

29 Oct 2025 · 23m · 11 chapters

Three business/tech stories plus market context: Airbnb’s AI “anti-party police” for Halloween, Amazon’s layoffs amid a broader “great hiring freeze,” and Wikipedia’s traffic decline as AI chatbots and Elon’s Grokipedia compete.
No guests mentioned; it’s hosted by Nick and Jack (podcast hosts).
Not applicable (no guest interviews).
Airbnb will use AI to block likely Halloween party bookings (e.g., red flags like booking near your home, cheaper-than-usual stays, or one-night Friday Oct 31 bookings) and offer hosts noise detectors. Amazon laid off 14,000; CEOs are increasingly keeping headcount flat by not hiring. Wikipedia human page views are down 8% as bots/AI chatbots crawl it; Elon launched Grokipedia, a Grok-moderated clone.
Airbnb blocked 38,000 parties last Halloween; Amazon plans to avoid hiring 600,000 warehouse workers by 2033; ChatGPT surpassed Wikipedia in top-10 traffic.
Written by AI. May contain mistakes.
Discussion on Airbnb's plans to use AI to prevent Halloween parties amidst a tough market.
“For our first story, Airbnb just announced a plan to use AI to prevent Halloween parties.”
Explaining Amazon's layoffs and the broader trend of companies not hiring due to AI.
“Now, if stocks rose that much every trading day of the year, what kind of numbers, Jack?”
Insights on historical stock performance related to October 28th, both good and bad.
“If you know, you know, cause we ready to go.”
The hosts introduce a story about Airbnb's AI party police for Halloween and discuss the company's lagging stock and recent marketing moves.
“They're already a notorious party pooper, but they just announced special plans to stop Halloween parties this year.”
Discussion on Airbnb's measures to prevent parties using AI and its implications.
“So you can invite everyone you know to somebody else's place to have a rager.”
Examining the economic implications of layoffs and the use of AI in companies.
“So we'll explain this current moment in the economy, the great freeze.”
Explore how AI is influencing the job market, including job losses and the 'great freeze'.
“the workforce band-aid and replacing workers right now with AI agents.”
Discuss the decline in Wikipedia's user traffic and the emergence of Grokipedia.
“So we looked at Wikipedia's greatest accomplishment.”
Summarize the main stories of the episode, including hiring freeze and Wikipedia's challenges.
“Airbnb is amping up its anti-party policies this Halloween with preventative AI that happens before the booking.”
Receive updates on major companies' earnings and the Federal Reserve's decisions.
“Here's what else you need to know today.”
Celebrate listeners' achievements and share personal stories about the podcast.
“So Europe changed their clocks last weekend.”

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. They're looking fantastic. If you want to join, we're opening it up. Tap the link. It's on Slack. We'd love to see you there. Yeah, we post our thoughts on stories for the day, some other pop biz headlines, what we're thinking on the show about business and stuff. So check it out. In the meantime, though, Jack, three fantastic stories for today's pod. What do we got on the T-boy? For our first story, Airbnb just announced a plan to use AI to prevent Halloween parties. Ah, Airbnb. It's the anti-party police party pooper because right now, Airbnb needs to show the host some love. For our second story, Amazon announced yesterday 14 ,000 layoffs.
1:08It's the biggest AI-caused job loss so far. But besties Jack and I got your back, so we'll tell you how to prep for the great hiring freeze. And our third and final story. For the first time ever, visits to Wikipedia are falling right now. And Elon just launched his own Wikipedia called Grokipedia to take on Wikipedia. So what happens when the disruptor gets disrupted? The answer is not in Encyclopedia Britannica. No, we looked in Wikipedia. We may have found the answer in Wikipedia. But yet is before we hit that wonderful mix of stories. Wow, I mean, what a mix of stories. Love the mix for Ceviche Wednesday, Jack.
