The Best One Yet - 🌁 “LIVE from SF” — AI’s GrandmaSlop. The Gap’s fashiontainment. SaaS’ Swimming-as-a-Service. +Bay Bridge glow up

Episode Date: September 24, 2026

LIVE from the Palace of Fine Arts!The Gap just adopted a teenage boy band that toured summer camps… don’t rent a star, raise one.Grandma slop is the most contentious AI use in America… Boomers use it least and love it most.PE rolled up pool installers, then the cleaners… swimming as a service.Plus, San Francisco has 489 billboards and half of them sell AI.$GPS $POOLGrab your tickets to our next TBOY Live Show on the “IPO Tour: In-Person Offering”Boston 10/14: https://tickets.citywinery.com/event/tboy-the-ipo-tour-in-person-offering-8cdhupSeattle 11/4 (21+): https://www.axs.com/events/1446394/the-best-one-yet-ticketsWant to see the LIVE show in action? Watch it on YouTube or check out the highlights on Instagram @tboypod.And tomorrow we’re publishing our full LIVE interview with special guest Tim Draper, the Godfather of VC.Upgrade to The Best One Yet, our 20 minute daily show here:https://open.spotify.com/episode/6xAfl1lv50TYyJ3SW92cPf?si=vlI42nr8Tmq4wfhmGObmfg Hosted on Acast. See acast.com/privacy for more information.

This is Nick. This is Jack. It's Thursday, the new Friday, September 24th. And today's a live show from San Francisco. Is the best one yet. The top three pop business news stories you need to know today. Jack, this is our in-person offering the IPO tour. Is it time to ring the bell? You may as well hit it. Three fantastic stories for today's show. Jack, what have we got in the T-boy? For our first story, The Gap is so eager to return to its 1990s glory that it's investing in a boy band. It's fashion tainment, honey. The Gap's not renting talent. They're raising it.

For our second story, it's the most contentious new frontier of artificial intelligence. Grandma Slop. Yeah, your Nana is an AI power user, but no one's talking about it. And our third and final story, we need to talk about SaaS. That's swimming as a service. You see, private equity is taken over. equity is taken over the pool industry, but there is one savior. But yet is before we hit that wonderful mix of stories.

Love the mix. The hills are rough, but love the mix, Jack. I want to kick it off with the hero stat. There are 489 billboards in the city of San Francisco. That is 489 giant rectangles covering the city like a young Gary Payton. Open AIs got six of them. Code single owes 19 of them, and only nine of San Francisco's billboards have been vandalized with graffiti according to the Chronicle. But how many of those billboards are for AI companies? Jack, is it 80%, 90%, 173%? You think so. But it's only half, actually. Still, 242 billboards in this town

are promoting artificial intelligence right now. Yep, from Lombard to Golden Gate, from 101 to 280, from the Marina to Marin. It's AI business for your business so you can focus on doing business. If it's not advertising AI, it's advertising a Porsche to someone rolling an AI pre-IPO stock. Oh, and Jack, if that Billboard doesn't have a pun that only engineers understand? Did you even optimize your Q2 marketing budget? Sebasties, forget AI. Billboards are what's booming in San Francisco. Some of them are now charging $250K a month. Yeah, the corner of 101 in the Bay Bridge, that's where you want to be. $3 million a year to display a catchphrase to some PM who's whizzing past in a way mile.

Because 100,000 people pass that billboard every day, and one of them is in charge of the budget for Google's Enterprise ERP. So this could only happen in San Francisco. Yeah. The city that turned a wool shoe company into an AI stock somehow that merged with a crypto startup, which went public via a SPAC. But only after pivoting from a B2B CloudSAS software company. All birds, we miss you and we love you. But Nick lives in San Francisco. I used to live in San Francisco.

We know this city. The boom is bigger than AI, and it's bigger than billboards. It's the home city of blue jeans and Birkenstocks, the Grateful Dead and Barry Bonds. Because when you live in San Francisco, you propose with an aura ring. And then you get married in a-lined Viori leggings. With a wedding party wearing custom Patagonias.

And a honeymoon where you finally use that unlimited PTO for the very first time. Fort Mason Farmer's Market makes you scan your eyeballs to buy blueberries. while the startup down the street is raising a woolly mammoth from the dead. Yes, it is cheaper to just live in one continuous Waymo ride than to split a studio in the marina with three roommates. But Jack, we are recording this show in a palace,

the palace of fine arts in San Francisco. The only publicly accessible literal palace in the United States. Besties, San Francisco is in the middle of a glow-up moment right now. But Nick and I know, you've been shining since the gold rush. Jack, let's it our three stories. Oh, one second. Oh, yeah.

