah. You took risks and you're rewarded.
Yeah. You got to use other people's money and anything went and you realize everybody's cheating. But that's what it was. Wild west, right? You give me your money, I'll give you back more money and I'll take 2 and 20, that's pretty good business. And by the way, it's evolved to being an angel investor right now. Right. So less ability to cheat. That's what I think people are mistaken by. Like hedge fund was truly unique in that it was all kinds of characters because just anything went theoretically. But they, in the seed adventure world, things aren't liquid. So you can, you can cheat, but like I don't know who you cheated. Right, right. Like cheating yourself.
Yeah.
And it's, you know, it's a liquid. So it's, it's evolved in that way. But anyway, so no community in Phoenix. I was a Yahoo Finance guy and, and what was fascinating about Yahoo Finance was we thought you use Yahoo Finance just as popular as ever. People have workflows that get stuck in. But we thought we, as someone who didn't have money for a Bloomberg or whatever, you know, what's just a street kid for trading. When Yahoo Finance came out like that was like our Twitter. We were like, oh my God, I could talk to like crazy people on the Internet, look at price quotes, but it was 20 minutes delayed. Think about that. So 1998, 1999, during the first Internet boom, you were 80% of retail investors were on. Yahoo Finance was still small retail. Right. Like it was E trade. It was growing, but it was small. So we were all using the same product, kind of like stuck to its Twitter Reddit today, but it's 20 minutes delay. And we thought that was like we got the man. We literally thought we had an edge with 20 minutes delayed data. Think about how dumb that sounds now. Okay. Yeah, think about how dumb sounds trying to beat the market with real time information which everybody now has dumb. Okay, so that is what we thought edge was. So you can imagine how well I did. Everybody did well for a couple years because everything was going up. Yeah, it's kind of like the same version of Web two but on Web one.
Right.
Everybody thought there was a genius because you had Yahoo Finance and stock market was going up. This bull market ended when everybody worked at Facebook and Twitter and YouTube who thought they were smart, but they didn't. Well, I'm sure most of them are smart because they, they, they work there, but they didn't do anything. The, the products did everything. The free, the zer did everything. The cloud did everything. Apple's iPhone and Android did everything that was like organic. Now we get into like, okay, now who's going to be an entrepreneur now that those things are not organic anymore? But so, so Yahoo Finance was an organic way to enter the market, you were going to get killed because you're 20 minutes delay. Then web two was like, you took 20 minutes delayed, it went to zero. That is like as an investor and a financial person and as someone who's into tech, I'm like, okay, if you thought 20 minutes was a good thing, how about like being ahead of the market? How about if you know how to use Twitter and stock Twitch and Reddit, you actually could be 10 minutes ahead of Bloomberg.
Yeah.
Because they don't even know how to use those things yet. They weren't even adopting them.
Right.
So that we went from like. So it was like a license to print money. I didn't, I couldn't quantify that to people. So it's like if I called people and explained my edge, they would have said, you're insane. You know what I'm saying? So it was like such a hidden edge. I couldn't even prove it. But it was like everything I did was working.
Yeah.
And it was like I had this magic trick that I can't even believe the investments that I was making from someone with very little experience. So. So I look back on that 2006, the minute YouTube and, and Twitter and LinkedIn came out, there was such an edge that if you just happen to be on the Internet and had a kind of a financial brand and had been on Yahoo Finance and had traded stocks, it was a moment of pure. Everything seemed like a fat pitch. Yeah. So you still had to write the check. So I still wrote the checks. Okay. And I didn't. I thought they were risky, but they were literally no risk checks. Okay. So I don't think that'll happen again. So it just happened to be in the right place at the right time with the right knowledge and domain experience and willing to write check. The other thing that was going in, my favorite is as little diligence I was doing. I was just betting on like what I saw. The prices were so low. So every deal I did was like a one or two or three pre money. And, and companies back then were raising 3, 400 grand. 100. Like you didn't need much to get growth because it was free growth. Yeah. But it also twists your brain. Like today I'm like the old guy going, you kids don't understand. But it was literally nirvana. And back then Fred Wilson was writing Roger Ehrenberg me Brad Feld text. It was just murderous row of good investors who had gotten their ass kicked in the first web bubble. So they were grizzled veterans who had seen something. So they were more like. And they were sharing. So it was really the luck of like, all that happening.
Yeah, right.
