Chesky says Sora could be the end of social media

In part 1 of our Brian Chesky dissection, I want to concentrate on his comments around social media.

Chesky was on stage this week at Reid Hoffman’s Masters of Scale Forum. The dialogue was considered so vital that the MoS team released it almost immediately as a podcast.

At one point in the chat, Brian suggested social media could be coming to end thanks to AI generated videos that had exploded from the launch of OpenAI’s Sora2. (Yes, I may have got caught up and created a video Beethoven crowd surfing at Nirvana concert - guilty).

Brian suggested if you can never work out what is real or not, then at some point you lose interest. He suggested “Mark” (Zuckerburg) will see what is happening at Sora and double down to try to win the AI entertainment war, killing off the golden goose of Instagram.

But Brian’s entire thesis here was that he is betting on reality. He is going to go after the anti-trend in a tsunami of the AI trend. He believes people will have a reaction towards real life connection, real life art, real life food.

And whilst he didn’t actually say it - I’m going to extend his thought process (which I largely agree with) and say people will also crave real life content. Stuff made by people who were really there and experienced it. People who can give a view (or review).

The platforms might change because they get swallowed in the AI sink-hole - but the people will move to places where they can get what they want. They always have. It seems like a pretty good time to be building a platform based around real travel content.

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Having a place to Belong is a good place to be in the AI world.

Part 2 of the Chesky dissection comes mainly from the summary of the chat by Masters of Scale on their own LinkedIn page.

For Brian, the answer lies in transforming the company into "a new form of entertainment" that brings travelers and locals to experience the real-world. And as AI-generated content becomes more convincing with the release of Sora 2 a couple weeks ago, he believes this "movement to real" will only grow more urgent.

"There has to be this movement to real," Brian said. "We’re really doubling down on real people, real world, real connection. We want to be an AI-native application to get you off your phone to the world that will be somewhat unadulterated by AI."

So in summary - AI native to escape AI. Got it! Go.

In the podcast itself the other words that rang out in my ears as Brian mentioned them over and over were community. Everyone is building a community these days. (PS: Join our Slack Community 😀 ). Airbnb went a long way down this path once before when they used to do live events and local host communities. Alas it was short-lived and instead natura communities of disaffected hosts emerged and did communities of haters in over-touristed destinations where rents became untenable.

They might be coming from a long way back on the community front. If I were them, I’d invest super heavily in the guide community. This could be the connective tissue to something special that helps people Belong Anywhere.

Guide Startup leverages MCP to get guides booked directly out of ChatGPT

This seems to be flowing nicely this week. 😅 

Couldn’t help but notice a post this week by an ambitious young startup that thinks it can be the source to get private guides booked directly from consumer queries on ChatGPT.

Theoretically, this is a great idea. (It isn’t built yet).

Practically however, rounding up guides directly and getting them to keep their availability straight has always been a challenge. But maybe this is less of an issue in the agentic world?

If you can get the WhatsApp numbers of the guides and have an agent just WhatsApp them to ask about their availability as part of the flow - and all they need to do is check their own calendar and WhatsApp back (all this happens out of sight of the actual consumer) then why not?

Who needs live data and synced calendars when you can just ask.

Note: I have no idea if this is the approach they are taking or not. I’ll try and get them on the podcast.

One woman startup raises $2M to provide training data to book flights (among other things)

An awesome story this week about 22-year-old Alisa Wu who has just raised a cool $2M pre-seed with no co-founder and no product.

Wu, who is from Australia, has had a great run in her young life “having already launched a series of startups, including Stella AI, which was acquired in 2024. She was also a founding engineer in the ad platform, MagicBrief, later acquired by Canva.”

At 22 I think I was living under the stairs at a friend’s place (not in a cool Harry Potter way) and picking up empty glasses in a nightclub. I guess it takes all types.

The business is called Lucent.

“Lucent will utilise browser interaction data to address a gap in training data, thereby supporting models such as OpenAI and Anthropic. It’s believed this training data can support AI agents to be better equipped to tackle taskings like filling in forms, booking flights and completing online purchases.”

I believe Wu is hiring so won’t be staying a company of 1.

The investors here which broke all usual startup tropes include Horizon, Browder Capital, Long Journey, Weekend Fund and Firestreak Ventures. Well done to them.

Swifty gets acquired by Revolut

Keeping the startup theme going, it was amazing news overnight to hear that my friend Stanislav Bondarenko’s startup Swifty had been acquired by Revolut.

Stan and I tried to record a podcast a while back about the business but we were blighted by internet failures and other bugs. I should see if I can piece what we’ve got together in light of this incredible outcome.

“Founded in 2023 and incubated at Lufthansa Innovation Hub, Swifty is an AI assistant that automates business travel handling planning, booking, payment, and invoicing allowing trips to be booked in just five minutes via chat.”

