How To Pick Startup Winners With Jason Calacanis

0:00only 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 frisk and 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 two or ask if you can do one i have people do that all the time to me like hey your minimum is 4k on this deal because it's 250 slots that's a million dollar allocation can i do one and i'm like sure do one i've had

0:31people ask to put 500 and they're in credit investors i'm 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 [Music] did you know that one of the top reasons startups fail is bad hiring decisions people can be unpredictable and developers can be unpredictable as well let lemon.io take care of hiring your software engineers why lemon.io they test and interview every single specialist before offering them to clients unlike many other sites offering remote software developers lemon.io is sure they offer you experienced and verified devs it's like hiring someone after your best friend's recommendation but even

1:21better why because even the best friend can't offer you a replacement of the candidate in 48 hours or less if something goes wrong but lemon.io can you'll be working with hand-picked software engineers from europe they'll be a part of your team lemon.io staff never intrudes on your communications unless you ask them to minimum bureaucracy maximum efficiency that's a win-win combination for developers and clients so hire high quality verified vetted engineers from europe with lemon.io and be stronger than 90 of startups on the market go to lemon.io room and get 15 off for the first four weeks get there before your competitors will check out lemon.io today

2:11jump right in man cold open cold open uh i do want to i do want to start there actually it was actually what i wanted to ask about because about about a month ago or so you tweeted something out you said um vcs having a liquidity path for crypto with retail investors is problematic um you know and you talked about what you talked about on the odd lot podcast like this general idea that vcs were pouring money into uh you know these liquid tokens or semi-liquid tokens um and then basically dumping that um very very shortly on retail at these massive markups and then retail was left holding the bag um i kind of

2:46pushed back because i was under the impression that a lot of these vcs were being asked to sign up to like you know two-year vesting schedules or something on these and maybe it's just like my own naivete but i'm curious to just like get your general perspective on that as a starting point of like what are you seeing out there that's happening um you know and what do you see happening in terms of the regulatory and legal landscape around that next yeah so uh 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

3:17law firm or any one coin so 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've been talking about crypto uh for over 10 years on the podcast i was one of the first people to cover bitcoin i booked bitcoin at like two or three dollars and then again at 100 and 200 so i've been og crypto for a long time um i understand the space i'm not a coder or a developer but um you know i i generally understand what's going on here and i've invested in 350 companies so that's sort of where i'm coming from

3:46and i also run it's the largest syndicate in the world with 11 000 accredited investors and i've done over 260 deals so i understand the the nuances and i've learned this you know through a lot of hard work how to deal with you know basically managing a large group of investors and 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 a basic uh license like a driver's license if you think about like that become accredited so i don't think accredited should be based or accredited accreditation in the united

4:25states should not be based on your net worth because you could be uh a trust fund kid and be considered qualified you know 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 buddy's startup that he's creating but i'm allowed to go invest in like a triple x levered you know mortgage etn

5:00through my brokerage account with no questions asked 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 it's 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

5:29know all the 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 the money to charity and that would be a perfect proxy for people um and i would do it for free uh 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 uh 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's scuba

6:05diving i don't know if you guys are paddy certified i'm paddy 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 it might 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 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 you know have you seen matt levine's i'm an idiot test that he's written about in

6:34the past no not levine the bloomberg writer his like his idea around accreditation is uh basically you should just have to every 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 just sign it and it's like same general principle you're like okay you're gonna invest in something speculative you just have to say i know i'm being an idiot i'm probably gonna lose all my money on this totally fine it's tongue-in-cheek but you know to be honest i think that's sub-optimal i know some people are radical it's your money

7:05do 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 um you know people could lose a lot of money very fast and they 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 but so i just want people to understand where i'm

7:32coming 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 um you know same could be said for some startups as well right 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 dollars on an idea and so what's happened in crypto is i think a lot of vcs and investors

8:08um 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 convince 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 clearer but i think the sec's position 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