And so even though I wasn't in the middle of it, I had started this company, wall strip, to build CNBC on YouTube. So I also wanted to start a company because when I saw YouTube, I was like, I hated CNBC. Like, Yahoo. Finance was my thing and I don't need tv. They're all bullshit artists. And I hated that. So when YouTube came out, I'm like, also I'm like, I pitch, I cold call Fred Wilson is legendary venture capitalist. And I said, fred, I'm going to Build CNBC on YouTube. And Fred was like, that's a pretty good idea. And he invested and introduced me all his friends. So that was like how the network worked. Didn't matter where you were. Fred was like, if you knew Fred and if you knew Brad Feld and if you knew certain people in the network you were in. And it was almost hard not to know them because they were writing and no one cared. Like they were sharing how to do a term sheet, how to do. You know what I mean? It was. It was just right place, right time, best people, good prices. Coming out of a crash of Internet stocks, no one was expecting it. People thought YouTube was silly, Twitter was stupid. We still didn't even have the iPhone. It was still BlackBerry. Yeah, in a way, I was early. So again, it was just. But it was just within, you know, and you still had the great financial crisis. But if you were writing checks or had a little bit of money in 2006 and we're in the right network, you made fortune. And for me as like coming out of Toronto and going to ASU and not really having an edge, I can't say that if this comes to where we are today, I can't say that I was smart. I just knew enough, was curious enough at the right place at the right time. And I think the ultimate thing is, did you write checks? Because in the end you got it right now, by the way, you could have bought Google. Sure. And Apple. So it's not like it wasn't available to anybody. You didn't have to invest in, like the companies I invested in, like Twitter and Bitly and Tweetdeck and start stock Twits and this thing, it's just was. It was like a cluster of like. And I think the difference of today is the prices were also, like, silly.
Yeah.
I didn't know they were silly. Low and maybe they weren't, but I'M just saying it was based on the win rate. It was silly.
Interesting people.
People don't know that. But when, when text. When David Cohen started techstars, you know, was an investor in his fund. Uber was $4 million pre money valuation. This is why I tell the kids there I'm like, so you're going to tell me you're at 20 pre without a product and custom customer acquisitions. You don't even know it. Like Uber had zero cost of customer acquisition.
But is everyone on their deck?
No, but I'm saying you really think that people don't. They really had. I mean, because friends would show the iPhone business. The friends would show their friend the app. You don't have that. Who. When's the last time someone showed you an app?
Yeah.
Okay, so that's gone. So I'm saying like I worry because again, flapping forward. I worry today because people are still living thinking that era exists. That era is long gone.
Yeah.
Even though we think computing is way down and oh, everything's in the cloud. So you don't have the cost of hardware. But yes, it's something still are defensible and have big moats.
Yeah.
And founders need to have different skills. Like I'm a, I was a founder of stock twits. Right. That after I sold Wall Strip to cbs, which is another store's classic, like I didn't know what I was doing. But in six months we sold my company. You know, I took all their money and started investing. And it's nice. I said I was just doing everything right. It was like Larry David meets investing. And but the, but the investors like me, like David Cohen, Fred Wilson, they just because I was this weirdo who wasn't into tech but brought this media, I was bringing the, the financial world into the real time world. So that was my. My real Insight is like 20 minutes delay. If you thought that was good, which I did well, zero. You can't get better than zero. And that was a big bet. Like with Robin Hood Etoro Stockto. I was like, okay, just. We're just going to do that whole generation one more time. So I mean.
But I think something, a common thread with you is looking at data streams in a sense or, or trends and looking for outliers and understanding them first and then understanding, you know, what's unique and what's an edge about this. And I think you can look at the cash tag in that regard of hey, there's all this unstructured data. What if we were able to actually query on it, which became the cash tag, which I want to hear the story of, then the sharing and having the experts kind of almost just thought leadership in a sense. So I think you still downplay, like, your natural curiosity for uniqueness within data, data streams and data trends in that regard.
No, no, but you said the right word. I don't downplay anything except my curiosity. So. So I'm saying I'll take credit for being really interested in what I'm interested in. Comedy, golf, you know, not golf anymore, but like golf, sports, outside, you know, Phoenix, like, weird. They're not like culturally, but a very strong, passionate domain about what I'm interested in. And if you do that long enough, sometimes a wave just shows up. Now, I can't explain why I was so excited and my wife let me take the risk. It wasn't like in my 20s, I was already 40 when Web2 came out, so it wasn't like a layup. So I say I'll take credit for two things, like having the domain experience. I was, I was playing with, you know, like, some people are gamers and they should play because that's going to make you successful later on. Same with golf. If you, if you haven't, you know, 10,000 hours will matter in this new world.
Yeah.
