I Asked a $450M VC Where to Invest in 2026

could only lose three million bucks i could gain three hundred million bucks i feel like i could rule where i know i could be what i want to from at all in it like a day's off on a road less travel never alright sheila once up dude not much man doing well dude always good having you on you are as always i give you this title the most interesting man in tech you're you're in a great investor your tech investor how big is the fund how much the total of you you invested now at this point about four hundred and fifty million in total okay four and fifty million dollars so like you know i've learned a lot from poker right and then poker that you learn all these lessons that actually like cross apply totally outside the domain of poker and what would you say the lessons from investing that apply to life i think you know one is just like upside can be greater than downside like so if i invest in a company let's say i put three million dollars into a company there's is a possibility of it being three hundred million dollars but the downside is capped at three million i could only lose three million bucks i could gain winner three hundred million bucks yeah because if you don't work in investing or anywhere where you have that sort of asymmetric risk versus return let's just say you have a hourly wage job right like your sort of your mind gets trained into this linear i put one in i get one out right like i can't put one in and get fifty hours of pay out of this next hour that doesn't really ever happen in a normal job but if your job is investing you're like of course that all the time lose one times my money but sometimes i gain a hundred or a thousand times my money back and that kind of breaks the brain and you started like start to see you know other opportunities similarly that have that as they kids say the of risk written return alright so that's one there's something around this portfolio theory like you know out of the four hundred fifty million you deploy right like what does what does winning look like you probably need to return some multiple of that four hundred fifty million so what does winning look like for you you put in four fifty what do you need to get out for this to be a couple billion dollars couple billion dollars so let's say two billion let's just use it is a rough let's say it's five hundred to make math easy right so five hundred million four exit that would be great over some ten year period yep now of that two billion how many companies would you go into and of those like how many companies would be responsible for returning all of that money it's only gonna be a few right give me the minute there yeah so almost all of the returns are gonna come from like ten companies out of right hundreds that we will have invested in correct and so there's something like that in life too right whether it's like people you meet or dating or like there's some portfolio theory some power law where the few will drive like all of the joy the value the relationships the the opportunities whatever and then you just do the rest because you need a portfolio in order to find the few that are like yeah the big outliers it's true and it's also it's also in a related note there's like if you increase the surface area of companies you meet you have the better odds of finding that one like when you where you really know and it's it's gonna work and so in life i think increasing surface area is good like saying yes to stuff right this a great blog post sky called building your own yacht have you ever read this blog post is like very obscure i got this from some random twitter account the real estate g6 six sorry i yeah like normally i'd be like pretty low expectations but this is this over delivered and so basically argues the following it says most people in their life they don't do anything that compounds right like most people are non compound in general okay so we and then we kinda know that okay money has this compounding thing right you can compound some interest or rate of return ten percent a year in the p five hundred and over every ten years that's gonna or every seven years that's gonna double great so you sort of see compounding financial but everything compounds including relationships skills knowledge everything else and he has this story about building your own yacht so let me read this out for you okay so it goes if you aren't familiar aristotle on assets by the way this might be a totally big fictitious person for all line know but it doesn't matter this story works either way he was one of the wealthiest businessman of the twentieth century he start off as a tobacco trader and he ends up you know being this big shipping magnet so he's he makes his bones in the shipping industry he's dating famous actresses okay so he lives this life but he has this one sort of hack for relationship building and he called it building your own yacht so he basically talks about how this guy basically his one of his investments was this yacht which seems just like a splurge purchase like a discretionary purchase but he argues is like think about the power of having a yacht and he goes the way that humans are wired is like we are very suspicious of cold introductions strangers on the street people emailing you that you don't know but like a warm introduction or a warm relationship is so much you've already bypass like ten hurdles that come from taking somebody from cold to warm and so he argues using these like think about it this way if you think about relationships you would wanna have if you meet somebody you wanna do business with them or you just wanna socially connect with them you would want social proof like is this person cool or they legit are they friends with people that i already and friends with or or respect yeah and basically like from the moment you step foot on a yacht social proof is done credibility is done and he's like on top of that you enter their frame like you are literally on their turf and from the end of he's like there's also the law reciprocity which is like if i invite you or give you something there's a part of you psychologically that will want to reciprocate and return in some way and often the the law of process the way it works is like it's not one for one so like if i you know just do you a quick favor bring you a drink and then i ask you for a much bigger ass than the drink you're more likely to say yes and so he talks about how in he's like yeah okay that works with a yacht but he's like in life there's actually all these little yachts that you can create that don't cost the same amount as a yacht so you know you host a dinner right you create an event you send out you know free materials a newsletter content those are all these are all little yachts yeah you can create create all this like inbound luck and relationships and things that can compound because you create this like asset that you get to use from there on out so i thought that was like a very interesting point i'm curious what that brings up for you totally and i think like for you guys the podcast is partially that yeah exactly thanks to this conversation i think i'm gonna i'm gonna start doing more dinner parties because i think it's just like such an easy way you bring people together like also oftentimes i meet somebody and i'm like i wanna hang out with them again but there's no real no excuse there's no excuse but if you just invite them over it's better and i i think actually i think the best thing to do is invite them over your house because right then there's some feeling that like it's a much stronger feeling than if you'd invite them to a restaurant well even as an investor osaka did this right chris sa did this with his he moved out of san francisco where yeah in san francisco you don't have a yacht know you're just meeting at coffee