Joshua Browder, DoNotPay | Saving Consumers $100M+ & Investing in Thiel Fellows

Molly O'Shea talks with Joshua Browder, Founder & CEO of DoNotPay, a $200M AI champion designed to help people fight against big corporations and beat bureaucracy. Joshua shares his journey from dropping out of Stanford for a Thiel Fellowship to founding DoNotPay. To date, DoNotPay has saved consumers $100M+ on over 1.6M cases and attracted significant venture capital interest. We go deeper into the innovative features of DoNotPay, its ‘spicy’ media strategy, and the importance of building a subscription-based business model. Browder also reflects on his experiences as a Thiel Fellow and his investment philosophy as “statistically” the most active Thiel Fellow investor. Our discussion concludes with his predictions for the future of the tech market and the potential for a new tech bubble. -- Follow on Twitter https://x.com/MollySOShea https://x.com/jbrowder1 -- Check out Do Not Pay https://donotpay.com/ -- Subscribe to Sourcery: https://www.sourcery.vc/ -- Sponsor: Archer Archer's Midnight is a piloted four passenger aircraft designed to perform rapid back-to-back flights with minimal charge time between flights. Learn more about how Archer is set to open up a new world of opportunity for passengers by providing safe and efficient access to people, places, and events across the communities they live, visit https://www.archer.com/ – COMPANIES MENTIONED: DoNotPay:https://donotpay.com Google:https://google.com Meta:https://meta.com Amazon:https://amazon.com Comcast:https://xfinity.com IBM Watson:https://www.ibm.com/watson Equifax:https://www.equifax.com Harper's Magazine:https://harpers.org McDonald's:https://www.mcdonalds.com Dropbox:https://www.dropbox.com Polymarket:https://polymarket.com Character AI:https://character.ai Riverside:https://riverside.fm Figma:https://www.figma.com Andreessen Horowitz:https://a16z.com Founders Fund:https://foundersfund.com Kotu Capital:https://www.kotucapital.com Index Ventures:https://www.indexventures.com Lux Capital:https://www.luxcapital.com Tribe Capital:https://tribecap.co Day One Ventures:https://www.dayoneventures.com DST Global:https://dst-global.com Owner.com:https://www.owner.com Wanda:https://www.wanda.co Robinhood:https://robinhood.com Umami Burger:https://umamiburger.com -- TIMESTAMPS: (00:00) Preview (01:03) DoNotPay: Fighting Big Corporations and Bureaucracy (02:13) A Modern-Day David vs. Goliath (03:33) AI and DoNotPay: Not Just Agents, But Robots (04:20) Scale and Impact: DoNotPay's Success Stories (05:17) Key Use Cases: Free Trial Credit Card and Robo Revenge (07:10) Unexpected Allies: Warren Buffett and IBM Watson (10:50) Media Strategy: Tapping into Anger and Current Events (12:40) Supreme Court Challenge: A Million Dollar Offer (14:55) Sponsor: Archer (15:39) Enemies and Good Media Strategy (17:05)) Business Model: Subscription, Profitability, and Dividends (21:40) Investor Relations: Favorable Relationships and Strategies (23:40) Thiel Fellowship: Investing in Young Entrepreneurs (29:40) The State of Entrepreneurship: Challenges and Opportunities (33:00) Leadership: Values and Influences (35:10) 2025 Predictions: Voice AI, Tech Bubble, and M&A (37:55) Wrap -- RECOMMENDED PODCAST: 🎙️ Unpack Pricing Dive into the dark arts of SaaS pricing with Metronome CEO Scott Woody and tech leaders. Learn how strategic pricing drives explosive revenue growth in today's biggest companies like Snowflake, Cockroach Labs, Dropbox and more. Apple: https://podcasts.apple.com/us/podcast/id1765716600 Spotify: https://open.spotify.com/show/38DK3W1Fq1xxQalhDSueFg

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Speaker 00

  The best consumer companies monetize and tap into core human emotions. So with Robinhood or Polymarket these days, it's greed. Dating apps, it's lust. Some apps are loneliness, maybe character AI is loneliness. But with Do Not Pay, it's really about anger. Statistically, I'm fortunate to be in the most Thiel Fellows out of anyone. Just before this interview, I was actually counting and I only got through to 2024 to 2019 and that already got me to 33. And then in the class of 2023, so last year, I was in 45% of the Fellows. So nine out of 20. I've deployed about 30 million just in Thiel Fellows alone. And also other great entrepreneurs.