8:43time 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 uh reached product market fit but you wouldn't take these companies public that have product don't have product market fit and in fact you told uber and airbnb to stay private until year 10 so that they were really ready to go public so they basically figured out a public market

9:27if you want to call it a strategy some might call it a scheme some might call it grift you know depending on how cynical 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 it coming uh and those people have a free option now they they made these bets there was a

10:03murky 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 a hundred 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'd 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

10:40going 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 com.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

11:10participating 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 you know 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 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

11:45and i mean countless lawsuits hundreds of lawsuits because i saw this with the dot-com era i'm i'm not some like uh you know clairvoyant here predicting the future you know i'm not nostradamus here i've seen markets collapse stockholm era there were lawsuits for years what's your what's your optimistic take you know five ten years from now for web three i think you've you've spoken a lot about you know the faults of web3 and there's tons but i'm curious you know what what does web3 look like in five to ten years all right so web3 is a collection of assets right people include blockchain in there they include smart contracts in

12:23there distributed computing is in there permissionless you know trustless serverless peer-to-peer all that is part of this um you know technology stack so you're really asking like what are what 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 uh or maybe three that i think could have legs uh i think nfts uh 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

13:01membership or whatever it was and under some sort of smart contract rules i if i paid twenty five thousand dollars to become part of my local golf club or five thousand dollars to be part of sole house i would have the right to sell it to somebody else um and i could get back up to 100 of my original investment then 50 of any gain and then the solo 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

13:32over 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 we invested in a company and we bought two nfts from afterparty 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 like i'm a rich it's almost like i'm an original patron of um sundance or an original patron of coachella like if you're a sundance patron which is a non-profit the film

14:04institute 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 did you know that one of the top reasons startups fail is bad hiring decisions people can be unpredictable and developers can be unpredictable as well let lemon.io take care of hiring your software engineers why lemon.io they test an interview every single specialist before offering them to clients unlike many other sites offering remote software developers lemon.io is sure they offer you experienced and verified devs it's like hiring someone after your best friend's recommendation but even better why because even the best friend can't offer

14:49you a replacement of the candidate in 48 hours or less if something goes wrong but lemon.io can you'll be working with hand-picked software engineers from europe they'll be a part of your team lemon.io staff never intrudes on your communications unless you ask them to minimum bureaucracy maximum efficiency that's a win-win combination for developers and clients so hire high quality verified vetted engineers from europe with lemon.io and be stronger than 90 of startups on the market go to lemon.io room and get 15 off for the first four weeks get there before your competitors will check out lemon.io today all right and so the other thing i find pretty

15:36interesting is like it's dowse 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 picasa which takes a home we'll turn it into eight shares we could all buy this home in tuscany they would provide uh all of the uh furnishings they would manage when we each got our weeks and if we all both wanted christmas they kind of have an algorithm to manage that so it's fair for the premium weeks yada yada they charge you an expense they get a little

16:16bit of a vig but you actually own it right so now imagine that same scenario but without a company we buy this same beautiful you know farm in tuscany and we each own you know roughly 33 shares in a hundred unit llc each two shares in the yellows in this dow equal a week at the place and each one has a cost of i don't know two thousand dollars in maintenance a year right 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 writer refusal on

16:53those shares or you get first friday refusal over 10 days for half of my share so if i want to sell before i have to share you four other ones whatever we come up with as our concept here i mean 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 you know a farm in italy it could also be for us to buy the knicks it could be also for us to buy twitter it could be for us to um save the wells or buy acreage to you

17:28know deal with the rain forest or a non-profit 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 non-profit 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 um you know everybody knows that it's

18:05slow and it's never going to get super fast at least not when compared to you know uh 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 uh 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 uh you know are buying into crypto would very much like to have their trans their transaction reversed if it was hacked um now other people see that as a

18:46feature like haha you made a mistake you 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 the stuff is overblown and i think the main problem as an 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