Versus 10,000 hours being a lawyer. That's the worst 10,000 hours you've ever invested. 10,000 hours being an account, that was a dumb investment. 10,000 hours being a doctor. I don't know. Robots will do most of this. Scared of hospitals because of staph infections. So I think a lot of luck, definitely a lot of curiosity. And you got to be in the batter's box. You have to swing. Okay, so. So I did those things right. I'm not, you know, I'm not gonna underplay that. And I did start my own company and that strong conviction and it built my network. So you got to do all those things. So full credit. No one can take that away from me. But you still need the market to work out and you still need app, iPhone to come along. I didn't know that was going to come along. I didn't know the, you know, so I'm saying, like, there's just too many people that are taking credit for being way, you know, stick to what you really did, right.
Yeah.
Share with what you really did. Right. Be honest about what you got right. And you'll be a better investor. You won't make massive mistakes. So that's what worries me about today. I don't know what the world doesn't need more Robin Hoods. It doesn't need more stock twits. So we have to move to, like, what really is the people want. And I'm not quite there yet. I like media and outside activities and new form factors, but it's not as sexy as, like, selling software for zero cost of goods and having endless customers, you know, calling you. Like, how about now? You got to pick up the phone and, like, sell. That's a whole new thing.
Yeah.
They didn't teach you that at Stanford or Harvard?
No, definitely.
So. So I think if you're running an old Playbook, it's going to be hard for people.
Okay.
But you're, but you are still sharing that. You're still synthesizing, processing it by sharing it.
But I'm trying to share it in a way no one wants to hear it. So I'm sharing it. But it's not like hundreds of thousands of people read my newsletter. I think very smart people read it, but they don't want to hear. And I don't, I don't know a nice way of telling people this. We've been saying this for four or five years, six years since SoftBank came out with paying stupid prices. And that went on for longer than I would have predicted. So you can't time it. But I say now that it's for sure marked in stone of that, like, Covid was the last gas. The playbook has to be tremendously different. And I don't. And I haven't. There's going to be a whole new set of winners and losers and people.
Yeah.
And I'm not. That's a whole new network. I, I mean, just true, you know, so I've got to reinvent, you know, in, in this business, you have to reinvent yourself like tricks. You have to update your comedy routine. You have to update your magic book, your magic tricks. So I realize that, I think that's my edge going forward is that, like, I'm humble about the fact that thank God I made some money because I don't even understand what's going on.
Yeah.
Like, I don't. I don't use chat GPT. So am I, am I stupid? I think technically it's stupid, but because I'm curious and I don't think it adds zero. It adds zero value to my workflow today. Like, I'm still a guy who says, like, Gmail, and I'll use whatever Gmail serves me up as an answer that's about as good of AI as I need. Right. And so Maybe I'm old. I don't care for hallucinations. I don't mind Google selling ads in my search. It works for me. You know, I think I'm probably still underutilizing Google Search. I think the people that think Google Search is dead are nuts. Because I also say look at Wells Fargo. You know, 50% of people still get their statements by paper and Wells Fargo stock is at all time highs. And has there ever been a company that on customers more than Wells Fargo? So you know, while Google and Apple and Facebook are evil, you can be evil for a long time.
True.
When your products are great and the customer. So I think, I think people just aren't being honest with themselves. How difficult it's going to be figuring out what is. In an era where you can create a startup, which I agree everybody should doesn't or should think about it doesn't mean you should versus when I started the business. Why would you do a startup? You got to go get a lease and you got to go get employees and then you got to get the wait for the phone guy to show up, you got to get a fax machine and then you know, data center.
You just.
The cost to start a business were stupid. So the trap was don't start a business.
Yeah.
Okay, so be a lawyer doctor. Now the trap is start a business. Like just because you can doesn't mean you should it. Yeah, and that's what I'm worried about. And there's not enough people who want to be number twos, number threes and number fours. Yeah, right. So, so those are the things that like I'm thinking about. And when you tell a founder that you know, has grew up in 2010 and saw their, their buddy raised a hundred million dollars, how do you explain that to a young person that that game was over? They're just gonna, they think you're nuts.
Yeah, I know.
I agree. I think in the era of blockchain and now AI where everyone thinks, oh some quote unquote cool tech deserves hundreds of millions of dollars when really it's just another code base. And like I never invested in a company because ooh, was on JavaScript. Wow, you're on JavaScript compared to some other company.
Rails for me was stock to us. Like it still works for me. So as a non technologist, I'm a dinosaur. And I keep becoming more of a dinosaur because like I said, I don't use Excel, I don't trust it. Meaning I use, I know how to use it. But like if I'm using Excel, it's not good numbers. Like I'm using it like an idiot. And then second, I don't trust the people like the Chamas and David Sacks of the world who know how to use Excel and use it to their advantage and I'm using picking on them. But it's like any shark, any new shark picks. The second thing is I don't use chat GPT so I'm a dinosaur that I'm not against. I think it's fantastic. Go play with it. No, no, but I'm saying. And then the third thing is crypto is not interesting to me. It's not that I'm a believer, not believer. It's just like I don't need a wallet. Like I get why people would have one, you know, in Argentina or Ukraine. I think it's fantastic. But doesn't mean guy in Coronado needs crypto. So. So I, I have to, you know, take a pass on all this and reinvent how I think about entrepreneurship and who we're going to back evaluation. So it's really been like a four year reinvestment in like do I have the energy to go do all this? So, so the writing has helped me get through it because people appreciate it.
