The Iced Coffee Hour - Meet The $250,000,000 CEO Who Sold Everything

Episode Date: February 14, 2023

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Don't miss the Devil Wears Prada 2 in theaters. Merrill Street, Anne Hathaway, Emily Blunt, and Stanley Tucci are back. In light of the recent scandal, I'm here to restore your credibility. I did not hire you, and all I need to do is find my time until you fail. On May 1st, icons. I'm going to make something of this job. Rain. Be the bridges I burn.

Night my way. Forever. I just love my job. Get tickets now. The Devil Wears Prada 2 in theaters May 1st. Directed by David Frankel. Onker sold his business, Teachable for $250 million 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 $100,000 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 hey, you know what?

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My name is Encore Knockball. I am, I was the founder of Teachable, and now I'm the founder of Ocho. We're here to help business owners build wealth. Thank you so much for doing this, man. Thanks for having me. This is my first time in Brooklyn in quite a long time, and I'm shocked how, like, trendy everyone is. I was telling Alex on the way here, like, everyone is under the age of 35 and really fashionable. There's no children or old people here.

My parents, when they were visiting, 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 the vibe. Spence and more time. Yeah, yeah, yeah. Yeah, this is cool. It's my first time in New York. Yeah.

It's crazy here. I love New York. This is so much fun. Yeah. So tell us a bit of your background and how you get started. Yeah, absolutely. So 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. You had never lived in India. Grew up in the Middle East and then moved to America for college to California. And, yeah, it was a very sort of interesting journey to America, but very, very grateful to be here. Tell us about 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. actually bought it all the way to a website I designed with my brother. I think it's probably age 11 or 12. 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. 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 1% of equity. And every time he didn't actually work, I would fire him and, you know, take away. He's 1% of equity. He would go crying to my parents. 1%. Yeah, he would crying to my parents thinking like, I've lost my 1% or whatever, I had to give him back to him.

But yeah, so I've always sort of had the makings of that before formally taking the punch. But how were you thinking about that, like 1% equity at the age of like 12 or 13? Like, where does that come from? I probably didn't even know the word equity. I just gave him 1% which is kind of mean, right? You would give him 10%, 20%, 1% is kind of mean.

Yeah, I think it's a combination of like older brother bully. as well, like a little bit of that thrown in. But I properly took the dive into like building a business. I think my freshman year of college. It was the summer of 2007. Facebook had just launched a 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 a day.

And that was completely life-changing to realize that you could do something on the internet and earn a living. It was like, you know, a light bulb went off. Since then, I've been building different types of businesses. 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. Your first year? First year. I was entering in Seattle. As a software engineer, I didn't know what I was doing. Not like my team or coworkers. I had no idea what was happening. I felt too, it was too early for the real world in a lot of ways.

And it coincided with this time when, you know, I had all this time in Seattle. I started building Facebook applications and yeah, it was a good time. You ever have a job before doing all of this, like any sort of summer jobs or anything you dove straight at first than this? So that's what's interesting. It's 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 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. 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 there's a relationship between people being extremely academic and then starting startups, or do you think that they're inversely related? 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 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 high school grades were really bad. That was like the one reason. How are they bad? I think it was, I don't know. I think like they were really good until like seventh 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 was fine bad though, because I know some parents would be like you got a fee plus. Yeah, that's a good plan. Yeah, fair.

I would say, let's say there were like 30 people in the class, 35 in like or one of my classes. I would be like, you know, number 10 or 12 or whatever, which is not bad. And you still got into Berkeley. Yeah, but good SAT scores. What was the SATs score? 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. That's good. 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, 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, 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 a couple of things that occur that shows pretty high, raw, just intelligence. Yeah. Yeah. Which I feel like also is probably pretty indicative of... For instance, I always did better on tests. Like, a lot of people do worse on tests. For me, like, I typically would do better in an actual test versus the 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. I thought I bombed my interview. Because 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, they actually, yeah, they gave me an offer. What are the questions? I can't remember. It was like a programming puzzle that you have to solve and, you know, I walked him through,

but I never came to the solution. 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't say I did anything yet they invited me back for the second summer. So 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 Cellar 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. So yeah, I think 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 believe, right? I mean, I think it's like the assembly line, right? Like workers had a greatest sense of job satisfaction when they've 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. 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 with soul crushing.

So you think that actually negatively affects happiness when somebody has like one sole focus within a, like you were explaining a cognitive machine or like with the- Yep, exactly. Like I think, I think there was research on this. I mean, 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 silo task.

And can you say what they were paying you at the internship? Yeah, they were paying me $5,500. dollars a month. Wow. Yeah. Oh my. 18. Yeah.

That was crazy. No way. Yeah. How long ago was that? That was 2007. That was old. Yeah. College.

That's like what you could graduate kind of. I know. And just get that and be like a good job. Yeah. But you know what? The $20 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 a lightball.

I mean, that basically made me unemployable after that. 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 idea. I didn't know anyone. I couldn't do anything for fun. I spent my weekends and nights.

