I Ranked the Best & WORST Businesses to Start Before 2026 | Andrew Wilkinson

Date
Duration
80 min
we have sixty five million of arr we do over forty million dollars of eb we also manage a two hundred million dollar fund so we're over three hundred million in revenue across thirty businesses and all the businesses in the fund prop as well i don't know i'm kinda like if that's failing like sign me up right you've owned a number of agencies how much revenue lifetime as meta lab generated for you the hundreds of millions of dollars of profits not revenue i don't know that i would still rank it very highly though sas where are you putting sas i would say it's a what do you think about marketplace well i would say it comes down to scale a good marketplace like european airbnb b at tin a i'd rank marketplace in general is that's the one i would disagree with you with i feel like i gotta ask you this because i think you get a lot of shit nowadays i think a lot of people go look at the tiny stock and then think like like max and basically you see just a downward trend a lot of people i see on twitter want to kinda look at that and say oh this guy calls himself the warren buffett of the internet and he says he buys these great businesses but what's going on i feel like i could rule world i know i could be what i want to from all in in like a days all on a roll let's try what's up andrew is here andrew is one of the most visited guests on the pod always good to have you man i wanted to play a game with you you've done many types of businesses you've done agencies and and you know private equity and you've started you know e commerce companies you've done the a huge number of companies in the last twenty years so i wanna do a game where we rank the different types of businesses that you could start and we could work out this criteria together but i i think the idea should be we're not looking at the outlier scenarios so in every industry right the world's best plumber makes a fantastic living that may not mean that plumbing is the best trade to go into no offense to the plumbers out there listening but we're not looking at just the extreme outlier so i think that here's my criteria for a great business andrew it's gonna be the median successful outcome okay so like the sort of like normal case if you can make it work that's the first that's the first criteria the second thing is we're thinking we're taking into account both the lifestyle as well as the the result the upside so you know if one thing is just makes you miserable or overwatch you like crazy then that would be obviously worse than a business that that lets you have a great flexible schedule and flexible location for example so lifestyle matters upside matters and we're looking for kind of the median success case but but you know in some of these it's gonna be like dude it's median success i mean only the top point one percent make it so you have to factor that in the likelihood of success matters in these in these scenarios okay if you're if you're listening on audio it's gonna be a little more fun if you go to youtube or go to spotify and actually you could see on screen the the stuff that we're sharing alright so here we go here's the tier list if you've never seen a tier list before they're ranked as you would expect sort of a b c d e f a being better than f but there is of course s here and i don't even i don't even really know what s stands for i think it's like from the gaming world but it's basically like s tier is sort of like god tier it's the best you can it's the best of the best okay so we're gonna start with little lay up here and for each andrea i want you to give me your almost like rapid fire take on like you know kinda what this business is why it's either great or why it sucks okay so the first one we're gonna do easy an ml which is actually a surprisingly common business that people get into if you just look at the raw numbers of people who take part in ml so ml where you where you ranking it i mean i would rank an ml as an of fundamentally unsustainable business that breaks i mean the problem with an ml is it's reliant on recruiting other people and and it doesn't actually make money based on selling services it's it basically makes money by finding the next sucker and if the person that starts the m l finds a lot of suckers they can make a lot of money yeah and the first couple layers can make a ton of money but then it always explodes or they get indicted or something like that so where are you ranking it i would say that's enough okay it's going in the f although it does sound like for the ml owner you know it's not necessarily enough you know one of the one of the associates are as they call them you know the business owners that they they like to call themselves that are underneath yeah that's apt here for them i think if you are willing to go to jail too like you can make a lot of money but i mean like fifty fifty odds to go to jail alright next one up is one that i think you did by the way say say if you've done any of these okay so freelancer which is i believe is how you started your career you were a freelance what web designer yeah yeah i started making websites out of my apartment basically i would i would rank that probably a d i think it's a it's a really good business and i say it's some it's a living right i think there's nothing wrong with freelancing or a restaurant or a corner store or that sort of thing but fundamentally it's an owner operator model and it doesn't really scale unless you scale it which is what i did yeah okay well that's the the kind of the next one which is actually agency you've owned a number of agencies you've probably made i don't know i don't know what the number is but meta lab has generated something like two hundred million plus in revenue how much how much revenue lifetime has meta lab generated for you you're design agency i don't know the exact math but i think we're probably well over into the hundreds of millions of dollars of profits not revenue mh okay so i'm assuming you might have agency higher than most people so i i think well you know what i don't know that i would still rank it very highly though you know the reason some you know my story i started a web design agency i scaled it i got clients like youtube and uber and walmart and all these big companies and i was terrified i mean it's a business where you're either making a ton of money or you're about to go out of business constantly and you swing between those two things and so because of that lumpy nature i'd maybe give it a c but it's be it'd be a tentative c it would it would kind of yeah it like it's really really a hard business and the hard part is you're saying clients come and go it's that one it can be feast your famine with clients is that is that the reason why or is it the headache of operating and delivering the service what what is it about the agents that it makes it like well not let's and instead of web design let's imagine you're an accountant and you start an accounting firm and you start auditing thirty companies now companies don't like to switch accountants and they don't like to switch auditors so if you have that that's a really high quality consulting business however if you have a five hundred doll let's say that you hired thirty people in the philippines and you do graphic design for five hundred dollars you might have months where you're making three hundred thousand dollars and then you might have months where you're making nothing because you're not getting any clients the worst thing that happens in these businesses is you win a client like walmart let's say they come along and they say hey we wanna give you ten million dollars of work over the next year and so you you start panicking you go out you hire thirty people and then a new pm takes over that team at walmart and they just cut your budget right and all of a sudden you're left with thirty people you have to lay off so i think it depends on the nature of the business honestly so you've you did meta lab you've also had like a game design agency you've had like a a no code agency you've had how probably what six to ten different ten to fifteen agencies and services business copywriting social media web development design a lot of different stuff what were the sort of top two agencies you did and what were the sort of bottom tier agencies you did well i would say that we really haven't had a lot of success with recreating the success of meta lab med lab was the business you know like i said i started with zero and now does you know very significant earnings and revenue a lot of the other agencies have not hit in the same way and i think the distinction with metal app is it did so much defining work in like two thousand eights twenty fifteen where we you know we designed the first version of slack we worked on you know all sorts of projects that were kinda groundbreaking and we planted our flag and built a reputation and so i think the reputation piece is hard to recreate and so we've we've had a lot of success with meta lab we had a lot of success acquiring a company called z one which is in spain they're a a smaller web design agency and the theory there was literally just metal lab gets a ton of leads that are too small for it so let's buy another smaller agency and let's just send them those leads and so i think we acquired that business for three hundred thousand dollars or something and we've probably made single digit millions of profit in it so it's not we didn't knock it out of the park but it's just an amazing base hit right right hey what's up if you're liking this episode the research team at hubspot has taken all the rankings that we're doing today in this episode and they made it a downloadable thing in case you wanna go see the final to your list you wanna download it and maybe have a little breakdown of our commentary for each one it's available in the show notes below you can go ahead and download it totally free okay next one up sas where you putting sas i would say it's a b probably i think it again it depends on the type of saas if you have a saas software that is a chat gp thin rapper and does something like put a funny nose on your friend's face and you trick people into subscribing to it for six months and they always churn i'd say that's a pretty bad saas business if you have a saas business that let's say has become the dominant player in funeral home management and all the funeral homes use it and they don't wanna switch because it's the standard that's an incredible saas business and mean saas businesses they're often highly recurring really good margins i mean they can be incredible but you really have to find something with a limited amount of competition or high switching costs tell a quick story of the dj software saas business because that's kinda like the funeral home example you have so you're saying it's a vertical niche tool that's like mission critical for an industry to run on there were unlikely to ever switch and you know that's gonna be super super sticky for a long time with high margins so it sounds like i don't know a lot about the dj software business but like can you just tell a quick story of that one yeah i mean for the last ten years everybody has been basically like obsessed with buying saas software companies and thinking you can't lose in that industry which right now is still true but over the last two years like i've got really scared of buying software companies because you know you look at vibe coding and l and i i just think like l m's increasingly can build software and it's not that it's gonna put all these businesses let's say of saas software company and there's ten competitors five years ago i just think there's gonna be fifty or a hundred competitors in the future and when that happens competition equals margin compression so we've basically said note almost every single saas software company we've looked at over the last two years but one came across our desk that we could not say no to and that was ser have you ever dj sc you ever go through that that life crisis you know what i appreciate to even think it's possible that i look like a guy who's dj before