AnkurNagpal

LubaHi everyone. Welcome to Flatiron, New York. And I'm drinking my favorite, or one of my favorites, Blue Bottle Coffee. I'm here near the AngelList office, and I'm here because I am having a conversation with Ankur Nagpal, the founder of Teachable and the founder of Carry. Carry recently sold to AngelList, and Ankur became a GP at a public markets fund that is run by AngelList.Link

And I can't wait to get into his second exit. How he's feeling, the decision to be an employee, which is kind of wild because he's pretty much never been an employee at a company. His favorite books, mindset of a founder, how he invests, and so much more. So tune in for my conversation with Ankur. I'm really excited to chat with him.Link

AnkurAs I walk into a tree. Walk in there. Number three. Total obstacle course. Okay.Link

LubaCongratulations. How does it feel to have sold two companies?Link

AnkurIt feels like a little bit of a relief, to be honest. But no, you know, building startups is something I've been fortunate to spend the last ten years doing. And exits are always a fun part of it. But, yeah, it feels pretty good.Link

LubaYeah. That's amazing that, you know, you weren't like a one-startup wonder. You were a two-startup wonder.Link

AnkurOh, that's what they say. Once, you're lucky. Twice, you're good. Except I still don't think I'm very good. But, yeah, it's rewarding to get to this place.Link

LubaOkay, so tell me more about this not very good part. Like, why do you say you still think you're not very good?Link

AnkurI think running a startup just ends up being a very humbling experience because, I mean, as you and I have talked about privately, like, yes, the exit feels good, but right up until that point, you feel like you're getting your ass kicked, kind of. And so much of running a startup is just realizing you're not very good at a lot of different things.Link

So yeah, I sold the business, but in my mind, I'm still like, man, we could have only been better or grown faster or done other things. So my mind is still more fresh on all the things we couldn't do. Yeah. Versus what we did do.Link

LubaSo did you feel like that when you were about to sell Teachable?Link

AnkurSelling Teachable was interesting. Even then, our growth had slowed down, and it looked like... Because I think when you sell a company, typically as a founder, you're still calculating the exit path where you think you're better off taking the deal. That typically means at some level, you've lost some level of optimism or love for the game or whatever. So even with Teachable, while the offer was very exciting, part of it was like the work ahead to get our revenue growing really fast again seemed...Link

LubaVery different.Link

AnkurExactly. Ironically, right after we sold Teachable, COVID happened and revenue grew faster than ever before. But we couldn't have predicted that.Link

LubaYeah, that's very true. So what are the things that you feel like you were not good at running Carry? The same as you were kind of reminiscing on when you were running Teachable, or were they...Link

AnkurYou just make a whole separate set of mistakes every single time. With Teachable, look, I was 24 when I started it. With Carry, I was 31 or 32 or something. So you're a different person at that age, and the company kind of reflects your personality. With Teachable, a lot of things worked from the outset. With Carry, because I had a relatively large audience from day one, the market signal was not the strongest, in that people always said nice things no matter what.Link

And ultimately, with Carry, I think we built a very, very good product for quite a few people, but it never crossed into the mainstream. You know, we were at 4 million in ARR after about three years, which is just good. It's a good business, but it's not fantastic. Yeah.Link

LubaSo I love the fact that you're always so honest. You're like, ah, you know, this was a solid business.Link

AnkurDisapproving Indian parents, you know, just drilled it into you. Which is honestly a lie. My parents could not be more supportive. But yeah. Look, you know, I want to call a spade a spade.Link

LubaBut why not, you know, put it up as like this triumph? "Oh my God, it was so scary. We're now a part of AngelList." You know, I mean, a lot of founders do that, hype up their exit no matter what the exit is like. Why are you not doing that?Link

AnkurI think a lot of people who do that are suffering from, like, a kind of deeper form of insecurity where they don't feel comfortable telling it how it is. I think I feel very good about myself, and I think you get a lot of credibility by being honest, both in personal relationships around me, but also when people listen to me or see something I write. I think those who know, know. And the most legit founders are the ones who appreciate it the most, versus sort of this culture of false bravado.Link

LubaYeah, I agree with that. That always got to me in the Valley, where, you know, you go to a founder...Link

Ankur"It's crushing it."Link

LubaYeah, exactly. Everyone's crushing it. Everyone, like, raised all these rounds. And that's the most vanity metric that people talk about. And even though I think I was kind of looking up to those people when I was working, before I was a startup founder myself, after I started being in those circles and realizing that, okay, building a business that works is so freaking hard, and it's much harder than, let's say, raising money, even though it's a different skill, I just hated that vibe of people always hyping themselves up.Link

AnkurI also think, by the way, as an immigrant, some of this is cultural, where in a lot of countries, self-deprecating humor is a thing. But Americans don't really self-deprecate that much. If you listen to like British TV or British humor, everyone makes fun of themselves. You intentionally talk down on yourself as a joke. America is the opposite. Everyone has this sense of bravado, and "we're crushing it," and things are amazing and awesome and incredible.Link

LubaYeah, it's part of why America is so good at sales. And maybe... I mean, I think you're really good at sales. I think I'm still very much learning how to do the hype in a balanced way.Link

AnkurI think I'm okay. I think I'm okay at sales. It depends on what it is. If it's something you're selling, you want to have conviction. And yes. But yeah, it's all part of the game.Link

