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

0:28This is Nick. Stocks surged 15 % Friday on five-star earnings. Because Airbnb got surprised four times by sleeper hits. For our second story, Robin had just unveiled another venture capital fund that you can invest in. 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 yetis, 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.

1:07Enemy territory, enemy territory. I will say, though, that the Fenway Franks are better than Yankee dogs. It's hard to beat that. 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. With the first ever anti-slop button. Because get this, an estimated 41 % of posts on LinkedIn are fully AI generated. That's according to Pangram, a leading AI detection software.

1:43Now, 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 straight up artificial, baby. In other words, it's not just you. Yeah, everything you see in your LinkedIn is AI. Was it written by Claude in accounting or Claude? What's going on, Claude? Now, LinkedIn's AI rate is much higher than other social media platforms. Oh, it 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.

2:13They're self-regulating with a button you're gonna see on every post called, seems like AI slop. Enough people push it. 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 him. 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, it's not this, it's that. Definitely AI snitching them like that guy in Goodfellas Jack. Yetis, if you see cringe, say cringe. Because snitches get a blue checkmark from Microsoft. Yeah, you're promoted.

2:49Congratulations. 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. He's got endorsed for snitching. Jack, let's hit our three stories. 15 years before this song, two boys from the Northeast met in the dorm. They 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, because we ready to go. We can't wait no more, so just start the show.

3:26Start the show. First, a quick word from our sponsor.

3:36Indeed. We missed the deadline. My recording device is having issues. Our contractor pretended to be sick. I know he's watching the World Cup matches, Jack. Or how about this? Elon just tweeted something at 3 a.m. that completely changes the takeaway on our second story. We gotta re-record the show. So besties, when workplace chaos hits you, you need the right hire. And this is a job for sponsored jobs. Indeed Sponsored Jobs gets you quality candidates when you need them most. We produce a daily episode of this show, 250 episodes a year. Sometimes we need help, we need it fast. So spend less time searching and more time actually interviewing candidates who check all your boxes.

4:09Less stress, less time, more results. When you need the right person to cut through the chaos, this is a job for Indeed Sponsored Jobs. And listeners of this T-Boy show will get a$75 sponsored job credit to help get your job the premium status it deserves at Indeed.com slash podcast. Just go to Indeed.com slash podcast right now and support our show by saying you heard about Indeed on this show. Indeed.com slash podcast and mention T-Boy. Terms and conditions apply. Need a hiring hero? This is a job for Indeed sponsored jobs. Monarch. Yetis, you know my first money lesson? It was where to put our lemonade stand.

4:44I 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. Because every minute, it's tracking your savings, spending, investments, and more.

5:10For 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. Because we pioneered it for him, Jack. Resties, write your own story with Monarch.

5:37Use code TBOY 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.

5:49For our first story, Airbnb stock just jumped 15 % for its best day on the stock market since its 2020 IPO. Because this gig economy is big enough for the both of us. Funny thing is 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. But where is Brian Chesky working out, Jack? Okay, because the CEO of Airbnb is busting out of his shirt more than a McMansion. Aw, 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 got pipes.

6:30Actually, but seriously, call a plumber. We 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. 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 our show this quarter.

7:05Yeah, first quarter they don't sponsor us is their best quarter ever. What's going with the ad department over there, guys? Yeah, these investors were clearly surprised. But so was Brian. He said the word surprised four times in the earnings call. 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. 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.

7:34Now, 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. 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.

8:08But 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. We've all been there. Checkouts at 10 a.m., but it's Sunday. You want to go to brunch and like have fun in the city before going home. 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 it in Shanghai for 12 hours.

8:42Both 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-ic? Touche, Jack. So Jack, what's the takeaway for all our buddies over at Airbnb? Airbnb versus Uber versus Instacart versus DoorDash. This is gigageddon. Oh, Yetis, 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.

9:18They 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 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. UberCart-BNB. The service fees will be 100%. I was going to say, I can't wait to see the fees, Jack. For our second story, Robinhood's second publicly traded venture capital fund IPOs this week.

9:58But this time, it's all Y Combinator startups. Why seed? Because planting a seed is more lucrative than owning a tree. Now, Yetis, although the CEO looks like Zorro, Robinhood likes to think of itself as Odysseus. Because it spent 13 years trying to eliminate barriers to finance so regular people can benefit. Law of 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 Robinhood when we sold our previous company to Robinhood changed our lives, totally. I was able to buy a house that I'm in right now with the IPO proceeds of Robinhood stock.

