

11 Feb 2026 · 21m · 9 chapters

In this episode, the hosts delve into three major business stories:
Written by AI. May contain mistakes.
Discussion on Eddie Bauer's bankruptcy and its historical significance.
“For our second story, 106-year-old Eddie Bauer just filed for bankruptcy.”
Insight into Indeed's sponsored jobs and their effectiveness in hiring.
“Because sponsored jobs posted directly on Indeed are 95 % more likely to report a hire than non-sponsored jobs.”
Jack discusses a unique financial model for Airbnb hosting.
“This is a job for Indeed-sponsored jobs.”
Exploration of the rapidly growing dating app, Date Drop, and its unique approach.
“the fastest growing dating app in America started at Stanford and has expanded to all the Ivies.”
Reflection on Eddie Bauer's cultural impact and downfall due to mismanagement.
“For our second story, Eddie Bauer went from the outdoor luxury chic of the 90s to bankrupt today.”
Explore MrBeast's new teen finance app and its potential impact on banking.
“Beast just acquired a teen finance app, Step.”
Understand why Eddie Bauer transitioned from luxury to bankruptcy.
“forever bank accounts, and the data proves it.”
Learn about the legal dispute between Cadillac and director Michael Bay over a commercial.
“The GLP-1 drugs that used to cost$1 ,000 a month, just like two years ago, are now available for as little as$50 a month.”
Discover the inspiring story of Robert Smalls, a Civil War hero.
“I mean, can we sprinkle on some context here?”

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. of Stanford students, and it shows the model for 2026 dating. For our second story, 106-year-old Eddie Bauer just filed for bankruptcy. Pour one out for your down jacket. If you want to know what killed Eddie Bauer, it wasn't capitalism. It was crapitalism. And our third and final story, Mr. Beast acquired Step, a teen finance app. The bank of Mr. Beast is now a real thing. And with it, Mr. Beast now has 7 million teens hooked up for 19 years, and we got the data to back that up. But yet is before we hit that wonderful mix of stories. I mean, like we said, P2P, R2P, love the pod, Jack.
1:03We just saw the craziest signal yet of froth in artificial intelligence. Because get this, investors are now offering AI companies 100 year loans. To sprinkle on some context, Google is investing$185 billion this year on AI and data centers. But not even Google is profitable enough to pay for all that, man. So now Google is launching their first ever century bond. I'm sorry, century bond, Jack? An IOU that's not to be paid back for 100 years. A full century. If you buy this bond from Google, you'll see your money again in the year 2126. We repeat, you get paid back in the 22nd century. In 2126, your great, great grandkids will be doing spring break on like Venus.
1:50Jack, in 2026, our hands will have evolved without pinky fingers. But 2026, McDonald's soft serve machines will actually be fixed. And the guac will be free because there won't be any avocados. Besties, most investors don't even know what they're doing this Friday night. And yet they're okay making a date with Google for 100 years from now. Artificial intelligence. Investors want it so badly, they're basically just giving their money away. So besties, if you're still looking for a Valentine's Day gift, fire a Google Century Bond. Because nothing says forever quite like a ridiculous 100-year financial product.
2:21It says our love will outlast Big Tech. I don't know why she walked away. I got her two of them. Jack, let's hit our three stories.
2:54start the show first a quick word from our sponsor
3:03top 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 proud to say that we are hiring right now at t-boy and this is a job for indeed sponsored of jobs. Because sponsored jobs posted directly on Indeed are 95 % more likely to report a hire than non-sponsored jobs. So besties spend less time searching and more time actually interviewing candidates who check all your boxes, less stress, less time, more results.
3:34When you need the right person to cut through the chaos, this is a job for Indeed sponsored jobs. And listeners of the show will get a$75 sponsored job credit to help get your job the premium status it deserves at indeed.com slash podcast. So just go to indeed.com slash podcast right now and support our show by saying you heard about Indeed on this podcast. That's indeed.com slash podcast. Terms and conditions apply. Need a hiring hero? This is a job for Indeed-sponsored jobs. So yeah, he's Jack's instituted a new business model for his Airbnb hosting. And Jack, what is it? Here it is. Host equals guest.