so i take that as a compliment but no i i had a phase in like twenty twelve where i was trying to meet girls and i learned how to dj and so i kinda knew the industry and the dominant software company in that world for the last twenty twenty five years i think is a company called ser and it's an incredible piece of software i mean dj is all over the world use it i think like dip you know a gazillion of the top dj and these two guys in new zealand built it and what they did was really smart they partnered with the hardware manufacturers like pioneer and they deeply integrated into the hardware and so what that means is that a it's become the standard right so when you're the standard that is really exceptional most dj use one of two pieces of software either record box or ser right so very limited competition and there's lots of ups starts and stuff but once someone really integrates into an ecosystem like ser they're buying like five thousand dollars of hardware they're not gonna switch off really easily and the manufacturers frankly they don't wanna integrate with some random college kid who's vibe coded some ai dj you know not to say that people can't come and compete with us is just harder because it's not it doesn't have a hardware mode so i think saas with the hardware mode is pretty incredible you know that business we shared some of the numbers when we bought it i mean it's doing forty five million dollars of revenue fifteen million dollars of eb it's a it's been growing like crazy moving into a saas model from licensing i'm i'm a huge fan of that business why does a business like that grow like are there just way more dj or something else i think as long as the dj is a desirable thing to be i mean if you think about it one of the weirdest phenomenon you know when i would go to a club it doesn't matter how much money i have in my bank account i remember looking around and going oh man there's all these great girls here but you know none of them none of them know that you know i've got all these businesses i'm i'm a cool guy or whatever and you literally that name like they don't know i have a design agency exactly exactly how much i have but like i'd i'd look up i actually had a friend who's a dj and he would get paid like two hundred bucks and some beer tickets and he'd be swarmed with girls and he'd have status and throughout the city he'd be the man and so i think as long as that's true as long as young men think dj are cool and women increasingly there's way more female dj now i just met an amazing one yesterday but as long as that's true i think people are gonna wanna do it i mean it's just fun to mix music and you can you can become famous you can you know express yourself so i don't know as long as that's true it's like we've got one of the toll roads to achieving that yeah i like the analogy you have the toll road okay next one i'm gonna do actually i'll do do an easy one restaurant i think you've owned i think you own or still own a restaurant yeah i own a bunch of restaurants actually and i always say a restaurant is a a really good passion if you're really passionate about it you love food it's a labor of love as you know i know you have a sushi restaurant but i have when i meet somebody and they say i have a successful restaurant i wanna like like wayne world get down on my knees and say i'm not worthy because if you're successful in a restaurant i just it is one of the hardest businesses if you think about for you to go in and eat a good meal at six pm people had to wake up at three in the morning they had to bake bread a million things had to go right they had to train thirty people it's just like a rub goldberg machine of business so i would rank it as an e probably one of the hardest businesses and low margin and difficult yeah for people to give context most successful restaurants but even the big chains like a a subway or a chipotle or things like that ten percent margin is the good case scenario it's like that's doing well of course you know there's there's the exceptions like luxury you know sort of michelin star restaurants might have high power margins but you on the whole if ten percent is winning and then your bunch of revenue is capped at what you can produce because again you're working seven days a week you're there for breakfast lunch and dinner you you know you've basically you can't that you always have to be there you always have to go in and make the product again fresh every single day and you're only as good as to your sort of last interaction with the customer it is just such a brutal business it is a it is an absolutely terrible business in fact it's funny that the only business you've ranked below it so far as an ml it's pretty much a a crime is the only thing that's been worse and you know like i said like we own restaurants i think they're really important but i i just don't if you wanna make money and you wanna get rich i don't think that's a good way to do it it's like i always use the gym analogy if you go into the gym and you try dead lift three hundred pounds on day one you will hurt your back and never come back and i think entrepreneurs who go into restaurants they have a rough go alright next one marketplace so an online marketplace where how do you think about marketplace so this would be something like a whether it's a etsy or an ebay or an amazon or it could be you know even marketplaces like angel list as a marketplace twitch is a marketplace anywhere where there's suppliers there's supply and demand right there's creators and viewers youtube is a marketplace of creators and viewers as well so what do you think about marketplace well i would say it comes down to scale like you've got a airbnb on the side there i think small marketplaces are really hard we own some and i think it's like lightning in a bottle if you can get supply and demand to match their phenomenal businesses but they're highly competitive i like a business where it becomes a verb so airbnb is a great example like if i think like oh maybe we should rent a house airbnb the word just pops in my head i go to the browser i look up airbnb and i'm gonna use it that i would say is probably a a b or an a business so very very highly ranked but if you started a marketplace for people who want to borrow let's say like construction tools or something like that yeah oh my god like i've just seen a million of these fail they're so difficult and so where you rank at marketplaces i would say a good marketplace like airbnb b i'd say a i'd rank marketplace in general as a c wow first big controversial pick there i can't believe you rank it as a c that's the one i would disagree distribute with you with i think if you get a marketplace to work like an airbnb it's s here well are we saying i'm working market because we're talking about a business model if you're one of the very few successful marketplaces you're an s it's like it's one of the most def lucrative businesses in the world but because the likelihood of success is so low i would have just knocked it down to probably an a if you can actually like get one get one going even let's put let's put airbnb is an a i'm with that this airbnb being agree with the business model in general as being a a seat because we're basically ranking in terms of quality and difficulty right yeah and i i just think like like for example like we could say that the services business the accounting firm let's say p w right p w seventy five years ago was just one accountant and with a few partners and now today if you wanna get audited you're a public company you have basically five options you you're gonna pay a fortune for their rubber stamp right so i'd say like we could rank that as a b or an a but we're talking about the business model okay fair enough agree to disagree on that one alright this airbnb is not the company airbnb it's owning airbnb short term rentals so saying oh you know what here's how i'm gonna make money i'm gonna get a property i'm gonna get a home i'm gonna put it on i'll be i'll be a short term rental unit owner maybe i'll do two maybe i'll do three what do you think of that plan i'd say it's a d similar to freelance you know the risk there regulatory i owned a so you know i bought a beautiful apartment in vancouver i go to vancouver a lot and i said oh i don't wanna own a second home but you know the twenty eight days a month i don't use this place i'll airbnb be it so i airbnb i'm making a fortune it's great i love it all of the sudden city of vancouver changes the regulations boom derek goes my margin there goes my business you know total nightmare and now i just it it's fine i have a tenant but it's just not nowhere near as profitable the the same thing happened to my parents they airbnb being their house in san francisco making a killing and then san six changed rule said you can only airbnb ninety days out of the year so basically three out of the twelve months you can airbnb so then nine out of the twelve months they're their cash cow disappeared overnight today's episode has brought you by hubspot because you're using only twenty percent of your business data is like dating somebody who only text you in emojis first of all that's annoying and second you're missing a lot of the content but that's how most businesses are operators today they're only using twenty percent of their data unless you use hubspot that's when all your emails your call logs your chat messages just to turn into insights to help you create your business because all that data makes all the difference learn more at hubspot dot com alright i wanna do content creators so for the person who says i wanna create the next podcast i wanna be the next youtuber i wanna be an instagram i'm gonna build a following and then i'm gonna make a ton of money because i'm gonna get brand deals or launch my own products or who knows what but i'm gonna go all in and i'm being a content creator so i think that's a that's probably a d i would argue that if you become the next andrew hub you're you're an a like you're a b like you think about it in a world of ai if somebody has a a trusted relationship with you it's a phenomenal business the issue with it is it just doesn't scale so in terms of def it's amazing highly profitable very simple to operate but one of the problems with it is and i would know a lot of these people if you don't show up and you don't bring the fire on the camera every single day and you stop posting your business goes to zero and i think that's a bit of a it's a bit of a prison i think for some people why did you say here from minute is it because of the trust factor or because it's in health or wellness or medical is that the important factor there the niche or is it just the level of trust that people have it's if hub was doing the same sort of podcast but he was doing it about candy he's reviewing candy and if you sell ka it's the affiliate margins are not that good the the candy company won't pay that much to do it if you're doing health like if you think about hub is basically promoting athletic greens health supplements that kind of stuff those things can be very very profitable and the customer lifetime value is high and so he can charge a hell of a lot for advertising and then also i mean if you think about it like hub we own we're friends with with andrew we own a y mate business with him he is able to basically bring i would call it twenty million dollars of free marketing to any business he becomes a part of and so if he takes equity and businesses or owns businesses he grows them massively i mean we took the y business i think it's grown three hundred four hundred percent since he got involved with us alright next one owning real estate so buying properties either cash flowing them or flipping them obviously this is a big space right so this is there's like a thousand variations of how you do this so i think it's a little bit of a tough one but just give me your general thoughts on going into real estate as whether it's multi family leads commercial real estate and saying i'm going to try to buy these properties using some debt maybe i'm maybe i'm just gonna cash flow these properties or maybe i'm gonna try to improve them and sell them