💰 “$1 Trillion Paycheck” — Elon’s 13-digit incentive. J.Crew’s AI faux pas. US Open’s Cadillac. +Martell baby #2.

0:00This is Nick. This is Jack. Welcome back. It is Monday, September 8th, and today's pod is the best one yet. This, oh, this is a T-boy. The top three pop business news stories you need to know today. Yetis, you look fantastic out there, and we are going to make you the most interesting person in the world this fall. It's great to be back, Yetis. Great to be back with you, Jack. But Jack, we got three fantastic stories for today's T-Boy. What do we got on the show? For our first story, last week, Elon was offered the most insane pay package in history. One trillion dollars. But none of it is guaranteed.

0:41So we will break down how Tesla could make Elon the first trillion dollar man. For our second story, the J.Crew catalog just committed the fashion crime of the year. Because J.Crew used AI to counterfeit itself. And our third and final story is the real winner of the U.S. Open. It wasn't a tennis player, it was a brand. Cadillac hosted the entire U.S. Open tennis tournament, and Jack and I call that the Great Gatsby Strategy. But yet is before we hit that wonderful mix of stories. I mean, Jack, the best mix of anyone right now. Love the mix. We were away for nearly two weeks. And the biggest news on Wall Street over that period, what was it, Nick?

1:25I-B-O. Initial baby offering. Because over Labor Day, Nick's wife, Molly, went into labor. Literally. We had a Labor Day weekend baby. That's what we did. We've celebrated four IPOs on this pod so far. All boys. There's four pod sons so far in the T-boy universe But yet he is Jack and I are proud to announce the first ever unprecedented pod daughter Now in case the analogy is not landing for any of you Nick had a baby girl over our break, okay? Yeah, we did Now Nick, let's jump into the IBO paperwork and talk some numbers What's the size of this new baby? Well Jack, her market cap was 8.4 pounds Okay, okay, pretty good size, that's mid cap I think Like, what was the number of shares issued?

2:13Well, Jack, she's 20 inches long, so that's a lot of shares. Actually, that's large cap for a baby. Now, in the IPO paperwork, I know you were required to list some competitive advantages. Yeah, here's her competitive advantage. She's covered in hair, head to toe. But most importantly, can you share the official name of this brand new human being? Jack, her name is Selena Rose Martell. Selena. Pause the pause. Can you share the wonderful story behind Selena's name? We named her Selena, S-A-L-I-N-A, which is the name of a small island off of Sicily where Molly's family is from. And it's a beautiful, beautiful place.

2:50And you and Molly vacationed there once and reached a big decision while you were on that island. It was the last vacation we did, but we were dicks, basically. That's when we decided to start a family on the island of Selena. Wow. It's a beautiful name for a girl. Thank you, Jack. Now, before we finish, we need an update on the most important executive of this IBO. Mm-hmm. The executive chairwoman herself. Molly, the CEO of the birth. She did amazing, Jack. She's recovering right now, and she's making all the shareholders proud. Molly is the boss of the boss. She owns super shares in this baby, actually.

3:22We've also promoted our son, Maximus, to older brother. It's a big move. Yeah, Molly's got 20 votes per share, everybody. By the way, Yetis, it actually took Molly and I a while to get pregnant. It wasn't an easy process for us. So if you're going through a struggle right now, like we were, we know what that's like, and you will get through it. It's hard, but you'll get through it. But wait, Jack, one second. Do you hear that? Is that coming from 40 Wall Street in New York, New York? That's the New York Stock Exchange opening bell, Jack. And that means Selena Martel is officially trading on the T-Boy podcast.

4:00Besties, we are so pumped to be back. Jack, Jack, what do you say we hit our three stories?

4:33First, a quick word from our sponsor.

4:41Monarch. 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.

5:09Because every minute, it's tracking your savings, spending, investments, and more. For instance, Monarch's goal tracking feature shows if you're on track for that summer trip to Santa Fe. And it tells you what percent of your income is going somewhere that's a surprise. I open Monarch all the time because it takes the mental load off tracking my finances. And whether you're single, you're in a family, or you're dinking it up, Monarch's the way. Our personal fave, the AI Weekly Recap. A once-per-week gut check on what you did with your money. Hey, Nick, you've spent 96 bucks at kids' lemonade stands since July.

