🦺 “How Vests Won Wall St” — Vest Szn. Duolingo’s unhinged mistake. Air Travel’s Expedia moment. +AI Dog Pawdcasters

0:28This is Nick. at 10 o 'clock. Gotta be there. Amazing time. Perfect. Then we went into the Central Park Boathouse for lunch. That was a scene. It's a boozy scene, yeah. Couple cocktails later and like six portions of macaroni and cheese. We just walked around Central Park while the boys fell asleep in the stroller. We hit up three different playgrounds by the end of the day. Wonderful, wonderful day in the city. Central Park's gotta have the highest concentration of playgrounds in the country. I mean, there is nothing like skinning your knee on one of those bricks and concrete structures, Jack.

1:00And we closed it all down with a cash-only Italian restaurant on the Upper West Side. If it's cash-only, you know it must be good. Oh, and the black and white cookies, Jack. Well, I'm so glad you had a fantastic time, man. It's just an amazing place for kids and everyone forgets that. Yeah, and he's get this. At the hotel, Nick had a gift waiting for me. It was three different children's books all set in New York City. The kids were in the park. They may as well see it in the books too. I'm going to read them. Eloise goes to New York tonight. Eloise and Lyle Crocodile. Jack, they know we got three fantastic stories for today's show.

1:35What do we got on the pod, man? For our first story, we just experienced the worst travel day of the year. 1 ,100 flights were canceled this weekend. Luckily, neither of mine. But besties, if you really want to understand the travel industry right now, you got to look at Expedia. For our second story, it's finally here. It's officially vest season because vests are the unofficial uniform of finance and tech. So Jack and I did the research and discovered how the vest has taken over every industry. And our third and final story is Duolingo. Duolingo had its worst day on the stock market ever, plummeting 29 % for one wild reason.

2:12Duolingo's crazy owl mascot was not unhinged enough. But before we hit that wonderful mix of stories, fantastic mix of stories, Jack, Love the mix today. There's some new competition, Nick, I think you should know about. Yeah, besties. It's not another podcast. Jack and I are facing a pod cast. Pod. P-A-W. Oh, it's a podcast. It's a podcast with dogs as the co-hosts. Get this. The fastest growing podcast show right now. It's hosted by dogs, a podcast. The co-hosts are a couple of AI dog podcasters, and apparently they're hilarious. The context to sprinkle on, the name of this podcast is The Dog Pack.

2:51Dog Pack is actually an app that lets dog owners connect with each other. But to get attention, they created a fake podcast with dog hosts. And now this real show has fake AI dogs talking about their real canine problems. The canine hosts are AI, but the human listeners have been real. And what kind of stuff are you going to hear on this podcast, Jack? The spunky Rottweilers like, pro tip, bro. If you beg for your food, they give it to you nine out of 10 times. Okay, what is that chihuahua saying on the pod though? Get a load of this guy. He recently switched me from wet dog food to dry dog food.

3:22Yeah, it's hard to compete with these guys. Now, this dog cast has boosted the app's usage to 2 million users in 20 different countries. And now they're counting their downloads in doggy years. It's so popular, Dog Talk just signed a talent agency deal with WMB to get a bunch of brand deals. If Chewy doesn't buy these guys, they must be cat people over there. But on a serious note, this actually highlights an interesting angle about artificial intelligence. Yes, it does, Jack, because when AI is replacing a human, many find it problematic. When AI pretends to be a real human, we don't like that at all.

3:55But if the AI is being clearly absurd, like it is with these puppies, we actually embrace it. Nobody's pretending to be real here. Yeah, as far as we know, there haven't been any podcasts hosted by real Rottweilers out there. This is just good, clean AI canine fun. So besties, smash that subscribe button. We mean lick that subscribe button. And remember, dogs are way more fun than cats. All the one-star reviews on this show, they're left by cats. Can you imagine if the cats were hosting a podcast, Jack? A lot of silence and a lot of judgment. True. Jack, let's hit our three stories. 15 years before this song, two boys from the Northeast met in the dorm.

4:33They had an idea to cause a cultural storm. It's the best one yet, but the best is the norm. Jack Nick, that's it. I don't even think they need to practice. 50%, 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.

4:54Start the show. First, a quick word from our sponsor.

5:05Bureau premium non-alcoholic beer. All right, yeah, he's a little behind the scenes here. Before our New York City live show back in April, Jack and I went sober for two weeks. True story. Couldn't risk getting sick. I didn't want to be groggy. I couldn't afford a hangover. It was New York, baby. Okay, but Jack, celebrating the wins is what we do. And so for our live shows, we crack open something special. So we drank Biro. The premium non-alcoholic beer brand co-founded by Tom Holland. Yeah, I actually first saw it at my grocery store. Delicious tastes like a celebration. Feels fantastic and looks legit.

