🔮 “New Richest Human” — Oracle’s 40% surge. Ralph Lauren’s AI nepobaby. “Got Milk?” 30th b’day. +Pokemon Card investors.

0:28This is Nick. pop business news stories for today's show, and we're excited to hit them with you. So Jack, what do we got for our first story? For our first story, the biggest surprise on Wall Street yesterday was Oracle. The stock surged 40 % the moment the market opened. And that 40 % surge means we have got a brand new richest human on earth. For our second story, can we talk about Ralph Lauren? Please. The inventor of the polo shirt is at an all-time high thanks to its new AI wardrobe. Honestly, Jack and I aren't shocked because Ralph Lauren is actually one of the most innovative brands in fashion history.

1:04And our third and final story, Got Milk. It's arguably the most successful ad campaign of all time. And 30 years after the first Got Milk Milk Mustache, we are having another real milk moment. Wait, did you call it a mustache? Ah, the emphasis was on the wrong syllable, Jack. But yet is before we hit that wonderful mix of stories. Fantastic mix of stories. Love the mix today, Jack. Stocks are surging at ATHs, all-time highs. Crypto is crushing it right now, also at an all-time high. Gold too, but the best performing asset on earth right now is fictional. Because the best performing asset is Pokemon trading cards.

1:44Get this, since 2004, Pokemon cards, if kept in mint condition, have seen a return of 3 ,821%. It's pokey cards. We're up nearly 40x right now. That's eight times better than the S &P 500 over the same period. I mean, Jack, if you bought Facebook stock on its IPO day, you would have been better off buying Bulbasaur. It's true. By like 2x, actually. How's your portfolio, Greg? Well, I'm long Pikachu, so yeah, it's strong to quite strong. One mint condition Pikachu was actually bought for$5.3 million. Holy Charizard! So according to Wall Street Journal reporting, people are putting their real money into fictional characters.

2:25The WSJ interviewed a Pokemon collector in Arkansas who is buying up cards to eventually pay for his five kids to go to college. What about baseball cards? Yeah, those are up too. But Pokemon characters have less risk than baseball cards. True. Because Charizard isn't getting injured anytime soon. And Squirtle won't get a DUI or ruin the whole card's value. Our biggest regret, it's that we snorlaxed on this opportunity 20 years ago. Jack, you got to catch them all. That's not a catchphrase, though. That's actually an investment thesis. To be clear, not financial advice, just financial regrets.

3:01Jack, let's hit our three stories.

3:1650 % that's a fat tip. T-Boy City on your at list. If you know, you know, cause we ready to go. We can't wait no more. So just start the show.

3:28Start the show. First, a quick word from our sponsor.

3:39Monarch. Yeah, it is. You know, my first money lesson, it was where to put our lemonade stand. I was wondering, it was on the Upper East Side. Do we do it on Lexington Avenue or Park Avenue? Wait a second. New York City has lemonade stands on the sidewalk? They didn't. We were pioneers, Jack. Lexington Avenue is more commercial. Park is more residential. So what did we learn, Jack? Families are willing to pay more for lemonade. So you set it up on Park. Yeah, we did it on Park. Besties, no one gives you financial lessons in life. You end up figuring most of it out as you grow up. But we love Monarch because it's like a financial advisor in your pocket.

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4:33Because we pioneered it for him, Jack. Resties, write your own story with Monarch. Use code T-Boy at Monarch.com to get your first year of Monarch Core half off at just 50 bucks. It's 50 % off your first year at Monarch.com with code T-Boy. Decagon. Yetis, someone needs to make a rom-com about falling in love with your customer support agent. Do they, Nick? It's probably going to start Kate Hudson, Matthew McConaughey, and Decagon. I think what Nick is getting at is that Decagon helps companies create personalized, concierge-style customer experiences with AI agents across chat, email, voice, and SMS.

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5:34So Decagon solving customer problems, it's like living happily ever after in a Hallmark. Yeah, rated R for really good customer service. Ready to transform your customer support? Go to decagon.ai slash tboy to get a personalized demo and see what Decagon can do for your team. Check Decagon out at decagon.ai slash tboy. That's decagon.ai slash tboy. Nick, did you see Liquid IV teamed up with RingPop? I did, Jack. And honestly, it's one of those collabs where you immediately think, how has nobody done this before? I mean, ring pop cherry is already iconic. My sons love ring pops, by the way. I give it to them at the beach.

