How To Pick Startup Winners With Jason Calacanis

Only Invest in Companies That Have Products in Market and Have Revenue for Your First 20 Investments As An Angel. So, when you even see if I'm getting frisking, I'm investing in a pre-revenue company. Don't do it. Wait, just invest in all revenue generating companies for your first 20 investments and then put the smallest amount you can in. If the minimum is 5K, ask if you can do 2 or ask if you can do 1. I have people do that all the time to me. Like, hey, your minimum is 4K on this deal because it's 250 slots and it's a million dollar allocation. Can I do 1?

And I'm like, sure, do 1. I have people ask to push 500 rolls and your incredibly invested one like, okay, you know, if we have room, sure. And I encourage them to like take their time and to learn how to do it. If you're keeping cash anywhere that isn't paying you a high interest rate, listen up.

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will. Check out Lemon.io today. Jump right in, man. Cold open. I do want to start there. Actually, it was actually what I wanted to ask about because about a month ago or so you tweeted something out. You said VCs having a liquidity path for crypto with retail investors is problematic.

You talked about what you talked about on the odd lot podcast. This general idea that VCs were pouring money into these liquid tokens or semi-liquid tokens and then basically dumping that very, very shortly on retail at these massive markups and then retail was left holding the bag. I pushed back because I was under the impression that a lot of these VCs were being asked to sign up to two-year investing schedules or something on these. Maybe it's just my own naivete.

I'm curious to just get your general perspective on that as a starting point of what are you seeing out there that's happening? What do you see happening in terms of the regulatory and legal landscape around that next? I'd start with we don't know what the VCs are doing and to be clear, I'm not talking about any one VC firm, any one law firm or anyone coin. A lot of people are like, you're talking about Andreessen, you're talking about Solana, you're talking about this,

you're talking about that. I have been talking about crypto for over 10 years on the podcast. I was one of the first people to cover Bitcoin. I've booked Bitcoin at like $2 with $3 and then again at $10, $200. I've been OG crypto for a long time. I understand the space, I'm not a code or a developer, but I generally understand what's going on here and I've invested in 350 companies. That's sort of where I'm coming from. I also run the largest syndicate in the world with 11,000 accredited

investors and I've done over 260 deals. I understand the nuances and I've learned this through a lot of hard work, how to deal with basically managing a large group of investors. I have had to only work with accredited investors because and I don't think that's the way the world should work. I think anybody should be able to with a basic license, like a driver's license, if you think

about like that, become accredited. I don't think accredited should be based or accredited accreditation in the United States should not be based on your network because you could be a trust fund kid and be considered qualified, accredited and you could be like and have an MBA in economics and have written the book and teach it at NYU and be under 200,000 a year in income.

So it makes the absurdity of it, too. By the way, like around accreditation that I just find hilarious is like, I can't if I'm not accredited in America, I can't invest in like my buddies startup that he's creating, but I'm allowed to go invest in like a triple X levered, you know, mortgage ETN through my brokerage account with no questions to ask and that's absurd. Like the risk profile of those is pretty different, I would argue. The intent is great. We want to protect

people from losing their money. It's, you know, we're talking about like decades old laws, like, you know, going on 100 years here, you know, when these laws were formed. So they obviously have to be reformed and they are being reformed. You know, now you have a lot of exceptions that have been made. If you work at a venture firm, you can become sophisticated. If you have a series 67, I think, or something, you can be, I don't know all the nuances of it, but people are starting

to get themselves accredited. It should be much simpler. I teach a course angel university. I've done it 30 times. I give all them an HRD and that would be a perfect proxy for people. And I would do it for free to help people get accredited because I do want to see people participate. So there's a long way of saying I am 100% pro a sophisticated investor class emerging with a simple driver's license test. The driver's license test is not easy, but it's also not hard. If you put 10 hours

into it or patty scuba diving, I don't know if you guys are patty certified. I'm patty certified. You got to read a book. You got to take five exams. You got to do four open water dives. Seems reasonable to me at my cost you 100, 200 bucks. That would be enough friction for people to be sophisticated. And then they could invest in very speculative specs or tokens or startups. All of these things are speculative. Right now we just tell them to go gamble in Vegas.

So let's put all that aside so you just understand where I'm coming from because there seems to be like. Have you seen Matt Levine's, I'm an idiot test that he's written about in the past. No. Matt Levine, the bluberg writer, his idea around the gradination is, uh, basically you should just have to sign everyone can be accredited. And all you have to do is you just have to sign a form that says, I know I'm being an idiot by making this investment.

Perfect. And you just sign it. And it's like same general principle. You're like, okay, we're an invest in something speculative. You just have to say, I know I'm being an idiot. I'm probably going to lose all my money on this. Totally fine. Tung and cheek, but it's tongue and cheek. But you know, to be honest, I think that's suboptimal. I know some people are radical. It's your

money to what you want with it. The reason I wouldn't be in favor of that is because with this much money at stake and with a global market with no friction, i.e. crypto, these are all good things about crypto. You know, people can lose a lot of money very fast and there could be a lot of people who get harmed and people could be duped. And then you have situations where people are front-running markets and doing all kinds of crazy things and people are not diversified and they're making one

bet, etc. So let's pause. We'll put all that aside. So I just want people to understand where I'm coming from. I am not a crypto hater. I think there's some interesting technologies there. But I do think 99% of the ICOs and crypto projects have never materialized into anything reasonable. And I think a significant portion of them have been built by either grifters, incompetent people,

or some combination of both. You know, same could be said for some startups as well. But in startups, we give you the money after you've proven something, not based on, you know, some incredible idea and we give you $100 million on an idea. And so what's happened in crypto is I think a lot of VCs and investors and law firms have talked themselves into and you know, I'm no legal expert. So we'll see

if they're right or wrong. It seems like I'm probably a little more right than they are at this point based on the SEC's actions. But they basically convinced themselves that these tokens are not securities. The SEC seems to think they are. The SEC obviously could do a better job of making this clear. But I think the SEC's position, and I don't speak for them, but I'm just guessing here, is well, you've been a venture investor for 10 years, 20 years, 30 years. You've deployed a billion

dollars. You've played by the rules this entire time in terms of who you take money from and how you deploy capital and all the legal work you do. And now you're paying a hundred times the legal bill to construct a foundation in Panama. And then buy some tokens ahead of time and then get them listed on some markets and then sell them before the company has a reach product market fit. But you wouldn't take these companies public that have product don't have product market fit.

In fact, you told Uber and Airbnb to stay private until your 10 so that they were really ready to go public. So they basically figured out a public market. If you want to call it a strategy, some I call it a scheme, some I call it a grift, you know, depending on how simple you want to be, to clear out those positions. Now we don't know to your point if people have cleared them out. But we do know that the bag holders are retail and largely retail and that they bought these things,

you know, like buying lottery tickets. And you know, now you have the reality of a lot of people have lost their money. We knew that would happen. Everybody saw a comment. And those people have a free option now. They made these bets. There was a murky legal environment. People convinced themselves that they paid a million dollars to get some legal opinion or to structure something in Panama or

some Caribbean island that this would all be fine. Why did they spend 100 times the price to raise this money and create these structures than they did for the ones that they were doing before? Why would they do that? Why would you spend a million dollars setting this stuff up legally? Well, you don't only set that up, I think the cynical view of it would be. You set up these structures. You paid all this legal money because you knew you were going to dump. You knew you were

going to clear these positions and you knew it was going to be lucrative. That's why you went through the expense. Instead of just raising money, they could have done all these tokens could have just been sold to accredited investors only. That would suck. But you know what? That's what I do. I write a deal memo. I syndicate a 500,000 allocation in calm.com to a couple of hundred angels now over 10,000. And if they want to invest, they invest on average back in the day. It was three or four

thousand now. It's probably six or seven. So I could have 25 times the number of people participating in my syndicate if they were not accredited. But I don't do that because I want to play by the rules. Would I like to have my mom or my cousins who are not accredited be able to participate? Yes, but they can't. So I play by the rules. And I think that's what's going to happen now. Now that it's all come apart, just like we're seeing, you know, in the global economy, stocks, NFTs, crypto,

you know, any alternatives, real estate, pick the market. When the market collapses, everything gets stress tested. And I think this stress test is going to result in countless. And I mean countless lawsuits, hundreds of lawsuits. Because I saw this with the back on merits. I'm not some like, you know, clairvoyant here predicting the future, you know, I'm not no stradamus here. I've seen markets collapse. The comm era, there were lawsuits for years.

