The Exchanges, every show

Q Yeah, I totally get that. When we go back to the alleys and the micro ones for the fundraise, What do you advise founders when they get multiple term sheets and the heat is on?

A There's kind of two groups of firms. There's like the kingmaker firms that you should accept at any price. Um, one example would be Founders Fund or Sequoia, uh, or people like that. Um, and so if you get an offer from them at X and the offer from, um, someone else is at two X, you should take their offer because even if you're maximizing, um, amount raised and minimizing dilution, in the long run, Um, it, it, you're king made, and it will save you in the next round. Um, so you should definitely go for, but the, the, another mistake these entrepreneurs make is they have the list of the kingmaker firms as too big. Um, there, there's probably like some tier two firm that think very highly of themselves that aren't in that same level as, as Founders Fund or Sequoia.

AI assessment note: “There's like the kingmaker firms that you should accept at any price.”

Q A-C-C-Z fund. For more details, please see A-C-C-Z dot com slash disclosures. I am so excited for this conversation today. I've been seeing you post on Twitter. I've been seeing news articles everywhere about what DoNotPay has been experimenting with. And so we'll get into some of those timely topics, but first let's start out with where DoNotPay originated. So how did DoNotPay start and what really inspired this company?

A So it's no secret that I'm a terrible driver. And when I started driving at age 18, I got about 30 parking tickets between the ages of 20, um, in London and also when I moved here to study in college. And I couldn't afford to pay these really expensive tickets. And I learned something remarkable, which is if you know the right things to say, you can save a lot of money. And, um, I got this reputation among my family and friends as the person who can help with parking tickets. And it wasn't long before people were just messaging me, just pictures of their tickets. They wouldn't even say anything. I didn't want to copy and paste all of these documents. And so I thought, why not build an automated solution with templates where a user can select an option and then a defense is generated and sent to the right place. And I really just did it for a few family and friends, and I never could have imagined that it would go globally viral because people hate parking tickets. And that's what made me realize that the idea of helping people with technology and consumer rights is bigger than just tickets. And so I spent the past almost seven years now expanding Do Not Pay from parking tickets to many other areas of the law.

AI assessment note: “when I started driving at age 18, I got about 30 parking tickets”

Q So tell me a little bit more about that particular use case where you are helping someone get a refund or get access to something where it typically would take hours of someone sitting on the phone. How are you actually facilitating that with technology?

A So our motto is the squeaky wheel gets the grease. So if you are on a flight and the in-flight wifi doesn't work and you've paid, it's now 50 dollars for transcontinental in-flight wifi and it doesn't work. Our software will generate a letter and send it off to United Airlines, and it will cite FTC statutes and be really aggressive. United will receive that letter and think it's not worth it. And so, 80% plus of the time, they just grant the refund. And that's what's amazing is just with a template letter, we've managed to achieve all of this success over the past few years. But what's really exciting is in the past kind of six months, we're actually using more and more true AI. Versus decision tree templates.

AI assessment note: “Our software will generate a letter and send it off to United Airlines”

Q Do you think chat interface is the right UI for the future of consumer AI?

A It's good in some areas, terrible in others. I think for the travel use case, it's terrible. There's a big debate on X going on about this right now. Um, the reason it works for us is you're taking kind of unstructured responses and making them structured. So, um, when I started Do Not Pay, I did a Freedom of Information Act request in the UK for the top 12 reasons why parking tickets are cancelled. Poor signage, um, the parking bay being legally too small, all of the reasons. And the problem, the reason I did a chatbot is the consumers had no idea which reason to pick, and they'd, and they'd, um, pick the wrong reason, or they just wouldn't select what, what was the best thing to pick. But, so when I did chat, they could write whatever gibberish they wanted, and it would match them to the correct defense. And that was really the, the unlock of do not pay.

AI assessment note: “It's good in some areas, terrible in others.”

Q Are you able to predict the ones that will be hot versus not?