6:11It occupies them for about an hour. But now it's a sugar-free liquid IV flavor too. Ah, it's not just a fun flavor. It's still the same liquid IV hydration formula that hydrates faster than water alone, has three times the electrolytes of the leading sports drink, plus eight vitamins and nutrients. I've been throwing one of these in my water before the gym and before bed pretty much every night if I sweated that day. Way more fun than drinking plain water. Probably for workouts, travel days, hot days. Honestly, anytime you know you're probably just not drinking enough water. So if you're looking for an excuse to actually stay hydrated, this is a pretty good one.

6:43Check out the new Liquid IV sugar-free ring pop cherry at liquidiv.com. For our first story, wild surprise on Wall Street yesterday. Oracle stock jumped 40 % after the most bullish earnings report we have ever heard. And that means Larry Ellison, someone you've probably never heard of, has become the world's richest person. Yetis, here's the question everyone on Wall Street was asking yesterday. Is Oracle the new NVIDIA? Based on their latest earnings, apparently. Yeah, because on Tuesday, the software brand Oracle said in the last three months, They signed deals worth$300 billion. I'm going to sprinkle on some context.

7:29You're going to have to, Jack. $300 billion in three months, that is six times more revenue than they've ever done in a full year. Oracle booked more money in the last three months than Uber has made in its entire life as a business. Here's a quote from the CEO yesterday. We signed four multi-billion dollar contracts with three different customers in the first quarter. Okay, that is so much money. Jack and I just have to ask, um, who are these three companies exactly? Who drops$100 billion on an order? Is it Richie Rich, Taylor Swift, and the Monopoly man? Well, we did find out. The first customer is OpenAI.

8:06And the other two are probably Meta and XAI. They're renting Oracle servers to compute the AI needed to answer all those queries you're typing into those chatbots. Because as we told you before, Yetis, in the AI gold rush, you wanna sell shovels. And Oracle just sold$300 billion worth of shovels. Yeah, I love that shovel analogy. You got another one though, Jack? I do. It's a game of musical chairs in tech right now. But instead of chairs, AI companies are fighting for the scarce servers. And Oracle's got a bunch of them. I like what you did there. Now, Basties, as a couple of retired ex-finance guys, can I say retired?

8:41I am tired, but I'm not retired. Jack and I also want to share one huge financial caveat here. That$300 billion isn't cash in the bank yet. It's just contracts with Oracle to get paid over the next five years. So pause the pod for a second, Jack. Is it common for companies to boast about money that they won't actually be paid for five years? No, especially in industries like AI, which are so volatile and unpredictable. Just look at NVIDIA, the leader in AI. They don't even do financial forecasts beyond one quarter from now. And yet Oracle just did a financial forecast 20 quarters out. Five years.

9:20Oracle literally just answered the question, where do you see yourself in five years, even though nobody asked them? A bold promise indeed, but investors ate it all up. The stock jumped up to 40 % yesterday, which is the best day for Oracle stock in 33 years. They licked it all up. So Jack, what's the takeaway for our buddies over at Oracle? Larry Ellison just passed Elon Musk to become the world's richest man. Now, Yetis, if you have heard of Larry Ellison, it's probably related to his colorful personality, his tabloid headlines, or his goatee. Okay, this is our take, but his facial hair is the same as Iron Man.

9:57And he's also got a black turtleneck, Steve Jobs style. Okay, Larry Ellison is so rich, he owns an entire Hawaiian island with a Four Seasons hotel on that island that pays him rent. I've been, it's awkward. Last year, Larry Ellison's wife used his money to pay a high school quarterback to play on the University of Michigan to boost the recruiting class. Okay, and then Larry Ellison's son took more of his dad's money and bought an entire media company, Paramount. But Larry Ellison is also a Silicon Valley legend. Because not only did he found Oracle 48 years ago, he still owns 41 % of the company.

10:33That's wild. He still owns nearly half the company. He put his money on the line to build a boring server and enterprise business, but it is paying off massively in the AI age. He also crucially hired Saffir Katz to be the CEO in 2014, and the stock has nearly 10x'd since she came on board. And with Wednesday's 40 % stock surge, Oracle is now worth nearly a trillion dollars. And Larry's 41 % stake is worth$400 billion. Which means Larry Ellison just passed Elon Musk to become the world's richest man. The servers are boring, but the equity is exciting. For our second story, the hottest fashion brand in the world right now, it's shockingly Ralph Lauren.

