The Bitcoin Expert: America’s $40 Trillion Financial Reset Has Begun - Do This Now!

Claude: Get started with Claude today at https://claude.ai/icedcoffee Gusto: Try Gusto for FREE for 3 months at https://gusto.com/ICED Upwork: Post your job free at http://upwork.com/COFFEE and connect with top talent to grow your business. Shopify: If you’re ready to launch your business before Black Friday, go to https://shopify.com/ich to start your FREE trial FOLLOW US ON SOCIALS: 𝗜𝗚: https://www.instagram.com/icedcoffeehour 𝗝𝗔𝗖𝗞: https://www.instagram.com/jlsselby 𝗚𝗥𝗔𝗛𝗔𝗠: https://www.instagram.com/gpstephan 𝗖𝗹𝗶𝗽𝘀 𝗖𝗵𝗮𝗻𝗻𝗲𝗹: https://www.youtube.com/c/TheIcedCoffeeHourClips 𝗫.𝗰𝗼𝗺: https://x.com/TheICHpodcast 𝗧𝗶𝗸𝗧𝗼𝗸: https://www.tiktok.com/@theicedcoffeehour 𝗦𝗽𝗼𝘁𝗶𝗳𝘆: https://open.spotify.com/show/5c2uoXBQkOjIiCOf60jJj7 𝗔𝗽𝗽𝗹𝗲: https://podcasts.apple.com/us/podcast/the-iced-coffee-hour/id1515070058 00:00:00 - Intro 00:00:56 - Going All In On Bitcoin 00:08:01 - Is It Too Late To Buy Bitcoin? 00:15:31 - Sponsor: Claude 00:17:11 - How Much Bitcoin Should You Own? 00:27:24 - Sponsor: Gusto 00:28:45 - Sponsor: Upwork 00:30:03 - Could AI Make Bitcoin Obsolete? 00:35:41 - Should You Buy Bitcoin Companies Instead? 00:41:12 - Could Bitcoin Go To Zero? 00:47:27 - Who Is Satoshi Nakamoto? 00:53:14 - Bitcoin vs. The ETF 00:59:06 - Sponsor: Shopify 01:00:00 - On John McAfee's Boat With 100 Guns 01:07:08 - Graham's Dogecoin Regret 01:14:30 - Why Selling Is The Hardest Part 01:20:39 - Bullish or Bearish On America? 01:28:39 - Is It Safe To Give AI Your Finances? 01:35:38 - Rapid Fire Predictions 01:45:07 - WATCH THE NEXT EPISODE! For sponsorships or business inquiries reach out to: [email protected] Apply for The Index Membership: https://entertheindex.com/ For Podcast Inquiries, please DM @icedcoffeehour on Instagram! *Some of the links and other products that appear on this video are from companies which Graham Stephan & Jack Selby will earn an affiliate commission or referral bonus. Graham Stephan & Jack Selby are part of an affiliate network and receives compensation for sending traffic to partner sites. The content in this video is accurate as of the posting date. Some of the offers mentioned may no longer be available. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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

• 0:01Speaker 00

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration blog, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18 plus.

• 0:26Speaker 01

  I watched Bitcoin fall 50% in a 10-hour period, and I was on the couch curled up in a ball and like saying to my now-wife, I think our net worth might go to zero today.

• 0:34Speaker 02

  Bitcoin is a resilient asset that is really serving as global insurance. And so anytime that there's chaos in the world, there's going to be people who run to Bitcoin.

• 0:41Speaker 01

  There's two assets you need for the future we're headed towards. Bitcoin and AI.

• 0:44Graham Stephan?

  Is it too late to buy Bitcoin?

• 0:46Speaker 01

  Bitcoin is going to continue to go up for the rest of our lives because the politicians are going to print money for the rest of our lives. We have a public company with hundreds of millions of dollars in the balance sheet. We have more bots and agents that work at the company than humans. Well, where is the world going? The world is going to start to morph to accommodate for the bots and agents, not for humans.

• 1:04Graham Stephan?

  Do you think AI is going to make most people richer or just the top few?

• 1:14Jack Selby?

  The pump. Thank you so much for coming on the Iced Coffee Hour.

• 1:18Speaker 01

  I'm very excited to do this. You guys got a beautiful place here, so excited to talk.

• 1:22Jack Selby?

  Thank you. So I did a bunch of research. I used every LLM imaginable trying to figure out what is your net worth? Because it's very mysterious. They all estimated between 100 and 200 million dollars. Is that accurate?

• 1:35Speaker 01

  I have no clue.

• 1:36Jack Selby?

  You don't know?

• 1:37Speaker 01

  No. I have a good sense for liquid assets. And then on the private investing side, you know, one of the benefits of investing in private companies is you can't sell. So I've been an investor in companies and they go from zero to billions of dollars very quickly. And you're like, wow, I'm rich. And then they go to zero and you're like, okay, well, that was kind of fake money. And then there's been other ones that have kind of petered along for years and years and years. And then all of a sudden they sell for some big number. And you're like, okay, that's not the outcome I expected. So my portfolio historically has been Bitcoin and then tons of private companies. I've invested over 300 private companies, either directly or through funds that I've managed. And the reason why I like that Bitcoin, I think of as an illiquid asset, even though it's liquid.

• 2:22Speaker 01

  But the private companies, I can't sell. And I think that I'm actually a pretty bad public market investor because I am, if I get new information, I like to think about it. And that is not very good. If you want to be a long-term investor with something that's liquid and trades on a day-to-day basis. And so I tend to just, when I buy assets, I say, I'm not going to touch them.

• 2:41Graham Stephan?

  So I mainly know you for Bitcoin. I think I started following you many years ago. And I am curious, when did you first buy Bitcoin? At what price? And what convinced you that this was going to go a lot higher?

• 2:55Speaker 01

  Two different times people tried to convince me. 2012 and 2015. 2012 was a guy on Twitter DMing me and I was like, this is stupid. 2015, we hired David Marcus from PayPal into Facebook to run Messenger. He sat 100 feet away from me and wouldn't stop talking about Bitcoin. I turned to an engineer and I said, what do you think? It's stupid. Didn't buy. 2016, I start with ETH. Mine goes up, I saw 150 bucks. ETH goes to $1,400 that year. I feel like a complete idiot and I say, I gotta, I gotta learn. I gotta sit down and I gotta study this stuff. And my now-wife would tell you, I literally had textbooks, articles printed out. I was like almost in school studying this stuff. And I built incredible conviction around Bitcoin.

• 3:39Speaker 01

  And when Bitcoin dropped in 2018, I pretty much took 90 to 95% of all the money I had to my name and I put in Bitcoin at $3,200.

• 3:48Graham Stephan?

  How much money did you put in Bitcoin at $3,200?

• 3:51Speaker 01

  Initially, it was hundreds of thousands of dollars. But then I had at that point met a gentleman named Mark Yusko, who I had partnered with and we'd started to raise a lot of money from a professional standpoint. And when I first met Mark, Mark was very unique in that he had invested in, he was one of the first checks into Chase Coleman's Tiger Global. He had backed Howard Marks and Oaktree in a ton of different funds. He knew Julian Robertson. Like he was really well-connected in the institutional finance world. And one of the questions I asked Mark when I first met him was, I said, what separates the top three guys from the top 1%? So not the top 1% to the top 50%, but what the top three guys from the top 1%? And without hesitation, he said to me, they press their winners harder than anyone

• 4:35Speaker 01

  and they cut their losers faster than anyone. And for whatever reason, I was seared in my brain. When I bought the Bitcoin at $3,200, I then said to myself, Mark told me they press their winners harder than anyone. And I had immense conviction in Bitcoin. And I took every single dollar I could possibly make and just kept buying and buying and buying and buying. And I did that all through the 2018, 2019 bear market. And I ended up with a lot more Bitcoin than that initial purchase because it went from 32, 33, 34, 35. And so I was essentially just dollar cost averaging in that entire bear market. And I credit Mark a lot with that one lesson, probably completely changed my life.

• 5:17Graham Stephan?

  But you know what? Your entire life could have been different because had you invested six months earlier, it was 20,000. And so who's to say you didn't hear, press your winners harder when you went in Bitcoin at, let's say, 18,000? It goes to 20 and then you cut your loser when it drops to 15 and you never invest again.

• 5:35Speaker 01

  If you bought at 20,000 and you sold, you obviously wouldn't make money. If you bought at 20,000, you held today, long time, decade or so, right? You would be up, but not necessarily nearly as much as if you bought at 3,000. If you had bought at 20,000 and dollar cost averaged all the way down and back up, so you just kept buying as much as you possibly could, you would have made a lot of money because your blended price would be closer to like $5,000. I wasn't a very good student at all. But Bitcoin really gave me an education, not only in behavioral finance, investing, economics, history, you know, philosophy, all this stuff. But the thing it probably taught me more than anything is you want to find volatility when you are investing, which is kind of counterintuitive

• 6:17Speaker 01

  because that volatility will present you opportunities to buy more. But it also is how you drive asymmetry in the investment world.

• 6:24Graham Stephan?

  So for people uneducated in the markets, what's going on with crypto today?

• 6:29Speaker 01

  I think that there are three different groups that are interested in crypto. There's the hardcore believers. I would put them as like the religious zealots that no matter what happens, they're never selling. I would put there being people who have traditional backgrounds, but became crypto people. And then there are people in the traditional world who they don't care if they're trading oil, gold, Bitcoin stocks. They're just looking to make money.

• 6:49Jack Selby?

  And what are you?

• 6:50Speaker 01

  I would put myself in the middle.

• 6:51Jack Selby?

  And what is Michael Saylor?

• 6:53Speaker 01

  I think that Michael Saylor is one of the hardcore.

• 6:57Jack Selby?

  Bitcoin is his religion.

• 6:59Speaker 01

  I don't want to go that far. I just think that one of Michael Saylor's superpowers is that he has an incredible ability to focus and say no to a lot of things. As I've written about in the past, that also can be blinding at times to certain things. It's kind of the purpose of focus is that you are intentionally saying, I'm not going to pay attention to anything else. And so with Bitcoin in particular, it is highly volatile and it has been a great thing to do for a number of years is to just focus on buy as much Bitcoin as you possibly can. I think that now we are entering a world where there's a lot of things that are going on. For example, when Bitcoin starts to infiltrate more of the traditional portfolios, you now need to pay attention to, well, what is going to happen in interest rates, inflation, et cetera?

• 7:42Speaker 01

  Not because you're going to sell, but because it's going to have an impact on Bitcoin. And so the reason why I like being in the middle is there was a long period of time where I would go and I would talk to the hardcore crypto people and they would be like, why do you own Bitcoin? That's the boomer coin. That is like the least interesting crypto coin. I hold and they would tell me some crazy coin that I'd never heard of before. And that was what they were investing in. But then I would go and I would talk to people on Wall Street and they would be like, what? You own Bitcoin? That is so risky. And what I learned was I want to hold the thing that is the riskiest asset in the most conservative people's portfolio, but it is the most conservative thing in the highest risk takers people's portfolio. And Bitcoin has kind of found a home there where to the crypto people, they're very uninterested in it for the most part because they think that it's not going to perform 20X in a year.

• 8:23Speaker 01

  But to the Wall Street people, they've never seen an asset that goes up 60% compounded for a decade.

• 8:29Jack Selby?

  So what do you think then are the biggest risks to Bitcoin?

• 8:32Speaker 01

  I think that there is much less of a risk of some sort of regulatory capture. But I do think that you could still see a situation where if all of a sudden certain people got into political positions and they wanted to really become adversarial to Bitcoin again, that could potentially be a headwind. I don't think they could shut down Bitcoin. I don't think they could stop Bitcoin, but I definitely think they could create a lot of problems. I also think that there are some technical things that the Bitcoin community is trying to figure out how to address. I am not a big believer that quantum is like an imminent major threat to Bitcoin. But I understand that quantum is an industry that is changing very quickly and it is advancing. And so we need to pay attention to what those advancements are because ultimately Bitcoin's value is tied to the cryptography.

• 9:16Speaker 01

  And so if something came along that could break Bitcoin's cryptography, that would be a problem. I also think that AI is not so much a problem for Bitcoin, the blockchain, or Bitcoin, the asset, as much as AI is now creating a very big kind of vector threat for individuals who hold Bitcoin. If you get a call and you think it's your wife saying, hey, will you send this to me? And you do it. If you get an email, it's a phishing email, but it looks realistic. If you're somehow socially engineered using AI or a fake ID or something like that, that's a huge problem. If you look at, for example, there was a recent incident with a hardware provider where somebody it looks like was able to use AI to basically reverse engineer a very technical component of that wallet.

• 10:01Speaker 01

  Now, these are people who were using that product, who were kind of the hardcore Bitcoiners. It's kind of like a strike in a, to the heart or the headquarters of the true believers. And most of these people were very upset because they were like, look, I didn't leave my Bitcoin on an exchange. I didn't own the ETF. I had self-custody. My Bitcoin never had touched the internet. I was, you know, in this great position. If that happens more often, then the foundational belief of self-custody in Bitcoin could be at risk. I don't think we're there yet now. But I think that's where AI could be an attack surface, is the ability to use AI to actually hurt philosophically or intellectually the Bitcoiners themselves. And so all of those threats are things that could wound Bitcoin, but I don't see anything on the horizon outside of quantum getting to a certain position.

• 10:46Graham Stephan?

  So what did you read that convinced you to go all in on Bitcoin?

• 10:49Speaker 01

  Everything, literally anything and everything I could find.

• 10:52Graham Stephan?

  What stands out to you?

• 10:53Speaker 01

  I think that Sayfadeen Moussa's book, The Bitcoin Standard, probably the most important thing was actually not what I read because a lot of it was technical. It's like you sit down, you're like, I'm going to read the Bitcoin white paper. I'm going to learn about Bitcoin. You get like a page in and you're like, dude, I am way too dumb for this. Like, what does this thing mean? I don't know. There's equations, there's letters and numbers, like this is hard. Talking to people was incredibly valuable. And

• 11:18Speaker 01

  This is about a year and a half after this, but I remember going, Mark Usgo took me to meet one of these legends of finance and we went and we saw Julian Robertson. We saw Howard Marks and a couple of other people all in one single day. And to varying degrees, they were open to listening, but none of them were like, great idea. I'm going to go buy Bitcoin. And some of them were like, this is a courtesy meeting. It's 15 minutes, like, nice to see you guys. Thanks, but no thanks. And I remember at the end of the day, Mark was very frustrated. And I think that he probably felt a little bit like, hey, I invested in all these guys' funds for a long time. None of them are interested in the idea I have. I think some of it was frankly, like, well, the smart people aren't into this. You know, am I making a mistake? And I said to him, I said, Mark, the fact they're not interested is the opportunity.