4:08Yes. I funnel all my revenue from being a host on Airbnb into one bank account and use that same bank account to book travel for myself. Basically, it's Jack's host guest bank account for when he hosts and when he's a guest somewhere else. When I lived in the city neck, every time my apartment was available on Airbnb, it would get booked like that. I mean, think about how often are you away from home? You got the bridesmaid, you got the shower, you got the bachelorette, you got the wedding. That's three weekends away just for one wedding right there. Plus, you got to visit your mother. Naturally.
4:37Well, that's a lot of potential hosting that you could be doing on Airbnb, let someone else stay at your place while you're away. Take that host money and spend it when you're a guest somewhere else. Have a business model like me. If you want to travel more, hosting more is a great way to make it happen financially. Your home might be worth more than you think. Find out how much at airbnb.com slash host.
5:00For our first story, the fastest growing dating app in America started at Stanford and has expanded to all the Ivies. It's Daydrop. Why are two-thirds of Stanford undergrads using this dating app? Because Tuesday at 9 p.m. is drop time. Mark your calendars. Yetis, this story really begins with one single graduate student named Henry Wang who built a survey last semester. 66 questions about your values, your lifestyle, and your politics. You fill out the survey, and then he feeds the results into an algorithm. And what's the goal, Jack? Find someone compatible for you to date. Complicated survey, simple formula.
5:35Well, you and that cutie have a 99 % compatibility. You plus me equals us. But here's the key. The app only matches you with one person per week. Okay, but Jack, here's the bigger key. All the matches on the Date Drop app are revealed at the same time, Tuesday, 9 p.m. That's why it's called Date Drop. Exactly. Most dating apps, they are a never-ending scroll of Tinder fatigue sadness out there. Date Drop, on the other hand, has created a weekly event that you get together with your friends for to see who your match is this week. No joke, there are date drop tailgating parties. Jack, what has been the result of this 9 p.m.
6:12Tuesday moment? Super Bowl-level insanity on Tuesday across campus at 9 p.m. Two-thirds of undergrads are using this app. Jack and I dove in T-boy style. The way we see it, this is the La Boo Boo effect in action. It's like a mystery box, but for matching dates. Just like Supreme drop sneakers, they're dropping your future Mr. or Mrs. Right. And we think this is a huge moment. Because like Zuckerberg's Facebook escaped the Harvard campus, Date Drop has hit escape velocity too. That's right. Date Drop is now at all the Ivies at MIT. It is scaling across those schools faster than a nice clean pair of Bochus and Chinos.
6:47Soon you can probably sign up even without a.edu address. Jack, how are MIT engineers hooking up this Valentine's Day? With the date that dropped last night at 9 p.m. on the Date Drop app. And here's the news, Yetis. This isn't just the most viral dating app in America. DateDrop, this one-man startup, just raised$2.1 million in venture capital funding. Yeah, the smart money is on the smart date matching. Maybe an AI Cupid can solve the Tinder fatigue that's been dropping the dating app stocks. But this isn't the first academic love algorithm, is it, Nick? Good point, Jack. Harvard's had their data match since 1994.
7:22Same concept, but that was all on paper with human beings doing the manual matching for that thing. Speaking of Harvard. Yes, Jack? Where Facebook was born in 2004, Date Drop has another wild similarity with Facebook. Jack, are you thinking about accusations of stealing? Because in 2017, the Marriage Pact, was also founded at Stanford, used a very similar questionnaire to do the same thing—find you a date. In fact, the Marriage Pact just sent a cease and desist letter over to Date Drop. But like Zuckerberg said to the Winklevoss twins, Date Drop is saying, talk to my lawyers. I'm not quitting this.
7:56This is my billion dollar idea. But besties, Jack and I were curious. Still, why has this become the fastest growing dating app in America? And the answer, it matches with our takeaway. So Jack, what's the takeaway for our buddies over at Daydrop? The biggest value isn't the product. It's the anticipation. Oh, Yetis. There are just like so many cool forces behind Daydrop. We've told you about some of them. Like how in a world of infinite options, there is power in curation. There's also the Labubu effect, the mystery box concept that Labubu pioneered. That can apply to anything. But fundamental to Date Drop's success is the idea of having to wait an entire week for your first date.
