The Best One Yet - 🛒 “UberCartDashBnB” — Airbnb’s new bets. Boxed Wine’s boom. Robinhood’s seed farmer. +LinkedIn Snitches

Starting point is 00:00:00 This is Nick. This is Jack. Welcome back. It is Monday, August 10th. Into these pod. It's the best one yet. This is a T-Boy. The top three pop business news stories you need to know today. Another week, stocks starting off on all-time highs. I think the number of times we've said all-time highs on this pod. Yeah, Jack? Is that all-time highs? A-T-H-A-T-H. In the meantime, you're looking fantastic, and we've got three of the best stories in business. Jack, what have we got in the T-boy? For our first story, Airbnb just had their best day in history. The stock searched few. 15% Friday on five-star earnings. Because Airbnb got surprised four times by sleeper hits.

Starting point is 00:00:37 For our second story, Robin had just unveiled another venture capital fund that you can invest it. But there's one catch. It's super seedy in a good way. And our third and final story, the biggest winner in alcohol right now is boxed wine. Boxed wine, but besties, we ain't talking franzia. Luxury vineyards are now slapping the bag and it is selling. But yeties, before we hit that wonderful mix of stories. Jack, what a mix to kick it off. How was Fenway, by the way? Good time. Let's just say, as a Yankees fan, I did not sing Sweet Caroline.

Starting point is 00:01:07 Enemy territory, enemy territory. I will say, though, that the Fenway Franks are better than Yankee dogs. It's hard to beat that. It's hard. Legendary poet Ice Cube once said, Snitches get stitches. Snitches get stitches, but now snitches get a badge from LinkedIn. Snitches get promoted? Snitches get promoted? What's the news? Here's the news. LinkedIn wants you to begin ratting on your buddies who you think are writing with AI.

Starting point is 00:01:30 the first ever anti-slop button. Because get this, an estimated 41% of posts on LinkedIn are fully AI generated. It's according to Pangram, a leading AI detection software. Now, shorter posts are a little less likely to be fully AI, just 30%, not 41%. But we repeat one out of three LinkedIn posts are a straight up artificial, baby. In other words, it's not just you. Yeah, everything you've seen in your LinkedIn is AI. Was it written by Claude in accounting or Claude?

Starting point is 00:01:58 What's going on, Claude? Now, LinkedIn's AI rate is much higher than other social media platforms. We should sprinkle on the context. 20% of Twitter, fully AI. Less than 10% of Reddit, fully AI. So the only way for LinkedIn to lose this reputation and stop this madness is a straight-up snitch button. They're self-regulating with a button you're going to see on every post called Seems Like AI Slop. Enough people push it.

Starting point is 00:02:19 LinkedIn tells the user that their followers think they're sloppy. How embarrassing. So if you see a post that has three hyphens in a row. That's AI. Spill the beans on them. If you see short, punchy sentences. That's AI, rat out on that robot. Did they just write a 700-word article that ends with

Starting point is 00:02:37 It's not this, it's that? Definitely AI snitching them like that guy in Goodfellers, Jack. Yeties, if you see cringe, say cringe. Because snitches get a blue checkmark from Microsoft. Yeah, you're promoted. Congratulations. But don't worry, you won't end up like the guy in Goodfellas. You'll just get a stern notification from LinkedIn telling you, use the AI a little less buddy.

Starting point is 00:02:57 This got endorsed for snitching. Jack, let's hit our three stories. Fifteen years before this song. Two boys from the Northeast met in the dorm. They had an idea that caused a cultural storm. It's the best one yet, but the best is an norm. Jack Nick, that's it. I don't even think they need to practice.

Starting point is 00:03:14 50% that's a fat tip. Tea Boy City on your at list. If you know, you know, because we're ready to go. We can't wait no more. So just start the show. Start the show. Start the show. First, a quick word.

Starting point is 00:03:30 word from our sponsor. For our first story, Airbnb stock just jumped 15% for its best day on the stock market since its 2020 IP. Because this gig economy is big enough for the both of us. Yeah, funny things Jack and I are crafting the show each day. We actually have a policy to not discuss physical traits on the podcast. That's out of bounds. Yeah, yeah.