LubaOkay, so you said that you feel really good about yourself, and people who do this, like hype up, probably have some sort of insecurity. Did you always feel really good about yourself, or was it a learned journey?Link

AnkurI think firstly, like baseline, of course everyone has some level of insecurity, but I do think the more you actually see good results happen, good things happen, yeah, the more confident you get. I also think age is a big factor. Like, I think you truly become who you are at around 30, late 20s, 30, somewhere around there.Link

Where there's a lot of things that, like in your early 20s, you pretend to like stuff because other people like it, and you kind of mimic behavior and all of that. By the time you become 30, you're like, I am who I am. You know? I can't be changed at this point. And you kind of settle into that. And yeah, as a result, as you get more assured in who you are, I think it leads you to being more honest.Link

LubaSo you never had to go through some sort of love-yourself journey, or meditating a lot, or... You're sort of the happy guy.Link

AnkurNo, I think it's more like... Maybe it's being an immigrant, but I think the whole self-love journey, to me, it all just feels like the culture that I see in the US, where it just doesn't exist the same way in other places. Like, I remember I was even at work, and someone was telling me their pet is on antidepressants, and that just seemed insane to me.Link

Yeah, yeah. Like, your cat can have anxiety, apparently. And I was like, this sounds insane to me. Like, we were joking, there's probably more pets on anxiety meds in Brooklyn than people in India. Right. Yeah, it's a different culture.Link

LubaWell, I think part of the problem is that we talk about it so much. So once we start talking about something so much, then people start putting labels on things.Link

AnkurOf course, but I think that's sort of the culture you have. You can give vocabulary to anything. I'm not saying suffering is part of, you know, human nature or whatever, but you can always come up with fancy words for it. But I think part of it is just kind of getting on with it.Link

LubaYeah, that makes sense. So after you sold Teachable, would you say that you were leaning into the same strengths that you figured out you had at Teachable when running Carry, or were you like a completely different type of founder?Link

AnkurSo when I first sold Teachable, I was very burnt out at the time. I remember prior to selling Teachable, I was not sleeping super well, and I started getting into, like, all these people online are like, "Oh, you need to have no alcohol. You need to have a dark room. You need to take all these supplements." And I was doing all of that stuff, and I still wasn't sleeping great. And then I sold Teachable, still wasn't sleeping amazing. But then I stopped running the company, and I slept fantastically.Link

Wow. So clearly there was a baseline level of... That's the other thing. You know, all of this health hacking, longevity hacking, I think the single most impactful thing is stress. Like, just mentally being in a really good place.Link

So after Teachable, I was like, I want to spend none of my time doing this again. I want to, you know, travel the world, take some time off. And I did that for almost two years. It was super fun, super rewarding. But I eventually started to miss the idea of building something with other people. And that's what drew me back to Carry. And, you know, that ended up still being one of the most valuable parts of this.Link

LubaOkay, so now that you've sold Carry, you're not, you know, peacing off to go travel. You're actually becoming an employee, which is almost the first time in your adult life.Link

AnkurYeah, I had an internship when I was 18. Right? I was an intern for a summer, but since then, this was the closest. Yeah, this is the only time I've worked for an organization that is not my company.Link

LubaYeah, so what the heck? It's like adulting.Link

AnkurNot a bad life. You come in, you get paid no matter what happens. You're not the one writing the checks. But no, I'm kidding. The opportunity here is very interesting, and that is what drew me to this, where we get to build a public venture fund, which is an insane concept, and it just combines a lot of the things I'm interested in. So it felt like a very fun thing to do.Link

LubaOkay, so I want to talk about what USVC actually is and how it works. But before that, at which point did you realize that, okay, Carry is a solid business, not a venture outcome? And what was that gap or distance between realizing and actually acting on it?Link

AnkurAgain, I was very fortunate in that I was not looking to sell the business, however...Link

LubaOh, you were not? Okay.Link

AnkurI was not looking to sell the business. I was like, look, this is our destiny. We're gonna keep growing, keep compounding, keep figuring this out.Link

LubaAnd what was driving that? Like, why did you want to go...Link

AnkurLike, still, this is a battle that I've signed up for. We have a good team. Things are working well enough. We back ourselves to figure it out. However, I've known Avlok from AngelList for a while. I know Jeff, who's ultimately on AngelList's board. They reached out a couple of times for me to run USVC, and at every stage I was intrigued because the opportunity was cool.Link

Yeah, but you know, they then suggested, they're like, "Hey, look, if you're running Carry, maybe there's a world where we can acquire the business." They liked a lot of what we had built at Carry in terms of growth marketing, being able to explain complicated financial products. "But maybe we'll absorb this into AngelList, and you can then kind of still do financial education."Link

LubaAnd how long were they courting you?Link

AnkurPretty quick. So they courted me for, I would say, about 4 to 6 weeks before we ended up deciding to.Link

LubaWow. So not that long. And at that point, my understanding is that they had to jump through a lot of hoops to actually set up the entity and deal with regulation, right? So they must have been dealing with it for like a year.Link

AnkurAbsolutely. So USVC has been a project of Naval, who was the original founder of AngelList. USVC was his vision for what venture investing should be for the last ten years. So forever. And they've spent a few years getting the legal structure in place, and then spent at least the last six months looking for the person to run it. So this has been something they've been working on for a very long time.Link