Yeah, you're.
And your writing is really just one form of how you express it. I think getting people together, whether it's live, on stage, in an audience, dinners, which I know you do a lot of, and then your podcasts, which you've had a few iterations of as well too. Just good at synthesizing in public, I guess is maybe I'm good at synthesizing.
I'm not good at, I'm not good at traffic. So there's two ways to do it. Right. And I think. So the question becomes if you're going to do it, should you have a lot of traffic? I'm, I'm torn by that because it makes sense. Like people say, I can't believe you only have, you know, 10,000 this or 3,000 that. And I'm like, I guess I'm an idiot. But I also, it's the only way I know how to flesh out. So. Meaning if you're not doing it for.
Yourself, it's, it's authentic though you're not.
Doing it for the dollar. Right? I make a little. But I'm saying if you're not doing it for yourself, I still don't get it. Right. So. But that's why I don't listen to mainstream shows. Right. Like so yeah. It's also Why? I don't really listen to many podcasts. Like, it's just. I'd rather. If you can write your thoughts out in a three paragraph thing, I'm your guy. Like, because if you can't condense it to three paragraphs. Right. If it takes you an hour to tell me what you're thinking, meaning if I only did a podcast, it'd be uninteresting.
Right.
To me because I'm great at writing every day two or three paragraphs. But like you can't really. The people that really want to like extrapolate what I'm thinking and take all the experience. I drift and like if that came out on paper, it would be the worst writing of all time. So I, for me, I have to do it all to synthesize it. So that. That's my little hack.
Yeah.
And it's just a lot of work in the end. Oh for sure. I do love doing it. Just even this conversation. It just helps me remind myself where we've been and, and why I have to be careful thinking, you know, that how I am best right now.
Yeah.
But I think you also mentioned some people you worked with like Fred Wilson, the David Cohen's the Bradfields, who were very similar in that their writing was almost both a synthesis but also a give. It was like a give before you get mentality too. Very much.
Fred. Fred and Brett were givers of their time. They got excited. They were older too, but. And they've been through crazy bear market. Right. Like in all the aggravation of up and down. So they were wiser. Like that was the thing. They were wiser. I don't feel like people from this last Internet have gotten wiser. They've gotten more cocky. I hope I'm wrong. Like there's obviously how giving like tech like those companies were versus a Y combinator, which is all about the money. Like they can, they can lie and say it's this and whatever, but it's just too much money. It's not even their fault. They've just made so much money. It's kind of like Harvard already. It's just a sped up version of Harvard. What they're turning out is what we're seeing at Harvard. They just did it. Instead of a hundred years, it took three years. The type of people that and behavior that I see are the stuff we cringe at when we watch encampments at Harvard. My opinion, it's not popular, but it's not good to see that decay so quickly.
I agree.
Which, which goes back to your media piece. Like you could have worked monetize everything in what you do, but you, you don't because it's for you. And you're genuine, you're authentic and you know, what comes around, goes around. And yeah, advice comes from you learning from your own advice, just like Brad and Fred did as well too. So it's not the business you're in, which is making money off of purely for the point of making money.
Well, the other thing I would tell founders, you're listening is because I'm now back being CEO after seven years away. Is that like, damn, like building a brand is like a marathon. So it's like stock twitch goes from being like the hardest thing I ever did and dumbest thing I ever did to now like have a vision and like tech is less important and it's easier to do tech. Like now it's like I can sit back and like plot what stock totes will be. So there's all these companies that are, we're going to be a hundred year company. And I was like, Mark Pincus is saying, like I remember friends with these people, they're LPs, like, like, what are you? 100 year company? Like that, that just someone says that to me. I just assume they're a lying because how would you know? Because you first get to 10 years before you can get to a hundred years. Right? And if you've read like, like the best business book, which is Shoe Dog, you know, they did 10 million in revenue. They weren't even called Nike in their first tenure. It was blue. Some blue night. I forget what it was called. But oh yeah, it took, it took 10 years for them to get to 10 million in revenue, right? And then he paid six bucks for the Swoosh logo. And yeah, you know, he. So I think it's a marathon. And I think again, another bad habit of web2 was like, look how fast you could explode. Like how fast could we go global? If we think about the billions wasted by like the Ubers, the Robinhoods, coinbases of going global before they even dominated their own local market. Because you could, because, because Sequoia would give you 300 million or SoftBank would give you 500 million. Like if we go back in the history books. That was just a lot of pissed away capital, misallocated capital. Did you need to go to China in year two? Could Uber be three times the size a company right now if they just destroyed Lyft when they had them? So I think the history. No one's going back and, like, studying how stupid that was because we only remember Facebook being the biggest, you know, or app, you know what I mean? But, yeah, I think there is some art in going back and now studying Web2 and realizing the people that made money on Web2 are not as smart as they think they are, which I worry about. Right.