Starting point is 00:03:59 But where is Brian Chesky working out, Jack? Okay, because the CEO of Airbnb is busting. out of his shirt more than a McMansion. Oh, Jack, I heard Brian Chesky named his biceps Ritz and Carlton. He wears t-shirts with the thinnest cotton I've ever seen. Call a plumber, Jack, because Chesky's

Starting point is 00:04:18 got pipes. Actually, but seriously, call a plumber. We've got a leak in the Airbnb right now, guys. But the only thing more, Jack, than Airbnb's CEO, is Airbnb's stock. Because Airbnb's stock just had its best day in history, baby. Revenues rose 17% last quarter. Profit hit $816 million,

Starting point is 00:04:35 and investors loading up on shares like it was lemon pledge. A stock, it's up 46% in the last 12 months, not too shabby. You're an investor, you don't even mind that the host checkout instructions, including wood stacking. Yeah, stack the firewood before you check out. The only thing missing from Airbnb's epic quarterly earnings was they didn't sponsor or show this quarter. Yeah, first quarter they don't sponsor us is their best quarter ever.

Starting point is 00:04:57 What's going with the ad department over there, guys? Yet these investors were clearly surprised. But so was Brian. He said the word surprised four times in the earnings car. We were surprised, he said surprised so many times. Yeah, act like you've been there, Brian. Because for 19 years, Airbnb was the cheaper alternative to the hotel. But last quarter, they changed the mission.

Starting point is 00:05:15 They did. Airbnb expanded to a bunch of services linked to travel. One of them became a sleeper hit last quarter. And that sleeper hit was the rental car. Now, we told you in May that Airbnb wants to become the super app of travel. So now, as you're booking a beachside condo for the weekend, you can add a beamer to that reservation. And get this, car rentals last quarter were bigger than the home rental business for Airbnb. And by bigger, we mean longer than the home rental.

Starting point is 00:05:41 Yeah, we mean longer. Because the average length of a rental car booked on Airbnb was longer than the average stay of an Airbnb stay. Surprise, people prefer adding rental cars to an Airbnb booking instead of doing a separate booking with Hertz and Avis operator. A human being, please. But the bigger surprise wasn't that people were driving home and driving to the Airbnb in an Airbnb rental car. No, no, no, the bigger surprise was luggage storage. You've all been there. Checkouts at 10 a.m., but at Sunday, you want to go to brunch and, like, have fun in the city before going home.

Starting point is 00:06:12 And apparently, both Airbnb's team and analysts had the lowest expectations for their new luggage storage feature. Brian actually called it very unsexy. And yet that unsexy luggage storage add-on enthused demand from customers more than any other feature. Probably the one Airbnb feature everyone actually wanted was to stash away your away suitcase while you're kicking in Shanghai for 12 hours. Both of those sleeper hits, rental cars and luggage storage, increased revenue and profit per traveler last quarter. But reminder, New York City is still banning the traditional Airbnb. But can Mondani ban an Airbnb Buick? Tushay, Jack.

Starting point is 00:06:45 So, Jack, what's the takeaway for all our buddies over at Airbnb? Airbnb versus Uber versus Instacart versus DoorDash. This is Gigageddon. Oh, yeah, and we predicted earlier this year that this would happen, the Gigocalypse. All the gig apps are converging against each other, doing all. the same thing. Like last year, DoorDash launched restaurant reservations, but now so does Uber and Airbnb. They do restaurant reservations. DoorDash and Uber launched grocery delivery, which is Instacart's business. Oh, and now Airbnb is doing rental cars like Uber did. Oh, and guess what's next

Starting point is 00:07:16 from Airbnb? Grocery delivery. That's right. So you arrive at your Airbnb with a full fridge. Airbnb is zucking Instacart. Oh, wait, that's actually a partnership Airbnb is doing with Instacart. It's a gig alliance. And if they can't differentiate, then maybe someday they'll all just merge. cart dash B&B. The service fees will be 100%. I was going to say, I can't wait to see the fees jack. For our second story, Robin Hood's second publicly traded venture capital fund IPOs this week. But this time it's all Y Combinator startups.

Starting point is 00:07:50 Why see? Because planting a seed is more lucrative than owning a tree. Now, Yeti's, although the CEO looks like Zorro, Robin Hood likes to think of itself as Odysseus. Because it spent 13 years trying to eliminate Barry. is to finance so regular people can benefit. Love Zeus. Well, this year, they've targeted venture capital as their focus. Yeah, they've had two funds that let regular people get in on pre-IPO companies. Big deal, because getting pre-IPO stock in Robin Hood when we sold our previous company to Robin Hood

Starting point is 00:08:18 changed our lives, totally. I was able to buy a house that I'm in right now with the IPO proceeds of Robin Hood stock. So now, Robin Hood is letting more people get in on the ground floor, democratizing the venture fund. Robin Hood's first venture fund IPOed in March and included stakes like OpenAI, ORA, Canva, even SpaceX before the IPO. You could own those things. And now, Jack, pause the pot. Those were later stage startups, pre-IPO, but still pretty big dudes over there. But this week, Robin Hood is launching its second venture capital fund for a very different kind of private company. Ah, why combinator companies?