You're getting a phone call? It's hugging face. Hugging face? Oh, shoot. We're getting hacked. All right, show's over. Before this song, two boys from the northeast met in the dawn. Even think they need to practice.

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. First, a quick word from our sponsor. For our first story, The Gap, just financially adopted a brand new boy band called J.Y.T. Just Your Type. It's the 1994 playbook, but instead of renting Missy Elliott, it's raising five teenagers. All right, full disclosure, raise your hand if you work at the Gap.

One, two, Banana Republic, Old Navy. All right, I see a few hoodies. There we go. Last month, Yetis, we told you that the Gap's executive team was obsessed with one year and one year only. 1994. Yeah. The Gap brought back Gap beauty in the same design and packaging as the OG-1994 debut. And they installed a new CEO at Old Navy, the brand Mickey Drexler launched back in 1994. And they announced they're adding outlet stores, which the Gap debuted in 1994.

Now the Gap is making another totally 94 move. investing in a boy band. A completely manufactured boy band. Is there any other kind of boy band, Nick? Well put, Jack, well put. A producer said, I want it that way, basically. So why is the Gap so thirsty for the 90s? Well, the Gap was everything in the 90s.

Not only was I a customer snagging every 16 Husky on the shelf before the other Huskies in the store got them. They retired that size after that. From the year that the band InSink was formed, to the year that Justin Timberlake left the band seven years later, the Gap's revenues tripled. This was the golden era. This, the stock of the Gap, was twice as high in 1999 than it is today.

That was their profit puppy era. But what Carson Daly knew then, you're about to know now. Yeah, boy, fans, they're manufactured. They're completely manufactured. In 1993 and 1995, producers assembled groups of guys that they deemed heartthrobs. There was a recipe like making cookies. These boys became the Backstreet Boys. The Backstreet boys did not know each other, but they did have vocal training, they could read a script, and they had highly frostable hair tips.

Totally. 30 years later, though, it's happening again. Producer-songwriter Freddie Drexler just formed just your type. Or Y-YT for short. We're talking Caden, Tyler, record, Toby, and Brian, they're the boys that can sing, they can dance. You got a visual for us? Oh, yeah. There we go.

Exactly. Now, the producer insists, this is not manufactured. He also auditioned 1,300 kids. Sounds manufactured, but this time, the strategy of assembling a boy band is being remixed. The record industry is collabing with the fashion industry. And our buddies at the Gap won in. They announced Tuesday a multi-year collaboration with the new, JYT. Here's the plan.

The Gap is going to get these boys famous, super famous, but also while wearing their own line of the Gap capsule wardrobe. Okay, but pause the pod. Wildest part, JYT, not famous yet. In fact, they are 16, 17, 18 years. old right now. Do you know how not famous YYT is? This summer, the band did a 24-stop tour of

children's summer camps to build their audience. That's basically Freddy Spaghetti. They're getting out there, baby. But with the Gap, they will graduate to concerts and to malls where they will do meet and greets at the Gap stores. That's the contractual obligation. The Gap is so confident that these

boys can be brute-forced into fame that they've agreed to co-produce a documentary about JYT's ride. A rise that hasn't happened yet. It's like that guy in that movie that does the E-True Hollywood story where E is not even signed up. That thing. So, Jack, could you sprinkle on some more context for us, please?

Gap in the music industry, they go way back. The first Gap store in San Francisco sold records and jeans. They almost called the store PAD because they sold pants and they sold discs. True story. They had buzzy commercials with Madonna, Missy Elliott, L.L. Cooge, Aerosmith. But what's new in today's strategy is something called fashion-tainment. That's the strategy of the new boss, Richard Dixon. You see, Richard Dixon was CEO of Mattel this summer of the Barbie movie,

and he got credit as an executive producer of it. Yep, and he leveraged that fame and the success of the Barbie movie to get hired as the CEO of the Gap. And the stock, it's up 88% since Dick Dixon took over. So to keep the Gap embedded in pop culture, Dixon is hired a chief entertainment officer, something we have never seen from a fact. fashion brand. And they're investing in this brand new seed stage boy band. That was her first move.