10:36So now Robinhood is letting more people get in on the ground floor, democratizing the venture fund. Robinhood's first venture fund IPO-ed in March and included stakes like OpenAI, Aura, Canva, even SpaceX before the IPO. You could own those things. Now, Jack, pause the pause. Those were later stage startups, pre-IPO, but still pretty big dudes over there. But this week, Robinhood is launching its second venture capital fund for a very different kind of private company. Ah, Y Combinator companies. Yeah, he's like we said, this Robinhood venture capital fund, it's a seedy business. Seedy. But in a good way.

11:08And you'll see what we mean. Because to understand Y 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. 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, mentorship from a bunch of legendary techies, intense training, intense coaching, and that orange sticker you get to slap on your computer is the ultimate humble brag.

11:47I'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. Why don't we, Jack? Airbnb, DoorDash, Instacart, all those companies we just mentioned. Yeah, true. Plus Reddit, plus Coinbase, plus Dropbox, plus OpenAI. You just broke our whiteboard, Jack.

12:21So this new Robinhood fund has invested in 80 of those Y Combinator companies all handpicked by a Robinhood fund manager. That Robinhood fund manager happens to be a Y Combinator graduate himself, class of 2009. Secret handshake, secret handshake. He sold his startup to JP Morgan eventually. But now this guy has 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, Robinhood is getting paid 2 % of whatever you invest in those efforts. Yeah, this is an important note. Robinhood is taking the conventional fees of a venture capital fund with this public version.

12:56A 2 % fee on the fund's assets every year and a 20 % fee on the funds gains every year. Add it all up and we calculated 4 % of total fees. This is one of the priciest things that Robinhood 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. Secret handshake. So Jack, what's the takeaway for our buddies over at Robinhood.

13:29Planting seeds is more lucrative than owning trees. Yeah, it is. Those 80 companies that this fund invests in are called seed companies because they're as tiny as an apple seed. Contrast that to NVIDIA. NVIDIA 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 who are invested in your company. So in 2024, PitchBook did a study to determine which stage of investing generates the highest returns.

14:06And it turns out seed stage companies had the highest failure rate. Yeah, I mean, there's just a few guys in the 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. 2010, they raised a$1.25 million check at a$5 million valuation.

14:42Jack, 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 and you'd still be up. That's a lot of commas. Seed investing, it's dominated by VCs, regular people. You got to have a minimum net worth to legally take part. Until now, because this fund lets 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. This episode is brought to you by Bill, the intelligent finance platform that helps businesses scale with proven results.

15:20Yet he's paying and getting paid. That is a pain for small and medium-sized businesses. Jack, did you send the invoice? Did they see the invoice? Did you remember to remind them to see to pay to remember to pay the invoice? If you drop the ball in any one of those steps, you don't get paid. Nope. And you're missing out on cash flow. You should not have to chase your customers. This isn't tags. So powered by AI, Bill does all that simply and automated that you don't have to. ACH, credit card, check, international wire transfers. They probably do carrier pigeon bill pay if that's how you want to get paid.

15:50Bill is the intelligent finance platform trusted by nearly half a million businesses and 98 of the top 100 US accounting firms to manage, move, and maximize your money. They have securely processed over a trillion dollars in real transactions. That is proven infrastructure you can actually trust. So besties, talk to an expert at bill.com slash proven and get$150 gift card as a thank you. That's bill.com slash proven. Terms and conditions apply. See offer page for details. Built. Yeah, it is. Full disclosure. I used to own an apartment, but then my wife and I sold it, and now we're back to renting, baby.

16:22I'm owning, but we both suffer the same issue, Nick and me. Yeah, we do. We're not getting points on rent or mortgage payments right now. Yeah, that's why we were shocked and are now both seriously considering what we just heard from Built. This is wild. Because paying for the roof over your head, it's our single biggest expense. Whether you rent or you own, that's the case. Well, Built will pay your mortgage or your rent for you, so you get the points. Points can be redeemed toward your next flight, hotel, Lyft ride, Amazon.com purchase, and more. Personally, I'd use them in the Built travel portal, or simply use them toward a future rent payment.

