BigDeal - #55 $250 Million Founder: What I Did Wrong & How To BUILD BIG | Ankur Nagpal

Episode Date: March 19, 2025

🚀 Main Street Over Wall Street is where the real deals get done. Join top investors, founders, and operators for three days of powerful connection, sharp strategy, and big opportunities — live in Austin, Nov 2–4. https://contrarianthinking.biz/msows-bigdeal Download Ankur's Guide to Fundraising here: https://contrarianthinking.biz/4l0QnyC In this episode, Ankur Nagpal shares his remarkable journey from humble beginnings to building and selling successful companies. Codie and Ankur discuss the importance of company culture, team dynamics, hiring the right talent, the evolving landscape and challenges with entrepreneurship. They delve into the fear of failure, personal growth, the value of leadership and the importance of taking action as a builder. Want help scaling your business to $1M in monthly revenue? ⁠Click here⁠ to connect with my consulting team. Chapters 00:00- From Humble Beginnings to Major Success 03:07- Navigating Company Culture and Team Dynamics 05:52- The Journey of Entrepreneurship and Financial Growth 08:55- Building Wealth and Giving Back 11:57- Innovative Fundraising Strategies 14:52- The Importance of Persistence in Business 17:56- Lessons from the Entrepreneurial Journey 24:44- The Value of Youth in Entrepreneurship 27:37- Navigating the Tax Code: A Business Opportunity 32:18- Building Trust in Financial Services 36:07- The Role of Immigration in Entrepreneurship 39:36- The Fear of Failure as a Second-Time Founder 45:52- The Importance of Creation Over Consumption 51:56- Navigating the 2020 Market Crash 54:44- The Value of Education and College 57:49- The Future of Online Education 01:00:34- Hiring Strategies and Identifying A Players 01:03:19- The Importance of Initiative in Founders 01:06:22- The Role of Regulation in Business 01:10:11- The Mental Challenges of Entrepreneurship 01:13:00- Finding Inspiration in Leadership 01:16:35- Taking Action as a Builder MORE FROM BIGDEAL: 🎥 ⁠⁠YouTube⁠⁠ 📸 ⁠⁠Instagram⁠⁠ 📽️ ⁠⁠TikTok⁠⁠ MORE FROM CODIE SANCHEZ: 🎥 ⁠⁠YouTube⁠⁠ 📸 ⁠⁠Instagram⁠⁠ 📽️ ⁠⁠TikTok⁠⁠ OTHER THINGS WE DO: 🫂 ⁠⁠Our community⁠⁠ 📰 ⁠⁠Free newsletter⁠⁠ 🏦 ⁠⁠Biz buying course⁠⁠ 🏠 ⁠⁠Resibrands⁠⁠ 💰 ⁠⁠CT Capital⁠⁠ 🏙️ ⁠⁠Main St Hold Co⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

We ended up signing the deal to sell the company on the single biggest drop in market history. I'm so excited for this guest today. He came from nothing and built not one company, but two companies, sold one for $250 million. And then is building another one that I think is going to be worth even more than that first. While I was in college, I started earning money with a bunch of side businesses making the million bucks before I was 21. Why? Were those like the Disney princess quizzes? Very similar. It goes very soft, I think, as a culture.

for a while. Our Slack would be like someone would post capitalism as a new colonialism. Like, you're not working in a coal mine. Like, what do you want? Like, better yogurt. I raised about $70 million on Twitter. That's amazing. You can always tell after you start working with someone if you're going to be good. You think Silicon Valley is kind of debt. This is the Big Deal podcast, and I'm Cody Sanchez. I am so excited for this guest today. He is a friend. I actually invested in his company. But the most interesting part for you is that he came from nothing, came from India all the way to the U.S. and built not one company, but two companies, sold one for $250 million, which is crazy, and then is building another one that I think is going to be worth

even more than the first. He shares what he would do if he was going to build from scratch today. He shared how he can tell the difference between A and B players. He shared what it takes to be young and hungry today and have the kind of success that he has. And he also shares a lot of takes on what happens once you make a ton of money. Also, there's some fun little stories in there about everybody from Mark Cuban to Naval Ravacant to the biggest names in Silicon Valley. And so if you are building something today, you are going to want to listen to this. And it is without further ado, I give you Ankur Nagpal, the CEO and founder of Kerry and former founder of Teachable. Well, now this office is too small. I was trying not to build

a big people company again, but I failed. Yeah. So how big is it? team right now. I don't know, 35, full-time-ish. At least for me, I would say up to about 50 was really fun. Yeah. When it got to 100, it started feeling less fun. Yeah. Yeah, I think the biggest one I've ever done is like 175, 180. And that, but you know what? They were really highly paid finance people. Yeah. It's honestly easier. Like, I just didn't have half the things that I have now in this business. In what sense? Like, it's, well, it's perfect incentive alignment. Yeah. So like, you know, You need a small legal team, a small compliance team.

But all of your salespeople are highly paid and incentive line. All of your portfolio managers are instead of a line highly paid. And so it's like very easy. I mean, we had a quant system that was like, if you hit these, you're fired. Yeah. So everybody knew. Yeah, you're not like having long one-on-ones and how everyone is feeling. God bless me.

I was telling Kate and Mark, our new president, that I want you to meet him. You'd like him. But he, I'm like, these creatives, they're like, I have so many feelings. Yeah. One cried in my office the other day. And I was like, I've never fucking seen this before. Have you ever had somebody cry at a meeting with you? So my last company, by the end, like Teachable, it became very hard to manage because, I mean, it was also around COVID.

Just the entire company, people forgot that we were there to make money and grow a business. And it was, yeah, things got a little, a little bit out there. Like I remember we would like people would get all these aggressive questions and like the snacks in the kitchen not being up to like. Stop it. Yeah. People were like how do you feel if we unionize? And it's like you're not working in a coal mine. Like what do you want?

Like better yogurt. Like yeah. There was a lot of that for. Where were you based? Brooklyn, right? So we were the stereotypical like Brooklyn office in 2020. So you can figure out. Oh, God bless.

This time around, even though we're a Brooklyn office. been very careful in who we hire. Yeah. So it's not been like that. No, it's smart. Yeah, well, I mean, hell, media is the same thing. But a lot of founders didn't realize that would happen, right? Like when we started the company, 2013, 2014, it was a different time.

Yeah, that was not the case. No, we've come full circle. I mean, even now in media, I think the sad part is that people don't realize when they want those things is the first kiss of death. Yeah. And so, you know, they think that it sounds good and then they don't realize that it leads to lack of profitability, which leads to people getting fired, which leads to, like, first working conditions.

Yeah, it's like crazy people. Like our Slack would be like someone would post-capitalism as a new colonialism. It's like, Jesus Christ. Like, you don't, you know, things that are like really like, yeah, like you're not being oppressed. It's fine. Oh, I did get somebody say to me the other day that, yeah, what's wrong with California is capitalism? And I was like, oh, wait a second, what? So this time around, I mean, we've made sure that everyone who wants to work really wants to

play for a team that wins, right? And that is important to them. Because for a lot of people, they don't care, they used to not care if the company did well or not. And this time we fixed that. How do you figure out if somebody wants to win or not?

I think in the interview process, you spend time finding out what motivates them and why they're there. And also, we are unapologetically, like, hey, we're here to build a very large and successful company. Last time, I think we overplayed the middle side because, like, again, mission is important, but we still wanted people who were primarily

there to win. But last time we're like, hey, you know, education is really important, but then we ended up getting a lot of ex-teachers and who struggled when things got hard. Yeah. Well, what's interesting is your last teacher was sold for $250 million. Did you think when you started your business that it would ever sell for $250 million? Oh, no one knows, right? Yeah. No one does. it's an insane amount of money. And at every step, though, it was just, like, focused on the next milestone.

I mean, I'd be lying if I said I didn't want to build a very large and successful business one day, but I didn't think if that was $50 million or $100 million or a billion dollars. But no. When you started, though, like, you didn't make a ton of money at first, right?

What's the least amount of money you've ever made in the year? Well, the first year, didn't really pay myself anything. So I didn't make any money while running teachable. And my first How'd you live? My first salary was $70,000. So I was fortunate in that when I moved to America, I didn't really have much. But while I was in college, I started earning money with a bunch of like side businesses. And that helped me make enough money that in my early 20s, I was living in my savings. Interesting. What were your side businesses in college? So I built Facebook apps. So this was back in

the day when, you know, you could send people gifts and stuff on Facebook. And it was crazy. It started my freshman summer. And at the end of my freshman summer is making like $20 a day. But all the way scaled to $50 grand a day and making a million bucks before us 21. What? Were those like the Disney princess quizzes? Very similar. So we had all kinds. We had like how good to answer this question, answer this quiz and you'll find out how good a lover are you. And people would like repeatedly take the quiz again and again until they got the results they wanted and then they would post it. That's amazing.