Yeah.
More laughing. I'm trying to, like, make fun of myself because it's like, come on, people.
Yeah.
If you worked at Face. The more interesting thing I would say is that if you were alive in 2006-2012 and we're in our industry and aren't worth a lot of money. That's an interesting story. How did you miss that? I'm more interested in that than I am in, like, someone telling me how much money they made working at Facebook and how many app companies they started. Because that was what you're. That's what any smart person would have done. I want to know what the hell were you thinking that you were bearish through all that? And then I also want to know, can you repeat that? Now this will be. And I'm interested in that because I'm not sure I know how to do that. And I think that's the only thing that I'm interested in right now. Can I reimagine how to live in a web world where I don't want to be in the web all the time? Which brings me back to events and golf and all the things that I have to bring back in a world that has the Internet. But you don't want to be on the Internet all the time.
Right.
So that's kind of my new thesis. Is that mixed. You got to do both.
Yeah.
In person. Definitely feels like the hot new thing coming out of COVID but curated.
Right.
It's not like I want to go to a bunch of stuff. I want to go to the. The right stuff that I'm going to meet interesting people, not just my people with that is.
It's not scalable. Yes, I'm doing it, but it's like, it's. It's like every customer matters now. Like, you can't.
Yes.
Like, when Airbnb started, it didn't matter at 100 people bounce because 600 people for free would show up the next day. So it's a good lesson. And like, now you don't have that chance. Like, your first impression probably matters more than ever because getting a customer is harder. And people still have this skill of let's just get a site up. Let's not worry about what our colors are. Let's not worry about what our logo is. Like stock twits. Like I wouldn't. By starting a company, I wouldn't call it stock twits. But back then it was cool. Why do you need a design shop? Like just get a website up, right? What do you, you know, pick your colors? Like what color is McDonald's? You just like, that's how. And it was a good decision. Like, yeah, at the time it was like, don't spend money on that. You need coders. Now it would be more like if the founder doesn't have like a good name and really thought through, like how they're thinking about their first customers. I don't think they know what they're doing. So it's like a complete.
Yeah.
Rethinking of how you're going to do it. So. So like events are like really hard to do, but like that is a unique edge.
Yeah, we're going to come back to that in a second. What's the founding story of stock Twits? Who was it? You do have co founders and where.
Yeah, it's me. It was a kid named. Because I can't code. And so when a Twitter came out, I was just like, thought it was the dumbest thing.
It was.
They had tweet to text or text to tweet.
Yeah, well, because it. People weren't using it the way I would want to use it. It was like, oh, the bridge is out. And I'm like, kumbaya air spring plan. I mean, I got it, but it wasn't for me. So I would tweet to Fred Wilson, you know, I'm taking a. Or I would tweet, I'm in, you know, I'm taking a piss or you know, what's the cleanest bathroom? It made no sense, but it was outrageous in the sense that the people that were on Twitter back then were all venture capitalists and in Silicon Valley, no sense of humor, people. So I was just outrageous. And Fred knew me as a goofball because he backed wall strip. So I had instant credit. And he was an investor in Twitter. So it's like this instant credit on Twitter because I was friends with Fred. So it was like again, right place, right time, right network, right node in the network. And Fred trusted me. And so it was like a made man in a way in that world. But he didn't like me because I was just a goofball he liked because I knew I thought differently. And he could make money. He was an investor, his investor in my funds. And so I said, so Twitter was out and I was like, this should be used for, you know, BlackBerry at the time was like peer to peer. The it appear to peer message. Because so as a trader, Meryl lynch, Everybody was using BlackBerry, but they had this pinning thing on BlackBerry where inside information was starting to flow because if you went on your email, Morgan Stanley that your boss could see it, but if you pinned machine to machine, you could, no one could track it.
Right.
That was BlackBerry's thing. And so all of Wall street was using and politicians were using blackberries because it was theoretically secure. Right. That was the secure. Like that was a way to get around the wall. Anyways, so Twitter comes out and it's literally BlackBerry pinning. Right. But it's public and, and so as someone who's not Wall Street, I'm like, this is like pinning. So people are going to talk about stocks and everybody else is like, you idiot. No one will talk about stocks because it's illegal to do that. I'm like, well, I don't care about you. I care about my friends who like don't care about. Look, we're not treating inside information. We're just talking about stocks.