19:17but a lot of them um 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 the tragedy of this just like the dot com era a lot of the people who we were building the dot com 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 that was what it was about you know and to be able to communicate with

19:47people across borders and then people came in and said hey this is a quick way to take a company public and secure a bag so i think that's um what's happened to crypto now i i was waiting for this crash a lot of people i know encrypted were waiting for this crash so hopefully it flushes out 70 80 percent 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 uh i like

20:13uh prediction markets uh and stuff like that so i do think there are some wagering and interesting things there you and i want to bet on the i don't know a knicks 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 um 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

20:41and 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 bet and it doesn't cost us anything right one thing that's problematic why isn't it all free like weren't we supposed to save money on this like the gas phase and stuff like that is just ridiculous like if you're gonna make this competitive it should be ten times cheaper than whatever the best deal is so if stripes three percent this thing's gotta be like point three thirty basis points like it's gotta be really competitive with what's out there and it should be but

21:13again back to securing 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 aficionados out there that say oh yeah you lost your money you got fraud you know scammed your platform got hacked whatever like oh too bad you know that sort of the the price you pay and that's that's how it works you know not your keys not your not your coins um and i just like why has that turned out to be true huh yeah but but like my thing that i keep

21:46coming back to on all of this is that um centralization is good in times of crisis and like i think that across decision-making authority too and so when you talk about dows like i think a lot of the use cases you talked about are interesting in the in the context of a dao where you have like um you know governance across a bunch of people for like you know um investing behind causes and uh or 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 dow and community governance of everything and

22:14my whole thing with that is like that sounds fine when everything is up and to the right and times are good but when [ __ ] 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 uh you know distributed decision making uh in times of war default decentralized and you know default immutable default you know smart contracts probably not what most use cases uh should be so i think there was this like drunken you know uh fever about these coins because they kept going up to the right

22:51so 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 uh a crypto version of airbnb where you know there is no central authority you know making sure your house doesn't get robbed or trashed if that would be better or not because you would take out all those fees uh you know happy to see somebody try uh 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

23:28actually don't think they work better i don't think most consumers would pick the decentralized crypto version over the centralized trusted brand people are underestimating central i also think we saw a lot of bad actors in the nft space so that the 10 000 the 10 000 pfp collection cookie cutter um that that cycle from 2021 to early 2022 and just that rinse and repeat that people were doing where nfts like we often forget but nfts don't actually need a you don't need to sell nfts at all so for example i'm happy to see a lot of freedom mint nft projects take off like the 100 thieves did a project where you know

24:14they're a popular uh gaming community you know they had seven hundred thousand people meant for free these nfts uh 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 uh so i'm excited to see more freedom mint uh into 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 yeah you could go make eight i mean

24:44there 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 uh it was probably the best way to make like five million dollars style you wanna tell that story we had that we were you wanna tell that story about our friends yeah i mean we we had yeah we had a group of friends who basically had this idea where it was like um hey let's go we have large platforms on 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

25:17this cool universe and we'll go like create a project and we originally like greg and i originally started working 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 uh our friends that were kind of you know wanting to do it were really just like there was no road map it was just like makeup here's how much we're gonna make in the mint and then let's move on and so greg and i both like pulled the plug on it and just

25:44walked 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 um and honestly probably likely that like two years from now a lot of these people get sued or that yes it 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

26:08million dollars in like a month um if you had low morals i think any time um you i've been introduced to some sort of investing space um you know if you look at the tactics being used with the new entrants that can tell you a lot so if you come to a poker game somebody's a fish you're gonna get invited to a lot of poker games all of a sudden you're like wow i'm so popular i got invited since one poker game and then two people 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

26:36getting invited to all these games like wow i'm super popular and i was like no it's just bad at poker now these are 200 poker games it was like nothing so people were just like oh he's a whale he's 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 tournament for 35 bucks and i know i'm going to lose but i'll learn great um

27:03the 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 could literally learn for a thousandth of that equally well so um then you look at angel investing people want an angel invested 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's gonna be four or five thousand dollars so it's nothing it's