So Jack, what's the takeaway for our buddies falling into the gap? This is a new talent strategy. Don't rent a star, raise one. Yeties, the Gap's 90s playbook was renting stars. You paid Madonna, Missy, you LL Cool J, you paid them for the 30-second clip. They were expensive, and then when the commercial ends, so did the relationship. But fashion tamedment flips the business model. The gap gets in on the ground floor before the fame. It's cheaper to sponsor five teams during their summer camp tour than to sponsor one Super Bowl superstar. And Jack, have we seen this before? Yes, we have. The Mickey Mouse Club, they launch Britney, they launched Justin, they launch Christina. See, with enough financial support and marketing brands, you can manufacture fame.

This happened quite recently, actually. The company behind the boy band BTS manufactured the girl brand Katzai, who got a Grammy nomination for Best New Artist last year, and now the GAP is endorsing them as well. You see, in the attention economy, sponsorship endorsement deals, they're more expensive than they ever been. So the Gap is putting all their hoodies on a whole new shopping basket. In the 90s, the GAP rented stars. In 2026, the Gap is raising them. For our second story, the most divisive AI policy in America right now.

On the frontier of technology is Grandma Slop. Specifically, AI-generated images of grandkids by their grandparents. And it explains a huge opportunity for anyone in tech. Now, in podcast standard time, today is Thursday. Yeah, it is exactly two months away from Thanksgiving

when you will go home for the holidays to have a fun feast at mom and dad's house. Okay, but trigger warning, because when you walk in the door, you're not going to see Polaroid picks from the family photo album, you used to. Mom, why is there a picture of us all out of a safari? We've never been to a safari. And why do my eyes look like a luboo doll? Behold, Grandma's Slop. Yep. A whole refrigerator full of

AI-generated images of you and your new girlfriend. Oh, Jack, what if you got kids? Then it's even worse. There is nothing creepier than an AI-generated grand kid pick when they don't even exist. Two toddlers sitting on Santa's lap with huge smiles while riding thoroughbred reindeer to the moon. And the only thing creepier than that is AI images of what your kids would look like if you and your partner actually did have kids. I can't believe people do that. Now, for some reason, Grandpa made his biceps twice as big and added Jerry Rice to photo bomb the family photo. And your mom used up like a whole lakes worth of water and melted a glacier near a data center for this. Just to make the family Christmas card this year.

She loves it. You hate it. Do you want to see what we're talking about in the crowd? You know what you mean? Okay. You got any? Is this like a low-key version? Grandpa, no.

Yeah, yeah. Okay, we've all seen that before. Didn't your mother-in-law make one for you guys? Yeah. I told you about those 45-pound dumbbells, right? Yeah, yeah, yeah. Wait, but did you see what my mother-in-law made from Molly's My honeymoon photo? Nick, this is my Christmas card when we apparently went skiing on Mount Everest.

Yeah. So, now you know. What grandma slop is. A lot of tokens were used in the making of these products. But yes, he's pause the pod. Because Granny Slop exposes an intergenerational technology paradox we have never seen before. Older people are embracing AI-generated image making for e-cards to put on t-shirts, for family portraits. My father-in-law turned every grand kid into a superhero and then printed it on a trucker hat.

But younger people are reacting to AI-generated image generally with an ick. Deleting the cards, tossing out the shirts. And Edna, you got to delete this stuff already. So here's the paradox. Old people are less likely statistically to use AI, but more likely to love it when they do. Just 20% of boomers and older people have used AI image tools, while 76% of Gen Z has. And yet, according to Business Insider, using AI to generate images and post on Facebook gives boomers and people older than boomers the silent generation who are not silent on Facebook. A higher sense of well-being.

While Gen Z has more negative response and a sense. less likely to actually post him after all. So it's wild, but the oldest Americans use AI the least, but love it the most. It doesn't make any sense, Jack. Well, the youngest Americans use AI the most, but love it the least. Now, Jack, we should point out this is partially because young people use it to work, older people are using it for entertainment because they're not working. But still, the irony, the Nana, your Nana is winning the AI Wars.

And that's why the biggest argument this Thanksgiving is not going to be over politics. It's going to be over these picks. This year's holiday card will show you writing an extremely fake rainbow dragon like your Lisa Frank. Honey, I prompted the kids. So, Jack, what's the takeaway for our buddies looking at AI Granny Slop? Every market is actually at least six different markets.

Yeties, in business, you segment. You divide up your customers into groups so you can target them more effectively. Take a look at skin care. Teens get pimple patches, millennials get clean beauty, the elderly get anti-aging, same company, different marketing to different segments. But so far, AI has been launched to everyone with the same exact product. And we think that is a key reason there's been so much thrash.