1:43Congratulations. Yesterday was the best one yet, at least for Wall Street. Literally, October 28th, the best day of the year. four stocks. Historically speaking, Nick's a history major, by the way, so he fact-checked this. Stocks perform best on October 28th. Jack, could I sprinkle on a little context myself today here? Can I do that for you? Okay. Going back to 1950, the S &P 500 rises 0.54 % on average October 28th. Now, if stocks rose that much every trading day of the year, what kind of numbers, Jack? They'd be up 288 % at the end of each year. Why can't we just call every day 1028? I mean, it just works.
2:22Well, yesterday, the streak continued. Stocks rose 0.23%. Jack, another 1028, another win. We should stop asking, is the Pope Catholic? Oh yeah, instead just ask, do stocks rise on October 20th? The answer is yes. And this year, stocks didn't just rise, they rose to a record. Get this, Apple, their stock hit a$4 trillion valuation yesterday. For the first time. And Microsoft hit a$4 trillion valuation yesterday day two. Jack Peloton stock? Actually, it fell yesterday. It went down, but it almost went up. It almost went up yesterday. It was October 28th. Long-term hold. I don't know why we're still holding.
2:58Anyway, here's the kicker. You know what else happened on 10-28? Not the best day of the year, Jack. The worst day in stock market history. It's wild. But the day that triggered a financial crisis that became the Great Depression? Yes, that started on October 28th, 1929. Okay, things just got spooky. Jack, the ghost of bull markets past. October 28th, either the best day yet or the worst day yet. But yesterday's October 28th happened to be the best one yet of the best ones yet. Except for Peloton. Yeah. This isn't financial advice, besties, but let's get on three stories.
3:45I 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.
4:00Start the show. First, a quick word from our sponsor.
4:11gusto one sec yetis we just need to take a break from the pod for a moment to find that i9c3 irs tax form for each employee and then jack we got to make sure each co-worker 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 Charges 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. Oh boy, if you're a small business, you'll want to outsource all that to Gusto.
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5:21That's three months of 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. Yeah, 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. We're excited that listeners of this show can get your first year of Monarch Core for half off.
5:56That's just 50 bucks with promo code TBOY. The weekly spending recap, it 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 TBOY at monarch.com to get your first year of Monarch Core half off at just 50 bucks. For our first story, Airbnb.
6:31They're already a notorious party pooper, but they just announced special plans to stop Halloween parties this year. It's the AI party police, a move that hosts are gonna love, but guests are gonna hate. That's the controversy. But besties, first, Jack and I can tell you as a couple Airbnb shareholders, Airbnb stock this year has been the real estate equivalent of a four-floor walk-up in the East Village, right, Jack? Jack? Is the elevator broken? Because while the rest of the stock market is up 17 % so far this year, Airbnb stock is down 2%. So this year, Airbnb relaunched experiences to drive excitement.
7:10That's fun. They also did a paid product placement in an episode of Nobody Wants This on Netflix. Yeah, that pasta making event, Airbnb probably paid for that. But the latest news from Airbnb is It's less fun, right, Jack? Less fun. Airbnb does not want you to party this Halloween. Here's the press release from Airbnb. We are rolling out our anti-party system for Halloween, and this time, oh, they're using artificial intelligence. Everybody likes the cool mom, but Airbnb will have none of it this Friday. I said curfew, kids. Jack, could you sprinkle on some context here to what is going on with all of this?
7:49You and I coined the phrase party pooper policies going back to 2020 when it comes to Airbnb. That's when COVID parties were happening at Airbnb properties and they were like super spreader events. So Airbnb banned parties globally and they suspended or blocked and banned people who violated this rule. The reason? Hosts don't want keg stands happening at their place. No, they don't. Also, neighbors hate when Airbnb properties have parties at them. Yes, they do. And that's when damage happens to properties. It's a huge insurance liability if a party's going on. Get this. Last Halloween, Airbnb blocked 38 ,000 parties in America, according to their own data.