you know for a higher higher cap rate you know when when i when i exit the beauty of real estate is predictability i think depending on this sort of real estate i think there's really a big distinction between real estate ownership where you just buy something and you rent it out and then there's real estate development where you actually buy a piece of land or you buy something you add value i remember talking here i think it's your brother law who does the real estate where he he was like look like i know all of the people that you know need space and i just go and i acquire a strip mall and before i close i already know that i'm gonna put someone new in yep and you know it's gonna be a way higher quality asset and then you can refinance it out or whatever to me that's kind of a no brainer way to make money so i i would rate that a c probably alright go and see and why is that not higher because well if you're not really at or you don't have that unfair advantage like my brother law's has the reason i don't really do much real estate is because i don't like anything with a ceiling you know you if you buy let's say you buy a forty tenant apartment building or something like that the rent is gonna be let's say let's say they some old lady owns it she hasn't increased the rent in you know thirty years or something like that you're gonna buy the the building over time you can get an increased yield by increasing the rent but there's a ceiling on that rent and you can't innovate to make more money whereas in a business let's say a digital business like web web design agency or software company you can take your profits and you can actually grow the business and you can increase revenue it's very difficult to do that in real estate without massive capex i think well i think they do the same thing right just go buy and they take the profits so or they refinance and go buy second property what's wrong with that that works yeah i mean you can do it i don't know it's just not something i've spent a lot of energy on i don't i don't think it's when someone tells me that they're gonna go do it i think like of all the things they could do that's a pretty solid approach and i i think the one of the things i've noticed i know a lot of you know really wealthy real estate people and i've been fascinated by how ill it is so you'll meet people who have two billion dollars of real estate yeah but the actual profits that come out of it are like twenty million dollars a year which is amazing right it's made their family wealthy the bank understands that they live a good life but they don't actually have that much liquidity and it's often tied up in the next project and the next project and the next project so i think it's a great way to make your kids really really wealthy and you know ruin a few generations and then they'll buy enough one team and then lose all their money alright we have nothing in the s here yet so i gotta try to get there i i think this is the guy to do it so i have a an icon here of warren buffett and this represents investing so just being an investor generically but i think maybe we the way i was really thinking about this because i think buffett is a little unusual in the way that he's structured his company so really this is to me owning an investment fund or being in the money management business investing other people's money and taking fees and a profit off the top of it is that well no i would argue do a little bit differently i'd i'd say investment management is an incredible business but i wouldn't put buffet in that category because he doesn't actually manage other people's money yeah that's think about sort of the exception here so the distinction i would make let's say your hedge fund manager like my friend bill ac so bill for example he went out he raised hundreds of millions of dollars he bought a bunch of stocks he would go and advocate for these companies to improve and then he would take fees on that and if you think about that business model you actually don't need to really put that much money into it yourself and you can make a profound amount of money if you perform the structure of hedge funds is typically two percent of managed assets plus twenty percent of the profits so let's say that you raise a hundred million dollars and you triple it in a short period of time you can suddenly make you know thirty forty fifty million dollars of carry and fees and stuff so those are really tremendous businesses in my opinion the problem with them is that your investors can pull their cash out and so what bill has done that's so smart and i would rank bill as s and buffett as s and then other asset managers lower they have permanent capital that's the real distinction and that means their investors can't pull their money out they're gonna make those fees no matter what and they can literally i mean if you think about sorry why why is it permanent capital i can sell my berkshire stock today i can sell my per square today what do you mean permanent what's permanent about that part is that or is or are you not talking about that is there some other people you're just trading little stock certificates of ownership between the businesses but what i mean is typically a hedge fund manager would say let's say i give a hedge fund manager a million dollars i can withdraw that capital and the only way that they can give me that money back is by selling stock so let's say that you let's say you're the hedge fund manager you go out you invest in some company the stock goes down i lose faith i say sean i want my money back you have to go sell part of your stake potentially losing quite a bit of money whereas someone like buffett or ac people are just trading the stock certificates right those are just ownership shares sure even when i'm out whoever i sold it to they're in so the the money's essentially there even if the stock price goes down exactly and they if you think about it just in terms of the beauty of their business model buffett is more complex who bill's business for example he simply just goes out and he buys ten stocks and he he has fifty employees and he makes hundreds and hundreds of millions sometimes some years i think he makes billions whoa wait so bill firm only has fifty employees yes fifty employees i think he manages how much is bill act managed so sixteen sixteen to twenty billion somewhere in there so okay let's call it fifteen billion so he's got fifteen billion under management you know what we gotta break the rule we gotta do a little public math here i know he takes a two percent fee or he doesn't take the fee he takes a fee on i think he it it's a blended fee of between one and two percent depending on the full of capital call it a million one point five percent so let's take say he's taking one more hundred percent so his firm with fifty employees whose job is to go and analyze and find ten stocks to own is making two hundred million plus a year in cash flow off of just the fees well you gotta remember so so this revenue yeah cost there's cost to it transaction legal all the other stuff and again i think that number swings around based on the performance and stuff as well right but how high could that cost be he's got fifty employees and is legal he's not doing m and a with private companies he's doing public company investing i believe i mean we don't need to do the public map people can look it up but if you look at per square holdings his public company you can basically see what they pay him in fees every year okay that's incredible so that and that's let's not forget that's no matter what that's not that's not the reward that's not the twenty percent reward i remember i remember talking to him in twenty twenty he was freaking out about covid and he had put twenty five million dollars into a derivatives position betting kind of buying fire insurance against covid dropping the market he made two point four billion dollars of profit or something insane off of that i think it was twenty five million dollar bet and you think about he got fees on all of that like it's unbelievable and he also owns let's not forget he owns like six billion of that capital he manages so that's his money okay that's incredible what about the other side of it were you talked about the hedge fund manager so where are we putting in them so if if buffett and enactment are your first s tier where are you putting the general hedge fund manager money manager who's got at you know assets that's under management but not permanent capital weight i'd give it a i'd give it a b just because of the nature of the swings and you can you're get you're pretty much guaranteed as a let's say you're a very you have a large venture capital fund or you have a large hedge fund you're pretty much guaranteed over ten or fifteen years to make to become a d millionaire almost no matter what which is kind of a a crazy thing about the model but you might get blown up at some point but explain the inconsistency because i believe ac also has like blown up or almost got blown up you know a couple of times what's the difference in your mind between what you're talking about bill keeps getting shot and then miraculously getting back up and i think he's one of the i remember of the investment world hey i mean he has a great line he just says the secret to success in business is just getting back up over and over and over again and what happened to him was bill has made so many incredible investments but i believe in twenty fourteen he bet against herbal life which was an ml and then he also bet on val pharmaceuticals which was a pharmaceutical company that was basically increasing prices it was a very elegant in you know very very smart model but it was run in a kind of unethical way and the company blew up so between herbal life and val pharmaceutical his investors lost faith in him and a lot of them pulled their cash and so suddenly he's his whole hedge fund is blowing up and fortunately in twenty twelve or twenty thirteen bill had raised i believe it was like four million dollar or four billion dollars of permanent capital in per square holdings and bill was able to basically bet himself he went to jp jpmorgan he went to jamie dim who he's buddies with and he got a five hundred million dollar or something loan to bet on himself and buy more stock and he managed to come out the other end absolutely killing it and i think the big lesson for him was don't short stocks because he was shorting stocks and be a lot more disciplined about investing in businesses with leverage or exogenous risks i think there's just funny story bill went out and he bot these little plaques and he puts them on every single person's desk at per square and it's the ten commandments it's like thou shall not short stocks thou shall not invest in a business with too much debt etcetera so bill has really learned the lesson and been through it do you know how in venture capital the sort of the normal vc fund isn't gonna it's basically like a pretty poor performing asset class because you're you're ill liquid for ten years and then the sort of you know the irr that you get out of it is less than if you just kept it in an index fund so like venture capital on the whole is a pretty bad asset class of course the top funds perform pretty well is is is basically a hedge fund management the same distribution or do they on average do better so weren't there's this great story there's this guy ted sides who's a he's a fund manager a fund of fund manager and he had lunch with buffet and he said warren i'll bet you i think it was a million dollars that i can choose a basket of hedge funds and they'll outperform the s and p and i believe he lost that bet to buffet buffet basically said on average funds do not outperform which is very true i mean most hedge funds most venture capital do not perform and i think that's kinda what's distinct about private equity i think i don't know for sure but i think most private equity funds at least have a reasonable return hey quick message here because you know that feeling when you send a wire and it actually works no friction well i've used mercury for years now and let me tell you it just works and that's why use