What's your, what's your optimistic take, you know, five, ten years from now for Web 3? I think you've, you've spoken a lot about, you know, the faults of Web 3 and there's tons. But I'm curious, you know, what is Web 3? Look like in five to ten years. All right, so Web 3 is a collection of assets, right? People include blockchain in there. They include smart contracts in there. Distributed computing is in there. Permissionless,

you know, trustless, serverless, peer-to-peer. All that is part of this, you know, technology stack. So you're really asking like, what are, where are these 17, what's the future of these 17 technologies? I'll tell you like there are two things I think that are super promising. Or maybe three that I think could have legs. I think NFTs are a very interesting technology

when certain rights are attached to them. So if I were to buy my Soho House membership or the battery or my golf club membership and it was an NFT and then I could take my golf club membership or whatever it was. And under some sort of smart contract rules, I, if I pay $25,000 to become part of my local golf club or $5,000 to be part of Soho House, I would have the right to sell it to somebody else. And I could get back up to 100% of my original investment, then 50% of any gain,

and then the Soho House or the golf club got the other 50%. And the golf club had to approve the person and I had to approve the person. So both things had to be true. Or I didn't need their approval if it was over this amount, whatever it is. And so you could see that being like a very interesting way to do it where the golf club is saying, hey, by investing in this, it's your right to do this. And in fact, that we invested in a company and we bought two NFTs from after-party,

which is doing this essentially making music festivals with this concept, right? And every time with my two NFTs, I get four tickets to their music festivals. I was like, oh wow, it's almost like I'm an original patron of Sundance or an original patron of Coachella. Like if you're a Sundance patron, which is a nonprofit, the film institute, you get, you know, like nice tickets and you get to go see movies and go to parties. So that's kind of interesting, right?

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more on your money and build wealth for your future. The Wealthfront cash account gives everyone a 1.4% APY interest rate, which is like 20X the traditional bank's payment today. So if you kept $10,000 in a Wealthfront cash account for a year, you'd be on pace to earn an extra $140 a year, instead of like $7 or whatever a bank would pay you. That means that while your money earns 20X more, you can keep saving more. Whether that's for an emergency fund, a down payment on a house,

or your honeymoon to Italy or Greece. Talk about a no-brainer. And unlike your other saving options, you'll always have access to your money. Thanks to unlimited free transfers, free access to over 19,000 ATMs and no account fees. And if you ever want to invest with Wealthfront, you can move your money into the market in minutes to grow it even more for the long term. Getting a cash account is super easy. It only takes a few minutes to sign up and then start earning

that sweet, sweet 1.4% interest on all your cash. And if you start now, you'll get a free $50 bonus with a $500 deposit. There are already nearly half a million people using Wealthfront to save more, earn more, and build long-term wealth. So why wait? Earn 1.4% on your cash today. Visit Wealthfront.com slash Happens to get started. Again, that's Wealthfront.com slash Happens. This no-brainer good news has been a paid endorsement from Wealthfront.

All right, and so the other thing I find pretty interesting is like DAWS. It's kind of interesting for a group of people in an LLC to make decisions together, but have it be programmed into it at the start. And just have it running in the cloud. So as an example, it's a company called Pekasa, which takes a home. We'll turn it into eight shares. We could all buy this home in Tuscany. They would provide all of the furnishings. They would manage

when we each got our weeks. And if we both want to Christmas, they kind of have an algorithm to manage that. So it's fair. For the premium weeks, Yadayata, they charge you an expense. They get a little bit of a VIG. But you actually own it, right? So now imagine that same scenario, but without a company, we buy the same beautiful farm in Tuscany. And we each own roughly 33 shares in a 100 unit LLC. Each two shares in the LLC in this DAW equal a week at the place. And each one has a

cost of $2,000 in maintenance a year. So then I decide I'll sell four of them to a friend or a family member. They get two weeks there, but they also have to pick up the cost. You two get first ride a refusal on those shares, or you get first ride a refusal over 10 days for half of my shares. So if I want to sell the four, I have to share you four other ones, whatever we come up with as our concept here. And it all just happens programmatically. And you saw some promising stuff where a lot of

people would love to throw in some money to achieve some goal. And so that goal could be for us to have a farm in Italy. It could also be for us to buy the next. It could be also for us to buy Twitter. It could be for us to save the wells or buy acreage to deal with the rain forest or a nonprofit instead of giving our money to some scholarship fund. We could say we're going to put money into this to provide STEM education to disadvantaged students. They apply we all vote on

each application. And you have 10 days to vote on each application to give scholarships to people, right? And then you don't need to have this whole nonprofit running the scholarship program. It's done through this Dow that everybody agreed to. So I do think there are promising things there. The things that I don't think are particularly promising or maybe overhyped is the blockchain as a database sucks. You know, everybody knows that it's slow. And it's never going to get super fast.

At least not when compared to, you know, you know, modern day technology that doesn't have to, you know, be immutable and distributed. So it's always going to run behind now. At some point, Moore's law will be so great that maybe any modern function would be fine on there. But this idea that there are no, there's no central authority is another thing that most people don't want. So most people who, you know, you know, are buying into the crypto would very much like to have their

trend, their transaction reversed if it was hacked. Now other people see that as a feature. Like, paha, you made a mistake, you did it wrong, you lost your NFT or you got hacked, hey, it's on you. I think that the majority of consumers don't want that. So there might be some consumers who do, there might be reasons for wanting it. I'm sure. But I think most people do like to have some central authority. So a lot of stuff is overblown. And I think the main problem, I think ecosystem

crypto has is it got co-opted. The original true believers and the technology had very good ideas. I met a lot of them. I had them on the program this week in startups. But a lot of them got, you know, kind of diminished in their voice in this whole crypto ecosystem as people came in just trying to secure bags and flip things. And that's really the tragedy of this, just like the doc on there, a lot of the people who we were building the doc on movement, we were building websites,

we were doing it because we were enthusiastic about what it could do for society in the 90s. We wanted to see people have a voice and be able to publish things without permission. Like that was what it was about, you know, and to be able to communicate with people across borders. And then people came in and were just like, hey, there's a quick way to take a company public and secure a bag. So I think that's what's happened to crypto. Now I was waiting for this crash. A lot of people I

know and crypto were waiting for this crash. So hopefully it flushes out 70, 80% of people and then some regulation occurs. And then the people who are left are people who actually can ship product. There's been very little shipping of product. I also think the gaming space is kind of interesting. I like to gamble. I like to wager. I like prediction markets and stuff like that. So I do think there's some wagering and interesting things there. You and I want to bet on the, I don't know,

a next game where we want to play online poker. We put our tokens in, we put our Bitcoin at, we stake our Bitcoin, whatever. And you know, if we lose a hand, the money just gets transferred and there's no intermediary. This kind of stuff is interesting, right? And so where you and I want to make a trade on, you know, I don't know what the price of oil will be at the end of the year. And you know, here is our Oracle. We both agree that this website or this data

service is going to be the proxy for the oil price. And we just make that that and it doesn't cost us anything, right? Nothing that's problematic. Why isn't it all free? Like, what, weren't we supposed to save money on this? Like the gas fees and stuff like that is just ridiculous. If you're going to make this competitive, it should be 10 times cheaper than whatever the best deal is. So stripes 3%, this thing's got to be like point 30 basis points.