Yeah. So it was three years of that, but it was all kinds of, like, dumb things. But it really teaches you viral marketing and growth at a very early age. Like at our peak, we had more traffic than LinkedIn, Yelp, about the same as New York Times. We had like, I think like four or five million teenagers basically using it every single day. Get out. Did you, like, how did you come up with that? So started after my freshman summer when, you know, they launched the Facebook platform. And at first there were silly apps that would make $10 a day, $20 a day.

But it was a crazy time because you could literally reach millions of people in 24 hours. It was the first time that you could go viral or whatever. It was just years of experimentation and finding things that worked. Yeah. So you were a bunch of nerds. Where'd you go to school? Berkeley. Berkeley?

Yeah. So you're just eating granola. It was a bunch of nerds. Nurting out on coding. Yeah. And throwing up lover apps. I was very disappointed because I just moved to America to college. And it sounds really dumb.

but all I knew of the U.S. at the time was movies. So I was expecting American Pie, but instead I got like Berkeley, California. You're like, they don't shave our bits. Yeah, I was like, this is not the vibe. This is not what I thought it would be like. That's wild because you're from where originally? I'm originally from India, but I grew up in Oman in the Middle East.

Wild. Yeah, so my first day in the U.S. was Berkeley, and I remember I was, it was me and two other kids in our entire dorm that even drank alcohol. That seemed crazy because I was like, I was expecting the stereotypical frat party American college experience, but did not get that. How did you pick Berkeley? It was the best school I got into.

I got rejected from every Ivy League school. And it was, yeah, I wish I could say that it was some sort of like unbounding loyalty or whatever. But as an international student, you don't visit colleges or anything, right? Like you literally apply to a bunch of places and you go into any place that is like best ranked or whatever. Interesting. Did you come for money? No. My parents were middle class.

Probably by the time I went to college, they had spent most of their adult life saving to send me to college. So there was a lot of responsibility that came with that. My dad also always wanted to start a business, but it never felt financially responsible of him to. So I had a job. I mean, we were comfortable, but definitely middle class. Do you buy your parents stuff now?

Yeah. I mean, that's been the nicest thing that, of this whole process. What's the coolest thing you've ever buy your parents? Honestly, we just go on really nice vacations all the time. And I was actually thinking, in some ways it's nice that we didn't come from a lot of money because I have friends who are rich. And even though they've done well, when they take their parents on vacation, they just pay for the same experiences their parents always had.

But for me, like, now we can stay in nicer places than they have ever experienced. I get to see them experience all these things for the first time ever. So that product's really cool. What's your favorite one you've ever done? So the last, I was just saying in December, my parents have never been to South America. They wanted to like see as much of the continent as possible in three weeks. So it's incredible. We went to Patagonia on the Argentinian side and the Chilean side and the Atacama desert, northern Chile, drove to Bolivia, saw the salt flats, flew to Peru, Machu Picchu.

Pretty incredible three weeks. That's insane. Yeah. By the way, Atacanam is amazing, isn't it? It's like three worlds. The stars are, I've never seen anything like that.

Yeah, sick. I would totally go back there. Okay. So built this huge business. Didn't come from a ton. What's the most amount of money you've ever made in a year? What was your killerest year?

At teachable, I mean, it was just the exit year because when you're running a startup, I'll tell you my entire salary history, like six months of nothing, then $70,000 a year. Then I think it was 105, then 120, and then 150.

And once you hit $150,000, at that point, it's, you know, I was still single, no dependence living in New York City. You don't have, you're not, you're not balling out, but it was enough that I was focused on the business. Yeah. And then you sell the business and make, you know, basically infinite money. Infinite money. Yeah.

Do you ever say how much you sold the business for? You say $250 million, right? It's a, I'm supposed to say it's, I think this point we're to say it's a reported 250. Because at one point the acquired didn't want to, but yeah. Oh, no. And how much of the business did you own at that time? Half. Dang.

So that is, that's pretty infinite money. It's pretty much infinite money. I mean, half it was cash. Half it was stock. But again, the way I look at it is there is nothing I want that I can't have. And at this point, if I make more money, it's for the love of the game versus like what else I would. could do with the money.

What do you mean when you say it's for the love of the game? Like, why keep going after you've made $100 million? It's my sport. Like, it's like other, you know, if someone is a great tennis player or whatever, like, not going to retire at 31 or 32. They want to do this for another five years, 10 years. It's a thing that, like, you know, it gives me joy, a very competitive person, and it's my arena in place to compete.

Yeah, I've seen that firsthand. Yeah. I was watching you at the dinner when everybody was kind of, you know, and you're like, Tell me about what's really going on there. I don't believe it. So you now have built how many companies? Meaningful companies too, but in college, you know, we never built any enterprise value with this business, but, you know, straight up made cash. Yeah.

So it was just a cash line profitable business from day one, basically. The lifetime of a lot of these applications was 30 to 60 days. But again, our peak days were 50 grand a day, which at 20 years old was insane. Like even if you had 10 or 20 good days, that was amazing. Yeah, I think that's pretty rad at any age. You know what's also crazy is, like, I feel like because we're in Twitter or X or whatever you call it, you start to get this warped worldview where everybody all of a sudden is making seven figures every weekend. And anything that's less than that is like small or not interesting.

And I think one of the cool parts about the company you're building now is like, that's not the case. You're like very much for the small business owner, which is why I invested obviously. I think it's, we saw a lot of it first-hand running Teachable, where a lot of people were first-time entrepreneurs making money for the first time. So I was like, how can we almost continue that journey where we help them with the next part of their life, which is actually taking their earnings and building wealth. Yeah. You know what I want to talk about?

Didn't you send me back in the day? Didn't you fundraise for this company off of a Notion document? Yeah. That was a sick notion document. Have you ever shared that? I'm sure. I probably should share it publicly. Yeah. I'm going to find it. We'll put in the show notes. But you basically, everybody thinks it's really hard to get strangers money. You did it a really weird way. Talk to us about how you got other people to give you cash.

Yeah. So actually, if you go back right before that, when I fundraised for my fund, I raised about $70 million on Twitter DMs with, I want to say like maybe under five actual meetings. What was in the DM? Lots of feed picks. It was, yeah, lots of feedpicks. subscribe family fans. Like, yeah, fund this. You get free lifetime access. No, it was an ocean dog. Granted, the good thing is two big things were happening for me. One, I had a track record.

Fund one was doing well. Yeah. And two, it was the best time in human history to raise capital, right? Zero interest rates and stuff. But yeah, I raise money from 200 LPs, including, like Tiger Global was my biggest investor. I raised money from like 10 other venture firms and, you know, 50 partners from venture firms, all just by DMing people. That's wild.

And what was in the notion doc? Because I think this is like one of the things, everybody always asks me, how much money do you have to have to buy a business? How much money do you have to start a business? And my answer is zero. Yeah. Because it's actually never a lack of money.

It's a lack of knowledge. But that sounds like a rich person thing to say. Yeah. Until you realize how to get other people's capital. So like if somebody was asking you like, Anker, right now I need to get rich people's money in order to build this thing. What would you tell them?

I think you have to, for what worked for me was I had real fucking skin in the game. So what most people don't understand is they look at a venture fund. Venture funds charge two and 20, right? Which is 2% management fee, 20% carry, which is a take of profits. What people don't understand is it's actually closer to 20 and 20. It's one of the best kept secrets because venture funds charge those fees for 10 years. So if you raise $100 million, the investor makes $20 million, maybe even $25, regardless

of how the fund does. What I did with my fund is I took zero management fees, which was absurd for a fund of that size, and a quarter of all the capital is mine. So yes, the notion dock is important. Yes, like the mechanism is important. But end of the day, people saw I had real skin in the game, that it became much easier for them to say yes. Yeah. And I think if somebody wasn't you with your background, they would just decrease the fees.

They'd just say, hey, instead of everybody else wants this much money, I'm going to take half of that. Yeah. And or I'm going to actually take no management fee. And I'm only going to participate in the upside. If you make money, I make money. If you don't make money, I don't make money. What people don't realize is to be an investor,

it's actually not that hard to build a track record because you could invest $1,000 checks. Like a lot of people think, oh, I need to be, you know, a millionaire or make tens of millions of dollars to invest. But I tell a lot of people, if you want to put $20,000 or $30,000, you could get started. Just make sure you do 20 deals because it takes a while to learn how this game works.