8:29But here's the update. This Halloween, Airbnb is deploying preventative anti-rager technology. Yeah, we call this one ART, ART, anti-rager technology. How does this break down exactly, Jack? It's artificial intelligence that will predict that this booking that's about to happen, It's definitely for a party, so we're going to block it altogether. Basically, it's going to use AI to determine red flags. Like if you book an Airbnb near where you live, why is that a red flag, Jack? Why would you do that? So you can invite everyone you know to somebody else's place to have a rager. Or Jack, what if you book a cheaper house than you typically do from your booking history?
9:07That's also a red flag that might trigger a blockage. Or Jack, what if you book one night and one night only, and that night is Friday, October 31st? That's the biggest red flag of them all. That is a huge, huge red flag. Besties, Airbnb is even offering hosts noise detectors that'll notify you when a certain decibel level is hit. You get an Airbnb notification. Someone just yelled flip cup. We thought you'd want to know. Oh, you do want to know. Add it all up, Besties, and Airbnb has become the chaperone at your school booking dance. But instead of the gym teacher, it's AI. That's the chaperone.
9:42I'm not going to call this a surveillance date, Jack, Jack, but it's CIA worthy. It is CIA worthy. So Jack, what's the takeaway for our buddies over at Airbnb? Platforms are like parents. You can have a favorite child, but you can't let them know about it. Yetis, a wild detail Jack and I remembered from five years ago when Airbnb IPO'd, and we covered it on the pod. We said Airbnb was focused on its hosts over its guests. Because Airbnb mentioned the word host over 1 ,000 times in their IPO paperwork. That's nearly twice as many times as they mentioned the word guest. Absolutely. But in the last couple of years, guests have become frustrated with booking fees and the owner is checkout instructions.
10:23So some travelers are defecting back to hotels. That's why Airbnb announced a pro guest move this summer. Yes, they did. They shifted the fee that Airbnb takes entirely to the host in most cases, instead of taking a fee from both the host and the guest. Okay, but now the hosts are upset. So Airbnb is making a host-friendly move here. the AI Halloween Party Police. A big, splashy PR campaign that shows hosts Airbnb cares about your property. Besties, corporate goals, they change every year. Airbnb, Uber, Etsy, they shift their focus from one side of their platform to the other all the time. Because a platform is like a parent.
11:01It can have a favorite child. Although, full disclosure, I wouldn't say that I do. I love all my kids equally. But you can't show that you have a favorite child.
11:14For our second story, Amazon is laying off 14 ,000 people. UPS just laid off 48 ,000 people. But the key isn't the firing. It's the lack of hiring. So we'll explain this current moment in the economy, the great freeze. Oh, Jack, how about we start this story with a little bit of corporate jargon? What do you got, man? Staying nimble and continuing to strengthen our organizations. That was the email. sent by Amazon's HR team yesterday. To translate this into Tinder terminology, that's corporate jargon for, it's not you, it's me. Right, but we are breaking up. Yes. Because Amazon sent that email yesterday to 350 ,000 employees.
11:56And in the email, they said they're laying off 14 ,000 workers. But surprisingly, in that entire email, Amazon only mentioned AI once. Multiple reports say that because of AI, this is just the beginning. Total layoffs at Amazon will hit 30 ,000 people, which is almost 10 % of their white-collar workforce. We bet some of our listeners are affected. We know some of our listeners are affected, and we absolutely feel for you right now if you got that email. We also, unfortunately, could have seen this coming because we've said before that AI is like corporate Ozempic. It's like corporate financial magic.
12:29It lets companies get leaner faster. And unsurprisingly, Wall Street rewarded the news. Amazon rose 3 % so far this week. they're just a smidge off their all-time highs. But besties, here's what Jack and I find fascinating about this story. Most companies right now are avoiding layoffs. Instead, they're growing without hiring. It's a new thing called the great freeze. The great freeze. Let's start by sprinkling on some context. Jack, why don't you take it from here? CEOs across corporate America are bullish right now. They believe that the future is full of profit puppies. Okay, but here's the key.