Like it's got to be really competitive with what's out there. And it should be, but again, back to secure in the bag. It seems like some people love to get these gas fees. And yeah, that's problematic as well. It just seems like, you know, decentralization became this like dogmatic buzzword. And to your point, you know, there's the real efficient auto's out there that say, oh yeah, you lost your money. You got fraud, you know,

scam, your platform got hacked, whatever, like, oh, too bad. You know, that's sort of the price you pay. And that's how it works. You know, not your keys, not your coins. And I just like, like, my head that turned out to true. Yeah. But like, my thing that I keep going back to on all of this is that centralization is good in times of crisis. And like, I think that across

decision making authority too. And so when you talk about DAO's, like, I think a lot of the use cases you talked about are interesting in the context of a DAO where you have like, you know, governed into cross a bunch of people for like, you know, investing behind causes and more of homes or things like that. But if you're talking about a company, like there was this whole thing of like, every company is going to be a DAO and community governed into everything.

And my whole thing with that is like, that sounds fine when everything is up into the right and times are good. But when shit hits the fan, like, there needs to be a general that is able to go make quick decisions really fast. And I just don't think you can rely on a community, you know, distributed decision making in times of war. Default to centralized and, you know, default immutable default, you know, smart contracts, probably not what most use cases should be.

So I think there was this like, drunken, you know, fever about these coins because they kept going up into the right. So people were like, well, if I'm making all this money, this has to be the winning strategy. The problem was the strategy was never executed. So we actually don't know. We don't know at scale if, you know, a crypto version of Airbnb where, you know, there is no

central authority, you know, making sure your house doesn't get robbed or trash. If that would be better or not because you would take out all those fees, you know, happy to see somebody try. But I don't think, you know, a marketplace like, you know, eBay or a financial service like PayPal or Stripe or, you know, Airbnb, like I actually don't think they work better. I don't think most consumers would pick the decentralized crypto version over the centralized trust brand.

People are underestimating central. I also think we saw a lot of bad actors in the NFT space. So the 10,000, the 10,000 TFP collection cookie cutter 0.1 E. That cycle from 2021 to early 2022 and just that rinse and repeat that people were doing, where NFTs, like we often forget, NFTs don't actually need to sell NFTs at all.

So for example, I'm happy to see a lot of freedom in NFT projects take off. Like the 100 fees did a project where, you know, they're a popular gaming community, you know, they had 700,000 people mint for free these NFTs to celebrate their championship. That's awesome. We don't need to sell, you know, we don't, we don't need to sell it. So I'm excited to see more freedom mint.

And to your point, yeah, I mean, it was like, it was like arbitrage, right? Like it was the same exact vein as what Jason was saying early on of like some of these VCs just taking advantage of an opportunity to make a quick buck and like these guys came in and it was like, hey, you can go make, I mean, there, there was a point in time where this had to be the best way if you were like somewhat smart and you had very low morals, it was probably the best way to make like $5 million.

So you want to tell that story? We had that. We were, you want to tell that story about our friends? Yeah, I mean, we had, yeah, we had a group of friends who basically had this idea where it was like, hey, let's go, we have large platforms on Twitter and social and let's go like, you know, this is a

great time. We can go create some amazing artwork and we'll build this school universe and we'll go like create a project and we originally, like Greg and I originally started work on it thinking like, okay, yeah, we can go create like this cool velvet rope thing. It'll be a cool community. We'll have like this type of utility around it. Yeah. And then pretty quickly it became clear to both of us that

our friends that were kind of wanting to do it were really just like, there was no roadmap. It was just like, here's how much we're going to make in the mint and they'll have to move on. And so Greg and I both like pulled the plug on it just walked away from doing it and it never came through because I was like, look, I also, I mean, I have a small fund. Greg has a rolling fund. It's like totally unclear

to me. And honestly, probably likely that like two years from a lot of these people get sued or the SEC comes after you and I don't want to get banned from, you know, for doing something stupid like that. It was like, it was ludicrous to me that that could possibly be worth the money. But I think a lot of people viewed it that way. You could just, I mean, you could literally make five million dollars in

like a month if you had low morals. I think anytime you, I've been introduced to some sort of investing space, you know, if you look at the tactics being used with the new entrance, that can tell you a lot. So if you come to a poker game, somebody's a fish, I'm going to get invited to a lot of poker games. So obviously you're like, wow, I'm so popular. I got invited to this one poker game and then

two people of that poker game invited me to these two other poker games. And when I was in LA, and I was just starting to play poker, I was getting invited to all these games and they were, wow, I'm super popular. And I was like, no, it's just bad at poker. Now, these are $200 poker games. It's like nothing. So people were just like, oh, he's a well. He doesn't care. And yeah, we can charge him, you know, $200 every night to learn how to play poker. And in fact, that's how I looked at it.

I was like, yeah, I'm going to learn how to play poker. I'm just going to go to the Hollywood Park casino and buy into a $20,000 for $35. And I know I'm going to lose, but I'll learn. Great. The problem is you wouldn't want to take that technique to the high stakes poker games and buy in for $25,000, knowing you're in learning mode. You can literally learn for a thousandth of that equally well. So then you look at angel investing. People want to angel invest in me. They have to

be accredited. I tell them to take the course. I tell them to read the book. The course is free. I mean, you pay 300 bucks, but we give the proceeds to charity. So we just do that. So people don't burn the seats. Your first investment is going to be four or five thousand dollars. So it's nothing. It's literally giving a tiny donation to charity as an accredited investor.

And then the book is essentially free. I mean, books are 10 bucks or 20 bucks. I literally tell people only invest in companies that have products in market and have revenue for your first 20 investments as an angel. So when you even see if I'm getting friskin, I'm investing in a pre-revenue company. Don't do it. Wait, just invest in all revenue generating companies for your first 20 investments and then put the smallest amount you can in. If the minimum is five K, ask if you can do

two or ask if you can do one. I have people do that all the time to be like, Hey, your minimum is four K on the steel because it's 250 slots. That's a million dollar allocation. Can I do one? And I'm like, sure, I do one. I have people ask to put 500 dollars in your accredited investment. Okay, you know, if we have room, sure. And I encourage them to like take their time and to learn how to do it. Now let's look at crypto. So in poker community, like they're trying to get more

fishes and wells at the game. And you know what? I so crypto is very similar. Half-un being poor, you don't get it. Okay, boomer. Not going to make it. Going to make it, you know, all this peer pressure. I would say something like, no, listen, Bitcoin is a great technology. It's been proven, pretty robustly over a decade. But it will be replaced by a better technology. All technologies replaced eventually by a better technology. And man, the Bitcoin maximalist and then the toxic

Bitcoin bros went crazy. And I was like, well, please describe another technology that after a 10 or 20 year run, was it replaced? Oh, HTTP. Okay, sort of. Maybe, but we do have AMP and other, you know, you know, extensions to it. But yeah, sure. Maybe, yeah, it happens once in a while. Please name another, you know, and like, it's pretty hard to name, right? Maybe email, but a lot of the email communication has moved to chat and other places. So it's very hard to imagine that