• 12:04Speaker 01

  If all of the people were convinced, that would mean that it was consensus. And that would mean that most of the value would already be kind of captured. This is something that I believe is early and will become consensus. Thankfully, we were right on that. But like, to me, actually, that day was very formidable because I got to see these people who I really respected and thought highly of, and they were not interested at all. And so it was clear, either we're idiots or we're early. We're going to get paid if we're early. If we're idiots, we're going to lose all our money.

• 12:32Graham Stephan?

  So is it too late to buy Bitcoin?

• 12:34Speaker 01

  No. Bitcoin is going to continue to go up for the rest of our lives because the politicians are going to print money for the rest of our lives. So if you look at the stock market, the stock market, the S and P over the last five years is up about 70%. Sounds like an amazing return. If you look at Bitcoin, gold and land as equal sleeves of a portfolio, that portfolio is up about 170% over the same five year period. During that five years, the reason why that period is really important is the dollar has lost 30% of its purchasing power over five years. So stocks, which are supposed to be productive assets, outperform things like Bitcoin and gold have actually lagged because almost all investment returns right now are being driven by money printing. The stock market is all money printing.

• 13:18Speaker 01

  If they shut off the money printer, the stock market will stop going up.

• 13:20Graham Stephan?

  But how do we know Bitcoin is going to keep going up? How do we know that? I mean, we could all say that they're going to print more money and therefore printing more money is going to cause the price to go up. But how do we know that is the case? Cause they printed a lot of money over the last year and Bitcoin has not gone up in price.

• 13:35Speaker 01

  Well, you can quantify it. And if you look, you can measure the sensitivity of an asset to money printing or global liquidity. Bitcoin is the most sensitive asset to money printing globally. So if you look over all these years, every time they print money, what is the asset that responds most to that money printing? So it's not like a, oh, I think it is. It is a quantifiable metric that you can go, there's plenty of studies that are put out there. Sam Callahan and Lynn Alden probably have like the quintessential study that shows Bitcoin is the single most sensitive asset to money print. So when you look at that, now that's in the past. That doesn't mean it has to be true in the future, but if you just look and say, okay, I don't think that's going to change, then going forward, a great way to essentially insulate yourself from money printing is buy Bitcoin.

• 14:18Speaker 01

  Now, if you notice, I didn't say, hey, just put all your money in Bitcoin. Bitcoin, gold, land. I think that there's multiple asset classes that all benefit from this. I tend to think that either Bitcoin or some combination of them is the way that most people should look at it. Cause I actually don't think that it's so much about the return as much as I don't think a lot of people can handle the volatility. You know, buying Bitcoin was great in 2018 at 3,000, 3,500 bucks. I lived through multiple 50 plus percent drawdowns. On March 12th, I believe it was of 2020, I watched Bitcoin go from $8,000 to under $4,000 in a single trading session. That day, I literally wrote a letter to a bunch of investors and I said, we are in a global liquidity crisis. And I had a chart that showed what happened in 2008 with gold.

• 15:03Speaker 01

  And over six months, gold's price had drawn down during the global liquidity and then it had basically recovered. So I clearly articulated in the morning when I was emotionally sober, what was happening? We're in a liquidity crisis. Assets are going to go down. And then I watched Bitcoin fall 50% in a 10 hour period. And I was on the couch curled up in a ball and like saying to my now wife, I think our net worth might go to zero today. You can be prepared, you can be mentally, you know, sober, understand what's happening. When you watch that asset fall, thank God she was there because she looks at me and she goes, you're already all in, just buy more.

• 15:40Speaker 01

  I didn't have the emotional control, nor the ability to think that clearly. But her, who pretty much was like, my boyfriend is an idiot and is like all in, well, you might as well just stay all in.

• 15:53Graham Stephan?

  What if she was being sarcastic to you? Like, you're already all in, what's a little more?

• 15:57Jack Selby?

  Guys, let's be honest, thinking clearly is a huge part of success in business and investing. But as we just heard, knowing the numbers does not mean that your emotions won't get in the way. A lot of the time, all you need to do is step back, question your assumptions and look at things from another angle.

• 16:11Graham Stephan?

  Yeah. And we found that incredibly useful in our own business, like having something to help us work through a decision instead of just going with the first instinct is a big part of why we use our partner Claude.

• 16:21Jack Selby?

  Claude is the AI for problem solvers. It's the collaborator that understands your entire workflow and thinks with you, not for you.

• 16:27Graham Stephan?

  Whether you're debugging code at midnight, building a financial model, or strategizing your next business move, Claude extends your thinking to tackle the problems that matter.

• 16:36Jack Selby?

  We use it to analyze channel data, spot patterns and think through what we can do differently. You can ask follow-up questions, challenge an idea and figure out what you might be overlooking.

• 16:43Graham Stephan?

  And it's really useful for the everyday work too. Like, no joke, we're using it all the time to draft emails, working through video titles, organizing research, by the way, for the interviews. There's literally so many ways that you could use Claude to help your business.

• 16:57Jack Selby?

  And what is absolutely mind blowing is we even use Claude, I kid you not, to edit our videos now. Last night, we finished filming at 9:00 PM. This morning, that exact episode was about 95% done, barring some finishing touches, which is absurd. And it's edited literally better than what we would have been able to do just manually. Like this is serious. If you're not using Claude, you absolutely need to be using it.

• 17:19Graham Stephan?

  Plus it connects with Google Drive, Gmail and Slack. So it could work with the context you already have.

• 17:24Jack Selby?

  For problems worth solving, get started with Claude at claude.ai/icedcoffee.

• 17:29Graham Stephan?

  It's claude.ai/icedcoffee. And check out Claude Pro, by the way, which includes access to all of the features mentioned in today's episode. Claude.ai/icedcoffee. What if she was being sarcastic to you? Like, you're already all in, what's a little more? You know, just like an offhand remark.

• 17:46Speaker 01

  If it had gone to zero, I would have told her, you better be being sarcastic. Look, it is this weird dynamic of, I think a lot of people like to pretend, oh, I knew. I had a lot of conviction. I put my money where my mouth was. There are multiple times where I've been like, am I right? And I think it's healthy. I don't think people should hide that. That day, when I watched Bitcoin fall 50%, I remember saying to myself, this could go to zero today. That is not a fun feeling, but that's why I say like, I don't think the average person should go put majority of their money, most of their money in Bitcoin, because I don't think that most people, one, want to live that way, two, can. And then three, I also think that it's not good for you.

• 18:28Speaker 01

  You know, I've told a story before that in 2019, my wife and I moved into a, an apartment, the first apartment we got together. And when we moved in, we went from her, uh, not so great studio apartment in New York to a one bedroom. And we thought like, wow, this is amazing. But we didn't have a couch. And I remember explaining to her the economics in a very rational way of if I buy the couch, we can buy one less Bitcoin. But I think this Bitcoin thing is going to appreciate and the couch is going to depreciate. So like, what if we wait a couple of months? And there's this famous photo of my wife sitting on the floor on a yoga mat, almost like the Steve Jobs famous thing with like the lamp next to him. And I think a huge part of what I attribute a lot of my success to is having a woman who frankly, was just as insane as I was.

• 19:14Speaker 01

  That's not a rational, normal thing, but I think that she kind of believed in the dream or the vision right alongside me. So when it drops 50%, she says, buy more. It's not very rational, but there was just something about, we've done the work, we understand this thing. And I think that having kind of a thought partner there was really helpful.

• 19:32Jack Selby?

  So how do you like Bitcoin at its current price around 80 ish thousand dollars?

• 19:36Speaker 01

  I like Bitcoin always. And not because I'm some like super religious Luddite about it.

• 19:43Speaker 01

  I think that Bitcoin is just the most sensitive asset to government printing. I was maybe to check myself intellectually, I was very excited about the whole Doge effort. I was like, wow. I used to tweet all the time. Why does no president even pretend to want to cut expenses? They, if you look in 2010 to like 2020, pretty much nobody even talked about, we're going to, you know, balance the budget. It was just like, we spend, that's what we do. Trump in the second term came in and he said, we're going to create Doge and we're going to cut and we're going to balance the budget. And I think for a moment, even if it, for everybody was like, for one hour, or for me, it was probably like two months, was like, it would be amazing if they balanced the budget. But then once it became clear as not, you know, Besson had this famous, like, we're

• 20:26Speaker 01

  going to run it hot, essentially speech where he was just like, that's no longer the, the story. Now we're just going to grow our way out of it. Bitcoin took off, everything took off.

• 20:34Jack Selby?

  So you would say to someone like me who has probably 1% of my entire portfolio in Bitcoin, that buying more at 77,000, around 80,000, whenever would probably be a good idea because 1% of your portfolio is not enough.

• 20:48Speaker 01

  If you are not into Bitcoin whatsoever, and you look at it from a pure portfolio construction standpoint, portfolio construction theory would tell you, you want to put as many non-correlated assets into a portfolio as possible, because it should increase the sharp ratio and decrease the correlation. So just like, if you're like an endowment and you're like, we have no religious view, we have no, you know, kind of loyalty to any asset, we're just trying to create a great portfolio from a math standpoint. Bitcoin historically has been non-correlated, not inversely correlated, but also not correlated. Now there have been times, especially over the last three or four years, where Bitcoin's correlation to tech stocks or the stock market has spiked significantly. Myself, other people in Bitcoin community, well, that's not really what Bitcoin's supposed to be.

• 21:31Speaker 01

  Bitcoin is supposed to be an asset that is non-correlated. One of my theories, which is very hard to prove, is that the reason why Bitcoin historically was non-correlated is because it wasn't held by the traditional investor. So it was held by a bunch of retail people who like, the average guy on the internet who held Bitcoin didn't care what interest rates were. It didn't care what the national debt necessarily, like the exact number, didn't care what the inflation reading was. They were like, I believe in Bitcoin. I buy it every day and I'm just going to hold Bitcoin. Today, a lot of Bitcoin, especially through the ETFs, are held by institutional investors. Sovereign wealth type funds, hedge funds, endowments, et cetera. You can see the filings where they're holding hundreds of millions of dollars of Bitcoin. Those people really care about interest rates, inflation, et cetera.

• 22:14Speaker 01

  And they make changes in their portfolio holistically. So if they think that interest rates are going to rise, they will sell their Bitcoin, they will sell their tech stocks, they will sell the assets that are sensitive to rates, and then they will go buy assets they think are insulated. So naturally, if I'm one of those investors and I think interest rates are going to rise, well, if I go sell my things I deem to be sensitive to rates, I'm selling my tech stocks and my Bitcoin together. That's correlation. I'm doing both of them at the same time. And so that's why the correlation, I think, has ticked up. And so if you go back to this idea of 1%, I actually think Bitcoin is a diversifier. So what you see is if you take a 60-40 portfolio and you put Bitcoin into the portfolio, Sharpe ratio goes up, correlations go down,

• 22:55Speaker 01

  and actually, the risk return becomes more attractive. So it's a little weird because you're putting a high-risk asset into the portfolio, but it reduces the risk by doing that.

• 23:05Graham Stephan?

  So for portfolio theory, then what is the mathematically correct percent of Bitcoin that should be reflected in a portfolio?

• 23:11Speaker 01

  It's very personalized. So if you are a 75-year-old person who is not working and needs cash flow, your Bitcoin allocation should be low to almost zero because you don't have the benefit of holding this thing for years if there's lots of volatility to it. If you're a 21-year-old kid, you should probably have a much higher allocation. There are people like very famous financial advisors. This guy, Rick Edelman.

• 23:36Graham Stephan?

  Whoa, whoa, whoa, hold on. What is very high allocation to Bitcoin? What does that mean?

• 23:40Speaker 01

  Rick Edelman is in the Financial Advisor Hall of Fame, which I didn't even know existed. He's in the Financial Advisor Hall of Fame. He says that young people should have up to 40% of their portfolio in crypto.

• 23:50Graham Stephan?

  Forty?

• 23:51Speaker 01

  Forty, four, zero percent. He says 10 to 40%, the younger you are, the closer to 40, the older you are, the closer to 10. Again, that is a very big number, but I look at that as, that is somebody who built a massive financial advisory firm doing traditional stuff, has done a lot of work on crypto more generally, and that is his kind of band.

• 24:10Graham Stephan?

  When did he say this?

• 24:12Speaker 01

  In the last two years.

• 24:13Graham Stephan?

  I mean, you can always cherry pick and say, oh, this person with all of these accreditations said this, and then Warren Buffett says this. Like, there's. Fidelity, I believe, did a study and they recommended 3%. Okay, so I'm at 1, Graham.

• 24:29Speaker 00

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome? That's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up require compatibility and availability varies 18 plus.

• 24:56Graham Stephan?

  Eight to 12, depending on where the prices.

• 25:00Speaker 01

  But did you allocate eight to 12, or you bought something and it went up and it just became a bigger percentage?

• 25:03Graham Stephan?

  I've just been dollar-cost averaging, and that turned into eight to 12. Are you up on Bitcoin? Depends on the allocation. I would say. Like a blended average cost. I bet I'm pretty much even. The Bitcoin that I bought initially, I think I'm up triple. So what really depends on the allocation. What percent of your portfolio is Bitcoin?

• 25:26Speaker 01

  Pure Bitcoin is probably somewhere in the 40 to 50% range now. Related in some form or fashion to Bitcoin. We have a public company that's got hundreds of millions of dollars of Bitcoin on its balance sheet. It's technically not Bitcoin, but we have an operating business with Bitcoin, and so it's like related. It's a very high percentage, right? But again, it goes back to, what is my conviction percentage that Bitcoin is going to be much higher in the future? It's definitely over 50%.

• 25:52Graham Stephan?

  So if you're willing to say that you're highly convicted in that way, what price targets do you see for Bitcoin?

• 25:58Speaker 01

  It doesn't really matter because one of the psychological tricks I've played on myself is that I've said Bitcoin, I'm going to hand to my grandchildren. And the reason why I've done that is that's how I deal with the volatility, is I'm going to hand them the Bitcoin, and if it's worth a lot, I'll be a genius. If it's not worth a lot, I'm going to be an idiot because I'm basically going to hand them air. But I psychologically have convinced myself, no matter what happens to the price, I'm never going to sell it because it's their Bitcoin.