8:31That's right. The real value of Date Drop is not the reveal. It's the seven days leading up to it. Just like HBO stole the zeitgeist for eight weeks with weekly drops of Game of Thrones. Date Drop dominates the zeitgeist on each campus it expands to with Tuesday night Date Drops. So what we're saying is that HBO owns Sundays, Date Drop owns Tuesdays. The Date Drop product may or may not have been copied by someone else's idea. But it doesn't matter because the biggest value isn't the product. It's the anticipation. For our second story, Eddie Bauer went from the outdoor luxury chic of the 90s to bankrupt today.
9:09Pour one out for Eddie Bauer, which rose thanks to capitalism, but fell thanks to crapitalism. Eddie Bauer. I mean, Jack, if we're going to build a Mount Rushmore of outdoor brands based in the Pacific Northwest, they got to be up there. They got to be one of the favorites, right? Yeah, I'm pretty sure they're on there. REI, Columbia, Arcteric, Eddie Bauer. All Pacific Northwest, all punching above their parka. Are you kidding? Filson got snubbed on your list. Oh boy. True, Filson did get snubbed. They were ensconced in flannel. Besties, to research this story, Jack and I went to the About page on eddiebauer.com and sadly it still says, we're just getting started.
9:47Sadly, because actually the business is over. True. The brand founded by the man of the same name, Eddie Bauer, In 1923, he just declared bankruptcy. Thank you for clarifying his name, Jack. Eddie Bauer founded that company in 1923 after he contracted hypothermia on a winter fishing trip up in the state of Washington. He nearly died, so he created technical outdoor apparel to help future fishermen and outdoorsmen. Then he got life insurance, and then Eddie Bauer patented the first ever down jacket, hence their logo being a goose. Eddie Bauer also outfitted the first American to ever climb Mount Everest.
10:19and outfitted the U.S. Army for their first Air Force bomber jackets during World War II. But the symbolic summit of their business was in the year 2002, when they had 500 stores. It's all been downhill from there. Since then, because on Tuesday, Eddie Bauer announced bankruptcy. They're closing their Seattle headquarters and 200 stores unless they can get a buyer ASAP. RIP, Eddie Bauer. But we're going to relive their glory days. Yeah, Jack, take us back to the 90s when we were growing up, man. Eddie Bauer pioneered a concept that has inspired Kim Kardashian today. The collab. The collab. It begins with Eddie Bauer.
10:53You see, Eddie Bauer, his son, and later General Mills and a company called Spiegel all owned the business in the 20th century. All of those Eddie Bauer owners invested money, took risks, innovated the brand and product, and launched and delivered profits. Including the first collabs. Like in 1984, they launched the Eddie Bauer Edition Ford Bronco, Ford Explorer, and later Ford Expedition cars. From 1984 to 2010, high-end Eddie Bauer edition Fords turned heads in the ski mountain drop-off zone. I mean, Jack, nothing pairs better with a third home at Stowe than an Eddie Bauer Ford vehicle. The two-tone color on the outside, the leather interior on the inside.
11:32But they didn't stop there. Eddie Bauer launched Eddie Bauer Home, a warm and cozy home goods business through a partnership with Lane Furniture. They also launched Eddie Bauer Optics, collab sunglasses in partnership with Oakley. And they launched Eddie Bauer Mountain Bikes in partnership with Giant Mountain Bike Company. Today, it's Skims partnering with everybody. 25 years ago, it was Eddie Bauer partnering with everybody. But Jack, we should point out, starting in 2003, Eddie Bauer kind of became, well, it became a corporate orphan. Because its owner at the time, Spiegel, declared bankruptcy due to an unrelated credit card business that was poorly managed.
12:04What was the result, Jack? For the last 23 years, Eddie Bauer's owners were focused on cutting instead of adding. Basically, corporate hypothermia. So Jack, what's the takeaway for our buddies over at Eddie Bauer? New term, capitalism. When PE sucks away all the value from a business. Yetis, from 2003 to 2009, Eddie Bauer was owned by Wall Street banks, who they just wanted to get their money back. And after that, it was owned by a PE company and what's essentially another PE company. Now, the interesting thing about private equity is their business model is kind of like house flippers. They buy a bad company, they make it good, and then they sell as a profit.