And it is a game of numbers. Totally. I think your first 50K, you kind of got to assume you're going to lose 49,000 of it. But one of them could return 100 X and the math works out. Yeah. And it's also the interesting part. You know, a lot of times, so we're on our second fund. And I remember when I was first starting out, I used to think, well, I just want to get a little bit in a bunch of deals.

Then I think one of your deals, I think it was this company was too full. And you were like, yeah, you can come in for. like 10K and I was like, onker, in a fucking way. Give me more money, which really means let me invest more money in you. Otherwise, I don't want to do the deal. And I think that's another thing that people don't realize is that there's so much money that the wealthy have that they actually fight over who can give good

entrepreneurs more money. I never knew that when I was young. It's a stagger, like, if you make 10 million, if you have a net worth of $10 million, you are not in the top 1% of households. It's crazy. You're like one top one and a half. but you're on the top 1% with a $10 million network that is completely absurd. Yeah.

And I think the other thing, I'd be curious your take is like, also the more money you have, like the less pain you really want to tolerate. And so like money is like a risk tradeoff with pain. And so they want young people who are hungry and willing to tolerate pain for them. And if they're competent, they'll give you cash. 100%. And I think for a lot of people, especially when they get to a certain amount of, wealth. It also has, like, they care about the other things. It's like, is it a good narrative?

Is it a good story? Is it something I want to tell my friends about? And also, then the actual dollar amount becomes less important because they'd rather do fewer bigger things, easier to keep track of versus just like doing little pieces of everything. Yeah, that's a good, that's a good move. What would I have to do to pitch you? Like, if I was young and hungry and I wanted you to give me money. Yeah. So for me, a surprising amount of companies invested and have been cold DMs. I think, I don't know about you, but for me, email is dead as a channel. It's just impossible. I also assume it's spam immediately. It's impossible to keep track. If I've given up. So if I am going to get Onker to give me some of his 100 million, I'm going to DM you on Twitter.

I'm going. I've honestly been DMed on Instagram. LinkedIn's a little harder, but it doesn't even have to be Twitter. Just some place where I will someday see a message. Interesting. And even then, I rarely have invested the first time around. But I think people see progress. So if I see someone either repeatedly DMing or having improved substantially every single time, I think that's really valuable. Yeah, what do you think the percentage of people are

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But I think, I forgot the data, but like, I think the first seven emails you send or something, the chance of getting a response are the same, which means you should send seven emails because if you have a 5% chance, you love a 5% chance, even the seventh time you send a message, which is staggering. I didn't know that.

That is a life hack. Because that basically means, yeah, you can hit somebody up seven times. They probably don't even see the first go-round. And at some point, there's some switch that flips, I think, with people who were entrepreneurs that are like, oh, this kid's a little psychopaths too. But I'm at least going to respond to them

and be like, game recognizes game. The switch flips and there's just dumb luck and serendipity. Like, very often I will respond to something because I was on the screen already when I see. You know, like it's just being the right place or right time. So sometimes many shots on goal is helpful because you happen to catch someone at the right time or right place or whatever. Yeah. Now, the other interesting part I'm always shocked by is how few people keep going after the target that they really want. It's like they'll send you one message.

if you don't respond, they'll think it's embarrassing to send to. And so they'll just never hit you up again. No, I think, yeah, I think being persistent pays off so much. I mean, and I still remember, like, okay, now people will respond to me. But even when I was 18, 19 years old, every time email Mark Cuban, he replied. It's crazy. He is known for that. Yeah, yeah, it was wild.

I was like, oh, I could email him and he just replied to me. Dude, Mike Cuban also, guys off the rail slightly now with love, Mark. But on Instagram, I had, I posted so. something basically saying. It was about, remember when they were trying to restrict prices under the last administration? They're like, no, it's a good thing to have price capping. And I was like, I spent a lot of time in Latin America. Like, it's not a good thing. Here's my rationale. And I used a friend of mine's on Twitter to explain it in third person. And Mark commented on my Instagram post and was like, no, this is not right. And if you'd like me to

explain it to you so you can understand, I'm happy to DM me. I know. But then I went into it, the DMs and I was like, you know, saw your thing. I was like, does it ever work when you speak like that to someone? But he was like, I'm sorry, that was slightly contentious. I'm like, yeah, it was. Like, that's not going to get anybody

to change their mind. But then he's come back around. You know, just can't keep a guy down. He's done. I don't think anyone has timed an exit as well as he did. He sold a company that did very little for like $5 billion or whatever back in late 90s or a time with $5 billion was a lot more than it is today. Yeah, he did.

Yeah, that's actually, he did a pretty good exit from the Mavericks, too. Didn't he exit and sell it to Adelson or whoever? Adelson? And then, yeah, that's fascinating. Okay, with the other thing I wanted to talk to you about was, why did you choose, I can't remember your origin story. Like, what was the pain point that made you choose to build teachable? So I'd spent, yeah, moved to America,

spent all this time building Facebook app, scale that business. And honestly, then I hit two years of, what in retrospect is sort of an entrepreneurial rut where I probably tried 10 or 15 different businesses and nothing quite took off. And the journey you have as an entrepreneur is you don't feel to realize it's not taking off. You try a thing.

You always get a little bit of feedback. Nothing is that exciting. But then you have a new idea and you're pulled into it, right? This happened for about two years. During that period, I started teaching a little bit on Udeme. I taught in-person classes at General Assembly and built the first version of Teachable as a side project. But the difference with this side project is we just saw market pull from day one.

What does that feel like? Because I think somebody who's never felt it, they don't even know what it feels like to have something that works versus doesn't. So, and the funny thing is because I kept asking myself, is it's working, it's not working. But the biggest thing is the first month, we processed maybe like $3,000 in course sales. But every single month after that,

we process a little bit more. Until eight or nine months in, we were doing $40,000 a month in course sales. Across, I want to say 15, 20 creators. And I was like, wow, there may be a real business here. And then I went to Silicon Valley, raised venture around and decided, okay, this is a company. Could you ever have done that in India? I think now it would have, the world has changed quite a bit where India has now become a pretty good place for entrepreneurship and startups because it's a large market. size. The thing I appreciated the most about Silicon Valley is it takes young people seriously

in a way that most of the world doesn't. That's a great line. What do you mean by that? So when I was 19 years old, 20 years old, I was in college, I had the chance to meet, you know, Mark Andresen, Naval Ravikant, like all these like people that were iconic and I looked up to. And they all took me very seriously, almost as a peer. Like, what are you going to build? like this sounds so great. Contrast that with when I went to India and I tried to meet with the CEO of a couple of smaller companies would condescendingly ask where my parents were. Right? It's such a different attitude. And I think San Francisco and Silicon Valley knows that young people have historically done incredible things. So young people are taken very seriously. Yeah. It's a good point because you're kind of seeing it whether people like this administration or not, but how the old infrastructure of government is looking at young people coming in with, with disdain. They're like this 20-year-old, this 21-year-old.

And I think there's no longer this barrier between ability to execute and age. In fact, I mean, the speed at which I see young people able to force function moves with technology means that we're getting slightly more obsolete the older we get. Also, what you realize is young people typically tend to have so much more time, right?

Like they're very time-rich. And as a result, can go so much deeper. and a lot of things. Like, again, imagine if we get to a world where the cost of building something just comes down to how much time you have to play with the thing to build it, it's advantage young people. I mean, you just have so much more time. And that's what I mean when people say Silicon Valley is an idea versus a place, but the idea of Silicon Valley was always, you know, 18, 19, 20-year-olds are going to do amazing things. So listen to them, let them do their thing. Yeah. And they have the best risk-reward trade-off ever, which is, you know,

a future appearance of time because they're young, and simultaneously no real risks because they don't have anything yet. Absolutely. And if there's anyone, I always tell people if you're 18, 19, or 20, you're in a golden window where a lot more people will be willing to meet with you because of your promise and your potential. Like, I'm not kidding. Like, I think it was easier for me to meet with a lot of iconic Silicon Valley people

because I was 18 or 19. So I could be introduced to someone with a bright future. I mean, you're still young, but you're not like, oh, this crazy young person with the bright future. Were you like a little genius? I think it was because of the Facebook applications that I'd built a business that was doing well. Growing up in high school and stuff, I was always smart, but I was pretty rebellious. So my grades were never very good. I wanted to play cricket internationally, so sport was more important to me.