Bitcoin doesn't get replaced at some point. But that doesn't mean it can't have a 10 to 50 year run. But even saying that, man, it pissed people off. And I said, listen, Bitcoin zero is a possibility. What if it gets hacked? What if it gets compromised? What if it gets banned? What if there's some denial of service style attack that we can anticipate here? A blocks one event? All kinds of things can happen, right? These things do happen. Oh, you don't get it. You're, you're being taught, you're

have fun. I'm like, I said, I've made seven figures on Bitcoin so far. And I'm saying this, I'm being intellectually honest. So I probably have a bigger Bitcoin position than the people who were in my replies. Yet they're telling me I don't get it. I'm like, well, I bought it at three and a hundred and 200. Now I lost the $3 shares because I didn't have the keys in the website that compromised. I mean, it's just like being honest about upside and downside around these things. And people

during times of overwhelming optimism, no one likes the person that is saying those things. Like two years ago, I mean, I just saw this on Twitter today, I think. But like a few years ago, you made the prediction that there was going to be something that happened over the coming couple of years that was going to, you know, destroy a lot of these startups that hadn't been thinking, you know, about what could go wrong. And they were only thinking about a world where

numbers numbers go up, right? It's like the crypto saying numbers only go up. And that's, I mean, it's just an important thing, right? Like you need to envision the possibility of failure. And then Joe from oblots said like, this is the stupidest prediction ever. And then it sucks back in the day. And when I had written this in like, I think it was December of 2018, I said, listen, is your captain speaking? Things could get a little rough here. I've never seen a bull market this

long. Just make sure that you have a path to profitability. And you got some good cash in the account and you're raising money at the top of the market. Well, pretty, you know, in hindsight, great advice, but it's, it's, I don't give myself any credit for it. It's kind of simple advice, right? Kind of one on one, to be honest. And sure enough, I was off by one year or 18 months.

Yeah. Nobody can time it. But I was trying to, I was seeing exuberance that made no sense. Like people putting a hundred million dollar, giving a hundred million dollar valuation to a company with no revenue. And, you know, 4,000 VCs using the product. And you're like, okay, I think Clubhouse is cool too. But there's 4,000 people in here. And it's worth a hundred million. That doesn't make much sense. Okay, now it's worth a billion. It has no revenue. Now it's worth four billion.

It's like, really? I, is this make any sense? And it obviously did not make any sense. And then hindsight, you know, they're going to have to go down to a 250 million dollar valuation and build back up. But they did also the bag. So you got to give them credit. It also kind of points to your earlier, the whole discussion around like, you know, crypto tokens and coins and how the like who was holding the bag on all that and how the VCs were doing that. The other group that was

holding the bag on this that I don't think it's talked about a lot was large LPs. Like a lot of these pension funds and diamonds, insurance companies, et cetera are like implicitly holding the bag on this crypto stuff because these funds, a lot of the funds that when did that then marked up, you know, massively their initial investments and went and raised insane funds with huge fees. Like, you know, go and raise a billion dollar fund to go invest more with a two and a half percent

fee at the top of a bull market. And now all of those pension funds, you know, who are like investing firefighter and policemen and teacher money are paying two and a half percent like exorbitant fees on, you know, investments that are going to be massively underwater or investing, you know, the one caveat is these are the most sophisticated investors in the world. So, you know, I look at the stack and I say how sophisticated how long have these people been doing it?

Like these LPs of these funds venture is, but, you know, 5% or less in some cases is ballooned up to 20%, 25% when venture has got big markups that can get bigger, but intentionally they put it at 5%, sometimes 10%, depending on the aggressiveness of the fund. And they kind of know what they're buying into. They know it's cyclical. They know those boom bus cycles. They know they can, you know, have a 20X fund and they could lose 50% of the fund. They're kind of protected in their

diversification. They, yeah, maybe they pay too many fees, but they don't have to. They have other places they can put their money and they're choosing venture over private equity, choosing crypto venture over venture, traditional venture over private equity over real estate, over bonds, over commodities or whatever. So, I don't really worry about them too much. It really is like the consumers and then the unfairness of the trades that I think is what's going to

result in the most lawsuits. Because what happens is, and I, you know, I hate to be like the spoiler here, but just I always try to keep it 100. If the kids say like, be totally candid, there are a bunch of district attorneys. They all are running for some next office or keeping their current office if they're elected, not appointed. And they all have a lot of pride in protecting their citizens. So, selfishly, they want to stay elected or they want to, you know,

aspire to be governor or something. And, you know, being a DA is a stepping stone. It's prestigious. Well, what's the most prestigious thing you can do? So, take down Martha Stewart. It's to stop the mafia. It's to stop some crypto kids who absconded with the money. So, you have to be a little bit self-aware here that if you screw over a bunch of people, you know, in some city,

in Idaho or Florida, there's going to be some DA. It's going to be like, what? Seven people in my jurisdiction got screwed by, you know, BicConnect or, you know, whatever.

I was my own BicConnect. Yeah. So, we're going to come at you and we're not going to stop. And if I get that pelton put it on my wall, I'm going to be able to say when I run for governor, yeah, you know, all your friends who lost money in crypto, I was able to prosecute 17 people just like, you know, somebody else running for over, oh, you know, I stopped online poker, you know, I stopped the mob, you know, Rudy Giuliani ran on, you know, having stopped the mafia in New York for a

long time, right? So, that's what's going to happen here. And it could be unfair too. They went after people on Wall Street after, you know, Henry Bludger famously was banned from ever, you know, working in securities for life. That's a couple of emails. You know, where he was like, yeah, I think this company's a dog, but we have a vibrating on it and, you know, I don't understand, you know, like, he was like, okay, you know, that's kind of the modern day. And Henry said,

delightful, great person, probably learned from that. I'm sure I'm sure he did. I'm fond of Henry as a writer and thinker. But is he the head of insider? Yeah, which is to be Silicon Alley insider. And you offered me 5% of it because I had Silicon on a reporter magazine. And I said, no, you know, just keep it. That was a stupid mistake on my part of probably a couple of a little about. Do you on all of this stuff? There's this one area I've been wanting to ask someone

about. I feel like you're a good person to pine on it. This whole trend of people on Twitter, newsletters, podcasts, whatever, being like saying a bunch of stuff about some idea, you know, like recommendation thing they're investing in. And then saying like, not financial advice, do your own research. I think it's absurd because like, like, I read, you know, there's like the crypto newsletters, right? Like, and I'll read it and they'll do like a bull case on some crypto token.

And then at the bottom in tiny font, it'll be like, not financial advice, you know, do your own research. I'm like, that's fine. You said it like, okay, maybe you're like covering yourself. But everyone considered that their research. Like they read that. That was their research. And the number of people that go in then. Yeah. And the number of people that go and buy the thing. And then lose, I mean, like Luna, you know, people recommending Luna to buy as like, oh,

this super interesting thing. The number of people that lost money and like millions of dollars, obviously, is that imploded off of like, you know, Twitter, newsletter, whatever. I mean, that to me is like an area that regulators need to look at. I think a lot of people probably deleting a lot of posts. A lot of people deleted them. They're like, maybe I shouldn't have put that in an email and sent it to a million people. Sitting in people's email boxes. I think about

that. I write deal memos, you know, and we do do diligence on companies. We can, you know, and we're upfront about this. Like founders could lie to us. Founders could take the money and go to Vegas. Like they could go on a bend. They could be incompetent. Like really, you know, invest the least you can. And I tell people in my deal memos, the bet. And I use the term the bet. Because I want people to understand this is a bet. You know, and I say, here's how I'm making my bet.

