Meet The $250,000,000 CEO Who Sold EVERYTHING

on crystal this business teachable for 250 million dollars at the age of 29 years old and what's incredible is that this wasn't just a one hit wonder his track record goes all the way back to when he was a teenager making up to a hundred thousand dollars in a single day building Facebook apps today we're getting the blueprint to his success why he cashed out and how you can get started creating the next big business on today's episode of subscribe because we're closing in on 400 000 subscribers it would mean a lot to us and uh hey you know what these are totally free it's totally free to do but first we're gonna think today sponsors stream yard and here's the thing in the last episode that we did I dared you guys I said that if you're not signing up for stream yard let me know what I have to do to get you to sign up for stream yard and we got a few comments okay one of them said I dare Jack interview Graham for a podcast and I'll get stream yards oh what's your favorite color I love 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they're really fashionable there's no children or old people here my parents when they were visiting there they found no one within 20 or 30 years of their age everyone here is I would say between 20 and 30 childless and yeah that's that's the Bible yeah yeah yeah this is cool it's my first time in New York yeah it's well crazy here I love New York this is so much fun yeah so tell us a bit of your uh your background and how you got started yeah absolutely so uh I'm a first generation immigrant I moved I grew up in Oman in the Middle East after being born in India so it was a very third culture sort of life because you're Indian yet I've never lived in India grew up in the Middle East and then moved to America for college uh into California and yeah it was a very sort of interesting journey to America but very very grateful to be here tell us about your your entrepreneurial Journey where did that start I think for a lot of people and I was one of them even ever since I was eight or nine years old you always try to come up with these silly little business ideas like I think the first business idea I had is I would tear out posters from a magazine and sell it to my parents friends and some of them were nice and humored me and actually bought it um all the way to a website I designed with my brother I think it's probably age 11 or 12. um it was like a web portal where you could go log on get news all of that stuff never quite launched it but it got me started you know realizing I wanted to be an entrepreneur of some kind um I still remember even then my brother was traumatized but I ended up hiring him as one of my employees I think I was like 12 or 13 and he was three years younger than me he gave him one percent of equity and every time he didn't actually work I would fire him and you know take away his one percent of equity who go crying to my parents yeah he would cry to my parents being like I've lost my one percent or whatever I had to give it back to him but yeah so I've always sort of had the makings of that um before formally taking a plunge but how are you thinking about that like one percent equity at the age of like 12 or 13 like where does that come from well I probably didn't even know the word Equity I just gave him one percent which was kind of mean right you would give him 10 20 yeah one percent is kind of yeah yeah I think it's a combination of like older brother bullying as well like a little bit of that thrown in uh but it properly took the dive into like building a business I think my freshman year of college uh it was the summer of 2007. uh Facebook had just launched the Facebook app platform and I ended up building a couple of Facebook applications and by the end of that summer I started making 10 or 20 dollars a day and that was completely life-changing to realize that you could do something on the Internet yeah and earn a living it was like you know a light bulb went off and since then I you know I've been building different types of businesses yeah where were you at College I was a college in California Berkeley Berkeley yeah and that summer specifically I was interning at Amazon in Seattle I was 18 years old first year first year first 18 years old interning in Seattle as a software engineer I didn't know what I was doing um did not like my team or co-workers I had no idea what was happening right I felt too it was too early for the real world in a lot of ways and and it coincided with this time when you know I had all this time in Seattle and I started you know building Facebook applications and yeah it was a good time you ever have a job before doing all of this like any sort of you know summer jobs or anything you Dove straight at first so that's what's interesting is growing up in Oman in the Middle East there's no culture of like children working you don't actually work until you have a job but my freshman my freshman year of college I was working at a gym very briefly like helping them with their systems or whatever that was like one sort of hourly job but even that was in college got it I'm always curious because you said you went to Berkeley so it means you must have been pretty academic in high school do you think that like there's a relationship between people being extremely academic and then starting startups or do you think that they're inversely related or I think I mean I think there's some kind of relationship but just to be clear I did get into Berkeley but I got rejected from my other nine top schools I think I was I had a really good SAT score but like my academic grades were what let me down when you sort of looked at my college application because I played sport internationally I had great SATs my my high school grades were really bad that was like the one reason really bad I think it was I don't know I think like they were really good until like 7th or eighth grade and then you know you get distracted by life and trying to be cool and all this other stuff and not really studying much and all of that but I would find bad though because I know some parents would be like yeah fair I would say let's say there were like 30 people in the class 35 and like or one of my classes I would be like you know number 10 or 12 or whatever which is not I still got into Berkeley yeah but good SAT scores I see I had a perfect 800 in math and a 700 in English and for my application English was my second language it wasn't really but you know I grew up I grew up Indian and stuff so it was a 1500 which was happy with that's good if anything I think like being good at school probably slightly correlates with you know being good at starting a business but not too much because you sort of have to be a rule breaker a little bit and kind of defy authority I think if you want to be an entrepreneur which doesn't which when you think about the kids that were best at school they were the ones who saw an authority figure and you know sort of followed it so I think you kind of want to have a balance of being smart but also you know disrespecting Authority a little bit if you want to want to start something yeah I feel like there's something there where you're bad at school and you do really well on the SAT it just shows like I feel like that's a pretty good like couple of things that occur that shows pretty high raw just intelligence yeah which I feel like also is probably pretty I feel like for instance I always did better on tests like a lot of people do worse on tasks for me like I typically would do better in an actual test versus a practice test for whatever reason so like I always feel like the pressure is actually something I enjoy and I do better at how do you get accepted by Amazon what led to that I had an interview in college um I thought I bombed my interview that's because I he asked me three questions and I got all of them I didn't find the correct answer but what you do is you talk out loud right it was like solving a programming problem and you just explain your thought process out loud but I left the interview telling my parents being like yeah there's no way this is happening like I bombed it but no uh they actually they yeah they gave me an offer what are the questions I can't remember it's like a programming puzzle that you have to solve and you know I walked him through but I never came to the solution uh but it kind of blows my mind even the summer I actually worked there I didn't do much work at all in fact I can and see I did anything yet they invited me back for the second Summers I think it's also the systems you know the end of the day they have to hire so many software Engineers that once you make it into a big company at some level you're there by default and it was very disheartening as well because while I was at this big company my entire team was working on a single page off the Amazon app like it was a manager inventory page on Seller Central my entire team's purpose was this one page and that was very disillusioning right like that was the first taste of like what it feels like to be a cog in a machine where your entire team just works on one single page um so yeah I think that's that's about as far as I've gotten to working at a large company doesn't it seem highly inefficient to do something like that couldn't one person do that like a day or two that's what I would believe right I mean I think it's like the assembly line right like workers had a greater sense of job satisfaction when they built something from scratch but then you introduce the assembly line where everyone's job was just this one very specific thing and it made people unhappy happy I think it was the same thing at large companies you just subdivide what people are working on to such a small Silo that I yeah kind of was Soul crushing and so you think that actually negatively affects happiness when somebody has like one Soul Focus within a like a like you were explaining a cognitive machine or like yep exactly like I think I think that there was research on this I mean uh where if a worker creates something from scratch there's a sense of accomplishment but if all you're doing is pushing One Nail in so your entire team is creating something you lose that sense of accomplishment you're just yeah you're just doing a very very siled task and can you say what they were paying you at the internship yeah they were paying me fifty five hundred dollars a month wow yeah that was crazy no way yeah that was that how long ago was that that was 2007. yeah College that's that's like what you could graduate kind of yeah and be like a good job yeah but you know what the twenty dollars a day I was making doing things on the internet was so much more exciting than that because the fact that I could sit behind my computer do stuff and get money was it was a light bulb I mean that basically made me unemployable after that like yeah so how did you see Facebook as the next opportunity for that so I was in Amazon I was 18 years old I didn't have a fake ID I didn't know anyone I couldn't do anything for fun um I spent my you know I spent my weekends and nights just had all this free time I had a Facebook account at the time as a freshman in college and you could for the first time build Facebook applications growing up I was a huge cricket fan which not a lot of people know over here but I played internationally that was my like Obsession so I built a fantasy Cricket app for Facebook over the course of that summer and I didn't know how to code super well but through that summer I kind of taught myself everything because I had the objective of building this and by building that launching it making a little bit of money is what sort of opened my eyes to the fact that you could build these applications make money and over the next two three years I just built hundreds and hundreds of apps and basically scale that business out so these are just apps that you would find like on the App Store but then you charge some sort of like subscription service or internet reviews ad Revenue was our primary revenue Channel because then we moved to personality quizzes so you would you would get a notification wait is this the Facebook personality quiz yeah exactly we were at the OG's like we I remember yeah but you were doing this back when Facebook was that it's like hey Dave correct I remember like everyone was on Facebook like 2006 to 2010. it was attacked by like science or was it kind of just like no so so there's this thing called uh which Harry Potter are you there's this thing called the Barnum effect which says that like it's the