5:34Because 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? I was 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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6:36So 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 TBY. Nick, did you see Liquid IV teamed up with Ring Pop? 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.

7:12It 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.

7:44Check out the new Liquid IV sugar-free ring pop cherry at liquidiv.com. For our first story, Elon Musk just revealed Tesla's fourth ever master plan. If Elon succeeds, he'll get the biggest pay package of all time, worth$1 trillion. Trillion. But if he fails, he gets nothing. Nada. Now, Yetis, in order for us to tell this story, Jack, what do you say we travel back to when we were graduating high school? What do you think, man? We have been following Tesla, the company, since Elon Musk published his very first master plan in 2006. Ambitious it was, a four-step plan to transition the world to sustainable energy 19 years ago.

8:31It was a declaration of energy independence. It was way ahead of its time, and he pretty much achieved that entire master plan. That master plan is still inspiring. Make the planet more sustainable by popularizing electric vehicles. He did it. He did. And last week, we got the fourth iteration of Elon Musk's Tesla master plan. So Jack and I jumped in T-boy style, and this one is still optimistic, but it's not about electric vehicles. It's optimistic about AI. Posted entirely on X, the part four master plan introduced a brand new buzzword. Here it is. Sustainable abundance. Don't really know what that means, but Elon's Tesla still pledged infinite growth, AI will solve scarcity, and that robots are freeing up your time.

9:14And because the master plan was so vague and hard to understand, actually, Elon was forced to jump back on X and summarize it in one sentence. Here's what Elon said. 80 % of Tesla's value will come from Optimus, their AI-trained, human-shaped robot. So besties, pause the pod for a second. Here's the plot twist. Elon Musk just renewed his corporate vows, but he switched his devotion from electric cars to autonomous robots. And this pivot for Tesla is partly a recognition of reality. Because, Jack, political support for electric cars, it's gone down in the Trump administration. And consumer support for Tesla's electric cars specifically is even more down.

9:552025 is going to be the second straight year of Tesla sales shrinkage. So it's like Elon jumped on X and asked Grock, hey, Grock, revise Tesla's mission statement, but also make Sam Altman jealous. And that's what he published. But then that's not all, Jack, because then three days later on Thursday, Tesla's RoboTaxi app officially launched with a public waitlist. Tesla's self-driving ride-hail service is available only in Austin and San Francisco so far, but it still hit number six in the app store as people raced to join the waitlist. So add it all up, Yetis, and this was a huge news week for Tesla already, but then this happened.

10:36On Friday, just a few days ago, Tesla announced a$1 trillion pay package for the CEO, Elon Musk. $1 trillion is the amount of money the Tesla board thinks will keep Elon focused and motivated. Well, there is no more money. That is all the money, Jack. If$1 trillion doesn't get you focused and motivated, I think you're an autonomous robot. So Jack, what's the takeaway for our buddies over at Tesla? Is Elon's pay package fair? From a worker's perspective, no. But from a shareholder perspective, yes. Yetis, let's jump into the numbers here. Last month, Elon received a$54 billion bonus. That was the only money he got for his last seven years of work at Tesla.

11:23Elon achieved each and every one of the goals that Tesla's board gave him in his 2018 pay package. And so, he got that record$54 billion bonus. But this new 2025 pay package, it's even more insane. Here are the goals that Tesla gave Elon. Sell 20 million cars. Sell 1 million fully self-driving subscriptions. Increase profits at Tesla by 24x. And finally, no big deal on this last one, make Tesla an$8 trillion company. Now, if Elon can do all of that, he gets paid a trillion dollars in Tesla stock, boosting his ownership stake in the company to 29%. And to sprinkle on some context,$8 trillion market cap for Tesla, that's twice as much as the most valuable company today, NVIDIA.

