(Preview) Airbnb and Its Varied Ambitions, The High Agency Golden Era, HBO Max and the End of an Error

Reactions to a revamped app and the expanded ambitions of Airbnb, an excellent email about practical considerations for leaders if AI accelerates a bifurcation of society, and thoughts on HBO's rebrand and ESPN's new streaming app.

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Andrew Sharp?

  Hello and welcome to a free preview of Sharp Tech.

• 0:08Andrew Sharp?

  Hello and welcome back to another episode of Sharp Tech. I'm Andrew Sharp and sitting across from me, Ben Thompson, live and in person. How you doing?

• 0:19Ben Thompson?

  Good. I mean, we've recorded together a lot in the past. I never fully appreciated the extent to which you have podcast voice. We're just sitting here talking normally. Podcast starts like a whole different person.

• 0:31Andrew Sharp?

  I feel very judged because you were judging me for the podcast voice. You said you could just talk in a normal voice. Also, mere minutes ago, you were judging my DVR hygiene. So all the joys of having Ben in my basement here.

• 0:46Ben Thompson?

  I mean, I never, it's great. I just feel like I get a real big brother, little brother dynamic. I have to come and fix all your problems. It's amazing.

• 0:53Andrew Sharp?

  I can't wait to kick you out of my house. It's gonna feel great later this afternoon. But here we are and we have news that we will begin with today. After more than a year of teasing expansion plans beyond home rentals, Airbnb launched an overhauled app that's not just for homeowners and travelers, but also for personal chefs, hairstylists, trainers, and tour operators to offer their services widely. Airbnb has vetted providers to offer 10 categories of in-home services, including personally cooked meals, prepared food items, full-service catering, photography, spa treatments, massages, personal training, hair, makeup, and nail appointments.

• 1:38Andrew Sharp?

  The services can be reserved anytime without a vacation booked, and many of them include, quote, "an entry offering below $50," Airbnb said. The new experiences business touts a trimmed-down list of nearly 20,000 tours and cooking classes curated for quality and uniqueness with an average cost of $66. So Ben, you wrote about this on Wednesday, and I'm going to read an email from Joseph that's building on what you wrote. Joseph writes, "Ben and Andrew, the new Airbnb updates make me think Brian Chesky is experiencing a bad case of 'Canadian Devil Syndrome,' a term I completely made up."

• 2:22Andrew Sharp?

  Let me explain. A few seasons ago, South Park had an episode where in-show celebrities, Terrence and Philip, were pitched making a branded free-to-play mobile game. The executive pitching them explains that you give the game away, and interested players can spend a couple of bucks here and there for a little boost. Good harmless fun, right? Well, as the episode goes on, the executive reveals the deliberately manipulative game loops and Skinner box mechanics that they use to addict players and extract massive profits from so-called whales. Also, this executive is revealed to be the Canadian Devil as the executive unfolds.

• 3:01Ben Thompson?

  Is this a fiction document, or is it a documentary of the App Store?

• 3:05Andrew Sharp?

  It does. There are echoes of all sorts of different tech products here. "Canadian Devil Syndrome, then, is the cognitive dissonance within a company between their professed mission and how the business actually makes money. This exists in all organizations to varying degrees. Meta might say they're connecting the world, and they probably even mean it most of the time, but they make money selling ads. Similarly, Brian Chesky really wants to believe he's building a platform to facilitate real-world connections, but the reality is they've built a short-term rental marketplace. The big question for Airbnb's future: Does Brian Chesky really think Airbnb is an

• 3:50Andrew Sharp?

  experiences platform, or does he just wish it was? So, there you go. A related question is, have you ever watched South Park?

• 3:59Ben Thompson?

  I've seen an episode or two. I'm setting myself up for these blow-by takes.

• 4:05Andrew Sharp?

  That's right. In person, anything goes.

• 4:08Ben Thompson?

  So, it's interesting. He kind of jumped to the end in the conclusion, which is like my part three, raising these questions of Brian Chesky wanting to model himself, you know, after Steve Jobs and Walt Disney, all of whom...

• 4:25Ben Thompson?

  Like obsession with detail and the experience directly manifested in the product people bought or the experience they had.

• 4:33Andrew Sharp?

  Mm hmm.

• 4:33Ben Thompson?

  And one of the just the fundamental challenge is that's not what Airbnb does. Brian Chesky is not actually preparing the homes that people experience. He's not actually coaching the private chef. And like even right off the bat with these experiences and and the services, they have like the Airbnb seal of quality and this beautiful like like simulated like wax seal that they that they put on there. The iconic iconic iconography. It's all beautiful. It all looks great. Like in these profiles, I thought were really interesting. Kind of like old school Silicon Valley profiles where it's delivering what the PR subject wants, but also with a little wink wink from the author.

• 5:18Andrew Sharp?

  Don't worry, we're gonna get to the wired profile.

• 5:20Ben Thompson?

  Okay, great.

• 5:21Andrew Sharp?

  It made my week.

• 5:23Ben Thompson?

  It was really good.

• 5:23Andrew Sharp?