5:38More on the looks in a sec. And if it's good enough for the actor who played Spider-Man, it's good enough for us. You see, it pairs well with a pickleball game, a profitable earnings report, or with the best podcast. So, Yetis, if you want to celebrate the wins with all the taste of a premium lager or IPA, but none of the alcohol, there's no better choice than Bureau. Okay, pause the pod. Did we mention the can is straight up gold? This thing will stand out at every one of your next parties. Trust us, we've done it. Only beer we know that actually upgrades the scene like a promotion. So, Bastis, if there's a win you're celebrating every day, Bureau is the non-alcoholic brew brand you got to bring.

6:13So use code T-Boy for 20 % off your first order at BureauBrewing.com. Monarch. All right, yeah, these one lobster roll, no joke, 50 bucks on Nantucket. And why is that a problem, Jack? Because we're going to Nantucket this summer on a joint family T-Boy trip. It's a write-off. It is expensive, but we will travel with peace of mind because our finances are organized in Monarch, despite the lobster rolls. Monarch is the personal finance app that tracks everything, accounts, investment, savings goals, and spending. Get your first year of Monarch Core for half off, just$50 with promo code TBOY. Monarch shows visually how much you're spending this month compared to the average month, which is really useful.

6:51So like, honestly, this month, been a doozy jack. Booked a lot of travel, but I know the future months won't be as bad after lobster roll season. You know because Monarch showed you. Last year, you had a spike in May for travel bookings, but a dip in the summer because the travel was already paid for. You can even ask Monarch's AI assistant anything about your finances. Like, what are the key changes in my spending so far this year compared to last year? And how much was spent on lobster rolls last summer? Use code TBOY at monarch.com to get your first year of Monarch Core at half off, just$50.

7:21That's 50 % off your first year at monarch.com with code T-Boy.

7:27For our first story, Expedia's booking boom is defying the economic doom. Nick, the entire travel industry is still seeing record high demands because one trip you did looks like five trips to Wall Street. Well explained. But best is, in the meantime, while you're listening to our show, Google the word travel and you're going to see headlines about the FAA cut in flights because of the government shutdown. New York to Nashville never departing. Yeah, delayed forever. But if you do look up travel instead in the Google Finance tab, you're going to see a lot of... Because Expedia stock soared by 17 % on Friday to an all-time high on news of their best quarterly earnings ever.

8:13Now, Yetis, this shocked us. And why is that, Jack? We've covered the weak jobs market in America. We've covered the young people's recession happening in America. Gen Z is basically not even buying Chipotle anymore. Yeah, because the guac and the meat is extra. But the miles are calling and I must go, apparently. And besties, we can see your wild Key West party weekend in the numbers from Expedia. Expedia's operating profit was the best on record, sending the stock to an all-time high. I'd press that cha-ching button again, Jack. But besties, here's what we find fascinating. Just the sheer scale of this, like$31 billion worth of travel?

8:53That was booked across Expedia's three travel brands in just the last three months. It's like five lifts. Expedia, Hotels.com, Vrbo, best growth in the U.S. travel demand in three years for all three of them. The CEO said on the earnings call that Americans are staying longer and booking further in advance than they usually do. So basically, you spent a couple extra days in the Dolomites and you planned that epic trip a year ago. Which is strange. More travel? It's not what you'd expect from an anxious consumer who's cutting back on Chipotle burritos. And yet these earnings are a data point of consumer confidence, at least in the entire travel industry.

9:30And Expedia is not just seeing travel growth from medallion travelers, platinum upgrading their everything. Yeah, this isn't Amex money we're talking right now, is it, Jack? No, they're seeing it across income levels. Yeah, people hate Disney World's price hikes, but you're still hanging out with Goofy and having fun while you're there. They're still going. In fact, the CEO of Expedia is so confident right now, she forecasts 6 % to 8 % revenue growth for the fourth quarter that we're already in. Let's just hope the government shutdown ends so that those bookings can actually happen. So Jack, what's the takeaway for all our buddies looking at the travel industry?

10:04You don't just travel from A to B. You travel from A to B to C to D, then back to A. Best news, Jack and I have talked to you about the money multiplier effect. Basically, an economic concept that spending multiplies as you spend. Because when you buy something, that becomes someone else's income. And then they buy something, which is someone else's income, and it goes on and on and on. And you know what? We're seeing it right now in travel. Because maybe you booked a flight to Miami on Expedia. You also booked accommodations for that trip. Maybe on Airbnb. They announced record bookings last quarter.