it for not one not two but eight of my companies from credit cards to invoices i have everything in one place there's no junky dashboard i've never told please visit a local bank branch none of that tom fu and a few months ago i landed a big client the first thing i did i sent them a clean branded invoice boom deal closed cash the door that's the kind of banking experience i want and that's why i use mercury so if you're running a startup and you want making that feels like it's built in this century well go to mercury dot com and get started in minutes mercury is a financial technology company not a bank bank the services are provided through choice financial group call man a and evolve bank and trust members fdic alright we got a couple more i wanna do local services so you're starting a local pest control business hvac you know things that are i got the handyman icon here because it is you know something that's that you do with you know a guy wearing boots and overalls that comes to does something in your local area so i would say that's a c those are hard businesses but if you can dominate a local industry let's say like let's say like you really get at internet marketing and you own an hvac business and you're able to hire great technicians there's only so many technicians out there and so they're kind of fundamentally difficult to compete with and i think they're challenging i know a lot of people over the last few years who have bought hvac businesses or plumbing companies and they're like you know guys that look like you and me and they you know they come in and they're dealing with all these blue collar guys and they're like who the fuck are you why would i come and work with you and so i think i think they're they're good businesses if you're like let's say you're a very enterprise hvac technician and you wanna start one of these businesses you can do phenomenally well but i think they're actually quite difficult to operate for a outsider alright i got a couple more venture capital slash angel investing although there they're a little bit different one's investing other people's money one's investing your own no i bucket to them together here i would pay angel investing and as an e i think i view angel investing a little bit like playing ro i like to play poker it has better odds i look at private equity or you're buying businesses more like poker and i i just know i think the classic entrepreneur story that you know we you guys have talked about a million times is you make some money as a founder you wanna pay it forward you don't really get stocks in real estate and businesses or acquiring other businesses they seem like oh or they seem a little too boring a little too common and and you hear jason cal you know i'm the first investor in uber and you know whatever and so you wanna do that same thing and it's a little bit like you ever been pitched by a founder and they have like a pop company and they say like well i know we're like tiny right now but there's this one company that's sold to pro and gamble for three hundred million it's just it's all story driven and don't get me wrong there's amazing angel investors like lucky groom and people that do amazing stuff but i think for lay it's a terrible terrible thing to do with your money yeah it does feel a little bit like golf it's an expensive hobby but if you enjoy it fantastic i'll give you a more part i we we talked about this i think on the last episode or two episodes ago when i first started out i got in the habit of angel investing i have thirty million dollars or something tied up in angel investment completely ill liquid i have no access to it i'd much rather own like stocks in real estate or something alright i have one more here that's buy a local sweaty start oh we have cody sanchez entered the chat here i have i couldn't find a good icon so i just put cody on here for for lack of a better term she's it's a picture of cody at a laundromat and i think she's i don't know i don't i i don't actually know by the way if cody really pushes that you should buy laundromat but i think that's a a a little bit of a narrative i'll use her as a a figure head for this idea that you should find a local sort of brick and mortar a sweaty business you know go buy a boring main street business and you're gonna cash flow then you reinvest the cash flow you buy the second laundromat let me buy car wash and you keep going in that direction where does andrew wilkinson rank that model on the material list i mean i love i love cody and i love nick nick hub i think what they're advocating is basically look don't go and work for someone else when you can create your own job and i think if you can be an owner operator but they don't say that i think if they said that it would be a lot of more of an honest broker right the way you the you said one keyword which is what they say is own your own business and you said own your own job and i think there's a big difference between those two things i think that's a fundamental question you're buying your own job or you buying a business if the business returns more than the cost of the owner's salary then i'd say that's great i'd say that's a c chris and i always say like if you can skip the line and instead of working working your way up and starting businesses you can just buy a already working business and just improve it i think that's phenomenal i mean it's really a lot of what we've done so you know my story i started the the web design agency medal lab that business grew i then took almost all my profits and i started like ten other businesses and almost all of them failed it was really exhausting and at the end of that process i had one business that i could sell another one that was kind of alive but i started ten and i'd put almost ten million or fifteen million dollars and all these terrible businesses if i just taken you know the a million two million a year and just bought businesses and just improve them i think i'd be much further ahead than i am today well that's what you eventually started doing right what you what you did at some point was you guys decided to switch into buying businesses that are already working as your main business to be in and i believe you guys invested you can correct if for wrong i think the initial kinda seed capital was you took something like five or six million bucks from meta lab it's profits and you were like this will be the base and then we'll try to find these sort of compounding businesses that we can hold for a long time what you guys call wonderful business is great and that's what has become tiny the you know the public company today i think the market have something like two hundred something million dollars yeah basically we just started buying businesses in twenty thirteen when we read about warren buffett and we're like oh my god this guy's doing easy mode why are we doing hard mode but to be honest buffett has this great quote i'm a better businessman because i'm an investor and i'm a better investor because i'm a businessman and i think that in order to be a good investor you need to have run or experience the chaos behind the scenes at different businesses and i think the beauty of what we did was we got really lucky so we went to the gym we didn't dead lift three hundred pounds we got really lucky with metal lab and it worked so that built our confidence to go try more stuff then we tried every bad business model you know we did drop shipping we started a restaurant we did a skin cup skin care company like all sorts of dumb stuff we always joke we put forks into new electrical sockets we learned a lot and then we started investing and so what we could do is we could look at these businesses and say oh wow this is actually a really high quality business and i know that because i've operated a similar one and do you remember how much capital you started doing that with once you once you stop starting new businesses you decided to go start buying i think it was like four four or five million bucks we we basically sat down and said okay we're gonna start this thing called tiny i'm gonna own eighty percent you're gonna own twenty percent that was only because i had more capital because i was the one who owned most of metal lab and chris put in five hundred k or million bucks and i put in the rest and that's it we never put any more money in so that's was gonna ask you did was that just a seed did every year oh we found a new business let's take more metal lab profits and put it into tiny or no no nothing i mean we merged so it was interesting so i actually own metal lab myself i own ninety percent of metal app and then my brother and chris and a few other people were small shareholders in it and so that that's what basically i diversified with so i went off and in my family office did all the venture investing and bought some real estate and you know bought newspapers and restaurants and other dumb stuff but tiny itself really just grew from that original amount so that's pretty incredible i feel like i gotta ask you this because i think you get a lot of shit nowadays i think a lot of people go look at the tiny stock and basically you see i think you guys went or you like did this reverse merger and so then the stock basically like shoots up in twenty twenty one i think kinda like peak air at that time and then basically it's just a downward trend since then and i think a lot of people i see on twitter want to kinda look at that and say oh this guy calls them self the warren buffett of the internet and he says he buys these great businesses but what's going on look look at your stock and so they see that and they say man is this guy like many other people on the internet who maybe either overstate their claims or whatever right that's a common problem on the internet i would say just on the whole is that you don't know who's real you don't know who's actually good and so you have this public company that's a little bit of a public score board in a way and people get really r up about that on the other hand and this is kind of like you know the two parts of the trial right you have the prosecution of the defense in a way the other hand you say look there's a guy who took four or five million you know first created this design agency as really successful as a business was has generated you said over a hundred million dollars of profit lifetime and then you took you know four or five million bucks and you compounded that into a two hundred between two hundred and three hundred million dollar business that holds all these interesting assets and you know cool like the stock stock prices go up and down that's not necessarily then be and even if you said look that's how big it was that's still fantastic i don't know a lot of people who are listening to this that have done anything that's more impressive than that you know so i i admire even if that even if your worst case least generous interpretation is the today's current you know stock price that's still pretty damn impressive so i guess like what's your reaction to here's you're sitting there you don't wanna go out there and you know fight all the internet trolls or anything like that but like how do you see this what's your take on this it's pretty funny because like you know we started in two thousand six basically twenty years ago bootstrap this business until twenty three twenty twenty three when we went public and like over last ten years i think since we started tiny we've compounded at like twenty five our our earnings at twenty five percent we do almost two hundred and fifty million dollars of revenue we have sixty five million of arr we do over forty million dollars of eb and chris and i still own the majority of the public company and all these or these are all things you know you can look at the public filings and see if you also we talked about asset management i mean we also own or we manage a two hundred million dollar fund managed by the public company with forty million dollars of it our own capital and that owns aero press letter box all sorts other businesses if we include that that adds another sixty five million dollars of revenue so over three hundred million in revenue