• 0:44Speaker 00

  Having the Russia mafia after your family really puts everything into perspective. And so it taught me the value of courage and standing up for what you believe in and always never giving up.

• 1:03Molly O'Shea?

  Welcome to Sorcery. I'm your host, Molly O'Shea. Today, we have Joshua Browder, founder and CEO of Do Not Pay. Do Not Pay is an AI built to help fight big corporations, protect your privacy, find hidden money and beat bureaucracy. Joshua started Do Not Pay back in 2015 after dropping out of Stanford to pursue a Thiel Fellowship. Now, Do Not Pay has raised $23 million in total funding and is valued at over $200 million. Their cap table includes, honestly, every big name out there, including Andreessen Horowitz, Founders Fund, Co2, Index, Lux Capital, Tribe Capital, Day One Ventures, DST Global, The Chainsmokers and more.

• 1:46Molly O'Shea?

  Unlike some, if not most, SaaS companies, Do Not Pay is actually profitable and was one of the first VC-backed companies to issue dividends back to their investors. This is highly unconventional and very impressive. Joshua is a really fun person to learn from. I hope you enjoy. Do Not Pay's mission is quite strong. You've built software to fight big corporations and beat bureaucracy.

• 2:10Molly O'Shea?

  Kind of a big deal and a big task.

• 2:12Speaker 00

  Yeah, so I think of Do Not Pay as an AI version of David in David versus Goliath. It helps people in hundreds of different areas, fight big companies and governments. And the very first use case almost nine years ago was parking tickets. As you can tell from my accent, I'm originally from England. And when I moved to study at Stanford, I got a huge number of tickets. And I learned if you know the right things to say, you can actually save a lot of money with these tickets. And I just built Do Not Pay just to help a few friends. I never counted on one of those friends writing about her experience on Reddit. And it went on the front page and I went from about ten cases in the first week to fifty thousand cases. And it made me realize that this idea of helping people fight back is bigger than just tickets.

• 2:56Speaker 00

  And so fast forward to today and Do Not Pay has over two hundred different features that help people get refunds, negotiate their bills, cancel subscriptions, all of the areas where no one has time to fight back. And what's interesting is it started as a template company, but now there's literally like AI robots logging into people's Comcast accounts, chatting with Comcast to fight their bills. And Comcast is using AI and Do Not Pay is using AI, so sometimes even two AIs are negotiating against each other. So that's kind of a high level of what we do.

• 3:29Molly O'Shea?

  Would you equate this to like an AI agent?

• 3:32Speaker 00

  Yes, well, I don't, I don't like the word agent, uh, because it implies that the AI is connecting all the APIs. Really, the AI is just the language and we've actually manually built the connections with all of the different services. Interestingly, sometimes the AI has to fax documents, so it's like connecting with the Stone Ages, where it's faxing a document to, um, because that's actually a certain way to like make insurance claims and things like that. So an agent implies that the AI is literally faxing the document and actually we're connecting it to the API manually. I think agents have maybe a year to go before they can do it on their own.

• 4:12Molly O'Shea?

  Agents are very hype right now, so I love the explanation of breaking that down. Um, okay, so you've not only built this. Over the course of the last, you know, several years, but scaled it tremendously. You've saved an estimated $100 million for consumers. How many tickets does this equate to overturning? How many users is this in total?

• 4:33Speaker 00

  Yeah, so Do Not Pay has successfully completed, the last time I checked, over 1.6 million cases for people. And this can be anything from a $35 in-flight Wi-Fi refund to we've had users in exceptional cases get back tens of thousands of dollars in medical bills. Parking tickets now only make up about 3% to 4% of our usage. And I think with every business, the question is, why now? Why hasn't this succeeded before? And in Do Not Pay's case, the answer is unless you're a bad driver like me, the average person only gets a ticket once a year. And so I knew if I wanted to be successful, I had to actually build out all of these different use cases to get people to be a subscriber and continue to use the service.

• 5:17Molly O'Shea?

  What are like the typical use cases that you have? And what are some of the newer ones that you've been adding?

• 5:23Speaker 00

  The biggest one is refunds. A lot of companies, they say they're going to give you a refund and they never follow up. Our most popular product, though, is something called the Free Trial Credit Card. And it's a special credit card that you can use for any free trial. And it's not linked to you, it's not linked to your credit. And you can just give that card number. And when they try and charge you, the subscription doesn't go through. You can just press refresh. So we have some people who actually just cycle through unlimited free trials for different services. I shouldn't really be saying that, but people love it.

• 5:54Molly O'Shea?

  Have you had any wild card requests? Like, are there any crazy things that you've actually tried to go after that might have been too hard? Or that you actually were able to solve?