shops in little you know little places like this you have an office whatever he has an office there's nothing special about it he moves to tahoe and truck actually and he basically has like a cabin on the mountains with a hot tub and you can ski and like his dog is there and his kids are there and he's got those guest house and then he invited you know travis from uber over and they hung out for two or three days and the invites kevin's system hey dude come just work out of my place in tahoe for the week and then when they're on his turf in his yacht obviously like the connection and the depth of the the relationship built way faster and he basically attributed that move to you know some of the best investments of his career is like having that little yacht it's great makes makes complete sense i've talked before about the way that i know how to make money about how build a money making skill about how to leverage your time and energy and the team at hubspot actually went through the video where i explained all that and turn it into a free downloadable cheat sheet on my four rules of how to make money now this is not you know get a quick advice it's just core principles foundational principles about building wealth things that i wish i knew when i was you know just getting started and so if you wanna download it it's in the description below it's totally free you can go get it thanks to the folks at helps hubspot for doing the research making this document and make it available to all you guys alright back to the episode yeah there's some people who who've done a they've they've sort of product ties this in an interesting way that i've met they one person i know they knew that nick gray is amazing at these two hour cocktail parties and so they just like we're like hey nick like can i commission you to do the dinner party part for me and and he's like great i love doing and so they worked out a deal where he would do it for them or i know somebody else that did this with if there's a conference in town they would kind free air airbnb actually travis from uber used to do this and his old blog post he talked about what he called the jam pad which was his house san francisco he he's hey if you're in town for this you could stay at the jam pad and he's like you know what does it cost me to have some people on the couch nothing little inconvenience little might have to put up so was also some weirdness but ultimately like i'm creating this magnet this isn't this little bit of yacht where i'm just gonna have this flow of interesting people coming through that might who knows who knows what what's gonna happen but the asymmetric upside was there for i've got a friend satya who does this poker game every week and he'll invite anybody all sorts of interesting people from like ceos of like prominent companies to i i was i just went to this deli had a sandwich i loved it was talking to the owner and he knows satya and he was like yeah he came in here he loved the sandwich and then he invited me to play poker and i was like that's so interesting and he this right like i went to go play poker with these ceos and you know all all sorts of interesting stuff has happened thanks to that so i think that's his little yacht it's interesting you know these are all so obvious it's like oh host the dinner party this whatever but if you kinda look i i know at least for me if i look at my life i'm like i'm i'm very underweight there it's like you know i'm pretty overweight on don't know social media you know other things that i spend a lot of time on and these other things that i think if i if i am honest with myself like would clearly add value and i just don't make the time for them like and then sometimes you need a reminder or in this case like just the word of like oh yeah i'm just building a yacht here suddenly it elevate the importance of the thing i'm doing from like i'm just proposing some people over we're gonna have a dinner too to like no no this is part of my this is part of my you my yacht i'm i'm like this greek dude you know that that's me right now and so sometimes you just need to del dilute yourself totally another one is so you know we're both active on twitter they're are folks that are like mutual folks that you like their stuff they like your stuff recently i i would say like once a month somebody i meet somebody for the first time because there's somebody that is a mutual on twitter like we like each other they reach out me and say hey like let's grab lunch and it's usually people in from out of town like people who are in town you just expect that you're gonna see them but if somebody's in from out of town they're coming to san francisco they they go on a mission to meet all their twitter mutual and i think that's great like people people do that like when you're traveling especially in san francisco if you have a lot of mutual here just reach out to them right yeah that's it's so true like tourism right like if like i've never been able to alcatraz i've lived here for fifteen years but if i would came to visit i would have seen it that weekend absolutely you i was gonna ask you about ai because i feel like you're pretty plugged in and you have you're thoughtful dude so think you have opinions are kinda like where the world is going so i i want you to paint the picture like game of thrones style you know the intro game of thrones are they have the big map it's like then you give this map first let's so like the high level map for ai is like what well here's what it appears to me curious you're your a per point of view that there's this race and i don't fully understand the idea of a race because it seems like whatever one company does the other companies have sales later so i'm not sure like if you got to the finish line then what what is the finish line and how do you win this supposed race i'm not sure about that but obviously so much money's being invested that somebody believes that there's like a a victory condition of this race i'm curious about that part of it first like the the concept of an ai race what do people actually mean and how is that gonna play out so many things in life have been winner take all in tech especially yeah so like there's one major search engine and there's one you know facebook on social media of course there are others there's twitter out there but a lot these businesses have scaling returns or network effects and the same is true in ai probably like one company is gonna have all of the context they need to be your best assistant and so i i feel weird saying this because i use i right now use claude gemini and chat gp every day and some queries i'm doing the same query on each but in the long run that's not really sustainable and also not everybody's like me most red are probably just gonna have one and the context embedded into it which is like all of your past conversations or if it's gemini they have all your email or you know if it's if it ends up being meta somehow they have all that context that's gonna be really valuable so the first idea is that everybody in the world is gonna want is gonna have some ultra smart helpful assistant which is some blend of like google that just answers your questions for you but then also like can make things for you write things for you create a plan for you research a things for you like do the job for you and like today that's today the leader is chad gp i think they're like close to like a billion maus and you know google's is gonna quickly try to like you know google is trying their best to do that it seems like nobody else is close in that race specific that's specific part of the race that every human has an assistant open kind of launched chat and it was unexpectedly a hit for them it's it's crazy to think now but they didn't think it was gonna work that well right an open was an enterprise company and