I was always smart, but I was, yeah, I was barely top. 20% of my class, which wasn't that good. Interesting. And then today, you're building a brand new company. Why did you choose this one? So it was while selling my last business. And again, as an immigrant, I know nothing about the tax code, nothing about how money works, personal finance. I wasn't investing. I was doing nothing. But I realized how it's smart lawyers and accountants, how much opportunity there is in our tax code. And there's no easy way of accessing it. So that a little bit of a light bulb moment that I was like, if there was an easy way to make, to productize all these tax savings, the tax code, that would be kind of a fun business to build.

It's valuable to people. I also like love, I've always loved there's a system. How can you be smart about it? How can you hack the system, break the system, whatever? And this felt like a challenge that way, like, you know, like here's a system with a bunch of rules, but there's loopholes. How do you actually help people take advantage to these loopholes? So it was a fun, fun kind of business to work on. How big is the business now? So we're a little bit over $2 million in annualized revenue. We custody a little bit over $100 million in customer assets,

which is good. We're a couple years in. And part of me as a founder is like, I wish we were 10 times bigger. But the nature of the space we're in is people trust us with their retirement dollars. And as a result, we are regulated as we should be. And there's a lot of responsibility when it comes to running

these kinds of businesses that you have to sort of set up the right infrastructure. We're trying to long-term compete with Vanguard Schwab Fidelity and these companies that are, you know, anywhere from 40 to 100 years old. And we're fine if it takes a little bit longer. Did you have to pay a lot of money for that website name, your domain name? Carey.com, yes. I signed very strict paperwork allowing me to never talk about how much, but it was quite significant.

Why do they always want you guys to never say how much people pay for one-word domains. Is it just like one conglomerate that owns all these and then they say don't tell anybody? I think the biggest reason is there's no objective way of valuing a domain. Right? Because it's such an illiquid

market that there's not that many buyers and not that many sellers. But the sellers are pretty smart. They're happy to wait almost an infinite amount of time. Like, for instance, someone revealed they paid $2 million for friend.com. Which is insane. We didn't pay anywhere in that much.

I was going to guess seven figures, but we won't tell our friends on the Internet. Okay, I don't want to get you sued in the portfolio company we invested in. Exactly. That's why, yeah, well, I think, and you just get killed on the Internet. Remember when Nick and Sean Puri put somewhere? And I think they only paid like 400K for it, not only. That is a lot of money. Yeah, 400K is a lot of money for Somewhere.com.

And then they just got massacred. I will say that we have made a very strong R-WI-L. because we deal with people's dollars. So trust is really important. And a domain is a way of short-cutting that trust. Yeah. Do you think yours is better than contrarianthinking.co? I think we're about the same, roughly, roughly equivalent.

I can probably sell mine for $2 million too. I'm actually so bad at branding. It's almost laughable. Like, can you spell how many vowels? Here's why that could be a good thing for a lot of people in that. I think too many people worry about it too soon. Like, again, when we started Teachable, the company was called Fedora, which is an awful name, domain name, use Fedora.com.

But guess what? We spend no time on it. We got to market faster. We got real customers faster. You can fix brand later on. People don't realize that. You can fix brand a year and two years in. At any given point, like even now, we're a little bit over two years in. But 10 years from now, almost all of our customers, 10 years from now, are in our future. right? So that was the sort of attitude that you hold on a lot to what you already have, but the majority of your customers in 10 years, you've not met yet. They're in your future. What you have now is a tiny, tiny percentage of them. That's a great point because, I mean, part of the reason so many people I think never become entrepreneurs or get real revenue in their business is they have this whole story about what it takes. It's like, I need a website and then an LLC

and then insurance. I mean, I see it on my YouTube comments all the time. It's like, you miss 12 steps. It's like nobody does all 12 steps in a row. You just start. And you go. Even like again, our business helps people to save money on taxes. The number of times after tell people you don't have a tax problem, you need to make more money. Like your problem right now is not taxes. You're making $30,000 a year. Great. It's a great start. Just doing it is important. Don't try and save taxes on 30 grand. Think about how you can 10x your business. And then we'll talk about saving money on taxes. Yeah, well, because the thing with Kerry that I think is unique is it's really focused on businesses and small businesses. And so basically, if you ever run a

small business, taxes are the biggest pain in the ass. And you're always getting these, you know, different notices from all over the place. And then your taxes will materially differ depending on who you get advice from. And so it's often not a how. It's a who. And the who can totally fuck you. And so the cool part about about the software, I'm like sipping my own Kool-Aid here, but is that you have standardization. Yeah. And the U.S. tax code, when you look at it, I think you can tell a lot about what a country stands for, what it incentivizes, looking at its tax code and the U.S. tax code is written in favor of business owners, which I think is great.

The country wants to incentivize the creation of business. So the challenge we have is how do we productize that so people can take advantage of all of that. It's like, yeah, taxes are not why people become business owners, but it's just one other perk, which is why when you look at, you know, the wealthiest people in the country, not only are they typically business owners, are also paying taxes at a much lower rate than regular salaried employees. Yeah.

If you weren't going to run this business, what's the other business that you're like, God, that's a cool opportunity right now. I want to buy a cricket team. I mean, that's honestly, that's not a,

it's not a phenomenal person thing you've ever said. That is not a, it's partially rich person. It's partially for my failed athletic dreams, right? It's like if you can't, if you can't do the thing yourself, like at least buy the business that does the thing.

I like that. I think that's actually, isn't that what, I mean, one of my favorite guys is Wayne Hizinger, the guy who started waste management. And that was it. He's like drove trash trucks, owned trash trucks, played in trash

until he owned three baseball teams and also dated models. There's a non-insignificant number of people, I think, who have been very successful in business, who would give it all up for like their failed sports dreams. Are you one of them? Probably like it's, as I'm getting older, that tradeoff is getting harder because now it'd be at my, my, close to my professional sports retirement age.

Maybe, maybe not. But yeah, there were times like, a few years ago. I was like, would I give it all up to be like really good at cricket, played in a large stadium, you're the fans chant your name? Yeah, probably. But then you'd come to the U.S. and nobody would know who you are. Yeah, exactly. Yeah. So that is a little bit of a doubt.

Yeah, you got to pick like football or something, like international football. There's zero brown people in, in any major American sport, which is insane. Is that true? There's, I think there's a half Indian dude in the NHL. That's about as close. Well, I think we have no one in the NBA. the NFL and MLB.

That's wild because you should. But spelling me. We're killing it. Spelling me. Dude, you are dominant. And procreation. Yeah. You guys figured out procreation.

You like it. And being CEOs. Yeah. It's actually really cool watching the growth. I mean, because it's interesting. Different demographics do have these natural tendencies towards entrepreneurship.

And India's huge at it. I mean, in a force multiplier way. Like we have a lot of Latin American entrepreneurs, but we do have, we have nowhere near the percentage who get the scale. Why is that? I also think it's exacerbated in immigration patterns because the enterprising Indian people are the ones who came here. So it is much stronger in the U.S. Like a lot of immigration in the U.S. were people who came and bought small businesses.

Yeah. Is it just really hard to get here from Indians? So the people who get here, you're like, that's the cream of the crowd. Like, for instance, there's a lot of Gujarati people here. And I was reading it's staggering. I think, like, half of all small motels are owned by them. They're all, like, yeah, one extended family or something. Yeah.

Yeah. I remember Twitter not liking it. But I was thinking, that's pretty cool. Yeah. It's really, and I think that's also one of the things, you know, that I think America stands for, or at least used to stand for, maybe still does or whatever, is it becomes this magnet, where if you are a person that wants to go do a thing and build a thing, you move here. which is why for my dad, it was very clear that, you know, I would do better in a country like America.

And I think it's important we maintain that. I totally agree. It's like half the point of everything we do. I mean, I continue to be blown away that only 6% of Americans own businesses. That number to me just like doesn't make sense in my head. I bet that doesn't account for the one-person business. It accounts for the one-person business, but it doesn't account for non-revenue producing businesses. Because LLC creation, you know more than I do.

There's a shit ton of those. But those are just incorporated businesses that never actually are realized. I mean, we could double. Somebody will tell me on the internet if I'm a liar. Because the numbers I looked at was more if you include all kinds of self-employment income. The highest I've seen is 11%. What was the highest you saw? I saw something higher, but the denominator, but it also depends.