I 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 obsession. So I built a fantasy cricket app for Facebook over the course. 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 open my eyes to the fact that you could build these applications make money and over the next two three years I just build 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 add revenue was our primary revenue channel to then we moved to personality quizzes. So you would get a notification.

Wait, is this the Facebook personality quizzes? Like that's the must be done. Yeah, exactly. We were the OGs. I remember. Yeah, but you were doing this back when Facebook was at it as like hey day. Correct. Correct.

I remember like everyone was on Facebook, like 2006 to 2010. Was it backed by like science or was it kind of just like? No. So there's this thing called. 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 like oh that kind of is me i think the exact same way about horoscopes i feel like horoscopes are just so vague and like arbitrary that anybody could read one of those things and be like, you know what, I'm a Libra, you know me, I'm a Libra. I know what it was, but I read, someone who's really into horoscopes, I read something completely different for like a different sign and they're like, yeah, that is it. Like, that's not even yours though.

Yeah. 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 friend's character are you? They would take the quiz repeatedly till they got the answer they wanted and then shared it. 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 shared that one. Wow. 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. Yeah, it was really cool. And yeah, by the end of that, by the time I was, you know, 20, 21 had made real money through those apps and it just, you know, opened my eyes to the power of building something. How much were those making? So a lot of them peaked it, like, when they got really, really big, it only lasted for a few days, but we literally hit a daily maximum of $50,000 a day.

Oh, wow. Yeah. And over the course of the apps, 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 do they fail? Ironically, anything that was useful and had utility was a struggle.

Like, I mean, you build a calendar app. You build stuff that was actually 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, which was you answer a question about your friend. So you'd get a notification. Maybe you get a notification. It's like, maybe it's a girl.

It'd be like, this girl answered a question. Do you think Graham is cute? Clicker 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, pay as a... And you're sending ads to him the entire way to.

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, you know, you could sign up for a Netflix trial or do all these other things to unlock the answer. Oh.

It was a snapshot again into 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 are better than others, then automatically update the highest performing questions in real time. So it worked really well. It was a pretty sophisticated system for the time. But yeah, 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 ask your audience a question. They could respond back, but it's anonymous. And you'd be like, do you think I'm cute? And everyone would respond back. I've seen that. I've no idea who it is, though. We 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.

But yeah, a couple of things we did that was really good is we once had this. You would open the app. It would predict your best friends. And 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. guess who your best friends are.

Then people would be like, wow, how did you figure this out? Would you manually guess it? No, no, it was programmatically. What it would do is it would 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'd rank them by who you're in the most photos with. So it was very, very accurate.

But now, that relies on Facebook giving you all that data. How easy was it for Facebook to release this? Remember the whole Cambridge Analytica saga? The reason that existed is Facebook gave you everything. Back in the day, you could get all, when Facebook, If people added an application, you can see everything. They're friends, their friends, friends, like their photos, who they're 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. I think this was early days of Facebook. I had purchased with a debit card, like an old spice deodorant. It was something like that. And then as soon as they 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 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. Hopefully he buys it again. It's wild. How do you prevent that? Is that when I ask, like, do you want to accept cookies on this page? I feel like it's the cookies. I feel like in the beginning, this is like you sign up for Facebook.

Oh, really? Yeah. Facebook now has changed their terms of, like now Facebook does not give any permission of 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. It's really cracked down

on that for sharing. 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. It's all being Indian, man. It's being Indian. Like every time I talk to my parents about dropping out, they're like, no, just do it. But I was able to find a good balance. I didn't, 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. And I just was like, let me take the path of least resistance, which was taking the easiest classes to get my degree. But yeah, at multiple points. I'm like, I don't understand the point of this. And I came close to dropping out, but 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 school should appreciate and like celebrate, right? Because that's what I appreciate about the American system. Because I went a 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've 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 gave you, there was a system. And like 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. That doesn't make sense. Yeah, I looked at it as a system to defeat, and that's what I did. Is rape my professor still a thing? Yeah. It is. Yeah, I had that thing.

Yeah. It's wondering if you could just look online and see it. I wonder, so I still remember, and I wonder if, like, this is still appropriate. But at the time, Raked by professor also had attacked with professors that were hot. And I feel like today, I don't. They had that? They used to, yeah. Like, physically attractive.

Like, yeah, it had a chill. It had a chill. Oh, I thought that meant popular. No, no, no. There was a, it was like, how hot is your professor? And that people said that your professor was hot. Yeah, exactly. That's hilarious.

I bet that's probably gone. But, yeah, back in the day they had all of that. Wow. 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. They were very simple to do.

Then I would get my roommates involved and they would all create content and we 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 picks and shop. I was selling everything. Yeah. So I would sell the source code for $500, $1,000. 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 also it would happen to that. Cool. Did your brother get one percent equity? No, my brother had no equity in that. A lot 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, yeah. 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 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 graduate college at 20. 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. 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, both in-person of General Assembly and then online on UDMI, 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?

Is it comfortable living? Yeah, 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 thinking, different concepts.

Did 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. But yeah, we're all over the place. I had 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. We just order it of Amazon and people then just realized they could order it for Amazon directly. But you know, there's something over there. we built a domain name registrar to buy your name.com we had a lot of different ideas but nothing quite worked until starting teachable.