12:14So Bessie, is that fair? Well, the average Tesla worker gets paid$60 ,000. Elon would be making a million times more pay. Not a million dollars, a million times more money than the average Tesla worker. But from a shareholder perspective, Elon only gets paid if Elon makes shareholders rich. And if Elon doesn't make shareholders rich, then he gets nothing. He literally has no salary right now, no benefits. This bonus is his only pay. So besties, is the wildest pay package in history fair? Well, from a worker perspective, no. But from a shareholder perspective, yes. For our second story, J.Crew just made the worst fashion faux pas of the year because J.Crew used AI to knock off J.Crew.

13:04It knocked off itself. Yes, it did. J.Crew's awkward AI marketing campaign has shaken the fashion industry like a true crime thriller. And we will get into it. But yetis, Jack and I should start with some context here You know, we curate the stories that you need to know, you want to know, and they had no idea about every day So we use dozens and dozens of sources every single morning One of them is a newsletter that Nick subscribes to It's called Blackbird Spy Plane Yeah, it's a fashion journalist and a design scout And it's a hilarious but very insightful fashion newsletter Together, these two are the CIA spies who peek into the wardrobes that you want to own And their latest issue was on the J.Crew collab with Vans Sneakers.

13:48It's a throwback partnership to the 1980s, dripping in corduroy nostalgia. J.Crew posted some dusty old pictures on Instagram that appeared to be from a 40-year-old paper catalog that they made. The whole vibe was cool, classic, cozy, vaguely autumnal. But that's where the fun stopped and the funk started. because Blackbird spy plane whipped out the magnifying glass and looked closely at the pictures. J.Crew's campaign turned out to be a creative crime that made the fashion world gasp. So besties, Jack and I are going to cosplay here as true crime podcast hosts and break down the J.Crew pictures like it was a crime scene.

14:31Jack, exhibit A, what do we see? We'll post the link, by the way, in the show notes so you can cosplay as true crime hosts as well. I'm no sailor, Jack, but doesn't that sailboat in the background look kind of funny? Yeah, the boat is missing a rail. Why does the rail abruptly stop there? Plus, the dock has no fenders. It's going to bump up the boat. And Jack, I'm no J.Crew sales associate, but what's going on with the stripes on this guy's shirt? They totally glitch out. The stripes are all messed up. Okay, Jack, I'm no podiatrist, but is that model's foot facing backwards? Yeah, somebody call an ambulance because his ankle's totally busted.

15:08Okay, to quote Magatu, J.Crew, so awkward right now. J.Crew, disinvited to New York Fashion Week. Bessie's the whole fashion world dragged J.Crew in the comments, outed them for using AI and trying to pass off the photos as real. Now, a few days later, J.Crew edited the caption to reveal who the photographer was for this campaign, and it's a man named Sam Finn. Okay, but this guy, Sam Finn, goes by the name AI Sam. He's an artificial intelligence digital artist living in London. So to sum it all up, J.Crew has a 50-year-old library of real vintage magazine photography from the olden days. And yet they used AI to knock off themselves.

15:53J.Crew used technology to counterfeit old J.Crew for new J.Crew. So Jack, what's the takeaway for our buddies over at J.Crew? Where do we draw the line between Photoshop and AI? Yetis, here's why J.Crewgate is so fascinating. The manipulation of photos, that's been happening for decades now. Photoshop launched in 1990. Since then, every marketing photo that you see has been airbrushed, enhanced, and edited to make it look better than real life. Photoshop is used to adjust contrast, tweak a model's torso, change the colors, and you know what? We accept it. And yet J.Crew used AI to similarly alter reality, but we reject it.

16:38Now Jack and I think the reason for this contradiction is in the origins of the images. Because with Photoshop, the underlying thing being altered is a real photograph. It's an actual photo someone took of real human beings. But with AI, the thing you're seeing is completely artificial. Basically, society accepts a Photoshop tweak, but not AI creating a fake human subject entirely out of nowhere. And that J.Crew didn't disclose that these humans and their ads aren't real made it even more of a niche-niche. So besties, that's the line between Photoshop and AI. And that's why J.Crew's fashion faux pas drew such outrage.