then through the successor chat became a consumer company but google already has all of this context on you and they actually started this whole l m thing they screwed up along the way with bard and all sorts of funny stuff that they did but now gemini is really really good and so in that consumer race they've done a very good job gemini has and i think has the momentum on consumer right now then there's the enterprise piece which is like a lot of enterprise folks use claude and i personally use claude more than i use chat and it just allows me to do more things like for for the kind of research i do on companies claude is just my partner it's my spa partner like i'll it's like having like we actually didn't hire somebody this year because we're using claude more than ever right well you you you essentially did you hire a person imp lot essentially exactly exactly okay so there's the race to have everybody gets sort of all intelligent super helpful always next to your chief of staff that's that's the chad analogy then you have you know like in game of thrones you'd have like the whoever like oh is like really good at the the sea battles right the ocean yeah that's let's say enterprise and and ant philanthropic doing pretty well there right now and and they're all gonna compete for everything but like they're doing pretty well right now and then he have the king of the north she have elon up there and he's marching and he's like i'm gonna put data centers in space and i'm gonna catch up with g and we're gonna win and so what do what's your take on how that where does he go how does that work i would never ever ever bet against elon but as of right now i find g to not be as useful but i think i think like it's possible that everyone has their favorite and you know over time people sort of slot into their favorite it's like coke pepsi if you're yeah cop right now if you are a working in code you're probably using right okay so now okay well let's keep going through the battle then you have all these saas companies you've got you know today's sponsor hubspot you've got salesforce you've got like all adobe fig all these companies that are like cranking on revenue and grow and earnings and then they're stock is just plummeting because the market believes that like they're gonna they're gonna get somehow eaten away but i believe i it must be that that's why the stock is going the business fundamentals are strong but there's this question of twenty years in the future is this company stronger or has has it just been eaten away by ai that can do all these things what do you think happens there is that overblown is that a is a buying opportunity or are you equally suspicious of of the future of these companies i'm suspicious of the future a lot of these companies and i just think about myself like right now i already am doing a lot of image creation in gemini nana banana i i'm a paid user of canvas a bunch of adobe products right and yet now most of my image generation is already on nano banana it's just so much easier right so then like can those guys build it probably yes like some of them already have pretty good stuff like adobe ai stuff is very good fig most good but will i just will there just be one model to roll them all and i'll just need everything in there it's my assistant my assistant doing it for me so what do you need to be successful as an independent company is a good question because if you look at all these like early ai companies so there was like there were the ones that just helped you write jasper was one there there's some others ways and like those guys i don't know how they're doing now but i imagine not well because i don't need another tool to tell me how to write like right can do that for me and then i think the same is probably gonna be true in image generation and then all these other products too like even even law there are these companies harvey and leg which are both doing phenomenally well but ant philanthropic launched their own legal things so like what are the businesses in which you're you have less story about being cannibal from an existing ai right there there was like a quote from sam oli maybe two years ago or a year ago where he said they were kinda asking him this question hey developers are trying to build but we're all worried we're gonna get steam rolled and he he was like yeah you should think about what we're not gonna build goes here's a simple test like there's some companies that when we say there's a new model update they get really excited because it made their existing things so much more valuable and then there's other companies that are terrified when we say there's a new model update because we might have just swallowed what they did and you should think really carefully and their response was sort of like okay so so wait what are so what are those things that you're not gonna even do right that's like it's like a meme where it's like wait sorry are you gonna say what they are or we just need to to yes right because it seems like an ever expanding scope that that's pretty tough it seems like the lawyer one would probably be easier because a lawyers you know it's a workflow specific thing there's like security compliance there's like it is like really like a lot of nuance that you would have to build on top of that even if chat can quickly generate a document and write it or read it still probably there's enough like domain specific workflow and risk where somebody specializing and it will solve the hundred small problems that the lawyers care about that chat product managers aren't gonna care to you totally i think that's true and i i think in your in your the case of hubspot salesforce like i don't think those things are gonna change overnight i think it's gonna be there's a people are gonna keep using those like systems of record for a long time as a fund we think about this a lot and my partner horror wrote wrote a piece last week called the last mile problem and basically we talk about what matters and it's what you just said domain context and workflows so like if you've got the specific terms and norms of a given field if it's health care legal accounting you can produce more trusted outcomes and integrations so like integrations into your salesforce instance are valuable or in health ehr or whatever the case may be and then there's also some like compliance and human in the loop element that i think really matters so i i it's hard to know though it really does feel like a lot of these businesses could at least be very challenged by the general models what are some like if if i just gave you a million dollars and i'm like you gotta invest this into any ai companies public private anywhere what where do you have like a lot of conviction what would that what would that portfolio look like where would you put the bets let's take take a million dollars were you putting the bets yeah so i would say like right now with you know ant philanthropic being valued at nearly four hundred billion and open eye at like eight hundred billion i don't i'm not gonna put it there like how how big could those companies get and what's the risk reward i think you know could they be trillion dollar companies yeah but they better be trillion dollar companies right like if they're not that's a failure right so i'm i'm not putting it there it's wild to think that like we only had the first trillion dollar company like not that long ago yeah and now i like what six seven years ago i feel like it it was a really big deal and now we have basically almost trillion dollar private companies that didn't even exist ten years ago it's crazy okay so where would i put that money so i i think it'd go back to this like where are where the vertical opportunities that are very interesting and i think on the general consumer side i think it's tough for me to find one