You just so you understand. And I frame it as that because we are making bets here. And so, you know, I just started J trading. You know, we came up with a funny name for day trading. So, I think it's a unique opportunity to buy public equities. I've never played in the public equities space. I've always just bought index funds and I had a barbell strategy. I have index funds from Vanguard over here, wealthfront, whatever. Super conservative, low fee and real estate. And then

over here, I have my really high, you know, highly variable startup investing. And then I was like, you know what? I think the market's really low. I cover technology companies all the time. Companies I pick seem to have done well over time. I'm going to jump in. So, I just, you know, earmarked a couple million bucks. And I'm now on this week and startups doing a J trade twice a week. I'm using the hashtag J trading. And people are like, oh my god, are you giving

investment advice? I'm like, no, I'm actually looking for investment advice. And I'm telling people like, okay, I'm buying stitch fix. My first trade was buying stitch fix. And I'm like, here's my thesis. I saw Bill Gurley buy a million shares. I know Bill Gurley. He's really smart. He's been with the company forever. Bill Gurley is buying a million shares. Sure, I'll buy my about five thousand shares. And then I was like, you know what? I think Disney is going to get to a billion subscribers.

I think that between Disney, who will lose ESPN plus, they're going to get to a billion subscribers. We've never seen a billion subscribers. That sounds to me a lot like an iPhone franchise. If they get to a billion subscribers pay a money, that's going to be like, that's going to turn Disney into like Apple, I think, in terms of revenue generation. Just a thesis I have. Tell me if you think I'm wrong because somebody's going to get to a billion subs.

And I don't think it's Netflix. I think it's like some, it's either Disney or HBO Max, you know, they're bundles or whatever. So I'm going to buy some Disney. Then I see Netflix screwing up again. And I'm like, Amazon is the seventh best. Amazon Prime is the seventh thing on, you know, Amazon's plate, you know, like AWS, you know, Amazon Prime, there's a million things they're working

on that are more important, probably than Prime. And they're better than Netflix. Huh. And then they just bought one medical and they got rid of, they're getting rid of Amazon basics so they can remove that attack vector for the, you know, regulators. Regulators doing everything right. And I've always wanted to own Amazon. So I bought some Amazon live on the air. And so I keep doing these like J trades and I am telling people, my plan is to hold these for 10 years. I'm going to make it public

every time I do a trade. I'll make a website eventually when I get to 10 or 20 trades and you can just watch it. And yeah, maybe I'll lose 25% of my money. Maybe I'll be, you know, 50% better than market. But I like learning different disciplines. So I think I'm going to try to get to 20 different stocks, maybe a million or two million dollars. And then I'm going to try to narrow down my 20 down to the seven best ideas. I don't know what you think of that strategy, but I always wanted

to learn how public market investing works. That's kind of cool. This week it starts every day. So I'll get all the. Do you do in the gauntlet? It's like being in the arena with it is the best way to do it. Funny story about Stitch Fix, by the way. I am. I pitched. So I was like considering going into like the crossover investing or hedge fund world before I like ended up, you know, building my own stuff. This is like early 2021. Stitch Fix was trading at like, oh god, no, like

55, 60 dollars a share. And the case study I had to do for this one hedge fund was Stitch Fix. And I had a week to like put together a whole thing on it. And I pitched Stitch Fix as a buy at like $55 a share. And you know, now it's sitting at six. And I got my blended price is six. But I didn't get the job needless to say. But every like maybe like once every three months, I send a text to the partner who I'm still close with from that firm with a screenshot of the

Stitch Fix price just saying like, it's a good thing you didn't hire me. Well, here it is. Just cratered. I mean, this is what I think is great about what you're doing is there's a concept of like super forecasting, not just forecasting, but it's a book super forecasting and understanding why you made a bet and why you didn't make a bet. And then doing a little debrief on those will make you better. So my thesis on investing is it's about process. So all I do is just try to

refine my process based on what's changed in the market and what I'm seeing. And then just being better myself. And so I have 11, I think 10 or 11 people on the investment team at launch now we do about 70 meetings a week, probably 50, 60 of them are introductory meetings. And we invest in two companies a week on average. And one of them tends to be a follow on one tends to be a new. So, you know, we're, you know, getting down from, you know, 10 or 20,000 pitches to us and

thousands of meetings, you know, down to 50 companies. Yeah, it's pretty crazy when you think about it. We know, and even then I have questions about the investments I'm making and really try to challenge myself. And I have been, you know, writing the book was one way for me to clarify my thinking and maybe have a better practice because people did tell me, Hey, dummy, this is wrong in the book or I think this is wrong. And then investing in public like I'm doing with J trading.

And then writing my deal memos, all these things kind of keep me accountable to myself and my own thinking when I make a bet. And I really like that. And any dude coach me on poker one time. And she's like, Okay, just we're going to play with the cards. I'm going to have you turn over your cards. Why are you playing 810? And I'm like, well, it's suited. She's like, yeah, but you're under the gun. And being suited gives you like a 4% advantage. And there are these other players coming

after you. If any, many hands are going to be better than 810. Are you going to defend this if somebody raises or if there's a re-raise or if somebody shoves it all in? I'm like, no, she's like, okay, so you're going to lose that blind. Why not take the three hands under the gun off? Those are the hands after the blinds. First people to act. They're at a disadvantage. And the last people that I can say, if you want to get cute and play a 10 suited when you're the button, okay, maybe

you only have two more people to act after you the small and the little blind. So maybe tighten your range and don't play out of position. And just like me, those little two adjustments, my game, all of a sudden I went from losing in, you know, let's say three out of four games and playing in these like underground or home games in LA, to winning three out of four. And I was like, wow, just that little tweak. And now everybody else is doing that. So then there's a whole

another series of things you have to figure out about the game. But just those two little tweaks changed my game forever. And I always wonder like when I'm investing, are there other little things I can do like that to just be a better investor? And I base all of my private market investing on the team, the product and the customers. Now you can become really inspired by a founder and they've been trained on how to be charismatic now. They've kind of unpacked what charisma is

and how to sort of fake it. So it's quite theatrical at times. But you can't fake a great product, you can't fake the light of customers. So I've now over time leaned into those two things. But in the beginning, I was just, you know, this guy Travis, I know him for a while and yeah, this Uber idea is great. Product is so signed, okay, the customers are over the moon about it. Oh, this guy calm, you know, Alex from calm. Oh, yeah, nobody will invest in this. It's a $4.5 million

valuation. They have $10,000 in revenue. And this guy created the million dollar homepage. But the product's beautiful. And I talked to the people running the UCLA meditation, mindfulness center. And they told me they trained Kobe Bryant, Chiquillo, Neil and Phil, on how the lakers were meditating. And that's when they went on the championships. And I was like, okay, I believe that meditation could be bigger than it is today when people go to like three

different places in LA to pay 20 bucks as a donation. And I made that bet on calm, which people always stupid bet. So I really looked at the customer base and the product now. But I've deprecated the charismatic founder because it's so easy to fake now. And so maybe someday, you'll be able to make a beautiful app just by talking to Dolly. You know, and Dolly, make me a gorgeous app that looks as good as Robin Hood. But for, you know, pick up basketball games. And

every apple looks stunningly beautiful. So then I'll have to. Yeah, but then Sam, Sam Altman will probably. So I don't know if we want to do that. Actually, I think they made that clear now. You own your stuff. And then somebody I think I got an email from Reid Hoffman that he was using Dolly to create NFTs. I thought that was a bad dream. Is this Reid? That's real. I was like, Reid, are you a burning man? Did somebody give you some plant medicine at burning and read? Are you guys?