attribute of us to read a description and to like kind of see how it belong how like you identify with it right and a lot of these quizzes sort of work the same way where you could come up with the description and a lot of people think that about themselves like you could like no matter what you answer in a quiz I could tell you you're mysterious people think they know you or do they really know you yeah the exact same way about horoscopes arbitrary that anybody can be like you know what I'm a Libra you know me I'm a Libra what it was but I read uh someone who's really into horoscopes I read something completely different for like a different sign and they're like yeah that exactly like that's not even yours though yeah the the other thing we found is a lot of people used these quizzes not to find out anything about themselves but to find the right snippet to share so what we would see for instance is let's say there's a quiz which Friends character are you they would take the quiz repeatedly till they got the answer they wanted and then shared it yep so because remember right there's a social aspect of this as well it's not just wanting to know it it's wanting to tell everyone who you are so someone would take the quiz four times they're finally Joey and then they share that one wow so and then it makes everyone else want to see which one yeah so it was a short that is so funny it was a shortcut to learning a lot about human psychology right like as we're building these apps and seeing everything um yeah it was really cool and yeah by the end of that by the time I was you know 2021 um had me drill money through those apps and it's you know opened my eyes to the power of building something how much were those making so a lot of them peaked it like like when they got really really big it only lasted for a few days but it we literally hit a daily maximum of 50 000 a day um yeah and over the course of the apps and like I think it made over a million dollars you know over the few years no some of them obviously were not successful what percentage did not hit and which were those apps like why did they fail ironically anything that was useful and had utility was a struggle it was a struggle like I mean you build a calendar app you build stuff that was actually like helpful to people it didn't really work the things that worked were basically things that appealed to vanity right so friend quizzes worked really well uh which was you answer a question about your friend so you get a notification maybe you get a notification it's like maybe it's a it's a girl be like this girl will answer the question do you think Graham is cute click here to find out what she said and now it'll take you inside the quiz but to unlock her answer you have to answer about 20 other of your friends or you know yeah and you're sending ads to him the entire way well no so there's ads at the bottom but you can also alternatively pay a dollar or do like a dollar worth of activities to unlock the answer without answering the question so it was this idea of a virtual currency where um you know you could sign up for a Netflix trial or do these all these other things to unlock the answer oh it was a snapshot again it's like human psychology and my partner at the time built a very sophisticated system where we would input thousands of questions it would rank each question's viral coefficient because some questions were better than others then automatically update the highest performing questions in real time so it works really well it was a pretty sophisticated system for the time but yeah it was it was a lot of fun I remember something on MySpace where they came out with what was an anonymous question it could have been Facebook but it's when you could you ask your audience a question they could respond back but it's Anonymous you could be like do you think I'm cute and everyone respond I've seen that like I have no idea you stayed far from that because when we tried that there was like bullying and stuff so that was the thing you have to be careful of uh but yeah a couple of things we did that was really good is we once had this uh it would open the app it would predict your best friends and we people would be blown away by how accurate our predictions were and all we would do is look at their photos and see who are they tagged in the most number of photos with it works so well so it's like open this app we'll guess who your best friends are and then people will be like wow how did you figure this out would you manually guess it or did you no no it's programmatics programmatically what it would do is but look at all your Facebook photos it would see who you share the most photos with because all photos were tagged oh okay so we would rank them by who you're in the most photos with so it was very very accurate now that relies on Facebook giving you all that data how easy was it for Facebook it was if you remember yeah remember the whole Cambridge analytics Saga yeah the reason that existed is Facebook gave you everything back in the day you could get all open People added an application you could see everything their friends their friends friends like their photos with their in photos with interest everything so at that time that was all available yeah I had a crazy this is when it really hit me um I think this was early days of Facebook I had purchased with a debit card uh like a deal like an Old Spice deodorant or something like that and then as soon as I went on Facebook right afterwards I'd start getting ads of the Facebook deodorant and I believe it was because I linked my phone number with my Facebook that was also linked to the debit card or something like that and that was shared and they made that connection that Graham just purchased deodorant let me show them this on Facebook and hopefully he buys it again it's wild how do you prevent that is that when I asked like do you want to accept cookies on this page I feel like it's the I feel like no I feel like in the beginning this is like you sign up for Facebook now Facebook now has changed their terms like now Facebook does not give any information to third parties after the whole Cambridge analytica thing I think they realized that parties that were interested could like abuse that data like for us we didn't care like we use it for these quizzes I never saved that data the server space to save it is too expensive like why would I care about it but now they don't give you any of that interesting and you have apple too and it's really cracked down on that for for sharing how do you how did you justify in college when you're at Berkeley staying in college when you're making so much money like you could have just like got that job being an Indian man it's being Indian like every time I talk to my parents about dropping out they're like no just just do it but I I was able to find a good balance I didn't I didn't spend that I didn't go to class really I would study right before midterms and finals I did okay um and I I just was like let me take the path of least resistance which was taking the easiest classes to get my degree but yeah multiple points I'm like I don't understand the point of this and I came close to dropping out but I I you know stuck it through what do you think about like because I feel like if you take the path of least resistance and you still do well meanwhile not working very hard like that's something that schools should appreciate and like celebrate right because that's but that's what I'm going that's what I appreciate about the American system because I went to high school in an Indian high school and there was no substitute for just like doing a lot of work but the American college system there's a lot of potential for being smart about it right you have to hit a certain number of credits but you can go to a professor get credits for doing all these random activities you can choose classes in a certain way that it give you there was a system and like any system any good system I wanted to beat it and you know I found a way to like find easy classes find easy professors like find certain classes I could take over the summer where it was much easier so it doesn't make sense yeah there's a system to consistent to defeat and you know that's what I did is rape my professor still a thing yeah it is yeah I had that at that yeah yeah I was wondering if you just look up music I wonder so I still remember and I wonder if like this is still appropriate but at the time raped by Professor also had attacked with professors that were hot and I feel like today I don't had it used to yeah it was physically attractive spicy like yeah I bet that's probably gone but yeah back in the day they had all that oh my gosh yeah how much would it cost you to develop some of these apps that you were making back then I mean most of it was pretty trivial I built so firstly I built the app that were very simple to do then I would get my roommates involved and they would all create content and we'd you know create would split the revenue and stuff but then in addition to running these apps I would take the source code and sell the source code as well so you're selling pics and Shop I was selling everything yeah so would sell the source code for you know 500 a thousand dollars um so anyone could take that and build an app with it did you not worry that people would just copy your designs and run you out of business yeah but I figured like it's so simple that if I wasn't selling it someone else would so I may as well alter it happen to that did your brother get one percent equity now my brother had no idea for one of my roommates had Equity as I built these different businesses with them and then what happened to that did it just fizzle out did you sell it So eventually these businesses they would like you know application would grow and they would eventually sort of Peter out so there's no Enterprise Value being built so I did sell a few of them but if I sold them it would be sold for like trailing 30 days Revenue 60 days Revenue there's not a lot of Yale um and the other ones just died in natural death eventually it would get to a couple million people and then it would have its moment in the Sun and be be done got it yep what did you do after college so I ran this for a little bit after college but I think around 21 I graduated college at 28 around 21 this was fully done and I spent two years figuring out what I wanted to do so I wanted to start a business tried lots of ideas but it was two maybe three years of just nothing working so probably tried eight to ten different startup ideas at the time uh nothing quite worked somewhere in the middle of that I moved to New York City and then when I was 23 24 started doing a little bit of teaching uh both in person and general assembly and then online on udemy and that slowly evolved into starting teachable but between the Facebook apps and starting teachable it was just a lot of trying things that didn't work were you just living off of the over a million dollars you had earned from all the apps and everything as a comfortable yeah it was comfortable I mean comfortable in the sense of my lifestyle at no point especially then was extravagant like I did not like despite making that kind of money at 21 I did not like Buy anything dumb and you know but it was very comfortable so what was your idea process like for for thinking of different concepts would you just think for a while did you have a notepad writing down ideas I would just try and find something and act upon it instantly because I find like inspiration is very fleeting so less thinking more doing uh but yeah we're all over the place I had a a couple of the ideas were good we just executed them poorly like an app where you could like order your like order toothpaste and stuff that we never quite built the Fulfillment so we just ordered of Amazon and people then just realized they could order to Amazon directly but you know there's something over there we built a domain name registrar to buy your name.com or we had a lot of different ideas but nothing nothing quite work um until starting teachable I want to tell you my two ideas and you you give me your honest thoughts you rank them okay two ideas here the first one I'll get to that one Jack the first one I wanted to create an app that was called parked where people could rent out their driveways yep because I remember in Venice Beach Santa Monica you could not find a parking spot but there were so many empty driveways what if they just have an app where you check in in their driveway you could park there and it charges you per minute