A No, the, the opposite is true, actually. The, the crazier it is, um, the, um, the better they do. Um, so Ali Ansari is a micro one, is objectively my best performing investment in terms of multiple. The founders get upset when I reveal exact valuation numbers, but let's say over a thousand X, well over a thousand X, um, and based on the kind of the scale of the business. Um, and When I met him, he, um, I said, I'll invest only on three conditions. So as a California LLC, Uninvestable, it has to be Delaware C Corp. Um, he was based in kind of Los Angeles as a solo founder. Um, and he was running a kind of a staffing business, um, which there's a million staffing companies, even in the UK. And so I said, you have to move to the Bay Area. You can live in my spare bedroom. Um, You can, um, you have to reincorporate in Delaware or shift to Delaware. Um, and, um, you have to use, do a software style product. I don't mind what you do, but it can be anything. And we grinded and he's the hardest, one of the hardest working people I've ever seen. Um, and actually, um, he still lives in my building to this day. And I like come at 12 AM and he's like working like, um, middle of the night. And he did all those three things and it changed everything.

AI assessment note: “No, the, the opposite is true, actually. The, the crazier it is”

Q It is the shittest question, um, which I've often been asked, but actually I've found there's more and more nuance to it, and Dak should, Greptile told me I should ask this. He said, you back founders that others maybe wouldn't when you actually look at them in that instance. What is it that you look for that is non-obvious or atypical in the founders that you do invest in?

A So, the number one thing I look for is a deep connection to the problem that they won't give up. So, I, I go back to my own journey. I'm Mr. Do Not Pay. Um, I'm the type of person to get 10 parking tickets just to test out the service or wait on hold for hours to save 20 pounds or dollars, I guess. Um, and I look for those founders with, with a really deep connection to the problem. So, for example, I was in the very, very first pre-precede of a company called Owner.com with Adam Guild, and He built the initial version of his product to help his mother's dog grooming business. And so many of these founders come up with these BS stories, but, um, that is a real story and he really did it to help his mother. And similarly with me, I really did it because I hate the government with parking tickets. And so I look for that sort of founder market fit where they're, they're their own first customer. And I joke, if you're building for yourself, at least you have one customer.

AI assessment note: “the number one thing I look for is a deep connection to the problem”

Q Going back to the core ingredient of success and venture that the founders themselves, you, you're a dropout. Um, how do you think about the value of university today? And if you were sitting with, you know, a university student today, advising them on whether it's worth staying or worth pursuing a dream?

A People see their life as paint by numbers. So they say, if I go graduate, I go to business school, I go work at X company, then in five years I'll be ready to start my company. The problem is the world changes so quickly that the paint by numbers approach doesn't work anymore. And so I would say to any founder who has an idea of what they want to do, they should just go for it, and the world won't wait for them. Um, on the other hand, you see a lot of people drop out just for the sake of it. In fact, um, When I, when I dropped out, um, in 2018, I actually had like one or two classes left at Stanford. So I was very close. Um, it was very kind of taboo to drop out. Um, now dropping out is almost the establishment. So you see people drop out just for the sake of it. And I think that's definitely wrong, um, because there are huge advantages to, to being in college. Um, even if you're doing a startup, like you can recruit your friends, um, you have your college email and people will, um, Take you more seriously if you email them from Stanford or MIT.edu. Um, also people give college students more of a free pass. Um, if all of these founders who are getting this controversial stuff are in college, they, they might, they might be able to kind of pivot more quickly.

AI assessment note: “I would say to any founder who has an idea of what they want”

Q Do you think chat interface is the right UI for the future of consumer AI?

A It's good in some areas, terrible in others. I think for the travel use case, it's terrible. There's a big debate on X going on about this right now. Um, the reason it works for us is you're taking kind of unstructured responses and making them structured. So, um, when I started Do Not Pay, I did a Freedom of Information Act request in the UK for the top 12 reasons why parking tickets are cancelled. Poor signage, um, the parking bay being legally too small, all of the reasons. And the problem, the reason I did a chatbot is the consumers had no idea which reason to pick, and they'd, and they'd, um, pick the wrong reason, or they just wouldn't select what, what was the best thing to pick. But, so when I did chat, they could write whatever gibberish they wanted, and it would match them to the correct defense. And that was really the, the unlock of do not pay.

AI assessment note: “It's good in some areas, terrible in others.”

Q to call out a few and get you to quickly explain what this is, how it works, because I think many people are maybe familiar with DoNotPay's parking ticket support, things like crafting a cease and desist letter, but let me just give you a few examples that I was surprised by. So one of them that I saw on your website Is free raffle tickets. What does that mean?