But then when they came to me, my approach was like, look, this sounds intriguing, but if we can find a way to make this a good outcome for my team, for my investors, for all the company shareholders, we'll consider it. And that's sort of what kicked off the conversation.Link

LubaGot it. That makes a lot of sense. And so why is it so complicated to set up a public markets fund? Assume that I don't know anything about public markets funds.Link

AnkurI also, until recently, knew very little about it. But the biggest reason is in the US, there's accredited investor laws, which say you cannot invest in a startup unless you are an accredited investor. Yes. And what that means is you need to have a net worth of $1 million or make $200,000 multiple years in a row to invest in a startup.Link

Which to me seems a bit insane, because you can invest in any crypto scheme. You can buy lottery tickets, you can sign up on Polymarket and bet on how long Trump shakes someone's hand. Like, you know, all these insane things for people to lose money, but you can't invest in a startup. However, with USVC, AngelList was able to get SEC approval to offer venture investing to anyone with as little as $500. This was pretty big from a legislative perspective, because historically this wasn't allowed.Link

LubaSo this was a bill that passed recently?Link

AnkurThis was... I don't want to misspeak, especially on the record, but this is something that we got approval for after many years of back and forth to find the right structure to enable this.Link

LubaOkay. So how does it work for the startup's cap table? So let's say I'm an OpenAI, or maybe I'm a much smaller startup, because my understanding is that USVC can invest in very small startups too. Like, how do I give that allocation to a public fund? Do you guys approach the startup? How does it work?Link

AnkurYeah. So right now it's basically my job as a portfolio manager to decide what it is we want to invest in. And we can invest in almost any way. We can go buy stakes in a startup directly. We can invest in funds. We can invest in SPVs, which are one-off vehicles to invest in a company. We can buy out fund investors, fund managers. We're very innovative in the structure.Link

However, for the positions that the portfolio already has, most of them are through funds for now. But my goal with time is to start doing much more direct allocations and keep it a lot more efficient. But either way, it's us typically picking what we think to be the most important technology companies of the next 100 years, and investing in them before it becomes obvious to everyone else.Link

LubaAnd so why would I, as a startup, want to have USVC on my cap table?Link

AnkurThat's a great question, and one we're trying to find good answers to. I believe for a lot of startups... Right now there's this narrative amongst a lot of people, especially mainstream America, that technology is bad, AI is evil. And I think part of that is because the common person...Link

LubaThere's no access, right.Link

AnkurHas no ownership. They don't benefit from this at all. So I believe by creating a vehicle...Link

LubaLike actually...Link

AnkurBy creating a vehicle to give regular people an actual stake in the business, I think that can be very meaningful in changing public perception.Link

LubaRight? Because at the end of the day, it's all about incentives. And if people make money, then obviously they're going to be a lot more positive.Link

AnkurAnd right now what you're seeing in private markets is companies are staying private much longer. Like, Apple went public at like a $1 billion market cap. Like Shopify, even recently, like recently being 10 or 15 years ago, went public at a $1 billion market cap. But now you have these companies worth $1 trillion, and you still can't buy them. So the goal with this vehicle is to kind of give ownership. And my hypothesis is companies will want this because they can now have regular people be stakeholders in this.Link

LubaYeah, that makes sense. So by allowing regular people to participate, they will lift up the narrative and change the narrative. That makes a lot of sense. If I'm investing $500, like the minimum on USVC, what can I actually expect? How long is the money locked up? I know that you're making a gamble because it's private markets, but yeah, like, will I make a ton of money?Link

AnkurWell, I have to make all the disclaimers.Link

LubaCareful, careful, careful.Link

AnkurI have to make all the typical disclosures and disclaimers. Like, venture capital is an illiquid asset class. It is risk capital. You know, think of venture capital as risk capital. Do not do this with money you need on any kind of short-term basis. The whole idea is this is where a small, speculative growth part of your portfolio can live.Link

With those disclaimers out of the way, the way it works is when you buy into the fund, you effectively get shares at what we call NAV, but it's effectively a share price. So right now the NAV is about 20 bucks, for instance. So if you spend $500, you get, you know, 25 shares or whatever. And every time there is a change in the valuation of the underlying companies, the value of the fund goes up or down. And every quarter, our goal is to provide liquidity, where up to 5% of the fund is made available for anyone to sell out of. So as a theoretical example, you buy in at 20 bucks, maybe it's 25. You could potentially liquidate some percentage of your holding every single quarter. That's roughly how it works.Link

LubaOkay. So like 5% of the holdings.Link

AnkurNo. So it's 5% of the overall fund. As an example, let's say the fund is $100 million. There'll be 5 million of liquidity available based on who wants it. So you can potentially liquidate much more than 5% of your holdings if no one else is liquidating.Link

LubaGotcha, gotcha. And so how would you think about the percentage of your portfolio that you need to allocate to private markets? Do you think about it the same way as if someone had access to angel investments?Link

AnkurI think it's very similar. Numbers vary by person. And, you know, we legally can't give investment advice, but I tend to think for a lot of people it's small. Right. It's like 5%, 10%, whatever. For me personally, it's insanely high. Like, I have like...Link

Luba30%, right, or something?Link

AnkurLike that. I think right now it's about 50%.Link

LubaOh, wow. That's crazy.Link

AnkurI wouldn't recommend this, but...Link

LubaWait, why did you allocate such a big percentage of your portfolio?Link

AnkurSo to me, look, we all are in startups. It's such a core part of what we do. I'm more bullish than the average person. I also am fortunate...Link