so unlike a parking meter where you just like you have to guess it's just charge you for a minute and then uh but anyway there's a there's a company in San Francisco that tried that two of them and they both failed and I thought well if they're doing it and both of them fail yeah I'm gonna fail on that too what do you think of that idea I think it depends on like what you what your goal is right like the reason a lot of startups fail is because for a startup to be viable if you raise Venture Capital you're really looking for an exit that could be billion dollars billion dollars plus and a lot of these turn out to be really nice small businesses good cash flow a few million dollars a year but because you go the Venture route it's not doable so my inclination with something like that is it could totally be a really nice business it's probably not Venture scaled so I think someone could make a nice living off it but it's not the idea I would raise money for I think the company in San Francisco probably fell into the Trap of like raising Venture dollars for it and realizing it's a cool opportunity just not big enough for a venture size outcome got it I think the other issue with that was that a lot of the houses that were in Prime parking locations were worth millions of dollars the liability of having someone park there to earn like you know 10 cents and yes a minute or something like that probably wasn't worth it the other idea that I came up with that I thought was pretty good it was called Truth intel.com where basically it was a Yelp for people where you could go and make a profile for someone else upload their photo and write a review on them like Yelp and uh it was crazy but we started this we had a buddy who did all the coding back and we created the website and we created a fake Facebook account and we just added thousands of people on this Facebook yeah and then we started promoting truth and tell this is back in like 2010 am I doing this for like people I'm dating Friends Business Associates across the world we just thought it would be an interesting concept because there's no uh directory or like review of a person yep it was like a Black Mirror episode kind of like something like that but like my thinking is like okay let's say let's say for dating you show up to somebody they're they're creepy they show up late they're disrespectful it would be helpful because there was an app in San Francisco for girls to read I remember that yeah the goals to rate you they got so much where like if you're a man you couldn't even sign up for it but it was like girls telling other girls about guys they're dating it was like the centralized directory the problem with all these ideas is like one it's Rife for bullying yes it's right for like really bad behavior and two like incentives are kind of skewed right like if you could theoretically like if I you pissed me off I could go there and like kind of hurt your reputation irrevocably for just my own angst or whatever yeah that's why we never went with it yeah uh we the more we looked into it the more we realized that people only write reviews if they're upset if it's ever positive they're less likely to write this like every one positive review you probably have 10 great experiences with their own talk yeah versus you have one bad experience you have one bad view like the ratios are off there so we never pursued it yep yep I thought that would be interesting if there's a way to do it legitimately I always had an idea it was uh you know the unclaimed funds the directory or whatever I wanted to go on there and then figure out a way where I could scrub through all the data and then figure these people's addresses out send them a letter something like hey computer companies do that there are companies that do that do they make just a role in it yeah I was thinking like find a way but like also it's based off of good faith because it's their money already so how would I be entitled to any of that something like you know you could just make a charitable donation because I made you aware of this which is very easy you know just to get all that data contract I get it do they really yeah some guy reached out to me he was an old like an older guy and uh sounded like he was in the 70s or 80s and told me the same thing is like you have a few thousand dollars that's unclaimed that belongs to you and it's not on the website if you search for it or like he told me like this obscure thing but he said he wanted me to sign something with my Social Security giving him power of attorney to clean it on my behalf and I talked to him it's kind of sketchy though right like you don't know what he's going to do right exactly so I said no but I said how about this if you trust me on this one I will pay you but I gotta claim myself and he went on a limb he gave me the information where to find it how to claim it and I paid him what what was it so basically the uncommissioned that was sent to an old address or something like that uh and was never claimed the unclaimed fund is really cool if you guys are listening you can see if you have just any money that was sent to you maybe you moved houses so it got sent back to the post office or whatever it all goes to this one main database where you can log once the identifier you're social or how do they know it's like your name your address and that's all public information too so you can look up other people's names see what unclaimed funds they have where it got sent and everything very easy to search up I thought the hard part about that was that each state has their own process for unclaimed funds no they don't uh no I think they do yeah yeah and so I thought that's what makes it more difficult because um because each state is separate and then you've lived in multiple states what states do you check and I think that that's where a lot of those companies profit because let's say you used to live in Texas when you were 18 and 19 but then you moved to California a lot of the companies I think are just scrubbing every single state and you would never think that check Texas because they're like I lived there two years yeah yeah it's a good business it's hard to scale though and you got and the person has to either have power of attorney or claim it themselves it's difficult to claim I hated it like you have to mail something in and then you have to wait like weeks I think it was like nine to 12 weeks to get your money back so and usually unless it's like more than a hundred dollars it's not even worth it there's plenty they're like four or five dollars on there like you're gonna pay more and post it right I I tried for one of my friends dads I was just looking up everybody in my contacts it was like 12 Grand like unclaimed funds I'm like twelve thousand dollars I texted my friend and he was I was like dude does your dad look man I'll do this for free you know obviously like hoping to maybe get a little bit of money on the back end maybe a few hundred bucks or something and then he he looked it up and it was the exact same name as his dad like oh and what's right near his address different person wow right near where he lived same name as his dad the other guy could probably claim it and they wouldn't know all right it was twelve thousand dollars there you go very well could yeah well actually the socials wouldn't match up oh true so no you couldn't do that but anyways yeah enough on our past business ideas uh let's talk about teachable yeah because that was like the not the end-all be-all but kind of like the thing that really yeah got you going yep absolutely uh yeah ended up I had a couple of courses I on udemy was you know making a few thousand dollars a month teaching but soon realized that when you're on someone else's platform you can't really scale it because they control pricing I would work hard to bring students to my udemy course but then they cross sold my competitors courses all of that made me realize it's very very hard to scale a business so I ended up building again a very simple app for myself and my my buddy Conrad to put our own courses on our own website uh it was a little side project at the time and yeah it worked for us and then we got customer number two three four and six months in made me realize we may have a business um and then went to Silicon Valley ended up raising money for it and Off to the Races we went what was that process like in the beginning when did you what was the moment you realize this could be a business like how much were you making at that time so I think it was when we got our second and third customer at which point the total course sailed on the platform were about five ten thousand dollars we kept fifteen percent so 1500 a month which is but more than that there's the path to scale it that was when I started thinking there may be a business by the time we actually raised money we were I think making about you know four or five thousand dollars a month a little bit more um and we're like okay I think it's time time to go to Silicon Valley and raise around and all that how do you do that how do you just decide to go to Silicon Valley and just so this is where the Facebook app stuff was helpful because I had already gone to school at Berkeley so I'd known a lot of met a lot of investors during my time there and I had a roster of people I could go back to being like hey you know I met you when I was 19 20 years old um are you interested in investing even then it was two months of rejections two months of everyone being really nice saying we love it and not following up until we got our first investor this guy named Matt brezina who did not realize he was their first investor actually he said yeah I'd love to invest um let me know Bank details and I immediately ran Incorporated the company that day went to the Bank of America near my house and replied back and like yeah here's our wire info no big deal um but yeah it was it was quite a process to get our first first what what did that deal look like in terms of like how much was invested and how much did you need or was it I'm wondering why you even decided to raise when it's I feel like a pretty low overhead Engineers are expensive you know like if I were to like summarize it in like one sentence Engineers are expensive I had written the code for the first version of the app I'm a bad engineer like you know like what I built was great for validating a side project you can't build a company with what I built so we had to go out and hire people and you know at the time Engineers were you know maybe a hundred thousand dollars Euro be the starting salary it's gone up a lot since then but even that you can't bootstrap that um so I ended up I didn't know how much to raise I picked numbers I was like oh that's today's one million dollars at an 8 million valuation and we kept shopping it around until someone said yes why is it an 8 million valuation and not a six or ten I can't tell you they're all equally arbitrary uh but that's where we went yeah I feel like a lot of those startups because uh we have our mutual friend uh sebi and a lot of them I hear how do you come to that and it just seems like they all pick like you know 25 million or 20 million 50 million like they just pick these numbers yep uh and raised from that yeah but it's all equally arbitrary right like I had an investor say hey this sounds like a six million dollar deal not an eight million dollar deal I'm like your number is as arbitrary as mine like neither of us can actually justify this uh but for me I kept saying eight until someone said yes and then we went with it how much did you need and what was the runway how much did that give you so we we originally aimed for one and we then ended up getting a little bit more a little bit closer to two but the goal typically is you want to underestimate or say a smaller number so that you can fill it up and go above because if you have too high a number and you don't hit it it's a worse signal but again our round was it took a very long time to get the first check but after that everything else happened in two weeks is that because you could say this other person invested yes investors are like very scared of moving by themselves and when you have momentum AKA other investors are on board and for us one of the turning points was when Naval the founder of angelist came on board and messaged his Syndicate on Angel list yep then the rest around happened in the weekend I think it was like the Fourth of July weekend and like just over that weekend we got everything oh my God what's the average amount that someone would invest in a