27:30literally 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 like 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 frisk and 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 two or ask if you can do one i have people do that all the

28:02time to me like hey your minimum is 4k on this deal because it's 250 slots that's a million dollar allocation can i do one and i'm like sure do one i've had people ask to put 500 and they're in credit investors i'm 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 now let's look at crypto so in poker community like they're trying to get more fishes and whales at the game and you know what i saw crypto very similar have fun being poor you don't get it okay boomer not gonna make it gonna make it you know

28:33all this peer pressure i would say something like you know listen bitcoin is a great technology it's been proven uh pretty robustly over a decade but it will be replaced by a better technology um all technology is replaced eventually by a better technology and man the bitcoin maximalists 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 wasn't 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 uh please name another you know

29:09and like it's pretty hard to name right uh 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't anticipate here a black swan event all kinds of things can happen right these things do happen and oh you don't

29:41get it you're you're being taught you're you're have fun bluetooth and i'm like listen 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 two hundred now i lost the three dollar shares because i didn't have the keys and the website got compromised you know but i mean it's just like being honest about upside and downside around these things and people during times of uh overwhelming optimism

30:13no 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 um 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 number numbers go up right it's like the crypto saying numbers only go up um and that's i mean it's just an important thing right like you need to envision the

30:39possibility of failure and then joe from odd lots said like this is the stupidest prediction ever and and then david sacks back in the day and when i had written this in like i think it was december of 2018 and i said listen here's your captain speaking things can get a little rough here i've never seen a bull market this long just make sure that you have a path to profitability you got some good cash in the account and you're raising money at the top of the market all pretty you know in hindsight great advice but it's it's ba it's i don't give myself any credit for it it's kind of simple

31:05advice right um kind of 101 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 100 million giving a hundred million dollar valuation to a company with no revenue and you know four thousand vcs using the product and you're like okay i think clubhouse is cool too but there's four thousand 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 4 billion it's like really i

31:36does this make any sense and it obviously did not make any sense and in hindsight you know they're going to have to go down to a 250 million valuation and build back up but they did all the bags 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

32:04funds endowments insurance companies etc 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

32:36underwater or investing you know the one caveat garbage market is these are the most sophisticated investors in the world so you know i i look at the stack and i say how sophisticated how long have these people been doing it like these lps have these funds venture is but you know five percent or less in some cases it's ballooned up to 20 25 when venture is you know got big markups it can get bigger but intentionally they put it at five percent sometimes ten percent depending on the aggressiveness of the fund and uh they kind of know what they're buying into they know it's cyclical they

33:06know there's boom bust cycles they know they can you know have a 20x fund and they could lose 50 percent of the fund and 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 like i 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

33:41result 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 a hundred as 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 um 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 d.a uh is a stepping stone it's prestigious well what's the most prestigious thing

34:14you 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 uh 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 who's going to be like what seven people in my jurisdiction got screwed by you know bit connect or you know whatever well connect yeah okay so we're going to come at you and we're not going to stop and if i get that pelt and put it on my wall i'm going to be able

34:49to say when i run for governor yeah and you know all your friends who lost money in crypto i was able to prosecute 17 people just like you know somebody else running forever 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 now and it could be unfair too they went after people on wall street after uh you know henry blodgett famously was banned from ever you know working in securities for life because of a couple of emails

35:20you know where he was like yeah i think this company's a dog but we have a buy rating on it and you know uh i don't understand you know like i was like okay you know that's kind of the modern day uh and henry's a delightful great person probably learned from that i'm sure i'm sure he did uh and i'm fond of henry as a writer and thinker but is he the head of insider yeah which used to be silicon alley insider and you offered me five percent of it because i had silicone reporter magazine and i said no you know just keep it that was a stupid mistake

35:50on my part it probably in a couple million bucks do you on all of this stuff i there's this one area i've been wanting to ask someone about i feel like you're a good person to opine on it um this whole like 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 i'll read it and they'll do like a bowl case on some

