Kevin O'Leary's Shocking Prediction For The Stock Market, Housing Prices, & 2026 Economy

Bizee: #Ad Big thanks to Bizee for sponsoring today’s video – they make starting an LLC super simple: https://bizee.com/ich SoFi: Thanks to SoFi for sponsoring today's episode. Visit https://Sofi.com/iced to start your crypto journey. Lennar: Try out Lennar Investor Marketplace at https://www.lennar.com/investormarketplace_icedcoffee Airbnb: Find a co-host at https://airbnb.com/host Subscribe TO @kevinoleary *𝗖𝗢𝗡𝗡𝗘𝗖𝗧 𝗪𝗜𝗧𝗛 𝗨𝗦* 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 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! Timestamps: 0:00 Intro 1:10 CNN Panel Drama 6:42 Current State of the Economy 9:56 $65K a Year to Millionaire 12:07 Where He's Investing 16:02 Sponsor - Bizee 17:18 Kevin's Plan for the Kobe Card 19:57 Investment Breakdown 25:27 Investments Headed for Collapse 28:59 When Will the Next Recession Hit? 30:09 Sponsor - SoFi 31:30 Wealth Tax Debate 37:44 Is Kevin O'Leary Really an Asshole? 39:16 Brutal Honesty & Billie Eilish 41:27 Feelings vs. Truth 44:11 Hardest Truths Given & Received 47:33 AI Replacing Actors in Movies 50:52 Best Shark Tank Investments 52:15 How AI Will Change Business 54:26 Can Kevin Be Replaced by AI? 1:00:14 Sponsors 1:02:32 Best Investor of All Time 1:03:59 Building Wealth on an Average Income 1:11:14 How Much Did Marty Supreme Pay? 1:16:30 Toughest Negotiations & Biggest Screw Ups *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.r 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.

• 0:00Speaker 00

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• 0:29Speaker 01

  Every story has a hero. It has a bad guy. I want to be the bad guy. You're in. Get the f**k out of here. You're gonna spew bullshit at me? That's gonna cost you something. So what? This is business. Life is hard, then you die. Get over it. Some people just go crazy when they hear the truth. And I don't care.

• 0:49Graham Stephan?

  What really motivates everybody at the end of the day is money. What's an investment that everyone loves right now that you think is going to collapse?

• 0:58Speaker 01

  It's never the one you think. I'm breaking little news here. Something's gonna go down 80% because of AI's disruption.

• 1:07Graham Stephan?

  Will AI replace more jobs than it creates?

• 1:09Speaker 01

  No. We just don't know what the transition's gonna look like. AI is gonna be such a powerful tool. It'll create new industries we haven't even thought of.

• 1:16Graham Stephan?

  When do you think the next recession is gonna hit? And what do you think is gonna cause that?

• 1:21Speaker 01

  It's not gonna end well. It will destroy the fabric of the economy.

• 1:31Graham Stephan?

  Kevin O'Leary, thank you so much for coming on the Iced Coffee Hour.

• 1:35Speaker 01

  Well, I always enjoyed it.

• 1:36Graham Stephan?

  Really appreciate it. I want to get your reaction to this clip. It just recently went viral. And I want to know what was going on.

• 1:43Speaker 01

  My goodness.

• 1:43Speaker 03

  All right, Kevin, a quick last word.

• 1:45Speaker 01

  Oh, wow.

• 1:46Speaker 03

  Which I'm not sure.

• 1:47Speaker 01

  My last word is you're all nuts. Like, that's just...

• 1:49Speaker 03

  Oh, my God.

• 1:50Speaker 01

  Thank you, Kevin.

• 1:51Speaker 03

  Guys, as you please.

• 1:52Speaker 01

  Want in on that?

• 1:53Speaker 03

  We gotta keep it together here, okay?

• 1:55Speaker 01

  We are.

• 1:56Speaker 03

  Honestly, I mean, there's a way to talk about these things. If you don't have anything to say, just say that. And I won't come to you next time.

• 2:02Speaker 01

  I just said something very important.

• 2:03Graham Stephan?

  You just said something very important. In your own words, which was you're all nuts.

• 2:07Speaker 01

  So I, you know, Abby and I have had a long relationship. And she is actually very successful right now on CNN. I believe she has the fastest growing numbers on that platform.

• 2:21Speaker 01

  And I think CNN has also determined through its producers that they will garner a larger audience if it's a real debate. In other words, instead of just taking one side or the other, which there was a time in media where that outlet was left, that outlet was right. But that's not what advertisers want. They don't want to bi-africate the market in 50/50. They want every customer, regardless of what their politics are. And so what I've learned, and I think I'm the only guy doing this, I go to every outlet. I go to all of them and I stick with policy, not politics. I don't show for politicians. I show for policy that I think is good

• 3:07Speaker 01

  or policy that I think is bad, and I have an opinion about that. I'm a columnist, I'm not a journalist. And so in the case of that narrative, we were debating the performance of, I think it was Munich, and it was AOC talking about policy in Munich. And she clearly was not prepared. And so she, she did not have a good outcome in terms of global press. And we were talking about that. And they seemed to want to say, well, that was okay. She just had a, a brain fart or something, or whatever they were calling it. And I said, and they were trying to compare it to Trump. I said, this has nothing to do with Trump. Trump wasn't there. This is a poor performance by AOC.

• 3:52Speaker 01

  Now let's draw this analogy. If I get hired to go speak to an audience, which I do. I want to know who's in the audience. I want to know exactly what the narrative is going to be. And I want to, I want to be prepared. I want to know my stuff, you know, before I get out there. Because I'm gonna, you're gonna get fried if you don't know what you're talking about. And that's what happened to her. She didn't know what she was talking about and basically didn't prepare. And she, so I say, look, she failed. And I, to me, that was factual and it caused a big debate.

• 4:26Jack Selby?

  So why do you think it went so viral calling a CNN panel nuts?

• 4:31Speaker 01

  I thought it was a humorous moment. There was only 15 seconds left to the show and they were so.

• 4:39Jack Selby?

  Do you actually think they're nuts? Or do you think that they like?

• 4:42Speaker 01

  That, that moment was a temporary moment of insanity for them. They just couldn't deal with the fact that I was not going to stop telling the truth. She failed on her mandate. She did a poor job as a speaker that day. And that is true. She was terrible. And somehow, if you don't tell the truth, how's she expected to get better? She failed. She got an F minus. She'll never do that again. I mean, everybody on earth watched her do word salad for 30 seconds.

• 5:14Jack Selby?

  So do you think that the CNN panel actually believe what they're saying? Like, oh, she just had a brain fart. Like, it wasn't anything that's reflective of her actual intelligence or knowledge on what's going on? Or do you think that they're being fed information? And they're like, okay, well, this is just the narrative that we have to purport.

• 5:30Speaker 01

  You know, it's, imagine this, you're into a vicious discussion, a really high energy discussion. And then we go to commercial break around the table.

• 5:43Jack Selby?

  We should have an ad.

• 5:44Speaker 01

  Yeah, right here. Because that actually is what happens. And tempers are, are high and people are mad and they're, you know? I've been doing this a long time and I learned a long, long ago, you know, when, when you're on a, doing live television and you're, you're having a political narrative or a debate, there's a moment of, of three minutes where all of a sudden, just like the three of us sitting here, it stops. And, and I always say, well, how about those Yankees? Like, you know, what else are you gonna do? Because everybody's upset. The, the good news, I think, is in the end.

• 6:24Speaker 01

  People want to see both sides. How it's presented to them is a matter of style and the show's producers and everything else. But Abby Phillip's show is doing very well. And I'd like to think I'm a contributor to it, you know? And I, and for me, I don't want to go and sit at 10 o'clock at night and be bored to death. I want to have some fun. And boy, we have fun on that show because if you're a left winger that is not willing to deal with numbers, for example, we had a debate about the economy and I'm sitting there, you're going to have a problem because I know my numbers. I have facts, I deal with them. I know exactly where we sit on the S and P, the Dow and where we're at in terms of cash flow, you know, per quarter and all that.

• 7:07Speaker 01

  And you're going to spew bullshit at me? That's going to cost you something.

• 7:11Jack Selby?

  What are the most astonishing facts on the economy right now?

• 7:16Speaker 01

  The resilience it has. As we have major forces at play, I'll give you two major forces. Obviously tariffs, most people thought would be highly inflationary. That hasn't proved out to be the case. There is some increase in input costs. They need to be fine tuned. But the impact of AI was underestimated as a productivity tool. Look, look at what happened with Square just the last 24 hours. And look how much the stock has gone up as a result of cutting the workforce by 40%. So there you have the good, bad and the ugly in that thing. But AI is turning out to be a massive productivity tool for margin enhancement, increased cash flow and productivity, all at the same time, not just in one sector, in all 11 sectors

• 8:01Speaker 01

  of the economy. All 11 sectors use AI today. And 24 months ago, you would have said that's hype. And I can give you examples in my own portfolio of companies of which every single one is using an AI tool, paying for it, renting it, whatever they're doing. And how they're using it and how it's enhanced cash flow in the last six months.

• 8:19Graham Stephan?

  What do you think about Sam Altman saying that a lot of the layoffs are simply AI washing? And that these companies are using AI as an excuse to fire people because they might have over hired or spending too much money, or maybe their financials aren't good, so they blame AI?

• 8:33Speaker 01

  Yeah, I think there's a lot of that going on. But the offset, and I mean, just look at, let's use an example, just a very, this is two simple examples that everybody's going to understand. That wasn't happening 18 months ago is happening now. Let's take the insurance industry, make it easy, the watch insurance industry, I'm involved. I have a company called Wonder Care that insures watches. So if somebody goes online and says, I want to insure this Rolex Daytona,

• 8:59Speaker 01

  it would take up to two weeks to write a policy. You'd have to go do research, you know, actuarial data, how old, what zip code are they in? How much fraud is in that state? What are the laws of that state? We can issue that policy now in nine seconds through data scraping. So the productivity is insane in terms of what and what's it, what's it done for margin enhancement? How about this one? You own a large box retailer. Each year for your insurance, you have to send a guy up on a ladder. Or Wendy's or McDonald's, the same for any commercial building, no matter where it is in any state. You have to inspect the roof for leaks and all of the air vac, all of the HVAC system, everything. And then if there's any repair required, you have to issue work order and get it repaired

• 9:45Speaker 01

  in order to maintain your insurance. How about a 6K drone just flies over it in a matter of 30 minutes? Compares that image from the one it took last year down to a 6K resolution. It sends it to a satellite and before anybody even stops flying the drone, issues the work order for repair.

• 10:06Speaker 01

  Nobody gets up a ladder. The only person that went there, it's a company called Fly Guys. We own a piece of it. They just fly drones and it's all done with AI. So you fly a guy out in his Ford 150 to that McDonald's. Eh, above the top, it's over. That's it. Nobody goes up on a ladder in the summer or the winter and gets injured. That's AI.