• 6:03Speaker 00

  My favorite product, it takes a little effort, but it's something called Robo Revenge. Robo Revenge allows users to get paid whenever they get a spam call. And there's an amazing law, it's called the Telephone Consumer Protection Act. And it allows people to get up to $1,500 every time they get a call. But the problem is these spam callers, they don't tell you who their real name is. They're using fake names. Names and fake numbers. And so the way this product works is it's a trap. So the spam callers call up our users and they try and sell them something. And our users say, I'm very interested. Here's a special credit card and do not pay gives them like a trap credit card.

• 6:45Speaker 00

  And when they try and charge the do not pay card, of course it declines, but it gets their business name, business address, business details, and it uses all of that to send a demand letter to get this money under the law. And we have some users who are making tens of thousands of dollars a year suing spam callers and getting revenge. And one user actually in New Jersey bought a new roof for his house through all the money he's making suing the spam callers. So I love it because it's like trapping the scammers.

• 7:14Molly O'Shea?

  You might be fighting big corporations, but I know you also have some allies within it. So who are some of your most unexpected allies that you've been partnered with?

• 7:23Speaker 00

  Well, I'll tell you two quick stories. The first was Warren Buffett's influence on the business. So I was fresh off the boat from the UK at Stanford and I was sitting in a computer science class one day. And I got an email and it says, do you want to have lunch and interview Warren Buffett on stage in Seattle for a conference? And I thought this was a spam email because I'd never dealt with these people. It was actually an email from Microsoft. So it's a Microsoft conference. But I phoned up the number at the bottom of the email and it turned out it was legit. And for some random process, maybe they didn't like parking tickets at Microsoft or something. They just decided to do this cold outreach and asked me to do the Warren Buffett interview.

• 8:04Speaker 00

  So I flew to Seattle and I was really nervous about this interview because Warren Buffett has been asked everything. And I want my biggest takeaway to be authentic and original. And I didn't want to ask something where you could just read in a book or see online or things like that. And so I was agonizing over the different questions to ask him, as I'm sure you can relate with your great podcast. And I decided the only way I could make it unique was to engage in some shameless self-promotion. And so one of the questions I asked him was, tell me about a time that you fought and stood up for your consumer rights and the fought for justice. Told a story where he hadn't actually told before anywhere and it was the first ever lawsuit that he was involved in when he was, I think, about twenty three.

• 8:48Speaker 00

  So truly back in the olden days, he was a subscriber to Harper's Magazine, which still exists today. And they kept sending him invoices. This was before the days of credit cards, so they would invoice you every month. And if you didn't pay the invoice, you'd get in trouble. And he tried to cancel a subscription, but they wouldn't cancel his subscription, no matter what he said. He wrote to them, he phoned them up. I think he even visited their offices and they kept sending him these invoices. And so he decided to sue Harper's Magazine in small claims court. He won, he represented himself and he won his lawsuit. And not only did they cancel, finally cancel his subscription, but he actually got some extra damages from the court.

• 9:27Speaker 00

  And that taught him a very valuable lesson, which is no matter how small the issue, you stand up for yourself. With me, I immediately had a realization, which is this was back, I don't know, I can't even do the math as to how long ago this was. But certainly before like nineteen seventy, maybe nineteen sixty or even earlier. And still in twenty twenty two, twenty twenty three, twenty twenty four, you still can't cancel your subscriptions. And that was what gave me the idea to actually build this free trial credit card. So that was a big learning. Another big learning was Do Not Pay probably got about ten million dollars of free advertising from IBM.

• 10:08Speaker 00

  Back when we first started, we had some text to speech and speech to text in our products. And at the time, actually, it's not the case now, but the only best API to use was actually the IBM Watson Speech to Text API. And they were so excited that someone finally found a use case for Watson. They blasted it on like billboards in Times Square, full page ads in the New York Times and Wall Street Journal. And that also got us a lot of users. So I hate big, big companies and like, but I think there are some times where your interests can align and you can ride on their coattails.

• 10:41Molly O'Shea?

  That's an amazing story with Warren Buffett. Going on to something really fun. So Do Not Pay has quite the spicy.

• 10:50Molly O'Shea?

  Media strategy. It's like super fun and it's like righteous and it's for the people and all of that. So how did you come across the strategy and how would you actually frame this out?