A So there's this obscure law in America that says that, um, you can enter any competition for free. So you hear on the radio, you can pay to enter, but they always bury in the terms of service that if you mail an obscure letter to an obscure address, you can enter for free. So we've built a product that automates free entry into any competition. So you just paste in the terms of service, or you can even just choose from Competitions that our bot scrapes on websites and it enters it for you for free. And this is the thing with do not pay. There are so many laws that help consumers that no one has the time to actually follow through with, and that's a great job for technology.

AI assessment note: “we've built a product that automates free entry into any competition.”

Q necessary and crafting them almost like a template. And then a third generation, which is using AI, which is not just a template, but really bringing in all of the prior examples for a Particular letter and crafting something net new. How do you think about which use cases require step one, step two, or step three, or how are you assessing where to apply some of these new technologies?

A So we started at step two. And so what we did was we said, well, all of these letters that you had to pay a lawyer 300 dollars for, we're going to automate with document automation, which is a very simple technology, but it's something that hadn't been done for these types of letters we were doing. What's really exciting about step three is that sometimes the companies respond and the governments respond and step three with AI allows us to respond back instantly. So instead of helping someone with a hundred dollar dispute with Comcast, we can now work on 10,000 dollar medical bills because Comcast or United might let that hundred dollars go, but no hospital is just going to let 10,000 dollars go just because of one letter. And so you really have to have that conversation back and forth. And so what we're working on now is actually communicating life, um, on medical bills specifically, and I can go into the laws we're using around that. That will be kind of our first major AI product, um, in Do Not Pay.

AI assessment note: “instead of helping someone with a hundred dollar dispute... we can now work on 10,000 dollar medical bills”

Q Something that OpenAI has also done, though, is had humans as part of the training process to really hone it in. Are you also doing that? Are you bringing in lawyers who are specialized in these areas to take a look at the output from your models to hone them in or improve them?

A Yeah, we have some of the best lawyers in the country helping us, like at Wilson Sonsini and other firms. The AI has been very problematic for us, so there's really two problems with it. The first is that it's dishonest. So with Comcast, for example, it says things like, I've had three internet outages in the past 24 hours, and that might be a good way of getting a refund from Comcast, but it's not true, and it can cause liability issues. And in court, if you lie, that's a crime, and it could send people to jail. The second issue is that it talks too much. With Comcast, or even in a courtroom, there are some questions and human speech that don't require a response. It's like a rhetorical question. So imagine the judge says something like, um, hold on, let me take a look at the case. Uh, AI models would often say, okay, thank you. And by the way, I'm innocent for like these six reasons. The judge will just get annoyed. You have to build other AIs to decide whether to say something, let alone what to say. And so you have to really retrain it and also build these guardrails. Otherwise things get out of control.

AI assessment note: “we have some of the best lawyers in the country helping us, like at Wilson Sonsini”

Q That's, that's a good perspective. I think another amazing thing that I've seen, the technology can be cross-border as well. So Typically, a lawyer is specialized in one very particular area, maybe in one jurisdiction. Can you tell me a little bit more about how you're thinking about the potential for this technology to support people, not just in your region, but really anywhere?

A Yeah, the benefit of AI is it can read 10,000 documents and produce an answer in seconds, and not even the best human lawyer can do that. So I think the example you're talking about is a consumer rights issue relating to a timeshare. We had a elderly consumer in Boston. They got suckered into a timeshare actually in Mexico and do not pay got them out of it because there's a five day law in Mexico to cancel timeshare contracts. And so things like that, where you can help consumers in Boston, uh, for issues in Mexico, most lawyers in Boston don't know about Mexican law, but AI does because you can just feed it all the timeshare cases and it comes out with a way out. And the same is true actually for Comcast. These generic AI models like, um, DaVinci from OpenAI, they're, they're not actually that good at the law. What we've had to do at DoNotPay is you feed it documents. So we say, we feed, fed it all of these outcomes from the templates in many years of operating. And you say, based on these thousand documents, write X. And then it becomes much better than just a generic usage of any of the models.

AI assessment note: “things like that, where you can help consumers in Boston, uh, for issues in Mexico”

Q Why is it that you place such a bet and conviction on very young founders so much earlier than maybe others would?