• 10:26Graham Stephan?

  So you've said before that someone making $65,000 a year could become a millionaire.

• 10:30Speaker 01

  Yeah.

• 10:31Graham Stephan?

  Could you walk us through that math? And is there an income level where it's just mathematically impossible with living expenses? That you just can't do?

• 10:38Speaker 01

  Not if you're 65. It's when you're, when you get to 65. The way it works is, and we don't have the discipline. And I'm going to walk you down a lesson that I learned over the last six years on this. Remember when fintech was smoking hot and everybody's bringing apps to the market to help you trade stocks? Buy bonds? Buy derivatives? Buy options? It was all done on your phone and everybody thought, well, this is going to make it just democratic. Everybody out there is going to be able to be like a multimillion dollar investor because they got the tools for nothing.

• 11:12Speaker 01

  None of that worked.

• 11:14Speaker 05

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• 11:43Speaker 01

  None of it. And we, I was developing something like that. We started with a version of Bean Stocks. I'm promoting something I invested in. And it never worked because people actually don't know how to read a stock chart or what candles are or what 200 day averages are, or any of that stuff. What they really wanted, it turned out, was the ability to push a button in one transaction and put 60% of it into stocks and 40% of it into bonds. That's it. That's it. And the smarter we made the app in terms of simplicity. It when it got so simple that that's what you could do and that's what Bean Stocks does today, then it took off.

• 12:26Speaker 01

  Because the only decision you have to make in your life is what is the discipline each week you have to take your income and what percentage 10, well, some people 5, 10, or 15% are you going to put into the market and never take it out till you're 65? You want to be a millionaire at 65, a million and a half dollars? Take 20% of your salary of $69,000 and put it into the market each week and don't touch it and just watch it on your phone grow. It goes up and down as the market moves, but generally speaking, the market for the last 150 years has given you anywhere from 8 to 12% annualized every single year. You don't have to guess or pick stocks. You don't know, you just buy an index. That's what the app does.

• 13:06Graham Stephan?

  How are you investing your money?

• 13:08Speaker 01

  I only do indices now. I basically say, because I've learned through, you know, our Bean Stocks experience, I use an Alps product, I helped design it and then we sold it to Alps called OShares. So they have an index for S and P, an index for technology, an index for Europe, and an index for Asia. I put 40% into the US, 20% into Europe, and the rest spread across the other two and I forget about it.

• 13:37Graham Stephan?

  How often do you check your portfolio?

• 13:39Speaker 01

  Every day at 4:05. It's all, I have a huge dashboard, not only my public companies, but all my private investments too. I mean, I have a lot in real estate, I have a lot in, well, in collectibles. You know, I've gone into, we've had, in my, my group that we formed, we have over 100 million in cards now. It's been one of my best investments.

• 14:03Graham Stephan?

  What's the most valuable card you have?

• 14:05Speaker 01

  Do a Logo Man, Jordan Colby. You know I'm going to be walking on the red carpet of first SAG-AFTRA, the Actors Awards on Sunday here, but then the Oscars on the 15th. And I thought, what could I give back to Los Angeles that would be really cool? And I came up with this idea. I thought if we could take the Jordan Kobe dual logo man, that card we bought last August for 12.93 million dollars.

• 14:34Jack Selby?

  I also didn't know you bought that. That's I know, I know the card sold for that, but I didn't know it was you.

• 14:38Graham Stephan?

  It was everywhere. Yeah, I saw the press tour after it.

• 14:40Speaker 01

  But then I thought to myself, Paul Logan did something cool with his Pokemon. He hung it on a necklace and he wore it. I thought, how can I take Paul's idea and elevate it? Turn it to 11? How can I max it out? So I called up my good friends at Tiffany's. And I said, can we talk to Paris? Let's dream up a necklace made of all diamonds and rubies. And I'll wear that at the Oscars. Because Kobe should be back in LA. And nobody knows I'm coming with that. That thing's going to be worth about 25 million dollars. I'm only gonna have security everywhere, obviously. Brings trucks and everything.

• 15:24Speaker 01

  But when I get on that red carpet, I'm gonna be wearing that. It's gonna be a mind blower. And it's going to make the necklace that we've designed.

• 15:34Speaker 01

  I actually am wearing the two watches that we designed it for. The classic Daytona rainbow, which is rubies and diamonds, graded colors. And then, of course, all ruby diamond AP skeleton. I think I'll be wearing both of those with the card here. Can you imagine the bling? I mean, that's

• 15:53Jack Selby?

  You're like the rich person final boss. You're like, literally like Mr. Burns.

• 15:57Graham Stephan?

  This is like a side quest at this point.

• 15:59Speaker 01

  It's about art. It's about taking it into wearable art. Because the Kobe dual logo man is considered by some the supreme card.

• 16:09Jack Selby?

  Yeah.

• 16:09Speaker 01

  In its design, the fact that it has the original jerseys. Both logos are perfect. I mean, the whole thing, and I've only been able to see that out of the vault once. Because it's vaulted, it's insured. But it's coming out on the streets of LA on the red carpet and it's gonna be insane. It's gonna be.

• 16:28Graham Stephan?

  So we just had Logan Paul on the podcast.

• 16:30Speaker 01

  Yeah.

• 16:30Graham Stephan?

  And we were talking about the card and I was asking what the Logan Paul premium was for the card. And he definitely said his name associated in the story behind it and him showing it adds a level of premium for a buyer because that has a story to it.

• 16:44Speaker 01

  Well, imagine what this card is.

• 16:45Graham Stephan?

  Yeah.

• 16:46Speaker 01

  I mean, think about walking red carpet of the Oscars. We're nominated for nine Academy Awards and Marty Supreme. This is a chance of a lifetime to bring Kobe back into LA in its flashiest moment, you know?

• 16:59Graham Stephan?

  So what's your plan with the card? The starting a business sounds exciting, but the biggest roadblock for a lot of people isn't the idea. It's all the paperwork. Like everyone says, oh, just go and start an LLC. But nobody tells you exactly what's involved and how to do it correctly.

• 17:14Jack Selby?

  And that is exactly what today's sponsor, Busy, is all about. I've personally used them myself and I gotta say, I was so amazed at just how easy and simple the entire process was. I literally got my LLC set up in less than 10 minutes and just knowing that everything was getting filed properly and done professionally made getting started way less intimidating.

• 17:32Graham Stephan?

  Busy's helped over a million people start their business and what makes them stand out is just how simple they make the entire process. There's no confusing paperwork or endless forms. You just answer a few questions and their team handles the rest so that you could actually focus on growing the business. On top of that, every business formation comes with your first year of a registered agent service included for free.

• 17:52Jack Selby?

  And Busy does not just set you up and then leave. They offer ongoing tools and services to help you actually manage and run your business throughout the year. So you're supported way long after the initial setup.

• 18:02Graham Stephan?

  Don't wait. Make 2026 the year you finally launch your business. Go to busy.com/ICH right now. That is B I Z E E dot com slash I C H with the link down below in the description to get started. Busy.com/ICH. So what's your plan with the card?

• 18:20Speaker 01

  So the card, my philosophy, we talked earlier about ETFs, right? I like diversification. So if I own Europe, I own 50 stocks. My portfolio is 50 of the largest European stocks in that O share.

• 18:37Speaker 01

  I want to own 50 cards. I don't want to bet the farm on one card. I want the 50th most valuable cards on earth in one Holdco that I'm a shareholder in. That's what I want. Because I went back and did the research. Go back to 1958 in modern and contemporary art. Track every single painting. You can do this online now easily. What you're going to find out is 98% of the returns of the modern and contemporary art market came from the top 20 pieces of art, top 20 artists, that they're rarest pieces. So a Picasso that you bought for $2,500 in 1962,

• 19:21Speaker 01

  that trades for 140 million today. Not some other artist, the Picasso. You could, there were thousands of modern artists, but Picasso's the one you wanted. Warhol. There were all kinds of people in New York in the 70s doing what Warhol was doing, but none of those have traded up. You got to own the Warhol. You want the Mick Jagger. You know, you, so that's my philosophy with cards. So I got together with two other guys, Shine, probably the number one collector on earth. I said, Shine, go find me every single Picasso and Warhol in every sport. And it doesn't, and what you've learned about the data, it doesn't matter what you pay. It just doesn't matter, you know,

• 20:06Speaker 01

  whether you pay 8 million or 20 million or 50 million, doesn't matter. If you just let time do its thing, those cards outperform all the rest of that sector if they are piece uniques. So that code, the Jordan Kobe logo, man, that's a piece unique. There's only one of those. So we paid 12.93 million, middle of August last year. Go to Cardlighter, it's 17.2 million right now. It's better than the S and P.

• 20:37Jack Selby?

  Have you gotten an offer after purchasing it?

• 20:39Speaker 01

  Oh, yeah, yeah, yeah. We're not selling that card. I'm not selling any cards. Like, how am I going to buy them back? They're piece uniques.

• 20:47Speaker 01

  This is better, it's done way better than crypto, way better, like way better than Bitcoin, way better than the S and P 500.

• 20:55Jack Selby?

  So in terms of your portfolio, then, if you were to allocate percentages and how it's invested, what percent would be alternative investments like cards, collectibles, as opposed to index funds, individual stock picks, private companies, real estate? Like, how are you currently diversified?

• 21:13Speaker 01

  Yeah, that's actually the secret sauce. And it's the thing about diversity, it's the only free lunch in investing. Very simple rule for me. On traditional equities and debt, no more than 20% in any one sector. There's 11 sectors in the economy and no more than 5% in any one stock or bond. So think about, you've got 11 sectors. Real estate's the 11th sector in the S and P, the most recent. The only rule I break is real estate. I have about 32% of my portfolio in real estate.

• 21:47Jack Selby?

  Is that commercial real estate?

• 21:49Speaker 01

  No, it's a blend. But right now, what's really exploding in terms of value for me are the deals I did in data centers. I bought 10,200 acres in Alberta, Canada, and last week we announced 10,300 acres in Utah. Both locations have extraordinary attributes in terms of what the hyperscalers need. So I'm really, really long real estate right now because if you look at the cash flow in all commercial real estate, there's never been in history this much capex allocated to this sector.

• 22:28Speaker 01

  This is, we have demand right now for 45 gigawatts of data centers and only five under construction. Think about that. So for the next seven years, I want to be long land that has power, fiber, permits and water.

• 22:44Jack Selby?

  So how does it look then in terms of like percentages? Like if some person out there watching with 10K to their name, how are they going to mirror your portfolio?

• 22:53Speaker 01

  Right now. What's declined the most in the last year? So let's look at where we sit right now. I would say on a portfolio basis, I'm about 60% equities globally.