• 11:01Speaker 00

  I learned this by accident when people were so angry at parking tickets that we got all of those users on Reddit. But I think the best consumer companies monetize and tap into core human emotions. So with Robinhood or Polymarket these days, it's greed, dating apps, it's lust, some apps are loneliness, maybe character AI is loneliness. But we do not pay. It's really about anger. And so my initial media strategy at the beginning was to find the things that people are really angry about and build solutions for them and then tap into current events. And so, for example, in 2018, 2019, Equifax, the credit bureau leaked hundreds of millions of people's data.

• 11:43Speaker 00

  And I thought, wouldn't it be great to build a product to fight back against Equifax? And so we had a huge media launch around that. Even during COVID, we were really paying attention to the different problems and benefits and angry things that people were experiencing and making sure to tap into that. And every few months, the best thing about tapping into anger is people are always angry at something new. And that's what we've continued to do. And because of that, we've been very successful. We've been on The Daily Show. The Daily Show is like not typically a news program. It's a comedy segment and they don't really promote startups. But there was a whole segment about me with a bat hitting a robot lawyer. So things like that, where you tap into people's emotions can really like separate you from the noise.

• 12:28Speaker 00

  Because especially now, we live in such a noisy world, you have to do something to kind of stand out.

• 12:34Molly O'Shea?

  Do you have any other cameos coming up? Are you gonna go on more podcasts? Are you gonna go on SNL?

• 12:39Speaker 00

  This is, this is the biggest thing. The Sorcery Podcast.

• 12:44Molly O'Shea?

  Correct answer. Thank you. So, within the media strategy, one of the spiciest things that you've also done is you offered a million dollars to anyone willing to use your AI to fight their case in the Supreme Court. This created a lot of buzz for the brand. So what was going through your head during this media storm? And how did this play out?

• 13:07Speaker 00

  So, I learned this lesson almost nine years ago, when I was pitching for the pre-seed for Do Not Pay, and I was pitching all of the blue chip Silicon Valley firms. This was at, so I was, my initial ask for the pre-seed was 500K. And these days, a scout of a scout could probably write a 500K cheque. But back in those days, the olden days, like 2015, 2016, even asking for 5K, you would pitch the entire partnership. Even like the luminaries, they would all be in the room. And so I walked into this pitch, and there were like, with the partners and then other people there, maybe 18 people in the room.

• 13:48Speaker 00

  And I started pitching, and I was really excited to talk about users and growth and things like that. And an argument broke out in the room. And I really didn't think the pitch went well, because the partners started arguing with each other and arguing with me over whether it's a good thing or a bad thing for society that robot lawyers can just generate lots of paperwork, and whether society would collapse with all this litigation and things like that. And I thought the pitch went really, really badly because of this argument. And I was kind of depressed. But I was speaking to the partner who brought me in that evening, and he said, no, that, this is great. Whenever there's this big controversy about whether it's good or bad for society, that means it's a winning company. So you probably got the deal. I'll let you know tomorrow. And so, fast forward nine years,

• 14:33Speaker 00

  and I really wanted to push the needle about AI and law. And I think there was nothing more controversial than offering to pay a lawyer a million dollars to use our AI in the Supreme Court. Sure enough, it did create a huge controversy, but at the same time, it created a lot of marketing for us. It created a lot of enemies, but I still think it was a big net positive.

• 14:55Molly O'Shea?

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• 15:38Molly O'Shea?

  Do you think enemies are good for a media strategy?

• 15:41Speaker 00

  I think the right type of enemies, you want a kind of consistent buzz, but not someone who's obsessed about you trying to take you out. Another enemy that I'm very lucky to have is actually David Duke, the head of the Ku Klux Klan. Early on, Do Not Pay, another thing we did is we provided free services for immigrants, like to get housing and things like that. And David Duke found out about this and he unleashed his Twitter mod. And so those are the right enemies to have because no one would take them seriously, but they kind of elevate the brand and it creates this good versus evil narrative.

• 16:17Molly O'Shea?

  That is wild. That is truly wild. Okay, so did anybody go to the Supreme Court? Like, where are we at?

• 16:23Speaker 00

  No, it turns out that lawyers make huge amounts of money arguing in the Supreme Court. And if they were to listen blindly to AI, they would probably lose their license. And so they probably lose a lot more than the $1 million they had to gain. With that said, though, I did get some interesting counteroffers. I got a state Supreme Court, someone offered, and that they were arguing a case. And there was also a former Solicitor General who is friends with one of the Supreme Court justices. And he offered to do a mock trial if we donated the money to charity. But I didn't want a state Supreme Court and I didn't want a fake case. I wanted a real case. So none of those two options were appealing, but it was interesting that it was close to happening.

• 17:05Molly O'Shea?