A So I think young founders have no option but to succeed. Um, if you back a Google engineer, um, the first thing they'll do is they'll hire 10 of their friends, and it's like this endless, like, scheme of hiring. Um, the first thing a young founder will do is they'll build the product, and they don't have anything to fall back on. Especially if they have a chip on their shoulder, they, they really, the only thing they can do is succeed. And so I think the grit level with young founders is 10 X, and Being an entrepreneur is like eating glass. If you don't, like, um, have a true kind of dedication to win, uh, they'll, they'll give up at the first opportunity.

AI assessment note: “grit level with young founders is 10 X”

Q Browder Hotel, let's go. Um, along the way, you said, hey, um, you'll be worth hundreds of millions, blah, blah, blah. How do you advise founders on the ability to take secondaries off the table early? We're seeing it more and more earlier and earlier. How do you advise them?

A I think that the people buying these secondaries are sharks. If, if someone, if someone, um, is emailing you asking to buy Anthropix shares, they, the value of Anthropix is probably going to go up. And the same is true with these founders. And so I would say to them, um, if you're being bombarded with secondary offers, perhaps they have more experience with the market than even you do as a founder of your own business. And so I think a lot of founders, they've regretted, a lot of my friends, they've regretted taking secondaries. Um, because they've got one of these Kingmaker firms in, and then the valuation has gone up three X in a few weeks. So why not do the secondary at the higher price? Um, so I would say if it's too much inbound, um, there could be something that they have within their investing experience that as a founder, maybe it's their first time business. They maybe shouldn't jump to, to sell too quickly.

AI assessment note: “They maybe shouldn't jump to, to sell too quickly.”

Q It is the shittest question, um, which I've often been asked, but actually I've found there's more and more nuance to it, and Dak should, Greptile told me I should ask this. He said, you back founders that others maybe wouldn't when you actually look at them in that instance. What is it that you look for that is non-obvious or atypical in the founders that you do invest in?

A So, the number one thing I look for is a deep connection to the problem that they won't give up. So, I, I go back to my own journey. I'm Mr. Do Not Pay. Um, I'm the type of person to get 10 parking tickets just to test out the service or wait on hold for hours to save 20 pounds or dollars, I guess. Um, and I look for those founders with, with a really deep connection to the problem. So, for example, I was in the very, very first pre-precede of a company called Owner.com with Adam Guild, and He built the initial version of his product to help his mother's dog grooming business. And so many of these founders come up with these BS stories, but, um, that is a real story and he really did it to help his mother. And similarly with me, I really did it because I hate the government with parking tickets. And so I look for that sort of founder market fit where they're, they're their own first customer. And I joke, if you're building for yourself, at least you have one customer.

AI assessment note: “the number one thing I look for is a deep connection to the problem”

Q Yeah, I totally get that. When we go back to the alleys and the micro ones for the fundraise, What do you advise founders when they get multiple term sheets and the heat is on?

A There's kind of two groups of firms. There's like the kingmaker firms that you should accept at any price. Um, one example would be Founders Fund or Sequoia, uh, or people like that. Um, and so if you get an offer from them at X and the offer from, um, someone else is at two X, you should take their offer because even if you're maximizing, um, amount raised and minimizing dilution, in the long run, Um, it, it, you're king made, and it will save you in the next round. Um, so you should definitely go for, but the, the, another mistake these entrepreneurs make is they have the list of the kingmaker firms as too big. Um, there, there's probably like some tier two firm that think very highly of themselves that aren't in that same level as, as Founders Fund or Sequoia.

AI assessment note: “There's like the kingmaker firms that you should accept at any price.”

Q Going back to the core ingredient of success and venture that the founders themselves, you, you're a dropout. Um, how do you think about the value of university today? And if you were sitting with, you know, a university student today, advising them on whether it's worth staying or worth pursuing a dream?