• 26:22Graham Stephan?

  But if there's a chance even that it could be air, why not just take 10% of it and throw it in VLO or something?

• 26:29Speaker 01

  Well, what I said was, let's say 50% of my portfolio is Bitcoin pure, and then 50%. So go back to 2023. I basically had private companies and I had Bitcoin, but I explicitly said to myself, I basically need to rebuild my entire financial life. Bitcoin had drawn down a lot, right? I had a lot of volatility. I was starting to build a family. There were a lot of things happening in my life. And so I said to myself, I'm not going to touch this. But basically, if I did it once, can I do it a second time? Do I actually have the skill and the ability to do this? And I went and I rebuilt an entirely new financial life, not touching the Bitcoin. But I went and I built a bunch of companies. I built an investment firm. I built a public company, et cetera. And the whole idea was that's my diversification. I was super concentrated here, put that to the side.

• 27:14Speaker 01

  Now I'm going to go be super concentrated all over again and do something different. And by doing that, I created diversity in my finances by actually balancing it out.

• 27:23Graham Stephan?

  All right, so what would it take for Bitcoin to hit a million dollars?

• 27:26Speaker 01

  Government to keep printing money.

• 27:27Graham Stephan?

  For how long?

• 27:29Speaker 01

  Nothing needs to change for Bitcoin to hit a million dollars. Bitcoin will hit a million dollars in our lifetime, given enough time. Because the same reason why people say gold will never go to 5,000, or the S and P will never hit, pick a price target, they just kept printing money. And it's accelerating. We have a $40 trillion national debt. We have a trillion-dollar annual interest expense on that debt. They are only going to devalue the currency in order to deal with that. Because if they don't, they're going to default, and it is going to be disastrous.

• 27:55Graham Stephan?

  How could you be wrong?

• 27:57Speaker 01

  If they stop printing money.

• 27:58Graham Stephan?

  Isn't there a chance? AI gets so advanced that we grow into the national debt. We become very efficient. We're able to scale back our spending. We're able to run a surplus. And all of a sudden, there's no need necessarily for Bitcoin because we got a digital dollar that's tracked and become, you know, Bitcoin just becomes obsolete. Now Bitcoin could become obsolete, but one thing that isn't going away is all of that [bleep] paperwork that you have to deal with when you run a business. You hire one [bleep] person. Hey, get over here, bro.

• 28:31Graham Stephan?

  Suddenly, there's onboarding forms, direct deposit, payroll taxes, all this [bleep] you do not want to deal with. All right, Jack, calm down. We know it's annoying, but that's why we use our partner, Gusto, to make payroll and taking care of our team a whole lot simpler.

• 28:44Jack Selby?

  In all seriousness, I've been using Gusto for years, and it's something that we trust with our own business. When we hired our editor, Michael, it helped us through the entire process. And now getting him paid through direct deposit is so simple.

• 28:54Graham Stephan?

  For those unaware, Gusto is an online payroll and benefit software that's built for small businesses. It's all-in-one, remote-friendly, and incredibly easy to use so you could pay, hire, onboard, and support your team from anywhere.

• 29:05Jack Selby?

  It also handles payroll tax filing automatically, so there is less administrative work to keep track of.

• 29:09Graham Stephan?

  And also, it's not just us. Like Gusto is trusted by over a half a million small businesses, and they are also ranked number one on G2's Highest Satisfaction Product List for 2026.

• 29:20Jack Selby?

  And if you're already using another system, switching is so incredibly simple. You just transfer over your existing data, and you do not pay a single cent until you run your first payroll.

• 29:28Graham Stephan?

  So try Gusto today at gusto.com/iced and get three months free when you run your first payroll. Again, that is three months of free payroll at gusto.com/iced.

• 29:37Jack Selby?

  One more time, that is gusto.com/iced, or just click the link down below in the description.

• 29:42Graham Stephan?

  But before you get to onboarding, there's finding the right person for the job. And that doesn't always mean hiring a full-time employee. Sometimes you just need an expert for one part of the business.

• 29:51Jack Selby?

  Whether you need a website built, help with marketing, or AI tools set up, our partner Upwork helps you find the person who can handle it.

• 29:57Graham Stephan?

  You could browse profiles, review past work, and get help defining the scope of the role so you could hire with confidence.

• 30:03Jack Selby?

  And with Business Plus, you can access the top 1% of talent on Upwork. AI-powered shortlisting gives you a curated shortlist of top freelancers matched to your goals in under six hours.

• 30:12Graham Stephan?

  And you could work with a freelancer on one project or keep them involved long-term. As your business changes, you could bring on more help or scale back.

• 30:19Jack Selby?

  And don't worry, you're not just taking a guess based off of a profile. Upwork has over 170,000 freelancers with five-star ratings so you can see feedback from businesses they have actually worked with.

• 30:29Graham Stephan?

  Plus, Upwork handles the contracts and payments in one place, which makes managing that relationship simpler, too.

• 30:35Jack Selby?

  So you can spend less time sorting out the logistics and more time working with an expert to get the project done.

• 30:40Graham Stephan?

  All you got to do is visit upwork.com/coffee right now and post your job for free.

• 30:45Jack Selby?

  That is upwork.com/coffee to connect with top talent ready to help your business grow.

• 30:49Graham Stephan?

  That's U.P.W.O.R.K. com/coffee. Upwork.com/coffee. Isn't there a chance? AI gets so advanced that we grow into the national debt. We become very efficient. We're able to scale back our spending. We're able to run a surplus. And all of a sudden, there's no need necessarily for Bitcoin because we got a digital dollar that's tracked and become, you know, Bitcoin just becomes obsolete at that point.

• 31:16Speaker 01

  I love you guys. I 100% believe that that's a possibility. I think it's a low possibility, but I think it's a possibility. I recently tweeted and I said, there's two assets you need for the future we're headed towards, Bitcoin and AI. Because if we are going to inflate our way out, I want Bitcoin. If we're going to grow our way out, I want AI. Those are the two options we have. We have a really bad, dire national financial situation, and we have two options: inflate or grow. I'm cool either way. Our public company owns probably one of the leading AI fintech products in the country in Sylvia. And if AI becomes a thing, we're going to do very well. If the government decides to keep printing money and flitting our way out, we're going to make money on Bitcoin. So it's kind of my way of saying like, I don't know what they're going to do.

• 32:00Speaker 01

  I think that they're going to keep printing money. But also I could see a world where like, I don't, we've never seen super intelligence, like, like true artificial, you know, super intelligence. That could show up tomorrow and all of a sudden like Elon's right, no one's working for money and like we're growing so fast.

• 32:14Graham Stephan?

  What's concerning to me, because I tend to agree with you on the premise of the government's going to keep printing money. But I remember 2021, 2022, there were some really smart people who were saying, it doesn't make sense to lock in, you know, a big mortgage and not get an arm. Because in the future, interest rates are going to be lower than where they are today. Inflation is going to be under control. And so I'm not going to lock in for 30, I'm going to lock in for five and even lower interest rates. Cause interest rates for sure will be lower. And then somehow they're substantially higher because inflation is back. And so it's like this certainty that it's like, oh man, I've been wrong so many times that you can't.

• 32:59Speaker 01

  I think that there's a, there's a couple of different nuances around inflation and interest rates are related, but different. So for example, I think that the current administration going into December of 2025, kind of had like the perfect situation. They had a high growth economy with relatively low inflation. And I think a lot of people were like, this is kind of a central banker's dream. Is you are getting the productivity growth from all the AI robotics, et cetera. And then you almost had this deflationary pressure coming from those same AI robotics, but also deportations were very deflationary. And I was probably one of the loudest proponents in the entire country that tariffs were going to be deflationary as well. And so if you have high growth and low inflation, you kind of don't want to do anything.

• 33:44Speaker 01

  Like just let that run because you're not destroying your currency and you're, can make up room on the debt. Now, I don't know this for sure, but my analysis is we went, we did the Venezuela thing. And when we got Maduro, there was a little bit of like, we got the hot hand. You know, if you remember, we dropped the, in Iran, the first time, like down like a little air conditioner tube or something. And we were all like, that sounds awesome. The military is like really skilled. And then we got Maduro and no one got, you know, on the American side. And we were like, wow. And it was kind of like feed the hot hand. And then we went and did the Iran thing. And then all of a sudden we're like, oh, we're in the Middle Eastern. That is much longer than we thought it was going to be. Iran was much more aggressive in their response.

• 34:25Speaker 01

  Gas prices spiked, like here comes the inflation, you know, warning again. Now, I have tried my best to talk nuance about inflation, gas and the Iran thing. My thought has been the longer the goes on, the more the inflation risk comes. But we are all underestimating how deflationary the AI stuff is. So it's a little bit of like, you can't just be like, Iran, high inflation. And I think that's kind of what we've seen where like inflation definitely ticked up, but it didn't skyrocket to five, six percent. It kind of went to like three and a half ish percent and it's kind of like hung out there. So it's elevated from where it was in December, but it is still not the explosive, like, you know, nine percent, obviously from COVID or something like that.

• 35:07Speaker 01

  With that said, I also think that people assign a lot of the inflation problem to Biden. And rightfully so, like he did contribute a lot to it. Definitely when we already had high inflation, they were still printing lots of money, et cetera. But I think that all throughout the 2010s and then definitely the COVID response under the Trump administration, like they all contributed to it. Republicans and Democrats. And so it's kind of this weird dynamic where like, we always want like, who's the culprit? But it's really all of them. Congress, Senate, President, Treasury, Fed, like they're all part of this. Because I think that an unspoken part of the problem is that the boomer generation doesn't want some things to get better. They are financially incentivized for things to continue how they are. So the example I always use is housing.

• 35:53Speaker 01

  If you're over the age of 60, you don't want house prices to go down in this country. You don't care that the 22 year old can't afford a home. You're like, dude, 60% of my net worth is tied up in my primary residence. I need this to keep going up. So the fact that these kids are like, I can't afford a home and I'm into socialism. They're like, oh, you guys are stupid. But if that 60 year old was 22, they'd be yelling and screaming and doing the same thing. It's just that they need their home price to keep going up or their net worth comes down. Trump himself has said this, we're not going to hurt the boomer home prices. So you get this weird dynamic of like, who are we serving? Are we serving the older people or we're serving the younger people? It's a hard decision.

• 36:34Graham Stephan?

  So when is the last time you bought Bitcoin in your personal portfolio?

• 36:37Speaker 01

  We have been buying more Bitcoin exposure through our public company. Basically, we've been able to buy back shares of the company to get everyone more exposure. I have a lot of ownership of the company. Personally, this year, I don't know the last date, but this year. And I kind of made a decision at some point, like I got the Bitcoin I got. And that position is a highly concentrated position. I need to go focus all my time, energy and effort on rebuilding an entirely second life, essentially financially. And so it's not that I lost any interest in Bitcoin or anything like that. It was just like, I kind of like did what I thought I needed to do. And then on the other side, it was like, let me go build a bunch of diversification over here.

• 37:18Graham Stephan?

  So if you're still buying Bitcoin, though broadly speaking, why are you selling Bitcoin also to then buy shares of your company?

• 37:27Speaker 01

  The public company that we have has an AI product called Sylvia, so Sylvia.com. And the way that that product works is you come in, you attach all your accounts and then you can start talking to an AI. We can talk about details of that. But as part of that business, we have a lot of Bitcoins sitting on the balance sheet, probably $400 million or so. The market currently, because Bitcoin had drawn down, Bitcoin went out of favor. All of the capital rotated to AI, people were investing in data centers and, you know, all the latest companies, whatever. So these Bitcoin companies started to trade for the most part below the value of the Bitcoin. So if we had $400 million of Bitcoin, then it would trade at 250, 300 million dollars of value. So if Finance 101 would tell you, if your stock is trading below the cash on your balance sheet or the liquid assets of your balance sheet,

• 38:09Speaker 01

  you should take those assets and buy back your shares because you're basically using $1 to buy 70 cents. And so that's what we've been doing. Now, when you do that, the shareholders of the company that remain, they own more Bitcoin at the end of that transaction. So it was a very accretive type of transaction. And if all of a sudden the stock started to trade above the Bitcoin value, we have a decision to make. How much value do we ascribe to our AI business? And if you had the AI business plus the Bitcoin, if we're trading above that, then Finance 101 would tell you, well, you should be selling your shares. You should be raising capital because the market is valuing more than you think you're worth. So when you're trading too high, you want to be raising capital because it's less dilutive.

• 38:51Speaker 01

  When you're trading too low, you want to be buying back shares because you're basically increasing your ownership of the business.

• 38:55Graham Stephan?

  So why would I buy Bitcoin right now instead of just buying discounted Bitcoin by buying BRR?

• 39:02Speaker 01

  Well, it depends on who you are. If you have no Bitcoin exposure, what I always tell people is for years I've said, get off zero. Just if you have 0% exposure, buy $5 of Bitcoin. The second you buy any amount, you start to pay attention to it. That's how I learned, right? Was I started reading, learning, paying attention. If you don't own Bitcoin directly, then that's kind of your entry place. Is you should go and buy some Bitcoin directly. You should figure out how it works. One of the things I usually tell people is you should move it between wallets. You should send it to someone, get it sent back, right? Figure out how does Bitcoin work so you know what you own. Once you have Bitcoin exposure directly, then you can kind of move to level 201 or 301. Now, if you buy our company or any other company that owns Bitcoin on its balance sheet and we are trading below the Bitcoin value,

• 39:48Speaker 01

  there's still execution risk. We don't have a profitable company. So you have to start to calculate, okay, well, how long is it going to take them to get profitable? How much cash could they potentially burn till then? Like that is a much more advanced analysis than simply just buying Bitcoin.

• 40:01Graham Stephan?

  And so you sold Bitcoin in order to buy more of your company?

• 40:05Speaker 01

  Which increased the ownership of Bitcoin for everyone at the company, correct?

• 40:08Graham Stephan?

  When do these funds fail? Is there a chance that somehow the fund goes out of business?

• 40:15Speaker 01

  So any company that is in the public markets basically has regulatory risk, execution risk, financing risk. I mean, it's just like any other business, just there's more scrutiny, there's more oversight, there's more costs associated with the public company.