across thirty businesses and all the businesses in the fund profitable as well i don't know i'm kinda like if that's failing like sign me up right and and i don't know what to say to the trolls it's like you know don't feed the trolls right well let's take the the the vulnerable side a little bit correct because i i always ask myself this whenever i get criticized and my first reaction is like what the hell are you guys talking about like do you not see do you not see and i wanna like kinda defend myself but at the same time i always ask myself this just for my own learning which is basically like what about this is fair but but what is the fair criticism and i i think that's always been an important question for me keeps me honest because you know look either i'm just gonna ignore it i got nothing from it i'm gonna get mad about it and think they're stupid i get nothing out of it or i mostly you know disregard what i think is the sort of like off base line of thinking but maybe there's you know some things that some part of it that's fair oh it it is fair that i said this it is fair that i didn't i didn't do this or it is fair that i thought it would be x and actually it turned out to be y you know those are some things that are fit right so what would you say is fair criticism about you first of all i just wanna say i really empathize with people i remember watching like shark tank and i'd be like oh wow kevin o'leary you know he sold his business for billions of dollars and then you go read the juicy gossip that you know he he got ten million dollars or whatever the out of that deal and i think it's very easy to kind of have the one blurb and then judge someone and i think before i went through this experience i would just believe what i read on the internet and and you know kind of enjoy it to be honest like i think there's this dirty horrible part of humanity myself included that loves when somebody who's is on an ups wing falls like talk about bill ac like bill bill's is an amazing investor but he's loud right and i'm loud to i'm extroverted i like talk when i'm doing i like i like talking about our companies and everything and it's really really fun to watch someone loud like me fall in the mud right and i i i see this in myself you know you kinda churn and enjoy it like celebrities go through this too where it's like they're awesome and everyone loves them and then all of a sudden you know they like to shit on them for a few years and then they love them again like justin bieber everyone hated him for the last five years now everyone loves them again i i just kinda think that's the course of things and i think it's kind of i just gotta eat humble pie and there's a lot of great things i get out of being loud on the internet and talking about this stuff i've connected with so many incredible entrepreneurs i get to i've made so many new friends you know i i love talking about this stuff and teaching people about business and stuff but this is the price and i'm willing to pay the price and it sucks and and for me it's a button right like when i was a kid i was always i've adhd and like i'd always fuck up and i'd always be the one in our family that was blamed for everything and so being misunderstood is a big button and i really have to resist getting on the horn and trying to argue with everyone because it really doesn't help so i think for me we're just focused on delivering good results and building great businesses which we're continuing to do and people on the internet are gonna twist it however they want to the reality is sixty percent of the businesses that went public in twenty twenty three when we did are still under their ipo price so asana sweet green cup like all these other businesses they're all under ipo does that instantly mean that what the founder has built is invalidate in there moron no and i think that you know the fear the really fair criticism though of us is our business is a bit confusing right even our stock chart like starting businesses so i made all this money from the web design business started a bunch of companies one of those companies became the dominant seller of themes in the shopify ecosystem and chris and i always had it in our head where we're like let's let's take a business public we'd love to do that and so we actually went and we partnered with bill act we we had sold the business we to a family office we bought it back and we took that business public and we took a public in january twenty twenty one do you remember what was happening in january twenty twenty one every stock was going to the moon and so you have this business that's doing forty million or something in revenue and like seven million of eb and it goes to literally the day we took a public it jumps from a two hundred and fifty million dollar market cap to one point two billion and so we didn't take a public at one point two billion but that first day that's where the chart starts right and then the man is over and the chart starts going down and as the chart started going down we ended up deciding hey let's take tiny public so we merge into it so really like the tiny story is this right we've been compounding at twenty five percent from almost nothing and what people see unfortunately because that's what's in the public market is this little you know this little dip down here and to be honest like i get it i think it's like you really have to take the time to understand the business and the story and why the you know why it looks like that but i've encourage people to do their research and actually dig in and understand what we own because from my perspective i think we own a lot of pretty incredible businesses and you you still own the majority of the business i do and is that still you know the majority of your net worth basically so you're i like skin i and how skin do you still have in the game yeah this is what's so funny is like people i mean i've even people have said like oh you did a pump and dump and i'm going like what are you talking about like i've sold almost no stock and the only stock i did one large transfer i think of eight million dollars i moved it to my foundation so i could start doing phil right like right i haven't taken any cash out i still own all the stock and like people will say like oh you're pump and dump or something like i i don't know it's just it's kinda sad yeah and so you you hear all this and you've also talked about this idea of the courage to be disliked you i think you know maybe that was the right the right book at the right time for you during during this period i haven't actually read the book it's killer title what is the thing that i can learn you know from that book so sam just did that great i love that episode he did where he basically said here's the recipe to a miserable life and let's invert and one of my favorite inversion is that you actually want people to hate you you do not wanna be likes by everybody i think that's a great signal that you're doing life wrong and i think if you told me this ten years ago like i would think that's insane i remember i read this warren buffett quote it takes twenty years to build a reputation and five minutes to ruin it and for me i really internalize that i was like oh my god i need to make sure that you know everyone thinks positive of me and right i better protect this reputation then every founder i meet for coffee i have to you know woo them and make them like me or whatever and i really felt that i had to be like consistent and predictable so for example like you know i buy companies and i'm you know i i'm a warren buffett like a wanna be value investor kinda guy but i also really like startups ups i like starting restaurants and all this other chaotic stuff and people don't like that and i remember at the moment like i kind of realized what was going on my dad retired my dad was an architect and he retired and i took him up for a beer and i said dad what what now you know what what are you gonna do with all your time and he was saying he didn't really know and i said well dad i've got i've got money why don't we team up and you can become a real estate developer you can build the things that you've always wanted to build and he goes what do you think someone's gonna say if i suddenly call them up they know me as architect david and all of a sudden i'm pitching them on a real estate development people don't like it when you leave your box andrew and i was like oh my god like i i know that feeling like have you ever had like a a restaurant turf friend who like pitches you wanna a text start they're starting off a sudden or you know your yoga instructor gets their real estate license they wanna sell your house or whatever it is my mental reaction i hate this about myself my mental reaction is stay in your lane yeah i don't like it it makes me uncomfortable i don't know why and it's incredibly hypo critical because like i'm i'm a flip flop i love jumping around i'm an inch deep in a mile wide and so it's like i hate in others what i hate about myself and i realized we're all like prison guards you know like we all have these labels like for me it's like you know i'm an investor and an entrepreneur but then it goes deeper it's like i'm in tech not real estate you know no real estate allowed i'm bootstrap you can't do venture that's weird if you do that i'm pro crypto or anti crypto and these labels kind of lock you into this identity and i've seen this in a lot of big public figures so like do you remember when the ceo of goldman sachs david solomon it came out that he was like a dj right he loves dj right this guy on the weekends and evenings see dj and the press went crazy there's article in the economist about how you know is goldman sachs suffering because he's you know dj well do you think they would have said that if he was playing golf right or like you know we see like kim kardashian get passionate about prison reform we're like fuck you vanity project right jonah hill starts surfing let's make mean memes about him michael jordan plays baseball you know betrayal and so like i realized like our brains are just prediction machines and they get upset when things don't match and so for me like i realized like i don't fit cleanly in a box and it's it's messy like everyone else and so i remember like i was and i started like asking all my friends about this and stuff and i was sitting up at my lake house with a group of entrepreneurs and i talked to the the these guys and i said look what would you do if no one was looking and one of my friends runs this massive industrial business like you know billion dollar business and he says you know my happiest moment is behind oven cooking for people and i actually would wanna start a restaurant and i said would you wanna you just wanna own a restaurant he said no i wanna be the chef of like a michelin star restaurant and he said i i feel like i could never do it though because i so much of my ego tied up and being a business person and everyone think i would that you know i gone insane and and and at the moment i was like no like i wouldn't but when i think about it i would definitely be gossip and going oh my god has lost his mind right you know and so he you know he's escaped the prison and we need to beat him with our baton and you know you see this with like legal degrees bad marriages disappointing your parents you know the industry you've spent twenty years and and the issue is like all these promises were made by the person you were before you know not the person you are now and so i realized like i'm in this quick send i don't know what to do about it and in january i found this book called the courage to be disliked and it's one of these books where you see the cover and you just instantly kinda know yeah you're like okay like this i kinda get it and it's really interesting it's written in this very odd way where it's a dialogue between like this wise old man and a a young a young guy and the core idea is just like seeking recognition as a trap it's impossible to make everybody happy and if you try you're gonna end up living somebody else's life and so you have to be hated you have to have the courage should be disliked and reading