Starting point is 00:08:52 Yeah, he's like we said, this Robin Hood Venture Capital Fund, it's a seedy business. Seedy, but in a good way. And you'll see what we mean. because to understand why Combinator startups, you got to picture HBO show Silicon Valley. Guys working out of a garage. All sorts of energy drinks everywhere. A lot of dudes coding at computers.

Starting point is 00:09:10 Not much showering, Jack. Founders, co-founders, and early employees, that's the kind of startup we're talking about. Oh, and also a lot of those empty energy cans. And here's how it goes down. You apply to join the three-month Y Combinator accelerator program. And Jack, what do you get if you're one of the lucky few invited in? A $500,000 check,

Starting point is 00:09:27 mentorship from a bunch of legendary techies, intense training, intense coaching, and that orange sticker you get to slap on your computer as the ultimate humble brag. I'm a Y Combinator guy. If you know, you know, secret handshake. Because being a Y Combinator grad is like being a graduate of a top business school or a Jedi. Getting access to a lot of customers, Jack, and a lot of space people. Also, everyone at Y Combinator is a huge Star Wars geek. Just throwing that out there. And it helps you get funding in the future because let's take a look at those Y Combinator alumni.

Starting point is 00:10:01 Why don't we, Jack? Airbnb, DoorDash, Instacart, all those companies we just mentioned. Yeah, true. Plus Reddit, plus Coinbase, plus Dropbox, plus Open AI. You just broke our whiteboard, Jack. So this new Robin Hood Fund is invested in 80 of those Y Combinator companies all handpicked by a Robin Hood Fund Manager. That Robin Hood Fund Manager happens to be a Y Combinator graduate himself, class of 2009. Secret Handshake's Secret Handshack.

Starting point is 00:10:23 He sold his startup to J.P. Morgan eventually. But now this guy is handpicked 80 of his favorite new Y Combinator companies. And 52 of them happen to have AI in the name or the description, just in case you're wondering. And for that service, Robin Hood is getting paid 2% of whatever you invest in those efforts. Yeah, this is an important note. Robin Hood is taking the conventional fees of a venture capital fund with this public version. A 2% fee on the fund's assets every year and a 20% fee on the fund's gains every year. Add it all up and we calculated 4% of total fees.

Starting point is 00:10:54 this is one of the priciest things that Robin Hood sells. Jack, can you sprinkle in more context about how this breaks down if you actually do invest in this thing? If the portfolio gains 4% one year, you haven't gained at all because all of that just went to the fees. What you need to do is beat 4% in order to finally make a profit off the fund after the fees. But because of our takeaway, those fees very much might be worth it.

Starting point is 00:11:14 Secret handshake. So, Jack, what's the takeaway for our buddies over at Robin Hood? Planting seeds is more lucrative than owning trees. Yeah, it is, those 80 companies that this fund invest in are called seed companies, because they're as tiny as an apple seed. Contrast that to Nvidia. Invita is a mighty tree. It generates $30 to $50 billion of fruitful profit every quarter. Now, that seed stage comes before the Series A, the Series B, the C, D, E. It comes before the IPO. Seed is the second earliest stage of fundraising before the Angel round. Yeah, the Angels, those are typically family and friends

Starting point is 00:11:48 who are invested in your company. So in 2024, pitch book did a study to determine which stage of investing generates the highest returns. And it turns out seed stage companies had the highest failure rate. Yeah, I mean, there's just a few guys in a garage. 37% of the ones in this study went out of business. But even accounting for that higher failure rate, seed stage startups had the highest expected return. 25% gains per year over the 2009 to 2024 period. I mean, Jack, that is nearly double the return for the S&P 500 over the same period, which was up 14%. And how could that be? How could seed companies almost double the performance of the S&P 500? Well, let's look at Uber's Seed Round.