It's a different story in every other industry. You don't have the one product go to the entire population. Jack, let me whip out the whiteboard here. You know, you got boomers on Facebook, GenX on Reddit, millennials on Instagram, and Gen Z's on TikTok and Snapchat. Social media has segmented well, but AI has not so far. And age is just one way to segment customers. There's a bunch of different variables you could split it up.

Now, Bessie's Jack and I think. I think AI will eventually get there, offer specific products marketing for specific age demos. And we think that's an exciting opportunity for any industry. Think about it. Every industry is actually six different industries. Every market is six different markets. Now a quick word from our sponsor. For our third and final story, we need to talk about SaaS, swimming as a service. America has 10 million pools

And private equity And they want to be the pool boy But there's always room in the pool For the little guy Yeties with the pandemic Work from home Staycation booming Everyone you pimped out your house

But the biggest blurge To make your neighbors jealous on Zillow Forget the fire pit It was the swimming pool You see the quiet pandemic trend That no one knew about Private equity Rold up hundreds of regional mom and pop pool shops

Into what we call big pool Because in 2021 it was the biggest year ever for pool installations in the United States. It was. But then, inflation happened. And suddenly an in-ground pool was $100,000. The number of new pool installs has fallen for five straight years. We're in a hot tub recession, people.

And Pool Corp is a publicly traded company that's proof of the boom and the bust. Yeah. Pool Corp stock is down 70% from its peak. Major shrinkage. I was in the pool. Big pool. Chafed like your thighs with those annoying baggies that come with men's bathing suits that you have to snip out.

That was the experience of this PE experiment in pool installation. But Jack, America has 10 million swimming pools. They all need regular cleaning and regular repair. So right now, private equity is trying to salvage their failed pool install investments with a new thing called SAS. SASS. Swimming as a service. Because buying a pool is discretionary, but upkeep of an existing pool is necessary.

Private equity has been buying up hundreds of local swimming pool cleaning services, according to the financial time. SPS, pool care and pool troopers. Those are two private equity-backed swimming platforms that merged back in February. These service companies, they manage the chemicals, they do the cleaning, they open up the pool in the spring, and they shut it down in the fall. They'll send, you know, a pool boy to go scoop the frog out of your filter. Yes, they will. But the websites of these two PE-backed pool service companies, they have huge sell-your-business buttons right on the homepage. Interesting, Jack, because despite managing 42,000 pools across five different states,

they want to grow their empire. Spounds like a PE roll-up company. It does. Unlike software as a service, swimming as a service is not threatened by artificial intelligence. The only SaaSpocalypse for swimming as a service is like the dad who forgot a swim diaper

for their toddler that day. So the P.E. vacation of the pool maintenance industry, it could be good news for some people. Those mom and pops, for example, they've been running pool companies for decades, but now they can sell, enjoy some early retirement,

go down to Del Boca Vista. Plus, the financial resources of big pool, could improve the customer experience for pool owners. The besties, we know you. Your Instagram feed's probably filled with a list of industry's private equity ruined videos from like the pizza industry to now the pool. Because let's be honest, P.E. has to deliver returns to their Wall Street investors.

And the P.E. managers have to justify their bonuses. One way to do that, Jack. Consolidate the industry, eliminate the local competition so that you can raise prices and cut costs. Oh, is the way Jack and I like to say it on the show. They put pros before coes. They put profits before customers. If this happens, which is not always the outcome of when private equity takes over an industry, it would be capitalism. Yeah, we call that part capitalism.

Not capitalism. Right. Capitalism actually has a short lifespan. There is hope here, and it is our takeaway. So, Jaggle, what's the takeaway for our buddies over in Big Pool? The biggest opportunity for the little guy is when everybody hates the big guy. You see, Yeti's, if this trend continues, in a few years, they're not going to be any locally owned pool companies. It'll just be Big Pool, which will have the power to nickel and dime you to deliver returns to their investors.