36:20crypto 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 then people that go and 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 millions you know twitter

36:52newsletter or whatever um i mean that to me is like an area that regulators need to look at i think a lot of people are probably deleting a lot of posts right now a lot of people deleting it 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 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 bender they

37:18could be incompetent like really you know uh 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 sh just so you understand uh and i frame it as that because we are making bets here and so you know i just started j trading uh you know i 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 equity space

37:47i've always just bought index funds and i had a barbell strategy i have index funds from vanguard over here wealth front whatever super conservative low fee and real estate and then over here i have my really high um 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 picked 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 weekend startups doing a j trade uh twice a week i'm using the hashtag j

38:20trading um and people are like oh my god are you giving investment advice i'm like no i'm actually looking for investment advice um and i'm telling people like okay i'm buying stitch fix like 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's buying a million shares sure i'll buy my about 5000 shares um then i was like you know what i think disney is going to get to a billion subscribers i think that between disney hulu espn plus they're going to

38:54get 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 paying 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 gonna buy some disney then i see netflix screwing up again and i'm like amazon is the seventh

39:24best uh 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 um the um 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'm telling people my plan is to hold these

40:00for 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 percent 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 2 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

40:27investing works that's kind of cool this week in startups every day so i'll get all this stuff 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 um i pitched uh so i was like considering going uh 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 a share and uh the case study i had to do for this one hedge fund was uh stitch

40:57fix 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 dollars a share and you know now it's sitting at six and i gotta return my blender but i didn't didn't get the job uh needless to say but uh 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 wow but here it is just cratered i mean this is what i think is great about what

41:29you're doing is um there's a concept of like super forecasting not just forecasting but there'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

42:01and 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 wow um yeah it's pretty crazy when you think about it uh you 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

42:30dummy this is wrong in the book or i think this is wrong um and then um 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 liked that and uh annie duke coached me on poker one time and uh she's like okay just we're gonna play with the cards uh i'm gonna have you turn over your cards why are you playing a10 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 four

43:00percent advantage uh and there are these other players coming after you if any many hands are going to be better than a10 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 then the last people died and said 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

43:29you the small and the little blind so maybe tighten your range and don't play out of position and just like made 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 uh 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 nother 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

43:57are 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're they've been trained on how to be charismatic now they've kind of unpacked what charisma is uh 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 delighted customers so i've now over time leaned into those two things but in the beginning i was just you know well this guy travis i know him for a

44:28while and yeah this uber idea is great product is so signed okay the customers are over the moon about it um oh this guy com you know alex from com oh yeah nobody will invest in this it's a four and a half million dollar evaluation they have ten thousand dollars in revenue and this guy created the million dollar home page but the product's beautiful and i talked to the people running the ucla meditation uh mindfulness center and they told me they trained kobe bryant shaquille o'neal and phil um on how to when the lakers were meditating and that's when they won all the championships and i was like okay i

45:05believe 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 com which people that was stupid that so i you know i really looked at the customer base and the product now and but i've i've deprecated the charismatic founder because it's so easy to fake now right and so and maybe someday you'll be able to make a beautiful app just by talking to dolly you know and you're like dolly make me a gorgeous app that looks as good as robin hood but for you know uh pick up basketball games and

45:37every app will look stunningly beautiful uh so then i'll have yeah but then sam sam altman will own it so i don't know if we want to do that actually i think yeah they made that clear now you own your stuff and then somebody i i think i got an email from reid hoffman that he was using dolly to create nfts and i'm like rita you thought that was a bad dream is this read that's real i was like reed are you a burning man did somebody give you some plant medicine at burning man are you guys buying stock um in snap at this cratered valuation i just i have to

46:14ask because it's going to look good tell me your investment 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 of 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 ephemeral messaging lenses stories i mean and glasses yeah revenue's still growing user base is still growing i gotta understand the revenue growth