Yeah.
So it was like that weird. Like, so everybody thought my idea was stupid because of course they did. They're worried about like, like compliance and cheating and like doing it illegally. I was just like, I don't care. I farted. Okay. I bought Apple. What? The two things are the exact same thing. It just depends on what your interest is. And so if I say, if I say I bought Apple, you had. It was like, I bought Apple. I was like, and then you go search Apple, you would get like, oh, I went to the store and bought a green Apple. Like, how does that have to do with this? So, so the hack that I had and the cash tag existed, but if you went to hashtag Apple, it still would be, you know, it still is a show.
Yeah.
So lucky for me, with my domain experience in understanding tickers, we. I came up with the idea, sent Fred a text. I'm like, dollar sign, you know, R, I m like, I just bought rim. And Fred sent me back a message saying, this is genius because Fred was into stocks and he had backstreet.com and obviously my company and that's really what it took. And so that was the beginning of the cash tag. That was the first, I think maybe people were using dollar sign for whatever. Like rappers were like, dollar sign hit shit. Like that was a word. But it was Hitachi was actually a ticker symbol. So you know, so it was funny. Like if you go search dollar sign hit on Twitter, it'd be like rappers and Hitachi people. But no one's going to type $sign AAPL unless they're talking about Apple the company.
Right.
So that was a good hack. Didn't. That wasn't what we built the company on, but that was like the insight to go build Twitter finance. And so the idea of stock twist was like I'll build it for Jack and Ev. Like I told Fred and they can pay me 10 million bucks. Just like I sold my last company and I don't know how to code. Like I'll just. Yeah, quick Aqua Hire or. And I'll just, you know, I don't want to start another company. And it was like 40:42 and I don't know how to code and I, you know, and it's like open API Twitter. So I was like set up a meeting. Fred said yeah, this is, you know, my pitched Fred and Evan. Jack was like, this is Twitter for stocks. So twitter.finance.com and they were like, huh. You know, they. That's Silicon Valley doesn't. Other than Robin Hood. Silicon Valley is not a fintech. They know. It's. It's not that it's not. They don't. They look. They are. They have so much money now that they like investing. But then it wasn't about the money. So they didn't have Wall street. Didn't want to be Wall Street. And guess what? To be Wall street. You got it. Helps to be Wall Street.
True.
It helps to think like. Like a. Like a bit of a customer. Yeah, like your customer and understand how the pipes are done and everything else. So I just happened to just come up with the idea which was clever as Fred. As Fred knew right away when he said goes this is genius. So the dollar time is just a very clever hack that I gave back to the community that I'm probably the most proud of because probably the most undervalued thing. Meaning that's. I can't believe I gave that away.
Yeah, right.
And then Jack kind of trademarks it at Square. I mean these guys are all just pieces of work, you know. So just that whole Web2 era, the people. Yeah, God bless everybody made a lot of money, but it was just such a kind of like fake. I feel like a lot about it is. I think that I think the people are starting today, like truly today and really want to start something and really they're gonna it's gonna be better founders, it'll be harder. But the people that, you're gonna have to have more skills. You're gonna have to look people in the eye. You're going to get on a plane, you're going to have to use zoom, you have to use slack, you're going to have to remote, you're going to have to have in office, you're gonna have to have events, you're gonna.
Yeah, yeah.
So if you, if you want to start a company and don't think that that's going to be your company, you're screwed.
Yep, it's Good.
Points.
So, Dr. Start in San Diego. I believe you're in San Diego.
Start in Phoenix. And the. Oh, crisis happened.
Got it.
And I was like, you know, I don't want to be in Phoenix. After the financial crisis. And my, we had. My parent, my wife's parents had a place in Coronado where a lot of people from Phoenix depart the summer and go to the beach, you know, San Diego or somewhere. And for them it was Coronado. So. And I used to come to Corner, but I hated Coronado because it would be like, wait a minute, I'm coming here in the summer and all the people I don't like in Phoenix are here with me in the center. I was like, what am I doing? This is like a vortex of. And so we flipped it. Like, I was like, how could you not like Corona? So I said, why don't we do the school year here and leave in the summer? Which was a hack. And so it was a risk. We did that and moved the kids and, and made Coronado our winter or like our school year place. And then when all the Arizona people came, we would just leave town. Kind of weird, like, and go to somewhere not Arizona, but just travel.
Yeah.
