

20 Oct 2025 ¡ 21m ¡ 7 chapters

The episode covers: (1) Appleâs exclusive 5-year Formula One TV rights deal in the U.S. starting 2026 (about $700M total; $140M/year vs ESPNâs $85M/year), framed as brand-premium âSonny Hayes/Ted Lasso strategyâ rather than profit. Key claim: Apple TV is âa handbagâ to make Apple look fancy, targeting luxury audiences. (2) âDate maxxingâ: U.S. date demand is surgingâGoogle searches up 20 years; sales up 30% YoY after +19% prior; medjool dates are 40% of sales. Key claim: climate change boosts date supply (heat-loving palms; U.S. industry traces to 11 imported Middle East trees).
RX/Lara bars using dates; date subscription brands (Meladuco, etc.). (3) Ramp: $23B-valued expense/credit-card startup hires Brian Baumgartner (Kevin from The Office) as CFO for a public expense-report âgagâ and uses its blog/data as marketing. Key claim: Rampâs blog âreplacesâ BLS.
alcohol-consumption and Saturday DoorDash expensing reports.
none mentioned (no interview guests).
Written by AI. May contain mistakes.
Discussion on tipping trends in various cities across America.
âFor our second story, it's the hottest selling fruit in America right now.â
Analysis of Apple's purchase of F1 TV rights and its implications.
âHappy wedding season to all those who celebrate.â
Investigation into the rising popularity of Medjool dates in the market.
âNot to turn a profit, but to shower Apple's brand in F1 champagne.â
Explore how dates are marketed as lifestyle products rather than just food.
âEach of these are farms with their own CPG-style packaging and logo.â
Analyze Ramp's innovative marketing strategies and cultural relevance.
âFor our third and final story, Ramp, an enterprise software company, just hired Kevin from the office as their CFO.â
Discover Netflix's K-pop Demon Hunters and its theatrical release with AMC.
âApple TV is the new exclusive home of Formula One in the United States for the next five years.â
Find out why San Francisco is considered the worst tipping city in the US.
âhe would do it all from a helicopter with an ATM card.â

Get the gist, explore an idea or ask about something said.
On The Best One Yet, what are the key points of this episode?
Automatic transcript. May contain errors.
0:28This is Nick. because this is a fashion statement. For our second story, it's the hottest selling fruit in America right now. Dates. America is date maxing right now, and they're getting an assist, shockingly, from climate change. And our third and final story is Ramp. It's a$23 billion startup selling business credit cards and expense management. But Ramp just hired a cast member from the office as CFO, and their blog is a must read. It's not Dwight Schrute. No, no, no. But we'll explain more if you know, you know. But yetis, before we hit that wonderful mix of stories. Oh, what a mix of stories to start the week.
1:07Love the pre-Halloween week, Jack. We hope you had a fun night or two this past weekend. Full disclosure, Jack, we went out to Sorrel, sat at the bar, lovely. Love that place. I went to Vermont's finest vineyard. Yes, we can grow grapes here in Vermont. Bit of an oxymoron, but story for another pod. In the meantime, the biggest question we must all be asking is, how much did you tip? The bigger question, which city has the best tippers? Okay, Jack, even bigger question, which city has the worst tippers? Because Yeti's tipping has become one of the most controversial topics in this economy. Yeah, because in this economy, tipflation, oh, you are tip feeling it right now.
1:46There was tip creep early in 2020, 2021. Then we had tip fatigue in 2022, 2023. Trump's big campaign proposal last year, no taxes on the tips. But back to the question, which city has the top tippers? And Jack, the answer, please. Denver, Colorado. Yeah, it's Denver. The average tip is a mile high 21.2 % over in Denver. The second top tippers is Austin, Texas at 21.1 % tips. Then you got Seattle, Miami, Houston rounding out the top five with an average tip over a nice 20%. But now the awkward part. I knew we were going there, Jack. We're going to shame the bottom half of the tipping totem pole.