this book it was like someone gave me the keys to my cell you know i'm in this cell and there's no walls on either side they're like by the way there's no walls you can walk out and so my new year's resolution this year was i'm done with the like game i'm gonna have the courage read disliked and i'm gonna say what's true for me and so you might have noticed like i've i've been writing a newsletter i'm talking about all sorts of stuff i'm talking about you know having adhd and you know all my weird businesses or whatever and i'm just saying fuck it if people don't get it that's fine and you know i'm gonna keep buying businesses and doing great stuff and on this side item i'm gonna have a bunch of hobbies you know i like that it when i was in high school i used to wear mismatched socks i still wear mismatched socks but i would like i would leave the house and i would be wearing two different socks and i to me i didn't even think twice about it because don't know i was just not even who cares it's just sucks but everybody would comment my mom would comment on about out the the way out the house what do are doing she was like horrified like i can't believe you're doing this i was like what do mean they're it's just they're both socks it does yeah the pattern doesn't matter care who gives us shit and at school people made fun of me for it but they sort of realized like oh we made fun of him and he just continued doing it but also i wasn't even doing it really as like some statement i just didn't care like i just didn't just i just decided not to care about stocks the same way else did and it decided that the idea of matching stocks really didn't matter to me and maybe matter other people more power to you but it just just didn't matter to me and i don't think i realized at the time how important of a like many lesson or trait that would be in the future i remember moving to san francisco and we were self funding or not self funny but like i had basically like a billionaire backers so michael bur was funding like the the lab we were using to do startups ups we didn't take any outside funding but one of our company started to pop and we got i don't know like million users two million users three million users and you know vcs got a little bit excited so there's a investor founders fund that reached out and i took the meeting because i intrigued by peter till and i i don't know maybe this will somehow lead to be meeting peter t so let me take this meeting even though i really didn't want investment and we go in and i start asking you know he's supposed to ask me about the business i'm just asking him questions about founder one because again i don't really care if he investment me or not i'm just here to like learn about them and you know i'm asking all these questions that if you ask a normal vc oh well what stage do you normally invest in answer proceed yeah what's your typical check size answer you know five hundred k to a million dollars or whatever or you know everybody's got like these predefined boxes labels what what what industries are what categories do you invest in b to saas enterprise blah they have these labels that they were like you know and i went to the founders fund guy i'm asking the same questions he's like are we just i don't know we just try to find the you know singular businesses and then i don't know back up the truck like how much money do you need how much money we put in let's get put it how much money you need now then we'll put more money in later what seat what stage who cares just go and so he was taught and he said that when peter started founders fun he had almost like a fight club style rule and the fight club style rule was the only rules is that there are no rules the rules that we set as a fund are going to limit our ability to find the singular business and this is why founder funds are the only vcs to own a shit ton of bitcoin and you know starting twenty fourteen twenty fifteen most vcs couldn't even like bi crypto like by their by laws basically and they didn't even see bitcoin as a like they were so blind on to like we need to find the next facebook right that we need to find the next mark zuckerberg that they didn't think that this anonymous soc na open source project creating a currency like it broke all the rules but that was the thing that mattered and and so founder has had a few of these really contra bets they backed end when silicon valley like at the time it was completely unpopular to back a weapons company it was like so like though the the time they the the narrative at the time was that that was a bad thing in fact google had to shut down their weapons project they were doing they had a big contract with the department of defense google just turned it down because their own employees were like this is not right i don't wanna sign up to be a part of making weapons and killing you know and so the companies you know bowed down and the venture capitalist bowed down and there was only a couple of investors and el gil came on this podcast and he's he said the day i saw that google shut that project down i knew there's a huge opportunity if anyone was willing to go against the grain and actually build a weapons company they were gonna do phenomenally well like it makes total sense for the us we're gonna have a defense department right i think everyone agrees in that and the defense department is gonna need weapons and if the weapons are built by a high tech company that's gonna be better than building low tech old school weapons like this all makes sense and that's when he backed and and founder respond back and so i just saw the payoff you know in silicon valley they call it being contra but what does it feel like in practice i think it's what you're talking about the courage to be like the courage to look stupid right the the ability to think differently right all these terms that have been floating around they all sort of apply to this thing and i i'll share one more story that kinda of reminds me of this which is one of my business heroes is jesse it's and he came you came to one of our hoop group events the the basketball camp we do so jesse was there and jesse was laughing who we were at the table he's just laughing he's like all these guys he's like they're all talking about their like crazy ambitious plans like this guy's building a city this guy's building a religion this guy's building rockets this guy's building this and he goes i'm literally selling a calendar because his his project right now is called the big ass calendar is literally a calendar you put on your wall so you could be a little more intentional about how you're gonna spend your time this year and he's like i think it matters but like in the girls give it this i sell a nineteen dollar calendar you know it's just funny i'm even funny i'm even here and here's the guy who reinvented himself ten times did not stay in any box right started as a white guy rapper then wrote and then that wasn't really fully working out so he writes us a jingle that becomes the new york knicks song he sells a sports jingle company when when he sells the company he gets to ride on this guy's private jet this is amazing starts a private jet company gets involved in a coconut water brand but you know he now hosts a big running event because he loves running he has a son company because he loves son and he basically is just like almost product himself and none of the labels that you you try whatever label you try to apply to this guy like oh he must just be a abyss a brand builder then he tells me about how he you know invest in this like he he decided that water was gonna be really important he bought he invested in like land that produced really pure water and i was like wait so you're an investor he's like well no don't really i don't really care about investing i just and so he was un unbelievable and so i i really find a lot of inspiration and people like this and the the thing that he said that it really stuck with me i was like what are you do after this and you know in this room when you're surrounded by these hyper ambitious type talented people it's very tempting to just be like oh i need to ratchet up the how big my thing sounds you know that i'm working on otherwise i'm sort of low status in this room and he told me he goes oh i think i'm gonna go be an assistant basketball coach with this like local like like like this all black college that's nearby like i wanna go be the assistant coach like i love basketball he's like but dude i was like i was like what are you why assistant basketball coach like clearly not for the money like you know because you wanna get into basketball he's like no dude i wanna be on the bus he's like some of the best times in my life we're on the bus going into a game he's like if i could just be on the bus oh dude that's gonna be good for the soul and i just admire this guy having the courage to be like i'm gonna go do this thing that sounds completely random but as soon as he says it it instantly resonated and like i've i'm actually now an assistant coach for a high school basketball team near me because i was like dude i wanna get on the bus that actually makes total sense to me that was a huge part of my childhood and i would have so much fun doing that even though i don't know how that fits with like the rest of stuff it doesn't really need to fit it just needs to be something i wanna do all that totally resonates i mean i think do you ever listen to invest like the best amazing amazing podcast he has some great guess but there's definitely an archetype and the archetype is be like autistic super genius investor who's like i you know i buy laundry or not laundromat rats let's say you know it's like brad jacobs he's like i just you know i choose an industry and then for five years i buy every company in it and i take it public and then i make you know i compound of thirty percent and then i go do it again and again and again and there's a very clear formula and i have never i've never had a formula and i think the benefit of like there's okay like i i was on kauai hawaiian island and someone goes you gotta go to this donut place they fry their doughnuts and coconut oil and they're these purple doughnuts made of sweet potato and i'm like okay so i go a go and you know it's the amazing delicious doughnuts and i start talking to the guy behind the counter and he says oh yeah we're we're expanding we just we just did one in la and i said what you're you're like a a little tiny doughnut shop on kauai like how did that happen and he goes do you know kevin rose and i'm like yeah i know kevin rose really well what are you talking about he goes kevin kim and he ate these donuts and he loved them and so he invested like ten million dollars in our business and now we're scaling it across the country now kevin is a a fascinating guy i mean last time i talked to kevin he's like yeah i did the doughnut company and then i'm flying to sweden tomorrow and i'm meeting with teenage engineering which is like this audio file company or whatever and then you know he told me about this alzheimer's come this company that's doing an alzheimer's drug he invested in none of those things fit together in a box and kevin is a great example of when i see kevin on a podcast i jump like i have to listen to it like the random show with tim ferris is like my favorite show in the world and both of those guys have been so good at not allowing anyone to put them in a box and as a result they've created this magnet like the guys on if if like i had two options let's say i can be value investor andrew with my formula it'll be very good for raising money i can go and invest like the best i can tell my clean story i'll look like a duck and quack like a duck right there's a lot of positives to that you get less hate easy to raise money you know investors like it whatever but if you're just interesting and you share what you're doing like kevin rose does really interesting things come to you and i would argue like most of our best businesses come from me it's like you know i was a barista and i got obsessed with coffee and i bought aero press i love movies and i i tried to invest in film so i actually