16:53And one unexpected benefit of Built is that every member gets access to its agentic neighborhood concierge in the Built app. First, you download the Built app. Second, you link your credit or debit card. And then you ask the Built neighborhood concierge to basically be your AI butler. Makes you feel fancy. So download the Built app and join the membership for where you live at joinbuilt.com slash tboy. That's J-O-I-N-B-I-L-T dot com slash T-B-O-Y. Use our link joinbuilt.com slash tboy so they know Nick and Jack sent you.

17:23For 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, 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 Padel 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. Keywords here on Earth. Because up in the sky, wine sales are actually surging. Get this, airplane wine sales actually up right now. JetBlue Burgundy. Qatar Air Chianti?

18:07Southwest Sauvignon. Oh, one sec, Jack. Hey, Delta, where's my decanter? Now, historically, airline wine has been pretty lowbrow. But now, the bougiest wine brands want in on the business class opportunity. According to the Wall Street Journal, the top vineyards are competing for United Airlines' $35 million wine contract. And now we know what you're thinking, sommeliers 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.

18:37More anything, more everything. Yeah, the JetBlue Burgundy, it's a write-off. But get this, Yetis. 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 pod. 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. Boxed wine. Cardboard box, plastic baggy inside, spigot instead of cork.

19:08But besties, don't call your sorority sisters quite yet. This is not your college boxed wine. The booming boxed wine is being driven by bougie boxed wine. Forget the Franzia. Block sells a$95 box of wine, although they make very clear one box equals four bottles. Grazzi is direct-to-consumer wine, selling 375 ,000 boxes right now. Oh, and the wildest part about this box wine boom? Boxing the wine instead of bottling it is actually better for the wine. That's right. You might pause at the four bottle size bag we just mentioned. I mean, who can open up a thing that's four bottles? You're never going to finish that.

19:41It's going to go bad. 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 slapping of the bag. Oh, and since these boxes are easier to 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, Basties, 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.

20:12Add it all up and it looks like boxed wine just graduated from Sig Sig F. 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. Yet, 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 financing stuff. A stuffy category. But by best friends having fun filtering it all through pop culture.

20:41Who we hope you agree are not stuffy at all. And this wine phenomenon, it has a tension 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. So, Basties, if you want to taste a top-shelf brand, you want to taste the tension. Jack, could you all 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 gigocalypse. No, the gigapalips. Gigacalypse.

21:18It's Airbnb versus Instacart versus DoorDash versus Uber. For our second story, Robin Hood is IPO-ing its second venture fund, a public stock owning private seed stage companies. 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 that OpenAI is working on, and it looks like a puck.

21:52Now, 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, 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 Aschenbrenner.

22:21Well, get this. He was getting married while his hedge fund was collapsing. 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 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.

22:57And 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 T-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 and the 2026 Mets are quantifiably the worst team in baseball history. Because the Mets have the fifth fewest wins of any team in Major League Baseball. And yet the Mets are neck and neck with the Dodgers for the highest payroll in the league.

23:32Highest payroll, fewest wins, worst ROI. 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 bucks on every single win. Well, whatever wins they have. You know, Mets stands for must end the season. Yetis, you look fantastic over there. Jack, why don't you slap the bag one more time for us? Yetis, 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 tboypod.com and in the episode description.

24:09Nick and I, we'll see you tomorrow. If you know, you know.

24:16And before we go, a happy birthday to legendary Eddie Grace Hunter, moving from Florida up to New York City. Happy birthday to Christina Griggs in Florence, Kentucky, who's catching all the Pokemon for her birthday. And Jonah Faye Hurwitz, the branding baron of Brooklyn. Congratulations and happy birthday, man. Happy birthday to Ayla Wong in Colorado. And Brandon Little's happy Buffalo Bills birthday. day. Congratulations to Talia Dumoulin, who is starting her PhD in Oslo, Norway, and just got a sauna. And Josh and Rachel Platts have a 24-year anniversary in Beaver, Pennsylvania. Congratulations, guys.

24:48And a shout out to Pedro Almada 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 when it actually happens, but we loved what you put out there. And to anyone else celebrating something today, make it a T-boy. Celebrate the wins.

25:08This is Jack, Nick on stock of Airbnb. We both own stock at Robinhood, and we both own ETFs of the S &P 500. Your team just added its 67th AI tool and also your 67th security blind spot. The good news? The Vanta agent works like a GRC engineer in the background, finding every app your team uses, scoring the risk, and drafting fixes for you. Vanta is the platform used by over 16 ,000 fast-moving companies like Ramp, Cursor, and Harvey, who are shaping the future with AI and staying ahead of AI risk. Get started at Vanta.com.