• 23:11Jack Selby?

  Is that private, public?

• 23:13Speaker 01

  It's, yeah, we're gonna make it much simpler numbers here. It's private and public. I'm about 5% in alternatives, including cards. I used to be 11% in crypto, but I discovered something quite disturbing, I might add. We'll take a little derivative here. So I'm down, you know, quite a bit on crypto because last October, when the structure, Genius Act passed and the SEC made stablecoins legal tender, something really crazy happened. The Stability Act, or the Clarity Act, as it was called then, looked like it was gonna close by December. So here we are in October, with the Cantor Conference in October.

• 23:58Speaker 01

  October 20th was the date, I think. And the word on the street was that within six weeks, that we were gonna get the final act for crypto, which was gonna be the structure, Clarity Act. So all of the sovereign wealth funds that we index with on the equities started to say, okay, we're gonna do some work on preparing for which positions to put on in crypto. Which ones do we need to own to actually get exposure to the alpha? The volatility of the market. Do we own Bitcoin? Do we own Ethereum? Do we own Solana? Do we own whatever? Whatever, you know, there's 10,000 coins. And they independently, without any emotion, because there's a lot of emotion in the crypto market,

• 24:43Speaker 01

  a lot of Kryptonians and all that stuff. These guys were just independently saying, we're gonna allocate $500 million into crypto. And their researchers started to go to work. Here's what they found out. You only need to own Bitcoin and Ethereum and you capture 98% of the entire crypto market. You don't need anything else. All the rest is poo poo. So the poo poo coins collapsed. I mean, it was brutal. Some of them went down 80, 90% and they're never coming back because they're poo poo coins. They have no reason to exist and there's nobody going to save them and they have no marketing money to go get the ticker

• 25:25Speaker 01

  that Ethereum gets every day on every cable network in the world that looks at business. And Bitcoin's Bitcoin. So that's very sobering. People lost a ton of money that they're never going to get back on the poo poo scale. So if you're going to get exposure to crypto, avoid poo poo and just simply buy the two that matter. That's what I did. So I sold 27 positions. Gone. Put it into USDC, which, you know, is giving me yield of 3.9% and just bought more Ethereum and Bitcoin. And now it's a very interesting time. Those things have been crushed too. So, you know, I'd call that an alternative too, but it didn't perform as well as gold.

• 26:06Speaker 01

  So, you know, if you think about it this way, for me right now, it's probably 60 equities globally, 20 fixed income and 20 alternatives, including cards, crypto, gold. And that performance has done quite well.

• 26:26Graham Stephan?

  What's an investment that everyone loves right now that you think is going to collapse?

• 26:31Speaker 01

  It's never the one you think, you know, it's sort of the, in fact, that's the great question because it's the reason that you should force yourself into diversification because you think you know, you don't know, but you're right, something will collapse. But because you only own 5% of it or max 20% in that sector, it's very hard for a sector to completely collapse, but.

• 26:57Speaker 00

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• 27:26Speaker 01

  You know, there's been a real correction on a lot of the AI assumptions lately. And some of those stocks have pulled back, but because for me, it's it's just a 5% position. It doesn't really hurt. And yet, gold, everybody got that wrong. And that thing really saved my rear end. Like, look at my gold portfolio, it was insane, the performance.

• 27:46Jack Selby?

  If you had to throw out a guess, though, if you were to speculate, not that people should listen to what you're speculating on, but what would you say could be something people are bullish on right now that you're bearish on?

• 27:56Speaker 01

  I think the disruption that's going to occur in AI around, I would say, financial services. You saw what Jack Dorsey did. He laid off 40% of his people yesterday. He, in a sense, sees financial services. I think that's going to happen again. Now, the weird thing is, the stock price didn't collapse, but the employment numbers did. So it's hard, it's hard for me to pick where AI is going to disrupt next. I would have thought it would have happened sooner, but it's this next year, the year we're in, here we are in February. If we have this gathering again in 12 months, something's going to go down 80%. I just don't know what it is yet, but it will be because of AI's disruption.

• 28:41Jack Selby?

  So I'm curious for you, do you just pop open your brokerage every morning and like dollar cost average?

• 28:47Speaker 01

  No, no, what I do is I mark to market with a dashboard I have. It's a proprietary dashboard, but it takes every single global, because I have accounts in the UAE, in Switzerland.

• 29:02Jack Selby?

  What do you mean a council?

• 29:03Speaker 01

  Well, I have a company called O'Leary Global in Abu Dhabi, and it has investments. So those stocks go up and down on that exchange. So I need to know what they are. And so at 4:05, although, remember, 13 hours ahead over there, I just take a snapshot. I look at it on my phone and I say, I just look for variance. What moved more than 3%?

• 29:30Speaker 01

  And so it flags any position that had more than a 3% move in this trading session. And what's occurring now is there's more and more names every day. There's a lot of vol. Let me give you an example. I'm a shareholder in Circle. You're probably unaware of this. It went up 35% yesterday. That's a lot. Now, why did it go up 35%? Because there's a emotion in the market now that it looks like the Clarity Act is going to clear in the next couple of months, and that solves the issue around interest on stable coins. So boom, I have a big position in that company because I bought it privately years ago. 35% move in one day?

• 30:13Speaker 01

  You don't see that very often, but it, you know, was a huge winner in the portfolio. But my whole point is it's not more than 5%. But that, when you get one 5% position to move 35%, you outperform the market that day. That's what happens.

• 30:28Graham Stephan?

  When do you think the next recession is going to hit? And what do you think is going to cause that?

• 30:32Speaker 01

  I always look at the canary in the coal mine. That's the consumer.

• 30:38Speaker 01

  When the consumer rolls over,

• 30:41Speaker 01

  you'll see it. It'll be three data sets in a row, and that means we're entering a recession. Now, you know, each recession is different. The wild card again is AI. People are saying today because of, you know, Jack Dorsey's thing, the recession is going to be caused by AI. The only problem with that statement is yes, the people that lost their jobs don't have the same earnings power, except how do you know they're not going to be sucked up into another sector? You don't. And so will AI self-correct the economy by making it more productive with higher free cash flow? Like even in our companies in the last two years, just the private ones like,

• 31:22Speaker 01

  you know, Boost Oxygen or Blue Land detergent or Hello Prenup. You know, these are all small cap businesses. Cash flows are up 20%. Why AI?

• 31:38Graham Stephan?

  Now, I'm sure I don't have to say this, but cryptocurrency has taken over the mainstream within the last few years. But despite this, many platforms are still incredibly difficult to use. There's unfamiliar apps, never-ending security loops and confusing layouts that make it impossible to know which platforms you could trust.

• 31:55Jack Selby?

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• 32:04Graham Stephan?

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• 32:12Jack Selby?

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• 32:21Graham Stephan?

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• 32:26Jack Selby?

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• 32:33Graham Stephan?

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• 32:57Graham Stephan?

  What do you think of the wealth tax? Because Jack, we were having a discussion earlier, believes that it might be a good thing.

• 33:06Speaker 01

  No, no, Jack, you're going to hell for saying that.

• 33:08Jack Selby?

  But there is, there is an argument to be made.

• 33:11Speaker 01

  No, there isn't. It's un-American. It's, it will destroy the fabric of the economy, punishing wealth and success.

• 33:18Graham Stephan?

  Well, it's not punishing because they, they already have billions of dollars.

• 33:22Jack Selby?

  Right. The difference between having $5 billion and then let's just say a 10% wealth tax, you know, $4.5 billion is not quite significant.

• 33:32Speaker 01

  It's just the idea that you're made a, a promise to come to America as an entrepreneur,

• 33:41Speaker 01

  to achieve the American dream. And then some arbitrary politician randomly decides.

• 33:49Speaker 01

  We're going to appropriate that from you. We're going to steal your wealth just because we feel that a 10% wealth tax is appropriate.

• 33:59Graham Stephan?

  It's not really stealing, it's redistributing.

• 34:02Speaker 01

  You're gonna go to hell too. Like, like both of you are going to hell. I feel sorry. I mean.

• 34:09Jack Selby?

  Well, we've never made any real money before.

• 34:10Speaker 01

  I've heard that word before in Cuba, in North Korea, in Russia.

• 34:16Jack Selby?

  It just hasn't been done right.

• 34:18Speaker 01

  They're all sh- balls now. How about Venezuela? They redistribute all the time to corruption. It's a sh- ball.

• 34:25Graham Stephan?

  Assuming it goes to corruption, but if it doesn't.

• 34:28Speaker 01

  No, the point is.

• 34:30Jack Selby?

  We're not very corrupt here in America.

• 34:31Speaker 01

  No, because we have laws and we abide by them. But one of those laws is you can't steal people's money. So this idea of a wealth tax is going to be litigated right to the Supreme Court and it's going to lose because it's un-American. And there is no such thing as too much wealth because it all goes back anyways. The guy dies or the woman dies that has that wealth. And then we hit it again with state tax. You get it back and during their lifetime, they should be able to enjoy their success. You know, unfettered because they took the risk to create, you know, what people keep forgetting on this issue. And Elon Musk is often used as the example, you know, nearly the wealthiest man on earth now.

• 35:17Speaker 01

  How many jobs has he created? How much tax has he paid? I mean, if we didn't have him, would there be Starlink? Would there be, you know, Tesla? No. Would there be all this innovation in robotics? No. Let's punish him for his success. Let's make damn sure.

• 35:34Graham Stephan?

  I think he would be fine with a hundred billion dollars. He's not off the streets.

• 35:37Speaker 01

  He wants to use that money to, he's, he lives in a shack somewhere. He doesn't care.

• 35:43Jack Selby?

  We're totally okay. We don't actually leave a wealth tax. Yeah, yeah, no. We're just trying to bait you. Yeah.

• 35:48Speaker 01

  You know, I get it.

• 35:48Jack Selby?

  We just thought this was a fun discussion.

• 35:50Speaker 01

  You're not going to hell then, and you're lucky.

• 35:52Jack Selby?

  Just trying to hold back the laughter.

• 35:53Speaker 01

  The whole issue is, and he said this publicly, I need that capital to deploy the next mission. And he's turned it from Mars to being the moon, just in the last two weeks. I want, I want to give him as much money. Because if you look at executional skills, show me anywhere on earth where there's a person like that. And thank goodness, he doesn't live in Russia or in China or in, you know, North Korea. He's here in America because he wants to pursue the American dream. The reason those countries, you know, you think about even Europe. If you have a great idea and you're sitting in France, you get on a plane and you go to Texas. That's where you make it happen.

• 36:32Speaker 01

  Even as far back as the V2 rockets, when they were, you know, Germans, they came to America and set up NASA. We bring the geniuses here because they want to live in freedom and they want to be rewarded the American dream. Look, I'm very, I'm very stalwart on this. I'm very focused on it. And when I see bad policy, I rage against it.