LubaTo have more information than the average person.Link

AnkurI'm fortunate where I have multiple exits, so even with half allocated in public equities, it's enough that even if all the startups go to zero, I'll be okay.Link

LubaRight. So I love the fact that you shared your fund performances. Like, how many startups have you seen now? And how many startups have you invested in?Link

AnkurInvested in a little over 100.Link

LubaWhich means probably like 1,000 seen. Yeah, yeah. And then I saw that you had Spearhead one and two. So were you a part of the Spearhead program? That was your personal fund that they gave you, liquidity?Link

AnkurThat's how I started investing, with this program called Spearhead. For anyone who doesn't know, they gave a bunch of founders $1 million. They said, go pick companies and see how you do. That's what got me started with investing.Link

LubaAnd you did pretty well in those funds, one and two.Link

AnkurAgain, it's venture capital. The difference between a very successful fund and a not very successful fund is one outlier company. Yeah. So it's crazy.Link

LubaWho are your outliers?Link

AnkurI can't.Link

LubaYou can't?Link

AnkurI don't want to name, because I have a lot of good companies. I don't want the other ones to feel bad.Link

LubaThat sounds okay. So based on everything that you've seen, now that you're seeing founders, what would you say makes a great founder? Can you tell right away?Link

AnkurSo, three things that I look for in founders. And this is my personal decision-making process. Everyone has their own. Yeah. One, I look for someone who moves very fast. Like, I'm a very fast thinker, fast talker, fast everything. Speed of execution matters a lot, because a lot of times it's very hard to tell what's going to be successful. So the faster you try different things, the more likely you are to find something.Link

Yeah. The second thing I look for is something I just call horsepower. This is just raw ability. It can either be intelligence, work ethic, whatever. Like, some people are just really, really smart, and that's super important. The third thing I look for, and this is a bit controversial, is how good are you at convincing people to do things? I think this is controversial.Link

LubaWhy is this controversial? That's like resourcefulness or magnetism.Link

AnkurBut even if you think about it, okay, most of the founders that end up going to jail, guess what? They're very good at convincing people to do stuff, right? But running a company, you have to convince so many people. You have to convince investors to give you money, convince people to join you, customers to try your product. So people that are convincing. Those are sort of the three things I look for. Yeah.Link

LubaSo, sorry...Link

AnkurGo ahead. So I was going to say, what that in turn means is if you're a founder trying to fundraise, how can you apply that? I think as a founder, being scrappy, being fast. And one of the things I found very useful, I did this myself as a founder, is be very good at sending updates, not just to your actual investors, but even prospective investors, because it'll let you demonstrate that you can do all these things.Link

LubaYeah, for sure. So let's say someone's coming to you and they are pretty early on in their journey. How can you judge the speed of execution, because you're about to put in like a pre-seed check?Link

AnkurThat's exactly why the updates help, because typically you can't really tell that much about speed of execution when you get a single data point. Maybe you can ask them what they've done in the last month, last two months, last three months. But this is where seeing someone develop over a period of time, even a couple of months, you can tell, wow, these people move really fast. They're making a lot of progress.Link

LubaSo would you say that...Link

AnkurI'll give you one easy negative signal. If a founder is fundraising and they ask for an intro, and you want to talk to them, and they then suggest chatting in like 4 or 5 days, that's already such a bad negative signal. Because they should be like, let's chat tonight, tomorrow, right now. Pick up the phone.Link

LubaI think another thing is also desire. Like, how bad do you want this? Which I think is really hard to measure, because again, if you're really convincing, you're going to be perceived as someone who really, really wants it. Does that count? Is that a part of your equation or not?Link

AnkurReally, it should be, because I misread this. Some of my biggest investing mistakes were in the 2021 sort of hype, when everyone was raising money carelessly. I was surprised how many founders gave up the second things became hard, which clearly meant I didn't calibrate very well for how much pain they're willing to undertake.Link

Interestingly enough, if I look at all the people who fundraised during 2021, 2022, there's almost no correlation between how easy it was for them to fundraise then and if they're still good or successful or whatever. Like, some of the companies that had the easiest fundraising rounds, hottest deals, are completely dead in the water. And some founders for whom every round was a grind, they barely survived, are doing great now.Link

LubaYeah, for sure. I feel like you have to endure a lot of pain to be able to endure more pain, and if things just come really easy, you've never endured enough to keep going. Did a lot of companies fold within that one year, or...Link

AnkurSo when things got hard, I was surprised by how many more people ran out of emotional runway than actual cash in the bank. So a ton of companies ended up just being like, "Hey, this is hard. Like, I didn't think it would be this hard. And we're returning the money. We're done."Link

LubaYeah, well, I'm a good example of that. You know, I've been...Link

AnkurWell, I know you were... You embraced a lot of pain.Link

LubaI did, but I did eventually run out of emotional runway, and, you know, other things. And I did end up returning the capital, so that definitely happens. But okay, I wanted to ask something on emotional runway. How do you develop that aptitude for being able to endure a lot of pain, and for being able to really, you know, run through walls? Is there a way to do that?Link

AnkurI mean, if I were to be self-reflective, I don't know if I'm that good at it.Link

LubaWhat do you mean?Link

AnkurWhen things got tough, I sold my business two times now.Link

LubaWell, you were at Teachable for ten years. You were in there seven? Okay. That's a really long time.Link