startup uh so for us we had I would say if I were to guess our average we had a few 25k checks a few 50k checks and a few hundred K checks um that was sort of the typical sort of range do you think that's typical of just industry standard that most people or individuals yes for funds it's it's larger for individuals I think that makes yeah it was sebby that told me that um I think it was one and only one in 25 on average is gonna hit is that true so like you have to on average invest 25 times about one to make up for all the losses yes I mean I think it depends like let's say out of 25 companies what I think it might actually look like is 10 companies return zero um you know another 10 companies return roughly your money back a little bit here or there maybe three return to X but one of those is what will return 10 or 20x or 50x and that's where you make your money when you look at where you make your profits from as an investor it's typically one company or two companies and you could have a hundred companies that have you know returned very little yeah so when you got that initial funding did that last you for like a year or two or like how did you structure that it lost it yeah so I mean that allowed us to hire four people and from that with that you know we had a couple of years of Runway but then at every point we ended up raising more money inbound that we never ever got close to spending all of it in fact over the lifetime of teachable we raised 12 million dollars and we had nine in the the bank when we saw oh my God so once the business started working we ran it pretty close to profitability not fully profitable this might sound silly why raise money when you don't have to because I feel like it's it's much more powerful to retain more ownership than raise way more than you need I think there's a deal structure that works for everything the last round before we sold we raised four million dollars at 130 million pre-money valuation so it means we sold 30 of our company for four million dollars so I would say you're selling so little yes so even then though a lot of investors didn't want to invest in us because we didn't want to sell 20 so I'm with you right if you don't have to sell you can do these weird rounds where you sell three percent four percent where you don't feel much and four million made me feel a lot better about my company's you know cash position so I think there's the other the other thing is I also think it's helpful to have the right investors on board so jumping forward a little with my new company raising a lot of money just from dope people in fact no one can invest more than ten thousand uh but we're raising one to ten thousand dollars from you know a couple hundred dope people because it's nice to have Smart connected Network people invested in our success yeah so how much of that is money versus how much is just getting someone on board that you could pop on a call with them and ask them questions much more that and also like this Army of supporters whenever to help us tell our story got it yeah so grown teachable what was that like once you hired these people how did you find more creators to go on the platform yeah so I mean again like it was it took quite a while to hit any kind of scale it took us almost it took us a long time to get to about a million dollars in annualized Revenue but from that point actually took us quite a while to get to 5K in monthly Revenue but from that point we were able to grow much faster after really figuring how to Market which for us was leveraging other creators audiences we realized something pretty special um and you're a teachable Creator is a lot of our top creators people who followed them and looked up to them were also potential teachable creators so we ran a lot of webinars a lot of events our affiliate program is very big as soon as you figured out that go to market motion we were able to scale much much faster but even it wasn't easy I mean it took many years and you know continually figuring out lots of different things and yeah eventually we got there now I remember something about you having very few creators on the platform but your Revenue was so substantial compared to how many people were on there right what what did that look like yeah so in general we made money from our creators not the students so we would charge our creators on average about 70 dollars a month in software and we made a little bit on payments on average we make about a thousand dollars a Creator a year and from that point on it was just what can we do to acquire the most number of creators and some of the creators made a lot of money like we had a Creator who made you know 20 million dollars and on an average year we'd have you know like tens of creators and make over a million dollars a year so real real money um and yeah and they would still only pay us you know about a thousand dollars a year so it was pretty good value for them since we didn't charge a percentage of sales how long did it take for you to unteachable for it to be profitable we were never profitable we were always close to profitability we were always three months if I didn't hire anyone for three months we'd be profitable it's roughly higher in the car so you're just focused on just growing as fast as possible well you know yeah like so at any I would say our average burn may have been like you know 30 to 50K so that's like three people or whatever so if we were continually growing so if I don't if I stop hiring people for a quarter we'd be profitable in three months that's sort of how we ran and was the goal always to sell eventually the goal was never to sell the goal was the goal was yeah just keep building the company but we ended up getting an offer at the right time from the right people which was this company called hot Mart in Brazil and what I like the most about them is they're a founder-led Founder driven company um like met the founders in New York and yeah just really liked their energy realized we saw the world the exact same way and it had also been at the time almost six years of building the company the timing just seemed right and yeah it was just a match sort of made in heaven but at no point did I you know go out to try and sell the company and we'd never we never looked for a deal the deal found us yeah what were your biggest challenges in scaling people uh it's just like I love creating things but I realized I didn't like operating things as much like I you know creating something is so exciting it's a completely different skill it's a high it's a rush to build something where nothing exists but to operate something to hire managers who manage other people you're so far away from creating I personally find that very challenging I find it hard to get excited about that I burnt out numerous multiple times found it hard to recruit sort of Executives because executives are so different from Founders right a great executive is nothing like a great founder um so that was stuff I struggled with and I think that also realistically probably contributed to making me more likely to sell is the fact that I think I was starting to feel a bit burnt out of managing managers of operating running a company of you know a couple hundred people and you're always dealing with problems versus the excitement of creating something what were some of the problems you had to deal with it was just people man it was always at every given stage it's like the I'll give you an example right so because of the structure we were at if you wanted to do if you wanted to build something new when you're a five-person company you just go ahead and do it now we would have to talk about it in our annual planning meeting which would then have a budgeting process associated with it we'd then work it into our quarterly roadmap and we'd then start have you know so from the time you want to do something cool till it happens is like 12 months or something and that just takes a lot of the fun out of it and yeah and I constantly had this feeling that I am also probably not the best CEO for the company it was also this nagging sense of like not only am I not enjoying this there's someone out there who's an amazing CEO and they should be the one running this and is that I don't know if this is the right word but like bureaucracy within business like that adds all those logistical issues just something that needs to start happening once you go to that level or is it like a government type thing like it's policy honestly I also don't know is this inevitable or not some degree if it is inevitable but I'm not sure again all right my first time running a company if I'm sure I could have done it and set it up in a better way as well some level of process is inevitable but I think we may have had too much and it may have been my causing for all you know right so that's sort of the the stuff that I thought a lot about and to be quite candid I also think I had a lot of ego attached to being CEO then that I didn't just let go like like knowing what I know now if I were to be in a similar situation I would probably walk away and hire someone who's a hired CEO and have no ego about it but the first time you're like oh you know I want to be it's my company I want to be the boss I want to be the CEO um so I think there's definitely an ego play as well what was your day-to-day schedule like back then meetings just meeting the meetings and meetings yep um so I would guess you you know the core like year four year five I'm spending 60 to 70 of my calendar in meetings which was again Soul crushing and yeah all of these things sort of made it when you know when we got closer to the acquisition it seemed more appealing to be able to like have more creative freedom and stuff like that how do you learn how to do all of this is it just figure it out figure it out yeah exactly I think it helps to talk to a lot of people so that's why I raised money from other Founders and it's always very helpful to talk to Founders who've gone through the same process and you know learned from them and then there's also just a case of like iterating you try something it works it you know it and then you get better funnily enough doing this again what I will now do is trust my instincts more the first time around you feel like you don't know what you're doing so you almost listen too much to other people while now I just feel more comfortable that no one really knows anything and you may as well be authentic to what gives you the most energy and trusting your own instincts more and can you say how much you've sold it for yeah I mean again I I'm not allowed to officially confirm or deny a number based on our deal but you know there's an article that says it was somewhere in the range of 250 million dollars that's directionally accurate got it and what was that like for was that a number that we we can't confirm or deny but was that an amount where you're just like holy crap like is this real or at that point I didn't have a number I mean I just wanted to get a fair price for the company and by fair price I didn't want the best price I wanted like the 89 80th 90th percentile price and based on what the business was at the time which was doing I don't know I think was 20 million dollars a year when we were negotiating the deal and 25 million dollars a year when we sold it it was a good price I don't think it was an outrageous price I think it was a pretty good price um and that that's just what the business was worth I don't think it wasn't a number I had to hit like if if we had been a bigger business I would have wanted more or small business wanted less and you can't say exactly how much your stake or equity in that company was at the time no but I mean a good amount I mean it's you know it ended up uh and the deal was half cash half stock because I'm also optimistic about you know what podmark the parent company is doing and and you know on part was treated very very well there and continue to be involved there at the board and all of that yeah so what did you do after signing the contract having it done took six months in between because structuring a deal as you learn there's so much nitty-gritty and stuff and why the day we ended up signing the deal right this is the day like the deal was done um was the day that the stock market had the biggest crash in history because this was when covid was becoming a thing oh man and the day we announced the deal was two days after New York shut down so it was very interesting I'm like I just sold a company for a lot of money yet I cannot leave my apartment since we're in lockdown for the next two