• 36:55Jack Selby?

  I got a question. Have you ever met Elon Musk?

• 36:57Speaker 01

  Yeah.

• 36:58Jack Selby?

  When's the last time you met him?

• 36:59Speaker 01

  Uh, Mark Burnett's, uh, Christmas party. It has to be at least four years ago, um, because Mark used to do a Christmas, he doesn't do it anymore. But we used to do a Christmas party for all of the Shark Tank, uh, you know, it's television companies. It was a great party on the, on the West Coast and everybody showed up. I, I'm, I was talking to him and Lady Gaga at the same time. It was just wild.

• 37:20Jack Selby?

  So Elon was talking to Lady Gaga. What are they talking about? What do they have in common?

• 37:26Speaker 01

  It's, it's interesting because I found her fascinating too. She was really interested in business and we were talking, I think we were talking indexing. Um, you know, I think she's, I think she's, it's very random. And yeah, I mean, I, I really enjoy, you know, and I'm thrilled to be part of the acting community now. Cause that's as eclectic as hell. I mean, these parties are incredible and they're just so interesting because I'm so used to financial services to find myself acting in a feature movie. And then, you know, hitting the parties and all the rest of that.

• 37:57Jack Selby?

  Okay, but people also, the viewers out there that don't attend the Hollywood parties have a very controversial opinion on the Hollywood parties. How have?

• 38:05Speaker 01

  I get it, but what you find out is those people, um, and I'll, I'll speak on their behalf. I thought the same way about Hollywood parties, complete bull. Then I actually went to work on a feature film for eight months. They work like hell. Their working conditions are brutal. They work 18 hours a day.

• 38:29Speaker 01

  You know, when you're shooting on the streets of New York or in Tokyo, I mean, it is exhausting and you're living in a ball trailer with a porto can toilet. It sounds glamorous to make a movie. It is not glamorous. It is not at all. It's hard work and now I get it and I have a new respect for them. So for anybody listening, don't make an assumption that a Timothy Chalamet runs around making movies and lives like a king. He lives like shit. Like, you know, it's shit. It's really, really hard. And it's exhausting because you gotta get through that seven pages of script. And if you have to stay there till six in the morning, you're gonna stay till six in the morning. And then you gotta get up two hours later and do it again.

• 39:13Jack Selby?

  So when they were casting for the movie, they said they were looking for a real asshole. I'm curious if that's how you see yourself.

• 39:19Speaker 01

  No, I just tell the truth. Some people don't like it. It goes right back to the beginning of this narrative we had about, you know, what happened on CNN. Some people just go crazy when they hear the truth. And I don't care. Listen, the thing is, and I've said this to a lot of my students, if you try to live your life pleasing everybody, you're gonna fail. You cannot make everybody happy. If you decide to take on a leadership role in business, you are definitely not gonna make everybody happy. If you want to get and be part of the narrative on policy, you are definitely not gonna make everybody happy.

• 40:01Speaker 01

  The only people you need to keep happy are your 20s. Most people only have 20 people in their lives that mean anything to them. Their family and maybe an extended family and some close friends. There's not 200 people that you spend every day with. Everybody else, your role is not to make them happy. It's to tell them the truth and make sure you don't do anything that you'd lose their respect. I mean, I think people dislike me. Many do. But I believe that most of them respect me, even though they don't like me. You know, that's because I haven't done anything to do. I never lie about anything. Sometimes that causes a lot of problems.

• 40:42Jack Selby?

  And have you ever taken your honesty too far? Like, has there ever been a point where you were too brutally honest or too blunt about something that the outcome was just objectively bad?

• 40:53Speaker 01

  Yeah, that happens. I mean, yes, I have. I can think of... You know, recently, Billie Eilish comment. I didn't mean it to be, I think she's a great artist. That I listen to her music all the time, but I didn't like what she was doing in terms of being political at an award show. That really, she really got pissed off at me, but.

• 41:17Jack Selby?

  What is it like to have Billie Eilish mad at you? Is she like DMing you like?

• 41:22Speaker 01

  Yeah, I don't know. I mean, it's, you know, she had, she had a bunch of actors come out in her support, and I think that's great. I don't dislike these people. Most of them I haven't even met. So it, but it to me is, you know, when you talk about Indigenous rights, something I know a lot about because they're my partners in data centers. What people don't understand about First Nation, all over North America, very simple to understand this, there is no border for them. They have the First Nations rights. They drift over the Canadian American border anytime they want. They don't recognize the border and we allow them to do that. They own the water rights to many, many places in America and Canada. It's their water.

• 42:07Speaker 01

  And so they're going to be your partners. And they are my partners. And I, I don't like to hear anything said about them that isn't true. And so I stand up for, for my business partners and I claim why I do it. And, you know, it's sort of important because they need to hear that signal from me that I am truly looking out for their interests. Because it's in my best interest that they do okay. And so when we build a data center there, because they have, we need water. We can't do it without them. So it gets into that. That's how complicated my life is. I'm always thinking about, all right, what's, what's factual here? Now, if that pisses somebody off, okay.

• 42:49Speaker 01

  But you know, I don't think I'm a bad guy. I'm just telling the truth. It's still the truth today.

• 42:53Jack Selby?

  Do you think that as time has gone on, that the truth has become more elusive in terms of people now prioritize feelings over some form of objective reality? Like back in the day, you could be blunt, you could be brutally honest and people were more okay with it. But as time has gone on, it's it's not as acceptable now?

• 43:12Speaker 01

  I think the answer to that is yes, that's true, but not for me. I don't care. I just don't care. I am, I'm gonna tell the truth every day. And it's just, and the reason you need to do that is if you only tell the truth every day, you're never gonna have to remember what you said. It's still gonna be the truth tomorrow, you know? And I really, and I really think there's something else going on. Just look at what's occurred on the Epstein files now that we have AI. Millions of pages, okay?

• 43:44Speaker 01

  If you're in that, it's not about the criminal prosecution. It's destroyed hundreds of people's careers just to have their name in it. In some cases, maybe it's fair. Some cases it may not be. I don't know the details, but every day you see fall from grace from somebody canceled. Because, you know, they obviously didn't think that through. You have to live your life every day thinking, is everything I did today? Am I, am I comfortable with it? Was I honest? Did I do anything that I'd be ashamed of tomorrow? Because with AI coming and social media, everything you do is seen by everybody all the time.

• 44:28Speaker 01

  So it goes back to the truth thing. I would argue the best thing you can do is tell the truth. Because if it's not true, you're going to get fucked 100% and they will cancel you in two seconds.

• 44:40Jack Selby?

  Did someone like lie to you early on? Or did something happen for you to have such a strong emotional attachment towards the truth? Because I remember the last time-

• 44:48Speaker 01

  Yeah, my mother caught me in a lie when I was like 15 years old and it was, it was a bold faced lie.

• 44:53Jack Selby?

  What was the lie?

• 44:54Speaker 01

  I'm trying to remember. I was in high school, I think.

• 44:58Speaker 01

  It's about smoking drugs, I think. You know, I rolled a big fat joint, smoked it and she came home early and she could smell it. And, you know, at that time I was smoking drugs. I don't do drugs anymore, but you know, experimenting with a lot of stuff back then. And she said, you should have told me the truth.

• 45:15Speaker 01

  Because I've caught you in a lie. And, and she said then, look, if you only tell the truth every day, you'll never have to remember what you said because I just caught you lying to me. And it really had an impact on me. It really hit me. And I thought, she's right. And I remember, you know, it was in the kitchen. I remember it crystal clear. And ever since then, I've tried the truth. It's worked for me, but shit, it's got me a lot of trouble too.

• 45:39Jack Selby?

  What's the hardest truth you've had to deliver? And what's the hardest truth you've had delivered to you?

• 45:44Speaker 01

  It's always when I'm terminating somebody. You know, I have such a massive organization now. I'm very fortunate in business, but I really require executional excellence. And, you know, people, when you, you know, we're going back into entrepreneurship here, but when you become a leader and you take other people's money and you start investing it, they make the assumption that you are going to protect their capital and give them a return. And in order to do that, your mandate is to find the very best, best people to work in these companies. And so my job is to find the right CFO, find the right CEO, find the right tech person, find, and then you have to not only do that, gel a team. The team has to work together.

• 46:28Speaker 01

  So my strategy has always been, let's hire someone for six months first, see if it works on a consulting basis, a 30% higher salary and no stock options or anything. And then if it doesn't work out on their resume, it simply says, I consulted with one of the O'Leary Ventures groups and I just moved on. But the hardest thing is, is when you, when you finally come to the point where you've got to make a change, you have to tell them why. You've got to be honest. And that's tough. It's really tough, but you also have to be fair. I think, oh, you know, it's got to be thousands of people now that I've let go, you know, in my career, but every one of them got a great exit package. I've never heard anybody bad mouth me afterwards saying, he wasn't fair to me, man or woman.

• 47:13Jack Selby?

  What's the harshest truth that someone's ever delivered to you?

• 47:16Speaker 01

  Yeah, I would say my stepfather said to me, and I was, I was very much interested in becoming a photographer because I was working as a cameraman at that time before I was going to college. And he sat me down and said, I'm sorry, but you're just not good enough. You don't have what it takes to survive against the level of quality that's out there. You're just not good enough. And That was a real stunner and he was right. He was right and it forced me to go back into college and I did a business degree. And then the first thing I did to spite him was to start a production company. And I, but I made sure I didn't, I wasn't the chief photographer anymore.

• 47:58Graham Stephan?

  So you still kind of listened.

• 47:59Speaker 01

  Well, but I, and I sold that was my first deal. It's called Special Man Television. It did all the NHL Saturday programming, but I hired a great cameraman and hired, and then I learned how to edit myself. I was a good editor, still am. But it, it's sort of, it's, it's very hard to have somebody tell you you're just not good enough when it's true. It's true. He was right. Some people can't accept that. They can say, well, no, I'm going to get better. Executional skills vary on different mandates. You may be very, very good at one thing and not in another. And the real strength in life is figuring out what you're not good at. That's more important than knowing what you're good at so that you don't try and do things. I'm really logistics. It bores the crap out of me.

• 48:43Speaker 01

  Making widgets, shipping widgets. I've always had a partner that does that in every business I've done. I'm the marketing sales guy. That's, I'm really good at that and I know that and I can measure that. But when it comes to like, you know, where do we inventory our widgets? I don't give a, go figure it out. And I'm willing to give up equity to people who can solve that.

• 49:02Graham Stephan?

  So in terms of telling the truth, you recently upset a lot of people saying that the movie Marty Supreme could have saved millions replacing the background actors with AI.

• 49:10Speaker 01

  Yeah. Well, that is.

• 49:11Graham Stephan?

  Why do you think that upset so many people?