  Go into the business model of Do Not Pay. How has this evolved over time? And how does Do Not Pay make money?

• 17:13Speaker 00

  So Do Not Pay is a subscription model. It costs eighteen dollars a month and we have over two hundred thousand subscribers. And this really goes back to building a retentive business model. It took about five years of building products that were free before I finally felt comfortable charging a subscription. So from two thousand and fifteen to early twenty twenty, Do Not Pay was a free public service. We had no business model. And it was only when we started having a critical mass of products did we finally feel that we can make it a subscription. The first subscription price was only three dollars a month. And we chose that price because it was the minimum amount that you could charge without it being a joke.

• 17:55Speaker 00

  If we went into a VC meeting and said, we're charging one dollar a month for our subscription, they would think it's just a joke. But three dollars a month, maybe it could be a serious business one day. And then as we've added products and made it more useful, we've kept the price mostly the same in terms of the value you're getting, but we've increased it slightly and now it's eighteen dollars.

• 18:15Molly O'Shea?

  Do you have any add-on purchases on top of that? Like where do you get extra cushion?

• 18:20Speaker 00

  We don't have any add-on, so it's all you can eat. And our subscribers love it. They get access to everything. And with that said, though, we do have some crazy people who submit like one thousand letters a month. And if you reach like these absolute crazy limits, we don't want to ban them because they're our people. They're almost like us. So we might charge per cost at these crazy levels, but ninety-nine percent of users don't reach those crazy levels.

• 18:44Molly O'Shea?

  I wonder what kind of schemes they're running.

• 18:46Speaker 00

  I mean, they're like running law funds, maybe.

• 18:49Molly O'Shea?

  Last April, you had a pretty big announcement. And so I'll just, I'll frame this out. So unlike probably eighty percent of startups, you're actually generating cash flow. And even more, unlike probably ninety-nine percent, if not ninety-nine point five percent, you're generating enough to pay dividends back to investors. And you're one of the first companies to do that. That's a startup. What were you thinking here? Are you going to continue to pay dividends throughout the life cycle of the business?

• 19:19Speaker 00

  So it's it's like a factor of three things combining. So the first is that with automation and increasingly AI, you can build really big consumer businesses with very few people. So Do Not Pay has only like eleven full-time employees, but hundreds of thousands of paying customers. And we automate things like customer support. So if someone writes in asking for a refund, our system identifies the email, classifies it, pre-issues the refund, things like that. So you don't need to hire like fifty people for customer support anymore. And all of all of these business functions can be increasingly automated with AI. The second is that employees and investors are really tired of money losing businesses.

• 20:04Speaker 00

  It's no surprise that in the past year, Google, Meta and Amazon have either paid dividends for the very first time, I think in Google's case, or increased the level of dividends that they pay. And that's the sign of what investors are demanding. And then the final thing is that it's a well-known saying in consumer businesses that I think like fifty percent of the VC dollars or fifty percent of the revenue go to Google and Facebook ads with paid acquisition. And with us, that wasn't the case. We managed to grow organically through these viral media moments and also through our SEO strategy. And so we were looking at all of these things and we are fortunate to have much more money than we've raised. And we thought it would be a really nice bonus and win for everyone, especially since we've all been working on it for so long,

• 20:48Speaker 00

  to pay a dividend to both investors and all shareholders, including employees.

• 20:53Molly O'Shea?

  Wow, that's crazy. Given that's such a strong signal to the market, do you have investors constantly in your inbox?

• 21:00Speaker 00

  So there are different types of investors. Some investors would probably want us to burn more money, but some are really happy to get the cash flow. So I think everyone has different goals. In terms of my goals for the business, I don't think growth and profitability can be mutually exclusive. So we're still growing a lot and we're actually thinking of acquiring different businesses to add to our products. And we're also hiring a lot. So my Goal is to just keep growing the business and maybe we will pay more dividends. But we're also open to just following the OpenAI model if the right opportunity presents itself. We don't want to do anything stupid and we're very profitable right now. But we are, we're not kind of focusing on profitability. We're focused on building the biggest outcome possible.

• 21:43Molly O'Shea?

  Right, right. And you've raised around twenty three million dollars to date from some of the flashiest Silicon Valley names. I could probably run through the list, it would take a while. Do you have any favorite investors or any particular ones that stood out throughout your journey? Or were particularly helpful?