It's the denominator of people that are eligible to start a business. Are we excluding, you know, nine-year-olds and stuff like that as well? Yeah. And what is the key? category of business. Yeah. I guess as long as you, anyway, we don't have to get too wonky, but if you like measure it the same way across all countries and then see which ones have the highest.

But I wanted to talk a little bit about some cool things you do at your company, Carrie. For instance, I saw this tweet that I thought was brilliant about how you do vacation policy to keep high-level people, but make them stay in office the rest of the year. Yeah. So we're in the office every day of the year. Not strict about it. like if someone comes in four times a week or whatever, it's fine. But the default expectation is we're in the office every single day. But we're remote for one month.

And partially it's because for anyone in New York, winter in New York can be soul crushing. So we're remote in February in the office 11 months of the year, which I think works pretty well. I don't know why. I would be scared that my business might fall apart. It doesn't. The business doesn't fall apart. It is still, you still have to learn how to do it. And I'll be candid, we're still learning how to get good when we're remote.

It is something I kind of battle against a little internally because I love being in office. I think we're super productive. But the downside is we're not taking advantage of a global workforce. So we're paying New York salaries for pretty much all roles. And over a long period of time, am I missing out by not hiring an amazing person for some specific skill because they live elsewhere, potentially? So we'll see how that evolves. Have you found that by letting people go for a month remote, you retain people more, you get better caliber of talent? The thing that's been interesting is when most people come back, their reaction is not like, that's sick, why can we do it always?

They're like, yeah, it was great, but they're like, oh, I missed the office. I kind of missed being around everyone. And it almost builds renewed enthusiasm for being back at the workplace. Interesting. I think we're thinking about trialing something like that in August here, or maybe, July because it's miserable. Again, there's no one. And also the benefit you have is like people got annoyed on the internet as they always do. But no one in our current company has kids. But I think we have kids you have to do it over the summer, right? Because no one can go in February. Oh, right.

Yeah. Why don't you just hang out with the kids more? Yeah. Or is that not? Is that something a person without kids would say? Yeah. Okay. Okay. Yeah. We won't put that on Twitter so I get murdered. Good for engagement. Well, that is true. So, you know, we know that, we know that, 90% of startups fail, but you chose to keep doing startups anyway. Were you ever scared that you weren't going to make it or that it was going to fail? I am more scared this time, and I'll tell you why, because the first time, it doesn't matter. You're expected to fail. The first time, like most companies fail, you'll probably fail.

It's fine. This time I have a stronger fear of failure because I've built up this self-image of myself as someone that is good at companies. I've told other people what to do. I've sat on panels telling people what to do. be fucking embarrassing to publicly fail. So this time there's more of a fear. What I've realized as a second time founder is a lot of things are easier.

Fundraising is easier, hiring is easier. But truly building a product that people like is always going to be hard. Okay. When I sell my business, I want the best tax and investment advice. I want to help my kids. And I want to give back to the community. Ooh, then it's the vacation of a lifetime. I wonder if my head of office has a forever.

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and discover actionable solutions to reverse it. It's so hard. But you're right, it is scarier, especially when you're public. You know, I think about that now with these companies. And we have a lot of companies. So, like, ultimately, one of them that is public will fail. Yeah. And I have a bunch of self-worth wrapped up in that.

I'm like, no, no, no, I'm always mouthing off on the internet about stuff. I better know what the fuck I'm talking about. Yeah, how embarrassing. They all like the startup guru, like, yeah, telling everyone what to do. But the funny thing is what you'll find at least is even if that were to happen, there may be some pockets that may kind of laugh at you or whatever. But the people who know, the people who build businesses, ultimately know how difficult this whole thing is that you're not going to get that from them.

Yeah. Do you try to surround yourself with a certain type of person in order to achieve these big things and not get crushed? Probably more so when I was younger, when I was living in California, you know, I did that. Now, honestly, I like a diversity of people in that. I like people that are very competitive, but they don't have to all be competitive at building the largest startup. But I'll get bored of around people that don't want to be the best at something. But I can be around people that want to be the best at like running a sub three-hour marathon

or like the best at whatever special scale. I think that kind of diversity is probably more fun. than just people that want to build startups or businesses or whatever. Yeah. And I do think at some point levels of the game, you know, you kind of money becomes slightly less interesting to talk about. And it's more the game and winning.

Yeah. I've sort of had to pressure myself and to keep talking about money because when I was younger, I wish that other people would have told me the truth. They're like, how much did you make? How much did you actually spend? Like, what happens at this point? And I think once you start,

you just don't talk about that anymore. And the people who do kind of talk about it in a scammy way and it's not real. Yeah. So I think it's cool that you still share so many of the, here's how much money we made. Here's what happened here. Like, that's really rare. Yeah.

I think the other thing I've talked to friends in similar spaces is a lot of people ended up having very different attitudes towards it. And the thing I've tried to consciously be careful of is not to become the person where they're so addicted to the chase of more money for the money itself, where it becomes a little like, you'll never be enough. I know I know people who have mid-hundreds of millions of dollars

where sad they're not a billionaire. And I don't know, I find that kind of sad. Like I think if you want to be a billionaire because you want to win the game, that's awesome. But if you feel like you don't have enough and you're coming from this place of scarcity,

that's something I'm consciously trying to avoid. Yeah. Do you still feel like you're poor and you don't have money? I feel like I have an infinite amount of money. I like, it's not, as I said, it's not, it's, it's not that I'm lacking for anything. I think if anything, what will change by my further success is a number that I go to the grave with in like all practical yet somewhat dark terms.

That's so fascinating. So you don't have any of that poor kid mentality anymore. No, I think I have. Did you ever? I think I have infinite. When I was just, when I first came to America, I remember just like, because my parents had saved their entire life for me to be there. I was like, I didn't spend money.

Like, spending money felt frivolous and stupid. And I think that sort of sense of scarcity made me appreciate not having to think about money. So to me, it's amazing to not have to think about it. Like, let's imagine we're on a family vacation. Flights get canceled. We need to go re-book some expensive flights. Just not having to think about any of that.

I've been like, oh, here's a credit card. I don't have to worry about it. That, to me, is the real value of it. Um, yeah, when I fly, I fly whatever business class, first class. My seat is flat, but I don't need a private jet. Yeah, I agree. Stuff like that. Sometimes I like one though. Yeah. I'm not going to why. We were on a tiny one the other day to Marfa because we bought some land out there, which is a ridiculous thing, but it was for the, anyway. So, and the one nice thing about them is just the time savings. But the thing that people don't realize, like a nice business class seat, way nicer and a seat, except on the big. jet out there. So I think a lot of this is just flexing on the internet. The pain of maintaining stuff, and yes, eventually you can outsource that and you scale it all

out is a lot of times someone was telling some old like blainer dude or whatever that like there's no yacht better than your friend's yacht. Like if you know, like if you get to like do the fun thing once in a while when you have to deal with it but not deal with all the work that it entails, that's the best. I agree with that. I still totally have the poor kid mentality. I don't know if I'll ever get rid of it where I'm pretty sure at any moment, like, we could totally be broke again. And I don't know if that's an edge sometimes or not. But I think it's really cool that you seem to have been like, no, I'm going to be really grateful for what I have. And I think that's a total fact. It's a battle I have to have with my mom quite often

because she's always like, oh, you know, like you're paying for this like slightly expensive vacation. What if you run out of money? I'm like, mom, I can try me an Excel model, right? We can play with this. Like, that's not how math works. Like, we can, like, I could spend 10 times more and, like, this is not, we'll be fine. I love the line. Mom, I'm going to show you an Excel bottle. She's like, that doesn't help.

Yeah, doesn't help. She's like, this feels like a lot of money. That's really sweet, though. What about, what would you tell, you know, a young kid listening to all this today who is just like, man, I don't know if I'm smart enough. I don't know if I can code. I don't know if I'll ever get there. What should I start?

What would you tell a 20-something that wanted to be you? I think when I started, and I think it's true for a lot of people, there's a certain element of like doing these things for the love of the game in a way that, yes, part of my motivation was to be very successful

and make a lot of money. But I also really liked building shit, playing with things, growing products, and to kind of not forget to that part. I think anyone listening this right now, you're in such a fun time to build and play with stuff. Like, back when I was in high school, we used like Microsoft front page to build whether it was like the tooling was awful, right? Like now there's incredible tools where you can

imagine anything, build stuff. I think it's a great time to like, yeah, just go deep on that, have fun with it. And I think it's a yeah, phenomenal time for that. Yeah, I mean, I think also if you do interesting things, then interesting people find you interesting. And so just build something, whatever it is. Especially because these days, I mean, we find this on the internet. People think it's cool that you start a vending machine route and you talk about it. You don't have to be a rocket scientist.