Starting point is 00:12:27 2010, they raised a $1.25 million check out of $5 million valuation check. How's that doing today? It's up 3 million percent since then. If you got in on Uber at the Seed round, 500 of your other investments could have failed, then you'd still be out. That's a lot of commas. Seed investing, it's dominated by VCs. Regular people, you've got to have a minimum net worth to legally take part.

Starting point is 00:12:49 Until now, because this fund let's end. anybody buy just like a stock after the IPO happens later this week. Big deal, because planting seeds is more lucrative than owning trees. Now a quick word from our sponsor. For our third and final story, wine sales keep on slipping, except for one, boxed wine. Boxed wine surged 144% last year. Oh, God. Because nothing tastes better than tension. Oh, yeah, these, you've been following this show, so you know it as true. The liquor lull is just not stopping right now. You spent the weekend playing Padell with a 30 rack of bureau non-alcs afterwards. And wine sales, they've been hit the worst. They're down 11% here on earth.

Starting point is 00:13:36 Keywords here on earth. Because up in the sky, wine sales are actually surging. Get this, airplane wine sales actually up right now. Jet blue burgundy. Qatar Air Kianti. Southwest Savagione. Oh, one sec, Jack. Hey, Delta. Where's my decanter? Now, historically, airline wine has been pretty low-brow. But now the busiest wine brands want in on the business class opportunity.

Starting point is 00:14:00 According to the Wall Street Journal, the top vineyards are competing for United Airlines is $35 million wine contract. And now we know what you're thinking, Somaliers out there. Yes, the low humidity of the cabin hurts the palate. But wine orders are going up along with the whole travel industry. Because flyers are in vacation mode, or I guess they're in splurge mode, Jack, because the company's paying for it. More anything? More everything. Yeah, the Jeff Lou Burgundy. It's a write-off.

Starting point is 00:14:22 But get this, yet. beating even airplane wine is boxed wine. Because boxed wine sales are up 144% in the last year, according to Nielsen. Jack, I'm sorry, pause the pot. As a former wine salesman of the month for the Olive Garden, how does this sit with you? I thought you were going to say, as a former college student, can you slap on some context? I guess you've got double the research going on. You may as well slap on some context for us over there.

Starting point is 00:14:46 Boxed wine, cardboard box, plastic baggie inside, spigot instead of cork. But besties, don't call your sorority sisters quite yet. This is not your college boxed wine. The boom in boxed wine is being driven by bougie boxed wine. Forget the Francia. Block sells a $95 box of wine, although they make very clear one box equals four bottles. Bratzi is direct-to-consumer wine selling 375,000 boxes right now. Oh, and the wildest part about this box wine boom?

Starting point is 00:15:11 Boxing the wine instead of bottling it is actually better for the wine. That's right. You might pause at the four-bottle-sized bag we just mentioned. I mean, who can open up a thing that's four-bottle-sized bag? bottles. You're never going to finish that. It's going to go back. But, Jack, the boxed wine lasts 30 days after opening, not seven, because it closes and seals better than a bottle. So it's actually a value play. Right. You're buying in bulk and getting a good deal. If you're okay with the lowbrow reputation of the slap into the bag. Oh, and since these boxes are easier to

Starting point is 00:15:39 pour than a bottle, then who's the biggest customer of these boxed wines, Jack? Well, who sells wine in bulk? Hotels. That's right. So Bassey's if a restaurant brings you a glass straight to your table but didn't show you the pour... That's not a glass. That was poured from a box. Add it all up and it looks like boxed wine just graduated from Sig Sig Sig App. And it's the most mature segment of the liquor industry right now. So Jack, what's the takeaway for all our buddies curious about branding? Taste, touch, and savor the tension.

Starting point is 00:16:06 The eddies two years ago, Jack and I interviewed the founder of Harry's Razors about his unicorn business. He said that great brands had tension. Two competing feelings held in the same place. You see, for our show, for T-boy, it's the tension of being about business-financy stuff. A stuffy category. But by best friends, have you. having fun filtering it all through pop culture. Who we hope you agree are not stuffy at all.

Starting point is 00:16:25 And this wine phenomenon, it has attention too. Like, look at the only two wines winning right now. Fancy wine, but in franzia boxes. And 30,000 foot ABV on an airplane. Competing forces create tension, but held together in one product. That's the brand. Sebastian, if you want to taste a top shelf brand, you want to taste the tension.