13:02They're not growing their workforce for this big, exciting future. they're using AI instead right now. And we've got their receipts. Walmart's CEO said last month that they will keep their headcount flat for the next three years, despite expectations for huge growth. Jack, how about JP Morgan? They just told their managers to not hire people. Instead, try to use AI first. And although Amazon just did lay off 14 ,000 people, their biggest AI workforce plans involve simply not hiring new people. Yeah, there was that bombshell report from the New York Times just last week. We didn't cover it on the pod, but Jack, what was in that report?
13:39Amazon plans to ship twice as many packages in 2033 as they do today. That sounds good. But they plan to do so with the same number of human workers that they have today. Translation, Jack? Thanks to robots and artificial intelligence, Amazon will avoid hiring 600 ,000 warehouse workers. Now, Yetis, some companies are ripping off the workforce band-aid and replacing workers right now with AI agents. But most are doing it more subtly by simply not hiring and letting their workforce shrink through retirements and voluntary departures. Now, this is not a fun story. Like, what does this mean for you?
14:15It's a scary time out there for a lot of people. Here's the leading theories about how AI is affecting the workforce in our takeaway. And here's how we think you can best prepare. So Jack, what's the takeaway for our buddies who are everyone in the economy? Here's the bull case, the bear case, and the base case of AI taking over jobs. Now, Yetis, the short answer here is we don't know how the jobs market will change because of AI. We just don't know. Nobody knows. Nobody does. And anyone who tells you they know is lying. They can't know. The whole country is anxiety maxing because of it. Okay, but the bull case is that everyone wins.
14:53And we see this reflected in venture capital communications, the White House. Sam Altman loves saying this all the time. Here's Sam Altman's analogy. He says that AI is like electricity. Sure, it put lamplighters out of work who used to go block by block with a fire to light the posts, but electricity created entirely new industries, and so will AI. Now, that's the bull case, the optimistic case. The bear case, the negative case, though, comes from another CEO in the AI industry. That would be Anthropics' Dario Amadei, who says that within five years, the unemployment rate in America will double because of AI.
15:27And the first jobs to go, unfortunately, entry-level white-collar jobs are going to be the ones eliminated most likely. And looking at the data, the unemployment rate for recent college grads is rising faster than the rest of the population. But there is a base case here, the expected case. And you know what? It's that we don't know, but we'll figure it out as we go along. For now, the status quo is being referred to as the great freeze. The great freeze. People aren't quitting, but companies aren't hiring. And we'll cover more as it comes along. Now, a quick word from our sponsor.
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17:59Check Decagon out at decagon.ai slash tboy. That's decagon.ai slash tboy. For our third and final story, Wikipedia just said that for the first time since it was created, traffic to Wikipedia is actually down. So we looked at Wikipedia's greatest accomplishment. Yes, we did. Becoming the world's best source of truth. Yeti's Wired magazine once called Wikipedia the last best place on earth. Because there's no AI slap, there's no ads you have to X out of, and there's no addictive algorithm either. According to Wikipedia, Wikipedia is the ninth most visited site in the world. Wikipedia gets 10 ,000 views every second.
18:44True story. 300 different languages have their own Wikipedia. I didn't know there were 300 different languages. The English language Wikipedia gets 500 new Wikipedia pages every single day. By the way, the Wikipedia page about Wikipedia is the most viewed page of all time. Yeah, we discovered that by going down a Wikipedia rabbit hole, researching the story for a little bit of Wikipedia roulette. But what makes Wikipedia so powerful? It's its business model. Because Wikipedia doesn't have a business model. Wikipedia is decentralized and not-for-profit. It lives off donations and it's updated by volunteer editors.