months but but yeah overall I mean I think it was a sense of like gratitude and also just like also just recognizing our privilege at the time because at the time New York was going through a really bad wave it was so much uncertainty and yeah it was an interesting time little did you know though that like that lockdown I'm sure for teachable oh yeah or business doubled our business doubled right after we sold the company um do you ever look back and think oh man had I just waited no because he still sold right half of what you sold out but I also don't for a very specific reason and that is like I feel so fortunate for everything life has given me I don't want to be a rich [ __ ] who's like oh man I wish I could have had more like in general like you know there's two paths it can either be so grateful I'm like like life has been so so so so so so good to me that yes could have sold it a different time for more money yeah but like if you're going to talk about all the things that could have gone even better like just be grateful right like you can't even enjoy your wealth yeah yeah like so much so much has gone so right for me to have what I have who cares about you anything else is like yeah I love that mentality I asked Tom Billy this from Quest but when you sold the company let's just say I'm just gonna say a random number could be completely wrong right but if you got 50 million in cash in like another 50 million or whatever in stocks did that money just hit a bank account it was just no I mean so whatever yeah did the whole thing hits and you pay taxes on that later like you say with the most that you had in that checking account before yeah all before yeah I don't know like I'm reading his face and as it starts to Grimace and I'm like okay but before but before uh I mean I can tell it my salary at the time was 150 Grand a year um like tens is like probably like 20K or something like that 20K yeah but yeah so yeah I've published talked about how much I paid myself I mean I was paying myself I think I started paying myself 70 grand then 105 then 120 then 150 and it was at 150 we're like I'm not not making any more dollars as for my salary you went from twenty thousand dollars in a checking account yeah or savings account or whatever to well into the eight figures yep Jack's next question is like if you could express that change in a percentage or a factor or it doesn't matter yeah God how did that how did that change your life afterwards uh changed okay so I mean we're in the house right I was able to like move out of my 400 square foot apartment and buy a house um the things that added meaningful value is family I was able to like oh actually an interesting point so my happiness did not change at all when the money came in the bank it did not change at all um post selling my company but nine months after that when I stopped being CEO I became substantially happier so first sort of lesson was like the money was indirectly made me happy by giving me freedom but the freedom was what actually made me happy um another way that it like greatly improved my life is I was able to like just one see my family a lot more to take the family room like more vacations and like yeah just hang out with my like parents much more and being able to do that stuff for them I think was was really really great but for my own life I think it was I think I heard someone Express this really well where they're like when they had money the best part is it solved the money problem it's not like buying fancy things but it's at no point are you stressed about money you go to a restaurant you're not stressed about like wherever you go like money is just something you don't think about and to me that's been the most valuable thing is I don't think or stress about money and that's something that again I kind of remind myself of because I know so many rich people who have more money than I am but they're still stressed about it they either want more or like upset about how much they pay in taxes or something and it's like for me the money problem was solved and that's super valuable I don't think about it it's it's great and then after selling how did you get back on the horse to build another business yeah so ended up selling the company started started a fund invested and while I was investing I was traveling a ton I told myself I never wanted to start a company again because in my mind I just remembered how hard it was but you know a couple years pass um after a while I realized I missed the sort of meaning I got from building a company and also it's it's a little bit where I do think I'm actually good at creating a business and like you know it's like I'm like an athlete who misses playing their sport I'm like you know that's my that's my thing I I miss it I want to compete I want to you know I wanna I wanna put my hat in the ring one more time and build something super valuable I think this time it will be the last time I do this uh because I want to build something really really valuable but I had one one big swing in me could you tell us more about that yeah absolutely so the new company it's based on my learnings while I was selling my business right before selling my business I hired lawyers and accountants and all these expensive Finance people to help me figure out how the tax code Works how to structure stuff and it made me realize there's a lot of things people don't know about like in terms of how to actually keep the money you make there's this whole black magic that is thus far only been for rich people right whether it's like setting up trust or like how to best leverage retirement accounts and all the these things and I'm like people need to know about this everyone needs to know about this so the goal with this business is to help business owners keep more of the money they make and we'll do that by teaching them how to but also Building Products so we built a product that's a retirement account for anyone who works for themselves and they'll keep building products like this but really things that help people understand this crazy tax code we have and keep more of the money they make all right um teach me let me be the case what could you where would you start just pretend like I am your student right now okay so the first thing I would talk about is like wherever possible I think being a business owner is amongst the most tax advantage thing you can do there are so many benefits right from the fact of like capital gains right like you pay a lower tax rate by owning assets versus cash the worst type of income to have is a salary but within that there's so many sort of different optimizations based on where people are and what they want to what they want to do so again what started very basic but like if it's someone who's making you know 150 000 a year sell playing courses what I would tell them is one you probably the problem you're set up as an LLC they probably want to move to an S corp because they'll save on self-employment taxes they probably want to make sure they're claiming their deductions correctly of all of their expenses right like right from home office internet all of that stuff um want to make go through their businesses there anything they can depreciate if there any real estate tied to their business there's appreciation stuff there's business tax credits and that's for that type of person if you're a startup founder there's something called qsbs which is where you pay no taxes and up to 10 million dollars when you sell your company but you can set up a trust and multiply that to 20 or 30 million no matter what the scenarios there's a lot of crazy stuff and our goal is to teach people how to do that so this is stuff that a good accountant should know yes a good accountant should should know not all of them do yeah um and then some things are the technology so a retirement account for one person like I tried to set one up myself it was impossible which is why we built a technology ourselves where someone is self-employed we set up a 401k for themselves but the cool thing with the solo 401K is you can invest it in any asset you want you can invest it in startups crypto real estate and you can get a 67 000 a year tax deduction uh if you want you can also do Roth contributions which mean it you never pay a dollar of tax on it post retirement and there's no income limits unlike a Roth IRA which is limited to people who make less than 150 000 a year a Roth solo 401K there's no income limit so you can make a million dollars a year and still put in Sixty seven thousand dollars into a Roth 401k using something called a mega backdoor conversion which again is like Niche tax strategy so I did one of those uh last year and it was one of the most complicated like honestly for me just to set up all of the different accounts and get them to communicate with each other and stuff it probably took close to two weeks I got started it was like December 7th and I was like okay like I'm good I have like three weeks nearly four weeks to get all this situated and everything start creating account here create an account here I have to link these accounts I have to wait for this like thing to get settled and then I have to like withdraw the money here it was incredible it was it took so long and I almost didn't get it in time I think I got it on like the last day possible and I had so much money in wire fees for and like crazy it's crazy it's terrible it was so stressful and I hated it wait a minute you made a a Roth no no sorry a yeah the Rother a back door yeah yeah and uh what was the limit on on the 60 on the 401K at 67. no no no what was the limit on the regular Roth IRA uh if you make over 150 000 a year Jack are you trying to say that that was I mean yeah I did um because I contributed to it but yeah that was it was extremely uh yeah yeah also a rock Ira only lets you contribute 6 500 a year but using a mega backdoor Rod you can get 67 000 in so more than 10 times into a retirement account and these compound packs free right so again like there's stories I don't know if you read about Peter Thiel during his Roth IRA to four billion in value right now it was two steps one he bought his Paypal Founders and then that grew to about 20 30 million then he made all his Investments including 500k and Facebook from the Roth but again like these are things and by the way I do think what he did was probably slightly illegal and we tell people like you know this is what he did I wouldn't do it for these reasons but there's such a dark art here that our goal is let's talk about it let's build tools for it let's build a technology apology for it and teach people you know how to keep more of the money they make because when you run your business at least for me you spend so long thinking about your business no one's thinking about your personal finances and that's where we want to want to come in I love that but how would that be different from a competent accountant one we're building technology right we're building like in a complicated like all the accountants we're partnering with they're using our technology to actually set up the solo 401k and as we build more products we're going to use our software to do that and two the education is helpful for all the people who can't afford an accountant so the education it's like it's education is two three hundred dollars a year and you get all this information it's a community it's courses I mean it's education business so so yeah um the technology is really the differentiator where again like accountants will use us but like we'll be a One-Stop solution for you to deposit money do a conversion invest in startups invest in stocks ETFs everything it's a full Investing platform so if someone were to sell their business for let's say some hypothetical number 250 million dollars would they need all of the accountants and attorneys what would they just use here so I would at that scale I like again we still recommend accountants for anyone who makes a bunch of money but as this person is building their business they can learn a lot of things about how to set things up while kind of going through our content but when it's time for the exit I would still always recommend you know an accountant and so forth and does it provide consulting or is it mostly just like education so right now it's education and Technology products I think there's a world where we will find a way to work with advisors as well because I think you can I still am I still think you the human touch is very very important when you're dealing with people's money might be a little bit of uh Ramsay Solutions