  Well, and also just a note on Brian Chesky and lack of self-awareness. In terms of his presentation in LA this week, did he intentionally ape the Steve Jobs style as he was standing up there in all black?

• 5:39Ben Thompson?

  Oh, I'm sure. I think one of the was it not the did you read the there's also a Wall Street Journal profile.

• 5:43Andrew Sharp?

  I didn't see the journal one.

• 5:44Ben Thompson?

  Okay, I think you must not have because you would have definitely noticed that there was a section on him choosing what shirt to wear.

• 5:51Andrew Sharp?

  Perfect.

• 5:52Ben Thompson?

  And like, you know, what sheen of black, what should, you know, all the it was definitely gonna be black. Yes, of course, of course he was. You know, I don't think that there's any question about it. And what you get in these profiles, and I think it speaks to sort of Joseph's point, is this is an executive that wants to exert control and has a high sense of design. And he's a designer. He went to RISD and you know, that that's what he does. And I'm all for a well-designed app. Airbnb has always been a well-designed app. Yeah. And that's not a detriment, to be clear. It's good to have a well-designed app.

• 6:30Ben Thompson?

  The fundamental disconnect is that Brian Chesky has no control over the actual experience of Airbnb. Because what he's running is actually a marketplace. And so you have this thing, just to jump, go back to the services angle and the experiences angle, they're going to apply the Airbnb seal of quality. Applying the Airbnb seal of quality is fundamentally incompatible with delivering a successful services and experiences business. Why? Because you need volume. You need volume on both sides. You need a volume of services and experiences. And more importantly, you need a volume of users. And that's the marketplaces are so powerful.

• 7:15Ben Thompson?

  And they're similar to platforms in a way. They're a platform of another sort. Where you're facilitating this connection between suppliers and buyers. And to do that, you need volume and you need liquidity, like just stuff being available and people going through. And to do that, you can't go in and individually like Vet each seller, yeah. And so there's this, just this sort of weird disconnect, it feels like, between the control he wants to exert and what the fulfillment he seems to get from.

• 7:58Ben Thompson?

  And again, you see it, this is not to diminish the app. The app looks amazing. The icons are awesome. Like, all this stuff is true. It was clearly slayed over. I'm not diminishing that at all. It's also relatively immaterial to the success or not of Airbnb's business. Yeah. Which is, how much supply do you have on? How many, how much demand do you have to? How successful are you at matching that? And maintaining and accelerating those marketplace dynamics. And so just by and large, even before we get into the critiques I have. Or skepticism I have about experience and services. That overall disconnect is what was really striking to me, what I think Joseph is sort of tapping into here.

• 8:40Andrew Sharp?

  Yeah, that's fair. And I think there was another disconnect where Brian Chesky was talking this week about the idealized version of Airbnb and how it's just people helping people and connecting people.

• 8:54Ben Thompson?

  By the way, do you say airbed or air mattress?

• 8:57Andrew Sharp?

  Uh, air mattress.

• 8:58Ben Thompson?

  Yeah, I say air mattress too. I'd never heard airbed, but I guess.

• 9:02Andrew Sharp?

  Did people come back at you and said, what's an, what's an air mattress?

• 9:06Ben Thompson?

  No, I typed airbed because that's what Chesky said, and I guess it is in the name. So I'm like, oh, maybe that's a coastal elite thing.

• 9:11Andrew Sharp?

  Yeah.

• 9:11Ben Thompson?

  So you're, you're my coastal elite expert.

• 9:14Andrew Sharp?

  Nope. Air mattress for me.

• 9:17Ben Thompson?

  No, yeah, it's like, yeah, we started out Airbnb, that's how we started the presentation. We added air mattress in our apartment, sorry, airbed in our apartment in San Francisco. And we made some money and, and became this sort of thing. And, and then we're, you know, we have video of it and us driving around San Francisco and it's so charming and great. And I'm like, that is all fantastic.

• 9:35Andrew Sharp?

  I really appreciated you interjecting in your update and saying, that is not really what the Airbnb experience is, is today. Or the Airbnb experience, because it's like a lockbox. It's very impersonal. And that's fine. I actually think the Airbnb rental experience can be unfairly maligned sometimes. Like anytime I see people talking about Airbnb online, they're ragging on it. And I, I think for a little while there, like eight or nine years ago, people were talking about Airbnb just displacing hotels entirely because it's just going to be preferable. I'm not there. Let me be very clear.

• 10:16Ben Thompson?

  I'm definitely not there. Yeah, I am, I'm a big hotel fan. Oh, not of the, not of the hotels I was at this week. I'll tell you that much. Uh, but no, but the, no, it's a, it's in, Airbnb is such a complicated company. I mean, because a point I used to make years and years ago, because you had the two companies that came out together, which is Airbnb and Uber. And I always thought it was very unfair that Airbnb was the darling and Uber was the villain.

• 10:43Andrew Sharp?

  All right, and that is the end of the free preview. If you'd like to hear more from Ben and I, there are links to subscribe in the show notes, or you can also go to sharptech.fm. Either option will get you access to a personalized feed that has all the shows we do every week, plus lots more great content from Strategery and the Strategery Plus bundle. Check it out, and if you've got feedback, please email us at [email protected].