Are you guys buying stock in snap at this cratered valuation? I just I have to ask because it's going to look at it. Tell me your. 40% today. What is the revenue? I would look at the revenue and then the price to sales ratio. And then I would look at user growth because if the users are still growing, and I don't know if they are or not, and the price to sales ratio is just collapsed, that means somebody could buy it. And I think Evan Spiegel is a

product genius. Like he truly is. If you think about the things Zuckerberg copied from him, a femoral messaging lenses, stories, I mean, and glasses. Yeah, revenue is still growing. What is the revenue? I got to understand the revenue growth. Revenue is like 4.5 billion. What's the market cap? Market cap is now at 16 billion. So they're trading at four times. Yep. And down, I mean, you know, it's down 4% today. Yeah, but their their user growth.

If you look at the five, I don't know the number, but it's like, you know, not huge. From the peak. And revenue is going to potentially get down. 87% from the peak. Yeah, but this. But if we go back, the last time they were $10, looks like 2020. Yeah. And they were trading in that, you know, $6, $4 to $10 range for many years. They kind of just roundtripped the, you know, the COVID roundtrip that a lot of people did. Yeah. Like Peloton did the same thing. It's like, it's kind of taking

that roundtrip. The next piece of data I would need to know to make a J trade here would be cash in the bank. How much cash do they have? And are they losing cash, etc? So if they're growing, and they're four times revenue, and they have, they're not losing money enough cash, this could be a non-consensus bet. They've got about, I think, $5 billion in cash. So this is what's amazing about these companies. If you took the $5 billion out of the $16 billion

market cap. Yeah. Right. So like if you were to buy the company for $16 billion right now, it would include the $5 billion in the treasure. So you paid $11 billion. $11 billion if they're making $4.5 billion in revenues, 2x, $2.5x, I guess, or somewhere around them. So they're trading at $2.5 times their top line. Now if they showed a 20% margin, that would be $900 million, $900 million into $11 billion, they'd be trading at like 11 times earnings. So if he would be well under 15.

So that's what I'm looking at. I'm trying to back into if they could, if they could sustain a 20% margin, if they cut a bunch of staff, they probably could. But I mean, it's kind of hard to make $4.5 billion in the advertising world. I bet you Microsoft wants to buy this. I could see Google buying it too. Yeah. I mean, just off into a snap trader. Should I just do a JTRI? Yeah. I know. I was going to say,

man, if you make this trade, you got to you got to cite your source. I, I got another one for you guys. What do you guys think of Buzzfeed? But okay, I talked about this on this week and start of. Buzzfeed is making 300 or 400 million a year on their run rate. They only have 200 million in cash last time I checked and they were trading at 300 to 80 mark. Okay, so Buzzfeed is a disaster. Their market cap is 250. I think they have 100 or 200 million in cash. They're losing like 50 or

100 million a quarter. So this has the risk of ruin. They could run out of money. Yeah. Yeah. That is the key issue here. So you don't want to drop, you don't want to catch the falling knife in the middle of your palm, right? And so this is going to get worse and worse and they'll get bought. But if you took out 100 million, you can't even take 100 million in cash because they're probably going to burn that. But their PE ratio is 3.6. So did they show a profit the last quarter? I thought

they were losing money or maybe they're losing money with stock compensation. So this is an unmitigated disaster. Think about it. This company was privately valued at $2.5 billion I think, or $3 billion. So it's 10% of that. You know, you'd be looking at is somebody going to buy this? Now what value and who's the buyer? I was talking Disney wanting to own this or whatever, but it would be more like my guy Jim Bankoff who bought Weblogs Inc for me would buy it, put it as part of

Vox or he could buy it and then put Vox into it. But yeah, I don't know who wants to buy this. Journalism is a terrible business. There's no path to viral growth here. Every time you grow, in order to grow their top line, they're going to have expense. So if you want to get more page views, you're going to have to hire more expensive entitled writers as part of the BuzzFeed Union. Fifth disaster of a business. Yeah, this could go to zero. So why would you put money into this as

opposed to SNAP, which is run by a product visionary, which has viral ability, right? So if we start comparing the two, it feels like I would much rather own SNAP or Peloton. Peloton is a love product with millions of subscribers. And yeah, I think I would even go Peloton above BuzzFeed. But I do like this like bottom feeding. I think it's kind of an interesting thing to do.

Especially right now. I mean, there's just like, it's just even just as a learning opportunity, as you said, it's like, you know, learning in public around these things that you're doing. It's a pretty cool time and opportunity to sit around and learn about these things,

just given how much stuff is pulled back. It's like pretty, pretty interesting. Although I still agree with you that like, if you're trying to just make money and if you want to like become worth, you know, $10 million in the long run, buying index funds, like Vanguard index funds at the prices that they're currently at, is probably your best bet. Just like, I would advise. I would advise. I would advise people to just get wealth front. I had shares in wealth front

as an advisor and it's really the best product out there. And you can just set on a dial one to 10. I put all my family members on it. They all love it. They're all like automatically setting like a $500 deposit or $1,000 deposit every month. And it's a much better strategy for people. Like because you don't have to do what we're doing here. Like not everybody is in the middle of the tech industry with a bunch of smart friends who are making bets all the time and who talk about tech

every day and who've been in the tech industry for 20 or 30 years. Like you have to do these things when you have an advantage. Now I have an advantage in private markets. I have an advantage at poker. I don't have an advantage at crypto. And I'm trying to gain an advantage in public markets. If I wanted to go, if I wanted to be in crypto, I would stop investing in everything else. And I would start a crypto startup and I would invest in crypto on the side. So that I was in the thick of it.

I'd have 10 crypto developers and architects working for me, telling me which projects we're coming. That's the only way I would be involved in is if I could have an edge. I only want to bet money on things where I have an edge. And the way I'm looking at the million or two million dollars I'm going to put into J trading is that's to get me the edge. That's my, that's my MBA. Cost of admission. That's me paying for an MBA. It's cost of admission. That's my training. Now

I can't imagine in 10 years I'll be down. And if I'm plus or minus 25% of the index, it has no impact on my life. So it really is me doing this as a sport and as an education. Much like if you bought, I don't know, if you bought a condo, you know, in San Diego, because you love going there on vacation and you put it in the Airbnb pool. If you plus or minus the indexes or you could have optimized the apartment money better for your condo. But if you got to use it and you love San Diego,

that's kind of how I'm looking at the stocks. It's entertaining for my audience. It's educational for me. Fuck it. I mean, yeah. And by the way, on wealthfront, shout out, wealthfront, because I think they're actually the sponsor for this episode. I mean, it's fucking great. Use the promo code. Even better. To get 10% to get your first 5,000 free. I'm hijacking your promo code. It's good. It's good. I love it.

duly brum. So do you read your own? What's that? Do you read your own ads on the show? Yeah. Yeah. I do. I have to read 10 ads after this for next week's show. Because I'm going to go. Oh, man. So I want to ask you before we lose you a bunch of, we sent out a tweet asking what was the people had. And like a round time. Yeah, a lot of good questions. I think one of the ones that kept coming up was like this whole thing of like starting businesses with friends.