• 49:12Speaker 01

  So let me tell you what I learned about that. I'm going to modify that statement a little bit because I experienced it myself. In a, in a scene where you have, let's say 30, we had scenes with 250 extras. And you're shooting it and there's people in a, in a cafe or walking or bringing over, you know, a drink and, or there's a narrative. When you have an interaction with an extra, that can't be AI. I would have thought it could have been, but it can't be because what I realized is. The real magic of filmmaking are the mistakes you make. So I gotta retract that statement a bit.

• 49:56Speaker 01

  Where you can use AI would be like Ben Hur had cutouts in the stands when it was shot in the 60s. They couldn't put 1,100 people in blazing sun for 12 hours. So they made cutouts. When we used to do hockey shots, we had blow up dolls. We had the first row with live people in the in the hockey arena. And then everybody else was a sex doll. We just bought and blew them up. And because you're the motion is that's very blurry in the background. That's going to be AI. You're going to get backgrounds that are AI, but not where there's interaction between the actors. That's never going to change. And I realized why. I mean, you know, I said that uninformed. So I've changed my views because I've actually done it.

• 50:41Jack Selby?

  What did you end up doing with all those dolls?

• 50:43Speaker 01

  We what we would do is we'd pop them and just throw them out.

• 50:47Jack Selby?

  You didn't donate them? Donate them?

• 50:49Speaker 01

  You blow them out with a CO2 cartridge. They come with a and you know, they always have really big lips.

• 50:58Speaker 01

  And we put like baseball hats on them and stuff.

• 51:01Jack Selby?

  You should have donated them, really.

• 51:03Speaker 01

  And then we we shoot the scene and then someone would run out there with a knife and just chop them up. Take the hats off.

• 51:09Jack Selby?

  Take a few of them home too.

• 51:10Speaker 01

  It's really hard. It takes a long time to get the air out of them.

• 51:14Jack Selby?

  Oh, so you just got it.

• 51:16Speaker 00

  This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed sponsored jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed sponsored jobs. Get a $75 sponsored job credit at indeed.com/podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed sponsored jobs.

• 51:46Speaker 05

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• 52:15Speaker 01

  Yeah, there was actually a Shark Tank deal last year. It's called Gertie. This guy comes out and he says, he shows a video of a dog that, you know, your security cameras? You leave and the dog starts howling, "Ooh", because he's got anxiety the owner's left. So he gets a sex doll, blows it up, and puts his jacket on it so his smell is on it, and sticks it in the living room, sitting there like this. And the dog just lies down beside it all night.

• 52:44Jack Selby?

  I thought you were gonna go somewhere else.

• 52:45Speaker 01

  No, no, no. And so what he decided to do was take out the big lips part, because that's what the sex dolls have, and put his girlfriend's face on it. Her name is Gertie. We put it on Shark Tank. It was the stupidest thing I'd ever seen, but it was so crazy that I invested in it. And it's been one of my best deals. You can go look at it, gertie.com, and you can buy a doll for your cat, your dog, or turtle, whatever it is. And the animal will eventually, because it has legs and it's got arms, and you put sweater on it. And when you leave, they just say, "Oh, there, he's still here." It works.

• 53:19Jack Selby?

  So when you say it was one of your best investments, what does that even mean? Like, how long have you held on to it? Are you taking distributions? How much did you put in? What's it worth now?

• 53:28Speaker 01

  Adventure investing, you don't treat it like a normal investment because you don't get anything back till your capital's returned. It's not return on capital. It's return of capital. If you give somebody $500,000... And you never get any cash back. You've made nothing. You can't argue that the, you know, private company that is a consumer goods service company, your risk is really high because they may never figure out how to get their customer acquisition costs down. That's why I came up with the royalty idea. In the beginning, everybody thought it was, you know, bad and they abused me for it. Now every shark wants to do royalties because what you're doing there is you're slowly getting back your principal and you don't make any money till the first dollar after all your principles return.

• 54:09Speaker 01

  So my most successful deals are ones that have strong cash flows that can pay the 7% royalty. And eventually we sell the company and some like deals like Blue Land, for example. My cost base on Blue Land is zero. All my capital's back. The business is probably worth today 150 million. I bet you it's going to sell for half a billion because it's growing like a weed. And I own, I don't know, three or 5% of it, but I have no, all the capital's returned through royalties. That's a great deal. That's how you should structure venture investing.

• 54:43Graham Stephan?

  How do you think AI is going to change the structure of your businesses in the future?

• 54:47Speaker 01

  I don't think it's going to change the structure. It's going to change which ones I invest in because if you're not using AI tools now for customer acquisition, I'm not investing in you. In this season of Shark Tank, the first question I'm asking is what's your customer acquisition cost and which AI tools are you using? Because I use them all. We know every single tool out there. I mean, what people don't realize is only five vertical stacks of AI that cost billions to maintain and develop. But off of those verticals come very interesting applications that you can buy a subscription for. For example, let's say like in my case, I've got 12 terabytes of video and photographs, 12 terabytes in the cloud right now.

• 55:29Speaker 01

  That's because I've been doing television for 25 years. Every show, every photo, every, you know, that thing doing this wide angle shot, all of that sitting in the cloud. How do I index that? How do you even remember where that stuff is? And so recently, I found a tool, a very, very specific tool, that if you put it in a giant database in the cloud and you let the AI look at every frame of every photograph and every video and every film, it takes a long time, a couple of months.

• 56:05Graham Stephan?

  Hmm.

• 56:06Speaker 01

  But, once it's indexed, you can say, "I recall a picture, and I was on a paddleboard in Jamaica, and a dolphin looked up at me and somebody took a picture." Bang! There it is, on the screen, with the index to where it is, or if it's a video, how long it is, what the resolution is, all of it, just sitting there. And you can just say "click" to download. That, you know how much time that's gonna save? So that's a tool. That really saves time. So we're able to do these real deep dive social media things now for our own platform of, you know, young Kevin, old Kevin, Kevin with a beard, Kevin with full hair, all that stuff. Because all of it is at a second away from us.

• 56:51Speaker 01

  And the guys that do that are over in the UAE.

• 56:54Graham Stephan?

  Do you think you could be replaced by AI?

• 56:56Speaker 01

  I think I already am. I have an AI Kevin. My wife can still discern the difference on a screen, but in about a month, she won't be able to. Because the only thing now that is the slight tell is the voice intonation. And there's a new model, just came out last week, that you have to basically let your phone listen to you for about three days. Just record your daily life for three days and let it learn off that. Because in a three-day period, you go through everything: sleep, you go through waking up, wake-up voice, dinner voice, you know, drinking wine voice, coffee voice, all of it. And the tool then applies that to your AI model.

• 57:39Speaker 01

  That's an agent, I have a Kevin O'Leary agent. And I'm able to, you know, it's remarkable. I That agent's incredible and we're starting to use it.

• 57:49Graham Stephan?

  Do you think that could eventually replace your work hours? That you just have your AI Kevin go and go to work for you? Answer emails for you, take phone calls for you? And if it gets to a certain point, then it alerts you and say, actually Kevin, you should hop on this call just to make sure. But like it does 90% of the work, the filter.

• 58:08Speaker 01

  I think we're way off on that because I realize my best ideas actually happen very early in the morning when I'm on my bike riding at, you know, 6:45.

• 58:22Speaker 01

  Something will hit me like that whole idea I'm so excited about because when I leave here, I'm on my way to go see the first iteration of the Parisian diamond necklace. And so I was on my bike in Miami and I was thinking about that Kobe card. And you know, Logan Paul, he's good friends with, you know, I've done his podcast and I like the guy a lot and another guy involved and I was thinking, how could I, how could I raise that? How can I make a piece unique like my watches? And while I was on the bike, I have Nicole Weiss, she's the head of high jewelry for

• 59:06Speaker 01

  LVMH and I just called her randomly and I said, Nicole, listen to this. She said, I love it. It's crazy. How would, how would we know how thick the card is? How would we know all that stuff? So we went to work on it and we just got in a group chat and we designed this thing based on how that card looks and which diamond should be where. But we had the full support of LVMH and I thought to myself, would AI ever do that? Nah, probably not. They wouldn't have the same reason to do that. I'm not sure that pure innovation comes from that. I think implementation, execution.

• 59:47Speaker 01

  Comes from AI, but I think the human being is so random in its thinking process that you're still gonna need it. That's my iteration of it anyways, because I use a lot of AI tools now. And I'll give you an example. When one of my students, and this has been talked about a lot, sends me, you know, an answer to a question or an essay, I just look at it and say, AI slop. Like, you get to see it. It's not their voice. You know, the person, they write this thing and say, you know, I just say, look, do it again. I don't mind you using AI to start it, but don't, like, this is bullshit. And

• 1:00:31Speaker 01

  I'm not even using an AI, you know, discovery tool, because you have tools to discover AI in text, too. So I'm not, we're very, I think we're in the first inning, and maybe it gets better and better and better, but I don't think it's gonna be creative enough. Because people are trying to do this now. Let me give you an example. Write me a song with a country-esque kind of middle eight. And it writes it. Sounds like shit. I can tell right away that it's an AI song. Write me a song that sounds like Steely Dan, you know, younger Steely Dan, second album kind of thing. Sounds like-

• 1:01:13Graham Stephan?

  Some of them sound incredible, though. I've been listening to Korn, the band, as gospel-

• 1:01:19Speaker 01

  Right.

• 1:01:19Graham Stephan?

  And soul. It's amazing. And I'll play that on repeat. It is so incredibly good.

• 1:01:24Speaker 01

  Yeah, I get it. But, you know, if you listen to the real thing, and you find the nuance and the little distortion and the mistakes, make it better, I think. Because I've listened, you know, I have a lot of music, and I try, I listen to a lot of new bands, and I listen to the AI bands. I mean, they sound so formulaic. They don't have-

• 1:01:46Speaker 01

  You know, what makes great, I listen to a lot of jazz. If you go back and listen to even the 50s records, Kind of Blue is a classic. The first version of that album was a mistake. It was about 10% slow. They recorded it on a broken recorder. They had two machines in the room and they released the one that was slow. Because when people tried to play against it, they said, I got to tune down here. What the, this isn't in tune. Then they found the master tape that wasn't slow and they put the album out again. And yet you listen to those two things. They are definitely not AI. There's all kinds of little nuances and mistakes in there. And I think you could argue, well, maybe AI can make mistakes too.

• 1:02:30Speaker 01

  But that's where I think the creativity is lost. I don't know. Show me a commercial success so far with AI. People want to go to a concert and listen to a machine play something to them.

• 1:02:42Graham Stephan?

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• 1:02:54Jack Selby?

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• 1:03:16Graham Stephan?

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• 1:03:25Jack Selby?

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• 1:03:33Graham Stephan?

  So if you're ready to find a turnkey new construction home, try out Lennar Investor Marketplace with the link down below in the description.