2:24Jack, New York, the average tip? 19.9%. Chicago, what are we talking about? 19.8%. Lovely Los Angeles? 19 % even. We're starting to pick up on a little inverse correlation here, aren't we, my friend? The higher the rent in the city, the lower the people tip there. In fact, can you guess the worst tipping city in America right now, besties? It's the only one with 18 at the beginning. Well, because it is T-Boy Trivia Monday, Jack and I are going to let you guess before we tell you that final answer. And there's actually a reason it'll make sense when we tell you. Yeah, we'll reveal it at the end of today's podcast.
3:00If you guess it right, we may send you a tip. Drop your Venmo handle in the comments. Yeah, we got you on this one. Jack, three stories. Let's hit him, baby.
3:19The 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.
3:37Start the show. First, a quick word from our sponsor.
3:47Gusto. One sec, Yetis. We just need to take a break from the pod for a moment to find that I-9C3 IRS tax form for each employee. And then, Jack, we got to make sure each coworker is countersigned, I think. Oh, yeah, yeah. And then we have to track down each employee and make sure they know their health insurance options. Oh, right. Did everyone know open enrollment ends tomorrow? Nope. No one did. Yetis, we are just podcast hosts. We also run a media company here. And full-time employees mean full-time benefits, too. Which means roughly 46 ,000 forms, documents, and tasks to process for each team member.
4:19Oh boy, if you're a small business, you'll want outsource all that to Gusto. Gusto is online payroll and benefits software built for small businesses. It's all-in-one, remote-friendly, and incredibly easy to use. So you can pay, hire, onboard, and support your team from anywhere. Gusto handles payroll automatically. It handles taxes associated with payroll, health benefits, commuter benefits, 401ks. You get unlimited payroll for one monthly price and direct access to certified HR experts. That's how they got G2's highest satisfaction products list this year and trusted by over 400 ,000 small businesses.
4:51Try Gusto today at gusto.com slash tboy and get three months free when you run your first payroll. That's three months free payroll at gusto.com slash tboy. One more time, gusto.com slash tboy. Monarch. Happy wedding season to all those who celebrate. Wedding season, that means you just liquidated your 401k to pay for that bridesmaid dress. Flights, hotel, and a gift. Your presents. It was not the only present. Good timing though, because Monarch is the personal finance app that tracks everything. Your accounts, your investments, your savings goals, and your spending. We use Monarch to keep all our personal finances accounted for and in one place.
5:28We're excited that listeners of this show can get your first year of Monarch Core for half off. That's just 50 bucks with promo code TBOI. The weekly spending recap uses AI to categorize everything you spent organizing them into digestible buckets. Weekly emails are perfect, by the way, because checking finances daily, that's too much. Monthly, that's probably not enough. So Monarch helps you make sure you're on track for seven different destination weddings this summer. Because you don't want to go into debt if you don't even know the groom. Who's Henry? Besties, use code TBOI at monarch.com to get your first year of Monarch Core half off at just 50 bucks.
6:04For our first story, Apple bought the exclusive TV rights to Formula One. Five years, 700 million bucks. Why? Not to turn a profit, but to shower Apple's brand in F1 champagne. Now, Yetis, let's start with some context. The best thing that could happen to Apple is if this AI thing turns out to be a huge bubble. Yeah, they'd be like, see, that's why we didn't invest in AI. Apple, they're not dropping cash in AI startups or AI stars like Zuckus. They're dropping cash right now on Ferraris. Starting in 2026, Formula One car racing is going to move from ESPN to Apple TV. Hey Siri, start your engines.