• 40:28Speaker 01

  In our case, I speak to our, we have hundreds of millions of dollars on our balance sheet from Bitcoin and cash. And we have a relatively small team. We have less than 15 people or so that work at the company. We have an AI product that we have a lot of conviction in and we think is going to grow very quickly. But if for some reason, all of a sudden costs exploded and we were using the balance sheet to fund those losses and we just bled out the balance sheet, we would have no money. Now, at the current burn rate, we have like, I forget the latest numbers, but something like, you know, 15 or 20 years of runway. So it's a significant amount of time and that's without Bitcoin increasing in price or kind of anything happening. So you have basically a well-funded public company with this AI product.

• 41:10Speaker 01

  If we did not have the AI product, then you would basically look at the Bitcoin and you'd say, well, if Bitcoin goes to zero, the. Company is going to go to zero, right? Or is at least it's going to lose a lot of value? If the team makes bad decisions in capital allocation, then you have the potential to make a lot of errors. So for example, if you're selling the Bitcoin to buy back more shares, but your shares are trading at too high of a price, the reverse is happening, right? You're actually like losing value, but ultimately comes back to, if a company just has Bitcoin on its balance sheet, as long as they don't take out enormous amount of debt or do something from a capital markets perspective that is stupid, they just have to wait. Now, the question for a lot of people, I think, who are investing in just pure play, public company with Bitcoin on the balance sheet, no AI product, no anything, is your question earlier, Jack of should I buy Bitcoin or should I buy this thing?

• 41:55Speaker 01

  And it's so case by case, depending on what is the discount, what is your sophistication level, et cetera? It's nearly impossible for me to, you know, kind of tell them what they should do.

• 42:04Graham Stephan?

  What do you think the chances are as a percentage that Bitcoin goes to zero?

• 42:08Speaker 01

  Less than 1%.

• 42:09Graham Stephan?

  What makes you so confident that it's that low?

• 42:12Speaker 01

  Lindy effect. The longer that something exists, the higher the probability that it exists in the future. What is the difference between the life of Bitcoin and the life of the current US dollar? The current US dollar has been around for ballpark 55 years. Bitcoin has been around for ballpark about 17 years. To somebody who is 18 years old or younger in the United States, that's the same thing. Their entire life Bitcoin and the current version of the US dollar have been around their whole life.

• 42:44Graham Stephan?

  What's the strongest argument you have against Bitcoin?

• 42:47Speaker 01

  If they stop printing money.

• 42:48Jack Selby?

  And what do you think could happen to the price of Bitcoin if they stop printing money?

• 42:51Speaker 01

  It would go down.

• 42:52Jack Selby?

  I think that-

• 42:52Speaker 00

  Down, but like down is, you know.

• 42:55Speaker 01

  How much, you know, can they actually get to a balance? But if all of a sudden they were like, not only we're not going to print any money, but actually like, we're going to get into this super deflationary environment and Bitcoin is going to fall 30%. Okay. Well, like if we have a lot of deflation like that, it's definitely what could happen. If you go back and you look, why did Bitcoin go down in October of last year? Bitcoin was the canary in the coal mine. We started to see inflation really start to fall aggressively in the second half of last year. And Bitcoin being the most sensitive, right? Started to really lead all of the other assets. We eventually got stocks and everything kind of turned over there for a while. But it goes back to like, if that was a prolonged thing where we had like true deflation, Bitcoin would go down. So would tech stocks. So would other things that are sensitive to money printing, right?

• 43:40Speaker 01

  And so it comes back to this weird thing of, I don't think a lot of investors want to think of inflation and deflation and interest rates and, and, uh, you know, kind of all these like nuanced economic details. What they really care about is like, how do I just put my finances kind of on like autopilot? And what I always tell people is right now you have a brokerage account, you have a checking account and you've got a savings account. I look at stable coins as the equivalent of your checking account. That's the money you use to buy things, et cetera, in the digital world. I look at Bitcoin as your savings account. You put your money in your savings account in the traditional world, you're not supposed to touch it. Put six months in a rainy day fund, leave it there, don't touch it. Go in your brokerage account, go in your checking account, like that's the money that you use on a day to day basis. Don't touch your savings.

• 44:23Speaker 01

  In the digital world, I think that there's tokenization and like all this stuff happening on brokerage. I think stable coins are the checking account, but I just think Bitcoin is a savings account. Put your money in there, don't think about it, don't count on it, right? So don't go put 90% of your money in, uh, in Bitcoin. Put whatever percent, you know, 10%, whatever, whatever the number is that you want to put in Bitcoin, whatever is the right thing for you. And then don't think about it and go spend your time productively, trying to create value at your job or building a business. And I think you'll end up pretty well.

• 44:50Jack Selby?

  I could probably have more Bitcoin than 1%.

• 44:54Speaker 00

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50 page restoration blog, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up require compatibility and availability varies 18 plus.

• 45:19Jack Selby?

  I, I have-

• 45:20Speaker 01

  What are you scared of?

• 45:21Graham Stephan?

  You wouldn't be buying at a bad time, relatively speaking, hopefully.

• 45:25Jack Selby?

  Relative to someone that I know. Yeah.

• 45:28Graham Stephan?

  Well, it'd been dollar cost everything, so you gotta, you gotta take the highs and lows.

• 45:32Speaker 01

  Let me ask this question. Why do you only have 1% right now? Like, is there a reason that you're worried about?

• 45:36Jack Selby?

  Yeah, I happened to buy a lot of iBit, uh, like when it was like 110,000 and then it just kept going down and down and down and down and down and down. And I had a bunch of margin on the account. At the time, I'm like, you know what? If I'm going to prune anything, then it's the thing that doesn't really have a business backing it. And so I'm going to sell, you know, my iBit.

• 45:55Speaker 01

  You know what's interesting? He kind of looks like Vitaly from that angle.

• 45:58Graham Stephan?

  You know what? You know Vitaly?

• 46:00Jack Selby?

  And he looks like Chris Camillo. Yes. It's the face that you do when you kind of like, like this, like this.

• 46:06Graham Stephan?

  Yeah.

• 46:07Jack Selby?

  You look just like Chris Camillo when you do that.

• 46:10Graham Stephan?

  You had the glasses.

• 46:11Jack Selby?

  Dude, that's hilarious.

• 46:12Graham Stephan?

  If you had the glasses, the Chris Camillo glasses with a, with a deeper voice.

• 46:16Jack Selby?

  Yeah.

• 46:17Speaker 01

  They both all of a sudden, your two faces changed.

• 46:20Graham Stephan?

  Because I, I've been noticing-

• 46:22Jack Selby?

  Yeah, it's when he does that kind of like, like that kind of face, you look just like Chris Camillo.

• 46:25Speaker 01

  Which face?

• 46:26Jack Selby?

  It's like a, like a, that kind.

• 46:30Jack Selby?

  I don't really know, but it's when you're kind of explaining something, I just see Chris Camillo doing that exactly.

• 46:34Speaker 01

  Well, he's a good investor, so I'm cool.

• 46:35Jack Selby?

  He's a great investor. And then from the side, you almost look like Vitaly.

• 46:39Speaker 01

  Who is Vitaly?

• 46:40Jack Selby?

  Vitaly ZDTV.

• 46:42Speaker 01

  Yeah. Oh, he's the guy who like goes and like surprises.

• 46:44Jack Selby?

  He's a prankster. Yeah. It's funny. Yeah.

• 46:47Graham Stephan?

  I like them both.

• 46:47Jack Selby?

  Yeah. Yeah. Yeah. Vitaly, we'd love to have you on the podcast, by the way, and Fuzi. But anyways, that's, all right, go ahead. I would love to know, in one sentence, what is your strongest argument for Bitcoin?

• 46:59Speaker 01

  They will never, ever stop printing money. If they never stop printing money, the dollar loses value. If you hold cash as a saver, they will ruin your financial health. If you hold investment assets, when they do that, they will enrich you. The asset that will benefit the most from dollar printing is Bitcoin.

• 47:15Jack Selby?

  And why Bitcoin as opposed to other assets?

• 47:17Speaker 01

  Cause it's the most sensitive to money printing.

• 47:19Jack Selby?

  So why is it the most sensitive?

• 47:20Speaker 01

  Because it is a digital scarce decentralized asset that when people see money printing, the first asset they go buy is Bitcoin. Recently, Scott Best of the Treasury Secretary said, we're going to double the amount of purchases of long dated treasuries. Within seconds of him saying that Bitcoin immediately jumped about $5,000. Gold went up, lagged, stocks went up, lagged. But the asset that is most sensitive, that moves first and that moves the most violently on that announcement is Bitcoin.

• 47:52Jack Selby?

  And why Bitcoin instead of Ethereum, instead of Dogecoin, instead of a laptop coin? How do you know Bitcoin is the one?

• 48:00Speaker 01

  Well, Bitcoin is very unique. It is the only one that is digital, decentralized, non-sovereign, and has proof of work. All of the other coins have some different version. The reason why they were created was because they wanted to do something different than Bitcoin. They may use a blockchain, but then they have proof of stake or they have some twist to it. But ultimately, the thing that Bitcoin was built for is to insulate yourself from the money printing. Bitcoin was built specifically to insulate people from the money printing. In the initial-

• 48:31Jack Selby?

  How do you know that?

• 48:32Speaker 01

  In the initial launch, it talks about money printing and central banking. In the white paper, it talks about this. Satoshi talked about it at nauseam, how the role of a central banker is to not debase the currency, yet there are histories littered with violations of that trust.

• 48:49Jack Selby?

  If you were to take one guess at who Satoshi is, who would you say?

• 48:53Speaker 01

  You.

• 48:54Jack Selby?

  How did you know?

• 48:57Speaker 01

  First, I don't want to know who Satoshi is. I think that a lot of Bitcoin's value is ascribed to the fact that nobody knows who Satoshi is. It's very hard to critique the founder or the creator of Bitcoin because we don't know. My guess is that Satoshi is, uh, no longer alive. My guess is that Satoshi was one of the four or five people that was probably involved early on. My wife has a great theory that Satoshi was a woman because she says that no man could create Bitcoin and keep his mouth shut. And so she thinks that it has to be a woman. Peter Thiel has a very interesting theory. Peter believes that Satoshi and the late 1990s, there was a, uh, conference in Antigua where there was a bunch of cryptography folks and a bunch of like payment and finance folks.

• 49:41Speaker 01

  And they were all on this island, it was about 250 people, I believe. He thinks that Satoshi was probably there.

• 49:46Graham Stephan?

  On the island.

• 49:47Speaker 01

  I don't know if that's true or not. I wasn't there.

• 49:48Graham Stephan?

  We don't like islands.

• 49:49Speaker 01

  No. Yeah, um, for a good reason. Yeah.

• 49:52Graham Stephan?

  Connection. Yeah. So what happened with the Crypto Clarity Act?

• 49:55Speaker 01

  The Clarity Act is quite funny to me because everyone is so worried about will it get passed or will it not? I continue to say that Bitcoin doesn't need the Clarity Act because Bitcoin already has clarity. It's legal in the United States. There's a regulatory framework that oversees it. And no one is worried about any sort of regulatory issues with Bitcoin.

• 50:10Graham Stephan?

  I thought the regulatory is such a gray area between the SEC and the Consumer Financial Protection Bureau.

• 50:18Speaker 01

  The SEC and CFTC have actually signed agreements that they are fully on board, same page, same team in working with that. That's new for this administration. The past administration, that was not the case. There was quite a bit of infighting. But the Clarity Act is ultimately not really making a judgment on individual cryptos or even the technology itself. What the Clarity Act really is doing, if you boil it down, is it's saying who can benefit or who can profit from this industry. So you have a bunch of crypto companies who would like to take on the large financial institutions, the banks, et cetera. And you have the banks who are saying, wait a minute, we don't want them to get a piece of the profits. And so you have these two groups that are basically fighting with each other. The banks would argue, well, if you have stable coins and deposits and you're paying interest, you're a bank. So you should get regulated like a bank. You should go get a banking license.

• 51:00Speaker 01

  The crypto companies would say, well, the stable coins are something different and we're paying rewards, we're not paying interest. And that is ultimately the debate. It's not so much, are we going to have stable coins? Are we going to have Bitcoin? It is who is going to have the regulatory right to profit and serve the customer. I personally am of the belief that the government shouldn't be in the business of picking winners and losers. We should let the free market figure it out. So let as many people compete as possible and then allow the free market to determine who the winner is. But there's a lot of people in Washington DC with a lot of different interests. And I think that there's a lot of companies that are all jockeying for what the exact language is, and they all have a lot of money. And so whenever you throw a lot of interest, a lot of money and a lot of companies all at a problem, you kind of get what we got, which is like essentially a stalemate.

• 51:44Speaker 01

  No one can agree on anything. And so it just kind of peters long sideways.

• 51:48Graham Stephan?

  Are there any other regulatory risks that you see in the near future?

• 51:52Speaker 01

  With Bitcoin, no. I do think there's still quite a number of questions around, uh, for example, there's a new project called Hyperliquid, which is essentially trying to tokenize a lot of kind of nuanced types of assets. Should that be allowed in the United States? How should it be allowed? Who should be able to participate? Where do those profits go? What are their guardrails? All of that stuff is above my pay grade. I really spend my time focused on Bitcoin in particular, and I think that the regulatory, you know, apparatus and, um, oversight of Bitcoin is very clear. And so Bitcoin doesn't need the Clarity Act because Bitcoin already has clarity. And so I think that Bitcoin's in a great position there.

• 52:26Graham Stephan?

  How much have ETFs distorted the Bitcoin market? Because a lot of people now say that the four year Bitcoin cycle, it doesn't really matter anymore because ETFs have commoditized this to such a high degree. And now there's leverage on top of that, that like, everything at this point is kind of balanced out.

• 52:42Speaker 01

  The ETFs to me are not the coal- Of positive or negative impact to the Bitcoin market. The ETFs empowered the Wall Street kind of crowd to participate in Bitcoin. Because historically, if you wanted to participate in Bitcoin, you had to go and get a Coinbase account or figure out, you know, what you, how you were going to get Bitcoin or what you were going to trade Bitcoin. When the ETFs got created, it was now a very easy thing for them to buy. That was already approved on their platform that they understood and it was a rapper that they liked. And so now you basically opened up who can participate in Bitcoin in a significant way. Now be careful what you wish for is something that I tweeted many, many times, leading up to the ETF approval. Because these individuals, they are not hardcore Bitcoiners. They are hardcore capitalists.