• 22:01Speaker 00

  Our most helpful per dollar invested has to be Marsha from Day One Ventures. So I was doing the PR kind of guerrilla style with Do Not Pay where I pitched journalists. And we were actually fairly successful, but Marsha really made me feel, think bigger. And she actually managed to get us like the Today Show twice at crucial points. Where our metrics increased by twenty percent in a day as we were raising rounds. And that really cemented both our user base and managing to close these rounds. So Marsha has been an amazing friend and investor. In terms of blue chip institutional investors, Andreessen Horowitz is really amazing. And Alex Rampell there is a genius and he's really helped me think through a lot of things as I've grown through the business.

• 22:45Molly O'Shea?

  What's it like working with Andreessen and their platform?

• 22:48Speaker 00

  They're really, really incredible because they know everyone. So going back to writing big corporations, we're actually trying something new where we're partnering with a big company to give free Do Not Pay subscriptions to their entire customer base. And they have a whole enterprise partnerships team that's helping make that happen. So I think in terms of like partnerships and thinking in new directions and also strategic thinking, getting an institutional VC is really helpful. I see a lot of founders where their very first round is like angels at a high price. And I think that's really a bad idea. I do a lot of angel investing and I tell founders the best thing you can do is get an institutional top tier investor in from the very beginning because they stay with you throughout the life cycle of the company.

• 23:32Speaker 00

  And they typically have ownership requirements between Ten and twenty percent. So you might as well get them when you have nothing, just an idea, rather than give up ten to twenty percent when you have significant revenue.

• 23:44Molly O'Shea?

  We were gonna talk on this later, but I wanted to bring it up now. You have self reclaimed as one of the most active Thiel fellow investors. So how many Thiel fellow companies have you invested in and what exactly was your strategy there?

• 23:59Speaker 00

  So I think statistically, I'm fortunate to be in the most Thiel fellows out of anyone. Just before this interview, I was actually counting and I only got through to twenty twenty four to twenty nineteen and that already got me to thirty three. And then in the class of twenty twenty three, so last year, I was in forty five percent of the fellows. So nine out of twenty. And I really also got into that by accident. So I spent three and a half years at Stanford. I basically completed everything at Stanford, all the degree requirements and things like that. But just as I was about to finish, I got awarded the Thiel Fellowship and I signed a contract not to confirm my degree.

• 24:40Speaker 00

  And I received a hundred K over installments over two years. And I lived the do not pay lifestyle. At the time, I was like living in the office. I had a like poor, like bad apartment, but I would just like mostly sleep in the office. And so I didn't really need the hundred K. And so I decided I'm going to invest it. And the first opportunity to invest it came very quickly because it turned out that not only did they give me the Thiel Fellowship, they wanted me to actually interview the next year's Thiel fellows. And so they said, you want to form part of the interview committee? And I think they liked me because I was very good with spotting the red flags.

• 25:22Speaker 00

  And so I would, I'm a very cynical person, so I would identify the ones that shouldn't get it. And so that's why I got into the committee. And I started interviewing these prospective fellows and I was blown away by what other entrepreneurs were working on. I was particularly blown away because even at entrepreneurial place like Stanford, a lot of the people at Stanford just want to go work at Google or Facebook. Book or V V B V C's, but it was amazing interviewing people and they're like, I want to, I don't know, like build genetic testing or things like that at the age of seventeen. And even inspired me working on a software company for consumers, maybe I should think bigger. So there was one person that I interviewed called Adam Guild and he's now the founder of a company called Owner.com.

• 26:07Speaker 00

  And I interviewed him and I was so blown away by his interview. He was consulting for different restaurants and companies and things like that. So he wasn't really, he hadn't really formed a company yet. And so I was trying to hire him for Do Not Pay. And so I flew him out to San Francisco and gave him a spot at the Do Not Pay office. And after about a day of him meeting the team and hanging out at the Do Not Pay office, I took him to Umami Burger on in Barcadaro. And I said, well, what do you think? Are you willing to join Do Not Pay as the head of growth? And he was like, I'm really sorry, I can't. I'm actually been doing some reflecting and I want to start my own company. So I decided at that split second, I was going to take my Thiel Fellowship money,

• 26:50Speaker 00

  all of the money after taxes and invest it in him. And that investment is up over a hundred X. And it really made me realize that this idea of being someone's first investor and helping them, especially when they're young, where there's like such high volatility and they can like grow so quickly is really lucrative. And so I've since raised three funds to do just that. I've deployed about thirty million just in Thiel Fellows alone. And also other great entrepreneurs. One shout out, for example, is Riverside, the platform we're recording on. He was very briefly did some work for Do Not Pay. And he said he's, and he's a, Nadav, the founder, said,

• 27:34Speaker 00

  I'm starting this podcasting tool, all the existing ones suck. And so I was like, okay. So I think it's just really helpful to monetize like the smartest communities you're in. And we're only a few years in, obviously the results on paper look great. I'll know in a few years if it's all worked. I'm in some like well-known names where the valuation has gone up a lot, but the initial entry price. Was in the growth stages like Figma and then I've also been the first investor in like the latest a kind of batch of really cool companies from Owner, Wanda, all sorts of interesting ones. So we'll see.