46:55revenue is like 4.5 billion um what's the market cap market cap is now at let's see 16 billion so they're trading at four times yep and down i mean you know it's down four yeah but they're they're user growth if you look at the five their user growth is i don't know the number but it's like you know not huge cheek and revenue is going to potentially go down 87 from the peak yeah but this but if we go back the last time they were ten dollars looks like 2020 and they were trading in that you know six uh four dollars to ten dollar range for many years

47:44it kind of just round tripped the you know the covid round trip that a lot of people did you know like peloton did the same thing it's like it's kind of taking that round trip 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 um and they have they're not losing money enough cash this could be a non-consensus bet they've got about i think five billion in cash see this is what's amazing about these

48:19companies if you took the 5 billion out of the 16 billion market cap yeah right so like if if you were to buy the company for 16 billion right now it would include the 5 billion in the treasury so you paid 11 billion 11 billion if they're making four and a half times four and a half billion in revenue is 2x 2.5 x i guess or somewhere around yeah so they're trading at two and a half times their uh 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

48:51earnings so pe 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 four and a half billion dollars in the advertising world i bet you microsoft wants to buy this i could see google buying it too yeah kind of charging yourself into a snap trade here should i just do a j trip yeah i know i was going to say man if you make this trade you gotta you got to cite your source

49:16i got another one for you guys what do you guys think of buzzfeed but okay i talked about this on this week in startups buzzfeed is making three or four hundred million a year on their run rate they only have 200 million in cash last time i checked and they were trading at um 300 280 markets 250 now okay so buzzfeed is um 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 that is the key issue here so you don't

49:56want to drop you don't want to catch the falling knife in the middle of your palm right and so um this is going to get worse and worse and they'll get bought but if you took out a hundred million you can't even take the hundred million cash because they're probably gonna burn that but their pa 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 two and a half billion i think or three million so it's 10 of that you

50:29know you'd you'd be looking at is somebody going to buy this now what value and who's the buyer there was talk of disney wanting to own this or whatever but it would be more like my guy jim bank off who bought web blogs 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

50:58get more paid views you're going to have to hire more expensive entitled writers as part of the buzzfeed union it's a disaster of a business um 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 um and yeah i i think i would even go peloton above buzzfeed but i do like this like bottom feeding i think it's kind of an

51:32interesting 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 um 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 dollars in the long run buying index funds uh like vanguard index funds at the prices that they're currently at

52:04is probably your best bet just like dollar cost average into index funds i would advise people to just get wealthfront i had shares in wealthfront as an advisor and it's really the best product out there and you can just set on a dial one to ten i put all my family members on it they all love it they're all like automatically setting like a 500 deposit or a thousand dollar 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

52:34making bets all the time and who talk about tech every day and have 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 of crypto and i'm trying to gain an advantage in public markets um 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

53:0210 crypto developers and architects working for me telling me which projects were 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 jay trading is that's to get me the edge that's my that's my mba 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

53:31is me doing this as a sport and it's 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 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 [ __ ] it i'm in yeah and by the way on wealthfront shout out wealthfront because i think they're actually the

54:01sponsor for this episode uh i mean it's [ __ ] great use the promo code to get ten percent get your first five thousand free i'm hijacking your uh promo code that's good it's good love it dueling problem so do you read your own yeah what's that do you read your own ads on the show yeah yeah i do the ad reads i have to read tennis after this for next week's show because i'm gonna oh man um so i want to ask you before we lose you um a bunch of we we sent out a tweet asking questions juicy questions yeah a lot of good questions i think one

54:33of the ones that kept coming up was like this whole thing of like starting businesses with friends and you know the the pluses and the minuses of doing that and like you guys have obviously had uh you know an interesting um you know conflict recently with with the all-in crew and um you know have 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 um you know what what went wrong like what what are the lessons around um you know around doing business with friends and and what you would advise young people that are going