6:45And Apple announced this the day before the Austin Grand Prix down in Texas. 140 million bucks a year for this deal. That is way more than the 85 million bucks a year that ESPN was paying for the cars. Now, back in 2018, Americans didn't even know F1. Like, we didn't know a Schumacher from a shoe. A chassis? Excuse me? Nick, in 2018, ESPN was allowed to broadcast F1 for free. F1 was that desperate for America's attention. Sit down, stand up, and buckle up again. But now, just seven years later, F1 has a$700 million deal with America's most prestigious tech company. Because while OpenAI, Microsoft, and Google are obsessed with that whole AI thing, Tim Cook would rather be partying in a Bugatti over in Monaco.
7:32And Nick, this is the second time a big sports league has gone exclusive to streaming in America. You know the first time that happened? Soccer with Major League Soccer. And who was that deal with, Jack? Also with Apple. That's right, besties. When that deal happened, Jack and I called it the Ted Lasso strategy. This time, we're calling it the Sonny Hayes strategy. And here's why. Because when Apple TV acquired the rights to Major League Soccer in 2022, they were riding on two Ted Lasso Emmy Awards. Here was the playbook. Apple made a fictional show about soccer to create demand for a real soccer TV deal.
8:12And you know what? Three years later, we're kind of seeing the same thing right now with racing. Apple made a fictional race car driver in Brad Pitt. Get us ready for real race car driving with an F1 TV deal. Because Apple knows that for streaming to be a viable business model, nothing drives eyeballs like live sports. It's the holy grail of TV. Yes, it is. But Apple's not looking for mainstream sports appeal, so they didn't make bids on the NFL or the NBA. One second, Jack. Hold my Louis Vuitton because Apple... Apple's looking for luxury appeal. That's why Tim Cook just bought F1 like it was a Prada bag.
8:49So Jack, what's the takeaway for our buddies over at Apple? Apple TV is just a handbag. It's there to make the rest of Apple look fancy. Yetis, let's talk numbers here. Apple makes$100 billion in annual profit. Streaming profits? That would be just a drop in the bucket comparison. Even if they were as successful as Netflix, those streaming profits would not move the needle at Apple. No, no, no, no, no. That's why the strategy of Apple TV isn't to make a profit. It's there to elevate the Apple brand. Look at their TV shows. They're all prestige television. Totally. The Morning Show, Ted Lasso, Severance.
9:25The goal is to compete with HBO for the most Emmy Awards. Jack, how about the movies? Also highbrow. They're looking for Oscars over at Apple, not box office numbers. And it's the same with Apple TV's sports division. American soccer fans, they're more likely to be Kendall Roy than Larry the Cable Guy. I think Kendall Roy did buy a soccer team at one point in succession, right? Yeah. In Formula One, they don't do tailgates and chicken wings. They do VIP sections and champagne. Because Alala Besties and Apple's media strategy is to make the rest of the company feel premium. Like a luxury accessory hanging over your shoulder.
9:59For our second story, the hottest produce in America right now, it's dates. The date fruit is selling at all-time high prices and all-time high volumes across the country. And the medjool date is a fascinating rule breaker when it comes to commodities. And we actually tracked down the family tree that started it all. But besties, if we're going to tell this story, I mean, Jack, every time Alex has been pregnant, what gift have Molly and I sent you guys? What gift have Molly and I sent you guys? A box of due dates. Yeah, we send you guys due dates. Why is that? You have this woo-woo theory that dates induce childbirth, which is hilarious.
10:42It's a scientific thing. Yeah, it is. We're not talking dinner dates here. We're not talking romantic dates and we're not talking calendar dates. We're talking edible dates. Dates, the wrinkly brown, plump, sugary fiber fruits. Yeah, they kind of look like a giant raisin, but they taste like a caramel, baby. Split it in half, put some peanut butter in there. It's called Nature's Snickers Bar. And here's the surprise. Google searches for dates just hit a 20-year high. What about sales? Those are up 30 % in the last year in America after jumping 19 % the year before. Now, besties, Jack and I call this trend or fad date maxing, and it is powered by one particular type of date.