19:20Founded in 2001 by Jimmy Wales and a philosophy PhD, they started writing 21 articles of a new digital encyclopedia, and then they gave up. It was too hard. It was taking too long. So they basically crowdsourced the whole thing, let others edit and fact check articles, and then added the word wiki to the front name because that means quick in Hawaiian. And the closest model to Wikipedia is Bitcoin. Yes, it is, Jack. Well put. It's internet-based. No single entity controls it. It's democratized for all to use. But besties, here's the news. For the first time in Wikipedia's 24-year history, page views are actually falling.
19:55Specifically, page views by humans. Get this. Human page views to Wikipedia are down in the last few months 8 % from last year. But here's the strange part. Wikipedia noticed a surge in page views overall, but they weren't humans. Nope. They were bots. Bots, AI chatbots, they've been crawling Wikipedia to answer users' questions instead of the users. Relatedly, ChatGPT just passed Wikipedia in the top 10 list of most visited websites. So first, Wikipedia disrupted Encyclopedia Britannica, but now Wikipedia is getting disrupted by artificial intelligence. And Jack, it's not just being upstreamed by chatbots.
20:37Wikipedia is now facing new competition as well. In the form of Grokipedia. Because yesterday, Elon Musk launched his own version of Wikipedia, powered by Grok, the AI chatbot that Elon owns and controls. It's not moderated by volunteer humans. It's moderated by his chatbot. Now, interestingly, Jimmy Wales, the founder of Wikipedia, told the New York Times he's in touch with Elon, and they text about this kind of stuff frequently. But Elon thinks that Wikipedia is biased, so he cloned it. And if you look at Grokipedia, it's mostly a copy of Wikipedia. In fact, some pages are exactly the same word for word.
21:12So Jack, what's the takeaway for our buddies over at Wikipedia? Wikipedia's great success is going from banned to becoming the backbone of the internet. Yeti's society has fascinatingly taken a full circle reversal in how we view Wikipedia. In the 2000s, Wikipedia was banned in schools. Teachers forbid Wikipedia from being used as a source. Jack, do you remember what our professors told us in college? you're not allowed to cite Wikipedia because, quote, anyone can edit it. We had to like go down to the footnotes and go to the primary source and hope that that website still existed. Okay, but 15 years later, there is no more widely accepted source of truth on the internet than Wikipedia.
21:53To prove to your buddy that you were right about that thing, you screenshot Wikipedia and you send it to him and say, see, Wikipedia, it's now cited in court documents, in scientific papers. It is the key source to training artificial intelligence. It's decentralized nature engenders trust. There's no media mogul with an agenda behind it. It's just the masses, and there's strength in those large numbers. Besties, society's initial skepticism and eventual embrace of Wikipedia, it may actually foretell how we handle AI as well. Wikipedia, it had the biggest PR rebrand ever. Yeah, it did. From not credible to the internet's most credible source of truth.
22:31Band to backbone. Jack, could you all whip up the takeaways for us for Saviche Wednesday? Airbnb is amping up its anti-party policies this Halloween with preventative AI that happens before the booking. Because platforms are like parents. They can have a favorite child, but you just can't show it. For our second story, Amazon is laying off 14 ,000 people because of AI, but most companies are simply not hiring instead. AI could someday create more jobs or result in less. Since we don't know, though, we're in the middle of the great freeze. And our third and final story is Wikipedia. They're facing big challenges today from none other than AI and Elon's new Grokipedia.
23:14Wikipedia's great success, though, is going from band to backbone of the internet. But besties, this pod's not over yet. Here's what else you need to know today. First, we get the epic serving of earnings. Google, Meta, Microsoft, all reporting today. That is 15 % of the S &P 500's value in just three companies. They're all announcing earnings. Also, we're getting the big Fed meeting today. Jerry Powell expected to drop interest rates. Wall Street is nearly certain that we're going to get a 0.25 % interest rate cut today. And second, OpenAI just finished its big thing. They completed their for-profit transition, no longer pretending to not care about profits.