But just try to build. And I think we're losing some of that. I think like create the act of creation. I guess I talked about the good part now. I think the dangers of now is it's become so much easier to consume. Like there's so much more stuff to consume that it's very easy to fall into this consumption trap where you're spending four hours a day watching

TikTok videos or whatever that fighting that I would imagine to be the hardest challenge I don't know what it's like to grow up when you've been you know I was talking to someone had Instagram since she was 11 years old I don't know what that does to your brain or what that's like to deal with so I guess being able to counter that

is probably the challenge but yeah if you can create instead of consume that'll take you a long way. You're single, right? Yeah. Not married. No girlfriend at the moment. Why not?

I was in a pretty long-term relationship when I was young, like, 8 to 27. I think dating in New York can be quite fun, but the downside of that is, the challenge a lot of people have is a little bit of the shiny object syndrome. Yeah. where you're dating someone, when you're dating someone and there's someone else. Not Excel models. Yeah, correct. Correct. Yeah.

But with that said, I mean, I'm 35 now. Yeah. And my parents, my parents weren't that excited when I started the second business. They're like, you should get a wife like that. We would be more excited at this point with a wife than another company. Were they nervous when you started your first one? and how did you deal with the fact that maybe you wanted to take a different path than what your parents wanted you to do?

It polarized my mom and dad a little bit because initially they were supportive, but then I said at two years of nothing quite working out. And my dad was very much like, dude, just keep trying stuff. Like, you know, like, I wanted to do a business. I never could. You have every opportunity in the world. You're super young.

My mom was like, I don't you get a job at Facebook? They may hire you. Like, you should go work for someone. So it bifurcated a little between the two. But as soon as the company started doing well, I think my mom was happy. We got on board. Yeah, I mean. Yeah.

But even like when I was close to dropping out of college at one point, my mom was very against that. I think my dad's a little bit more risk-taking. Would you tell a younger version of you to do the same path? I'm very happy with the path I took. I think I was very fortunate that I was in the right. place at the right time. Like when I look at all the people I met when I was in California between the age of like 18 and 23, they've all gone on to do such incredible things. There's something special and unique about that. I don't know if such a place exists today,

by the way. Like if it does, it may be online somewhere. I don't think it exists in like. So you think Silicon Valley is kind of dead. I think it's not. It's the time. Like so this again was 2007, 8 until 2013. There was no competition. right? Like New York didn't have as many companies. Like, L.A. didn't have as many companies. So I think the rise of the rest of the world has been generally a good thing. But if you wanted to be in a startup, you had to go to Silicon Valley then. Yeah, it's so true.

Yeah, I remember back in the day, like remember AOL, the... Yeah. And Steve Case had his rise of the rest tour. Remember that? And he would go around the country, basically, on this bus talking to second and third-tier cities, which probably were New York back then. But anywhere else besides Silicon Valley, trying to get people to do entrepreneurship.

And now it's existing all over the place. I mean, you're here in Austin. And we had a portfolio company. Did you go to the dinner on Saturday? No. Okay. We had a portfolio company dinner with a bunch of our portcoes. And I think there were like eight of them in town.

Wow. Which is crazy. I mean, two of them are billion dollar businesses and they're here. You would have never had that on our come up. When we moved, when I started Teachable in New York in 2013, 2014, it was a weird thing to do. Like, even at the time, it was. we were questioned a lot. Like, why are you building this company in New York?

And there actually was a general sense that you couldn't find experience startup people in New York. Because anyone with experience would be in San Francisco. Ironically, we had a good time recruiting then because there's never a shortage of people in their 20s want to live in New York. So there was a big exodus of people. But yeah, now it's everywhere. You also sold your company during the stock market crash of 2020. Right? What was that like? So we ended up signing the deal to sell the company

on the single biggest drop in market history. It was a Thursday when COVID was starting to be real. Then on Tuesday, we announced the deal, which then became the new biggest stock market crash in history. So it was a very confusing time because on the one hand, we're like, man, like probably a great time to sell your business. asset values are falling.

But on the other hand, we saw our biggest sign up and revenue days are teachable because this was the opposite sort of trend where our business, like we sold the company at about $25 million in ARR and we doubled to $50 million

three months later. Wow. Which was our growth projection for the next like 12 plus months. Then you could have had extra infinite money. Correct. But again, like as part of me was like, oh, I should have waited. And I was like, life has been,

my internal, dialogue is life has been so good to you, you've been so fortunate. Don't be the whiny, rich asshole. It was like, oh, if only I could have had more, like, you know, like net, net, I'm so grateful for everything I've gotten. So every time that voice comes, I'm like, shut up. Like, you're, you know, life's worked out pretty well. Well, plus, I think it's cool to build something that's never existed before.

So, like, Teachable was one of the really big learning platforms back in the day. Now there's a lot of them. That's awesome. There's open market. But this new thing at Kerry doesn't really exist. So thankfully, like, you had enough to keep going on. Teachable. I was passionate about one side of the business, but I was not passionate about the other side of the business. I was always a very bad student. I didn't go to class. Like, even when it came to,

like, online courses, I didn't take a ton of them. I liked the business of being a creator and that side of it, but I'm more passionate about the business I'm building this time around than the first time. Tax code just gets you going. Yeah, I think, I think it's a challenge in a way that, like, again, in the teachable business, I found it fascinating how creators make money and run their business. But I was always a terrible student. Like I never went to class. Like the idea of like, like, I was not passionate about education quite the same way.

Would you tell a young kid today to go to college? I think go to college as a great way to grow as an individual. It's a person, potentially because it's fun. I wouldn't go there for the sole purpose of like maximizing my future income. I think what college is, it becomes a luxury good where if you can afford it, You have time, you have parents of money, whatever. Go do it. Have fun.

Have an incredible time. What about an MBA? Like, I almost never hire MBAs. And once in a while, if they do, it's despite their MBA. I always say that we have to wash the MBA off you, even though I have one. At the same time, again, look, if you're 27 years old, 28 years old, you've worked pretty hard as a banker, kind of want to chill for two years. You get into Stanford, Harvard, whatever.

It's a pretty good life. You'll meet cool people. You'll hang out. Think of it as a mid-career of vacation. Sure. But if you fully go there to internalize how to be better at business, then that's a big red flag. Yeah, huge waste of time. But I think it's useful for people to say stuff like that because Lord knows, that's not how they're selling the stuff these days. And, you know, I was listening to... And now it costs what, like $100,000 something dollars a year? Yeah. I mean, back in my day, I was in

finance and so they paid for it. So that was sweet. I'm like, I get to make whatever I made at the time. Plus, you guys paid for my college? Awesome. Oh, you also keep your salary? I did a fucking great deal back in the day. This is one of my proudest deals, actually. I was working at State Street at the time. And they paid me. I was making, you know, great money for me back then. A couple hundred K a year, great.

And then they paid for me to go to Georgetown for my MBA. And they had no clawback provision. So typically how it works is if they pay for your MBA, you got to stay for like two or three years. Sounds like a terrible deal from their perspective. Nailed it. I mean, they're so big. They're like, shut up. tiny little analyst or whatever I was.

But what's interesting is I'm actually going to see Dave Ramsey on Monday. And I was watching his old videos. And there was this video on Kurt where somebody said, like, we're a million dollars in debt. And he's like, you know, oh, Lord, what'd you do for that? And then they said, we are $450,000 in student loan debt for two people that make $70,000 each a year. MBAs or? Advanced degrees. in like policy or something they work for the government.

And I just think that that is almost, of course, that is their decision. That wasn't a very good decision. But also, we've been so programmed that to me that is a huge disservice to two people that they will never be able to get out from underneath that. And they can't even get out of it with bankruptcy. Yeah, I think there's so much programming of like, oh, you don't know what to do, go to school. It's never a bad idea.

I think we need to undo a lot of that education. Yeah. And that's why I think Teachable is so important and why what we do, I hope is important for people. You know what else is weird? People hate online courses and people hate online education. Like they equate it with like if you can't do, you teach or that it's all scams. Why do you think that is?

I also think when we, we haven't gotten there, but at some point the way online education works, we're going to look back on what it is today and laugh. Because today when you look at online education, it is. is really just a mishmash of old formats delivered. It's like, oh, we used to have videos, let's take videos and let's like throw, we're basically doing the old paradigm now. And I don't have better ideas yet,

but someone will and we kind of need to rebuild education in a way that's digitally native. Almost like a duolingo advanced version, etc. Or I'm sure it'll vary a lot by what the, what's your hottest ideas, what you're learning. I mean, for me, what's always worked is just doing stuff. Like, even in, like, again, even in college, like, yes, I would eventually study because there was a test.