11:20The medjool date. The medjool. Those are the moist ones. Those are the ones you want to grab. 40 % of all date sales right now are specifically medjool dates. The medjool is the biggest date and the tastiest date. It's the filet mignon for this fruit. It's the Cadillac dates. There is some sugary junk in that trunk, Jack. Okay. It is shocking that all that sweetness is natural. I haven't spoken to my dentist, but so far so good. But besties, here's what Jack and I find fascinating about this story. There is one surprise reason Americans have become date demanding divas these days. Dates are the rare fruit benefiting from climate change.
11:58True story. We'll get into it in a sec. But first, dates are also piggybacking on the protein trend right now. That's right. The number three ingredient in a date after carbs and fiber is protein. Yeah, Yeah, high fiber and protein. That's why dates are the key ingredient in RX bars and Lara bars that you're seeing on grocery stores. That's why I like everything surging in the world. TikTok is part of the reason. There's recipes for at-home protein bars that you need dates to create. Okay, so as the context we sprinkled on, this protein moment is driving date demand. But at the same time, climate change is driving date supply.
12:35As one newspaper we found put it, heat waves are called a blessing for these desert-loving date palms in America. Side note, dates grow on palm trees. And when they grow on the tree, they look like gigantic grapes. And apparently these giant grape-like looking dates have a thirst for heat. I couldn't believe when Nick told me this next statistic. The date palm trees of the southwest of the United States, they all descend from 11 original imported trees. from the Middle East. Isn't that wild? 11 trees brought in from Morocco 100 years ago are the source for pretty much all our dates in America.
13:12Those are the ancestor trees of the U.S. date growing industry. So as climate change makes Phoenix feel more like Kuwait, dates are digging in with record yields. But what really fascinates us as business guys is that fruits are a commodity. There's no difference when you take one fruit or another fruit. They're all the same. Like oil and gold, fruit is typically treated as a commodity. The logo doesn't matter. The quality is always the same. And yet with dates, it's different. Why? The date industry is filled with brands. We didn't know why. So we whipped up this takeaway. Jack, what's the takeaway for our buddies digging on dates?
13:48The date industry has turned a commodity into a lifestyle. Yetis, you may have noticed at your local grocery store that there are a bunch of different date brands on the shelf. There's a brand called Date Better. There's Gato Dates, Julie's Dates, and Meladuco dates. Each of these are farms with their own CPG-style packaging and logo. Okay, but that's just not the case with any other produce. It only seems to be the case with the date. The last company I mentioned, Meladuco, they sell a date subscription. So why are dates the only fruit or vegetable dominated by brands? Because they all treat the date like a lifestyle product.
14:24Not a food, an indulgence. They're positioned less as a fruit, more like chocolate, because it's all the same thing, chocolate, cocoa, sugar, maybe a little bit of milk. But chocolate is dominated by brands, and dates are trying to do the same thing. By shifting the purpose from utility to treat, the date industry can support multiple brands. And like I'm willing to pay more for Ritter chocolate, I'm willing to pay more for Meloducco dates because it's a lifestyle statement. Now, a quick word from our sponsor. Walmart business. Yetis, we cover business trends on our show, and they move faster than you can spelled GPU.
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16:35So it's easier to spot trends and improve the experience over time. Decagon helps power millions of conversations every day for brands you know and love, including Avis, Affirm, Fanatics, and Aura. Ready to transform your customer support? Go to decagon.ai slash tboy to get a personalized demo and see what Decagon can do for your team. Check Decagon out at decagon.ai slash tboy. That's decagon.ai slash tboy. For our third and final story, Ramp, an enterprise software company, just hired Kevin from the office as their CFO. Ramp is everywhere, though, because their expense reports are now viral economic data.