• 28:06Molly O'Shea?

  That's incredible. And shout out to Riverside because this platform is probably the best platform I've ever worked with. And they make product updates all the time that are like not incremental, but like substantial, substantial changes that you're like, holy crap. Thank you. But back to the Teal Fellowship. Can you explain more about how that's structured? Cause I don't think most people know how the Teal Fellowship works. And especially given that you were in it, you have a really good perspective.

• 28:32Speaker 00

  Yeah. So it's a nonprofit grant. They don't take any equity and it's not like an investing program. They're really not interested in investing in you. And certainly, maybe if you were fundraising, you might be able to get an introduction to Peter Thiel or Founders Fund. But that's really not the goal of the program. It truly is a nonprofit, nonprofit focus. And because of that, they only care about impact since they're not taking equity. So they don't really care if you're building something boring, even if it's lucrative. They want to give grants to the 20 most high impact entrepreneurs, either as nonprofit or for profit. So it's 20 people a year and they give you a hundred K. And because it's sometimes even 17 year olds, they're giving a hundred K to, they don't give it upfront. So they pay it quarterly. And the best thing about the fellowship is, is not the money,

• 29:17Speaker 00

  but it's the events and kind of community. So once a year, they will fly out the entire class to like a remote location and do a retreat. And as I mentioned, lots of people at Stanford are like focused on joining big VC funds or big consulting funds. So just having that network in the Teal Fellowship of people who are your age, who are like, how do I hire someone who's three times my age? Um, and answering those questions and having that community be able to deal with that was super helpful for me.

• 29:46Molly O'Shea?

  Do you think that created your bias towards younger founders? I know you mentioned you like first time founders, people that are willing to take more risk. What's your opinion on the current state of entrepreneurs and founders?

• 29:59Speaker 00

  I think it's too easy to raise money right now. When I started, Do Not Pay in 2015, 2016. You really had to grind to even raise 500K. Or maybe I was just bad at pitching, which I'm sure was true. But the market was a lot less receptive to just throwing money at people. Fast forward to today and you can just call one person and raise 10 million very easily. Or at least some people can. And I think it's too easy. And that's why I really love backing young entrepreneurs. Because they don't have the credentials to do that and they have everything to lose. And so when I would back a Thiel fellow or someone who's 18 and just dropped out of even high school. The first thing they'll do is they'll build the product.

• 30:40Speaker 00

  But I feel like when a Google engineer or an OpenAI engineer raises, sometimes even or like a well-known Silicon Valley founder, sometimes can even raise like a billion for the seed. The first thing they'll do is they won't build the product. They'll hire 100, 200 people or 50 people. And so this culture around young people of because they have everything to lose, they move much more quickly. And one of my other best investments was actually my Stanford roommate. So I'm not too negative on Stanford. And he just built this amazing product. And now it processes a huge number of insurance claims in America. And it's one of the fastest growing companies. I think when you go from zero to one, you have to build so quickly that

• 31:23Speaker 00

  young people just have a higher speed of iteration that make them better investments. And then the second thing I'll say is that seed and pre-seed investing is really about buying an option. You're buying the option that this becomes really, really big. If like anyone is, I'm not an expert in options pricing, but there's like a formula of option pricing. And options are more valuable, the more volatile things are. And young people have the most volatility. So what I mean by that is maybe at 17, I couldn't even like string together a sentence. And so if you can invest in someone when they can't string together a sentence and then they learn to pitch and they have the substance, the volatility is like huge.

• 32:05Speaker 00

  And the potential for them to like a thousand X is much higher than someone who's already been in the game for 10 years.

• 32:12Molly O'Shea?

  When do you think it's the right time? To take a high risk approach versus when to play it safe.

• 32:18Speaker 00

  It's it's not for everyone. I think if you have something calling your name. So I didn't drop out of Stanford because of the Teal Fellowship. I dropped out because I had a choice between taking a final for a class and keeping the servers running for hundreds of thousands of people. And I didn't want to let down my users. So I was just too busy. I think that the one thing I would push back against though is there's some people who say I have to do this to do this. So they say, I want to get five years of experience working for something and then I'm going to build a company in that space. And I think that's completely the wrong idea because the world changes so quickly. You might as well just start now and learn on the job because in five years' time, your learnings will be irrelevant.