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18:26brand. Visit cash.app slash legal slash podcast for full disclosures. 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.

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19:29That's S-C-R-I-B-E dot H-O-W slash T-B-O-Y. For our third and final story, who is the real winner of the US Open? Well, it wasn't a tennis player. we think it was a brand. And that winner was Cadillac. First Formula One, now the U.S. Open. Cadillac is cool again, thanks to what we call the Great Gatsby strategy. Ah, the U.S. Open of tennis. The 21-day tennis event is also a page six gossip column of TMZ hullabalooza. The most posh sport, the most exclusive event to get to, all happening in New York City. Yeah. It's not about who's playing on the court. It's about who's in the stands. I'm sorry, is that Blake Lively sitting next to Bob Iger feeding a hot dog to Jamie Dimon?

20:22Hollywood, Wall Street, Silicon Valley, they're all in the same box watching the same match. Seriously, they don't have a red carpet, but they do have a blue carpet, an actual area for photographers to take glam shots of celebrities before they enter the stadium. Now, Yetis, you could say the winner of the US Open is the tennis players. One man and one woman beat out all the other on the court. Or you could say the winner of the U.S. Open was the Honeydeus famous cocktail. The tournament sold$13 million worth of that$23 drink. But besties, Jack and I don't think the winner of the U.S. Open was Ariana Sabalenka or Carlos Alcaraz or the caviar-covered cocktail we just mentioned.

21:03The winner was Cadillac, GM's brand that suddenly is the coolest in all of luxury. Because get this, in 2022, Cadillac paid a rumored$40 million to become the official net sponsor of the U.S. Open. They replaced Mercedes, but they didn't just stick Cadillac logos on the nets of the tennis courts. They went full wedding planner on this thing. Cadillac brought 200 vehicles to drive each and every tennis player to each and every match. For the last two weeks, Cadillacs with U.S. Open branding have been shuttling players between Queens and Manhattan all day long. Also, Cadillac opened an invite-only lounge for VIP ticket holders with a concierge and a Cadillac bar.

21:45You can only get in with a special six-digit code, apparently. But Jack, what is the wildest Cadillac move of all at the U.S. Open? The whole tournament waived parking fees to anyone driving a Cadillac. That's hilarious. Now, Yetis, all of this happened the very same week that Cadillac named their two new drivers for their upcoming F1 racing season. In March, Formula One gets their first new team in a decade, and it's a Cadillac team. But Jack, we should sprinkle on some context over on Cadillac right now, shouldn't we? Let's go back again to the year that we graduated. In 2006, every rap video featured a Cadillac Escalade with 20-inch rims.

22:26Yeah, Cadillac was cool. To quote Ludacris Jack, Cadillac grills, Cadillac mills, check out the oil my Cadillac spills. But 20 years later, it's cool again. General Motors just announced last month that Cadillac has become the number one luxury brand in electric cars. The last six posts on Instagram, what do we see from Cadillac, Jack? Not corporate commercials. Behind the scenes US Open picks and F1 hype. It's coolification by association. So Jack, what's the takeaway for our buddies driving Cadillacs? Cadillac is using the Great Gatsby strategy. Ah, the Great Gatsby strategy. Yeah, it is. We have seen this marketing move before.

23:07We've seen it in the greatest American novel of all time. The Great Gatsby. F. Scott Fitzgerald. Jay Gatsby convinces New York's elite that he's rich and powerful by hosting lavish parties that everyone wants to be at. And that's exactly what Cadillac did these past two weeks at Arthur Ashe Stadium. They're not sticking a logo on the television or running commercials or hiring a celebrity spokesperson. Cadillac's not the guest of the US Open, it was the host. It wasn't marketing, this was hospitality. Cadillac isn't telling you it's cool, it's showing you by putting on a party. Just like Jay Gatsby.