But, like, I only learned how to do anything, whether it's coding, building a business, like, playing a sport. Like, really, the majority of it comes from doing the thing. That's so true. Yeah, so it almost has to be. I mean, that's the same. When we think about our curriculum, it's you first, you learn to some level, but simultaneous with learning. you have check-ins that basically make sure you're learning the right thing at the right time. And then you have execution, which is like take a little baby steps that can't ruin your life to start.

And then you start taking more and more aggressive steps where by the end of the learning, you should have fully been done with the doing. Yeah. But we don't have any fancy tech on it yet. And I do feel like that's the future. Yeah, I think like just getting people to, because online courses at Teachable will we saw is like 50% of times people wouldn't open the thing. I know. When you charge more money, you actually got better results, ironically.

A lot of people were more likely to take the course, more likely to report a happier satisfaction just by charging more. So that helps a little bit. But even then, people are their own worst enemy in a lot of ways and trying to find ways to beat that. Yeah, I also think that's fascinating. People do not value the stuff that they do not pay for. That's another reason why we charge whatever we charge because I just haven't found a way where people will actually do a thing that they do not pay for. It almost becomes like cute to download

and no desire to execute. We saw that repeatedly, which is why I think, I mean, this was a wild back, but we, every single year, for many years, we looked at our most successful creators, the average price kept going up and up and up. What we found is most creators

could double their price and see no change in conversion rate. Whoa, that's wild. Because there's, I mean, the other side of that is people were always afraid of charging their worth, especially if there were new creators, they always felt like, why would anyone pay me for this? Like, my information is not that valuable. So they're all undercharged. What would you say to somebody who was afraid to charge with their worth? I would tell them, even though this sounds crazy, double your price and

work backwards. Let's say double your price. There's no way it's worth that. Okay, what would you have to change to make it be worth that price? But you're just doubling it. Like, that's, that's just take that as a given and then work backwards. That's really smart. What other hacks have you learned from building two companies that are arguably both worth nine figures? So one caveat I'll give is I felt very smart after running a company the first time. I've learned everything. When you do it a second time, you realize to do get good at something, you do it hundreds of times. So while I feel good about our strategy now, it's just quite likely we'll make a second different set of mistakes. Yeah. But I think the lessons that have kind of stayed with me is, one, the types of people were hiring.

The first time around, I focused a lot on pedigree, like what company you worked at, where you went to school. What I found is a lot of that stuff doesn't matter as much as you think it does. Like a lot of times you find someone from a very impressive sounding company, they haven't actually done the thing. like Stripe or Google is not successful because of their contribution. They just stayed there at the right time and the right place. But finding someone who uniquely wants to be at a startup wants that kind of challenge is been much better. What do A players look like versus B or C players?

So the one caveat is I can do a lot of things to try and identify them, but I will get one out of every four hires wrong. And if you work with that construct, you can be smart about it. So wherever possible, I love to have people contract or do something for a couple of months because you can always tell after you start working with someone if they're going to be good. In fact, I almost never had someone who starts out great, who isn't always great, or someone who is a poor performer who you're like, oh, let me give them more time. Do me neither. And I got killed on the internet for that. I got totally, yeah, I think the tweet

was like, like the way it starts is the way it will be. If you start out as a bad performer, you will never be a good performer. And never is always a triggering word, but it's actually never. I've never once had somebody that started poorly that circled around. I've still, like, which is why I don't think like, you know, PIPs and performance improvement plans really truly work. And sometimes I think they do a disservice to both the employer and the employee. But the takeaway for me is like, okay, if you can kind of test the waters, work with

someone as a contractor before or something, that helps a lot. Yeah. And like the other part, I say everybody gets mad when you think about poor performers versus not. But the other thing is just like fit versus not. Yeah. Because, you know, we're kind of psychopaths. So like our businesses run really fast all the time. That's a very important caveat.

When we say poor performer, it doesn't mean this person will be a poor performer everywhere. It's just like there's probably a place out there that they will do great at and you're kind of holding them back from finding that. Yeah, 100%. What if somebody wants to be an A player? What do A players do? Great news. The federal EV rebate is back. Eligible customers get up to $5,000 with the federal EVAP rebate on select 2027 Volt and 2026 Equinox EV models. Visit your local Chevrolet dealer today for more details. AI is moving fast across the enterprise. But without visibility, it's just chaos, different tools, different models, different teams using AI in completely different ways. Service now turns that chaos into control. With the AI control tower, you see all your AI across the business in one place.

What it's doing, what it's done, and what it's about to do. So you stay in control. To put AI to work for people, visit servicenav.com. Again, it varies by the role, but to me, an A player is someone that I don't have to give initiative to. I don't have to tell them what to do. They're one step ahead of the game. They're always thinking of how to make the business better. And for a lot of roles, like, I am learning from them.

right? Like there's a lot of areas where I don't know. It's hard for me to identify the functional parts of why someone is an A player. I need them to actually tell me. Yeah. Is there something that if somebody does this, you automatically go not going to make it? It's, I think when people, we find people that are just looking around, looking for what things to do, and they aren't really taking that initiative that I think makes it. very tough. The other thing, and this is my own bias, like, there are some cultures that are measured twice cut once. I am the opposite. I'd rather have a frenetic pace of execution, even if you make more mistakes. Because for our kind of company, speed is one of the only

advantages we have. So I index a lot in people who move really fast. Yeah, me too. It seems like a common trait, actually. It is. But I'll be careful to say, like, as an example, right? I think Apple is a phenomenal company, like one of the best of all times. Their culture is so different and it works. They're very secretive. They will potentially take many, many years to build something and build something beautifully. Figma did the same thing. They didn't release a product for four or five years. I couldn't do that. It's on my kind of company, but I want a caveat for the right type of founder, there's a way of doing that. It's just on my style. My style is frenetic.

We'll build in public. We'll fail in public. We'll launch bad things. The things will launch will eventually become better. Yeah. Yeah. Same. Although, I mean, I've never built something as hard as a SaaS marketplace.

Like a marketplace in general. Like we're building BizCout right now. Fuck my life. That thing's hard. Yeah. I mean, three-sided marketplaces, which is what you build. Yeah. But the thing with marketplaces, what we found is they take so long to scale.

Like, it was kind of demoralizing and teachable. It took us a few years. is to hit a million in annualized revenue. And we'd have creators come in, use our platform, make a million bucks in like two months. Like, what are we doing wrong? But once you get the flywheel going, it's just amazing and stays.

Yeah, yeah, yeah, yeah. I really understand why. But the cool part about marketplaces are those are moated in a world in which increasingly technology will not be moated. Yeah. So, like, somebody could go build the same duplicate of what we have. People use price lists, which is kind of crazy.

Oh, yeah. And it doesn't have like the highest revenue per, employee company out there is Craigslist or something? Yeah, I think it's, by the way, I think that'll change. There'll be a billion dollar company soon with one person and all of that. But for now, yeah, it's getting there. Yeah, but I do think the cool part is like thinking in today's age, given technology and how fast it's moving, what are the areas where there's a human differential? I think distribution is probably going to become more important than it already was. Yeah. because if the cost of building something goes down to almost nothing,

reaching people becomes the most valuable thing. The other thing that I think is a way of... So you're going to start a YouTube channel? Not yet, but... But I mean, distribution does matter. Well, you guys have X that you're doing a ton on plus. You're starting courses yourself for people to learn. So distribution makes a huge difference.

The other competitive advantage we have, and no one thinks of it as a competitive advantage, because the shittiest one of all is regulatory stuff. Oh, yeah. Like, we are a regulated organization. organization where, you know, RIA, we're going to be a broker dealer. Even if AI makes it really easy to do stuff, the SEC is not going to prove people in two days. Finra is not going to prove people in two days.

So regulatory modes, I think, are real and will continue being real, even as everything else gets faster. That's a great point. I mean, we think about where AI took over first. It was graphic design and, you know, copyright and all that zero regulatory mode. Whereas why couldn't it take over accounting? Yeah. regulation.