AnkurIt's a really long time.Link

LubaYeah, but Carry was like three years.Link

AnkurThree and a half. I think it's tough. Like, I don't have the answer. I don't think I'm particularly good at it. I know some founders that are far more resilient than I am. However, I think a lot of times you're a product of the environment. Like, I remember back in 2021, everyone raised money so easily, they kind of forgot the gravity of how difficult it is to get a random person to give you a lot of money.Link

Like, I remember when I was fundraising for my first company, it took me three months before someone actually said yes. And along the way, there were people who said yes but never followed up. There were investors who basically did grocery shopping while I was pitching them. Just the worst, most disrespectful experiences. But I remember a founder in like 2021 would ask me, "How do you decide which investors to take money from?" And I was like, "Whoever says yes." Yeah, it's like, I don't care.Link

LubaContrary to the classic advice of, like, oh, you need to, you know, like them as a person.Link

AnkurRaising money was tough, and it sucks. So I don't care if you live in Iowa and are randomly rich from four generations. Like, sure.Link

LubaLike, wait. Have you changed your opinion about that? Because I think it is still important to work with people that you genuinely like working with.Link

AnkurIt depends. It's a factor of the market, right? Like, if it's very...Link

LubaIt's like dating. Yeah, yeah.Link

AnkurNo, I think dating is different. Like, with dating, you're actually spending time with this person. With dating, choosing to be single is a more viable option than it actually is for your business.Link

LubaIt is like dating. What I meant by that is, depending on whether there are more men or more women, that completely changes the dynamic. So it's kind of like... Yeah, yeah. But sorry, go ahead.Link

AnkurYeah. No, I was like, with dating, you can just be like, okay, I'm going to be single, because that is a perfectly viable alternative. But not funding your business is not a perfect... Yeah, yeah. Alternative.Link

LubaYeah, that makes sense. And that is actually what you mentioned about how easy it was to raise money in 2021. It was fairly easy for me to raise money at that time. And I actually felt really bad about it, because I was like...Link

AnkurWhy do you feel bad about it?Link

LubaI think it's still something that I'm dealing with, a little bit of a therapy session. I didn't have a lot of things to show for it. And so I feel like that was kind of part of the chip on the shoulder, too. That money came very easily. And, you know, you have this flying around, and a lot of people would have used it as this really glorious narrative.Link

AnkurBut you also had a brand-name investor, and that's when you saw that dynamic where there were so many people who wanted to follow the hype. Yeah. But for what it's worth, following the hype is always a thing. Like, I still remember even the first time, it took me three months to get to the first yes, but then the rest of the round happened, or something. Yeah, it was very quick.Link

LubaWhat are you looking for in founders right now, in, again, kind of a bubble and a market that's really, really high?Link

AnkurI think who knows if it's a bubble. It's hard to tell.Link

LubaAnd I guess that's what your public markets company is going to show, right?Link

AnkurNow, with the public fund, we're not investing in anything early stage ourselves, just because the universe of exciting early-stage companies is so broad, there's no way I have time to meet with them or keep up with them. So in early stage, we're investing in all the emerging fund managers, and they're effectively our eyes into that universe. That makes sense.Link

And then with later stage, it depends. Sometimes it's a case of, you know this is going to be a good company, how do you get access? And that's where I think being a public fund can be helpful. And then part of it is, being part of AngelList, there's such an advantage in that we see all of this powerful information, where we believe we can predict fund managers that are going to be good, companies that are likely to break out, and we apply that to pick.Link

LubaSo for a person who wants to build today, would you recommend them to build a solid lifestyle business or go raise venture?Link

AnkurFor almost everyone, you should not raise venture capital. I don't think people understand the effective bargain you make when you're raising venture capital, which is you're implicitly saying, I'm going to give up making any kind of personal wealth or whatever until or unless this business succeeds. I'm going to work irrationally hard for five, ten, 20 years. I'm going to underpay myself for this. And I'm only going to do this because I believe the company I'm building has a chance of being worth many billions, maybe tens of billions of dollars. For almost everyone, that's a terrible deal. That's not what you want. It's glamorized, but it's just not the reality. So almost everyone should not do it.Link

LubaIs there some sort of quiz or a test you can do on yourself to determine whether you should do it or not?Link

AnkurSo I think, look, if what you want to do is just a very hard problem... Do you want to build a nuclear reactor? You want to make people live to 200? You want to do something truly very difficult that takes a lot of capital, but it's very rewarding? It makes a ton of sense. But I think it's worth auditing if that is the type of funding you want to take, because you are effectively signing up to work super hard for a long period of your life with very uncertain reward.Link

LubaYeah, 100%. And I think obviously the fact that foundering, or founding a company, is so glamorized, and it's so easy to raise money... Everyone wants to have the accolades of raising a big round, but most people should probably not do it. So is there like one question someone can ask themselves to determine whether it's the right thing? Because, you know, there are a lot of businesses that are not a nuclear reactor that are still good.Link

AnkurI think it's scale of ambition. Right? Like, how much do you want to build something really, really big, even if it entails a lot of downside to get there? And the answer is, for a lot of people, it's not that important. If what you want to do is build a cool product and will it into existence, especially now, there's so many different ways of doing it. Yeah. Also, just candidly, do you want to be a billionaire? In which case, yeah, you probably have to build a company worth, you know, tens of billions of dollars. But for most people who want a high quality of life, that's not necessary.Link