And so Stocktons, I moved here thinking, oh my God, what a great idea. I'll build a company on Coronado. Big mistake. Hard to get engineers to come to Coronado.
Yeah.
And I used to just, you guys are so ungrateful. Who wouldn't want to. Like, there's endless parking, you got the beach right here. But engineers are a different type of people, man.
Right.
So I definitely got that wrong. Like building a Web2 startup in Phoenix, not a good idea. I mean, in San Diego it's probably not a good idea. Even in San Diego, I don't think. It's just, there's too many choices for a smart person. You got weather, you've got, you know, beach, you've got sun, you've got outdoors. You, you made a specific reason to move to San Diego lifestyle. Not, not work 247 and code. So many too many honest distractions. Like okay, you know, so you're not going to get people to work like they would work in New York or Silicon Valley. And so that, that, so that was hard and so that was a mistake. It was a great personal decision, but it's not good. You need to move where talent is now. That's different today of course but back in. That's a huge era for me in 2009, 2012. You're just. You could. Because it was in an office environment, there was no slack.
Right.
So to get the right talent to like be in an office was not a smart move.
Yeah.
Interesting. I, I remember there being a really good talent pool that you had together from the Chris Corvos. Great people. Just.
Yeah, yeah. But, but it was still hard because it was, it was. We were smart but we weren't competitive with what Silicon Valley could do.
Interesting.
Yeah.
Sense of urgency and like we gotta move at the speed of light.
Yeah. I had that but, but you know that's just not. You can't expect everybody to have that.
That got it.
Interesting.
Yeah.
When did, when did you do your first. When was the first October fest?
Was that 200 like 12. I had the idea let's create like a Salesforce whatever called DreamWorks for investing. So it was great. I just didn't know how to run a profitable event and it wasn't our business. It was always like it's a lot of work and if you're not going to make money. That just seemed dominant in Internet era. Now it's like I know how to make money off them. It's a lot of work but it's also good for building brand.
Right.
We brought it back. So we brought it back.
Yeah.
And I've, I think the Lambs theaters where I saw it way back in the day, I've even this time it's.
Going to be at the Dell. This time theater, maybe the movie theater. It's just great. The Dell's been redone. Yeah. It's spectacular. Always been a spectacular property but it's been a shitty hotel in my opinion. And now as a lucky Coronado resident, it's a fantastic putting all this money in because cities, you know, because it's old.
Yeah.
And now you have a fantastic property in a fantastic hotel.
Yeah.
And mix that with good content and there's no distraction. So if we have an event on Coronado, where are you Gonna go. You're on the island, why would you leave? So everybody just kind of hangs out. They're trapped, but in a good way. It's not like Vegas where everybody just goes and does their own thing.
Yeah.
You know New York where you, you disperse. So, so Corona, everybody hangs out and it's like two days of networking.
Who are. Yeah.
Who are some of the attendees? Like where, where are the kinds of people that come out and all the way out to Coronado for this. Besides for this.
I'm from Japan. Like I'll like so a lot of fintech companies, a lot of great investors that aren't famous. But like I respect. And so it's really just how to position yourself as an investor, a networker for the next, you know, five to 10 years. And what trends are interesting to us? People who've made money, they may not be famous but like, because I don't call it investment, it's just the idea of money, you know, you have to break it down to that. It's not about finance. It's like kind of weird, but it is really about money. Who's good at making money?
Yeah, right.
Without cheating, like the market. We're not looking for an edge that way. It's just like how do you read the tea leaves? Where's the puck going?
Yeah.
And who are people who have done it in the past? Right. But.
Right.
And to me those people are the same people that like are thinking like me. It's like what worked before won't work again. You have to take the knowledge you got and the arrows, you know, the wins and the losses. But like what's happening now and what's changed? I think that's kind of what we're, that's kind of who I invite to the show to speak. And it's kind of like, you know, it's like putting together any show. It's like some speakers fall flat, but like generally it's, it's, you know, people that are just really see the future pretty well.
Awesome.
Well, I'm excited to be a part of it.
Yeah.
So we have, we have like 30, 40 tickets left. If you use Howard Howard 30 capital H Howard 30 get 30% discount if you're local.
Cool.
If you're within an hour, it's worth coming down.
Absolutely.
Yeah.
Anywhere, you know, even la. A lot of people from LA will come down. But yeah, if you're within an hour, you can go home two nights or just at the Dallas music.
Yeah, no, it's fun. Little spin offs happen a Little late night cigars on the deck there. You know, it's a good event for sure. And good people.