I want to tell you my two ideas and you give me your honest thoughts, you rank them, okay? I had 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 was so many empty driveways. And I thought, 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 on like a parking meter where you just like you have to guess, it's just charges you per minute.

And then, but anyway, there was 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, I'm going to fail on that too.

What do you think of that idea? I think it depends on like 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, a billion dollars plus. And a lot of these turn out to be really nice small businesses. Could cash flow a few million dollars a year, but because you go to 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. And 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. And so the liability of having someone parked there to earn like, you know, 10 cents 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 it was crazy, but we started this. a buddy who did all the coding on the back and we created the website and we created a fake Facebook account and we just added thousands of people on this Facebook account. And then we started promoting truth and tell. This is back in like 2010, 2011. Am I doing this for like people dating, friends, business associates, across the board?

We just thought it would be an interesting concept because there's no directory or like review of a person. It was like a black mirror episode kind of like this. Something like that. But like my thinking is like, okay, let's. Let's say for dating. You show up to somebody, they're creepy, they show up late, they're disrespectful. It would be helpful.

There was an app in San Francisco for girls to rate you. I remember that. Girls to rate you? They got so much. Yeah. 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 right 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 you piss me off, I could go there and kind of hurt your reputation irrevocably for just my own angst or whatever.

Yeah. That's why we never went with it. Yeah. The more we looked into it, the more realize that people only write reviews if they're upset. If it's ever positive, they're less likely to write those reviews. Like every one positive review, you probably have ten great experiences where they don't talk. Versus you have one bad experience, you have

one bad review. 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, you know, the unclaimed funds 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. There are companies that do that? There are companies that do that? Do they make, just there's rolling it? Yeah. I was thinking, like, find a way, but 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 make just to get all that data. I get it. Do they really? Yeah. Some guy reached out to me. He was an old, like an older guy. And it sounded like he was in the 70s or 80s and told me the same thing.

He's 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. That's kind of sketchy though, right? You don't know what he's going to do with that. 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 got to claim it myself. And he went out of a limb. He gave me the information where to find it, how to claim it, and I paid him. What was it? So basically the uncommissioned that was sent to an old address or something like that and was never claimed. The unclaimed funds 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 I got sent back to the post office or whatever. It all goes to this one. one main database where you can log in. What's the identifier of your 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.

It's 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? No, I think they do. Yeah. And so I thought that's what makes it more difficult because each state is separate. And then you've lived in multiple states, what states do you?

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 to check Texas because you're like, I live 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 money back. And usually unless it's like more than $100, it's not even worth it. There's plenty. There's like four or five dollars on there.

Like you're gonna pay more in postage. Right. I tried for one of my friends' dad. I was just looking up everybody in my contacts. It was like 12 grand and like, oh my God, $12,000. I texted my friend and I was like, dude, does your dad want $12? 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 and right near his address different person right near where he lived same name as his dad's crazy the other guy could probably claim it and they wouldn't know they would do all right here's 12 000 yeah there you go very well could yeah or actually the socials wouldn't match up oh true so no you

couldn't do that but anyways 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 got you going. Yep, absolutely. Yeah, ended up, I had a couple of courses. On Udeme 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 Udeme course, but then they cross sold my competitor's courses. All of that made me realize it's very, very hard to scale a business. So I ended up building, again, very simple app for myself and my buddy Conrad to put our own courses on our own website. It was a little 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 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? What was the moment you realized 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 core sales on the platform were about $5,000, $10,000. we kept 15% so 1500 a month 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 and we're like okay I think it's time to go to Silicon Valley and raise around and all of that how do you do you just decide to go to Silicon Valley and just so this is where the Facebook app stuff was helpful because I'd 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. 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, a guy named Matt Brazina, who did not realize he was our first investor, actually. He said, yeah, I'd love to invest, 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 for no big deal. But yeah, it was it was quite a process to get our first commitment. What did that deal look like in terms of like how much was invested? How much did you need? I'm wondering why you even decided to raise when it's, I feel like a pretty low overhead business. Engineers are expensive. 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 of what I built. So we had to go out and hire people. And, you know, at the time, engineers were, you know, maybe $100,000 zero being the starting salary. It's gone up a lot since then, but even that, you can't bootstrap that. So I ended up, I didn't know how much to raise. I picked numbers. I was like, oh, let's raise $1 million 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 $6 or 10? I can't tell you. They're all equally

arbitrary, but that's what we went from. Yeah, I feel like a lot of those startups, because we have our mutual friend, Sebi, and a lot of them are like, 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.

And raised from that. Yep, but it's all equally arbitrary, right? Like, I had an investor say, hey, this sounds like a $6 million dollar deal, not an $8 million deal. I'm like, your number is as arbitrary as mine. Like, neither of us can actually justify this. But for me, I kept saying,

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 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 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 Angelist. Then the rest of the round happened in the weekend.