17:17Ah, Ramp. Yetis, you may have seen their commercials on TV. Love finance. That's their slogan. Based in New York City's Flatiron District, the business model is boring. They help companies manage their expenses. Which is kind of like what Kevin did. You know, the fictional, chilly-loving character from that famous comedy, The Office. Kevin, Oscar, and Angela. They were like the finance department, right? Frank from finance loved it. Well, last weekend, his ramp hired that actor, Brian Baumgartner, to be their CFO as a funny little gag. Here was the stunt. They hired the character from The Office known as Kevin and put him in the Flatiron Building, a big, like, high-traffic pedestrian area of New York City, for a public display to watch him struggle to process expense reports.
18:05A live scoreboard showing how many expense reports Ramp was processing. Which was millions. Versus Kevin from The Office. Who could only produce 84 in his full workday. 84 to be exact. And the marketing message here, what was it, Jack? Loud and clear. Ramp software will manage your company's expense reports way better than your finance department can. So besties, that was last week. Ramp, they've hit a billion dollars in annual revenue. They're now a$23 billion valued company on that value proposition. That's three lifts of valuation right there. But here's what we really find fascinating about Ramp.
18:40Despite their boring back office business model, Ramp's brand is known way beyond finance departments. Exactly. Ramp competes with Brex, Expensify, Bill.com, but only Ramp has a cultural relevance as big as Cardi B. Now, part of it is their success in traditional marketing. Ramp spends more marketing budget than other B2B software rivals do. If you Google their competitor Brex, it's Ramp who shows up as the number one in Google searches because they paid Google. But the real savvy marketing is in Ramp's blog. They creatively publish the data that go through their systems in ways that are really interesting.
19:18Because Ramp has turned your company's expense spending into viral content for everybody to see. More viral, Nick, than Kevin's famous chili. Even Dwight Schrute would agree with that one. So Jack, what's the takeaway for our buddies over at Ramp? Ramp's blog has replaced the Bureau of Labor Statistics. Now, yeties, Jack and I were aware of Ramp way before they hired Kevin from the office as their CFO for this week-long gag. Yet he's early adopters of San Francisco and New York tech startups. They tend to be other San Francisco and New York tech startups. So Ramp has data right now on how tech startup workers are spending their money.
19:58And they publish that data in really interesting blog posts. For example, Ramp used your expense reports to publish a blog post about alcohol consumption. It turns out, according to Ramp data, that Washington, D.C., Boston, and San Francisco workers are drinking less alcohol than the last two years. But New York, Dallas, and Houston workers are drinking more alcohol. That's interesting. Oh, let's say you're curious about the list of most expensed restaurants in San Francisco. Ramp knows, so they published that data. And Nick's favorite restaurant, Spruce, is number five in San Francisco. Another example, Ramp also went viral for a report titled, San Francisco Tech Now Works on Saturdays.
20:38Because Ramp had data that San Francisco tech workers were expensing DoorDash orders on Saturday because Sam Altman made them come into the office. Vesties, Ramp, they have an economic lab with literal economists, but they turned it into a marketing weapon. And with the U.S. government shut down right now, Ramp's fascinating finance blog has replaced the Bureau of Labor Statistics. Jack, could you whip up the takeaways for us to kick off the week? Apple TV is the new exclusive home of Formula One in the United States for the next five years. Apple TV, it's just a handbag. It's there to make the rest of Apple look fancy.
21:19For our second story, dates are more popular in America than ever. They're the Palantir stock of produce. Why are there date brands? Well, it's because we treat dates like candy, not a commodity. And our third and final story is Ramp. It's a$23 billion B2B software company whose brand punches way above its weight. Because Ramp strategically turned our spending data into viral blog posts. But yetis, this pod's not over yet. Here's what else you need to know today. First, Netflix's K-pop Demon Hunters is so popular, it's going to retroactively go to the big screen. Here's the story. AMC, which is struggling now that it's not a meme stock anymore, is partnering with Netflix.