23:52There you go. Yeah, the new corporate structure has Microsoft as the biggest shareholder of OpenAI, owning 27 % of the company. Now, interestingly, the old OpenAI, the nonprofit one, it's going to still own 26 % of the for-profit OpenAI. And 26 % of OpenAI, that's$130 billion. This nonprofit is going to sell some of that stock over time to pursue their nonprofit mission of ensuring that AI benefits all of humanity. Like committing 25 billion bucks to health breakthroughs and AI resilience. And finally, quick heads up, this week, Europe is one hour closer to us, at least time-wise. Not possible, Jack.
24:29Here's the deal. You see, they do daylight savings just like we do. They're not like Arizona, but they do it on a different schedule. Yeah. So Europe changed their clocks last weekend. We're going to do it this weekend, but right now we got this funky little week where we're really close to each other. So New York to Paris is usually six hours. This week, it's only five hours. Now time for the best fact yet. This one sent in from Jason Geiger about the story we did the other week on the 150 person limit on the number of friends you can have. Push and play. Guy from Buffalo with the best fact yet.
25:03Many of us just learned that we are limited to 150 real friends. This is what's called the Dunbar number and has a big effect on more than just your BFFs. Many companies limit working groups and even entire factories to 150 or less to keep the org structure clean, communication efficient, and prevent bureaucracy. In fact, the only group successfully known to exceed their Dunbar number is a T-boy podcast with a number of besties and yeties. Josh Allen rules. The Dunbar number. Yeah, there we go. It's official. It's a real thing. Yeties, you look fantastic out there. Jack, you look fantastic, but I am most excited that we already chose our Halloween costume, our business-themed Halloween costume.
25:45I literally Instacarted a Spirit Halloween wig today. That's the only hint I'll give you. If you're not trying on wigs today, then I don't know what you're doing. Yetis, you look fantastic. Jack and I, I'll see you in my night.
26:01And before we go, congratulations to new human Grady Krupka and his parents, Madison and John, in Costa Mesa, California, with the best baby yet. Future PGA superstar right here. And Marjace Miles II is also a new human. and listening to his first pod ever as a Dearborn Michigan baby. Dude, I went to business school with this guy. Jace, congratulations. Congrats, buddy. We can pump for you guys. And Juan Barrows down in Delaware County, Pennsylvania. Happy birthday, Juan. And happy birthday to Jamie Bailey in Portland, Oregon. And Tommy and Sonali down in Austin, Texas, the best sales leader and seller duo with the same birthday.
26:38Boom. Jack, if you know, you know. And happy 11th birthday to Christina Ibarra. in Minneapolis, Minnesota. And to anyone else celebrating something today, make it a T-boy. Celebrate the wins.
26:55This is Jack. I own stock of Instacart, and we both own stock in Airbnb, Apple, Peloton, and ETFs of the S &P 500 and some Bitcoin. Bitcoin named that. Bureau Premium Non-Alcoholic Beer. All right, yeah, he's 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 Biro, the premium non-alcoholic beer brand co-founded by Tom Holland.
27:31Yeah, 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 wins with all the taste of a premium lager or IPA, but none of the alcohol, there's no better choice than Bureau. 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.
28:02Trust us, we've done it. Only beer we know that actually upgrades the scene like a promotion. So, Bastis, if there's a win you're celebrating every day, Bureau is the non-alcoholic brew brand you got to bring. So use code T-Boy for 20 % off your first order at BureauBrewing.com.
Airbnb is using AI to block parties this Halloween… It’s their new Party Pooper with a Purpose.
Wikipedia visits are falling for the 1st time… and Elon Musk launched “Grokipedia”.
Amazon is laying off 14K, UPS just laid off 48K… We’ll tell you how to prep for the Great Hiring Freeze.
Plus, October 28th is the #1 stock market day of the year… and maybe in history.
Yeti Slack Group: https://join.slack.com/t/tboypod/shared_invite/zt-3gzqbodes-Rsna_S3cjjjKP5LvC3jYQw
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