I think it was like the 4th of July weekend. And like just over that weekend, we got everything. Oh, my gosh. What's the average amount that someone would invest in a startup? So for us, we had, I would say, if I would guess our average, we had a few 25K checks, a few 50K checks, and a few 100K checks. That was sort of the typical sort of range. Do you think that's typical of just industry standard that most people is going to throw a client? For individuals, yes. For funds, it's larger.

For individuals, I think that makes, yeah. It was Sebi that told me that I think it was one and only one in 25 on average is going to hit. Is that true? So, like, you have to, on average, invest 25 times without. one to make it 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. You know, another 10 companies return roughly your money back a little bit here or there. Maybe three return 2x. 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. Got it.

And you could have 100 companies that have, you know, returned by. little. So when you got that initial funding, did that last you for like a year or two? Like, how did you structure that? It lasted. 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. And we had nine in the bank when we sold. Oh my gosh. So once the business started working, we ran it pretty close to profitability, not fully profitable. Why raise money when you don't have to? Because I feel like 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 $4 million at $130 million pre-money valuation. So it means we sold 3% of our company for $4 million. 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 don't want to sell 20%. So I'm with you, right? If you don't have to sell, you can do these weird rounds

when you sell 3%, 4%, where you don't feel much, and 4 million made me feel a lot better about my company's, you know, cash position. So I think there's, 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,

we're raising a lot of money just from dope people. In fact, no one can invest more than 10,000, but we're raising $1 to $10,000 from, you know, a couple hundred dope people because it's nice to have smart, connected, network people invested in our success. 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 asking questions? It's much more of that and also like this army of supporters whenever to help us tell our story. Got it.

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 took quite a while to hit any kind of scale. It took us a long time to get to about a million dollars in annualized revenue. But from that point, actually it 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, and your 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, very big. As soon as you figured out that go-to-market motion, we were able to scale much, much faster. But even then, it wasn't easy. 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 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 a month in software. And we made a little bit on payments. On average, we'd make about $1,000 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. And on an average year, we'd have, you know, like tens of creators that make over a million dollars a year. So real, real money. And yeah, and they would still only pay us, you know, about $1,000 a year. So it was pretty good value for them since we'd in charge a percentage of sales.

How long did it take for you to run Teachable 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 how I ran the company. So you're just focused on just growing as fast as possible, basically. Well, yeah, not, yeah.

So I would say our average burn may have been like, you know, 30 to 50K. So that's like three people or whatever. So we're continually growing. So 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, 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 Hotmart and Brazil. And what I like the most about them is they're a founder-led founder-driven company, 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, but the timing just seemed right. And yeah, it was just a match sort of made in heaven.

But at no point did I go out to try and sell the company. We never looked for a deal. The deal found us. What were your biggest challenges in scaling? People. It's just like I love creating things, but I realized I didn't like operating things as much. Like, 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 found that very challenging. I found 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.

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, of running a company of, you know, a couple hundred people. And you're always dealing with problems versus the excitement of creating something. 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 want 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, you know, so from the time you want to do something cool until it happens, 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'm 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 that's... Honestly, I also don't know is this inevitable.

or not. Some degree of it is inevitable, but I'm not sure again, 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 stuff that I thought a lot about. 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 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. So I think there was definitely an ego play as well. What was your day-to-day schedule like back then? Meetings, just meetings and meetings and meetings. Yep. So I would guess, 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 closure 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? 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, learn from them. And then there's also just a case of like iterating. You try something. It works. You know, 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 sold it for? Yeah. I mean, again, 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.

And I think that's directionally accurate. Got it. And what was that like, was that a number that 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, was that just like. 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 80th to 90th percentile price. And based on what the business was at the time, which was doing, I think it was $20 million a year when we were negotiating the deal and $25 million a year when we sold it, it was a good price. I don't think it was an outrageous price. It was a pretty good price. And that's just what the business was worth. I don't think it wasn't a number I had to hit. Like if we had been a bigger business, I would have wanted more.

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, ended up. And the deal was half cash, half stock because I'm also optimistic about, you know, what Hotmark, the parent company is doing. And, you know, on part was treated very, very well there and continue to be involved there at the board and all of that.

So what did you do? after signing the contract, having it done? It took six months in between because structuring a deal, as you learn, there's so much nitty-gritty and stuff. And the day we ended up signing the deal, right? This is the day, like the deal was done. 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 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 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 with 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, our business doubled. or business doubled right after we sold the company. Do you ever look back and think, oh, man, had I just waited? No, because he still sold, right? Half of what you sold. Yeah, 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 asshole who's like, oh, man, I wish I could have had more. Like, in general, like, you know, there's two paths. I can either be so grateful. I'm like, like, life has been so, so, so, so good to me that, yes, could have sold it a different time for more money. Yeah. If you're going to talk about all the things that could have gone even better, like, just be grateful, right? You can't even enjoy your wealth in that point.

Yeah, yeah. Like so much, so much has gone so right for me to have what I have. Who cares about? You know, anything else is like, yeah. I love that mentality. I asked Tom Billy you this from Quest, but when you sold the company, let's just say, I'm just going to say a random number. Could be completely wrong, right? But if you got 50 million in cash and like another 50 million or whatever in stocks,

did that money just hit a bank account? It was just direct to asset out. Yeah, did it? did the whole thing hits and you pay taxes on that later. And can you say what the most that you had in that checking account before? Before? Yeah. Before?