• 53:27Speaker 01

  And so that means that they may want to go long Bitcoin. They may want to go short Bitcoin. They may want to be hedged to Bitcoin. They may want to do some sort of intricate trade with Bitcoin. They may want to put leverage on top of it. All of these things take Bitcoin from a thing that was kind of a pure asset. Used to not even be able to short Bitcoin. It was a long only asset that people just bought and of course it went up. But when you start to introduce all of these financial instruments, what you're doing is you're tampering the volatility. And you can see it in the numbers. Bitcoin went from an 80-ball asset to a 40-ball asset. So if you tamper that volatility, that means Bitcoin is not going to go up as much in the bull markets, but it's also not going to go down as much in the bear market. So Bitcoin used to draw down at 85%. Now it drew down about 50, 55%. What that tells me is if that was the bottom, which I believe it was, Bitcoin is not going to go up 2,000% in the next bull market.

• 54:13Speaker 01

  It is likely to appreciate in a significant way, but it's going to have tampered volatility. And I think that there's a lot of people in the Wall Street world who like that. Bitcoin's volatility shrinking makes it more attractive to them. Because they don't want to buy an 80-ball asset. But they love a 40-ball asset because it's more volatile than other things in their portfolio. But it's not so crazy that they think it's too risky.

• 54:33Graham Stephan?

  What do you think about buying Bitcoin itself versus the ETF? I am personally a fan of the ETF. I only buy the ETF anymore. Buying Bitcoin itself was such a pain. I recently had to find my cost basis from Bitcoin back from 2017. And I printed out records.

• 54:53Speaker 01

  Wait, why did you have to find that?

• 54:55Graham Stephan?

  Because I claimed a loss from Celsius and they paid me back Bitcoin. But I had to find my original cost basis to determine if I made money on the Bitcoin or I lost. And there was some sort of a gain, but I had to prove to the IRS where I bought the Bitcoin at, at the average price. So I, you had to track every single purchase. And it's not just as easy as like tracking it. It was horrible, horrible, hours upon hours of research.

• 55:27Speaker 01

  The exchanges also, for a long time, were not required to give certain filings or kind of issue the equivalent of like a K1, but for an exchange. They now have to do that from a regulatory or tax purpose. In terms of Bitcoin versus the ETF, Bitcoin is kind of the pure play exposure to the asset. But there's challenges. You have to figure out how to custody it. You have to figure out how to measure. Am I up, am I down with my cost basis, all these different things. The ETF, the reason why people like ETF wrappers is because it's easy. I'm willing to pay 10, 20, 25 basis points for somebody else to deal with a bunch of this stuff. So somebody is doing work for you. You're paying that management fee. For the S and P 500, it's really simple. You pay eight basis points, give or take, and they handle everything for you.

• 56:12Speaker 01

  They buy 500 stocks, they do the rebalancing, they do everything that they're supposed to do. If you were to go and buy the 500 stocks yourself, that would be pretty painful. And so what do people do? They're willing to buy the ETF because it's easy, there's convenience. I think the same thing with Bitcoin ETFs. There are some people who couldn't buy Bitcoin, but for the average person, they find it easier. They think it's more secure. They think that they have better access to information. And frankly, I think that they give them peace of mind in many cases. One of the things that Bitcoin needs to make sure is that it preserves the Bitcoin ethos and what I would call the Bitcoin values of self-custody, decentralization, sovereignty. But at the same time, we need to expand access to Bitcoin and the ETFs have done a great job of doing that too.

• 56:51Jack Selby?

  So if I'm going to buy some Bitcoin, where should I buy it?

• 56:54Speaker 01

  If you're going to buy actual Bitcoin, I would use one of the top American brand exchanges. If you're outside of the United States, then I would use, you know, one of the top global exchanges. I do not think that buying cryptocurrency in general is somewhere where you want to take a risk on a no-name company. And you can see it in, if you plot out, what are all the things that they use to induce you to use an exchange that you haven't heard of before? The more that they offer, they're doing that because you're taking more risk. So if you look at Coinbase, Coinbase is like, you can sign up for an account. Maybe every once in a while, they run some sort of, you know, offer, hey, we'll give you, we'll give you 50 bucks if you open an account or something.

• 57:35Speaker 01

  There are crypto exchanges that used to offer like, we'll give you $10,000 or, you know, some crazy offer. And a lot of people would do it. But the reason why they did that is because they had to get people comfortable with opening an account on an exchange that they never heard of before. So I think that when you're first starting, just go to the things that people know, have trusted. 100 plus million people, I think, use Coinbase now. I think that there's a couple of other American exchanges that are, are pretty.

• 57:59Jack Selby?

  So where do you buy Bitcoin?

• 58:02Graham Stephan?

  You can't say?

• 58:03Speaker 01

  I don't want to talk about security either.

• 58:05Graham Stephan?

  It could, I, I think it's probably private transactions. Cause when you buy a significant amount, a lot of them, private transactions. Or it's also you give away the exchange, the brokerage. And then you kind of know where to sneak around. But overall though, how do wealthy Bitcoiners actually lose their Bitcoin?

• 58:25Speaker 01

  Well, there's definitely security issues. I would say that most people I know who have ever lost Bitcoin, one of two things have happened. They have trusted a custody provider or some sort of company and that company has gone bankrupt. And so Celsius, you know, there's FTX, a bunch of these guys. Or there is some sort of hacking. Now the hacking can be SIM swapping and more kind of technical things. Or it could be as simple as some sort of social engineering. And so what I always tell folks is if you are going to self-custody your Bitcoin, again, you want to make sure that you create a number of different security protocols so that you are not susceptible to those things. How individual people do that is kind of up to their technical abilities or what their, you know, kind of risk profile looks like.

• 59:09Speaker 01

  But I think that generally, if you're like an average, down the fairway person who's like, I want to put 1% of my assets in Bitcoin. You should buy a little bit of Bitcoin so you learn about it, use it, move it, et cetera. But most of those people are going to end up just buying an ETF. Could quantum computing hack Bitcoin? Quantum computing could hack the banks, could hack the military, could hack the nuclear codes. It could do lots of things. If a quantum computer got to the point where it actually was effective. Today, I think that there's a lot of debate as to what is the current state of quantum technology? And there are, like many industries that are early, new and promising. Lots of hype, lots of, hey, this is what's going to be possible. But if you actually look at like, where are we today?

• 59:52Speaker 01

  I think that most people who are rational say, it's interesting. Let's see where it goes. And so today, I don't think quantum can hack bank accounts, cryptography, Bitcoin, national secrets, et cetera. I think what a lot of people are paying attention to is if quantum continues to advance at a fast rate, then we are going to have to figure out how exactly does Bitcoin and all cryptographic systems upgrade to make sure that they're quantum resistant.

• 1:00:16Graham Stephan?

  Speaking of safety, what is the safest way for someone to hold $10,000 of Bitcoin, 100,000, a million and $10 million?

• 1:00:25Jack Selby?

  Whether you're holding $10,000 or 10 million, you want to trust the platform that you're using. And the same can be said about running an online business, especially as we're heading into Black Friday.

• 1:00:34Graham Stephan?

  Yes, you want your store ready and your checkout running smoothly when customers show up, which is why we used our partner Shopify to sell our Iced Coffee Hour hats.

• 1:00:42Jack Selby?

  Shopify makes setting up an online store super easy. You can get up and running and start selling in just a few steps without needing to be an e-commerce expert.

• 1:00:49Graham Stephan?

  Plus Sidekick, which is Shopify's AI assistant, can help you with everything from setting up your store to planning promotions. So you're ready before the holiday rush.

• 1:00:57Jack Selby?

  Exactly. Timing matters. Black Friday is when more people are already shopping and ready to buy. So if you launch now, you get to take advantage of all of the extra online traffic.

• 1:01:05Graham Stephan?

  So if you're ready to launch your business before Black Friday, just go to Shopify.com/ICH to start your free trial.

• 1:01:11Jack Selby?

  That is Shopify.com/ICH.

• 1:01:13Graham Stephan?

  Go to Shopify.com/ICH today to hear your first. Speaking of safety, what is the safest way for someone to hold $10,000 of Bitcoin, 100,000, a million and $10 million?

• 1:01:28Speaker 01

  If you simply are optimizing for security, you're not worried about sovereignty. Control anything else than putting it with the ETF is probably the single safest thing. It is the least inexpensive. It has insurance. If somebody was to take your stock shares, they can be reissued. So that is like from a pure safety standpoint, the ETF. But there's trade offs. There's a lot of people who say, well, I don't actually own Bitcoin. I own a claim on Bitcoin via the ETF. I worry about, you know, a multitude of other things in doing that. But if you're just optimizing for security, probably the ETF is the single most secure thing for people to do.

• 1:02:03Graham Stephan?

  Why not a ledger trezer, holding it on something like Robin Hood?

• 1:02:08Speaker 01

  I think that all of those are good options, depending on who you are, how much Bitcoin you have. But if you look at the hardware wallets as an example, I think they do a fantastic job of securing Bitcoin. I think that they are very much trying to educate more people on how self custody works, how do their products work? But those are to me, kind of 201, 301 level products. The first Bitcoin you buy, take it and move it to a hardware wallet, move it to a software wallet, put it onto an exchange, take it off, put it into another exchange, take it into a hardware wallet. Moving Bitcoin around, I think is really effective. But I do think that the Bitcoin community overestimates the average person's attention span and technical ability to learn self custody versus the convenience of, well, I'm already in my brokerage account.

• 1:02:53Speaker 01

  Rather than me wire money out and put it somewhere else to go buy Bitcoin, I'll just buy the stock that gives me Bitcoin exposure as the ETF.

• 1:02:59Graham Stephan?

  See, I spoke with someone recently who was saying that they keep all of it on a, like an external wallet. And I said, man, it's so much easier to just buy the ETF. And they said, well, listen, imagine we go through something catastrophic. I like to be able to take this little device and I could go anywhere with it and it fits in my pocket. And I could go anywhere in the world with, let's just, I'm just making up a number, $10 million and it's mine. And I could plug this in across the other side of the world and I got 10 million bucks instantly. So if anything happens, this is here. Makes sense to me. But it's, you know, you're, you're banking for the worst, basically, that you would need that.

• 1:03:40Speaker 01

  Bitcoin is one of the only assets in the world that can do that. I think it is an incredibly valuable aspect of Bitcoin. The average person is not worried about that scenario. Maybe they should be. But the average person is trying to solve their problems in front of their face. And for the average person, they have zero or 1% allocation to Bitcoin and they're saying, how do I buy more? Not, how do I prepare for the electrical grid to go down, my government to fail and people to show up to my house? And so I think that it again goes back to Bitcoin is a teaching tool, in my opinion. As you start to learn about Bitcoin, you learn about the world. I credit Bitcoin with teaching me things about geopolitics, about national defense, about monetary policy. And so as you kind of go down this rabbit hole, you start to learn about all these things.

• 1:04:25Speaker 01

  And then all of a sudden you're like, oh, well, what would I do if the electrical grid went down? What would I do if I was in XYZ situation? But to the average person, they're scrolling on Instagram or Tik Tok, they're drinking Starbucks, and they're worried about what are they going to do on Friday night? And oh, by the way, maybe I should become an investor. Like I've listened to this podcast. It's pretty cool. What, what, you know, what do I do? That person is so far removed from like what happens if the grid fails, that they're literally like, should I buy a stock or should I buy some Bitcoin? How do I open an account? Where do I go? What's an ETF? If that's the average person, like there's a big gap between that and like $10 million of Bitcoin on a ledger that you're running around the world as a fugitive with.

• 1:05:07Speaker 01

  Which by the way, John McAfee was doing, and I went onto his boat in the Bahamas when he was a fugitive.

• 1:05:13Graham Stephan?

  What year was this?

• 1:05:14Speaker 01

  Probably 2019, I think.

• 1:05:16Graham Stephan?

  How'd you get invited on his boat?

• 1:05:18Speaker 01

  I messaged him. I said, John, it looks like you are somewhere in the Western hemisphere. I want to do a podcast with you. Where are you going to be next? And he kept posting these pictures and it looked like he was somewhere like in the Caribbean. And I was willing to go anywhere in the world. I really thought it would be a fascinating conversation. And he introduced me to his wife and she said, we're going to be in the Bahamas in two days. Meet us there. Okay. I turned to my brother. So you want to go? He said, yep. Got flights, flew there. They gave us an address and we showed up. And they were parked in a, on a dock and there's a bunch of boats there. And John was on his boat. He was still hungover from the night before. He'd completely lost his voice,

• 1:06:01Speaker 01

  which is not good if you're trying to do a podcast. And there was everywhere. Like not one, not three, not five, like 100 all over the boat. And I was very nervous because I said, you don't look sober. You have a reputation for being a little volatile. There may or may not be a rumor that you might have potentially your neighbor. And now there's everywhere. So we expertly tried to navigate the situation to do an interview with John with all over the boat and not touch any of them, nor upset him in a way that could potentially put ourselves in danger. He turned out to be the nicest guy in the world. He was incredibly accommodative. He did the interview. It was hilarious. He had incredible insights. He's very intelligent.

• 1:06:47Speaker 01

  And at the very end, he was like, thank you so much for coming. Do you want to take a picture together? Well, of course I do. And so then he tried to hand me multiple. After I politely refused, I have a picture with John McAfee where him and his wife are holding, and I'm standing there.

• 1:07:00Graham Stephan?

  Why wouldn't you grab a?

• 1:07:01Speaker 01

  I don't want my fingerprints on the gun.

• 1:07:03Graham Stephan?

  Yeah, but there's photo evidence that like, you know, you just did it for a photo.

• 1:07:07Speaker 01

  Maybe. I wasn't going to take that chance.

• 1:07:09Graham Stephan?

  But it's John McAfee. I don't know. That's a.

• 1:07:11Speaker 01

  It was an amazing life experience.

• 1:07:13Graham Stephan?

  You could AI yourself now holding a.

• 1:07:15Speaker 01

  In hindsight, I probably should have been more worried about being on a boat with a fugitive of the US government in the Bahamas with. But I was not thinking about that at the time. I was there as maybe a pseudo journalist. And it was awesome. I learned a lot and found him incredibly engaging, but was not a scene where I was like, this guy's probably going to be around for a long time.

• 1:07:37Graham Stephan?

  What's the most valuable lesson you learned from John McAfee?