because on the consumer side it feels like i probably am going to be using gemini or chat or one of those generalized models they're gonna end up getting my context for for the stuff i need you know there might be other interesting ones that do stuff like sun for music is interesting they've actually they've grown like crazy to turn an out that i would not have predicted right they're like hundreds of millions of revenue i believe yeah i'm a power user of you know yeah amazing it would be a fun project i mean a lot of people are obviously doing this but a fund a fun project for somebody would be to like build a brand around a musician that you've created on ai and like marketed it through spotify and all that stuff there obviously a lot of them out there but if i had more free time i would probably that'd be a fun one to do yeah yeah exactly yeah i've played around with that idea as well like what would it take to get on the charts right can i take this song could i create an artist with an avatar can i build them up on instagram how would i do this and just see like total just get to play you know have have this sort of like fantasy musician arc you know take you take six months and just see what you could do like i'm pretty sure i could do it if i just dedicated six months to to do it now again it was like maybe it's not worth the time but it's fun it's on my list it's on my my itch list here of like possible projects yeah as on a unrelated note i just saw this on twitter so i don't know if it's fully accurate but there's an epstein files podcast that's entirely ai generated and it apparently is now a top fifty podcast on the charts i saw when he launched it and he was like it's getting down like a thousand times an hour right now and then it was like update three thousand times an hour it was like kind but what is the actual podcast what is it is just reading the emails out loud like what is it trying to do i so after i saw the tweet i went and i listened to the intro and it's kind of like notebook l so it's like it's like they're two hosts gotcha back and forth about it and they talk they talk about a different thing each each episode i wonder how many more things are gonna be like this right so like i'm not safe as a podcast right because you can you create podcast podcasts about you know about anything and now if you can auto auto create it so what they did was they've basically like here's the source material that's very juicy very dense and maybe it's gonna be keep growing right so there's some runway here and then you feed it into notebook l and then you create a podcast out of it like automatic course you could do that like you know about everything i can do that about sports i can do that about anything that has like this and this big feed of like you feeds stock to put into the to into the model right that's it's pretty wild i thought about creating a podcast that was interviews with the great dead so it's basically like could i do a podcast with steve jobs now with ai oh yeah like maybe i could maybe the tools are now good enough where you could actually figure out like what would he say and it actually as enough it would give like sensible answers you could copy his voice using eleven labs yeah you could create a digital avatar using one of the video models yeah and you could do the whole thing and so like that's kind of interesting like well what if i did that that'd be cool like you know just me and angus khan for today's totally have you seen delphi the like they're making like a clone right del yeah what is it you can make it's delphi dot ai you can basically make a digital clone of yourself and they have them with like arnold sc and other folks like that like you can you can talk to them basically do kind of what you just said are they pretty good is it they're pretty good i i haven't i haven't played around with it that much but from what i saw it was pretty good and apparently the company is doing very well they raised from sequoia other like off the races wow so people are like i just wanna chat with michael like michael o on here i wanna chat with michael o yeah i think like i saw lenny lenny has one lenny your guy brian hall has one and and he does like founder coaching via del so i i just ask michael lo the creator c the talent agency said this i was like i'm having a meeting about our podcast deal to renegotiate what should i do and there come go i got michael representing me now this is fantastic that incredible he's like you're he goes said you're negotiating leverage not just rates and then he goes into this like long strategy okay this might be awesome actually i don't have to give this guy ten percent either this is fantastic exactly today's episode is brought to you by hubspot did you know that most businesses only use twenty percent of their data that's like reading a book but then tearing out four fifth of the pages point is you miss a lot and unless you're using hubspot the customer platform that gives you access to the data you need to grow your business the insights that are trapped emails call logs transcripts all that unstructured data makes all the difference because when you know more you grow more and so if you wanna read the whole book instead of just reading part of it visit hubspot dot com alright so that's that's a are you personally using ai in any interesting ways i think there's some like simple stuff that's just too annoying for me to do like i my my wife and i my wife works at meta she has after after five years there you get a five week break called recharge and we're like figuring out what to do and there's like a ton of research i'm trying to do and and one of the ideas is doing a road trip on a camper in a camper van in europe and they're are these things called relocation specials that i've done a bunch of times where like they need to move a camper van from one place to another and they basically give you the camper van for free and you can like move it over a couple weeks i've done it multiple times and it's it's fun because you take the camper van one way normally you have to take it and bring it back to the same place right this is both cheap and you don't have to bring it back to the same place and it'll be usually be like a new van they have to move from the factory somewhere else so it's like what what is in private jets empty legs or what it would be like legs yeah kinda like empty legs but for for for the the normal people like us so i i've had ai do a bunch of research and find it for me message message the camper van places and ask them ask them that's been kinda of fun and useful i for this event i had i wanted to save some money and had had ai do an exam for me to become like a licensed travel person i saved sixteen percent on this big big event so you needed to become a life licensed what travel agent or what you to become yeah it would it was sort of a hack because one of my portfolio companies helped me that is in the travel space but i had to do i had to do these exams it was like i don't remember how many hours was like ten hours of training and then some exam and i just i had ai do it for me and so it it goes through all the training material it took the exam as well or and that's a basic alright i wanna or you had this tweet a lot a little while back i wanna i've been wanting to ask you about so you were somebody tweeted out they said the worst mistakes are decisions in human history and they were you know adam and eve eating from the dream the m trading luca dante it's right so they're were just going through random examples and then you had a bunch from the business world i wanted to to to go through this i was curious if you have any you know tell some of these stories i don't i think all these stories are super well known totally a lot of them are this like innovator dilemma that's kind of a broad theme