LubaOkay. So then on high quality of life, your happy number is 10 million, right?Link

AnkurI think the number varies. I would say it's somewhere around there. Like, basically the point at which you're not stressed about anything, you can buy a first-class flight anywhere and just not worry about stuff.Link

LubaOkay, so that's your advice to someone who wants to determine their happy number. Like, think about the things that you really care about that you would want to splurge on.Link

AnkurFor everyone, it varies a lot. Yeah. For me, being able to take a long flight and lie down in one of those things, I'm like, okay, that actually kind of matters. Being able to have a house, if you have kids, and not worry about them. The numbers I've seen people go as low as, you know, three, four or five million, as high as 20, 25 million. It's somewhere in that range. It's very personal. Depends on where you live, who your friends are, a lot of different things. But yeah, for some people, that's just not enough. You know, they're very driven by, they want to be a billionaire or one of the wealthiest people in the world. And that's just a fully different personality type.Link

LubaDo you feel like money has changed you in any way?Link

AnkurI think it's allowed me to kind of lean more into who I am, and do what I want to do, and not do what I don't want to do. To me, the most valuable thing with money is just having freedom and deciding, yeah, actually, I'd rather not do that. Yeah, and that's been really nice.Link

LubaWhy are you so open about your net worth and all your financials? I mean, on the one hand, obviously it's really cool, but on the other hand, it creates, I'm sure, a lot of security risks and paranoia. Maybe for your...Link

AnkurI'm not. I'm open in how I think about these things. I don't share a lot of specifics, intentionally. And with time, yeah, we'll keep what's important from a privacy and security perspective in mind. With things like, okay, I allocate my portfolio this way, I think that doesn't present a security risk. And it's interesting information that I wish more people talked about. And I think more people are starting to talk about it, too.Link

LubaI guess I was just referring to, you know, being open money-wise. You shared about your expenses and costs, and that is a lot more detail than people share. Of course, those are details that you can deduce if someone is a public persona, but still, were you scared of sharing so much information?Link

AnkurI wasn't scared. I mean, money-wise, I basically was talking more about the spending side of things, and I've been pretty open about that. I tend to think more people should share that. The security side, I think, is real, but the damage there happens well before. The damage there happens when people realize you've sold a business, and, you know, things that are harder to control.Link

The other thing that is just the inevitability of being in media is anytime you do an interview, the interviewer or the social media people or the graphic people, whoever writes the headlines, focus a lot on it. So a lot of times it's even out of my direct control. Yeah.Link

LubaAnd do you ever comment on that? Because obviously money gets clicks.Link

AnkurYeah, there have been a lot of times I've had to have people change it and be like, what the hell is this? Or my mom freaking out, being like, "Please delete this right now."Link

LubaHow did you feel when you got the money in your bank after selling Teachable?Link

AnkurI mean, at this point, it was a very long time ago, but I remember it was a very strange time, because it was April 2020, which was lockdown. Full lockdown. I was in New York. I was in my apartment. I was living alone at the time. People were wiping down packages, everyone was dying.Link

LubaWashing their groceries.Link

AnkurSo it was very... You know, you have this vision that you're going to sell a business, you're gonna have a massive acquisition party, and it's going to be a blast. But no, in reality, I was locked in my studio. I eventually bought a car so I could drive to Rockaway Beach and go surf, because that was one of the only activities you could do at the time. And that felt nice. But yeah, nothing major changed or felt very different.Link

The thing that did feel super different was the day I stopped doing my job, the day I stopped being CEO. That improved the quality of my life. So that was a very clear example...Link

LubaOf how money creates freedom and opportunity for freedom. For someone who, say, makes 200 to 500K and still very much feels like they're on a treadmill, what would be one financial decision they need to make that would really change life for them?Link

AnkurI think at that point it's lifestyle. It's where you live and who you hang out with. Yeah, that ends up being such a big concern, because a lot of people, you try and keep up with the people you're around. So just potentially changing where you live, unless that place is suiting you quite a bit. So as an example, I've talked a lot about, I think people should never move to save money on taxes. But at the same time, you should audit what city it is that really kind of resonates with who you are and where you want to be, and all of that.Link

Beyond that, from a pure, okay, the personal finance nerd in me will be like, you know, make sure you're maxing out all your tax-advantaged accounts. Being smart about taxes realistically will save tens of thousands every year. But you're not just saving tens of thousands every year, because when you save that, that means more dollars getting invested, which means more dollars growing at, you know, 5 to 10% a year. So the impact of those thousands of dollars a year is actually millions of dollars over your lifetime.Link

LubaSo can you repeat that again? What exactly do you need to do?Link

AnkurYeah. So what people don't realize is when you, let's say, do something and it saves you 20K in taxes, people are like, "Oh cool, I saved $20,000." But in reality, you've saved hundreds of thousands or millions of dollars, because that 20K you've now saved is hopefully being invested in the market. And let's say the market grows, I don't know, six, seven, 8% a year. Over the course of your lifetime, that 20K is now worth hundreds of thousands of dollars. So every saving is not just the saving it gives you today, but it is what it compounds to over the course of your life.Link

LubaYeah, that makes sense. And I believe on one of the podcasts you mentioned that, okay, for founders, you don't really need to care about all of these ultra-optimizations, because you just want to work hard and have a big exit. Do you think they should do any...Link