12:39Yeah, sometimes they do that, Nick. But other times they buy a good house, they don't give it the upgrades it needs, they neglect it, they extract all the value from it, like the copper pipes inside, and leave the house for dead. Well, that's the position Eddie Bauer found itself in. It had become a brand of suburban malls. It wasn't cool, it wasn't trendy, it was simply meh when private equity took over. So did those PE owners invest in e-commerce to revive the brand's growth? No, they didn't. Nope, they set up an Amazon page and visits to EddieBauer.com fell and flatlined for 10 years. Did they invest in fulfillment to meet the higher expectations of consumers in the e-commerce era?
13:14No, they didn't. Nope. According to the Trustpilot, bad customer service gave Eddie Bauer just 1.3 stars out of 5 stars. Did they sign Bear Grylls as a sponsorship dude to try to bring some cool back to the brand? Obvious move. I love your call, Jack. No, they didn't. Eddie Bauer became not cool with bad customer service and the result was bankruptcy. What Eddie Bauer needed was capitalism, investments into the business for long-term growth. But what it got was crapitalism. Private equity hollowed out the brand like a carcass in the woods. Now, a quick word from our sponsor. Monarch. When I had student debt, I tracked my progress on an Excel spreadsheet I manually updated each month.
13:55Oh, I was Jack a spreadsheet jockey because when he was paying off his student debt, Monarch didn't exist yet. Well, one year ago, I proudly killed that spreadsheet I'd been building for 12 years. RIP spreadsheet. Because Monarch is a way better solution. All your financial accounts are linked to Monarch. Every credit card, checking account, brokerage account, even our mortgages, live balances updated in real time. I'm still paying down my mortgage and Monarch gives me the visibility and tools to do it. You can use it too. Create savings buckets and financial goals in Monarch. Set yourself up for financial success this year.
14:27Are you familiar with the Sankey diagram? I had no idea what it was, Jack. Well, once you see it, you can't unsee it. It's brilliant. And Monarch visually shows you what you're spending. And we did not make up that term. Your investment portfolio, Monarch compares it to the S &P 500 for you. Set yourself up for financial success in 2026 with Monarch, the all-in-one tool that makes proactive money management simple all year long. Use code TBOY at Monarch.com for half off your first year. That's 50 % off your first year at Monarch.com with code TBOY. NetSuite by Oracle. Yetis on our show, you know, we love to sprinkle on some context.
14:58Because news doesn't mean anything if you don't have a sense of history, the competitive situation, etc. Yada, yada, yada. Well, it's the same with AI. If your AI tool doesn't know anything about your biz, then it's not going to be the best one yet. That's why we're pumped to promote NetSuite by Oracle. It's helping over 43 ,000 businesses figure out how AI can work for them. NetSuite is actually the number one cloud ERP connected to your entire enterprise. It has your data on financials, HR, inventory, commerce, and CRM. To be honest, it's probably going to have to sprinkle on context about your business to you.
15:29It's that intelligent. That connected data is what makes your AI smarter. So it doesn't just guess, it knows. This isn't another bolted on tool. It's AI built into the system that runs your business. So whether your company earns millions or even hundreds of millions, NetSuite helps you stay ahead. If your revenues are at least in the seven figures, get your free business guide, Demystifying AI at netsuite.com slash tboy. The guide is free to use at netsuite.com slash tboy. NetSuite.com slash TBOI. For our third and final story, Mr. Beast just acquired a teen finance app, Step. The bank of Mr.
16:04Beast is now officially a thing. By switching to teen bank accounts, Mr. Beast is pivoting from attention to retention. Yetis, last year Jack and I dove in T-boy style to the old U.S. Patent and Trademark Office. And what did we notice about a curious Mr. Beast trademark application? MrBeast Financial. The man with 500 million followers had the intention to enter, quote, banking, investment, and crypto services. I just dropped a golden ticket in a room full of scorpions. If you find it first, you get a high-yield savings account. Is that the business model? First one to tackle Jamie Dimon wins a billion dollars!