55:02out and doing that yeah i mean i think it's great to start business with your friends and projects um i think you looking at all in it's a very unique situation you have four alphas uh who are at the top of their industries uh 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 the brother's like well i have all the money and i got the big city and you know ah i'm protecting the north like these are four formidable individuals with opinions and so you know chamoth asked me to do he said hey

55:35i want to do a podcast with you i was like all right come on the swing starts and i want to do a unique one then we brought the two davids on and it clicked and it became magical um 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 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

56:03pretty funny too on the margins and so it's just got a great you know spirit to it then uh 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 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 um 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

56:33nobody wanted to do ads i would 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 uh 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 um 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 freebird was like

57:00i don't want you to get paid more money than me and you know freebird was complaining constantly yadda yadda um and i was like okay this is getting really annoying now i regret doing the all-in summit now the oil and summit then turns out people lose their mind over it it sells out it makes a couple million bucks you know a couple hundred thousand dollars in profit it could have made millions in profit but we gave half the tickets to the fans at a loss like we the gift bag was 600 so we just spent all the money basically like drunken sailors on these parties and it turned out to be amazing

57:27obviously um so then there was this talk of like hey we'll make it into a media company we'll do more events we'll you know build it up i said okay great if we're gonna do that and we were public about this on the show um then i think i deserve just a fraction of more equity and chamath said hey what what do you think that is i said i don't know how about like two extra points uh 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

57:54and half of them you know i've got people event 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 uh 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 chamav has ambitions i have ambitions freeberg has anxiety the whole thing was just causing chaos and then we just decided [ __ ] it we'll just make it

58:22a podcast every week no more events none of this [ __ ] and we'll just own it 25 each but you know we were negotiating and then everybody started losing their mind and uh you know band almost broke up but we realized like the audience really we we all came to the same conclusion one we love doing it together two the audience loves it and three we think we're actually doing something important in the world um and that really that third part i think is the key for me and i know it's the key uh for saks chamoth and friedberg i can speak for all of them that

58:53we think what has clicked 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 fr 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

59:34and 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 um intentionally this week instead of tribally talking about biden versus trump and desantis and all this [ __ ] i just let's talk about first principles like what do we all agree on do we believe we should be fiscally conservative and that the government should stay out of our

1:00:11personal lives like yes okay so there's a starting point where that's about 80 percent 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 gun control do we do any of us have a position what should the position be like and then what when this always breaks down is well how horrible is trump how tara how senile is biden how terrible is the sanchez it all becomes tribal and then you start like losing the script and so what i'm trying to do as the moderator

1:00:45uh is really get us to talk about the first principle stuff and i think the podcast is really important um 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 um oh cool in september one of them's gonna be called foundry university it's gonna be one time a week where we teach a founder scale that we're already teaching our three

1:01:12portfolio 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 i 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 um because we have all these people in our orbit who want to come on all in they want to come on this week in startups but this week in startups it's 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

1:01:42sit in like brad gerstner or you know elon or whoever you know who have been on the pod uh draymond you know there's just this whole people in the orbit of all in and the orbit of this week in startups and who are our other besties but they can't be on this all-in podcast because we show up every week so i'm going to do another round table where i'm the point guard again i really like that position and i'm really trying to be the best at it uh you know essentially what i do is i try to add a new skill and be really good at it you

1:02:11know i don't have to be the best but 70 80 90 you know be in the top 10 percentile of any skill which is what i'm trying to do a public market 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 would that look like and so i'm considering other opportunities and all in will just be you know this one little thing i wanted

1:02:38to make all in to something bigger but the boys uh 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 are you financially motivated to do all this stuff and you want to make you know billions of dollars or are you i've never been financially 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

1:03:07been like i need this incremental you know amount of money um i am playing for fun and joy um and like the love of the game and so when my friend dave goldberg died tragically goldie who would play poker with every else every week i really reassessed my life a bit and then when tony shea died two years ago the day after my birthday two months ago on november 27th uh that was a real gut punch for me as well um because we were good friends and played poker and i would stay with him and i was in vegas and stuff like that and that was very tragic as well and i just