which is so kodak they invented the digital camera and then they didn't sell it because they were worried it would suppress their film sales and then all these other companies started selling digital cameras and then kodak basically went out of business like kind of the worst way to lose right like that's my nightmare as a and then the same thing happened with excite so excite had an like google wanted to sell to excite for seven or fifty thousand dollars very early on it was just larry and sergey i wanted to sell this idea to them and excite said we don't want them to get answers we want them to stay on the page so we can serve up ads and then so obviously the rest of history there so the those are kind of like a theme is you would cannibal analyze our business so we're not gonna do it and that actually like back to our early discussion about ai that's one that i i was worried that google would get into i think a lot of people were worried google would have that problem and google stock was really in the shit like a year and a half ago and then as google like gemini became great and people realize okay like soon there's not just sitting back saying i'm not gonna i'm not gonna do this like he's doing it too and and then google stock is real well but i think that that was a big worry people had because how google makes money is on ads when you're searching for stuff and if you're not searching for stuff like their entire revenue model goes away alright yeah that's a that's a good one what about this story of it seems like another one is like selling early that's the ron wayne store so what's the what's the ron wayne story yeah ron wayne was a cofounder of apple with jobs in w and very early on he he had a ten percent stake in the company and he thought it wasn't gonna be worth anything and wanted to focus on other stuff so he sold a stake back to them for eight hundred dollars which one we got hundred dollars not even like an grand so on ten percent of apple he's like kinda written out of history if he was i didn't know he was actually like a c cofounder founder what what did he do what was this guy's role oz making the computer jobs is jobs he worked at atari with with jobs and and w he was actually one of the early people that brought them together and he was like let's figure out a new business opportunity and i think it was actually like in his home that they created the idea for apple and and it was like it was split between w and jobs like i think they each owned forty five percent but wayne for like bringing them together he was like he was like the adult the original adult in the room right and then i think there was something where like steve jobs got a line of credit that they would be personally liable for to start like to purchase materials to to fulfill an order and so ron win was like listen i can't be personally liable for this i'm out and he sold his shares back for eight box what happened to this guy as he as he talked about this did he end up doing okay like there was a guy who was a partner with buffett and mu pretty his name rick something and he he got over leveraged he had to sell his stake back to buffet and mu and basically missed out on berkshire and know he ended up doing well outside of it but like you know a cautionary tale for like kind of buffett i think said it best he goes you know rick was in a hurry and he's like me and charlie we were not and that was the difference yeah i i looked it up afterwards wayne ran a stamp shop and he'll disco discount yeah this is gonna be like a netflix original someday tell me about this one so you said soft bank they own five percent of nvidia yeah and they sold it to plow all the money into we work and i'm i'm what i'm interested here is actually your opinion on masa so i don't i i i don't know a lot about the guy but i can't tell is this guy a genius or an idiot like you know when they when he released like his like i believe in ai raised the vision fund it releases the deck and it's like a picture of like a unicorn flying and it's like there's not a two syllable word in this deck you know what i mean like it's like this is made by children but this is actually the deck and the vision of this like the biggest venture fund in the world did he just get lucky this is just a guy who got lucky and it's kinda like you know i've been to casinos where i play against you know some random you know guy who some asian guy who's got a huge chip stack and then you you're like wow you assume he must be great then you realized like oh no this guy is like super suspicious and if this is happening he goes all in and he just happened to win right like what's the story of masa is he a genius or an idiot yeah listen i know people who have pitched him and people who have worked with him who are still wondering the answer to that question no i mean so like the backstory story for people who don't know is he had this legendary bet which was on alibaba he invested them very early on after he met jack m he put in twenty million dollars and it turned into a hundred billion dollars where like just like this mask and he had the twenty million from what he he created like ces right is it was that the first thing you created like these tech conferences or magazine bank was like a software distributor and publisher and it was like really big in in japan and he partnered they partnered with yahoo to create yahoo japan which yahoo japan ended up being way more successful than yahoo in the us and so they because there's was a jv they like yahoo only owned a small part it i think soft bank owned more and they had a bunch of money from yahoo japan and i think that's what he plowed into ali okay so he was a good entrepreneur at least alright a great entrepreneur i think he's like and he's very risky like he's fully risk on like he lost all of his money then gained it back and then you know does it again and he's like he'll he'll like go full leverage like all out debt and look with the vision fund a hundred billion dollar fund what's crazy is a hundred billion dollar fund seemed so crazy that it was like is it even real is this april fools day like when it launched whatever six seven years or no i guess now eight eight eight or nine years ago and they wrote massive checks into a bunch of companies sometimes competing companies and i i never thought it would work in my main reasoning for at the time think it wouldn't work was the companies that need a lot of money or not necessarily the companies that you wanna plow money into like it ended up being a lot of like money losing companies that now eventually like many of them ended up being successful like uber and door but you know then there was we work which i think they put the most money into yeah so what's the verdict on the vision fund it it did did well we just too early to say or would just i think it ended up being okay it's an okay fund it's not great but like if you're looking to deploy a million dollars like there are ways you can get right five ten million dollars like if you invest in a good fund a hundred billion dollars if you're deploying a hundred billion dollars like you're not expecting to five exit if you one and a have two exit maybe that's okay depending on timeline gotcha what do you think people should be paying attention to and maybe the better way of asking that is what are things you're paying attention to right now that you don't think a lot of other people are or you know the the masses and maybe maybe or or even like general population of smart individuals right so not not like literally the average american but also not the guys at your vc dinner so is this somebody somebody in between right the general smart person what are they not what are they underweight paying less attention to thinking about the wrong way that you you you were paying attention to do differently i