• 1:03:39Jack Selby?

  Thanks again to Lennar for sponsoring the Ice Coffee Hour and back to the episode. This episode is in partnership with Airbnb. So Graham and I just wrapped up a trip. We were in Austin for a few days. We filmed episodes with Togi, Chris Camillo and Caleb Hammer. And honestly, every time we're on the road, we're staying at homes on Airbnb. It's just become the default.

• 1:03:55Graham Stephan?

  And here's the thing most people don't think about. When you're the one traveling, your place back home is just sitting there empty. And that's a real missed opportunity.

• 1:04:03Jack Selby?

  Whether you're gone for a long weekend or a few weeks, you can list your space on Airbnb and let it work for you while you're away.

• 1:04:09Graham Stephan?

  If you've ever thought about hosting but weren't sure how to manage everything from the road, Airbnb now has the co-host network. You can connect with a vetted local co-host who has real hosting experience and can take care of the day to day for you.

• 1:04:21Jack Selby?

  A co-host can manage reservations, handle guest communication, and even provide onsite support so you don't have to think about it while you're traveling.

• 1:04:27Graham Stephan?

  So instead of your home sitting empty, you could be generating some extra cash, whether that helps you cover the next trip, your flights, or it just goes towards something that you've been putting off at home.

• 1:04:36Jack Selby?

  I actually listed a spare room in my house on Airbnb and I was genuinely so surprised how easy it was to set up, how seamless the entire process was, and it actually made me some pretty good money. I would actually recommend this to anyone out there that wants to make a little extra cash on the side. It's honestly phenomenal. If you're thinking about hosting but want some help getting started, find a co-host at Airbnb.com/host. I think a lot of people are probably wondering about finances as well because people see you as phenomenal entrepreneur, a great investor. I'm curious, who do you think is the best investor of all time?

• 1:05:10Speaker 01

  Well, the thing about that is it's only numbers because who made the most money? Remember, investment's very binary. You either make it or you lose it. And clearly Warren Buffett and Charlie Munger, no one has been close to their success and they had a very simple model: cash flow. Charlie, he could never be bullshitting to anything that didn't have cash flow. He didn't believe in anything that didn't have cash flow. And he would just say, no, no, no. He was the no in Warren's yes. And they needed each other in the beginning. And then they got into their own discipline of, you know... Buying things that have very long-term, stable cash flows. And that ended up being the right thing to do.

• 1:05:55Speaker 01

  The other thing I've learned is just buy the market. Like betting on, on hedge fund guys and, um, stock pickers. There aren't too many good ones.

• 1:06:05Jack Selby?

  So to the average person out there that's watching this right now. Let's say they're making $50,000 a year, $40,000 to $80,000 a year, living all across America. How do they go from maybe month to month, not really being able to save too much to then being able to have discretionary spending? To start to live a life of comfort? Like what is, if you could instill one idea, one belief into them that could hopefully bridge that gap, what would it be?

• 1:06:31Speaker 01

  Well, the hardest part of that is the discipline it takes to decide that you're going to put aside 10 or 15% every week. It's so hard to do that because there's always the next pair of sneakers you want to buy that you don't need. People are weak. They don't have discipline. Don't buy shit you don't need. And, and if you look at yourself and see all the clothes you have, you don't wear. You bought them because you had a whim for it or something, but you basically wear the same two pair of jeans and five T-shirts. It's crazy that you would take that money and put it into something you're going to throw away in 20 months. When you could have put it into the market. And the way you put it in the market, if you don't understand the market, you don't have a brokerage account. Download one of these apps that does it for you on your phone.

• 1:07:14Speaker 01

  Link your bank account to it and just transfer in 10% each week. Obviously I have, the one I like is Bean Stocks, but it's not the only one. There's plenty of them that'll do it for you. I like them really simple. And then if you start doing that, two years later, you'll say, wow, where'd this money come from?

• 1:07:33Jack Selby?

  At what income is it just impossible to build wealth?

• 1:07:38Speaker 01

  I would say probably under $35,000.

• 1:07:42Speaker 01

  That's tough if you live in a major city because you're being forced to spend, you know, 1,200 to 1,500 on rent, which is very, very hard. But even in that, the discipline of not overspending because you're going to get yourself, the real task there is not to go into credit card debt. It's tough.

• 1:08:00Graham Stephan?

  What jobs do you think those people should take?

• 1:08:02Speaker 01

  Oh, I think the job that gets you the most money now is if you have talents in social media for customer acquisition. I used to pay those guys 48 grand a year and now they're 250,000 because you can measure their work based on customer acquisition every week. So most of them become contractors. You know, they make half a million dollars a year because they know how to take content, turn it into a 59 second ad on social and acquire 200 customers. That's a very specific. So remember, everybody say have to be an engineer, an engineer, an engineer. Now you want to be an artist again. Write stories, acquire customers, know how the social media platforms work, know how to post on TikTok versus LinkedIn versus Twitter versus Instagram.

• 1:08:45Speaker 01

  Those people in their early twenties are so valuable now. So if you know how to use your phone, somebody wants to hire you.

• 1:08:54Graham Stephan?

  So if you were to go back in time with the specific skillset that you currently possess, is that what you would do?

• 1:08:59Speaker 01

  Yeah, I would use my editing skills to make 15s, 30s and 59s. And I would basically say, look, pay me, you know, a hundred bucks for each customer I acquire for you. I'd make millions. I mean, I know how to do it.

• 1:09:14Graham Stephan?

  Now, you previously said that someone should spend 30% of their time outside of their comfort zone.

• 1:09:19Speaker 01

  Yeah.

• 1:09:20Graham Stephan?

  What does that look like for you?

• 1:09:22Speaker 01

  For me, that's going to be acting. I'm here in LA, working on my next project. The difference between feature film and television is massive. Most people don't think there's much of a difference, but there's a massive difference. It's completely different skill set. And I want to do more of it. So for me, it's going to be shoot a film every year. I don't mean, you know, a television series. I mean, a feature film that's going to get theatrical release. So that's, everybody wants to do that. I'm going to let my performance be the judge for those agents, directors, producers, casters that have seen Marty Supreme. Nobody knew how it was going to come out for me.

• 1:10:04Speaker 01

  I think I've done, you know, no one's telling me I shit the bed on it, that's for sure. So I'm going to take that tape. That's my, my only role ever. And I'm going to say, look, I'd like to do this again. I want to be the antagonist. I think that role is far more interesting. It's far more interesting to be the bad guy because there's so many places you can go. There's so many twists and turns in being the antagonist of any story. Every story has a hero and has a bad guy. I want to be the bad guy. So that's, that's what I'm looking at now is various opportunities for bad guy.

• 1:10:40Graham Stephan?

  Why are you so drawn to the bad guy?

• 1:10:42Speaker 01

  It's so interesting. You know, you're reading these scripts. I've read a lot of scripts lately and I look at them and I say to the director, that's not what the bad guy would say. This is what he would say. And they say, no. So I find that with the writers and the directors, you get a lot more latitude to creating your role as the bad guy. Because the hero always has an outcome that's hard to change. They're going to kill the bad guy. They're going to get the girl. They're going to, you know, save somebody or something. You can't change that outcome. That's the core of the story. You know, if it's, if it's a big action movie, it's an Avenger type thing. They got to save the world.

• 1:11:27Speaker 01

  But the way the bad guy during his interaction, he can go everywhere. And so you, you basically, what I find, this is my own observation, is when you're the bad guy, you get a lot of latitude in every scene. Because when we were doing Marty Supreme and I, with Ronnie Bronstein and Josh Safdie, who were co-wrote it, I'd say, guys, guys, guys, he's gotta say this, not that. And they say, no, okay, let's shoot it that way, too. So it was sort of like the whole vampire thing. Remember that at the end of the movie? I don't know if you've seen it. We dreamt that up on my, on my dock at my lake house because I, we're at the end of the movie and I'm looking at the three of them. Eli Bush was there and I said, guys, do you think if I was the richest guy in, in America,

• 1:12:12Speaker 01

  I would let this little screw me over this way? Do you think there'd be a chance that would ever happen? They said, what are you saying? I'm saying, there's no way it ends this way. This kid has to die. They said, can't die. You know, we have a different ending. I said, well, then I'm gonna bite his neck. And they said, what the, what are you talking about? I said, yeah, I'm gonna tell him I'm a vampire. And they looked at each other and said, whoa, that's crazy. Let's go there. So it was sort of like bring the dark arts into it. Make him think if there's even a 1% chance that this could be true, that I'm a vampire. And that's where the line came out, I was born in 1601.

• 1:12:54Speaker 01

  That gave Milton Rockwell the satisfaction that he held the dark arts over this kid for the rest of his life. And you could see, you know, Shalomay played it so beautifully because we did that in Japan. He freaked out. He kind of smiled and went, whoa, like, that's crazy. And it was crazy in the moment we shot it. But to me, that's why you want to be the antagonist. You can explore many different directions where you can't if you're the hero.

• 1:13:26Jack Selby?

  How many times did you have to do that?

• 1:13:28Speaker 01

  Scene?

• 1:13:28Jack Selby?

  Yeah.

• 1:13:30Speaker 01

  That's a one take, that one.

• 1:13:32Jack Selby?

  Just one take. They didn't, they didn't want to put you guys through that.

• 1:13:37Speaker 01

  We did many scenes that were 50 takes, but that one was so crazy, that was one take.

• 1:13:41Jack Selby?

  I'm curious, on Marty Supreme, how much did they pay you?

• 1:13:45Speaker 01

  Oh, I don't even know. I mean, I couldn't buy protein with what they paid. I mean, it was like, it was, I'd never acted before, you know? The only question they had, are you a member of SAG? I said, yeah. Because I think I was the last guy cast. They couldn't find, you know, Milton. They wanted a real bad guy. And he just called me out of the blue and said, look, you gotta come to New York. I said, no way. I'm sitting on the dock. I'm relaxing up here. I'll send you my plane. I'll pick you up. You come up here. We'll do it tomorrow morning. And they said, shit, yeah, let's do it. And then I really got into it.

• 1:14:22Speaker 01

  There is a weird story about that, though, that you should know. That script is the size of a phone book, and I hadn't really read it after they sent it to me and I forgot about it. And I left it on the bar. And this guy named Gene McBurney got up at five in the morning. We have a lot of people staying at the lake. It's a big party every night. And he got up five o'clock to watch the sunrise and he took the script with him, not knowing what it was or anything about the project. And he read it.

• 1:14:49Speaker 01

  And by the time I got to about 10:00 in the morning, I went outside and he was sitting there saying, Kevin, have you read this thing? I said, no, this is the craziest, most insane story I've ever read. It's whoever wrote this is a very sick, demented person. But you gotta be Marty. You know, you've got to be the guy that...