I'm looking forward to really good people. It would say it's like people from between 25 and 70, but it's generally people who love investing more than like startup. Yeah, there'll be some startups there, but it's just the art of investing in the art of networking and building good relationships and like really honest talk about like what I'm telling people now. You don't have to believe me because there's still the old way can work if you thread the needle and you have some special skill. But I feel like on the whole we're in this super flux moment, you know, and I don't have the edge because I'm not playing with chat GPT and I'm not using crypto soap. They don't want to, you know, so those people that are, if they're right, they have a huge advantage.
Yeah.
But the, the art of conversation has never died and that's what's going to happen here. And you'll hear from people if they think they have an edge. And that's another way that you're synthesizing it for all of us.
I never, like, I never have been interested in real estate until now and not in the typical way that other people think about real estate. It's repurposing. It's like.
Yeah.
Fascinated by like different forms of this because everybody says the word venture now, like it means something. And I'm just, I prefer to call it investing.
Yeah.
Okay. So if you truly are a venture investor, then you should price things for venture returns. And no one's doing that in my opinion.
Right.
So I just, I just think it's one term and there's many ways to invest and I think good investors realize like what would be my return if this goes right and is it worth the risk to do that? I don't think people are doing like just going back to basics. Like what is my irr? What will I get back if this works out? Is it worth. Or should I just say, hey, good luck? Like this doesn't meet the math criteria of like my time and what I could do elsewhere. We have to get back to that part before we can get to the next stage. So that's kind of what the event is more about. Not. Not phrasing it is. So people who are interested in investing is what Stocktoberfest is for.
Yeah.
And that's seed stage real estate, stock market kind of yeah. Hearing from people that have made money in different markets and how they think about risk and reward and. Etc.
Okay. Well, awesome.
Well, we're looking forward to it. Being in San Diego, being in Coronado, there's obviously quite the taco scene. Us two Jews, though, that. That means sensitive tummies. So maybe not every taco spot is the right spot for us. Do you have a favorite taco spot that's safe for you?
I do and it's not. It's so like non traditional. Right. It's just like goofball. It's. I go once a week because I love Little Italy. Not. Not tacos, which is kind of like foofy. They're not even tacos. They're just made up cool flavors and weird mixes of meat and. And fish. So it's not a traditional taco place. Right. And it's flour tortillas. So I'm like very. Not a typical taco person.
No, I love it.
It's like, I don't like corn tortilla. I don't like corn tortillas.
Interesting meats, you know, like, interesting and great sauces.
Yeah. Get like a handful of them and then you can go for ice cream right there. My favorite cooking. So yeah, you can walk around Little Italy, which I like, and the weather's always great. It's phenomenal. So it's more of like an experience. But I don't think it's a taco. Taco place. But it's my favorite favorite.
I love it.
I don't think it's been mentioned on this podcast yet. So adding it to our database. You've been long, literally for like a long time. Like you saw before what it is today, actually.
Yeah.
I remember you were camping out at the co. Working space there in Little Italy for a while.
Yeah. If I were to start something, that's where.
If.
If I was going to build a big San Diego company, it'd be right there. It's near the airport.
Yeah.
Young people would love it. And it's very Brooklyn. It's like Brooklyn.
Yeah.
A better location, right?
Yeah.
Yeah, totally.
Well, I look forward to seeing you soon. It's been fun getting together with some of our Jewish peers in the tech industry this summer. And we're going to continue doing that because there's a need for us to be together with each other more than ever. But even more so. Looking forward to the return of Stocktoberfest to Coronado. Know October 20th, 21 22nd. And look forward to seeing all of our listeners there. Come join so, thanks, Howard.
Thanks. Bye.
See you.
All right.
See you soon. Cheers.
Cheers.
Startups get the party. Startups get the party started.
You want teles tacos, you know tacos in tech is on smash for the green guacamole keeper Counts counting beans contador quentan frijoles Founders trying to raise some queso la vida San Diego school of rappy rapping fire tortillas round jalapenos in these modern times of craft beer and coffee my coding yoga posse fold the body origami we be surfing coronado eating the tacos el gordo the tacos stand in puesto lucha libre and sombrero gotta shout out to coast angels by the ocean watch the sunset la Jolla shores Entrepreneurs trying to get funded when San Diego Startup week is popping in the summer Oceanside, the Tijuana esti be full of hustlers from couch surfing to penthouses right on the beach. Tech leaders who believe stars are within reach we interview and founders who be shooting for the moon SD Tecos with your host, Neil Bloom.
Startups get the party Startups get the party started. Startups get the party. Startups get the party started. Startups get the party. Startups get the party started.
You want tech in tacos, tacos in tech, you know we got it, hey.
Startups get the party started. Startups get the party started. Startups get the party Startups get the party started. Startups get the party Startups get the party started.
You want tech and tacos, tacos in tech. You know we got it, hey.
Yeah.
You know we got it, you know we got it, you know we got it.