where he has people that you go through that are pre-approved that know his system and uh he's kind of the broker between the two yep yeah the the big difference is long term we also want to build the best sort of investing platform out there so the fact that right now we just you know we became a registered investment advisor we're soon rolling out the ability with one click to buy stocks and ETFs from the app so it's a full investment platform as well is it is it operational now the company's been around for four months we've rushed out our 401K product because we needed to hit a December 31st deadline so we have you know hundreds of people that set up their 401K product with us already next month we're launching investing uh yeah We're Off to the Races the education product launches in two days so lots of the one downside I will say with a lot of the 401ks is that the investment options are terrible that's why 401K is amazing because all the power for 401k but you decide how to invest it you guys have a referral or affiliate program well we'll give you a link oh yeah oh well if you guys want to check it out all right well now it's linked down below write down in the description maybe a pinned comment yeah yeah that's interesting I I can't remember who I went through or go through for a 401k but I had to set one up as an employee with I think it was a ADP or something like that yeah they're they're Terr and that's the other thing we're thinking about there's a good chance we've gotten a lot of demand from startups and small businesses that say Hey this is dope for my one person business but I would love to use it I started over my 20 or 30 companies there's a good chance we'll end up servicing that demographic as well I think you would need to because that's the big Market there's a lot of Market there and and like a lot of the competitors charge assets under management fees and I think I think AUM fees are a rip-off typically like I think it's great for the provider like we would make so much money if we charged a fee of assets under management but I think it's not in people's best interests not our customers best interest to pay an AUM fee yeah how do you reach new potential customers on that seems very Niche Word of Mouth correct I mean so right now right now Twitter has been ironically enough like where we got most of yeah because I've been sharing a lot of personal finance you know content up there adding about 200 subscribers a day on Twitter and a lot of our early customers Founders there I think our goal with this company is to spend nothing on marketing and honestly just do a lot of Storytelling the content the education all of that I think it's gonna be a big part it also helps that you know with teachable a lot of people in this demographic are people I've worked with before so that that helps a ton when it comes to our investors we've raised money from lots of creators for instance and again we're not at the point of telling ours fully going public and telling our story but while fundraising right I'm like we wanted to build an army of stakeholders all these people that are invested in our success own equity in the company at a really good price so if and when the company does well they own a piece of upside as well that's interesting and what's a day in the life for you look like right now running this company so right now we have an office I love working in person right like we have to work remotely towards the end that teachable and I hated it I like the idea of spending my life on zoom on a video chat it's and if anyone's listening and does that I'm sorry it's just not for me I love the energy of people so I go into the off like my days are pretty simple I wake up I work out I go to the office just hang out there until like six or seven PM go do evening stuff typically and evening stuff evening stuff what's evening stuff you make stuff at me look or in New York city so uh it's anything from like dinners or going out right pretty social so I probably end up I would say doing stuff you know five or six nights a week maybe one night a week wow yeah yeah what time you wake up seven seven yeah still very structured yeah it's pretty structured I mean I'm not going out till 2 A.M and stuff that's a lot of freedom man yeah yeah that sounds like the life right there I love the idea of going into an office I recently got a wework membership you did yeah I'm going to Weaver what it's crazy for my productivity yeah and especially since I've been traveling at least recently like I was in Austin like a week ago and now I'm here in New York then we're going to probably be traveling more this year I figured wework was probably we go every day uh in Vegas yeah like the thing is even though there was a wee work oh there are a couple yeah I literally like I'll wake up and I'm so excited to go to the office like I throw in my backpack there's something maybe it's because it's new yeah 100 and I do think for a lot of people like if you find yourself in a rut it has to do with changing the environment that you're in or just keeping things dynamic because it's so easy to fall into a rut and it's so hard to get out of one and to see that there is like light at the adaptation changes yeah so the thing I'm trying to do a lot of people love doing work in work out of the office three days a week when I'm in New York I want to work in the office every day but what we're trying to see is can we do something like we're working in person for six weeks then two weeks remote which will at least for me like I also want the opportunity to work in different places so um right yeah it's work in New York every day six weeks the next two weeks are kind of remote and then people travel somewhere yeah exactly actually extremely ideal you should consider trying out we were I mean you probably would hate it but you should come with me sometime I would take you until we were not interested they have kombucha Taps so you can get like unlimited people chop the beer on top right after getting anything I didn't know they had beer when we we worked at the wework we worked at the original wework which was uh the one in Chelsea and it was crazy Not only would that have beer on top they had red wine on tap they would have cocktail hour at 3 P.M to come and I'm like don't get my employees drunk at three in the hour they once had mimosas on a Monday morning and I'm like I feel like that's like exactly Fitness those were those were the crazy those are the crazy reworkers those are the years of like summer camp and like yeah and I was like that when Adam Newman yeah it was like and I was like I was so annoyed I was like don't get my team drunk on a Monday morning we have so much to do it's fun though they have like everything that you need so much seating fast Wi-Fi you have to pay for the beer and stuff like that no it's literally yeah you walk in yeah right you go to whatever floor it's usually a big building with three floors and then you just clock in and then you go straight to the coffee of the espresso machines or they have these tabs they have like unlimited Seltzer like sparkling water like not the alcohol type kombucha Nitro cold brew coffee everything now I heard wework was losing a lot of money yeah and then that's why there's no beer on top right so they cut the beer and now they're profitable there's some of my problems they're working on it but at least what I found is for me to go to the office every day I need to have a team there like on Friday like no one came in because like a couple people traveling couple people are working from home then I'm like what am I doing here so for me going into the office only sticks as a habit when I have a team going in by myself I always do it I do it for a few days few weeks and I eventually fall out of it but having a team working every day is really nice what do you think of the current work from home environment it's not for me I think there's work from home can work there's some kind of workers that are very good at working from home there's also a lot of people that don't do much um so I think again it's not for me and it's it's a thing seeing those and the trend is here to stay especially for people that are older with kids and all of that a lot of people don't want to go back what do you think is going to happen to a lot of the the big Tech it seems like there's a divide between like the best Engineers want to work from home and the best companies want people to go in who do you think is going to give first I think you're going to be able to choose your flavor right I think different companies will have completely different cultures and you can find something that works for you for us requiring the office has been 90 of people don't want to work with us and that's been great because the people that do want to go to an office every day it's a very specific type of person and they're an amazing culture fit so I actually like like running a company in person when no one else is doing that I think it's the same thing I think some people say the best engine just want to work from home and I think that's untrue I think some of the best Engineers want to work from home some of the best Engineers want to go into the office and I think that's totally cool and I think companies will just evolve to do different things kind of like what Elon did with Twitter like as soon as he went there he was like yeah we're not having any remote employees you know if you want to be remote you're going to have to send like me a personal application for that and then so many people quit but the people that did end up staying like they're still perfectly functional yeah exactly with 10 of the employees and for me what it comes down to is my life is more valuable building something in person like like forget the productivity part of it like it's just like the sense of camaraderie of like building something together is so much better in person like the problem with remote work is it feels transactional like work inherently is transactional you get paid to perform a service but with remote work it really reinforces just how transactional that whole thing is um but when you're in person just you actually build relationships and that's special and you don't want to keep that what about in terms of productivity do you find there to be a difference between the two or do you feel like the benefits are beyond that I think I'm sure productivity varies person to person like for my job in person is great because I'm not coding for long periods of time but I can totally see if your job requires intense amounts of concentration how it's not great but for my work which is very interrupted driven right which means I have a meeting you're meeting there in person is great because I it doesn't bother me but for some Engineers I get why once in a while you know they want to work from home or all of that yeah I think it's fully based on the role what do you do when you ever find that maybe you don't have the motivation or you just feel a little burnt out do you have a system to deal with that or you just push through uh for me I find burnout to be when I'm doing things and not getting the results typically versus just quantity of work uh but I'm trying to think I mean I haven't felt that way with this company since it's been pretty new but typically for me I mean you could call this running away but just like traveling like changing my environment is like something very good even for a weekend like it's just like book a flight somewhere get out like just just go to a brand new place and typically I find that recharges me any desire to uh have a family settle down yeah I mean intellectually yes yeah uh yeah I do I mean you know it's something that again living in New York I think it's it's very easy to get track you know track uh trapped in a bit of a Peter Pan syndrome where it's easy easy to not grow up and I definitely feel feel that a little bit but yeah I'm 33 now and you know at some point I think that'd be that'd be that'd be good yeah I'll be 33 in uh uh what's two months yeah two months three months it's crazy crazy and I know you were so young yeah you guys are still so what am I doing man yeah yeah geez yeah what's something that you wish you knew earlier that you felt would have would have helped you out starting or creating or running a business I mean I think the idea that I got eventually but the fact that everyone is Faking it like I used to when I was starting a business to think that all these people had you know knew so much more than me and and I realize that's that's not really true everyone really