Before? Yeah. You're sure your bank statement for that. I don't know. I'm reading his face and as it starts to grimace and I'm like, okay, but before. But before. I mean, I can tell you it. My salary at the time was 150 grand a year.

Like tens is like probably like 20K or something like that. 20K. Yeah. Yeah. But yeah. So, yeah, I've probably. 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 for my salary. You went from $20,000 in a checking account 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 a decimal. Any of that stuff. Yeah. God. How do that, how do that change your life afterwards? Changed. Okay, so, I mean, we're in a house, right? I was able to, like, move out of my 400 square foot apartment and buy a house. 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 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. Another way that it greatly improved my life is I was able to like just one, see my family a lot more to take the family on 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's 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. It's I don't think or stress about money. And that's something that, again, I try to 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 of it. about it. 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 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 of years past, after a while I realized, I missed the sort of meaning I got from building a company. And also, So 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 thing. I miss it. I want to compete. I want to, you know, I want to 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 because I want to build something really, really valuable. But I had one big swing in me. Can 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 has thus far only been for rich people, right? Whether it's like sending up trust or like how to best leverage retirement accounts and all of 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 we'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. Teach me. Yeah. Let me be the case study here. You sold me on this. Where would you start? Just pretend like I'm a student right now.

Okay. So the first thing I would talk about is. 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, we'll start very basic, but like if it's someone who's making, you know, $150,000 a year selling courses, what I would tell them,

is one, you probably, they're probably 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. Want to go through their business, is there anything that can depreciate? If there are any real estate tied to their business, there's depreciation 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 when you sell your company, which you can set up a trust and multiply that to $20 or $30 million. No matter what the scenario, this is a lot of crazy stuff, and yeah, our goal is to teach people how to do that. So is this stuff that a good accountant should know? Yes, good accountant should know. Not all of them do.

They don't, yeah. And then some things are 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. If you want, you can also do Roth contributions, which means 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.

year and still put in $67,000 into a Roth 401k using something called a mega backdoor conversion, which again, it's like niche tax strategy. So I did one of those last year, and it was one of the most complicated things. It took 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, I'm going to have like three weeks, nearly four weeks to get all this

situated and everything, start creating an account here, create an account here. I have to link these accounts. I have to wait for this thing to get settled and then I have to like withdraw the money here. It was incredible. 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. It's crazy.

It's crazy. It's terrible. It was so stressful and I hated it. Wait a minute. You made a Roth. No, no, sorry. Yeah. A rothar back door.

Yeah. And what was the limit on the? On the 401k, it's 67. No, no, no. What was the limit on the regular Roth IRA? If you make over $150,000 a year. Jack, are you trying to say that... That I make over $150,000 a year?

It's a big flex, guys. That was all that was. I'm just flexed. No, that was... I mean, yeah, I did because I contributed to it. But, yeah, that was... It was extremely... Yeah, but also a Roth 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 tax free, right? So again, like there's stories, I don't know if you read about Peter Thiel,

growing his Roth, IRAed of $4 billion in value. I did I heard about that. That was real estate though, right? No. It was his startups. It was startups. It was startups. It was two steps.

One, he bought his PayPal founder shares. And then that grew to about 20, 30 million. Then he made all his investments, including 500K in 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 for it, and teach people, you know, how to keep more of the money they make. Because when you run your business, please 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 come in. But how would that be different from a competent accountant? One, we're building technology, right? We're building like a complicated, like all of the accountants we're partnering with. They're using our technology to actually set up the solar 401K.

And as we build more products, they'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, education is $200 a year and you get all this information. It's a community, it's courses. I mean, it's an education business. So, so yeah. 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, would they need all of the accountants and attorneys? So what I would, what would, what would, what would, so I would, 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, I still think you, the human touch is very, very important when you're dealing with people's money. It might be a little bit of Ramsey Solutions where he has people that you go through that are pre-approved that know his system. And he's kind of the broker. between the deal. Yep. Yep.

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? Yep. It's operational now.

The company's been around for four months. We 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. Yeah, we're off to the races. The education product launches in two days. The one downside I will say with a lot of the 401Ks is that the investment options are terrible.

That's why a solar 401K is amazing because all the power for 401K, but you decide how to invest it. You guys have a referral or affiliate program? We'll give you a link. Oh, well, if you guys want to check it out. All right now it's linked down below. Write down the description.

Maybe a pinned comment. That's interesting. I can't remember who I went through or go through for 401K, but I had to set one up as an employee with, gosh, I think it was ADP or something like that. Yeah, 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 at my startup or my 20- or 30-person 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 to go into it. And like a lot of the competitors charge assets under management fees. And 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 interest, not our customer's 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 is going to be a big part. It also helps that, you know, with Teachable, a lot of people in this demographic are people that have worked with before, so 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 our 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 vested 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? Right now we have an office. I love working in person, right? Like, we had to work remotely towards the end at Teachable, and I hated it. I like the idea of spending my life on Zoom on a video chat, it's, 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 office, like, my ideas are pretty simple. I wake up, I work out, I go to the office, hang out there until like 6 or 7 p.m. Go do evening stuff typically. Evening stuff? Evening stuff? What's evening stuff? Evening stuff, I mean, look, we're in New York City, so 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. I mean one night or a week I stay. 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 until 2 a.m. and stuff. Yeah. That's a lot of freedom, man. Yeah. That sounds like the life right there.