Aha. But the answer to capitalism is capitalism. It's competition. Now, one prediction of the AI optimists is that creating a new business will be easier than ever thanks to AI. AI is going to make it easy to form an LLC, manage the books, market online, become a more profitable startup in your own profit puppy era. So one person who's working at Big Pool. could quit, start their own business. More human branding, better customer service, localization, maybe even lower prices because they don't have to deliver returns to PE. There are very low barriers to entry to servicing pools. Big bad monopolies, they just can't hold on to that market in the deep end. It's competition, baby. So ironically, the answer to capitalism is actually

capitalism. A little more capitalism. But besties, this pod's not over yet. We need two volunteers to come up and help us wrap up the show. And I actually, actually think we have both of them in mind. One of them is Brandon Singh from Queens here. There he is. Former colleague of ours at Robinhead. Brandon, come on up here. And then Christina Wynn from down the street in San Francisco, she has the best fact yet. So Brandon, first, the gap is bringing the 90s back by investing in a boy band. It's fashion tainment, honey. This is a new talent strategy. See, don't rent a star, raise one. Second story, grandparents are using AI to generate fake picks of their kids and grandkids.

It's grandma slop. And it proves that in every market, there's actually six different markets. And finally, private equity is targeting a new industry, ZAS, swimming as a service. But see, there's always room in a pool for the little guy. But before we go, time for the best fact yet from Christina Wynn, right down the street. Hi everyone, so the best fact yet. So we've been hearing a lot about San Francisco's current AI boom. What people don't know is SF has always been known as a boom and bust city.

We went from the gold rush in 1849, go 49ers, to total collapse in 1855, then from the total destruction of the 1906 earthquake to building the World Fair in 1915, including this building that we're in right now. the dot com crash in 01 gave us the web 2.0, then the bust of COVID, and now the AI boom. But you could have predicted all of that by simply looking at the official SF city flag. It is literally a phoenix rising from the ash, fire, and ashes, because SF keeps burning down economically or physically, only to rebuild as a center of global capital. Turns out, we're doing the podcast tonight inside the city's greatest monument to comebacks,

The palace we built after the 1906 earthquake. Thank you, Christina. And a round of applause of Brandon and Christina. Give it up from Brandon from Queens and Christina. Thanks, Christina. And while they've done a fantastic job of whipping all that for us, we know there are a lot of celebrations and shoutouts in the audience. So if you've got one, raise your hand,

and we want to get it on the pod right now. Long time fan, we are celebrating our engagement for the next year. We see Nick at the farmers market every single Sunday at Fort Mason. Yes. Hi, this is Cassie from San Francisco, like two blocks away. My older sister, Sammy, and David, have been together 10 years and are getting married on October 10th. 10-10 for 10 years. Hello, my name is Edison.

I'm shouting out my dad, Ed Riojas, who got me into the T-Boy podcast two years ago. Awesome. Thanks, Dad. This is Abonizer over here. He launched his education. for Ethiopian students. He has over 8,000 users and launched it just like a week ago. It's called Tiedel Portal. Jack, I got one over here. Hey, my name is Ben. Just want to say thanks again to Tim, and I want to shout out Arimo AI.

It's a new company for AI adoption in fintech. Hey, my name is Sardor. I'm from Uzbekistan. I want to celebrate the wins of celebrating one-year anniversary with my wonderful life on October 1st. You're the best thing that happened in my life. Thank you. Amazing. Well done. Hi, my name is Amar Kahale from Syria. I want to give a shout out to my father-in-law visiting from Lebanon over there.

And the youngest Yerdi-Yet, my unborn child, there's my wife. She's pregnant. And our son is the youngest Yad-Yad-Yet. Amazing. Congratulations, guys. Hey, and I'm Franklin, and I want to shout out my whole family who's here, including my dad. We're here celebrating his birthday and got him into the podcast several months ago.

So many wins to celebrate. Thank you for everyone who stayed extra late with us tonight. And if we didn't get your shout out, shoot us a DM. We'll make it up for you. We promise on the next episode. But Jack, what a show. Do we do closing bells on the show?

I think we're supposed to do the closing bell for the show. Thank you to the Palace of Fine Arts for hosting us tonight. Thank you to the staff for putting us. on an amazing show. Thank you to Liquid Ivy for being a phenomenal sponsor of this show. Thank you to our editor Trey, who's going to be up till 3 a.m. editing this show, no joke. He is so dedicated. He flew up from Los Angeles just for this. And thank you to you all for letting Nick and me have a phenomenal job. I can't believe this is a job. Tim Draper, the Yetis, the besties. We love doing this. We're never going to stop doing this. Thank you for letting us hang out with them every day.

So, terms and conditions apply. And we just did a whole bunch of shabler. And we just did a whole bunch of shabler. shout outs, but to anyone else celebrating something today, make it a T-boy. Celebrate. Yay! Thank you, San Francisco!