think everyone and i'm encouraging my parents to do it too should just be and this is like an easy answer should be just using ai more i think when my parents give an assignment like my parents often are like hey can you book this for me i'm their personal assistant for now i'm trying to teach them to use ai and actually they're doing it and it it actually kinda surprised me but they're but they're they're able to look stuff up on ai that they you know they weren't doing a month ago and they're getting answers and i'm also encouraging them not to send me like stupid fake forwards and to look everything up and make sure it's legit thanks podcast is brought to you buy my friends at mercury they make the world's best banking product i think you know this already i use mercury for all of my businesses i think i have like maybe seven or eight businesses we use mercury as our business banking across all of them and now they actually just launched a personal banking account so i have my personal account there i moved off of wells fargo in chase i'm just all in on mercury why i like products that are easy to use i like products that get me and the problems that i have so like it very easy to make a joint account with my wife very easy to been up virtual cards one click and i get savings yield it just has all the stuff that i need in one place so if you're looking for the best banking product on the market it's definitely mercury i will fist fight anybody who dis me on that go to mercury dot com slash personal and learn more mercury is a fintech not an fdic insured bank banking services are provided through choice financial group and call them an a members fdic i'm curious if you have any non consensus or sharing opinions about something so for example you know most people think that x y z is you know kind of useless but actually i think that's wrong i think this is amazing right i'll give you i'll give you a simple example so brian johnson was initially i would say completely overlooked the first time we had him on the podcast he really wasn't like brian johnson the kinda of media yeah personality at the time he didn't have a big he just had his website blog uploading like his own like blood markers too and we were like this is cool guys like really tracking everything and he's publishing it on a blog and then brian johnson became just like kind of like beacon of longevity and then people are like wait to see a vampire what's going on over here like is this too much and so he became like polar and now he's like full on like youtuber content creator and so one of my like opinions that i i don't think a lot of people share or even i've thought a much about is i think brian johnson might be the best content creator on earth right now you know like i just think he's like running circles around everybody in the same way that when people saw what the kardashians were doing early on or the paul brothers it was really easy to dismiss as you know sort of silly stupid useless whatever and then like you know fast forward a decade and they've built these really big empires off of that i think what brian johnson is doing on social media is incredible and it just literally as just a content creator like i just think what he's done is is is genius i think a lot of folks especially going into a new area they weren't before they started on content and became successful that way and kind of like in our in my world of venture capital and h like they are basically all of the s venture firms are pretty old they were around in the dot com bubble the only new one is entries and h and the way they did it was by like owning and controlling the media and they've been a really good job at it they have a lot of people they put out a lot of content and it's worked for them and that was pretty strategic of them right so like they they enter the vc world they wanna do well you to do well in the vc world you need to have brand that way either bring deals to you or get you access into a deal when you want it to to be able to go lead that round right yeah and so i guess like give me the inside baseball there what did they how did they approach that problem do they how do they solve that problem yeah so you need a brand you wanna be recognized and the way they did it like so first of all it's only like fifteen years old injuries norway and if you if you look at the other s firms benchmark sequoia etcetera they're a lot older and they they really earn the reputation sequoia even earlier but benchmark in the dot com era so these guys basically said like we we're gonna do it differently and we're gonna provide instead of just having one partner to work with you're gonna work with a whole team of people and we're gonna support it with content so we're gonna promote our portfolio with content but also people are gonna listen that content gonna think about it injuries h and think like those are smart people i wanna raise from and it really like before injuries and h there was not a lot of content on venture like a couple guys had blogs and recent totally changed the game and they actually they learn for michael i think o did a lot in building this c into this like you have this whole team of support around you and that's what injuries modeled it off right right yeah it seems like you know you fred wilson have a blog or whatever yeah and i've seen this now in a couple spaces where we all think we're doing the thing like i would say at the time there were some vcs who thought we were doing content what do you mean yeah i have my blog and then they're like somebody brings the gun to a knife fight where they're like oh here's what we're gonna do we're gonna invest essentially you know like ten i i would i how much do you think they spend every here on just the median content side like what do do you think is the expense part of the p and l for them it's gotta be easily tens of millions easily tens of millions exactly tens of millions of dollars on content and so you're like we're doing content and then they were like well here's what we're gonna do gonna build this like a company and we're gonna like they made acquisitions in that space i they bought eric's company they you have huge teams of people they create multiple shows they like have studio sets they go on tour they're spending a huge portion of their time just going on other shows and so they go in with just a level of seriousness and scale that just blows other people out of the water and i've seen this over and over again the charlie mu quote take a simple idea but take it seriously where it's like we're doing this right and the mister beast like we got to know jimmy recently yeah like the last few years and like he did the same thing like youtubers were a thing and youtubers would do these stunt or challenges and he just took that simple idea way more seriously than everybody else he's like well i'm gonna put all the money into him i'm gonna build my own sets i'm gonna be if you've ever been to his place like oh i mean it's like giant like he's got the biggest sound stage in north america like you know he's he's building the biggest sets is it's like a construction company when you walk through his his his area he's got teams of people every dollar they make they invest and more they lose money on every video right like youtubers were like hey we're doing we're doing this right and then he did it at a different level of sale scale and seriousness and so i always find that interesting because whenever you go to into a new space sometimes the right idea is actually there it just hasn't been like taken to the limit and if you took it to the limit which is also what brian johnson did by the way like totally eye hacking quantified itself that was an existing community he just took it to the limit and and when you take it to limit like you get a whole new thing a whole new level