And you know, the pluses and the minuses of doing that. And like you guys have obviously had, you know, an interesting, you know, conflict recently with with all in crew. And you know, I've built one of the most impressive franchises in the world within the podcasting space and something really durable and interesting. Can you just talk about, you know, what went wrong? Like what what are the lessons around, you know, around doing business with friends and what

you would advise young people that are going out and doing that? Yeah. I mean, I think it's great to start business with your friends and projects. I think you looking at all in, it's a very unique situation. You have four alphas who are at the top of their industries and who are the, you know, God kings of their realms. So it's kind of like game of thrones, you know, like I'm like, well,

I have dragons. And they're brothers like, well, I have all the money and I got the big city. And, you know, I'm protecting the north like these are four formidable individuals with opinions. And so, you know, Jamatha asked me to do, he said, hey, I want to do a podcast with you. I was like, all right, come on, this thing starts and I want to do a unique one. Then we brought the two

David's on and it clicked and it became magical. And I really enjoyed doing it. And that's another area where like I really focused on being instead of the host being like a really good moderator and challenging people, interrupting people, forcing them to explain the terms they're using. And, you know, and obviously I'm funny and I make a joke here and again. And so, you know, I'm the funniest friend of the group who likes to break chops. And, you know, the other guys are pretty

funny too on the margins. And so it's just got a great, you know, spirit to it. Then we're like, we should do an event. We should meet the fans. And we're getting contacted by all the, you know, media companies whenever you something breaks out like it did, it, you know, became like, you know, top 20 podcasts some weekends, you know, and we're regularly the top 30 episodes in the world. It's pretty nuts when you think about it. And so we got a lot of offers, but nobody can offer

us money that would change any of our lives. And so we were just declined all that. Nobody wanted to do ads. I would have, I was like, let me read two ads. I could get 50k per ad. It's 100k. It's 5 million a year. And I'm the one producing all of this. And, you know, this is all built off of my company. Like I came up with the name. I came up with the format. You know, I do all the editing. I mean, I do all the work basically. So then we did the event. And I said, listen,

with the event, are we all going to do the work? They're like, no, let's do the event, but you do all the work. And then free bird was like, I don't want you to get paid more money than me. And, you know, free bird was complaining constantly. Yada Yada. And I was like, okay, this is getting really annoying. Now I regret doing the all in summit. Now the all in summit then turns out, people lose their mind over it. It sells out. It makes a couple million bucks, you know, a couple

of a hundred thousand dollars in profit. It could have made millions in profit, but we gave have the tickets to the fans at a loss. Like we, but gift bag was $600. So we just spent all the money basically, like drunk and sell those on these parties. And it turned out to be amazing, obviously. So then there was this talk of like, hey, we'll make it into a media company. We'll do more of fans. Well, you know, build it up. I said, okay, great. We're going to do that. And we were

public about this on the show. Then I think I deserve just a fraction of more equity. And Chimoff said, hey, what what what do you think that is? I said, I don't know. How about like two extra points. So I'll get 31 points. You guys all get 23. I'll be the CEO. You guys show up. I'll do all the work. And I, you know, I have a 20 person team and half of them, you know, I've got people, vent people already. So when we did this event production, I took 20 people on my staff. And I put

them on this for the last two weeks. And you know, I had three or four people working on it. So I basically took my team off of investing to do this. So anyway, nothing like so then you have four different opinions of what we should do. Sax is like, let's just do the podcast every week. That's it. Chimoff has ambitions. I have ambitions. Freeberg has anxiety. The whole thing was just causing chaos. And then we just decided, fuck it. We'll just make it a podcast every week. No more

events. None of this bullshit. And we'll just own a 25% each. But you know, we were negotiating. And then everybody started losing their mind. And yeah, we'd band almost broke up. But we realized like the audience really, we all came to the same conclusion. One, we loved doing it together. Two, the audience loves it. And three, we think we're actually doing something important in the world. And that really that third part, I think, is the key for me. And I know it's the key for

sax, Chimoff and freeberg. I can speak for all of them that we think what has click with people is that we're having better conversations and more intellectually honest conversations and first principle discussions. And we disagree with each other. But we keep the podcast going and the friendships going for sax is like one of my best friends in the world. People think that we hate each other. We just, you know, have a difference of opinion about Trump versus Biden,

Republican tactics, you know, overturning Roe v Wade. But if you look at the majority of things, and actually this episode 88 that came out, I took the political discussion, which is very challenging because half the audience gets pissed off when we don't talk about January 6th. And the other half gets pissed off when we talk about Roe v Wade. So we're in this kind of like conundrum where, you know, people like stick to your lane, do markets, do startups, do tech, do science. But then,

you know, like we want to have discussions about other things too. And so we're intellectually curious. So I basically broke down very intentionally this week, instead of tribally talking about Biden versus Trump and DeSantis and all this bullshit. I just let's talk about first principles. What do we all agree on? Do we believe we should be physically conservative and that the government should stay out of our personal lives? Like, yes. Okay. So there's a starting point where that's

about 80% of political decisions, less government. You want to be gay, you want to be trans, you know, you want to have an abortion, you don't, like it should be all your decision. Okay, I'm going to say gun control. Do we do any of us have a position? What should the position be? Like, and then what this always breaks down is, well, how horrible is Trump? How how how scene now is Biden? How terrible is DeSantis? It all becomes tribal. And then you start like losing

the script. And so what I'm trying to do as the moderator is really get us to talk about the first principle stuff. And I think the podcast is really important. But it's I was going to put some more energy into the events and podcasts like I had I had an idea for another two or three podcasts that could have been offshoots of all in. But they don't want to make it into a business. So I'm just going to do those independently. So I'm launching two more podcasts. Oh, cool. In September,

one of them is going to be called Founder University. It's just going to be one time a week where we teach a founder scale that we're already teaching our three portfolio companies. But we're just going to make it into a podcast. So it's going to be very simple podcast format, 15 minute lesson on how to grow your podcast. And they got a second one that's going to be a roundtable format. But not with the original cast of besties. So think of it as like another superhero team.

Because we have all these people in our orbit who want to come on all in. They want to come on this week and start up. But this week and start up is about startups. It's not about, you know, crypto or politics or Roe v Wade. And then we have all these people who would love to sit in like Brad Gersner or, you know, Elon or whoever, you know, who have been on the pod. Dremon, you know, there's just this whole people in the orbit of all in and the orbit of this week and startups and

who are our other besties. But they can't be on this all in podcasts because we show up every week. So I'm going to do another roundtable where I'm the point guard again. I really like that position. And I'm really trying to be the best at it. You know, essentially what I do is I try to add a new skill and be really good at it. You know, I don't have to be the best, but 70, 80, 90 percent, you know, be in the top 10 percentile of any skill, which is what I'm trying to do with public marketing

investing and what I'm trying to do as a moderator. And you know, it's getting noticed. I got a bunch of TV deals in the works where people like, you're really good at moderating. You're not just a good guest. Would you like to do something on these other network streaming, whatever and what that look like? And so I'm considering other opportunities. And all in will just be, you know, this one little thing. I wanted to make all in into something bigger. But the boys and I decided we'll just

keep it one thing. What motivates you? Like you have so much on your plate. You have a lot of things going on. You have all these different businesses. You sound, you seem super curious still and excited about all this new stuff you're learning. Like are you financially motivated to do all this stuff? And you want to make, you know, billions of dollars? Are you? I've never been finding it. I've never,

I've always wanted to be a millionaire and like not have to worry about money. Like anybody probably wants, but I've never been like, I need this incremental, you know, amount of money. I am playing for fun and joy. I'm like the love of the game. And so when my friend Dave Goldberg died tragically, Goldie, who played poker with ever us every week, I really reassessed my life a bit. And then when Tony Shade died two years ago, the day after my birthday, two months ago,

on November 27th, that was a real gut punch for me as well. Because we were good friends and played poker and I would stay with him. I was a vagus and stuff like that. And that was very tragic as well. And I just reassessed like, okay, let's just, what do I like doing? And I like talking and doing podcasts and I like performing, I like writing, I like investing in companies, I like building products. And it turned out I also liked doing certain activities, which I never really did because