AnkurThis is why being a venture-backed startup founder is so difficult. Your net worth is 99% determined by how successful your company is. So sure, you can do a little bit of optimization, but it's not worth optimizing anything if it distracts you from the main thing, because your main job is to make your company successful. So as a founder, sure, you know, do the basics. Don't go into debt. Don't do stupid stuff. But focus your energy on actually increasing the likelihood that you will be successful with your company. But for everyone else who isn't a venture-backed founder, I think all of this applies.Link

LubaHow would you factor in this math and the fact that most startups do fail?Link

AnkurIt goes back to: most people should not be a venture-backed founder. It is a bad expected value trade, right? In the outlier cases, you end up doing very well, but the average person who ends up starting a company will not do very well, which is why it's one of those, only do it if you're sure. It's also why, ironically, sometimes being young and kind of dumb is an advantage. Yeah. Because when you're young, your earning years don't feel as precious or whatever. But imagine you're 37 years old. You're making 4 or $500,000. You have two kids. For you to start a company now is incredibly expensive, because you're stressed. Like, what if this doesn't work out? What am I doing for my family? All of that.Link

LubaHow did you figure out what your zone of genius was?Link

AnkurSo one, it's always evolving. But I don't know, I thought back to being a kid. Like, what was I good at in school? What was I not good at in school? And I always found my superpower, or whatever, was being able to do a little bit of everything. Like, I grew up outside America. We never looked at that. We never diagnosed that. But yeah, I'm sure I have a little bit of ADHD.Link

But yeah, I have a computer science degree, but I was never the most technical person. I've always been a marketer, but I don't have the traditional sort of brand background. So just combining those universes, that I always felt to be my strength, which is why being a founder was good, because it's an interesting cross-section of a little bit of everything.Link

LubaAnd would you say you were the same type of founder at Carry that you were at Teachable? Like, were you very much leaning into the same strengths?Link

AnkurBut you do change and you evolve. I think at Teachable, I had no idea what I was doing. At Carry, I think I knew much more of what I was doing. But the market is the market, and the product is the product. So I think I evolved a little bit. But also, while we were building Carry, the whole AI thing happened. And you also have to evolve as everything keeps going on.Link

LubaWhat business would you start today?Link

AnkurI'm going to buy a sports team. Oh, yeah. I want to buy... Yeah, I bought a small stake in a cricket team. Maybe eventually I'll buy a larger stake. But I think, like, you know, everyone is getting into AI and building all these businesses. I think it'd be really fun to lean into something real-world, experiences. And, yeah, owning a sports team is pretty much... Well, actually, when I was a kid, I wanted to play in a sports team, but that ship has sadly sailed, so maybe we buy the whole team now.Link

LubaAnd what do you think your life is going to be like when you buy a team? Like, you just go to a bar?Link

AnkurI'm going to be the most annoying owner ever.Link

LubaYou'll be at the practices. You'll be my coach. Outside coaching.Link

AnkurThere was this article about this European billionaire, rich dude, or whatever. He bought a soccer team. Maybe this was in Norway or something. And the first thing he did is he put himself in the team, and he's, like, old, not as athletic. And all the comments were like, "That's pathetic. That's so sad." And I'm like, that's awesome. That's incredible. I would do...Link

LubaThat childhood dream.Link

AnkurI was like, I would totally do that. So that was great. But no, I bet I would still be the annoying owner where, you know, a lot of owners typically stick to the business decisions, but I would be the one, you know, in the draft, deciding who we pick and who we bench.Link

LubaAnd also on the bench as...Link

AnkurAbsolutely.Link

LubaAs a replacement, potentially. What are you worried about in this chapter as an employee? Do you think you'll be able to stay for a long time?Link

AnkurYeah, I think this is a bit atypical from being an employee, because I have a very clear mandate to build something.Link

LubaIt's just under an umbrella of a company, but you're a founder. Yeah.Link

AnkurIt's enjoyable. And to be honest, for now, it's kind of nice to not have a large team and stuff and be in a very specific role. As of now, I think it's a really, really fun product. So I don't have any bigger concerns over there. The question is, in 3 to 5 years, will I be like, oh man, I miss building a company again? I hope not. Every time I tell myself never again.Link

LubaWhy are you being pulled by building so much, even though there is so much pain in it?Link

AnkurMaybe it's the ADHD. I don't know. I also think the brain is interesting, right? Like, the way nostalgia works, your brain only focuses...Link

LubaOn the positives.Link

AnkurOn the positive. You forget all the pain. But I have a lot of friends who alternate between building a company, spending 5 or 7 years doing it, coming out of it, being like, never again, then spending three years being like, my life has no meaning, my life has no purpose. And then jumping back into it. But we'll see.Link

LubaYeah, that's totally fair. Yeah, we'll be watching what happens. Okay. I want to talk about AI and personal life. Are you using AI to run any of your life right now? And what are you using?Link

AnkurNot a whole lot. I use it for business-adjacent things. As an example, I think I was telling you about this, but I used it to run my LinkedIn. I used it to run my Threads. So it's business-adjacent. Like, it is still my personal social media, but there's still some business type of end goal for it. Otherwise, personal life is very, very limited. Like, small things. I've had a list of every book I've read since 2016, and now I'll have AI go in and create smart recommendations.Link

LubaOh, that's cool. And you actually follow the recommendations, and they're good?Link