• 1:07:40Speaker 01

  I think there's three things. I don't think he really cared when anybody else thought. I think that he embodied the idea of having no fear. And I think that he was much more intelligent because he questioned everything around him. And so people took that as like, he's a conspiracy theorist. But I think he had a pretty rational view as to, I'm being told a piece of information. Is this true? How do I know? What evidence can I go find? It was almost like applying the scientific method to information that he received. And so in conversation with him, you go in expecting kind of a wild, crazy fugitive man that has lost his mind and is kind of close to his death. Instead, I found somebody who definitely drank a lot, who definitely partied a lot, but also was still incredibly sharp. And it was very obvious why he had built such a big business.

• 1:08:22Graham Stephan?

  Going back to the price of Bitcoin, how manipulated is the price?

• 1:08:26Speaker 01

  You'd have to ask the manipulators. I don't know. It's very hard to tell. Bitcoin goes up, it goes down, the stock market goes up, the stock market goes down. So a good maybe counter argument would be, is Bitcoin more or less manipulated in the stock market?

• 1:08:39Graham Stephan?

  More.

• 1:08:40Speaker 01

  Maybe.

• 1:08:41Graham Stephan?

  I don't think it's a maybe. I mean, we see the price like shoot up like 2% instantly. And then it immediately just like crashes 3% and then it goes back to normal. There's something going on there.

• 1:08:51Speaker 01

  Well, is that manipulation or is that just a lack of sophistication in people who are buying Bitcoin? Because you don't have kind of the traditional channels buying it. So for example, if I go to a large bank and I say, hey, I would like to buy $20 million of a stock. They will VWAP it over some period of time. They will be intentional about how do I acquire this stock without moving the price? And they're very good at doing this. They have years and years of experience. They have entire teams. They have technology, et cetera. There are people in the Bitcoin world who are just like, I want $20 million of Bitcoin. And they'll just press the button and all of a sudden it'll shoot up and it'll come right back down. And it wasn't manipulation. It was kind of lack of sophistication. So whenever I see this stuff, I always say to myself, is there manipulation?

• 1:09:33Speaker 01

  Well, financial instruments, leverage, all of these things can definitely manipulate price. I tend to be like an Occam's razor, like the most likely explanation is the simplest, which is like just people are not as sophisticated in the Bitcoin world as they are in the traditional finance world.

• 1:09:46Graham Stephan?

  What do you think about meme coins?

• 1:09:48Speaker 01

  Would you buy them?

• 1:09:49Jack Selby?

  The best investment I have ever had is Dogecoin.

• 1:09:51Speaker 01

  So if you were to channel Howard Marks, Howard Marks would tell you that that is a dumb idea. Because if it is potentially your best investment ever, it means you had to take enough risk where it could have been your worst investment ever. So Howard Marks' entire strategy is necessarily true.

• 1:10:06Jack Selby?

  Yeah, it's best in terms reflected as a percentage, not in terms of gross amounts.

• 1:10:10Speaker 01

  No, no. Howard Marks' entire view on taking risk and driving returns is you should never want to be the number one asset manager in a given year based on your return, because that meant that you had to take so much risk to drive that return. That if you had been wrong, you would end up being one of the worst asset managers that year. So instead, what Howard Marks believes and his strategy has been for decades is he simply wants to be above average. And if he's consistently above average decade after decade, then he ends up being one of the top five asset managers of all time. Because he basically, everyone else took so much risk and blew themselves up.

• 1:10:41Jack Selby?

  Dogecoin is kind of the same thing. Has Howard Marks ever turned $100 into $16,000 in Dogecoin?

• 1:10:45Speaker 01

  Howard Marks turned $100 into way more than $16,000 in his life.

• 1:10:49Jack Selby?

  In Dogecoin?

• 1:10:50Speaker 01

  Not in Dogecoin. I don't, Howard Marks was not interested in Bitcoin, nor Dogecoin. Howard Marks has a, has a son who is incredibly intelligent. I've had the pleasure of, of meeting and talking to. And one of the nice things that I think a lot of these legends of finance or legendary investors, they understand when their mind is becoming like concrete. It's no longer wet cement. And so they tend to then say to a young person who either on their team, a family member, et cetera, like, why don't you take the risk? One of my favorite stories in finance is Stanley Druckenmiller was the head of research at a firm. And he was like 32 years old and the head of the firm came to him and said, Stan, you're going to be in charge of the investment team now. And Stanley was shocked because he was like, well, there's a bunch of guys who are older and more senior than me.

• 1:11:33Speaker 01

  Why are you not putting them in charge of the investment team? And the guy said to him, he goes, because they all lived through the bear market. They're going to be scared of taking risk. And right now we're heading into a bull market and we need basically somebody young and dumb enough to just take max risk. And so you're going to be in charge. And Stan has told the story in public before, but basically what he describes is like, that's sometimes why we send 17, 18 year olds on the front lines of the army. Is that are almost like oblivious to the risk that they're taking. The guy who is 35 years old, you know, there's saying be scared of the old man and a young man's game. Same thing kind of in finance is like the guy who's lived through multiple bear markets is much less likely to take just ungoverned risk. You probably were ready to take on governed risk in Dogecoin.

• 1:12:18Jack Selby?

  It was a hundred bucks.

• 1:12:18Graham Stephan?

  Yeah, that was a hundred dollars.

• 1:12:20Jack Selby?

  Yeah. And actually, I mean, it turned into like fifteen.

• 1:12:22Speaker 01

  So you were risk mitigating.

• 1:12:24Jack Selby?

  Yeah, whatever that was, I think it was a Reddit thing. And I was like, a hundred bucks, Graham, you tried it too.

• 1:12:29Graham Stephan?

  Oh, gosh, I hate this.

• 1:12:31Speaker 01

  Oh, he now admits that he has a Dogecoin.

• 1:12:33Graham Stephan?

  No, what happened is that Jack is a joke, told me to buy a thousand dollars of Dogecoin in 2020. And it was a fraction of a penny of like point zero to like, you know, of a penny like. And I got, I think it was 230,000 Dogecoin.

• 1:12:51Speaker 01

  Okay.

• 1:12:52Graham Stephan?

  And I thought it was dumb and the next day I sold it.

• 1:12:55Speaker 01

  And where did it go to?

• 1:12:56Graham Stephan?

  At the peak, that would have been worth about a hundred and forty thousand dollars from a thousand dollars.

• 1:13:01Speaker 01

  I have an individual who worked in our office that came in the office. He's very kind of bubbly, enthusiastic, energetic person. And he was very depressed. And this went on for three or four days. I eventually asked him, I said, what happened? And he told me that he took a very large portion of the money in his bank account and he bought ski mask dog coin.

• 1:13:20Speaker 00

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• 1:13:46Speaker 01

  And I, before I laughed, asked him if he was serious. He said, yes. And I said, what happened? He said, it went down 99%. So, okay, that's not good. Do you have enough money for food? He said, I do. I said, okay, that was dumb. Now you learned your lesson. Don't do that again. Two weeks go by and he started to come out of his funk and all of a sudden he comes in the office and he's bouncing off the walls. And I said, what happened? And he says, well, remember that ski mask dog coin that I had? I never sold them. It came back. I'm now up like a hundred thousand dollars. I said, dude, go sell that immediately. And he ran over to his computer and he immediately sold all of it. I said, great. You made money. You escaped your problem unscathed. Don't do that again. And then three or four weeks later, he came in and he was depressed again. And I said, what happened?

• 1:14:27Speaker 01

  And he said, remember that ski mask coin? I would have had 11 million dollars if I'd held it. And so now he had the pain of regret, the pain of, you know, averted win. And so I told him, we're no longer allowed to talk about ski mask dog coin in our, in our office anymore. And I think that that is a perfect encapsulation of the experience of trading is that most people, myself included, are not a good trader. And so you're much better off just buying long-term assets, holding them. And when he said he turned a hundred dollars into 16,000, I thought you were going to tell me you turned 16,000 into a hundred. And so you guys were even.

• 1:15:00Graham Stephan?

  That guy is exactly me, not with dog ski mask coin, but I tell Jack all the time, I'm like, dude, if I had kept this, it would be worth this. Or I didn't buy this. I was about to buy it and I didn't. And now it's this. No matter what it is.

• 1:15:14Speaker 01

  Imagine if we had all bought Nvidia. In 2016, I have a tweet that says, the world runs on CPUs. Eventually it'll run on GPUs. I'm a genius. I didn't buy Nvidia. Like, what am I doing? And so that was a great lesson of like, the reason I knew that was because I was mining Ethereum, which at the time used GPUs. And so I had done a bunch of research on what am I buying? How do these work? What else can you do with them? The graphics card can be used for self-driving and DNA sequencing. And like, it was just like very obvious that there's going to be a bunch of use cases of future technology on GPUs. And I was smart enough to tweet it, or maybe arrogant enough to tweet it, but didn't do anything. And so I could sit there and be like, oh, actually, if I had bought Nvidia, look at how much money I would have. But like, you're going to waste your time doing that.

• 1:15:56Jack Selby?

  There's always a little bit of pain in every single trade, even successful ones, because you don't ever buy it perfectly at the bottom and then sell perfectly at the top. Because if it continues to go.

• 1:16:07Graham Stephan?

  I bought perfectly at the bottom.

• 1:16:09Speaker 01

  But you don't.

• 1:16:09Graham Stephan?

  Perfectly. 108, 108.

• 1:16:12Jack Selby?

  So we'll see how you feel when you exit it or don't.

• 1:16:14Graham Stephan?

  I haven't, I had not exited. That's, that's the problem is I'm really good at buying. I'm really bad at selling.

• 1:16:20Speaker 01

  Well, you're not unique in that. I used to think that buying was the hard part. So whether it's in the private markets or in the public markets, it's like, oh, can I find the best company? Can I get access to the private company? Can I go and find the right stock? I am now convinced after having done this for over a decade, buying is not the hard part. Selling is way harder. And I have spent maybe the last five years asking every smart person that I know in the investment world, how do you sell? And that is a question that I'm fascinated with now as to how do you do it? The best answer I've ever gotten is from a guy named Fred Wilson, who's at Union Square Ventures. He's a very famous venture capitalist. And he told me that when he's a private investor and a company is going public, he does a third, a third, a third. So when the company is going public, he sells a third into the IPO. 18 months later, he sells another third and then he last third, he never sells.

• 1:17:05Speaker 01

  And he's basically like, if it goes down after the IPO, I sold a third, so I made some money. If it went up 18 months later, I sell a third. And then he goes, and I hold a third just in case it ever turns into something crazy, then I'm fine there too. And I think that selling in a rules-based way like that is probably a much better approach than like us all waking up licking our finger and being like, you know, I think it's going down tomorrow. Let me sell.

• 1:17:25Jack Selby?

  Chris Camillo has a really good exit strategy, which is he enters a stock when he thinks that the general sentiment of a company is missing some big transformational aspect that could, that could affect the company. And then as soon as the general market sentiment understands that delta, that's when he exits. So it's like, as soon as people, enough people are talking about it on social media, it's like, okay, well, I'm done.

• 1:17:49Speaker 01

  Investing, in my opinion, is really about finding things that are not popular and then hoping that they become popular. Finding things that are not consensus and they become consensus. Same thing. They're not being talked about, then they become talked about a lot. And ultimately, that is how you get appreciation or asymmetry. And so it's very hard to measure, like, when is enough? When are people talking about it enough? I don't think people put enough credit on somebody like Chris, probably has developed a personal algorithm. He has consumed so much information. He's seen the pattern so many times that he's a feel for it. His personal algorithm is tuned to understanding, nobody's talking about this or somebody's talking about it. And if you were to ask him, define when the right time is to sell, he probably couldn't do it.

• 1:18:33Speaker 01

  But he could tell you, this stock has reached the point, I'm going to sell it now. And I think that we all have that to some varying degree. Somebody could be a real estate investor. They've looked at enough deals. They're like, oh, this one's not a good one. Why? The, the front facade is not going to be very attractive to buyers. Why not? They're like, I just know. And a lot of times we will discount that and say like, that's not a very scientific approach. But it is something about this human algorithm that we've been able to train over time that I think we should put a lot more weight on is because ultimately it is intuition that is driven by pattern recognition.

• 1:19:05Graham Stephan?

  So do you think then meme coins are bad for the overall market of Bitcoin?

• 1:19:11Speaker 01

  If you view it through an entertainment lens, let people knock themselves out. They can play video games. They can gamble. They can do whatever they want. If you think about it from a financial investing standpoint, it's incredibly stupid. And I think people know that, but they feel like they have no hope. They feel like they have no path to financial security. And so as that occurs, they're willing to take outsized risk. They need to get $100 turned into 16,000. You can't do that in the traditional stock market. So what do you do? You push out on the risk curve. They're willing to take more risk because they have less hope. They have less confidence in their skill to invest or build a business. And this is a story as true as time. If you go back to Weimar, Germany, or many other times in history,

• 1:19:53Speaker 01

  when you devalue a currency, you're punishing people financially. When they get punished, they lose hope. When they lose hope, gambling increases. If you just zoom out for a second, look at the United States of America, gambling is a massive problem. Not sports gambling, not just prediction markets, not just meme coins, not just in the stock market. Holistically gambling is an absolute national crisis. And so we think it is such a big deal that we've actually went and we acquired a minority stake in what I think is probably the leading platform that is trying to tell the stories of the people who get to the other side of gambling addiction. But what ends up happening is this is very well documented in drinking and drugs. So there's lots of podcasts, there's lots of rehab centers, there's lots of like infrastructure,

• 1:20:38Speaker 01

  where if you have a drinking problem, there's a path to getting sober. And I think that it's somewhat been normalized. It's like, hey, some people get alcoholic and then they go to rehab. They come out, their life is fine. Everyone celebrates and it's good to go. Gambling is still like on the edge of society. You don't really hear about a lot of people being like, oh, he's addicted to gambling. But I think that over time, over the next 10 years, that's going to become a major theme is that we're going to have tons of especially young men who are addicted to gambling. And there are going to be parents, loved ones, fiancés, spouses, sisters, brothers, cousins, kids, that are all trying to figure out, what do I do to help my loved one who's addicted to gambling? There's not a lot of infrastructure. And so we think that that is a major theme for the next decade

• 1:21:22Speaker 01

  that is going to significantly improve people's lives if someone figures it out.

• 1:21:26Graham Stephan?

  Well, what do you think about tokenization?