10:39And Jack, you probably booked a Lyft to get from the airport to that Airbnb, and Lyft also just announced record earnings last quarter. But why were you in Miami in the first place? Probably to see Lady Gaga's Mayhem Tour. Perfect timing, Jack, because Live Nation, which sold you those tickets, said the word record nine times in their latest earnings. All of these travel earnings bonanzas tell us two things. First, the post-pandemic demand for travel and IRL experiences is still very strong. And second, that the money multiplier effect is happening in travel. Because you don't just travel from A to B.

11:13You travel from A to B to C to D, back to A. Taxi! For our second story, Duolingo just had its worst stock market day ever, plummeting 23 % in just hours. The reason? Their owl isn't unhinged enough. We repeat, the owl should have been more unhinged. It proves that the most important thing at this tech company is its social media team. Now, yeah, this funny situation Jack and I have with the co-founder and CEO, Luis Van An of Duolingo, the language learning app. Well, we interviewed him in April. He came on our show, announced a new product, Chess. Yeah. And the stock rose 60 % in the three weeks after he came on T-Boy.

11:55Not too shabby. Jack and I have been telling people, come on the pod. We basically end up boosting your stock. Not too bad. But apparently that was the peak because Duolingo stock has erased all of those gains and more since. Investors, apparently they've been lost in translation. And we know the date and the place where that stock downfall began. April 28th on LinkedIn. Now, Basties, Jack and I have never seen someone get canceled on LinkedIn before, but Luis Van An, CEO of Duolingo, basically did. Yeah, well, he posted his internal memo on artificial intelligence. It said that Duolingo would not hire anybody unless the managers could prove that AI can't do the job instead.

12:34Ah, the infamous AI memo. It made their workers anxious, made other workers anxious, and made a whole lot of people mad, really on LinkedIn. Kind of looked heartless. Yeah, Jack, what's the Spanish word for uh-oh? I don't know. But for the first time, Duolingo was in the cultural doghouse, so they made a big decision. What was it? They told their social media team to stand down. They stood down. Jack, you're going to have to sprinkle on some more TikTok context for us, please. It's a big deal that Duolingo's social media team went dark because even though it's a language tech company, they're famous for their social media mascot.

13:08Yeah. The owl. The naughty green owl. Yeah, I was going to say on a hinge, but I like how you went with naughty on that one, Jack. What the owl does has nothing to do with conjugating French verbs. It's just a freaky owl that makes you feel kind of weird that you haven't opened the app yet today. That uncomfortable Duolingo owl has amassed a very real 17 million TikTok followers. No other brand's social media is even close to as big as Duolingo's. McDonald's, they're sitting at like 5 million TikTok followers. But in the face of that AI pushback from the memo that the CEO published, Duolingo put that naughty owl on pause.

13:43The CEO, Luis Van An, revealed it last week in the earnings. We passed on all the unhinged posts in our social media for a bit. Why? Because we were listening to our community, he said, aka we were in the social media doghouse. Yeah, in the old Instagram doghouse. So no surprise, the number of likes on TikTok for Duolingo fell from 90 million a month earlier in the year to just 5 million a month recently. But what was a surprise for us? That the weakness on social media translated to weakness in their core business. Because besties, Duolingo not going viral led to their daily active users growing by the smallest percentage in years.

14:21From going 50 % per quarter to just 36 % per quarter. Ay, Caramba, Jack. As they say in German, das ist ein Problem, Nick. Not possible, besties. What we're saying is that Duolingo's unhinged owl stopped being unhinged on Instagram and people stopped using the language app. Strange reason to learn German. Because a fake owl on Instagram told me to. Do you know how to say owl in German, Jack? Jack, I think it's just Owl, actually. Sounds like you don't know. So Jack, what's the takeaway for our buddies over at Duolingo? The most important team at a tech company can actually be its social media team.

14:58Yetis, two months ago, Jack and I noticed that a leader on Duolingo's social media team stepped down, so a new job posting went up. And guess what the salary was for this new job posting? $342 ,000 to manage a fake owl. Sit down, stand up, and cash that check again. That is the same salary for social media as for top engineering tech jobs. Best is this combination of that job posting and this earnings report have made a very powerful statement. And here it is. It's time to value the social media role with the value it creates and deserves. You see, for apps that depend on you opening them, like Duolingo, social media is a powerful opening tool.