AnkurYeah, they're pretty good. Because my spreadsheet has got great information. It's got book name, title, and my rating. And the rating is very helpful for it to calibrate what I'm likely to enjoy reading.Link

LubaWhat are the three books that changed your life?Link

AnkurThis is a tough one off the top of my head. So one, when I was... Yeah, yeah. Ah, that looks intense.Link

LubaYeah, it looks intense. We can film the workout a little bit. Oh, this is Tone House. It's really intense. Have you been to Tone House? It's like CrossFit on steroids. Yeah, yeah. And that guy, his name is James. Yeah. He's aggressive. Yeah, it's good though. It's fun, but really aggro. Okay, so, three books that changed your life?Link

AnkurThree books. Okay. We can start chronologically. I remember being like 13 or 14, reading a book called *Losing My Virginity*, which was...Link

LubaLiterally?Link

AnkurNo, no, no. Branson.Link

LubaYeah, it's really great.Link

AnkurAnd I remember that was the first time I was like, man, it'd be nice to build a company, because he looks like someone that's just having a blast, right? It was less about optimization. It was just kind of doing it for the love of the game. Yeah.Link

LubaOkay, I'm just going to pause here. So I love Richard Branson. I also read... It didn't ring a bell immediately, but I read *Losing My Virginity* and another book of his, which I totally am not remembering. And I was like, wow, he's the type of entrepreneur that I want to look up to and I want to be, because he seems so balanced, in the way that he had a family, he had a company, he had multiple companies. And as you said, he had so much fun. And I think we need more examples like that, that are like, I'm just having a blast. I'm playing a game. I'm a kid on the playground. Do you feel like company building has to be pain and suffering, or can you do this through...Link

AnkurI think that's the only way to make it sustainable, is to do it in a way where you look like you're having fun.Link

LubaLook like you're having fun, or like you're actually having fun?Link

AnkurWell, actually having fun. But looking like you're having fun is important. I think a lot of times startup founders get bad raps, and I was actually looking at this. I was like, why are some startup billionaire founders liked, and why are others disliked? And how much you look like you're having fun, I think, is how people kind of judge how likable you are. That's my hot take.Link

Like, think about it. There's a lot of Silicon Valley rich people that are honestly disliked. But the people that are liked, like the rappers and celebrities, and even, like, Richard Branson is a great example. He's pretty silly. Yeah. They're silly. They're goofballs. They're always just having a good time. Yeah. Even like, yeah, Larry Ellison.Link

LubaGreat examples. Who were your role models when it comes to entrepreneurs? Like, whom did you want to imitate?Link

AnkurIt's tough, because I don't have the traditional...Link

LubaLike, "Here's my idol."Link

AnkurYeah, here's my idol. I think everyone sort of has their pros and cons or whatever. I will say, different but related question: the person I'd most like to be friends with is The Weeknd.Link

LubaOh. That's interesting. Why?Link

AnkurI became the biggest Weeknd fanboy back in 2015 or something. Like, I just...Link

LubaThe Weeknd is a little darker.Link

AnkurYeah. I just put this out there. Hopefully one day someone will...Link

LubaThe Weeknd, if you're listening, Ankur wants to connect with you. Okay. Let's move on to book number two.Link

AnkurSo this isn't even about the specific book, but I remember... So I read a lot growing up. And then there were dark years, 4 or 5 years, where I didn't really read much at all.Link

LubaAnd then you were building?Link

AnkurNo. Not even. It was, like, from college to my mid-20s. I barely read a book. I just went through kind of a period where I fell out of love with reading. But then, I don't remember which book I picked up first, but I first started with a Murakami stage. Then I slowly went through every other Japanese fiction author or whatever.Link

But that was just an important time, because it reminded me how to love reading again, in a way that you're reading for the joy of it, and not because someone on Twitter said this is a business book you have to read or whatever. And basically since then, for the last ten years, reading has become an activity I do almost every night. Almost always fiction, just for enjoyment. Not trying to optimize anything.Link

LubaWhat's in it for you? Like, why are you reading? Are you transported into a different world?Link

AnkurIt's a different world. It helps kind of reset. Like, imagine you're working all day. How do you sort of switch that off? Reading is the perfect off switch for me. Yeah, I just feel like it's the closest you have to being able to experience what it's like to live multiple lives.Link

LubaYeah. I was recently talking to my mom about national identity, and she doesn't have a strong sense of national identity. Like, I never grew up with my mom being like, "I'm proud to be Belarusian." And I was like, yeah, why is that? And she's like, "Well, I loved reading as a kid, and every time I read something about Spain, I was like, I am a ballerina in Spain. Or if I read something about France, I was a French person." And I was like, huh, that's so interesting.Link

AnkurAnd it's also, like, different books for different time periods in your life. Like, I remember I read a lot of Bukowski after a breakup, and it was very helpful at the time. And, yeah, it just transports you to a different place. Yeah.Link

LubaSo do you have two other books that you would say were life-changing, or nothing really comes to mind? Okay, okay. What's your advice for someone who's still looking for their thing?Link

AnkurTry a lot of stuff. Like, honestly, the more you can maximize your surface area, the better it is going to be. How do you maximize your surface area? Like, live in a big city, meet a lot of people, try a lot of different things. Just, the more collisions you can possibly have, the more likely you are to get lucky.Link

LubaGreat advice, Ankur. Thank you so much for your time.Link

AnkurYeah. Thanks. It's fun.Link