A People see their life as paint by numbers. So they say, if I go graduate, I go to business school, I go work at X company, then in five years I'll be ready to start my company. The problem is the world changes so quickly that the paint by numbers approach doesn't work anymore. And so I would say to any founder who has an idea of what they want to do, they should just go for it, and the world won't wait for them. Um, on the other hand, you see a lot of people drop out just for the sake of it. In fact, um, When I, when I dropped out, um, in 2018, I actually had like one or two classes left at Stanford. So I was very close. Um, it was very kind of taboo to drop out. Um, now dropping out is almost the establishment. So you see people drop out just for the sake of it. And I think that's definitely wrong, um, because there are huge advantages to, to being in college. Um, even if you're doing a startup, like you can recruit your friends, um, you have your college email and people will, um, Take you more seriously if you email them from Stanford or MIT.edu. Um, also people give college students more of a free pass. Um, if all of these founders who are getting this controversial stuff are in college, they, they might, they might be able to kind of pivot more quickly.

AI assessment note: “there are huge advantages to, to being in college.”

Q Dude. What did you see in him? I, I don't mean that rudely to Ali, he's, I've seen actually interviews, he's clearly brilliant now, but you learn and develop. Staffing business, how, I'm sorry to be rude, how uninteresting, as you said, there's millions of them living in, what did you see in him that made you so convinced that he would pivot, change the company location, change his location?

A Never give up. Um, if you back someone who's above average IQ, very smart, um, and never give up, of course they'll succeed. And I think this is actually a mistake a lot of VCs are making. They are focusing too much on, on these credentials. So there's a race right now to back the math Olympiads. Um, VCs are like going to spelling bees and math competitions in high school. And I think IQ is very important. You need someone smart, but Much more important is they'll never give up. And I could tell from my own journey and interviewing people for the Teal Fellowship and seeing so many founders that Ali was someone who has never give up. And he's, he's, um, overcome huge challenges along the way to kind of build his business.

AI assessment note: “Ali was someone who has never give up.”

Q VCs are sharks. I love that. Um, it's a good title. Um, what other ways do you advise founders to just be mindful of a shark-like mentality towards VCs or from VCs?

A So I say to the young founders, the VCs will say anything to get you to sign right there and then. Anything. They'll say, I, they, so they'll reverse engineer what the founder is looking for and say, oh, I'm friends. I'm buddies with that, uh, guy. Um, I know someone at that company with golf buddies. I can get him to be a customer. Like right now I can introduce you to so many customers. And they just say exactly what the founders want to hear. And these poor young founders, they're so impressionable. Sometimes they sign the safe on the spot. And afterwards, of course, it never materializes. They never get that, ah, customer that they were wanting because it turns out they weren't as close golf buddies as the person made it out. So I say to founders, do not sign on the spot. And going back to my offers, I don't make them sign on the spot. It's just too much, especially for these young founders. I say, you have the night to think about it. I think decisiveness is a key quality. So I do want to know by the next morning, if not, it's done. But they can't sign on the spot.

AI assessment note: “So I say to founders, do not sign on the spot.”

Q there. I'm seeing more and more funds, uh, founders, sorry, who are like, oh, I'm being very dilution sensitive with this round, and it's often very early rounds, and they'll do five percent, maybe 10% dilution on a seed round or a pre-seed round, where it used to be 1520. That's hard for me as a fund. What do you advise founders on dilution sensitivity from your lessons and observations?

A I think it's, it's nonsense. I think, um, they shouldn't do something stupid, like sell their company to, sell 50% of their company to a Midwest angel for like a hundred K like you see with some of these shark tank deals. But at the same time, the number one thing I say to, especially these young founders I back is either it succeeds or it doesn't. If it succeeds, at a minimum, you're worth hundreds of millions or billions. Um, you're on the cover of magazines. It's life changing. If it fails, you're nothing. So it's best to if, if,, if taking that extra money can reduce the chance of failure by even five percent, the kind of expected value is infinity in terms of life improvement. Five percent of infinity, you should still do it.

AI assessment note: “I think it's, it's nonsense.”

Q Has Trump been better for business for you?

A Absolutely. I, I think that whether you agree or disagree with what's going on right now, um, it's objective that for tech, um, the current administration is a lot better. Um, Lena Kahn in my view is, is evil. Um, several companies I invested in had the acquisitions blocked by, by the kind of Lena Kahn style approach. Um, and The, the worst kind of Lina Khan story I heard is there's like a biotech company that, um, was being acquired by a much larger kind of pharmaceutical company, and Lina Khan's FTC blocked the acquisition, and to this day, and the drug didn't get developed, and to this day, 50 people die a year because, because of the acquisition being blocked. So I actually think that, um, the, the kind of tech policies of the last administration were not very good.