• 1:15:11Speaker 01

  What he meant was, you've got to be the antagonist to Marty. You've got to be Milton Rockwell. And I said, I gotta read this, right? He said, you gotta read it. And I read it and I realized what he was talking about. He, he saw the force, the force of good and evil between Marty and Milton as being the fulcrum of the whole story. And...

• 1:15:34Speaker 01

  If you're not Marty, you gotta be Milton. That was his point.

• 1:15:37Graham Stephan?

  I'd like to see you as a Bond villain.

• 1:15:40Speaker 01

  Yeah, I mean, you know, Bond is not gonna be produced for years, so I have to do other stuff. I mean, for me, it's sort of, here's the thing I learned. This is tough. I came in at the top. I worked with an A-plus writing team, an A-plus director. A24, the number one hot team in Hollywood right now. Buena Paltrow, huge budget movie. Like, I don't know what it is to work on a dogshit movie. How am I gonna do that? I've gotta get another fantastic movie. I gotta find another fantastic director. I mean, there's a lot of crap that's made. I don't wanna work on that. I wanna work on the El Supremo stuff.

• 1:16:21Speaker 01

  Now, that sounds ridiculous to make a demand like that, but I don't actually need a job. So, I wanna do it 'cause it's extraordinary. I wanna do it because they're considering risking a part on me based on the merit of my work. I wanna do it 'cause I'm a good actor. Not, I don't, you know, it's not like I need, I'm not a starving artist. That's the problem.

• 1:16:45Graham Stephan?

  Are you gonna get royalties from this?

• 1:16:50Speaker 01

  I said to my agent, who I like a lot, their UTA, a guy named Jay Suresh, I said, Jay, why don't you let me negotiate the deals? I'll handle everything. The agency can still get its piece. He said, what are you, out of your mind? I said, no. There's one thing I learned about Hollywood that a lot of people don't know.

• 1:17:10Speaker 01

  When you're negotiating on behalf of one performer, let's say it's me, and you're dealing with a network or a producer, or you also have in your portfolio many other artists. So, let's say a certain television network wants to hire me.

• 1:17:30Speaker 01

  And they're not meeting my agent's price, or whatever it is, because in the end, these guys are about the money. It may go down like this. Give him what, give Ollie what he wants, and we'll get you X, Y, Z for that movie you're doing in your studio. I can't do that. They can. And all of a sudden, bingo. Everybody's happy. That's what these guys do in Hollywood. They trade assets all over the place. It's a dirty secret, but that's exactly how it works. So to be successful, you have to be under the wing of an agency that has a lot of assets, and they're worth every cent. Because you can't. I remember in season four of Shark Tank,

• 1:18:13Speaker 01

  walking into whoever the president of ABC Television was then and saying, don't need an agent. I'm going to handle this myself. Just you and me. He said, no, not doing that. I don't want to taint our relationship because we're going to have a bloody negotiation in season four. The show was on fire. It was going geometrically. And I said, well, why don't just let me handle it? I'm a big boy. I have thick skin. He said, no. I've made a few calls. You're going to get a call.

• 1:18:42Speaker 00

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• 1:19:12Speaker 01

  A guy named Burkes. And then he's going to take you into meeting a guy named Jay Suresh in about an hour. I said, I don't, I don't need no stinking agent. They said, yeah, you do. And I think you're going to like these guys, and I think you're going to sign with them. And that's exactly what happened.

• 1:19:28Graham Stephan?

  What's been your toughest negotiation?

• 1:19:31Speaker 01

  It's not around television. It's with government in what I'm doing in real estate. There's so many moving parts. And when you're building a $20 billion data center.

• 1:19:49Speaker 01

  It's tough. You've got to negotiate everything. And you need the senators, you need the governor, you need the mayor, you need the feds, you need FERC, you need everything. And I'm the guy. Sometimes it flies in there and sits down with the staffers of the senator. I say, here's how it has to happen. And those are very difficult negotiations because they're public in some sense. They're complicated, the dollars are huge, and you can't it up. Every piece has to work. I've never worked this hard in my life, but the deals we're doing now, I'm now the largest in North America company with land under agreement for data center development.

• 1:20:34Speaker 01

  Twenty-six thousand acres. That's a lot. That's one hell of a ranch.

• 1:20:40Graham Stephan?

  What's the biggest screw up that you've had during a negotiation?

• 1:20:44Speaker 01

  That's a good one. Very, in the last forty-eight hours, there is a card out there that we made a deal on. And the guy that sold it, who I did not know, it turns out what he did is he, and I don't know this for sure yet, but I think we're going to find out this is the case. He used my name to trade it sideways to somebody else. What's going to happen in the next few hours to him is he's not going to like it. It's going to be raining from the sky, lawsuits from hell. Because in the market, it's like the market in New York for diamond merchants.

• 1:21:29Speaker 01

  There is no paper. There's an agreement, there's a handshake, and that stone is sold. It never goes sideways. And should you ever breach that hundred-year-old trust, it's been generation, generation, you're banned from the industry forever. In cards, when you make a deal, because you're working with people all over the world, when you finally come to a price and you say, are we done? And the other side says, we are. It's sold. It's over. And in this case, I've never seen it happen before, but he reneged. And I consider this contemporary art, modern art.

• 1:22:12Speaker 01

  The piece is now tainted because from my legal perspective, I own it. The other buyer, everybody that touches that card is going to know that I'm going to litigate for my legal claim. So that card is going to be very hairy for the next few years. Even though it's a very valuable card, it's probably going to become very famous because of the litigation, not the card. Everybody that touches that card, I'm going to sue them. Anybody that tries to be an agent, I'm going to sue them. Anybody that tries to auction it, I'm going to sue them. As far as I'm concerned, that's my card because the transaction took place.

• 1:22:49Jack Selby?

  Were you on the phone or in person with this person? You guys agree verbally on a price, shake hands.

• 1:22:54Speaker 01

  One of my partners was on the phone and there was a witness as well. Now, because he's reneged, the only legal recourse we have is to bring a claim. I'm going to let the process run its course, but every other. I know every buyer of cards of this price on earth. I know who they are. And they also know who I am. And they know that I don't let this happen to me.

• 1:23:23Jack Selby?

  What was, what was the card?

• 1:23:25Speaker 01

  I can't say, but you will know, you will find out soon enough.

• 1:23:28Jack Selby?

  Why not get it in writing at that point?

• 1:23:31Speaker 01

  There is no writing on cards. That's not works.

• 1:23:34Jack Selby?

  Why? I feel like just with any other thing that you would buy, you would get a contract, you'd sign it.

• 1:23:38Speaker 01

  The way it works is you're on the phone with someone in Malaysia or the Philippines. The card is, you've been discussing it for sometimes six months. You don't have an agreement on price. You're watching the markets move. You finally come to an agreement on price.

• 1:23:56Speaker 01

  The trust is unbelievable. You wire thirteen million dollars to that person. While your representative is right at the table and they pass over the card and it's clam like that when they see the money in the bank. That's it. You take the card, you leave. You go get it graded or you put it in a vault. You get back on an airplane and you fly with it, whatever you have to do. That's how it's done. The trust is immense. It's just, the market is a well-known market. You just don't breach. You don't do that. Nobody does that. It's, nobody does that. It's just, it's like a diamond merchant. If you did that in the streets of New York, your family would be banned for life and the

• 1:24:40Speaker 01

  next generation. You just don't do it. I was stunned. I couldn't even believe it. I mean, I just said, no.

• 1:24:46Jack Selby?

  This is after you already sent money?

• 1:24:48Speaker 01

  No, no, no, no. We were, we were actually in the process of setting up a global, live broadcast.

• 1:24:56Jack Selby?

  Wow.

• 1:24:57Speaker 01

  To, to, to actually, with a network I won't mention. But we were already, and from Paris, you know, another frame was being built for that card. And all of this was arranged over a one-month period. And everybody was flying to this location for the shoot, which was gonna happen at five in the morning, eight o'clock, East Coast time, New York time. And then, of course, in the afternoon in Europe, it was gonna be worldwide. And this guy just went AWOL. We thought something bad happened to him. It turns out he was trying to trade it to somebody else after an agreement had taken place. I mean, it's not gonna end well in terms of how tied up that card's gonna be.

• 1:25:40Speaker 01

  It's, I don't know what the resolution's gonna be, but for the next three, four, five, six, seven years, I think it's radioactive waste.

• 1:25:47Jack Selby?

  Alongside cards, in alternative investments, you have quite a few watches. I'm curious, first of all, when you check the time, which wrist do you look at?

• 1:25:55Speaker 01

  Well, left wrist is always local time. Right wrist is wherever, you know, the, the majority of the phone calls are gonna be this day. In this case, it's New York. So it's New York time on the right, LA on the left right now. And I do that when I'm in Dubai or Switzerland, and sometimes I have three time zones.

• 1:26:11Jack Selby?

  And so as a watch fanatic, let's say someone has a budget of one thousand, five thousand, we could throw ten in there.

• 1:26:19Speaker 01

  Yeah.

• 1:26:20Jack Selby?

  And then 25 and maybe 100,000. What is the perfect watch at those different prices?

• 1:26:25Speaker 01

  Yeah, I get it. So, you know, it's a great question because I'm going to tell you a really interesting story about this. About five years ago, maybe it's six now, this woman came out in a set of Shark Tank and she's, can I talk to you for a second? I said, sure, you know, we break between hits and we get about 20 minutes while they set up the next pitch. And she said, we're having a problem with the two watches. I said, what's the problem? She said, nobody can afford them. This show's about inspiration, about aspiring, about getting. They start on the carpet, they want to become sharks. They want to become sharks. So you have to stop wearing watches, no one can afford it. On your left, you can wear whatever you want. On your right has to be an entry level watch. So what's entry level?

• 1:27:09Speaker 01

  She said, how about 200 bucks? I said, I don't wear $200 watch. She says, you do now. From now on, you're going to wear something that people can afford. And I thought, wow, that's, but, you know, anyway, she was right because I immediately called Teddy Baldasar. And we started doing videos together of every price point, under 200, 200 to 1,000, 1,000 to 2,000. And Teddy introduced me to all these incredible watchmakers that make these amazing dials for like 1,700 bucks. But if you're buying a piece, it's to shorten this narrative here because we've been going on for so long. But here's what I tell parents. They're always calling me up saying, my son is graduating, my daughter's graduating, what do I do? There are certain truths.

• 1:27:53Speaker 01

  Number one, Tudor. You cannot go wrong with a Tudor. It'll last your whole life. You know, the parent company's Rolex, people get it, but Tudor's different. It's very, very entrepreneurial in terms of case materials. You can get silver, you can get ceramic, you can get carbon. They got beautiful, beautiful cases. And, you know, the Black Bay is an amazing, it's the precursor almost of, of almost every Rolex style. It's beautiful. Remember that these companies have been around a long time. Number two, Grand Seiko. Unbelievable quality. I mean, just the spectacular watch. And these are sub $7,000. They're going to last a whole lifetime, no question about it. There's other places to go.