Starting point is 00:16:47 Jack, could you whip up the takeaways for us to kick off the week? Airbnb stock boomed as rental cars. and storage bookings have it looking like a super app. It also reflects the gigacalypse. No, the gigapolips. Gigacalypse. It's Airbnb and Vers, Instacard versus DoorDash versus Uber. For our second story, Robin Hood is IPOing its second venture fund, a public stock owning private seed stage companies.

Starting point is 00:17:09 Because owning a seed is more lucrative than owning a tree. And our third and final story was boxed wine. It's climbed out of the basement of your frat and into fancy wine glasses. Airplanes, too. You can taste the tension of a nice brand. But Yetis, this pod's not over yet. Here's what else you need to know today. First, let's talk about the puck, as in we just got the details of the iPhone-killing device

Starting point is 00:17:30 that OpenAI is working on, and it looks like a puck. Now, we knew it was going to be a smart speaker without a screen. Now we know it's the shape and size of a hockey puck and will cost between $300 and $400. I like the hockey puck, or is it a talking donut, Jack? What do you want to go with? Well, it's only a donut if there's a hole in the middle, which I doubt. But either way, it'll have a smart speaker, microphone,

Starting point is 00:17:49 and be designed by iPhone designer. Johnny Ive. And it will be listening to everything. And second, remember last week we told you about that finance dude, Leopold, who had the $45 billion hedge fund that fell apart? Leopold Ash and Brenner, we'll get this. He was getting married while his hedge fund was collapsing. A new news and no joke. The ceremonies were happening in Carmel, California, as his fund plummeted 80% that week. He did manage to get through the nuptials, but he had to cancel his honeymoon. I actually feel bad for him. And finally, you'll never guess the newest sponsor of NASCAR. Get this. It's Graza, the squeezable olive oil. The olive oil most known for its

Starting point is 00:18:26 squeezability. Yeah, we covered it last year. They're doing 50 million in sales for extra virgin olive oil in a shampoo bottle. You've seen it. But now, this bougie urban millennial condiment brand is sponsoring Middle America's favorite race car. And Jack, why are they doing something so surprising? Like we said, great branding has tension. Now, time for the best fact yet, which to kick off the week means some tea boy trivia. What do we got, Jack? What is the worst sports team financially speaking. More specifically, in baseball, which team has the worst ROI ever? The answer is the New York Metropolitans. Yeah, the journal ran the math in 2026 Mets are quantifiably the worst team in baseball history. Because the Mets have the fifth fewest wins of any

Starting point is 00:19:08 team in Major League Baseball. And yet the Mets are neck and neck with the Dodgers for the highest payroll in the league. Highest payroll, fewest wins, worst R-O-I. Oh, and ironically, the Mets are owned by a billionaire hedge funder Steve Cohen. who now has the title for worst ROI in sports history. The Mets, they're spending $5.2 million on every single win. Well, whatever wins they have. You know, Mets stands for Must End the Season. Yeties, you look fantastic over there.

Starting point is 00:19:37 Jack, why don't you slap the bag one more time for us? Yates, if you like today's show, drop a link to today's episode in your group chat. That's how we grow the pot. And if you haven't yet, grab tickets to our live show. They're on sale now at t-boypod.com and in the episode description. and I, we'll see you tomorrow. If you know, you know. And before we go, a happy birthday to Legendary Eddie Grace Hunter, moving from Florida up to

Starting point is 00:20:03 New York City. Happy birthday to Christina Greggs in Florence, Kentucky, who's catching all the Pokemon for her birthday. And Jonah Faye Herbitt's, the branding Baron of Brooklyn. Congratulations and happy birthday, man. Happy birthday to Ayla Wong in Colorado. And Brandon Little's, happy Buffalo Bill's birthday. Congratulations to Talia Dumilan, who is starting her PhD in Oslo, Norway, and just got Asana. And Josh, Mitchell Plotz of a 24-year anniversary in Beaver, Pennsylvania. Congratulations, guys. And a shout-out to Pedro Almoda for the heads-up on the iPhone fact about sales in Brazil. And Meredith Johnson, thank you for your best fact yet on Minnesota State Fair. We're sorry we're going to be on vacation

Starting point is 00:20:40 when it actually happens, but we love what you put out there. And to anyone else, celebrating something today, make it a team one. Celebrate the wins. This is Jack. Nick owned stock of Airbnb. We both own stock in Robin Hood, and we both own ETFs of the S&P 500.

The Best One Yet - 🛒 “UberCartDashBnB” — Airbnb’s new bets. Boxed Wine’s boom. Robinhood’s seed farmer. +LinkedIn Snitches

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