I was so busy working. So I turned out, I like skiing a lot. I was talking to a friend and everything I described to them of what I like doing was in service of other people. And he's like, you realize like none of this is like for you and your joy. And I was like, yeah, that's kind of interesting. I do the pod. I get joy out of it, but really a lot of other people get joy out of it. It keeps people employed. I do investing. I do get joy out of it. I love building companies,

but it's for helping other people. And my friend was like, what do you actually really love yourself? And I was like, I love hanging out with my friends playing cards. I love skiing. And so last year, I bought a ski house and I skied 40 days, which was more than I skied in the last 10 years. And I was like, you know, I kind of am interested in this mountain biking thing. So I just bought like a $9,000 specialized nice e bike. And I went four times this last two weeks up here in Tahoe. And

it's incredible. And so I'm trying to hook you up with some mountain biking gear. If you're if you're interested, I'm on the board of Fox Racing, which is like one of the biggest mountain biking brands. I just bought their knee pads and gloves, I think. Oh man, I can hook you up if you want anything. No, no, I don't take freebies. I always like to buy stuff. I hate taking things. You can pay. You can pay for all just getting. Yeah. No, I just I like to pay. But anyway,

so that's really what motivates me. I really like, I've come to the conclusion that at the end of your life, it's a bunch of memories of like these peak experiences, victories, failures, whatever. And as best I can tell, that's what makes a good life is like these collections of these peak experiences that you laugh about when you're friends. And so I'm just trying to actually manufacture more of those incredible peak moments with my kids, with my wife, with my friends, with my business

colleagues. And just with everybody, you know, and I'm also trying to figure out like how to spend money to increase my joy, which has a porcuit from Brooklyn who grew up Irish Catholic. It's like really against everything I'm about. So like buying this $9,000 specialized bike or buying the ski house that I bought like, if it was five years ago or six years ago, I would have suffered immensely about making those purchases, even though I could easily afford them. And now I don't

suffer over them. Like I just told my chief of staff, go test drive the piece, he's a jock. And I was like, just test drive all the bikes, whatever the best one is, figure out the consensus and just bring it up to the ski house and find me an instructor. And boom, here I am. I got instructor. I'm going to start going on lessons. I did a couple of rides on my own. And you know, great, and talk about peak experiences. I came around to turn on a trail. I went out with my friend Ryan

Block, who was one of the editors. And I consider my co-founder of Engaget. And I, he took down this great trail in Tahoe. I decided I'd go do the same trail. I go out at twilight. I come around to turn 20 feet in front of me, a giant mountain line. I slam on the brakes. Mountain line turns around, stairs at me for five seconds. And then walks off and differently. Oh my god. I can tell you there's one of the peak experiences of my life.

Peak experiences in the, I've had some scary experiences in my life, you know, have been grown up in Brooklyn and been in some pretty crazy bar fights and whatnot, scary moments. This was probably top three most terrifying moments of my life. The blood came out of my body to have a predator stare at you for five seconds. It's like nothing I've experienced in my life. It never had a predator stare at me for five seconds. And I, it was beautiful and gave me the,

you know, brain chemistry rush. I don't know what got released in my brain. But I just thought this is how it ends. I'm literally going to spend my final minute or two on the planet. My final moments will be trying to survive and attack from a mountain lion. It was, you know, pretty terrifying, exhilarating and freeing in many ways. Because I've been contemplating my own mortality because I'm 51 now and two of my friends died in their 40s,

tragically. And you know, you start thinking about like, what do I want to get out of the last 20, 30 minutes days, years, weeks, quarters. I don't know what I got left. Now when you're 20 or 30, you're kind of on adrenaline. You're not thinking about that. But when you get to 51 and you start to have a couple of your friends ago, then you're like, ah, and I will do your children. I got to squeeze some juice out of every single orange. And I got to enjoy every sandwich, like every sandwich

counts. Like just every bite you take just enjoy it. It's a blessing. It's a mitzvah. How old are your children, Jason? So you have two six year old twins and a 12 year old. All girls. And it is the greatest joy and most fun you can imagine. So when I'm up here in Tahoe, I, you know, I get this window where I take them for every day or almost every day. I don't let people book stuff on my calendar. And I've been just taking them to the beach or on a hike or for a walk to dinner and

ice cream. I give my wife a little time off so she can work on some of her projects. And it's just been incredible bonding. It's like been this like dream summer that I never had as a kid. My parents had to work because we were barely middle class and always behind the April in terms of finances. So you know, my summer was leave the house at 8 a.m. You're not allowed to come back to a five or six. Keep yourself entertained on the streets of Brooklyn or whatever other borrow you can get to

on $20 with your true brothers. So we had a pretty rocked as childhood. But that's just been delightful. I'm like, I'm living some crazy fantasy where I'm by a lake. And then getting ice cream cones and walking our bulldogs with these three wonderful children who are laughing and joyful and falling asleep in the car with ice cream on their shirts. I have felt that for sure. I know I wanted this childhood. But I'm living it now. So it's great. I have a two-month-old

our first little boy. I have felt that exact thing of like every morning. It gets even more interesting. And from like nine to 10, we got on a walk in the neighborhood. My wife, our son Roman and I was walking around one day and I was like, it was sunny. It was like 75 degrees and I was just like this holy shit. You know, life doesn't get much better than this moment right here. You know, and you don't need more money. You don't need anything else. It's like in that moment

everything is enough. It's a pretty amazing. And it gets more interesting. And it's a boy. So yeah, I grew up with brother. So it's I understand the fun of that. What's great is you just sort of click into this wonderful, you click into this wonderful moment where you get to relive your childhood and experience everything again. So my wife's like, oh, this house I bought, this was like the reason I bought it. I'm in a movie theater right now. And like I love movies and I take or

was taking my 12 year old to the movies every Friday. It was kind of our tradition. I've just been a fan of cinema my whole life. I wanted to be a director or run a movie studio in another life. And I was like, you know, I said, can you pick a movie tonight? I'm like, yeah, I'm just going through all the great movies of my child or whatever. And I was like, what about Bob? You know, I love like that's an incredible movie or anything Bill Murray's in. It's great. So now my kids are old

enough and we watch what about Bob? If you haven't seen that, it's like the perfect summer movie because it takes place on an island in the summer. Bill Murray, Richard Dryas, hilarious. And so you get to experience all those things again. So with your two-year-old, you'll at some point be like, hey, you want to read the Hobbit or watch Lord of the Rings or can I introduce you to Star Wars or Jurassic Park. And all of a sudden you just get this incredible orc, can I teach

you how to ride a bike? Or, you know, let me teach you how to cook. And you know, all these things start happening that you get to relive for yourself. And it's like something very primal and joyful about it. I'm enjoying a tremendous one. Be present as much as you can. I think that's a great place to wrap up. You've been so, so generous with your time. Of course. Really, really appreciate it. And a lot to chew on and a lot to a lot to continue learning. I mean, if anything,

have fun folks, start a card and have fun. Yeah. Yeah. I mean, just keep being curious, man. Your curiosity really shines through. So super excited to see all the stuff that you continue to build next. And we'll be following along with whatever is. So thank you so much. Appreciate it. Thanks, boys. Thanks, boys. Let's do it again in here. Thanks so much for listening to today's episode. If you have any questions that you want

featured in a future episode, email us at high at trwih.com. Leave us a review at Apple or Spotify to help us grow the reach of this podcast. Until next time, we will see you soon.