like had this period where i was like flying down to hollywood and meeting people and looking into investing in movies and stuff and i looked at it and i was like i'm gonna lose so much money and at that same time i happened to be in auckland with tim ferris randomly and i i was i was in town and i went oh there's this guy who runs letter box there i should have a coffee with him and that coffee literally that i had coffee with matt and i made an offer for the business within four hours so like these things happen randomly and i think you need to create that magnet for interesting people and entrepreneurs to seek you out and i i don't know that anybody listens to you know the autistic super genius talk about his formula and spreadsheet for buying a type of business and goes i wanna do business with that i wanna sell my business to that person maybe there's a certain type where that is appreciated but that's not my jam you know and and you know i'm gonna get my two to three percent hate quota for that and that's just fine by me we're gotta get the haiti either way you think those off you think the the as crowd doesn't get the hate of course they do too right totally you're gonna get the eighty either way yeah if for not getting the hate you probably haven't you knows it's a signal you haven't really done enough yet you haven't how jealous are you of you are you by the way of those guys right i i wish that i could be that focused i wish i get that excited about buying you know waste management business is i i do it but it's just not true you know it's not true to me or you exactly why would be jealous of something that i would be miserable of you imagine my first million if every time you just talked about one vertical right be the most boring podcast of all time did the greatest hack in the world is if you're gonna be jealous be jealous of the inputs not the outputs alright i just sets up the profiles i'd be pull over your car write this down okay listen everybody looks at the result that somebody has in their life and they get jealous of the result and that leads you astra because you don't even really know what it takes to be that to get that to have that right if you're gonna be jealous it's hard so most people try to just turn off the jealousy knob i'm just not gonna do it well good luck with that it's a pretty tough thing to do to really truly kill envy inside you right a certain level of enlightenment and wisdom you need to reach to truly just never feel that envy again so instead just redirect it get en mb of people whose inputs your jealous they're day to day the the work that they do and if you're like man i would love for my day to look like that i would love to work like that not the not the results of the work but the work and so for example bill simmons is a guy like this i don't know how let you know about simmons is a sports podcast but before that he was a he was a blog you know he tried to get hired by newspaper they rejected him so he charts us on boston sports guy blog and he's just sitting there writing about his hometown sports because you know since he was four years old his dad's been taken her to boston sports games and he somehow like blog his way literally to like espn ended up giving him his own section then when he's at espn and he's like i'm not just like and by the way they're he's a call he's a journalist no well he doesn't do journalism he's just writing as a fan so i guess we'll call him a columnist no he's not really columnist him i guess he's a blogger we couldn't by the time they were trying to figure out one label he goes and creates thirty for thirty he reinvent the sports documentary space and he pulls that off and then he gets fired at espn for for speaking his mind and he goes and he leaves and he starts the ringer and it's a podcast network and then i always build a podcast he tells that to spotify makes hundreds billions dollars and there's this great clip the other day that came out of like this big trade happened in the nfl and there's this clip in the ringer office and bill is carrying a microphone and one hand and a chair and he's like basically like jogging through the hallway because he wants to go join one of the other ringer podcast to come talk about this trade that just happened like that's not his podcast he doesn't need to be there he's got all the money in the world he could be on the yacht he could be on an island and he said they're running with a chair in a mic because he really wants to go talk to friends about what's going on in the world of sports because that's what he loves to do so i'm jealous of bill simmons not because he sold his company for a hundreds million dollars or has a popular podcast but because the guy gets to talk to his buddy's about the thing that he loves all day and when he doesn't have to be right and so i'm jealous of the inputs and so you know i think that's a a thing that if more people did you could kinda use your jealousy as more of a compass to figure out what do you really wanna go do i think if more people knew the behind the scenes of a lot of these super wealthy people they wouldn't want that life like the there's a lot of there's a lot of sad very wealthy people as you know and i think the trick is how do you figure out what you're great at and you actually enjoy because there's things i'm great at that i just don't enjoy like sales i love pitching and selling and talking to people or or sorry i'm very good at it but i i actually drains my life force i it's it's misery right and so i think like you know for me i started out headphones on coding ming websites twenty years later i've realized i can write and talk about things i'm passionate about and that creates opportunity which i can then funnel into all my various businesses like i think being a human router and just doing the thing you're great at you're doing this too i mean it's like ben might run all the day to day operations you just get to go and do the thing you've you're amazing at right and it benefits your business in a profound way and i think that's the trick well i i would even push back it's not even that oh man there's always these well people who are miserable there's a lot of other people who were happy doing something that you would be completely unhappy doing i remember when we got bought by twitch and i was like oh you know i get to meet emma he was my boss he's the founder of twitch he did the thing that i had been trying to do he started a tech company it like took over the space that he was in it became like one of the few social networks i was out there that's what i was trying to do before that and you know the guy sold his company for a billion dollars and here he was running this thing and it was like a big part of the internet i think twitch was like on the second biggest consumer of bandwidth or something that year like is it crazy and i saw his day and he was happy doing it which was basically he sat in the boardroom on the ninth floor of the office on a long table and he sat at the front and the coo sat next to him and then teams would come in thirty minutes at a time and they would sit down they would put a memo in front of him he would read it he would ask them questions he would grill them and sometimes he'd be like this sounds fantastic can't wait see what's next and sometimes he'd be like this doesn't make any sense to me and he would kind of rip them apart and then they would be like leave go back they would do a week of work and come back in the next week for their weekly thirty minute meeting with him and that's what he did all day and i just remember looking at that and being like thank god i saw this because this is not what i would want i thought this was my dream i thought like literally what he was doing what he had done was the dream for me dream outcome and i realized like that would be kind of a nightmare of a life and so wait what if that's the nightmare not the dream then what's the dream and then you start asking i you start looking around and he start thinking about what would be and that's when i started the podcast because i'd i looked at tim ferris and others and i thought that sounds pretty fun and so a easy hack because i'm starting a new content project my first new kind of big content project since my first million and the hack the the trick is instead of asking instead of trying to think about what would be really popular what would get millions of views what would get millions of subscribers the better question is what would i have fun doing three thousand times because if i do it three thousand times i'm probably gonna get good at it and i'm probably gonna stick with it and i'm probably gonna get a good result sure but like more importantly like i'm gonna go do it three thousand times i'd better really be like let me optimize for that instead of optimize for what might work let me ask you this are you leaving your your your yourself are you breaking out of yourself is it something that people go wow this is like crazy i it's like when tim ferris launched his card game or he wrote his like he made that weird crypto project is it one of those it's it's i've explored that wide like totally we totally move go make a movie create a broadway play like i've explored all that and there's like things but that's not the active thing i'm working on one of them is i would say different in that it's a different mode to be in so for example this podcast is live it's improvised it's une editing i get on here and i just do me and then don't really think about it after the fact there's a team that basically takes it they edit it they title it they package they send it out there and i don't really think about it again whereas the thing i'm doing right now is a little bit more of a craftsman approach it's like i'm not just gonna improvise it and it's this like you know three weeks later that's kind of gone i'm gonna make a new one it's like no i'm gonna make one thing it's gonna be great but that means i'm gonna really like have to be a craftsman about this and i'm gonna really have to go and take a take a scalpel to this and try to like make it as great as i possibly can which is not a mode i'm normally in that's awesome i mean this it's like a the happiest been in the last ten years is writing my book just headphones on doing something and and actually shipping something that will be relevant hopefully in twenty years that you can go back to if there's something so a fe about podcasting and tweeting and all the other stuff son nice to zoom out totally well andrew thanks for coming on again man always was good to good to hang and yeah you wanna shout out anything your newsletter or anything anything you wanna shout out yeah i mean that's mostly i've haven't really actually been tweeting very much i've been posting on my newsletter and i really love it i sit down like once a month and i kind of do like what tim ferris and kevin do i just like write about all the random things i'm excited about sometimes it's about business sometimes it's about other stuff but yeah people can sign up never enough dot com the newsletters there and i i love it like it's it's been so it's some been so much more enjoyable to just sit down and actually write something formally and take my time instead of like tweeting out toilet thoughts randomly and then fighting with trolls alright man good see you yeah great cheated i feel like i could rule the world 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 looking back hey let's take a quick break i wanna tell you about a podcast that you could check out it is called the science of scaling by mark robe he was the founding ser of hubspot and he's a guest lecturer at harvard business school the guy smart and he sits down every week with different sales leaders from cool companies like cla and van and open and he's asking about their strategies their tactics and how they're growing their companies as you know head of sales or chief revenue officer if you're looking at to scale a company up if you're a cro or head of sales just look at a level up in your career i think a podcast like this could be great for you listen to the science of scaling wherever you get your podcast