1:03:41reassessed like okay let's just what do i like doing and uh i like talking and doing podcasting 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 liked skiing a lot i was talking to a friend and everything i described to them of what i liked 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

1:04:12i do the pod i get joy out of it but really a lot of other people get joy out of it keeps people employed i do investing i do get joy out of it i love building gummies 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 uh 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 interested in this mountain biking thing so i just

1:04:38bought like a thousand dollar 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 i can hook you up with some 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 uh brands i just bought their knee pads and gloves i think oh man i can hook you up if you want anything i don't know i don't take freebies i i always like to buy stuff i hate taking free you can pay you can pay full i'll just get you no i just i like

1:05:05to pay but anyway so that's really what motivates me um 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

1:05:41has a poor kid from brooklyn who grew up irish catholic was like really against everything i'm about so like buying this nine thousand dollar specialized bike um 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 um 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 rob 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

1:06:16uh find me an instructor and boom here i am i got an instructor i'm going to start going on lessons i did a couple of rides on my own and yeah great and talk about peak experiences i came around to turn on a trail that's i went out with my friend ryan block who was one of the editors uh and i consider my co-founder of engadget um and i he took down this like great trail in tahoe i decided i'll go do the same trail i go out at twilight i come around to turn 20 feet in front of me a giant mountain lion i slam on the brakes

1:06:44mountain lion turns around stares at me for five seconds and then walks off indifferently oh my god i can tell you it's one of the peak experiences of my life peak experience has been the i've had some scary experiences in my life uh you know having grown up in brooklyn and been in some pretty crazy bar fights and whatnot um scary moments um this was probably top three most terrorized terrifying moments of my life the the blood came out of my body to have a predator stare at you for five seconds is like nothing i've experienced in my life it never had a predator stare at me

1:07:16for 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 an attack from a mountain lion it was you know 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

1:08:0420 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 you start to have a couple of your friends go then you're like man how old are your children i gotta 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

1:08:35greatest 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 and i don't let people book stuff on my calendar and i've been just taking him 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

1:09:02and always behind the april in terms of finances so you know my summer was leave the house at 8 am you're not allowed to come back till 5 or 6 keep yourself entertained on the streets of brooklyn or whatever other borough you can get to on 20 with your true brother so we had a pretty raucous childhood um 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'm like i have to

1:09:36chocolate for sure i know i really wanted this childhood but i'm living it now so it's great i have a two-month-old um our first uh little boy have felt that exact thing of like every morning even more interesting yeah and from like nine to ten we go out on a walk in the neighborhood my wife um our son roman and i 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 [ __ ] you know life doesn't get much better than this moment right here um you know and you don't need more

1:10:08money you don't need any anything else it's like in that moment everything is enough um it's a pretty amazing and it gets more interesting it's a boy so yeah i haven't 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 um you click into this wonderful um moment where uh 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 i was taking my

1:10:4512 year old to the movies every friday it was kind of our tradition and 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 uh my wife was like can you pick a move tonight i'm like yeah i'm just going through all the great movies of my child whatever and i was like what about bob you know i love like that's an incredible movie or you know anything bill murray's in is great so now my kids are old enough and we watch what about bob if you haven't

1:11:10seen that it's like the perfect summer movie because it takes place on an island in the summer bill murray richard dreif is hilarious um and so you get to experience all those things again so with your two-year-old you'll at some point be like hey uh 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 or 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

1:11:40yourself and it's like something very primal and joyful about it i'm enjoying it tremendously absolutely be present as much as you can i think that's a great place to uh to wrap up you've been so so generous with your time of course i really really appreciate it and uh a lot to chew on and a lot too a lot to continue learning i mean if anything except 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 uh and we'll be following along with whatever it is so thank you so much appreciate it

1:12:13thanks boys thanks boys let's do it again 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 hi 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 see