23:44That's right, old sport, that's right. Jack, could you whip up the takeaways for us for our first Monday back? Tesla's new master plan cements the pivot from cars to robots and Elon gets a trillion dollars if he can make it work. From a worker perspective, that pay is not fair. But from a shareholder perspective, oh, it's fair. For our second story, J.Crew was dragged online for trying to pass off AI-generated images as real vintage photography. J.Crew knocked out J.Crew, and it shows that we've drawn a line between Photoshop and AI-generated pics. And our third and final story, Cadillac wants high-end buyers, so it hosted the entire US Open, putting on an epic party.

24:29And that's why Jack and I went back to our middle school roots and call this the Great Gatsby Strategy. But besties, this pod's not over yet. Here's what else you need to know today. First, for the second month in a row, America got a very weak jobs report. Last month, Trump was so unhappy with the jobs report, he fired our head of labor statistics. But this month, the government report showed even worse numbers. Just 22 ,000 jobs added in August, and June got revised to negative new jobs. It was the first time America has lost jobs since COVID. Now, like we said in the spring, Trump's trade war has frozen investment plans from American companies.

25:07And the weak jobs report puts the attention on the Fed. It makes an interest cut more likely this month. And second, Nike has got a new slogan, and it's, why do it? Nike says they're reintroducing their iconic, just do it, by asking the question, why do it, in their marketing campaigns. Apparently, Nike thinks turning their slogan into a stressful question, we'll connect with Gen Z angst. Jack, I've got a question as a shareholder of Nike. Nike, why'd you do it? You're not happy with this? No, no, no, no, no. And finally, Erewhon is expanding its luxury grocery from Los Angeles for the very first time.

25:46Erewhon is coming to New York City. Kind of. A private social club in New York City is getting an Erewhon smoothie bar. Fashion brand Kith is opening up a Padel Club in the West Village. And if any Yetis have guest passes to the Kith Padel Club, we badly want to go. We will test your smoothie for poison live on the podcast before you try it. We will do that. Yes, we will. Now time for the best fact yet, which, because it's Monday, means T-boy trivia. Jack, what do we got? The New York Yankees, my favorite team growing up as a kid, were actually the third Major League Baseball team in New York City, because before them came the Dodgers and the New York Baseball Giants.

26:27Yeah, the Yankees were nothing until 1919, when they paid the Red Sox$100 ,000 to acquire Babe Ruth. In today's money, that's$2 million for Babe Ruth. Okay, but besties, here is our trivia question for you. Who designed the famous New York Yankees logo? Is it A, Thomas Edison, the famous inventor? B, Albert Lasker, the famous ad man C, Louis Tiffany, the famous jeweler or D, Babe Ruth Who designed the famous New York Yankees logo? Jack and I will tell you at the top of tomorrow's pod Yetis, you look more fantastic today than you ever have Jack, you are glowing right now So great to be back on the mics with you, man Nick, are you the pod father or the padre?

27:16I always forget I'll take Padre Or is it Il Padrino, Jack? Is it Il Padrino? Nick, you are a natural father of two Very happy for you I can't wait to meet Selena when I come to SF Jack, I can't wait for you to meet Selena too And you know what, Jack? I think I got a baby to burp after this pod Yeah, you do Get out of here, man Let's get you back to your post-baby glow Besties, we'll see you tomorrow As always, we're pumped to be back

27:50And before we go, a happy birthday to Eddie Gerson Angel from San Diego, who also just got a promotion, baby. Happy birthday to Palmer Clark in Orem, Utah, who is crushing it as a new father. And Maria Evans down in Anaheim, California, is celebrating the best birthday yet. Happy 31st birthday to Jenny DiGiovanni in Chicago, Illinois. Doing logistics. and Sebastian is turning seven and Samuel is turning nine, celebrating together down in Arlington, Virginia. And to anyone else who's celebrating something today, make it a T-boy. Celebrate the wins. Oh, and a quick shout out and happy birthday to anybody who had one in the last two weeks.

28:31Unfortunately, Nick and I were off and we couldn't get to you. While we were on paternity vacation leave, we missed your birthdays, but we'll try to get you next year. Yeah, next year we'll try to move vacation to a different time. And not have a baby.

28:48This is Jack, nickel and stock of Nike. But why Nike? Why?

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