Christopher Guttridge, Head of Loyalty at Revolut, says: “This acquisition strengthens our position at the intersection of finance, AI and lifestyle. Through this move we’re gaining both talent and expertise in AI driven travel solutions, which will help us deliver even more personalised and seamless experiences to our customers.” as reported by startuprise.co.uk 

It is yet another move by Fintech to go deeper into travel. Whilst we don’t have the concept of the superapp in the same way as the East - these Fintech’s are creeping their way towards the same outcome.

“Stanislav Bondarenko and Tomasz Przedmojski, Co-founders of Swifty commented: “We’re excited to bring the power of Swifty to tens of millions of Revolut users. Joining forces with one of the world’s leading FinTechs is a once-in-a-lifetime opportunity to scale our vision globally and enhance the lifestyle of over 65 million customers. Together, we’ll build an AI concierge that not only simplifies travel but anticipates everyday needs across all aspects of life.“

Go Stan & Tomasz!!

Call to arms for hotels around the new AI paradigm

Friend of the podcast, Michael Goldrich this week laid out a 5-step plan for hotels to get their AI future in order:

FIVE ACTION STEPS FOR HOTEL COMMERCIAL TEAMS:

1️⃣ Stop Outsourcing AI to Your Vendors If your in-house team can’t articulate how ChatGPT impacts discovery and conversion, that’s a leadership failure.

2️⃣ Embed AI Into the Direct Booking Strategy AI voice agents, image generation, conversational UX. These aren’t tools. They’re your new infrastructure.

3️⃣ Audit Your Visibility in AI Interfaces Ask ChatGPT to recommend a hotel in your local area. If your name doesn’t show up, fix it. Immediately.

4️⃣ Rebuild Your Tech Stack Around Interoperability Fragmented systems can't compete in an integrated, AI-driven ecosystem. Think unification. Think velocity.

5️⃣ Train for Mindset, Not Just Skills This is about thinking like a platform. Teams need to operate with product-level clarity and AI-native fluency.

If you think someone (or everyone) you know or work with could grow from being more informed on the topic of ai + travel (or could use the training above) then please forward this email to them and they can click the button below:

Marketplace Spotlight: Autoura

Not an official part of the marketplace but for all the effort Alex Bainbridge puts into the Slack group - I will look to rectify that.

Alex’s business Autoura took out a huge prize this week winning a not insubstantial 10K in Euros.

“Over the past few months, we joined forces with Bespoke England Tours , and together we won the Fever Future Tech Prize, taking home first prize of €10,000”

Alex Bainbridge sat down with David Garcia to talk about how we’re running high-end private, vehicle-based experiences powered by AI hosts — including Dr Claire Hart at Stonehenge, now available in 17 languages. We also explored the evolving role of drivers and driver-guides, and what this means for the future of travel as AI glasses and new forms of interaction emerge. And for the AI sceptics — yes, there’s plenty of discussion about human connection in an AI-driven world. Listen to the 17 minute podcast on Youtube: https://lnkd.in/ehrU7UGN

If you have a B2B business underpinned by AI and looking for people to notice you, you can sign up to the marketplace for peanuts (top right corner, 5 mins, bring your logo).

I’ve priced for bootstrapped startups but also accepting larger companies too.

Booking Engines must die

Simone Puorto this week laid out why booking engines are just getting in the way of our eventual evolution.

First Simone explained the reality now in other parts of the ecommerce world: “When a user asks, for instance, “Find me a minimalist Italian vegan leather bag under $200,” the system identifies relevant products and, with a single confirmation, processes the purchase, payment, and delivery without opening a single new tab. Stripe secures the payment tokens, Shopify and Etsy provide inventory access, and ChatGPT orchestrates the entire flow, acting as a trusted agent rather than a middleman.”

(On a personal note, if the LLM did not find the bag made by Elina Lisman, partner of Slack group member Benoit Collin, then I’d say it is totally broken and worthless).

But I digress. Puorto goes on to tell us that in hospitality: “The problem is the very architecture of hospitality e-commerce friction itself. Booking engines, as we know them, are not just outdated tools; they are barriers. A shared, interoperable ARI layer, accessible by conversational agents through open protocols like the Agentic Commerce standard, could finally liberate our industry from one of its most archaic constraints.”

Slack Group!

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Most clicked last week was the link to Alex’s round up of our pre-AI forum chat. Alex is on fire this week.

That’s it - you’ve made it to the end of this edition. I’ll be putting the result of the most clicked post in next week’s edition so you can see where others are focusing. If I’ve missed something, you’ve got a tip or any feedback at all - you can simply reply to this email and it will come straight to me. I’m doing this for You so please don’t be shy to tell me what you think