I mean, I love the idea of going into an office. I recently got a Weework membership. You did? Yeah, I'm going to Wework. What? It's crazy for my productivity. Yeah. And especially since I've been traveling, at least recently.

I was in Austin like a week ago and now I'm here, New York. Then we're going to probably be traveling more this year. I figured a we work was probably... Do you go every day? In Vegas, yeah. I go every... I didn't even know there was a we 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 end of the road.

The location changes. Yeah. So the thing I'm trying to do, a lot of people love doing work, 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 and then two weeks remote, which will, at least for me. Like I also want the opportunity to work in different places. So I think that's cool. Yeah, that's great.

Work in New York every day, six weeks and the next two weeks are kind of remote. And then you go travel somewhere. Yeah, exactly. That's actually extremely ideal. You should consider trying out we were. I mean, you probably would hate it. But you should come with me sometimes. I would take you to a we work.

I'm not interested. Oh, come on, Graham. They have kombusha taps so you can get like unlimited. I don't like that. I think they stopped the beer on tap, right, after getting a lot of them. I didn't know they had beer on tap. We worked at the original we work, which was the one in Chelsea and it's crazy. Not only would they have beer on tap, 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 3 in the afternoon. They once had mimosas on a Monday morning, and I'm like, Does that sound kind of like gimmicky? That was not opposite of product today. But if you watch all that, we were like documentaries. Those were the crazy. Those are the crazy we work here. Those are the years of like summer camp and like.

And I was like. Was that when Adam Newman was running? Yeah, 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. There's so much to do. It's fun. You go to 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 like, you walk in, 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 taps, they have like unlimited seltzer, like sparkling

water, like not the alcoholic type. Cambocha, nitro, cold brew coffee, everything. Now, I heard WeWork was losing a lot of money. Yeah, but then that's why there's no beer on tap, right? So they cut the beer and they're profitable. There's still not profitable. 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, couple people are traveling, a 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, a few weeks, and I eventually fall out of it. But having a team working every day is really nice.

What do you think in 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. So I think, again, it's not for me. And it's a thing, though, I think 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 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 meant 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 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 engineers 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, 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, and you get paid to perform a service. But with the remote work, it really reinforces just how transactional that whole thing is.

But when you're in person, 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 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. 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? For me, I find burnout to be when I'm doing things and not getting the results, typically versus just quantity of work. 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 of flight somewhere, get out. Like just go to a brand new place and typically I find that recharges me. Any desire to have a family, settle down? Yeah, I mean, intellectually, yes. Yeah, I do. I mean, you know, it's something that, again, living in New York, I think it's very easy to get travel. you know, 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 good. Yeah, I'll be 33 in, what's, two months. Yeah. Two months, three months. It's crazy. Crazy. And I need to sell a company, man. Yeah. You guys are still so young. What am I doing, man? Yeah. Yeah. What's something that you wish you knew earlier that you felt would have helped you out and 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 realized 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 a company for seven years and now this and also investing in over 100 companies, it's enough to start seeing the patterns.

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 that 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 tech since, you know, I was 19 years old. I feel, feel like grizzled veteran. 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, which I think can be used by a lot of people, is I barbell it where I put half a fit roughly tracks the S&P. 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 will have. The other half I'm having a blast with.

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 50% in the market is enough for other people, it may be a different percentage. And the 50% I'm investing, I would see 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. But yeah, but mostly in tech startups where a lot of it is tied up in my own funds and then some and 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? Is it just a... Someone told me that it's really just an 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, they have a bit of a chip on their shoulder. Like, they really want to prove a point.

They move fast, like scary fast. Like, you know, it's very interesting when you meet someone, then you meet them the second time, and you try and think of how much they accomplish a mean term. The third is they're 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, I think, chip on their shoulder, charismatic, moves really fast. I think those are hallmarks of a good founder.

What about the business itself? Or is that secondary to the person? Could a good person make any business do well. A good person who wants it badly enough will be able to, 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. My blast, I mean, I mean investing at hire one. It's not that fun.

It's just like 50%. I didn't think like we're talking like clubs and stuff. No, I didn't think clubs. I was just thinking like travel. No, I mean my lifestyle. I can like literally live the life I want and travel and all. It's like none of it. I don't have 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 $2,500 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 would my wife want? Well, my kids want, you know what I mean? So it wouldn't really work for me at this time.

But I feel like, you know, maybe when you sell down, you have a, it's also so much easier without dependence. I know a dependent and I think I live the life I want. I travel over. I think like my entire life sounds like it's 10 grand a month, which I mean, there's a lot, but it's not 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. And we'll never exist. No, 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 Hormozzi-esque.