• 33:01Molly O'Shea?

  What do you think this means to be a leader in Silicon Valley today when it's so easy to be a founder?

• 33:08Speaker 00

  I think we're in a new era of independent thinking where the old guard, and by the old, I'm kind of aging myself. The old guard was maybe like 2019 and earlier. It was all about like the establishment, like you know, so and so from Dropbox or things like that. But now the companies that are doing really well, the ones where they've had a really unique insight and a founder being a very powerful voice for that insight. So like Shane from Polymarket, he was like very powerful, pushing through this like prediction market idea where no one would have agreed with that. And now Polymarket is absolutely huge. So having like your own opinion is like very fashionable again. And that wasn't the case maybe even two years ago.

• 33:51Speaker 00

  And tied into that, I really think that Twitter has helped me immensely. And I look at founders and they say, no, I'm not on Twitter. And I think they're crazy. I think you really have to focus on like building an online presence and LinkedIn is not going to cut it. So Twitter is really important.

• 34:08Molly O'Shea?

  Twitter is where the deep crew is. That's where everyone really is. As we close out, I have two more questions. This one question is from Mené. So shout out to Mené. He wants to know, where did you learn your leadership skills and your values? And is there anyone you particularly? Really look up to.

• 34:26Speaker 00

  I think the biggest influence on my life was probably my dad, who's a human rights activist. He is responsible for a lot of the freezing of Putin's money around the world and also the rest of the Russian mafia. And that unfortunately led to a lot of like threats against him and the whole family. And they're like chasing him around the world and threatening violence and trying to get him arrested. I think he has multiple, probably over six arrest warrants out right now from Russia for all sorts of different made up political crimes. And that really taught me to be fearless. Obviously with do not pay, there are like minor issues on a day to day basis with like angry lawyers and things like that. But having the Russia mafia after your family really puts everything into perspective.

• 35:10Speaker 00

  And so it taught me the value of courage and standing up for what you believe in and always never giving up.

• 35:16Molly O'Shea?

  That's an incredible role model and wow, what a lesson. Okay, as we, as we end, what are you most looking forward to in 2025?

• 35:24Speaker 00

  I think the biggest thing is, it's a good question. So I'm looking forward to two things. On the founder's side, I think voice models have become unbelievably good. And it's like 90% where actually the voice itself passes the Turing test where you can't tell this is a kind of artificial voice. And we're already doing like thousands of customer service calls at that 90% level. But I really think it will get to 100% in the next 12 months. And once you have AI where you can't tell it's a voice on the phone, I think it enables a lot of really exciting use cases for do not pay. And then on the investing side, I'm excited for the biggest tech bubble ever.

• 36:06Speaker 00

  I feel like I'm in a really good position. I'm in some of the best companies and with really good substance. And I actually think, I think this is controversial where kind of series A through C companies are undervalued right now outside of AI. I was looking at like McDonald's revenue and McDonald's on the public market trades at like 10 times revenue. And so I think that some of these tech businesses are a lot better than McDonald's. And I think they It should actually be valued much more. And I think that with the election and a lot of things, people will start to recognize that maybe the correction was a bit too much for Series A through C companies. And we'll have another big tech bubble. So that's what I'm excited about.

• 36:50Molly O'Shea?

  I have to challenge you on that. So what do you think's going to happen when the public markets open again? And companies start getting actually weighed and valued against realistic comps?

• 37:00Speaker 00

  I think that the comps should be higher. I think like SaaS is trading, at least like non-AI SaaS is trading at like a historical low. And there's a reason that it traded high in the past. These are subscription businesses. They have positive net dollar retention. They're growing much more quickly than the traditional comps. So I think the multiple will be higher. And I think that this breed of companies that survived over the past few years are really battle tested and are much more resilient than the ones that went public last time. So I think it will actually be a positive outlook. And then I also think that M and A will heat up a lot again. There are some companies I invested in that had acquisitions only to be blocked by various evil government.

• 37:45Speaker 00

  And I feel like the government agencies were literally like stealing from me personally as a small investor by not letting these acquisitions go through. So I'm excited for M and A as well to heat up.

• 37:55Molly O'Shea?

  That's exciting and that's very positive. Well, Joshua, this was so fun. Thank you so much for joining us and it was a pleasure.

• 38:03Speaker 00

  Thank you.

• 38:15Speaker 02

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• 39:00Speaker 02

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