AI assessment note: “Absolutely. I, I think that whether you agree or disagree”

Q Why is it that you place such a bet and conviction on very young founders so much earlier than maybe others would?

A So I think young founders have no option but to succeed. Um, if you back a Google engineer, um, the first thing they'll do is they'll hire 10 of their friends, and it's like this endless, like, scheme of hiring. Um, the first thing a young founder will do is they'll build the product, and they don't have anything to fall back on. Especially if they have a chip on their shoulder, they, they really, the only thing they can do is succeed. And so I think the grit level with young founders is 10 X, and Being an entrepreneur is like eating glass. If you don't, like, um, have a true kind of dedication to win, uh, they'll, they'll give up at the first opportunity.

AI assessment note: “I think young founders have no option but to succeed.”

Q Browder Hotel, let's go. Um, along the way, you said, hey, um, you'll be worth hundreds of millions, blah, blah, blah. How do you advise founders on the ability to take secondaries off the table early? We're seeing it more and more earlier and earlier. How do you advise them?

A I think that the people buying these secondaries are sharks. If, if someone, if someone, um, is emailing you asking to buy Anthropix shares, they, the value of Anthropix is probably going to go up. And the same is true with these founders. And so I would say to them, um, if you're being bombarded with secondary offers, perhaps they have more experience with the market than even you do as a founder of your own business. And so I think a lot of founders, they've regretted, a lot of my friends, they've regretted taking secondaries. Um, because they've got one of these Kingmaker firms in, and then the valuation has gone up three X in a few weeks. So why not do the secondary at the higher price? Um, so I would say if it's too much inbound, um, there could be something that they have within their investing experience that as a founder, maybe it's their first time business. They maybe shouldn't jump to, to sell too quickly.

AI assessment note: “They maybe shouldn't jump to, to sell too quickly.”

Q Do you worry about the susceptibility of founders when they're that young? Like, bluntly, I see a lot of very young founders now getting so caught up in the fundraising game that it's like, it's almost a game of, I raised a round and from who? And it's like, we're building a business to create a product for customers. Let's not forget why we're here. Do you worry about that?

A Yes, so I escaped the UK to go to Stanford, and there was a, um, Stanford Review article, which is a student publication, and the publication said, It's easier for a Stanford student to get into YC than it is for them to get a job now. And so we've seen a rise of, um, I would say fake founders where they don't have that connection to their problem and they're just starting something just because it's cool or because they have nothing to do for the summer. And actually being an investor, you have to be very careful about backing students over the summer because part of the signal is they've dropped out and they're going all in on this, but of course during the summer you can't actually tell if they've dropped out. So Um, I'm actually, it's scaled back a bit during the summer, not because I'm in Capri like all the other VCs, but because you have to worry about these fake founders.

AI assessment note: “we've seen a rise of, um, I would say fake founders”

Q Dude. What did you see in him? I, I don't mean that rudely to Ali, he's, I've seen actually interviews, he's clearly brilliant now, but you learn and develop. Staffing business, how, I'm sorry to be rude, how uninteresting, as you said, there's millions of them living in, what did you see in him that made you so convinced that he would pivot, change the company location, change his location?

A Never give up. Um, if you back someone who's above average IQ, very smart, um, and never give up, of course they'll succeed. And I think this is actually a mistake a lot of VCs are making. They are focusing too much on, on these credentials. So there's a race right now to back the math Olympiads. Um, VCs are like going to spelling bees and math competitions in high school. And I think IQ is very important. You need someone smart, but Much more important is they'll never give up. And I could tell from my own journey and interviewing people for the Teal Fellowship and seeing so many founders that Ali was someone who has never give up. And he's, he's, um, overcome huge challenges along the way to kind of build his business.

AI assessment note: “Ali was someone who has never give up.”

Q there. I'm seeing more and more funds, uh, founders, sorry, who are like, oh, I'm being very dilution sensitive with this round, and it's often very early rounds, and they'll do five percent, maybe 10% dilution on a seed round or a pre-seed round, where it used to be 1520. That's hard for me as a fund. What do you advise founders on dilution sensitivity from your lessons and observations?