11:19They don't have Sydney Sweeney or Travis Kelsey. True, true, true. But Ralph Lauren has David Lauren. Yes. A tech early adopter. Yetis. Oh, I'm sorry. Pause. Are you going to wear orange? I didn't know you were wearing orange. Jack, you know it's New York Fashion Week. Is that what you're really going to wear today? Orange is the new iPhone color. I figured it was on trend. It is New York Fashion Week, so don't be surprised if you see Miranda Priestly strutting around Soho, but then gird your loins. Because 2025 has been an ugly year for fashion because of the trade war. LVMH, their stock's down 10%.

11:54Abercrombie, they're down 30%. The Gap, they're flat. But there's one exception, and it's wearing a pink cable knit popped collar. Lovely. It's Ralph Lauren. Ralph Lauren. Because Ralph just announced revenue rose 14 % last quarter. The stock is up 30 % this year. To an all-time high. Now, you'd think that Ralph Lauren and its iconic Americana style would be the target for anti-USA sentiment from trade war opponents. But you'd be wrong because sales in Europe and China surged for Ralph Lauren as well. Apparently, polo shirts are more important than geopolitics. Jack, I believe we've said before that nothing transcends treerifs like a pleated khaki.

12:34We have not, but we just did. I knew something was off. Now we have, now we have. But besties, the story here that fascinated us actually goes deeper than a cashmere cardigan. Because Ralph Lauren is the ultimate early tech adopter in the fashion industry. That's right. This week, Ralph launched Ask Ralph, a conversational AI stylist in the Ralph Lauren app. So instead of whipping out your phone to Google what pairs well with my double-breasted polo blazer, you can just ask Ralph. They actually used Ralph Lauren's real Ralph, real input for this AI bot too, didn't they, Jack? Yeah, because Ralph Lauren isn't Tommy Bahama.

13:09It's actually a real person. Yeah, and this Ralph bot will now say it's okay to wear white after Labor Day, just like the real Ralph Lauren would. Although Ralph did partner with Microsoft and OpenAI to build Ask Ralph. However, Yetis, as Jack and I dove in T-boy style, we discovered Ralph Lauren actually has a long history of embracing new technology really early. Ralph was the first major American fashion brand to attach QR codes to labels that we never ended up using. In 2010, Ralph Lauren hosted a holographic runway show straight out of Star Wars. In 2015, they invented a$300 smart polo shirt with sensors to track your body's biometrics.

13:46Oh, and in 2019, they created an augmented reality lens on Snapchat. Eat your heart out, Everlane. But before all that, in the year Y2K, Ralph Lauren was one of the first luxury fashion brands daring to sell their product online. Polo.com. One of the very first e-commerce websites. They actually almost shut it down because they didn't get orders over$50. Like everyone was afraid to give up their credit card info. Well, no one had ever done it online. Yeah, it was freaky. So besties, add it all up and Ralph Lauren is the surprise early tech adopter of the fashion industry, and it's all thanks to one man.

14:23And that one man is not Ralph Lauren. No. It's another Lauren. So Jack, what's the takeaway? Real person for our buddies over at Ralph Lauren. Ralph Lauren is a defense of nepopreneurs. Yeti, guess who was behind all those innovative risks over the last 25 years? It was Ralph Lauren's son, David Lauren. From the website to the QR codes to the current AI chatbot, David Lauren pushed Ralph Lauren forward. And it got Jack and I thinking, you know, Nepo babies get a tough rap and Nepopreneurs do too. They're the founder's kids who grew up with the business and got a cush job right just handed to them.

15:02But growing up inside the company can be a real advantage actually. Because these Nepopreneurs, they know almost in their bones what is best for the brand. And if the brand runs in your blood, you also have an emotional desire to see it succeed that non-family members don't. Also, if expectations are higher, maybe you find a niche that you can focus on that's different from your parent or your siblings, and you excel at it. Yetis, in our other show, The Best Idea Yet, Hermes, Harley-Davidson, L.L. Bean, Jacuzzi, all these companies had midlife crises but got saved by neppopreneurs, the children or the grandchildren of the founders.

15:37And now Ralph Lauren does too. The stock is at an all-time high, thanks to the son who drove the company into the 21st century. Everyone rips on Nepo babies, but Ralph Lauren shows they can actually bring someone no one else can to the table. To the table that their dad paid for.