• 1:21:28Speaker 01

  I think tokenization is just stocks in a different form. I wrote a piece back in 2018, I think, where I created a framework where I said, we used to live in the analog age of securities. What that meant was everything was physical. You got a physical stock certificate, you got a physical deed to your home. The bond certificate showed up and you literally put it in a filing cabinet in your home. At some point, we transitioned to an electronic age, which was basically these electronic Q SIPs that sat in a centralized database. And when I own Apple stock, I don't get a physical certificate anymore. I just own the Q SIP inside of my account. We are now transitioning to a digital age of securities, which is now instead of that Q SIP, there's a token and that token I can take custody of, or I can leave it with some sort of custodian provider. And so if you look at that transition, it was still the same Apple stock. It was still the same deed to a home.

• 1:22:12Speaker 01

  It's just a new technology form factor. And so I don't think it'll have a profound impact on individual investors as much as the finance firms are going to like it because it's going to drive down costs, increase efficiency and help them make more money.

• 1:22:23Graham Stephan?

  Now, in terms of the big economic picture, are you bullish or bearish for the future?

• 1:22:27Speaker 01

  How could you not be bullish? There is nothing that you can show me that is bearish about the US economy, about technology or about humans.

• 1:22:36Graham Stephan?

  I would say, well, to be devil's advocate here, they're printing a lot of money. AI could disrupt a lot of people's jobs. We could see mass unemployment and we could enter an age where people can't adapt as fast as AI advances.

• 1:22:50Speaker 01

  AI is creating jobs. AI is boosting the US economy and printing money will enrich you as long as you own investment assets. Things happen in the world, they're neither good nor bad. In the first book I wrote, one of the chapters that I think got people very worked up was I said, luck is not real. And the example I use is if you're walking across the street with me and we both get hit by a bus. And when we get hit by a bus, we lose our leg. Somebody comes to the hospital and visits us and they asked you, what happened, Graham? You say, well, I was really unlucky today. I walked across the street, I got hit by a bus and I lost my leg. If somebody then comes to my bed and says, what happened? And I say, man, I am so lucky. I got hit by a bus, lost my leg and I didn't die. Same event, same outcome, two different mindsets. Same thing about money printing. You can sit and have a victim mindset, say they're printing so much money, they're going to hurt me.

• 1:23:35Speaker 01

  Or you can say, they're going to print so much money, they are going to make everyone who owns an investment asset rich. Same outcome, same thing, but two different perspectives. And so my whole message, I think, to people in the books I've written and a lot of the things that I tweet and talk about is you have agency. You cannot change whether they print money or not. No vote, no demonstration, no protest, no politics, nothing is going to change what they do. So you have to decide, if they do that, am I going to get hurt by it or am I going to benefit from it? Same thing with AI. We can yell and scream all we want, how dumb we think these people are saying that AI is going to kill everybody, or how smart and how much we agree with them. They're going to do what they do. You have to decide, am I going to use AI or am I not? Am I going to sit in a job where I think AI could displace me?

• 1:24:18Speaker 01

  Or am I going to be the guy at the company who becomes the AI guy? Cause I learned how to use it and I become indispensable. The technology is the same. It's just what do you do? What is the agency that you exert into the world? And I think that in my life, across all of these different, you know, kind of life experiences I've had, I know people who work in blue collar. I know people who are some of the richest people in the world. All of them that are successful in any form or fashion exert agency on the world. And so I just think that's what it ultimately is going to come down to.

• 1:24:45Graham Stephan?

  So what do you think the average person watching should be doing as soon as they finish this podcast?

• 1:24:51Speaker 01

  I think the single most important thing for most investors is to be educated. And I talk a lot about, why is it that half of the country sits in cash? Because they don't know that if there is any degree of money printing, they're going to be hurt.

• 1:25:05Graham Stephan?

  I'm in tax-free muni bonds, Jack. Jack keeps looking at me.

• 1:25:08Speaker 01

  Why?

• 1:25:09Graham Stephan?

  He keeps looking at me, insinuating that I'm sitting like a-

• 1:25:13Speaker 01

  I'm not trying to look at you.

• 1:25:14Graham Stephan?

  It's a tax-free yield.

• 1:25:16Speaker 01

  I, I didn't say anything. You're losing money.

• 1:25:18Graham Stephan?

  It's a tax-free yield, pre-tax equivalent to like 7%.

• 1:25:23Speaker 01

  You're losing money.

• 1:25:24Graham Stephan?

  He said it, not me. 7%?

• 1:25:26Speaker 01

  Yeah.

• 1:25:27Graham Stephan?

  I'm not losing money when you account for the risk-adjusted return. Sure, if I wanted to take more risk, I would make more money.

• 1:25:32Speaker 01

  Yes.

• 1:25:33Jack Selby?

  And no one's technically losing money on a risk-adjusted return.

• 1:25:35Speaker 01

  Yes. So.

• 1:25:39Jack Selby?

  Congratulations.

• 1:25:40Speaker 01

  The single most important thing I think for people to do is that in Sylvia.com-

• 1:25:43Jack Selby?

  Go to the bathroom, Jack. Come on, bathroom break.

• 1:25:46Speaker 01

  No, I, the single most important thing I think for people in the world is to make sure that they're educated. If they're educated, then they can exert their agency in the world. There is a long list of amazing organizations that are trying to put financial education into schools. I do not think that that is going to succeed because the problem is that they are teaching generic information to people who do not care. If you go back and you think about when you were 15, 16, 17, 18 years old, did you care whatsoever when the teacher was sitting there talking?

• 1:26:12Jack Selby?

  About finance, yeah, but about virtually everything else, no.

• 1:26:16Speaker 01

  So I believe that the best way to teach people is to teach them on a personalized level. The power of AI now is that we can personalize everything. We can personalize education, we can personalize healthcare, we can personalize, we can personalize financial insights, et cetera. And so I'm spending an immense amount of my time focused on how do we take artificial intelligence technology and deliver personalized insights to you and everyone else in the world? But use superhuman intelligence to give you that financial insight. And to me, the single most important thing for Sylvia is the more people use Sylvia, the faster their net worth grows. If there's a product in the world that the more you use it, the faster your net worth grows, why would you not try it?

• 1:26:53Graham Stephan?

  How is it able to grow your net worth?

• 1:26:55Speaker 01

  If you want a child to learn, what do you do? You give them one-on-one tutoring and the teacher sits there and says, Jack, I want you to learn this information. They go over it, they test you, you don't know it, they then teach you more and it's this one-on-one tutoring. If you want the best healthcare in the world, what do the richest people in the world do? One-on-one personal healthcare. In finance, that does not exist. And so with the power of AI, what we can now do is if you give a product context on your personal finances and then you begin talking to it about what your goals are, it can help you become informed to actually go after those goals. So when we built Sylvia, we never thought we were going to release it publicly. We built it for me personally. And what I had been doing was I was taking screenshots of my accounts and I was putting them into chat GPT and I was talking to chat GPT.

• 1:27:41Speaker 01

  And to be honest, it was okay because I was giving it context. The problem was then I came back the next day and I had to redo it all over again. So I had to go and get the amounts and go through this. When we started to build the product, it initially was just, I want to attach all of my accounts and I want to then talk to an AI with the exact real-time numbers in my accounts. We then started to add private investments, real estate, cars, collectibles, et cetera. And then we said, well, what if I could upload my tax returns and just give this machine as much context as I can? Over time, we realized that the existing legacy frontier models were not effective at answering these questions. And so what we've had to do is build an immense amount of proprietary technology to answer finance questions. ChatGPT, Claude, et cetera are very good at being smart. They can answer physics, history, math, all these different topics.

• 1:28:27Speaker 01

  They are really bad at answering very specific finance questions. So if you go to Google and you say, how do I get my tax rate down? It cannot help you because it doesn't know anything about your finances. If you go to chat GPT and say, how do I get my finances down? They'll hit you with a modal that says, well, connect your brokerage account. Well, what about my private investments, my real estate, all of the funds I've invested in, the collectibles, et cetera, that I own? It doesn't have your full financial picture. So what we did with Sylvia is when somebody comes to Sylvia.com, you come in, you attach your account, you upload your private investments. And when you ask that exact same question to Sylvia, what she will do is she will go asset by asset in your portfolio and walk you through and say, you know, hey, you guys own a piece of real estate. This is the address, that's in an opportunity zone. You should look at and make sure that you're actually getting the benefit of the opportunity zone.

• 1:29:11Speaker 01

  Cause I don't see it on your tax return that you uploaded. Oh, by the way, this stock right here is up, you shouldn't sell it, but this stock is down and you should tax loss harvest it. Oh, by the way, this exact asset right here, this company you own, it doesn't look like you have a 401K or a defined benefit plan in place. If you put that in place and you put a hundred thousand dollars per year on that off of your company balance sheet, that'll actually lead to a hundred thousand dollar tax savings for you and it'll compound and build equity over the next five years. That level of personalized insight usually would cost tens of thousands, hundreds of thousands of dollars a year. Cause you have to go to an accountant, the tax expert and all these different people. Well, now what you can do is you can use AI to do it. And so what we see people doing is they come in and when they use this product, the more they use it, the faster the net worth grows.

• 1:29:52Speaker 01

  But a huge reason for that is we have been able to build technology that when you go head-to-head, if you ask us a question versus Claude, us a question versus OpenAI, we, on objective measures that we have open source, so anyone can go run the test themselves, Sylvia is more accurate in tax, mortgage and credit cards, which means that we have been able to build technology that is better than OpenAI and Anthropic. These are multi-trillion dollar companies that have not been able to compete with us because is very specific. Applied AI is going to outperform generic AI in these different verticals.

• 1:30:23Graham Stephan?

  Is it safe to upload your tax return to chat GPT?

• 1:30:27Speaker 01

  It depends on what you're worried about. If you are using the product to get you answers, there are certain things that you can do. You can use zero data retention policies, et cetera. But I think one of the problems right now is that people have a lot of questions about how do these large language models operate from a security standpoint? There's a recent case where there was two mathematicians that were trying to solve a very hard math problem. And all of a sudden, OpenAI called them right before they solved it and said, hey, we solved the problem. And they said, well, how did you do that? We were using your product and we were uploading all the information. And OpenAI said, yeah, we know you were doing that, but like, we didn't look at what you were doing. We just, when we were over here and we ran our models against the problem, we solved it in 88 hours. This is a problem that no one has solved for like a century. And so what they are being accused of, which I don't know if it's true or not, but they are being accused

• 1:31:12Speaker 01

  that they were actually training their models on the data of those mathematicians were putting into the system. And that made the model much more likely to be able to solve this problem. OpenAI knew the problem was about to be solved, and so then they went and solved it themselves. And then they took credit for having solved some of it. I don't know what is true or what is not there, but what I think it brings up is, are you comfortable putting your data into a system where they are explicitly saying they are going to take your data, they are going to train on it, and they are going to use it for all these other purposes? What we do today is we don't actually train on the actual individual data that people are uploading. And we have immense amount of security in terms of SOC two. We encrypt the PII, do all of these things that make me comfortable to use the product. And I think that a lot of wealthy self-directed investors, that's what they're looking for in a product,

• 1:31:56Speaker 01

  is the ability to use it for the power of AI, but not have to give up on some of the security or privacy concerns that they have.

• 1:32:03Graham Stephan?

  See, imagine there's a hacker who hacks into your, like, let's just say ChatGPT, and threatens to extort you and say, hey, I'm gonna, I'm gonna post all of your-

• 1:32:13Speaker 01

  Why are you giving people ideas, man?

• 1:32:14Graham Stephan?

  I'm just saying, it's-

• 1:32:15Speaker 01

  I think that the personal assistants, the personal assistants, I think, are actually the bigger attack vector. So I don't know about you guys, but I have now used three different personal assistants that I think are relatively good. Grokbot, Instinct, and Muse from Meta.

• 1:32:30Graham Stephan?

  Yeah.

• 1:32:30Speaker 01

  And all three of these products, I have actually been surprised in hindsight how quickly I gave them access to my email calendar, you know, various things that two or three years ago, there was 0% chance I was gonna give context to these systems. Because of our work with Sylvia and my firsthand view of how much context can improve these products in your experience, I'm now much more open to, yeah, if you have access to my calendar, you can help me send calendar invites, make changes, call out conflicts, do all these things. To me, the personal assistants are actually like the attack vector that have maybe the highest risk. Meta obviously has a great security team and is kind of in a different category. But some of these startups where they have access to lots of people's things,

• 1:33:15Speaker 01

  and they're just getting started, that to me feels like maybe, you know, something that we need to pay more attention to.

• 1:33:21Jack Selby?

  What do you think right now is the best LLM?

• 1:33:23Speaker 01

  For finance, I think Sylvia is great. I use all the products. I always say that I think ChatGPT does a fantastic job for very specific things. ChatGPT I used when it first came out. I thought it was fantastic. Then all of a sudden Claude showed up, and I thought that Claude code, Claude cowork, all of those types of kind of like execute work became really big. And I would only use ChatGPT as like basically a better Google. And then Gemini's Nano Banana came out, and I started using that for a lot of image generation, et cetera. And then ChatGPT came out with a better model, and all of a sudden I was then using it for a lot more, including image generation. And so I tend to go back and forth between a lot of the different models for different uses. And the way I think about it is, I use Slack to communicate internally with our team.

• 1:34:06Speaker 01

  I don't think I've ever been like, let me find someone on Slack at a different company. It's an internal tool. My email, I don't send that many emails to other people on our team unless I'm like CCing them. I usually use email for like external communication. X, I use to communicate with people I've never met before, and it's kind of like a one-to-many broadcast. So I have three communication channels for anyone in my professional life. Then text, I have really for my family, friends, et cetera. So it's four different communication platforms, all that have different use cases. AI is very similar to me. I want to use Sylvia for finance. I want to use Claude for things like Claude code. I want to use ChatGPT to get information, do research, et cetera.

• 1:34:46Speaker 01

  I want to use Instinct for personal use. I want to use Grokbot to do a lot more in terms of our companies.

• 1:34:52Graham Stephan?

  And this is like TV channels, where it's like you need this subscription, and this one, and this one, and this one. That's a lot.

• 1:34:58Speaker 01

  Ultimately, I think that we are going to find you are getting way more productivity than the cost of doing it. So a great example is, I recently was going to hire an in-house recruiter for one of our companies. We need to hire a lot of people. And so I was like, wouldn't it be great to have somebody dedicated to just all day going through LinkedIn and trying to find people, doing an initial call, figuring out who's a potential fit, who's not, help me manage the process, et cetera. And I set up a bot on Grokbot to be a recruiter. And I started to describe to it, here's the types of roles that I need, here's what I'm looking for, here's what I'm not looking for. Go build me a list of 25 people. And it would come back and do it very quickly. And then as I would get on the phone with some of these people and I would do an interview, I would then go back to Grokbot and I would say, hey, by the way, I like that person. Here's the three things that they were really strong on.