of success can emerge i think a lot of these folks like if you're if you're starting it something new you have to take it to the limit yeah you just sent me this thing i've i've seen this before so this is explain what this is explained this thought this might be fun basically two weeks ago i saw that the breaking bad house you know the house that that brian cra throws the pizza on top of was for sale in albuquerque iconic iconic house for any of you anybody who seem breaking bad and so a friend of mine a friend of mine told me was for sale and i was like we need to buy this was this like very publicized or like kind of a friend just noticed like hey he hey that's the house like how how was size but like it okay it got out there and it was listed at four hundred thousand dollars because that's kind of it's kind of like a small it's like a nineteen hundred square foot house in the suburbs of albuquerque like twenty five minutes from downtown and i immediately was like we need to buy this house it was this four hundred thousand and so we like booked a flight to albuquerque like an hour later and we like built this model around what are we gonna do with this house how much can we spend on is it so you you go to the house does it look like the show inside still or it looks totally different it looks totally different on the inside okay so they they changed the inside yeah huge mistake when they did the show that was just someone's home basically was and it's this family that's lived in the house since the seventies they bought it for almost nothing in the seventies and then they they like got a call from the show saying like hey your house looks like a normal house albert albuquerque that we might wanna use house they only use the exterior of the house they didn't use the interior of the house for filming oh okay gotcha and are they were they just annoyed people kept taking pictures of the house because in san francisco there's like the full house house that we're surely couple blocks from me and just people constantly stopping and taking photos out yeah it's extremely annoying for them so so much sir that they built a fence around the house so you couldn't actually like throw pizza over and then the neighbors are pissed it's not a good situation so they were like could sell this house and they listed it for like fair market value might be three hundred and fifty thousand dollars like looking at comps and they listed at four hundred thousand and that they had tried to do like a museum or something but they got they got shut down by the city and so it's been you know the show's been off for what like twelve years they could've they could have turned into something amazing in the meantime but they did they just continue to live there and so they self for four they listed four hundred thousand dollars we say okay like how much can we make off this thing if we turn it into an airbnb and i love experiences that are also the house like i stayed in brian c house i've stayed in this like you i've stayed in a bunch of architects homes around the world like i love unique architecture so i thought like i could turn this into an airbnb what do what do we do so we like built this model around it like assuming we assumed we could charge eight hundred dollars a night versus like it's a four bedroom place in the area you might be able to charge two hundred or fifty dollars a night but given given that it's an iconic place like if i went to albuquerque with some friends i would definitely wanna stay in the house it would be worth it for the story we assume like sixty percent occupancy we we made a bunch of assumptions based on information we learned like we looked up what the stranger things house is going for all sorts of stuff like that and then and then also like what the roles around short term listings are we actually spent time with an airbnb consultant like i called up an consultant spoke for an hour and and got some ideas there and like i had this other idea of like i'll build an rv like his rv and just park it out front that'll be another bedroom because he's not enough space mars and so we basically basically got comfortable that we could spend nine hundred thousand dollars for this thing and it'd be worth it like i'm sorry the so the math was you thought base k you know a worst case scenario oh the worst case ridiculously low so you didn't need need to worry about that one too much but you were basically the expected case was that it would make like a hundred and seventy five grand a year a rental income off the airbnb b and that it would cost hundred twenty k to run yeah and you'd net something like fifty five sixty k a year off that rental property that you own at albuquerque and more importantly an epic story an epic story absolutely epic story and it was just like it was honestly so fun like actually part of the thing part of what i love about my job is i get to do this like i get to due due diligence on a space i don't know much about and over the course of the next day like i learned a lot about airbnb bs i learned about a lot about breaking back a lot about this house right to be clear does this have anything to do with your job does not to diligence do due diligence my job is like doing diligence right use the same skills scott yeah same skills so we decided we could spend around nine hundred thousand dollars and it it would be worthwhile it would make us a decent return and then also to your point be just an epic story be so fun to own it right but then the major risk was albuquerque has these short term rental laws where neighbors can call call this hotline and basically shut you down if they're unhappy and so there was some concern that that happens and if if the short term rental ability goes away this house becomes worth three hundred and fifty thousand dollars like exactly you know what every other house around it is and so there was some risk there that you it's hard to price in but basically we decided we could spend up to nine hundred thousand dollars and ultimately the house went for over a million we don't know exactly how much but it was sold to aidan ross who for those you don't know who's who's a popular streamer and you know for him he's got a totally different revenue stream which is like he can make a ton of audience streaming this to this audience he can market to this audience so he came at it with something that we just don't have and can't compete with but right was really doing this so so somebody who owns a stranger things house what are they making it's like two thousand dollars a night and it's fully booked hundred percent occupancy like did they make the inside match the show yeah they made the inside match the show and put a bunch of other memorabilia and that was our plan too was like reconfigure to make it look more like the original like some of the rooms will look like the original parts of the show and then the other rooms will just have like breaking bad memorabilia we had talked a long time ago about buying michael jordan's house which was on sale for like a very long time in chicago it had like started at like twenty something million and then had dropped all the way down to like thirteen twelve and on this one of the early episodes this podcast rex should we buy michael jordan's house and like to could we turn it into whether it's a airbnb it's like a we were like you know you could fractional like you could use an n basically to fractional own it yeah and so it's not an airbnb actually it's a bunch of people who c own this thing and ultimately we we kinda let took our eye off it ended up selling for like think like seven or eight million dollars again ended up going for like kind of a steel to this guy who was just like a business guy in the area who was like dude i can buy michael jordan's house this is amazing and he's turned it like you know