Episode Notes

Which business model should you start? Get Andrew's cheat sheet with his full ranking and real profit margins here: https://clickhubspot.com/dge


Episode 762: What’s the best business to start in 2026?

Agencies, SaaS, Restaurants, Real Estate, Marketplaces. Angel Investing; Andrew Wilkinson has played every game.

He built 38 companies, lost $10 million, and still ended up with a $300 million portfolio.

This week, @shaanpuri spoke with him about:

  • the best and worst business models to win in 2026

  • starting Tiny with just $4M (now $250M)

  • the truth behind the Twitter hate on Tiny’s stock

  • why buying companies beats building them

His is not a redemption story. It is the unapologetic reality of building, failing, and getting back up.

—

Show Notes:

(0:00) Intro

(3:06) MLM

(4:28) Freelancer

(5:07) Agency

(9:33) SaaS

(14:48) Restaurant 

(17:03) Marketplace

(19:43) Short Term Rentals

(20:52) Content Creator

(23:06) Real Estate

(26:16) Fund Management 

(35:21) Local Services

(36:36) Investing

(38:12) Sweaty Startup

(43:15) Tiny stock performance

(52:20) The courage to be disliked

(1:10:21) Inputs v outputs


—

Links:

• Tiny - https://tiny.com/ 

• Never Enough - https://www.neverenough.com/ 

• Serato - https://serato.com/ 

• Rekordbox - https://rekordbox.com

• Pershing Square Holdings - https://pershingsquareholdings.com/ 

• Invest Like The Best - https://www.youtube.com/@ILTB_Podcast 

• The Courage To Be Disliked - https://tinyurl.com/5fk3sa79 

—

Check Out Shaan's Stuff:

• Shaan's weekly email - https://www.shaanpuri.com 

• Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents.

• Mercury - Need a bank for your company? Go check out Mercury (mercury.com). Shaan uses it for all of his companies!

Mercury is a financial technology company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., and Evolve Bank & Trust, Members FDIC

—

Check Out Sam's Stuff:

• Hampton - https://www.joinhampton.com/

• Ideation Bootcamp - https://www.ideationbootcamp.co/

• Copy That - https://copythat.com

• Hampton Wealth Survey - https://joinhampton.com/wealth

• Sam’s List - http://samslist.co/

My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano //


Podcast Hosts

  • Sam Parr

    Sam Parr

    Hampton (joinhampton.com):
    My community for founders.
  • Shaan Puri

    Shaan Puri

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