15:38So Duolingo's social media manager is getting paid the same as Meta's engineers are. Yeah, it is. Your top team may actually be your TikTok team. Now, a quick word from our sponsor. Top hats, baseball hats, Von Dutch hats. We wear so many hats on this podcast. Honestly, we're not great at all of them. No, we've been avoiding hiring someone to wear those hats instead of us, especially the Von Dutch one, because hiring and training can take forever. Well, I'm proud to say that we are hiring right now at T-Boy, and this is a job for Indeed sponsored jobs. Because sponsored jobs posted directly on Indeed are 95 % more likely to report a hire than non-sponsored jobs.

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16:50Upwork. Yeah, it is. Before we had a podcast, we had a newsletter. And the moment that newsletter began growing, it's not when we came up with the clever subject lines with the emojis. It's when we found the right freelancer. Freelancer built a referral program that grew our newsletter, which helped launch this podcast, which helped to sell our company, which we eventually spun out and which eventually got us to where we are today. Yeah, that's the story. Having the right expertise at the right time, that can make or break your business. So Upwork is a one-stop platform to find, hire, and pay expert freelancers across web and software development, data and analytics, marketing, business operations, and more.

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17:54For our third and final story, besties, it's that special time of year, vest season from Wall Street to Silicon Valley. We unzipped the story on how the vest took over corporate America's wardrobe. We did. And it goes back 359 years. And yes, I put on a vest for this story. Honestly, Jack, it looks like that vest put on you. That thing's huge. You know what it's like out there. The leaves are changing. The football's playing. It is officially Vest-vember, baby. Only two more weeks before you got to add sleeves. So enjoy it. The vest, it's part of the uniform of corporate America during shoulder season.

18:33What else we got, Jack? Beige slacks, brown leather, uncomfortable shoes, a button-up white, blue, or pink shirt, and it's all wrapped together in a gray vest with an ambiguous bank logo. Yeah, since Patagonia put the kibosh on the finance-branded vest back in 2021, white-collar workers have had to adapt, and they have. I've seen some out there wearing quilted insulated vests like Barbours, and others wear huge puffy vests like me. Jack, the vest is kind of a career flex, a little bit of a status symbol, right? Like, you know, you got the Arcteryx if you made VP or the Zara if you're, you know, entry-level intern.

19:09Or the Cotopaxi if you want everyone to think that you're, I don't know, a sustainability-minded guy. But vesties add it all up and they all scream, I'm investing, literally. But you can't mock the vest's performance. It's the only fashion to defy cyclicality. That's right. Because in the 2010s, the vest expanded beyond finance bros to tech and commercial real estate. Any sector adjacent to cash flow, you're going to see guys wearing vests. And that is why in addition to cuffing season, it's officially vesting season. But Nick, the origin of the vest? Who invented the vest? You did some research on this.

19:43Oh yeah, we jumped to T-boy style. The inventor of the vest was King Charles II of England back in 1666. Here was his vision. A British fashion item to take on the French and tie together the whole outfit. I mean, Jack, if you think about it, you can picture the redcoats wearing vests during the Revolutionary War. Yeah, under their red jackets was a white vest. And for the next three centuries, that vest remained formal menswear until 1979. That's when Patagonia entered the scene. And eventually, the apparel made for mountain climbers got taken over by ladder climbers. From mountains and altitudes to mergers and acquisitions.

20:19But yet is what really fascinated us about the vest, what really stands out is not just the time length, but the acceleration of the vest. Get this, from 2015 to 2018, Moose Jaw's sales of vests rose by 700%. And Jack and I have identified three fascinating reasons why the vest experienced a surge. Number one, a practical reason, air conditioning. Yeah, in the 20th century, trading floors on Wall Street began to be jacked up with AC. I think they do this to keep their workers on edge. Like a cold worker is a hard working worker. You think you're going to like keep yourself warm by spreading those spreadsheets.

20:56That giant vest alleviates the chill. The second reason for the vest surge is hilariously, regulations. That's right, regulations. Because in finance, you are not allowed to gift a client a product worth over$100. So the vest became the perfect$95 fashion gift that didn't violate regulations. So Jack, what's the takeaway for our buddies who are everyone wearing or staring at a vest? Brands want to stand out, but people want to be in a group. So besties, a lot of business just comes down to psychonomics, psychological economics, and the vest is the one garment that effectively reflects your belonging in a group.