a short term rental sort of deal as well i've i have one more thing which is i had another business idea for people okay so you know we've we've talked about parents before i think my dad is kind of a a funny guy and i'm always trying to get him to work out to like you know live longer and you know people like us do stuff like berry boot camp soul cycle like these classes and the idea is just a berry boot camp style class for old people and you could franchises it z is that not what's not exactly geared towards old people i think i think you can easier make it easier like sort of this lighter contact and emphasize stuff like balanced joint work and even like maybe even cognitive exercises and you basically have this like welcoming place for people fifty five plus who have a lot of free time and wanna stay active and healthy and maybe you you build like a a club around it is the idea so that that's i think it's a great idea i'll tell you why so i have a trainer who basically was like you know kinda like had a body building era trained a bunch of bride trying to get in shape for for weddings all the classic models right then like you know me like tech guy trying to you know work out so we cut my house i've been working with them for i don't know five six years now he so i was like i really want my mom to to work like i think it'd be great for her and she's too cheap to like you know be like oh a personal trainer like a hundred bucks for a session that's like three months at the gym over here like the y c like i'm not doing that and so for christmas i got her like i was like i paid for by trainer world trainer for a little bit she got hooked so then she started like oh i'm definitely gonna make this investment and she loves it she's been doing it for years now and she's been in great shape so my trainer basically like suddenly his his clientele over the last couple years just totally pivoted where his his entire network is basically like auntie and uncles of like the indian community and so like my mom was doing it and then my father lost started doing it i posted this video of him running and my father was i think it it's like seventy nine years old and he i see this video on instagram of him running and i'm like what like what is going on here and he's like he feels so good he's moving again yeah he was having like blood pressure and headaches and things like that this has really been helping him he fell at our house so we had this stool that's like kinda like we shouldn't have this stool bring a little risky like i don't even know why we have it but he was he sit on a fell and literally the first thing he says when he falls this is like good thing i've been training because he like bounced back right away didn't like break a hip so we were like this is amazing so then his brother his and so like my my trainer basically goes from my house to like people who are literally like learning to walk again stand straight again like just be able to move road rotate because be one thing that you lose a lot as you a old is you're you you just stiff up so you lose rotational ability which if you go to the gym and you sit on one of the machines or other elliptical like the things that people older people do at the gym it's all rigid no rotation type of exercise and if you do rotation unsupervised like you can also really get hurt so anyways he's been doing this and i've been telling them the same idea like bro you should like this a real active service that you're doing for the world and there's not other great options for you know people who are fifty to eighty years old who want some form of like organized tell me what to do movement ideally in a social format where you're with a group of people you got out of the house like there are so many benefits like my grandparents used to just go to costco every day because it was like a bird place right it's like a place to go they would walk around they would see people they could get like a two dollar meal like you know it was it was awesome and so like that was like a huge deal for them and it's like they don't really have third spaces the same way that like you know younger people have kinda love this idea yeah it it like makes a lot of sense i'm surprised it doesn't exist already i kinda did a little bit of research i couldn't find anything so i i do this up here well there's no like killer brand even if obviously there's gonna be something that is is there's nobody's built like soul cycle who's bill barry is built like a really fun and by the way this playbook has been done fifty times now right like totally solid core and at forty five or whatever there's like so many so many yeah you could dilute this copy the the the blueprint you just change the demo i also wonder if you could like get the insurance to cover it in some way or like some way like is there some like medicaid medicare advantage plans should cover something so there is there's something called silver sneakers such a great name which is a a fitness program for older adults through medicare advantage plans but it's like it's not x like digital or no it's actually it gives members access to gyms it actually my dad does this i think that's how he pays for his y mca but it doesn't it's not like they don't have this specific thing which i'm thinking about which is like a boot camp around low impact and and senior friendly stuff right this is great wait so so silver sneakers that's a private company and they're basically saying you get access zoom so they kinda class past it they went and did partnerships is that how they did this that's right yeah and they do have they do have like online classes but i i but it's different it's like it's videos and then they had partnerships with gyms is this like a venture backed company or is this is this like they have two million visits a month on their websites it's pretty crazy oh interesting they acquired nut system in south beach diet yeah this is interesting like these guys the silver speakers like they're not gonna do you know like the the modern way of doing things they're like an old school company right but this says here nineteen million americans available to more than the nineteen million americans american student medicare advantage plans supplement carriers and group retiree plans that's cool yeah that's there's definitely an opportunity here i like these because i feel like with ai let's look like you know with ai you kinda want ai proof businesses if you're gonna if you're gonna start something new either you need to be a big beneficiary of ai or you need to be ai proof you wanna be on either end of the spectrum you don't wanna be in the middle and so ai proof like you know there's not gonna be ai that works your body out for you like even if it's in if it's smarter it guides you you're still gonna have to do the workout totally and so you and so giving people a place to go especially if ai gives people more free time or more income like anything like that it could be a big beneficiary of that i like this idea yeah it's fun one cool alright she'll i appreciate you coming on and sharon ideas insights and all that stuff and always good to hang likewise man that's fun i feel like got rude wear i know i could be what i want to from at all in it like a days off on a go less travel never looking back alright my friends i have a new podcast for you guys to check out it's called content is profit and it's hosted by luis and ph ka after years of building content teams and frameworks for companies like red bull and orange theory fitness luis and fans are on a mission to bridge the gap between content and revenue in each episode you're gonna hear from top entrepreneurs in creators and you're gonna hear him share their secrets and strategies to turn their content into profit so you can check out content is profit wherever you get your podcast