A I think it's, it's nonsense. I think, um, they shouldn't do something stupid, like sell their company to, sell 50% of their company to a Midwest angel for like a hundred K like you see with some of these shark tank deals. But at the same time, the number one thing I say to, especially these young founders I back is either it succeeds or it doesn't. If it succeeds, at a minimum, you're worth hundreds of millions or billions. Um, you're on the cover of magazines. It's life changing. If it fails, you're nothing. So it's best to if, if,, if taking that extra money can reduce the chance of failure by even five percent, the kind of expected value is infinity in terms of life improvement. Five percent of infinity, you should still do it.

AI assessment note: “I think it's, it's nonsense. I think, um, they shouldn't do something stupid”

Q VCs are sharks. I love that. Um, it's a good title. Um, what other ways do you advise founders to just be mindful of a shark-like mentality towards VCs or from VCs?

A So I say to the young founders, the VCs will say anything to get you to sign right there and then. Anything. They'll say, I, they, so they'll reverse engineer what the founder is looking for and say, oh, I'm friends. I'm buddies with that, uh, guy. Um, I know someone at that company with golf buddies. I can get him to be a customer. Like right now I can introduce you to so many customers. And they just say exactly what the founders want to hear. And these poor young founders, they're so impressionable. Sometimes they sign the safe on the spot. And afterwards, of course, it never materializes. They never get that, ah, customer that they were wanting because it turns out they weren't as close golf buddies as the person made it out. So I say to founders, do not sign on the spot. And going back to my offers, I don't make them sign on the spot. It's just too much, especially for these young founders. I say, you have the night to think about it. I think decisiveness is a key quality. So I do want to know by the next morning, if not, it's done. But they can't sign on the spot.

AI assessment note: “So I say to founders, do not sign on the spot.”

Q Has Trump been better for business for you?

A Absolutely. I, I think that whether you agree or disagree with what's going on right now, um, it's objective that for tech, um, the current administration is a lot better. Um, Lena Kahn in my view is, is evil. Um, several companies I invested in had the acquisitions blocked by, by the kind of Lena Kahn style approach. Um, and The, the worst kind of Lina Khan story I heard is there's like a biotech company that, um, was being acquired by a much larger kind of pharmaceutical company, and Lina Khan's FTC blocked the acquisition, and to this day, and the drug didn't get developed, and to this day, 50 people die a year because, because of the acquisition being blocked. So I actually think that, um, the, the kind of tech policies of the last administration were not very good.

AI assessment note: “Absolutely. I, I think that whether you agree or disagree”

Q to call out a few and get you to quickly explain what this is, how it works, because I think many people are maybe familiar with DoNotPay's parking ticket support, things like crafting a cease and desist letter, but let me just give you a few examples that I was surprised by. So one of them that I saw on your website Is free raffle tickets. What does that mean?

A So there's this obscure law in America that says that, um, you can enter any competition for free. So you hear on the radio, you can pay to enter, but they always bury in the terms of service that if you mail an obscure letter to an obscure address, you can enter for free. So we've built a product that automates free entry into any competition. So you just paste in the terms of service, or you can even just choose from Competitions that our bot scrapes on websites and it enters it for you for free. And this is the thing with do not pay. There are so many laws that help consumers that no one has the time to actually follow through with, and that's a great job for technology.

AI assessment note: “we've built a product that automates free entry into any competition.”

Q about how you're thinking about evolving the different services that you offer. I mean, you already offer, as I mentioned, a hundred things on your website. So how, how did you decide, for example, next up, Is medical bills. We're addressing that. Or how do you decide whether, oh, actually we want to go into the physical courtroom. Like what are you doing to understand where your priorities should be?

A We're just trying to create value for people. So we look very carefully about the average amount that a do not pay customer saves on a yearly basis. And we're trying to 10 X that. So instead of it being a few hundred dollars, we, a single medical bill could be 10,000 dollars. And that's where I think AI comes in really raising the value of the cases that the, Robot lawyer can pursue. We've tried things that haven't worked well because it's too emotional. AI is not too good at dealing with emotions. So many years ago, actually, before I turned do not pay into a business, I tried to use do not pay for asylum, like to automate the asylum process. But with these cases, sometimes people are crying in the courtroom, and that's something that software can never really touch because you need the human touch in those sorts of cases.

AI assessment note: “we look very carefully about the average amount that a do not pay customer saves”