16:39I'm going to bury myself alive. But now we're seeing why. Because the world's most popular YouTuber acquired Step this week, a teen finance app with 7 million users. I'm sorry, Jack, pause the pod. Beast Industries' other ventures include Feastables, a snack brand, Beast Philanthropy, its non-profit arm, Beast Games, a reality competition series on Amazon Prime Video. Plus the Profit Puppy, the YouTube channel. Next up, Mr. Beast plans to launch a wireless service, basically a viral version of Verizon. Mr. Beast is becoming the Unilever of Gen Z. But Step is the first business he's acquired instead of building from scratch.
17:15And since Jack and I sold the business to Robinhood and were there for three years, we know a thing or two about fintech apps. So we're jumping in T-boy style to this latest Mr. Beast acquisition. You see, besties, there's an ironic plot twist here about the financial technology app Step. It's funded by the new money. Step is backed by celebrities who got rich young, but were never taught how to manage their money. Alex Rodriguez, Steph Curry, Jared Leto, Will Smith, the Chainsmokers, Charlie D 'Amelio, each of whom wishes they could have taught their younger selves what to do with money. Step tries to do that for them or improve the financial future of the next generation, as they put it.
17:49Yeah, it's Mr. Beast lined. But funny thing Jack and I have noticed over the years about fintech apps. To understand the target of a fintech app, look at the iPhone sample mock-up on their website. You see, every fintech company, from Robinhood to Coinbase to Brex to Ramp, they show a mock-up of the user account and how it looks on an iPhone on the website. And whatever balance they show on that sample picture of the app on an iPhone on their website, that's the signal. That tells you who they're really targeting. Does the mock-up show an account balance of$1 ,000,$100 ,000,$1 million? Well, on Step's website, its sample user has an account with$50?
18:27Yes, because this is for teens. They have 7 million teens signed up. That's a lot, but Hedris will point out that the typical user has just 50 bucks or so. So the big question, how will Step and Mr. Beast make money off of a 15-year-old who only has allowance money. Like, can Mr. Beast build a business based on Girl Scout cookie sales? Jack, what's the takeaway for our buddy, Mr. Beast? Teen bank accounts are forever bank accounts, and the data proves it. Yeti, Jack and I have shared with you the window of loyalty. We know you love that takeaway. Basically, brands want to win the love of young people because that love lasts a lifetime.
19:04Nobody loves their banks, to be clear, but bank relationships last a lifetime too. According to a recent survey of 1 ,000 Americans, 50 % of people considered switching banks in the last year. But the majority of those people opted not to because it was way too much of a hassle to switch your primary bank. Didn't you like consider doing this the other day and then after six hours gave up? I was tempted by a bank that would give me 3 % interest, even on my checking account. But Nick, I have 30 automatic payments going in or out every given month. That's the Hotel California situation. You can check out anytime you like, but you can never leave.
19:36The result? According to Bankrate, the average checking account in America is held for 19 years. Years, besties. Mr. Beast will try to boost the 7 million users of Step to 70 million by promoting it across his social channels and investing in new features. J.P. Morgan and Charles Schwab, they don't care about$50 bank accounts. No, they don't. But teen bank accounts are often forever bank accounts, and the data proves it. Jack, could you whip up the takeaways for us for ceviche Wednesday. Date Drop is used by 5 ,000 of Stanford's 7 ,000 undergraduate students. Basically the entire single population on campus.
20:14The product didn't make it go viral. It's the seven days of anticipation that did. For our second story, Eddie Bauer was the epitome of outdoor luxury chic in the 1990s, but today it's bankrupt. Capitalism powered its rise, but crapitalism powered its fall. And our third and final story, Beast Industries now owns Step, The fintech app targeting people in their teens and 20s. And those same teen users today will be Titan users in 20 years. And then Mr. Beast will add this to every app. Exactly. But besties, this pod's not over yet. Here's what else you need to know today. First, a happy heavy earnings week to all those who celebrate.
20:50Spotify stock jumped 15 % because users were just all ignoring that price hike apparently. Robinhood stock fell yesterday as the fall in crypto prices has suppressed trading activity. And Lyft dropped. Lyft is now worth just one Lyft because they did launch teen accounts, but that was two years later than their rival Uber. Second, Hinz & Hers and Novo Nordisk stock have lost so much value, you'd think they're on Ozempic. Yeah, get this. Both of these GLP-1 companies have GLP-1 miracle weight loss drugs, but both stocks are off 65 % from their all-time highs. Why? The GLP-1 drugs that used to cost$1 ,000 a month, just like two years ago, are now available for as little as$50 a month.