• 1:28:40Speaker 01

  But those two represent, in my view, some of the greatest value on earth. Japanese watchmaking, it's Credor, they cost a fortune, but they're also owned by Grand Seiko. The best advice I give is you go online and just look at any Teddy Baldazar, Kevin O'Leary video and you're gonna find 400 ideas. And I wear those a lot.

• 1:29:05Jack Selby?

  Google estimates your net worth to be 400 million. I don't think that's the case. I think that you, based off of what you've said, have more. Is 400 million accurate?

• 1:29:15Speaker 01

  You know what I learned, again from my mother? Never boast about money or one day you won't have any. I never talk about my net worth. You know, it's, it's, it's, I just think it's the worst thing you can do. It's almost bad karma. Like, look at how much money I have.

• 1:29:32Jack Selby?

  Well, it doesn't have to be boasting. It could be an offense.

• 1:29:35Speaker 01

  But I'm not like that. I just, I don't, you know, I don't need more money. I need more time. That's the way I look at it. I don't want to with karma. I just never talk about it. People, I've seen estimates all over the place, but.

• 1:29:46Jack Selby?

  Let me ask you this. What percentage of your net worth would you trade to be 20 years old again?

• 1:29:51Speaker 01

  Oh. Oh, wow. That's a hell of a question, eh? I mean, I wish I could be 20 with what I have right now. I mean, what the things I could do with? The trouble is I wouldn't know anything. That's the big dilemma about, about this idea. It's what I know today and my experiences that make me what I am. And I wouldn't change anything. So I wouldn't even.

• 1:30:18Jack Selby?

  Let's say you retain all of that and you just.

• 1:30:19Speaker 01

  Yeah, but you just can't.

• 1:30:21Jack Selby?

  Get 20 years old again. But you have to, you have to say, I'm gonna give 90 plus percent.

• 1:30:25Speaker 01

  But the risk of that, it's such a, it'd be a great movie script. The risk would be you get to go back, but you start again. What's the outcome? What would the outcome be? You get more life. You'd be like a vampire. You go back to 20, but you don't know what the outcome could be. You could have a horrible outcome. I like this outcome. I've, I earned it. I made it myself. I made all those mistakes and look at where I, I remember the first day of shooting Marty Supreme across from Timothy Chalamet with all those extras. And for a moment, I thought to myself, how the hell did I get here? That was amazing. How that's happened? And it's accumulation of all the things that occurred during your life that got you that point. So I wouldn't go back. I wouldn't do it. I wouldn't trade it for anything.

• 1:31:07Jack Selby?

  So some more rapid fire questions. What was your personal best Shark Tank deal?

• 1:31:12Speaker 01

  Oh, uh, base pause, cat DNA testing, insane return.

• 1:31:17Jack Selby?

  What's the worst pitch you've ever seen?

• 1:31:19Speaker 01

  Oh, I've seen plenty.

• 1:31:22Speaker 01

  The, the, I've seen, I've seen a pitch where a woman sang to a water cooler and said she could divide the, the water into three elixirs that you could bottle and sell for $25. One that, uh, solve for jealousy, one that made you fall in love when you wanted to, and one that made you more productive. And I said to her, you know, you sound insane. She said, if I came here and told you I had an elixir full of cocaine and you drank it, would you invest in that? I said, no. Well, that's Coca-Cola.

• 1:31:54Speaker 01

  Touche.

• 1:31:56Jack Selby?

  Bitcoin price year end 2026?

• 1:31:59Speaker 01

  Uh, probably around here because I don't, I'm not sure it's going to react until the Clarity Act is, is, if, if the Clarity Act, I'm going to answer it this way. If the Clarity Act, uh, is approved, Bitcoin will probably go back to that $100,000 range.

• 1:32:17Jack Selby?

  S and P price year end 2026?

• 1:32:19Speaker 01

  Up 8% from here.

• 1:32:21Jack Selby?

  Gold, buy or sell right now?

• 1:32:23Speaker 01

  Buy.

• 1:32:25Jack Selby?

  Will AI replace more jobs than it creates?

• 1:32:28Speaker 01

  No, it's going to create more jobs. Everybody, everybody's got it wrong. It's just like, oh, you know, television can destroy radio. No, it's not. We just don't know what the transition is going to look like. AI is going to be such a powerful tool. It'll create new industries we haven't even thought of. That's what's gonna happen.

• 1:32:42Jack Selby?

  Should a 25 year old buy a house or invest in the stock market with that money?

• 1:32:47Speaker 01

  Um, I would buy a house. Um, and I would pay that mortgage off as fast as I can. It's, it's, it's always proven to be the best way to make money in America.

• 1:32:54Jack Selby?

  At what net worth does life fundamentally change?

• 1:32:57Speaker 01

  Five million. Liquid, liquid.

• 1:33:00Jack Selby?

  What would you say are the main four tiers of wealth? Where if you hit a certain amount, life

• 1:33:04Speaker 01

  Well, I tell everybody this. You should strive very hard, if you're an entrepreneur, to have $5 million in T-bills. Not in anything else, just T-bills. Making 3.82% this morning. You know you've made it and you've safeguarded your family for the rest of your life if you can get $5 million liquid in T-bills. Most people that consider themselves very successful entrepreneurs do not have $5 million liquid in T-bills. They don't.

• 1:33:33Jack Selby?

  But what net worth should you be at to justify $5 million in T-bills?

• 1:33:37Speaker 01

  Well, you should be at... The first thing you should do is get to $5 million liquid. Be worth $5 million liquid. That's far more valuable than anything else. Liquidity with wealth is actually a superpower. Most people say, "I'm very wealthy," but they couldn't raise $1 million by 2 o'clock in the afternoon if they tried. It's tied up in all kinds of things they think are worth a lot until the shit hits the fan. The plan is, if you're an entrepreneur, the hardest thing is to make the first million. Really hard. And when you make the first million, put it in T-bills. Just as hard, but not as hard, is to get to 2 million. 2 to 3 is actually quite easy because you've figured something out. But where you get undisciplined is you start buying shit you don't need

• 1:34:22Speaker 01

  because your mandate is to get to 5 million liquid. You have to have 5 million liquid to call yourself a successful entrepreneur. And I don't care who disagrees with me, they're wrong.

• 1:34:32Jack Selby?

  But if you have a net worth of $5 million, why would it all be in T-bills instead of having it in S and P, in international index funds?

• 1:34:38Speaker 01

  Because whatever happens, you're safe.

• 1:34:42Speaker 00

  This episode is brought to you by Indeed. You're ready to level up your business, but the pressure to find the right person to make that happen is intense. Indeed-sponsored jobs can help carry the load. It boosts your job post to help it reach quality talent fast. Cut through the chaos with Indeed-sponsored jobs. Get a $75 sponsored job credit at indeed.com/podcast. Terms and conditions apply. Hiring now? Then this is a job for Indeed-sponsored jobs.

• 1:35:11Speaker 05

  Now, more than ever, we need someone on our side. But Rob Whitman? Whitman's votes drove up costs, cut Medicaid, and risked 350,000 Virginians' healthcare to pay for tax breaks for himself and his donors. He's not on our side. Shannon Taylor will fight corruption, cut taxes, and bring down costs. This November, vote for Shannon Taylor. She's for us. Paid for by HMP, the House Majority PAC dot com. Not authorized by any candidate or candidate's committee.

• 1:35:41Speaker 01

  And your family.

• 1:35:42Jack Selby?

  So you say get to 5 million T-bills, and then anything after that?

• 1:35:44Speaker 01

  After that, after that, stick it in. And I do go into stocks, go into alternatives. The nut is $5 million.

• 1:35:52Jack Selby?

  And so the next net worth with the highest quality of life change would be what?

• 1:35:56Speaker 01

  You know, once you get to 50, you don't even need any more money. I mean, people say, I want to buy a yacht and all this crap. But I didn't, my life didn't change after I had $5 million very much. I mean, it's just, you know, I have a lot more now, but it's... Other than watches, I don't do crazy stuff with money.

• 1:36:15Jack Selby?

  What's one stock everyone should own?

• 1:36:18Speaker 01

  Oh, that's, there's... It's the index. That's what you should own. Because you can't ever get it right.

• 1:36:26Jack Selby?

  Timothy Chalamet, is he a better actor or ping pong player?

• 1:36:29Speaker 01

  He's a better actor. There's a lot of CGI in that. He can play ping pong, though. He's a pretty good guitarist, too, by the way. That kid's pretty talented.

• 1:36:37Jack Selby?

  Secret to building wealth in one sentence?

• 1:36:39Speaker 01

  Discipline.

• 1:36:41Jack Selby?

  That was one word. That's pretty good.

• 1:36:42Speaker 01

  Yeah.

• 1:36:43Jack Selby?

  What's your number one regret?

• 1:36:45Speaker 01

  I don't have any. I wouldn't change a thing.

• 1:36:48Jack Selby?

  Do you still want more money? And if so, how much?

• 1:36:50Speaker 01

  No, I don't want more money. I'm very fortunate to get more money because I really focus on what I do. But I don't need more. I need more time.

• 1:36:57Jack Selby?

  Would you retire for $10 billion post-tax right now?

• 1:37:00Speaker 01

  No. No, no interest in that.

• 1:37:03Jack Selby?

  If you were to leave the viewer with one piece of advice, it doesn't have to be money, it doesn't have to be finance, it could be anything, what would it be?

• 1:37:08Speaker 01

  Figure out what signal in your life and focus on that and avoid the noise.

• 1:37:13Jack Selby?

  Cool. Kevin, thank you so much. We'll link to your info.

• 1:37:15Graham Stephan?

  Thank you very much.

• 1:37:16Jack Selby?

  I know you gotta get going. Really appreciate it.

• 1:37:17Speaker 01

  Thank you.

• 1:37:18Jack Selby?

  Like, subscribe.

• 1:37:18Graham Stephan?

  Thank you, guys, for watching.

• 1:37:19Jack Selby?

  Until next time. By the way, if you enjoyed this episode, we just posted our next one early for members. So if you click the join button, you could literally begin watching our next episode right now. Really hope you enjoy it.

• 1:37:40Speaker 05

  Now, more than ever, we need someone on our side. But Rob Whitman? Whitman's votes drove up costs, cut Medicaid, and risked 350,000 Virginians' health care to pay for tax breaks for himself and his donors. He's not on our side. Shannon Taylor will fight corruption, cut taxes, and bring down costs. This November, vote for Shannon Taylor. She's for us. Paid for by HMP, the House Majority PAC dot com. Not authorized by any candidate or candidate's committee.