15:58Now, a quick word from our sponsor. Scribe. Yetis, one thing we've noticed is that companies rarely hit a wall because they don't have enough people or budget. More often, it's because the way work actually gets done lives in someone's head. People end up doing things differently, and when someone leaves, that knowledge, it goes with them. That's exactly the problem today's sponsor, Scribe, wants to solve. Scribe is a workflow AI platform trusted by 94 % of the Fortune 500. It captures any workflow in real time and automatically turns it into a step-by-step guide. No manual writing or manual screenshots required.

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18:08brand. Visit cash.app slash legal slash podcast for full disclosures. For our third and final story, the most iconic ad campaign in history just turned 30 years old, Got Milk. And now the Got Milk milk mustache is coming back for Gen Z. And once again, milk is hot. But Jack, in order for us to tell this story, let's go back to 1995. Could you please set the scene for us? eBay had just been founded in Silicon Valley. Friends had just debuted on cable TV. And we were all singing Gangster's Paradise by Coolio. And also every word was getting an E in front of it because that was the thing to do. Yeah, email, e-commerce, eBay.

18:52We could go on, but we won't. Because that same year, Big Dairy paired together the two biggest words in ad history. Got Milk. Got Milk. It's a question, I think. It is. Because at the time, milk sales in the 90s, they were actually slowing down. So the California farmers got together and didn't promote any one milk brand. They promoted the whole milk category. With Got Milk. The very first Got Milk ads, they were focused on FOMO. The concept was life in the absence of milk is not a life you want to live. They showed Cookie Monster in despair as he had no milk to dip his cookies. Existential crisis this is.

19:29Now, eventually, Got Milk expanded nationwide and they launched the Milk Mustache. And those ads were strategic because they barely showed the product. Who was only the upper lip of a celebrity from Michael Jordan to Britney Spears to Kermit the Frog. Every celebrity. You made it when you got a Got Milk ad. You couldn't open a magazine in the 90s without seeing the Fresh Prince of Bel-Air with the Milk Mustache. Sad fact, wasn't real milk. I think it was like Elmer's glue they put up there. Don't ruin my dreams, Jack. But besties, all of this campaign was funded by dues paid by the dairy farmers nationwide.

20:01And that Got Milk campaign, it was a demonstrable hit. 90 % brand recognition across the United States. It boosted dairy sales from butter to cottage cheese to whole milk to 2%. This is huge because the milk industry had outsmarted Coca-Cola at the marketing game. But here's the news. After 30 years, the Got Milk campaign is coming back with whole milk mojo. Yeah, because in a surprise twist of innovative fate, plant-based milk is now losing to real milk. I never thought I'd see this, but Nick ordered a latte with whole milk, not oat milk. Yeah, it was a double-digit decaf, but I went with the whole.

20:40Dairy milk sales have stopped their decades-long decline, while plant-based milks are actually declining now. They were down 6 % this year. Oatly, which invented oat milk, their stock's down 97 % in 2025. They're getting disrupted by milk, which used to be the disruptee. The disruptor is getting disrupted. And there's three reasons for what we're calling the Moo Milk comeback. First, it's inflation. Oat, soy, almond milk, all of that is an upcharge. Even that almond pit milk we told you about last year. Second is Maha. There's new consumer skepticism of processed foods, but there's trust in cows.

21:15And finally, it's the protein maxing moment, isn't it, Jack? Everyone is pumping or sprinkling protein into their diet. And where does that whey protein come from exactly? Whey with an H comes from cows. It does, and you're doubling up on fair life milk these days. So inflation, maha, and protein maxing. That's why regular old cow milk is making a comeback. And that's why 30 years later, milk has found its mojo and is growing back its mustache. Mustache. Mustache. So Jack, what's the takeaway for our buddies over in advertising? Got Milk invented the meme. Yetis, this is wild. But the ad agency Goodby and Silverstein that came up with the Got Milk idea, they actually hated it.

22:00The ad people at that firm told the New York Times, first of all, it wasn't grammatically correct. And second of all, it was a lazy concept. Yeah, they called their own idea lazy. And you know what? For logical reasons, this Got Milk ad, it should not work. And yet it did. And the reason? We think it was the original template of a meme. It was repeatable, relatable, and in a shareable format. Anyone can wear a milk mustache. The creativity is in the who and what pose. Derek Jeter did it while throwing out a guy at first base. Ultimately, good ads stir up a feeling. And for Got Milk, it was the joy of discovering which polished adult will end up acting like a kid.