has been is winging it and this time for instance when I'm building a company I'm a lot more confident in trusting my own choices and my own beliefs and yeah I wish it's something I'd internalize a little bit sooner since I spent so much time in my last company trying to do what I thought good CEOs do trying to do what I thought good managers do versus what is it that works for me as a manager as a CEO as a leader who did you look to though just to make sure that was correct or do you just sometimes do what you think is best and see what happens I think at this point like Running Company for seven years and now this and also investing in over 100 companies it's enough to start seeing the patterns um but at the time so now I think it's just I've done enough stuff that you see how certain things play out over a long enough period of time but at the time it was very helpful to talk to a lot of my investors it was you know I raised money from a lot of people there were other Founders it was very helpful to balance stuff off of them but at this point I mean I'm 33 but I've been involved in text and and I was 19 years old I feel feel like grizzled veteran um but yeah yeah where are you investing now are you mostly into startups or do you put money on the side and say like you know I'm doing index funds and real estate so my overall strategy um which I think can be used by a lot of people is uh I barbelled it where I put half of it roughly tracks the s p um and that is my money that I kind of never want to touch that's like generational wealth that's the money my kids and my kids kids and whatever we'll have the other half I'm having a blast with um that is me like doing the stuff I want and 50 50 is I mean I would not recommend a 50 50 allocation to most people it works for me because the the 50 in the market is enough for other people maybe a different percentage but and the 50 I'm investing I would say the majority of it is in startups because that's the world I know I have a little bit in individual stocks which have done terribly since last year and have lost a lot of confidence there uh but yeah but mostly in Tech startups where a lot of it is a tied up in my own funds and then some other friends funds and yeah it's just a world I know very well and what do you look for in a successful startup investment what is it is it just a someone told me that it's really just a a investment in the person yep it's about on the founder and how do you tell a good founder for me typically a good founder um they have a bit of a chip on their shoulder like they really want to prove a point uh they move fast like scary fast like you know it's very interesting when you meet someone then you meet them a second time and you're trying to think of how much they accomplished in the interim uh the third is their charismatic and charismatic doesn't mean like superficially charismatic but as a Founder you have to continually convince people to do things people to join your company people to invest in you people to buy your product so that that combination you know I think chip on their shoulder charismatic moves really fast um I think those are Hallmarks of of a good founder what about the business itself or is that secondary to the person can a good person make any business do well a good person who wants it badly enough will be able to either because the thing is the company you invest in is very rarely what the company stays business models change so much so if someone has a bad idea or idea that I think is all right but they're thinking about it the right way AKA like you know they're fully aligned on building a venture-sized company it could still totally work I want to know about the 50 of the money that you have that you're just planning on having a blast with I mean by blast I mean I mean investing in Higher One glasses it's not that fun it's just like I didn't think like we're talking like clubs you know I mean I mean My Lifestyle I can like literally live the life I want and travel and all it's like none of I don't have like like I'm not flying private I fly business class but even that you know I do through points my inherent lifestyle is actually like like I buy everything I want and it's not a very expensive lifestyle I just don't have super expensive Pace Yeah Tim Ferriss in the four hour work week did a really good breakdown of like if if you want the perfect life add up how much it's going to cost every month and chances are it's a lot less than you would expect for like a really incredible like baller lifestyle like you want to drive a exotic car 2500 a month yeah three grand a month see I personally would love to do that but at the same time I feel like there are way too many moving pieces in my future it's like okay like what is what would my wife want well my kids want you know what I mean so it's like wouldn't really work for me at this time but I feel like you know maybe it's also so much easier without dependence yeah right now independence and I think I live the life I want I travel I think like my entire lifestyle is like it's maybe 10 grand a month which I mean it's a lot but it's stuck that much and I can do everything with that jack it sounds like you're living a life for somebody who doesn't exist yet so no no no I'm being serious what does that mean I don't understand no no that means you're like living a life like you're not living your life now but you're trying to live it in the future if that's what you're worried about that sounds very Alex hormozi-esque coming from you Alex yeah I'm a big big philosopher so you're saying well what are you saying exactly so I'm saying like don't don't sabotage yourself to the point where it definitely hinders what you want you know wife and kids and a family um but don't worry about that necessarily now 100 because you're not going to go out and get those experiences good point I actually like the point a lot yeah I agree with that I appreciate that yeah it's hard to like to I know I've made a good point no I think that was a great point because I'm always acknowledging I'm kidding I'm always acknowledging like what I I think my future self would want but the thing is I always tell other people this it's like it's generally don't spend too much time planning what the right you want the rest of your life to look like because chances are it's like something's gonna happen and there's just gonna be like a wild turkeys set yourself up in a position to embrace Serendipity and everyone Point that's wow that's a quote right there that is a quote huh was that your quote or did you I mean yeah uh but again I don't think it's a particularly unique or novel thought but yeah I think I think the idea that you want to set yourself up to embrace Serendipity like for me that's why long-term travel was very helpful in terms of yeah you just realize you can when you're traveling a lot especially through countries that are not super organized and stuff you realize there's only so much you can ever control and you truly get good at going with the flow um yeah so I was all very grateful for the time I spent in between you know teachable and and starting this just to spend some time you know traveling and hanging out how'd that change your philosophies on things it sounded like you didn't really do much before you know selling and then you had the time I would travel before selling but I would travel like the way an average American person does which is like you take a long weekend you stitch together two days and you go on like an overly ambitious five-day trip which is very different from like last year I left New York for six months and right and I was just like okay I'm just gonna go to random places I went to Mexico for a while then I got a car and I drove around like the Balkan countries like former Yugoslavia for like almost two months and just Embrace these experiences but it was really cool I mean I think one of the things I realized is like people around the world like I was at a surf camp in Brazil and everyone around me there was just so happy every single day like the surf instructed the people around there and then I compared them to like my friends in New York who are like smart successful people running through businesses who are like sad and like you know like feel strung out and and you just look around and you realize that like we spend so much time in our lives seeking like the I don't know like success or work or all of that with this idea of like at some Future Point whether it's when you're retired or whatever that you'll actually be able to enjoy everything um so yeah I just took some time off and I'm like what are all the things I would do if I was retired let me just do them now and see you know what it is that actually brings value to my life and if you could distill that into a few things what would you say those are for me it was very simple I like spending time outside every single day like getting sunlight every single day is super important to like moving my body I'm a crazy person I walk 20 000 steps a day and have episode started traveling so that stuck with me yeah I do my calls and I walk I walk how do you like how do you get those steps you just go for walks uh no very little treadmill I yeah I do any meetings I have that are one-on-one or phone calls I do walking meetings I love that yeah I don't do I like that we Jack and I used to go for a run yeah and we come up with some of our best idea is going for all right I I also can only think in motion I can't think when I'm like sitting at a desk there was a study that was actually done that proved that is if you're if your body is physically moving forward like you're taking steps that way like your brain will work at a higher efficiency I need to Pace um the third thing third thing was meaningful social relationships like again it's not about um quantity but quality of relationships and the fourth thing was work where I felt like the work had purpose and that was what was missing until I started this company I felt like when I was traveling I had three out of the four um but the work with the work with purpose was missing but yeah I realized after all all that time only these four very very simple things are the only things that meaningfully move the dial on what it is that like gives me a sense of fulfillment everything else is noise so how do you find the time to balance between your work right now and traveling uh trying to find the right balance but again as I said a lot of companies will say you got to come into the office two or three times a week what we're trying to see is if we can do six seven weeks at the office then a week or two where people can work from anywhere so trying to find the right balance we're also doing team Retreats we're taking the entire team to Mexico City trying to see how we can you know build that a little bit into our culture I love that six weeks on two weeks like kind of like travel working yep I definitely feel like I can Implement that right now yep that would be what would you what would you think about it you'd be fine with a gram six weeks where we just like grinding well we have just it's the last minute guests that make it difficult if I go east though I can make it back because the time difference I would say as long as we never have guests that are booked out usually more than 24 hours in advance I can make that easy yeah I would say I don't care as long as long as you can make it as long as you could make it back for a guest uh within probably 36 hours because we never have anywhere that's like hey I'm only here for the day and if we do right we got you know Alex and I will take care of it for you cool we'll cut you out of that one yeah beautiful yeah this right here I notice you guys have a great bookshelf or you have a great bookshelf you do a lot of reading yeah I've been uh reading a lot first when I was very young and then there was like a dark period of seven or eight years but then for the last five six years I've been reading a lot again um it's it sounds very silly but five years ago I created a spreadsheet and every time I finished a book I put it in the spreadsheet so now I have this record of every book I've read in the last five years and but that mechanic made me read much more since it gave me this little little sense of completion um so I gamified it and yeah I ended up reading a lot more you know I did the same thing but with gambling [Laughter] yeah I made a spreadsheet to track my wins and losses and uh I told myself I think I started with 500 bucks and I said when this is all gone I'm never gambling again and just to