I'm a big, big philosopher. So you're saying, what are you saying exactly? So I'm saying like don't sabotage yourself to the point where it definitely hinders what you want, you know, wife and kids and a family. 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 that point in a lot. I agree with that.

I appreciate that. Yeah. It's hard to like to not. I've made a good point. No, I think that was a great point because I'm always acknowledging. I'm always acknowledging like what I think my future self would want. But the thing is I always tell other people this.

It's like it generally don't spend too much time planning what the rest of your life to look like. Because chances are it's like something's going to happen and there's just going to be like a wild turn. It's going to be. Set yourself up in a position to embrace serendipity at every one point. That's wow. That's a quote right there. That is a quote. Was that your quote?

Or did you? I mean, yeah. But again, I don't think it's a particularly unique or novel thought. But yeah, I think the idea that you want to set yourself up to embrace serendip. 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 to countries that are not super organized and stuff, you realize it's only so much you can ever control. And you truly get good at going with the flow. 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 to go and explore. I mean, 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 to New York for six months. And right, and I was just like, okay, I'm just going to 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 embraced these experiences. But it's 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 and stuff, and the people around there. And then I compare 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 feeling. strung out 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 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 in 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 half. I was going to start traveling. So that stuck with me. Yeah. I do my calls, I walk. How do you, like, how do you get those steps? You just go for walks? I do treadmill. No, very little treadmill. I, yeah, I do any meetings I have that are one-on-one or phone calls. I do walking meetings with people.

Love that. Yeah. I don't do Zoom. I like that. Jack and I used to go for a run. Yeah. And we come up with some of our best ideas going for a run. 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 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. The third thing, third thing was meaningful social relationships. Like, again, it's not about 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, but the work with purpose was missing. But yeah, I realized after all that time, only these four very, very simple things are the only things that meaningfully moved the dial on what it is that 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?

trying to find the right balance but again as I said a lot of companies will say you've got to come into the office two or three times a week but we're trying to see is if we can do six seven weeks of the office then a week or two weeks where people can work from anywhere so trying to find the right balance we're all to drink 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 could implement that right now yep that would be what would you think about that you'd be fine with a gram six weeks where we're just like It's impossible because we have, well, we have just, it's the last minute of guests that make it difficult. If I go east, though, I can make it back because the time difference. I would say as long, we never have guests that are booked out usually more than 24 hours in advance. Yeah, I can make that. Easy. Yeah. I would say, I don't care.

As long as you can make it, as long as you could make it back for a guest within probably 36 hours. Because we never have anywhere that's like, hey, I'm only here for the day. And if we do, we got, you know, Alex and I will take care of it for you. Cool. We'll cut you out of that one. Beautiful. This right here, I noticed you guys have a great bookshelf. Or you have a great bookshelf.

You do a lot of reading? Yeah, I've been 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. 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 that mechanic made me read much more, since it gave me this little, little, sense of completion. So I gamified it and, yeah, ended up reading a lot more. You know, I did the same thing but with gambling. Tell us about this. It's just a similarity between reading a book and gamble. I made a spreadsheet to track my wins and losses. And 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 yep and then once that's gone it's gone and uh no once it's gone you'll be like well let me make it back so we're still up right now so we're up about uh about 2,800 bucks oh wow for Alex it's investing yeah it's out there and so Alex wins like every time like sports betting or no it's literally just either blackjack

So mathematically you're going to lose there. A hundred percent. We went and played roulette. Alex and I, he put in $5, and at its high, it was at like $250. Like, you do realize in roulette, even if you do a one-to-one, that $5 to $20 to $40 to $40 to $8. And he was at $250 for $25. I don't recommend anybody do that. Like, this is literally just like, this is my yolo, right?

It's only gambling if you lose. Exactly. It's investing. It's only a problem that you lose to. I'm also, this is off topic, but I love building. stuff. How much did these shelves cost you to put in? Because they're awesome. They're really cool. It was I think it was about $10,000. 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 you said you read 50 books a year?

I aimed for 50 books a year. I was at 41 last year. This year we're off to a good start. We read nine already and it's pretty early in the year. But yeah, I read almost every night. It's part of the daily routine. For how long? It depends. It could be five minutes if I'm super sleepy. It could be two hours if I'm super into the book I'm reading.

You do it in bed? Yeah. 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 very much respect, they always say like, okay, like honestly, reading books is unlike any other way that you can. could educate yourself, I think that 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, 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 and do is I try and balance it all. 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 that makes you more well-rounded and interesting person. So 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. Last year I found this author Ishiguro. I'm probably mispronouncing his name. Another Japanese author read everything by him. So what I'll do is I'll like find an author and then like write like something and 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. But yeah, I try to be pretty diverse in the stuff I read. So I would say I read like half fiction, half nonfiction, all over the place. You watch YouTube videos or Netflix or something or is your entertainment?

Very little. I mean, I watch a little bit of TV. Not that much. Probably more sports than traditional TV, but yeah. Interesting. So basically you just swap out what other 33-year-olds would be doing on like TikTok and YouTube shorts where they don't retain any knowledge. I do a little bit. I mean, I have definitely like opened TikTok 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. I zone out. 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 audiobooks. Or if I could find it on YouTube, I'll just download it on YouTube and listen to it to X speed. Interesting. My brain can't keep up.