22:02It starts Halloween weekend. K-pop Demon Hunters will be in 400 AMC theaters. And if Spirit Halloween didn't do a deal for K-pop Demon Hunter costumes, huge mistake. Huge mistake. And second, the reason that stocks took a pause last week? Well, the answer is cockroach banks. It all started when a big auto supply company suddenly went bankrupt. And one bank, Jeffries, is set to lose$715 million from that one company. That's when Jamie Dimon, the head of JPMorgan Chase said, where there's one cockroach, there's usually many more. And that's where the risk in finance comes in of contagion. Where there's one bad bank, like a cockroach, there may be many bad banks.
22:44And finally, Mr. Beast filed a trademark for, and I quote, Mr. Beast Financial. That's right. According to a pitch deck seen by Business Insider, Mr. Beast may launch a bank, baby. the YouTube creator does have$500 million in annual revenue this year. And he does love to do things differently. So if he gave away$10 to 10 million people, he would do it all from a helicopter with an ATM card. Now time for the best fact yet, which today is an answer to our T-boy trivia we asked you at the beginning of the show. What is the worst tipping city in the United States? Okay, Jack, what is the answer to worst tipping city?
23:23San Francisco. SF, the only major city in America with an average tip below 19%. It's 18.77 % to be specific. Okay, now in defense to sprinkle on some context, because it just went out in San Francisco last weekend, there are some reasons for this. Like we said, the higher the rent in the city, the lower the tips that people can afford. But also there's a policy reason here. San Francisco restaurants with staff over 20 people have to offer some kind of healthcare to their workers. And many restaurants pass off that cost to the consumer with a fee around 5%. Yeah, so if you go out for dinner at a San Francisco restaurant, there's also maybe a 5 % fee for healthcare on the bill.
24:04So the real tip is basically the tip plus the 5%. So 18.77 % plus 5%, you could argue San Francisco is actually generous, not stingy. San Francisco may be the best tipper in America. I would make that case. We'll roll with it. We'll add them all up. Yetis, you look fantastic today. And if you want to tip Jack and me, we're not going to ask for your money. We would never do that. But we would ask you for a five-star review. That's about as good a tip as you can give. What's the difference between tip and charity? Existential question, story for another pod, Jack. In the meantime, we'd love to see your ratings and reviews.
24:41Jack and I read all of them. Honestly, it makes our day. And as always, we'll see you tomorrow.
24:50And before we go, a happy birthday to legendary Yeti London Zhang over in lovely New York City. And happy birthday to Lauren, who's celebrating at a Blues game in St. Louis, Missouri. And Jack, a shout out to Yeti Maximilian, a legendary Yeti up from the peninsula. I ran into him on the Embarcadero. Great guy. Congratulations to Samira Agarwal in San Francisco, who just got a new job at AssetMark as the chief of staff. Samira, the best of the besties. She's also in our Pop Biz Slack channel. Congratulations, Samira. And to all those Yetis celebrating Diwali today, we wish you a bright and happy fest.
25:25Celebrate the wins. This is Jack. I own stock of Netflix and Nick and I both own stock of Apple. Oh, and I own stock of Lyft too. Bureau Premium Non-Alcoholic Beer. All right, Yetis, 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 Bureau, the premium non-alcoholic beer brand co-founded by Tom Holland.
26:03Yeah, I actually first saw it at my grocery store. Delicious tastes like a celebration. Feels fantastic and looks legit. More 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 ruins with all the taste of a premium lager or IPA, but none of the alcohol, there's no better choice than Biro. 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.
26:34Trust us, we've done it. Only beer we know that actually upgrades the scene like a promotion. So, Basties, if there's a win you're celebrating every day, Bureau is the non-alcoholic brew brand you gotta bring. So use code T-Boy for 20 % off your first order at BureauBrewing.com.
Apple snagged the TV rights to Formula1⌠Because racing is now a luxury fashion product.
Ramp just hired the cast from âThe Officeâ... and got the receipts on your most-expensed meal.
Date-maxxing is viral⌠Medjool date sales hit all-time highs because itâs the 1 fruit winning from Climate Change.
Plus, we found the worst-tipping city in America (this oneâs awkward)...
$AAPL
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