22:40By wearing a milk mustache. Simplicity of Got Milk was its success. It's a format, not a message. And that's why it was the first meme marketing. Jack, could you all whip up the takeaways for us for the new Friday? Oracle is the breakout new star in AI, getting$300 billion in orders from OpenAI, Meta, and XAI. And now founder Larry Ellison made$100 billion in one day to pass Elon as the world's richest man. For our second story, Ralph Lauren stock hit an all-time high the same day they launched a style chat bot, Ask Ralph. It's all thanks to Ralph's son, because sometimes Nepo babies bring something to the company others can't.

23:21Although their dad's going to kill them if they scratch the company. Mom, he took my IP! And our third and final story is Got Milk. It's making a 30-year anniversary comeback, and so is Milk. The reason for Got Milk's success? Got Milk was the first meme marketing. But besties, this pod's not over yet. Here's what else you need to know today. First, Klarna, the buy now, pay later darling, went public on Wednesday and the stock jumped 30 % on its first day of trading. We've covered Klarna a few times, most recently with their buy burrito now, but pay for burrito later promotion. Klarna's revenue has doubled to 3 billion bucks since the pandemic, but its valuation has fallen by two thirds down to around 15 billion bucks.

24:03Fun fact, the Swedish co-founders of Klarna got the idea for buy now, pay later while flipping burgers at Burger King. True story. And second, forget Waymo for a moment Zoox is the wild new self-driving robo-taxi that you gotta know Zoox is owned by Amazon And they just launched ride-hail service in Las Vegas on the strip You can book now Now the reason this is so wild Zoox designed their own car And it looks like a giant toaster Partly because there's no front or back Both sides are the same It's symmetrical And there's no steering wheel And no pedals And finally the new batch of emoji have been confirmed.

24:41That's right. Next year, we are getting Bigfoot, an orca whale, a trombone, and a treasure chest. Open treasure chest or close treasure chest? And if you type in killer whale, will the orca show up or do you have to type in orca? The answer to all that is none of the above, Jack, but you can finally text me that you are seeing Bigfoot playing a trombone inside of a treasure chest. I noticed you dodged the orca question at the end there. It's all good. Now Yeti's time for the best fact yet Which Jack and I, like we do every year Wanted to share something we whipped up for you Because it's September 11th Not all our listeners may remember or were around For what happened on September 11th, 2001 Jack and I do, and we were around And we've shared it with you before on this pod We were in 8th grade, Nick was in New York City, I was in Vermont We remember when the teachers came into the classroom To explain what had happened And remember seeing the smoke, you could see it from our school Now it's the 24th anniversary of the attack So we wanted to highlight a particular sign of resilience that we were excited about.

25:39After the two towers fell, downtown Manhattan was a disaster zone. And the discussions at the time, will New York City ever recover from this? More specifically, will anyone ever go downtown to the financial district of Manhattan ever again? Well, guess what? Since the attacks in 2001, the population of lower Manhattan has more than doubled. Get this, from 32 ,000 full-time residents to over 60 ,000 full-time residents. In fact, the Fidei isn't really a financial district anymore. It's a 24-7 living and working neighborhood. It's a win to celebrate. 24 years ago, most thought no one would ever return to those blocks.

26:16But today, it's a thriving family area. And every year on this day, we remember the heroes of September 11th. Yetis, you look fantastic today. And if you're sitting on a Charizard rookie card right now, we know exactly what you should go check out. We did a whole episode on Pokemon. We did. 45 minutes long. Yeah. They used to stand for Pocket Monster. That's why they call it Pokemon. And to get more of those gems, check out The Best Idea Yet, our weekly show for our deep dive on the Pokemon. It was our most requested episode ever, and we delivered. Totally. So go check it out, and Jack and I will see you right back here for The Real Friday.

26:58And before we go, a happy birthday to Yeti Hanna Piazza. Great name celebrating in Long Beach, New York. Happy birthday to Gary Murphy in New York City. And Trish Mahler over in Sussex, Wisconsin has got the best birthday yet. Happy birthday to Rochelle Doka in Jersey City, New Jersey. And a congratulations to Yeti Christina Kong, who's starting her senior year at Warden. And Jack, she's been a legendary bestie for years. And to anyone else who's celebrating something today, make it a T-Boy. Celebrate the wins. This is Jack. I own stock of Amazon. And Nick and I both own ETFs of the S &P 500. There are moments that reveal who we are and who we're meant to become.

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