21:32It's a weight loss drug price war. Great for consumers, but terrible for profits and shareholders. And finally, more Super Bowl drama. Michael Bay is suing Cadillac, claiming that Cadillac stole his ideas for their Super Bowl commercial. You see, Cadillac is the new F1 racing team with their first ever Grand Prix coming up this March 6th. And to get Americans hyped about it, they talked to Michael Bay, the famous director of all those Transformers movies. But then Cadillac didn't end up hiring Michael Bay to do their Super Bowl commercial. They allegedly stole his ideas and used them in the ad instead.
22:04Not cool, Cadillac. Not cool, if true. Now time for the best fact yet. This one sent in by Savannah Westwood from lovely Orlando, Florida. And earlier this week, we told you it was the 100th birthday of Black History Month. So Savannah got us a good one. Savannah's fact is about Robert Smalls, who became the first black captain to command a U.S. naval vessel after he stole a Confederate ship during the Civil War. I mean, can we sprinkle on some context here? 1862, this enslaved man takes a Confederate ship and then delivers all its cargo up to the North, to the Union forces. And his bravery helped convince President Lincoln to allow black men to serve in the U.S.
22:46Navy and in the U.S. Army. But Robert Smalls didn't stop there. He eventually went on to become a congressman for the state of South Carolina in the U.S. House of Representatives, and he did it for nine years. Small and last name, huge in accomplishments. Yetis, you are looking fantastic for ceviche. Wednesday, Jack, you are glowing over there too. And what is the best way to help grow the show? Share the show with your friend who would love the best one yet. H-Y-H-T-B-O-Y, that's how we grow the show. What does that stand for? Have you had the best one yet? Drop a link to today's episode in your group chat.
23:18Then, if you really wanna nail Valentine's Day, buy that Google 100-year bond. Your great, great, great, great, great grandchildren will appreciate it. And that's what you put in the note. You nailed it, Jack. That's what you put in the note. Jack and I will see you tomorrow.
23:37And before we go, a happy birthday and congratulations to Yeti Avery Walton in Kingwood, Texas. She's getting married next month to a dude named Nick, and she is on a roll right now. Happy 48th birthday to Fred Valleys in California, who's listened to 500 episodes of this pod. And Josh Platts has a birthday and a new job over in Beaver, Pennsylvania. Happy birthday to Jessica Fishler, listening on her commute right now in Atlanta, Georgia. And Dinesh Barvani and his mother-in-law are enjoying the same best birthday in El Segundo, California. Happy birthday to Ryder Pang, turning a big eight years old in California.
24:10And Molly No Diff has got a great name and a great birthday celebrating in New York City. And happy birthday to Emily Brines, the best high school teacher at WHS, who's turning 30 in Westminster, Maryland. And a shout out to Terrell Caraman, who's driving their daughter to school and just got promoted in Fresno, California. Happy three-year wedding anniversary to Ryan and Rachel down in Atlanta. And Caroline and Nick Alves just got engaged in December, and Jack, they already chose the wedding venue. Congratulations. That's the hardest part.
24:41This is Jack. I own stock of Amazon and Lyft, and Nick and I both own stock Robinhood and Spotify. Over 90 of the top 100 U.S. accounting firms trust Bill to handle BillPay processes. Why? Because our tools are built on over a trillion dollars of secure payments. We're not just moving money. We're powering financial workflows for half a million customers. That's a level of expertise you just can't fake. Ready to talk with an expert? Visit bill.com slash proven to get started and grab a$250 gift card as a thank you. Terms and conditions apply. See offer page for details.
Eddie Bauer rose thanks to capitalism... It’s now bankrupt thanks to “Crapitalism.”
72% of Stanford undergrads are using Date Drop… It’s taken over Tuesday nights.
MrBeast bought Step, a Fintech app for teens… but they’ll be customers for 19 more years.
Plus, AI demand is so crazy Google dropped a Century Bond… Get paid back in the year 2126 (it’s a great Valentine’s Day gift)
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