you don't know me but just to give you a frame of reference I don't go out and gamble but it's like more like oh friends are coming over and no because I wanted to be like all right I want to [ __ ] gamble 500 bucks in my life and then once that's gone yeah it's gone and uh no once it's gone you'll be like well I can always make it back so we're still up right now so we're up about uh about twenty eight hundred bucks oh wow for Alex it's investing yeah and so Alice wins like every time sports betting or no it's literally just either blackjack or mathematics there yeah 100 we went and played roulette Alex and I he put in five dollars and at its high it was at like 250. like you do realize in what even if you do a one to one that five dollars yeah yeah and he was at 255 I don't recommend anybody do that like this is literally just like that's my YOLO yeah it's only gambling if you lose exactly exactly I'm also this is uh off topic but uh I love building stuff how much did did these shelves cost you to put in because they're they're they're awesome they're really cool uh it was I think it was about ten thousand dollars um but they're fully measured to yeah there's a ladder over there oh with the ladder that's cool I like the ladder yeah so so you said you read 50 books a year I aim for 50 books a year I was at 41 last year this year we're off to a good start we're at nine already and it's pretty early in the year um but yeah I I read every almost every night it's part of the part of the daily routine for how long it depends could be five minutes if I'm super sleepy if it could be two hours if I'm super into the book I'm reading so you do it in bed yeah and and while traveling traveling like planes and trains all that and how important do you think it is to be a reader because I know from some people I I very much respect they always say like okay like honestly reading books is unlike any other place like yep way that you could educate yourself I think that it's it's extremely beneficial what do you think I think reading makes you a more interesting person I don't think you need to read to be successful at business and in fact like as someone who likes reading I think too many people spend their time trying to read all the business books and they don't actually end up reading like literature or fiction or other stuff so what I try to do is I try and balance it all right yes I'll read some books that are helpful or can you know are like the startup books and stuff but I think too many people are very one-dimensional in their reading they read just to get an edge while I think it's important to read so you learn to love to read you find authors you love to read and it becomes a thing you do to enjoy I think it makes you more well-rounded and interesting person so um I think reading makes your life better and you should find books you love to read what are your favorite books so my favorite like some authors I read everything by murakami uh last year I found this author ishiguro um probably mispronouncing his name another Japanese author read everything by him so what I'll do is I like find an author and then like write like something then you know read everything by them I think when I got into reading really like Hemingway Bukowski like sort of some of the classics over there um but yeah I try to be pretty diverse in in the stuff I read so I would say I read like half fiction half non-fiction all over the place you watch YouTube videos or Netflix or something or is your entertainment very little I mean I watched I watched a little bit of TV uh not that much probably more Sports than then then traditional TV but yeah interesting so basically you just swap out what other 33 year olds would be doing on like Tick Tock and YouTube shorts where they don't retain any knowledge I know I do a little bit I mean I've definitely like opened Tick Tock and been like where have the last two hours of my life gone I mean I'm not I've not not had that experience but yeah I do try and limit that I love your passion for reading do you think that there's a difference between reading and audiobooks or do you think that I can't do audiobooks I literally cannot do audiobooks my brain is just like in a different world like for a while I'm like oh when I'm at the gym let me listen to audiobooks but I just Spotify like yeah like music Spotify wow yeah for me I just do audio books or if I could find it on YouTube I'll just download it on YouTube and listen to it 2x speed interesting my brain can't keep up I just zone out I think all this stuff and then like what were they saying for the last two minutes yeah I'm with you on that because the thing is if you're if you're audio booking that means you're probably doing something else hence why you're audio booking in the first place like you're at the gym so you're working out or you're driving so I'm focusing on the road but I usually just zone out and figure you know focus on the actual attack is that zoning out by the way is very helpful a lot of my ideas come in that period of when I'm walking listen to music and zoning out so zoning out is actually like a good thing so yeah audiobooks are not for me what's your favorite book over here have to pick a single one yeah I really enjoyed there's a book there by girl never let me go it was it's a little black mirror-esque and that was really good but pick one that I read recently and so you got to fill out these tops shelves and yeah there is there's a long way to go I've been I think I probably I buy a lot of books probably by like I would say on average 20 books a month and it's still no way books are so cheap relative to what value you can get out of it a ten dollar book can give you an amazing five six hours and like lessons you retain for so long five okay five six hours to read a book is uh it's pretty fast there's a big very I mean yeah yeah like I mean I would say books books can take anywhere from three to Thirty you know like yeah but I would say five six is probably median hmm you fast reader I'm a fast reader yeah yeah yeah I remember books when I was at school take me like weeks to read the thing like a month to read a book yeah it'd be so bad with it have you wanted to write a book I feel like you would do a great job I do want to write a book but I want to write a book as in for the art of writing right I don't want to write a book in the way that well actually I do want to like there's writing a book to use as a marketing funnel and just writing a book to like like the art of it both are probably things I would want to do for different purposes but yeah part of me my like dream like in a different life is to sit somewhere and try and write fiction I think it's gonna be super cool that's something I just do for fun you know it's not not for the business of it but I think it'd be really fun that's interesting for some reason I imagine you writing a book on like startups like uh Alex yeah I mean there's a world I would write a book on Personal Finance but that would be for be related to work that wouldn't be purely for passion but I could see that as well but the art of writing itself is interesting to me and I you know I would probably write a terrible novel at some point in my life So eventually when you do let's say well I shouldn't assume that you're going to sell whatever company you're working on right now but I don't want to we want to our goal the company that I'm super inspired and motivated by um is Charles Schwab because they're the last sort of big company to come into the space they were founded in 1975 they're now with 150 billion dollars and they change an entire generation's relationship with their money they became a trusted brand so our goal is to build something of Charles Schwab's side is an impact so I thought Schwab was a lot older nope they're they they're like all the other banks are like 150 years old Schwab 1975 they're the young kid on the Block and what would you do let's just say if you were no longer affiliated with this business um again like go back like just think about one of the things that make me happy go back to those four things right like continue like Define meaning in like all the you know traveling spending time uh with my family continuing to just find ways of becoming better it was very clear early on that pure Leisure is not that fun right like at no point like it's pure leisure not that far if that fun for three days but I've I feel like I could pick any activity it could be I don't know it could be surfing it could be a sport and get super super obsessively deep about it um I definitely have that tendency like last summer I joined a tennis league and I haven't played tennis in a while and I wasn't even very good but then I got pretty good over the summer so I can you know pick anything and obsess over it so I think that's that's quite possible so anything you found that's not worth the experience uh of s cargo uh uh like it's okay like a thing that I think is overrated like are a lot of like very very nice restaurants like I like in Mexico City I went to like some of the nicest restaurants and a few times after we went to taquerias right after and like enjoyed the food at Taqueria as much more um so yeah I think I think when it comes to like luxury experiences I think so many of them are so overrated and not sort of worth the price to pay for them I agree with that 100 people made fun of me for this uh you know who exactly who you are I say as soon as like a meal eclipses like the 20 range as long as it goes above that I honestly think the food tastes worse I feel like there's something about that 10 to 20 range of food that's just like the best I feel like that gets you 80. partly orders now over twenty dollars not New York New York double double steak Bowl not even no block is now 20 and 40 cents so they charge for double steak now 20.40 my friend got the same bowl with Wok 23 or 24. that's stupid so yeah 20 gets you nothing okay well yeah so adjust it for the subway I don't like the food there in general but I do like that price I think that in that price range if you just go to like a random place in this corner you know like they're gonna have good food if you get like a 40 to 50 Burger I honestly think it just starts tasting weird like the Burgers start getting tall no one wants a diet burger and forty dollars cool [ __ ] down I hate doing that because then you ruin like all the art that went into like building out exactly but you also like have to basically you get lockjaw when you're trying to take your first bite of it you know it doesn't fit that's true yeah and it all ends up coming out the back anyway somehow the fun just disappeared it's almost weird no I'm usually left with like too much fun like mine at the very end is like this much meat really that much fun I do yeah I mean the one thing I do miss by the west coast is in and out so I am jealous that you have that I mean and that's very good yeah yeah and you can you can specify the ratio like I typically get a four by three four meat three cheese it's great it's probably still like seven dollars why do you not like just make it happen yeah no I should consider that yeah yeah you know what I want to ask this last question what's your brother up to oh that's a great question my brother my brother's chilling he's uh he went to he just graduated business school from McGill uh he's now living in Toronto and working in Tech and yeah that's the other thing he and I have gotten to spend and so much more time together um over the last few years since he moved back to the side of the world um but yeah he's great is there ever like a rivalry between you guys now I don't think so I think like again we our relationship has grown so much and like I still I still talk my entire family so often I talk to my parents almost every single day I talk to my brother almost weekly like we're we're very very close as a family and yeah it means a lot that's cool well thank you so much I really appreciate it a great episode nice meeting you thank you for hosting us yes beautiful home oh also we got a free stock and also you can have me on Instagram will be down below in the description your your links and everything thank you guys for tuning in and thank you next time I love that behind the scenes can you flip your mic on YouTube gram can you flip your mic oh it's a face the other way yeah got it bigger I'm sure all right here you go so see how the glue goes this way okay now flip Andrew put this at the end okay okay no you have Road Wireless goes there the same thing yeah there you go oh look there you look great yes thank you