• 1:35:42Speaker 01

  Here's two things I think that we need to dig more on, and here's one thing that I thought was a little bit of a red flag. By the way, if we go and move towards an offer with this person, they told me they're looking for this type of compensation. And I would just keep doing that over and over. And then towards the end of these processes, I would just ask the bot, I'd say, based on everything that I've told you so far, where do you think we're at? And it would say, hey, well, I think this person is most likely to take the job, but it seems like this concern would be, you know, potential issue. This person needs more convincing, but they're, you know, the most inexpensive, or whatever the analysis was. That replaced a person. It wasn't a person on our team that we like got rid of because of the technology, but we didn't hire someone because of the technology. And so I think that is just gonna keep happening over time. We have a public company with hundreds of millions of dollars in the balance sheet.

• 1:36:26Speaker 01

  We have more bots and agents that work at the company than humans. And it's only gonna grow a wider gap over time. So when you look at that, you say to yourself, well, where is the world going? The world is gonna start to morph to accommodate for the bots and the agents, not for humans. Already, companies are reporting that their technical documentation is being read by more bots and agents than by humans. So you start to write the technical documentation for the agents, not for the humans. Well, what happens when a website all of a sudden gets more traffic from agents than humans? Do you start to actually change the way the website looks, how it's constructed, what the site map is? We did this with SEO. There's a lot of websites that are built for how do the Google crawlers work?

• 1:37:09Speaker 01

  But I think that we're just on the precipice of figuring out like, what does an agent-oriented internet look like? What does agent-oriented products look like? I don't have the answers, but it's gonna be a lot of fun to figure that out over the next, you know, 10 years or so.

• 1:37:23Jack Selby?

  So we're gonna do a little change of pace here because we do need to wrap. But what is the best investing advice you've ever received?

• 1:37:32Speaker 00

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• 1:38:30Graham Stephan?

  You kind of also look like Bradley Cooper.

• 1:38:32Speaker 01

  Hmm?

• 1:38:33Graham Stephan?

  I said, you kind of also look like Bradley Cooper. You know, it's also interesting, I got a little sometimes for a brief second Tony Robbins, and then also got Alex Becker.

• 1:38:41Speaker 01

  What the fuck is going on?

• 1:38:42Graham Stephan?

  It's a, it's a mix of-

• 1:38:44Speaker 01

  Y'all know who you look like? Tom Cruise?

• 1:38:48Jack Selby?

  Yeah, yeah. Channing Tatum. Thank you.

• 1:38:51Speaker 01

  I'll give you two pieces of advice. I think one is Mark Yusko telling me, pressure winners harder than everybody, cut your losers faster than everyone. But I also think that there's a great piece of advice of, invest your portfolio like it's your children's, not your own. And there's a great watch brand. One of their famous ads is basically like, it's not your watch, you're just taking care of it for the next generation. And I genuinely believe that that is probably the best advice for your investment portfolio.

• 1:39:19Graham Stephan?

  That's Patet Philippe.

• 1:39:20Speaker 01

  It's not your portfolio. You're just taking care of it for the next generation. Because guess what? You're not gonna buy Dogecoin. You're not going to do all the crazy stuff. You're gonna say, my kid's money can't go into that thing, and I think you'll end up with better return.

• 1:39:34Graham Stephan?

  I want to ask you some fun scenarios. These are meant to be somewhat rapid fire, so each answer should be 15 seconds.

• 1:39:42Speaker 01

  Perfect.

• 1:39:42Graham Stephan?

  Bitcoin hits $1 million. What happened?

• 1:39:46Speaker 01

  They kept printing money.

• 1:39:47Graham Stephan?

  Bitcoin hits $10,000. What happened?

• 1:39:51Speaker 01

  Satoshi came back.

• 1:39:52Graham Stephan?

  Do you think that's the most likely? If Bitcoin-

• 1:39:54Speaker 01

  No. If Bitcoin hit $10,000, it's probably some sort of technical issue or threat where people panic, and it's kind of a whick down, and then it comes back.

• 1:40:03Graham Stephan?

  What's the biggest threat to Bitcoin?

• 1:40:05Speaker 01

  Them stop printing money.

• 1:40:06Graham Stephan?

  What would make you sell all the Bitcoin that you own?

• 1:40:09Speaker 01

  I will never sell it all.

• 1:40:11Graham Stephan?

  Is there anything that could change your mind where you say, I'm going to sell?

• 1:40:15Speaker 01

  If it was the last money I had to my name and my children weren't gonna eat unless I sold it, I would consider.

• 1:40:23Graham Stephan?

  If you could not own Bitcoin, what other asset would you own in its place?

• 1:40:28Speaker 01

  For long-term capital appreciation, I think Bitcoin, gold, and land are the three things that will benefit the most from money printing. So if I couldn't own Bitcoin, it'd be gold and land. If I want to create an enormous amount of wealth over a relatively short period of time, it would be a business that I was in control of.

• 1:40:45Graham Stephan?

  What's the next financial bubble?

• 1:40:47Speaker 01

  Financial bubbles are the next bubble. What I mean by that is, I do not believe that we will see a prolonged 18-month or longer financial crisis during the rest of our lifetime, because I believe that central banks have perfected the playbook on how to address any sort of market weakness, where they just hit it with a monetary bazooka. And so they will continue to distort the market, but I think that there will be ebbs and flows, volatility, 10, 15% drawdowns. I just don't see us 50% down for, you know, 18 months in the stock market.

• 1:41:18Graham Stephan?

  And we're gonna get some predictions here. Where do you predict the price of Bitcoin to be at the end of 2026?

• 1:41:25Speaker 01

  Higher.

• 1:41:26Graham Stephan?

  What about the end of 2030?

• 1:41:28Speaker 01

  Much higher.

• 1:41:29Graham Stephan?

  What target do you have in mind where if you say- Bitcoin's price, I think, is going to be here. I have the highest confidence of that price.

• 1:41:41Speaker 01

  I don't know where Bitcoin's price is going on any given timeframe. I think I have been humbled over the years by my inability to predict the exact price on a given timeline. What I do believe is that Bitcoin will go to a million dollars during our lifetime. I think that there are a number of converging forces that are driving it higher. What I am very fascinated by and wish I had an answer to is how many more cycles will we go through to get to a million? If Bitcoin goes from 75,000 to 250, down, then it goes to 700, and then it goes to a million, that would be three cycles. Or is it something where we need like six, seven, eight different cycles to get there? And so you and I are, you know, old decrepit men who are just holding on until Bitcoin hits a million.

• 1:42:23Jack Selby?

  What do you think Bitcoins are gonna be at at 2030?

• 1:42:25Graham Stephan?

  Yeah, I just, I wanted to predict both. So, end of 2026, I'm gonna say 65,000. I think it's gonna go down a little bit.

• 1:42:32Speaker 01

  Down, okay.

• 1:42:32Graham Stephan?

  2030, I'm gonna say $174,000 in 2030. That's my, just, I'm gonna throw it out there and we'll see what happens.

• 1:42:42Speaker 01

  Why so bearish?

• 1:42:44Graham Stephan?

  You think 174 is bearish?

• 1:42:46Speaker 01

  If you just look at the four-year cycles, it's probably...

• 1:42:48Graham Stephan?

  Yeah, but if it goes down to 65, that's pretty, that's pretty good.

• 1:42:51Speaker 01

  The difference between 65 and 75 to me is, is miniscule.

• 1:42:55Graham Stephan?

  I think that's triple in three years. If it goes to 65 to 174, I think that's fantastic.

• 1:43:02Speaker 01

  What a boomer.

• 1:43:04Graham Stephan?

  What about the S and P 500 price by the end of next year?

• 1:43:09Speaker 01

  I think the S and P will continue to compound at 10 to 12% for the foreseeable future. Historically, it's been, you know, 8% or so, but I do think that the accelerated money printing plus, one of the aspects of the S and P that I don't think gets enough credit is the companies have actually seen their multiples compress because they are making so much more money. And so naturally, if you see earnings per share going up, if you see company revenue growing, profits growing, the index should actually accelerate. And so I think that 10 to 12% for the next, you know, decade or so is probably a good, a good target for the S and P.

• 1:43:42Graham Stephan?

  Do you think Michael Saylor is positive or negative for the Bitcoin market?

• 1:43:47Speaker 01

  I don't think that anyone is positive or negative. I think that everyone is a market participant and the market is great at ingesting information and figuring out a price. Michael Saylor has done a fantastic job of spreading the education of Bitcoin. I think that there are plenty of people who critique him for various things, but there's plenty of people who critique me, you, you, everybody else. And so I don't think so much about positive or negative for a market as much as, Michael Saylor has bought a lot of Bitcoin and generally people buying Bitcoin means that the price is gonna be higher, not lower, as long as they don't sell it.

• 1:44:17Graham Stephan?

  Do you think AI is gonna make most people richer or just the top few?

• 1:44:22Speaker 01

  I think that artificial intelligence is probably one of the most powerful technologies that we will ever see introduced. And what I know is that the world has been seeking intelligence for literally centuries. They've been willing to scour the earth, pay as much money, do whatever it takes to find the most intelligent people. And now you have that intelligence in your pocket. And so my guess is that most people are gonna be able to figure out how to make more money because technology historically has made everyone much, much wealthier. If you think about the average person in America today compared to the average person in America 100 years ago, we are incredibly fortunate. It is very hard to think that way when you look on Instagram and you see people on vacation or in a Ferrari or, you know, a yacht.

• 1:45:02Speaker 01

  But ultimately, the direction of progress for humanity and for Americans in particular is only in one direction. And I think technology is the bulk of why that's happening.

• 1:45:11Jack Selby?

  Altman or Musk?

• 1:45:12Speaker 01

  I would never, ever, ever bet against Elon Musk.

• 1:45:15Jack Selby?

  No.

• 1:45:16Speaker 01

  Would you? I'm gonna get your head checked out if you say yes.

• 1:45:19Jack Selby?

  I've never, I've never bet against him and I've never regretted betting with him.

• 1:45:23Speaker 01

  Yeah, I feel the same way. Look, there are certain people who have an it factor. There is almost no one I know who can go into different industries and build large companies. And there's never been a person in human history who has built six different multi-billion dollar companies over a 35-year period.

• 1:45:40Jack Selby?

  What do you think makes him able to do that?

• 1:45:43Graham Stephan?

  Autism.

• 1:45:45Jack Selby?

  Then why can't you do it?

• 1:45:47Graham Stephan?

  Name, man.

• 1:45:49Jack Selby?

  Because I'm not that autistic, man. Or too autistic.

• 1:45:52Speaker 01

  I think that Elon understands risk is drastically overestimated. He understands stories are more powerful than most people believe. And he has figured out the code of how much I work equals how much output I get. And there's just not a lot of people who have put those sort of things together.

• 1:46:12Graham Stephan?

  Yeah, I wouldn't bet against Elon or Vlad Tenev.

• 1:46:15Jack Selby?

  Yeah.

• 1:46:16Graham Stephan?

  Those are the two people who I think are gonna change the world.

• 1:46:20Speaker 01

  I do think that Vlad has changed the world, right? Like, he, he pretty much forced many of the brokers to go no fee. And it was because he had an idea and brought it to the world.

• 1:46:30Graham Stephan?

  It's down right now quite a bit after hours, so.

• 1:46:34Jack Selby?

  Oh, really?

• 1:46:35Graham Stephan?

  Because the Clarity Act failed. Well, let's see. Because if they hike rates...

• 1:46:40Jack Selby?

  Let's see if it ends up going up or down and then we'll know if it was or wasn't a buying opportunity.

• 1:46:45Graham Stephan?

  I think, I think in the 60s and 70s, that's a really, really, really good opportunity.

• 1:46:49Jack Selby?

  And how many years will you think that for?

• 1:46:51Graham Stephan?

  What?

• 1:46:52Jack Selby?

  How many years, because you've been saying that for a few years.

• 1:46:54Graham Stephan?

  Yeah, and it was, and then it spiked up.

• 1:46:56Jack Selby?

  Right, but as time goes on, generally speaking, markets increase and like 60, 60 to 70 obviously will be a great deal.

• 1:47:03Graham Stephan?

  How, how are those call options going, Jack?

• 1:47:06Jack Selby?

  Uh, I actually have no options. I have no options on Robin Hood right now. I have no options on Robin Hood right now. Better for worse.

• 1:47:12Graham Stephan?

  Well, maybe you gotta sell covered calls.

• 1:47:14Jack Selby?

  Selling covered calls is actually, I'm kidding, we don't need to get into that. Thank you so much for coming on the show.

• 1:47:20Speaker 01

  Thank you guys for having me.

• 1:47:21Graham Stephan?

  We'll link to all of your info down below in the description. And for the members who want access to our next episode early, feel free to join, the next episode is already live. And if you wanna see the uncensored bits that we kept in here of Jack going to the bathroom multiple times.

• 1:47:39Jack Selby?

  I'm, I drink a lot of water. Okay, you drink nothing.

• 1:47:43Graham Stephan?

  Feel free to join, you'll be able to see that as well. Thank you so much for watching and until next time. I want you to describe the housing market in one word.

• 1:47:51Speaker 06

  Crap. If you're buying your first home, that door is closing and it's getting harder to open.

• 1:47:57Speaker 07

  When it comes to rents, we're actually not in an affordability crisis at all.

• 1:48:03Graham Stephan?

  So why does there appear to be so much outrage about the affordability crisis now?

• 1:48:08Speaker 07

  The media loves to amplify any kind of negative. I mean, we're basically built to be attracted to negative news, to be attracted to, attracted to fear.

• 1:48:17Speaker 06

  This is a chart of the average third-year mortgage rate, which hit 7% this week.

• 1:48:22Graham Stephan?

  Who's even buying right now?

• 1:48:23Speaker 07

  Only people who need to buy.

• 1:48:25Graham Stephan?

  Is now maybe actually the good time to buy when no one else wants to buy real estate.

• 1:48:29Speaker 07

  You could have made that same argument, you know, two or three years ago. And you'd be sitting on a home that was equal to or lower value.

• 1:48:35Graham Stephan?

  What would it take for housing values then to fall 20%?

• 1:48:40Speaker 07

  Well...

• 1:48:56Speaker 07

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