I just zone out. I think of other stuff. And then I'm like, what were they saying for the last two minutes? Yeah. I'm with you on that. Because the thing is, if you're audio booking, that means you're probably doing something else, hence why you're audio booking in the first place.

It's 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 don't focus on the actual task. And 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? It's tough to pick a single one. Let me grow rich right there. I really enjoyed. There's a book there by Ishiguro, never let me go. It's a little black mirror-esque, and that was really good.

But I pick one that I read recently. And so you've got to fill out these top of your shelves. Yeah. Yeah. There's a long way to go. I've been, I think I probably, I buy a lot of books. I probably buy, like, I would say on average 20 books a month. No way.

Books are so cheap relative to what value you can get out of it. A $10 book can give you an amazing five, six hours and, like, lessons you retain for so long. Five, oh, hey, five, six hours to read a book is, it's pretty fast. There's a big variance. I mean, we can, yeah, like, I mean, I would say books can take anywhere from three to 30, you know, like, yeah. But I would say five, six is probably median. Hmm. You fast read it.

I'm a faster reader, yeah. Yeah, definitely sound like that. Yeah. I remember books when I was in school, taking 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 at that. 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 there's writing a book to like, like the artifact, 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 going to be super hard. That's something I would just do for fun. You know, it's not for the business of it, but I think it would be really fun. That's interesting. For some reason, I imagine you writing a book on like startups. Like an Alex,

like a $10 million sales. I mean, there's a world. I would write a book on personal finance, but that would be for, it would 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 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. We don't want to. Our goal, the company that I'm super inspired and motivated by 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. And they changed an entire generation's relationship with their money. They became a trusted brand.

So our goal is to build something of Charles Schwab's size. impact. I thought Schwab was a lot older. Nope. 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? 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 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, is pure leisure, not that fun, if that fun for three days. But I feel like I could pick any activity.

It could be, I don't know, could be surfing. It could be a sport and get super, super obsessively deep about it. I definitely have that tendency. Like last summer I joined a tennis league and I didn't play tennis in a while and it wasn't even very good. but then I got pretty good over a summer. So I can pick anything and obsess over it. So I think that's quite possible. So anything you found that's not worth the experience?

Escargo. It was not worth it. 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 top.

Takarias right after and like enjoy the food at Takaria's much more. So yeah, 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. 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. feel like that gets you 80%. Mike Chipotle orders now over $20. That is not New York. New York double steak bowl, not even, no Glock, is now $20.40. No. How much do they charge for double steak now? $20 and $40.

And you don't get locked? Do you get a drink? Do you get chips? No, no. My friend got the same bowl with wok, $23 or $24. That's stupid. So, yeah, so New York, $10 gets you nothing. Okay, well, yeah, so adjust it for you.

What about Subway? I don't like the food there in general, but I do like that price. I think in that price range, if you just go to a random place on this corner, you know, like they're going to have good food. If you get to like a $40 to $50 burger, I honestly think it just starts tasting weird. Like the burgers start getting tall. No one wants a table burger at $40. You have to squish it down.

I hate doing that because then you ruin like all the art that went into like building it 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 of the back. anyway.

Exactly. And you have no bun. By the end of it somehow, the fun just disappears. It's weird. No, I'm usually left with like too much bun. Like mine at the very end

is like this much meat is like that much bun. I do, yeah, I mean, the one thing I do miss by the West Coast is in and out. So I am jealous

and you have that. I mean, and that's very good. Yeah. And you can, you can specify the ratio. Like I typically get a four by three, four meat,

three cheese. It's great. What is that? Probably still like seven dollars. I get a four by four. Why do you not like just make it even? I'm healthy, man. You're right.

Yeah, yeah, you got to... Yeah, no, I should consider that. 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, he went to, he just graduated business school from McGill. He's now living in Toronto and working in tech. And, yeah, that's the other thing. He and I have gotten to spend so much more time together over the last few years since he moved back the side of the world. But yeah, he's great. Is there ever, like, a rivalry between you guys now? I don't think so. I think, like, again, our relationship has grown so much.

And, like, I still talk to my entire family soft. And I talk to my parents almost every single day. I talk to my brother almost weekly. Like, 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. It was nice meeting you. Thank you for hosting us. Yeah, of a beautiful home. Oh, also, we got a free stock for you down below the description. I'm sure we'll leave everything that you need to know. We'll be down below the description, your links and everything. Thank you guys for tuning.

and until next time. See guys. I love that. Can you flip your mic and you too, Graham? Can you flip your mic? Oh, to face the other way. Yeah. Got it.

Good Grams. All right, here you go. See you at the clip goes this way? Okay, see it. You want to now flip. Andrew, put this at the end of the podcast. Don't don't put this in the podcast. These are first.

These are mics. I'm not supposed to know how to. No. You have road wire that goes there the same thing. There you go. Oh, look, Ted. You look great. Handsome.

Thank you.