Yeah. Even like, like I think, I think the AI to help lawyers will be very good and exist for many more years before the AI that lets you replace a lawyer because you're still going to want to have your lawyer when shit gets bad. 100%. And you want CYA. So, yeah, I totally agree with that. What do you think, like when it comes to, we talk about them like mercenaries versus missionaries. So we love investing in second time founders of what you are. So that was sweet.

and people who have lived the problem for a long time and felt their pain personally. You've invested in a ton of companies by now. Is that important to you too? Do people need to live their pain point or just like come up with a random idea and who has a higher likelihood of success? I think it's just so much easier. Like as an investor, if I see a company, I'm less biased. Like I'm fine with either type. But if you were a friend telling me I want to start a company, how do I maximize my chances of even getting funded?

I would say solve your problem. You already know who to build for. It's easier to find customers. Like, yes, you can build a successful company, building vertical SaaS for construction workers, but it's going to be really hard because you're spending all your time to learn their problems.

You skip so much stuff by building for yourself. So that's always my best advice. Yeah. In terms of patterns for founders I've seen, honestly, have seen a good mix of both. The part that surprised me is during bull markets, how little some founders have cared. which sounds kind of crazy.

But like when I raised money, there's a sense of fiduciary responsibility in a way that the company may fail, but people are entrusting this on me. So even if things get really hard, I'm going to have like internalized that pain and try and work through it. But we saw a lot of companies

who raise money during good times as soon as things get hard. They're shut down their business or you know, kind of just walk away from the fire. Yeah. Yeah, we have a mutual, we have a mutual friend. I'll tell you afterwards so he doesn't murder me because he's on the internet too, but who had a company and he forwarded me the email. He's like, can you believe this? I was like, yes, I can.

Because the email was from a founder that raised a bunch of cash and then been like, you know what? My mental health is really struggling. You know exactly who I've talked about. I've seen that email. And then, and then like asks for like a couple month vacation to like. He's, or they sent me like to forwarded the text. Like what the hell is this? Okay. We were on the same thing. And listen, mental health is a real thing. But I think one of the reasons it's important to talk about all this is if you're going to do a startup, especially a venture-back startup, expect massive mental pain.

Just expect it. And if you don't want that, that's very healthy of you, quite honestly. Probably better. It's just that there's a sense of fiduciary responsibility. Yeah, do another business. Again, one of, I don't want to kind of name them without one of the companies we both invested in is the opposite of that where the founder did not have the easiest time of fundraise in a very hot market, but now as a result, they're a stronger company, and they're better

for it than every single company that had a really easy time fundraising. Yeah, it does. It definitely, that's the steel and the fire, you know. I also liked what Brett Adcock said about figure. Did you see his quote on, what did he say? He said, every company has two things. They have a speed, so magnitude, and direction vector problem. And if they get either one of those.

too wrong magnitude or vector they'll lose. Interesting. I thought it was a really good quote. I mean, obviously a dude who reportedly, as we're supposed to say, has a $47 billion valuation and getting to watch him sort of inside the back end a little bit. Talk about somebody who can handle massive pain. I can't think of a worse company to build than robotics. That's so hard. But kind of gets that speed matters and direction.

And if you can hit those two things, you don't have to be that much smarter. Yeah, I don't think, like, I don't think raw intelligence is that helpful. Like, if I think about what are the things, like when I'm looking at a founder, personally the things I look for is do they have what I call raw horse power, but it doesn't have to be intelligent. It could be capacity for work or whatever. But do they have that? Are they able to move really fast?

And are they able to convince people to do things? The third thing is the thing you realize. You spend most of your time trying to convince people to do things. You try to convince investors to give your money, convince customers to use your product, convince employees to join your team. So how convincing is someone? And I think that ends up being really, really important. Yeah, it's so true.

Yeah, I mean, I think, I remember Noah Kagan, who we were talking about before, a mutual friend of ours, he would say to me, like, you're the hardest working, you know, person I know online or something. And I remember at first, I was like, no, I'm not, Noah, I'm really smart. And, you know, don't just say I work hard. But as I've gotten older, I realized that there is just a huge value. you to being willing to put the nose of the grindstone. And it's kind of gone a little bit out of favor,

or at least it was for a few years. It was like, I love Gary Vee. But it would be like, Gary Vee, stop it. Like get off with the hustle point. And then I love that clip from Timothy Shalomeh. Shamae, what the fuck's his name? Where he talks about just like, I want to be a great. Yeah.

We got very soft, I think, as a culture for a while. And it's funny because if an athlete says that, like, I want to Kobe Bryant, well, you know, like, yes, let's do it. But yeah, as a founder as an entrepreneur, we tend to expect the results without being willing to put in the work. Yeah.

Okay, I want to do a couple of rapid fires with you that made me think of something. One of the books I'm reading right now, I want to hear yours, is I've just read like every book I possibly can from Phil Jackson from his time leading the Lakers and the Bulls. I couldn't tell you a fucking thing about basketball, but the leadership components of it are astounding

and how they had to like pair together the team. Plus, I didn't realize He was a Zen Buddhist the whole time, which is wild. You probably knew all this because you're a dude. But I don't know anything about that. So I'm reading that book. Is there anything right now that's really inspiring you that you're reading? I think the book that got me started down this entire path and I still periodically reread it is Richard Branson's book.

And the reason, like, okay, the business is great and all of that. But there's this, like, spirit of him just having a fucking blast while doing this, which I find to be kind of healthy, right? Like, yes, he works really hard. He starts a lot of businesses, but he's doing it for the love of the game. And he's having a really good time doing it. So I find that part pretty cool.

Ironically, I read a lot now, but I probably spend 70, 80% of my time reading non-business books. Like, I just find reading enjoyable. Like fourth wing? Are you a fantasy guy? No, not fantasy. It's only for women.

No werewolf smut for you copy. Yeah, but no, so like business books have their plays. So what do you read then? Lately, lately I've been reading a lot of Ishiguro, Japanese fiction. Interesting. Yeah, just, you know, I'll pick an author. I'll get into it. I'll read everything that written.

Yeah. I find it relaxing. It's my like nighttime, like, turn off work routine. If you haven't read them, there's two books called Adventure Capitalist and Investment Biker. Have you read those? Why does the name sound familiar? Because it was Soros's partner back in the day. Jim Rogers, who was like, they had the best performing hedge fund for like some five or 10 year period.

Then he just bails. He's like, I'm out. He takes his money and he goes and rides a bike all through Russia. Yeah. And then it's pretty awesome. Yeah, and it converted like convertible all through Africa and Latin America. Anyway, the point is, yeah, go ahead. That's just fun.

He invests a ton while he's doing it and adventures, which I think is a cool. Yeah. It made me also realize when I read this thing was called More Money Than God, which is about hedge funds, how much easier our lives are as a venture capitalist because when these hedge fund people make a mistake, they take down the economy of Thailand. Like, you know, like really bad things happen. Like, here, cool, invest the company, company fails.

Oh, your bet against the pound failed. But now seven countries are in a depression and you've like thrown off the entire global economy because you took a levered $43 billion bet that you got wrong. Yeah, it is. It's a little bit of a zero-sum game, which I never like. because entrepreneurship doesn't have to be. But yeah, I saw somewhere that like the global,

what was the tweet? It was like the world is like $417 trillion in debt. It was like, who are we in debt to? Like the emoticons or something? Yeah, the whole thing is sort of like, the global financial crisis where like Iceland like levered up 40 times and just blew it all.

It was just, yeah, it's like countries drunk at the casino. Yeah. But I do think one of the good parts is like to wrap it up And I'd love to end with this last question is like, you know, at the end of the day, we can focus so much on all the high level things that are happening in the world, totally out of our control, who's in power, who's not, whatever. Or we can just build something. So if there's a builder out there needing a little inspiration, what would you tell them?

There's nothing like actually going out and doing it. Like the amount of people I've spoken to that are like constantly stuck in the analysis, paralysis stage of like trying to find the perfect day. find the perfect brand name, trying to find, you know, the perfect logo versus just going out there, putting yourself out there, asking someone for money and doing the thing. Like, that's really what it comes down to. Carrie, and what's your handle on Twitter and Instagram? So everybody can slide into it.

My full name, Ankur Na on Twitter, on Instagram, Uncle N.A. And yeah, carry.com, which was worth a lot of money. So they're all just going to slide into your DMs. Both women, now that they know that you're single, you're welcome. And also people asking you for money. Perfect. You've got all kind of gold diggers in the mix. Anker, thanks for being here.

You're the mayor. Thanks for having me. And now let's hear from Anker on his postcard. Even though it may seem like it at the time, there is no amount of time that you will spend with your parents that you will ever regret when you get older. Oh, now I'm crying. That's so lovely.

You're the mayor. Thank you for taking. Thanks, ma'am.