21:33As one trader put it, you put in the work your whole career to become VP on the equity research team someday. Well, you know what? The vest with that logo is your only silent way to communicate your accomplishment. You can't customize a suit with a brand. You can't wear a branded hat to work. That's not in the dress code. And you can't stick a corporate logo on sneakers. But the vest can become a tiny billboard of industry and achievement. Fashion's business card signaling that you belong. Creatives have their branded moleskin notebooks. Startup workers have their branded hoodies. But finance has the vest.

22:06Because in every industry, there's a craving to signal you're part of the tribe. Jack, could you whip up the takeaways for us to kick off the week? Expedia stock hit an all-time high on record U.S. travel bookings last quarter. Because one trip you do looks like five trips to Wall Street. And that is the money multiplier effect in travel. For our second story, Duolingo's daily active users slowed big time after they put their unhinged social media owl in the cage. The owl needs to be more unhinged. The most important team at a tech company can be its social media team. And finally, it's officially vest season.

22:43Not just for finance bros, for all of corporate America. The vest, it's your subtle wearable business card because people want to belong. But besties, this pod's not over yet. Here's what else you need to know today. First, Waymo won't stop, baby. Detroit, San Diego, Las Vegas, apparently they are all getting Waymo starting next year. This time, Waymo didn't announce Uber or Lyft as a partner for those three cities. And second, the Trump administration is eager to respond to last week's election, so they floated a new idea to address affordability. The 50-year mortgage. Trump's housing director said he's working on it after Trump tweeted about it.

23:22In the tweet, President Trump compared himself to FDR, who is the president who brought us the 30-year mortgage. If the 50-year mortgage becomes real, we'll cover it. But right now, it's just a tweet. And finally, Sweetgreen is selling off its robot salad making business. That's right, the Infinite Kitchen is no longer a Sweetgreen salad product. We interviewed the Sweetgreen co-founder last year and talked about this. We did. It's core to the strategy to use robots to scale salads more efficiently. Interestingly, Sweetgreen bought this Infinite Kitchen technology for 50 million bucks a few years ago, and now they're selling it to Wonder for 186 million bucks.

23:59Ironically, we interviewed the CEO of Wonder as well. It seems like every time we interview someone, something good happens, but then something not so great happens, Jack. Now, we should clarify, Sweetgreen will continue using the Infinite Kitchen, but not as the owner, just as a client. She could still get you robo-salads. Now, time for the best fact yet, which, because it's Monday, means T-Boy Trivia. Jack, what do we got? Last week, we asked you about the origin of the name Oreo, and there's no answer. It's actually a corporate mystery. Here's a question about Oreos we do have an answer for.

24:29Who is more likely to twist open an Oreo before eating it, men or women? That's right. Who is more likely to scrape off the cream filling with their front teeth like it's a snowplow? Men or women, guys or gals? The answer to this Oreo conundrum comes in tomorrow's pod. Yetis, you look fantastic to kick off the week. Jack, you look fantastic considering all the travel you've done lately. But by the way, we got to share. You got to tell the Yetis your cake story. We were at this great New York diner on the Upper West Side. What's it called, Nick? Vyond, classic. And Wilder was having a meltdown because his coloring wasn't working right.

25:06And some anonymous angel on the other side of the restaurant sent us a slice of chocolate cake to make Wilder get in a better mood. It worked perfectly. And then a couple minutes later, I go to the other side of the restaurant to thank somebody and they were gone. It was truly just a silent angel looking after our family. So whoever this cake saint was, you may be listening, you may be not, but we just want to thank you for making Jack's son, the pod son, happy. It was an incredible anonymous donation. Which leads to a new insight. If you get kids cake, they stop screaming. Besties, we'll see you tomorrow.

25:46Can't wait.

25:51And before we go, a congratulations to Eddie's Catherine and Jimmy in Brooklyn, New York, who are celebrating the best wedding yet. You guys look fantastic. Congratulations to John and Danny Gill in Grand Rapids, Michigan, who just got married. And a happy birthday to She, Dawn in Boston, celebrating just outside Boston. Happy birthday to Jamie Talbot in South Jordan, Utah. And we definitely know Jamie had cake. And Nick Alves is turning 31 years old down in Hotland, Georgia. Congratulations to Ellie Scripps in Denver, who just got a new job in sales. And Krista Gilley, happy new job down in Nashville.

26:28Congratulations. And a big shout out and kind of apology to Nick Jordan. Yeah, yeah. We said last week he was turning four, like it's his fourth birthday. It's actually four years he's been at his job. So he's very much not four years old. A lot older than four. Our bad, Nick. Congratulations. Great guy, though. Great guy. We'll celebrate your birthday.

26:50This is Jack. I own stock of Lyft, and Nick and I both own stock of Airbnb and Chipotle.

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