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A travel agent, a matchmaker and a critic enters a bar...
A travel agent, a matchmaker and a critic enters a bar... This week, three stories about what comes next when we finally admit that searching is not the same as finding.
Forty years ago, you walked into a travel agency, told someone what you had in mind, and they came back a few days later with a trip. Today, if you try to book a trip to New York, Booking.com shows you 449 hotels, somewhere past hotel 100, there’s a “load more” button. I’ll bet my yearly salary nobody has ever clicked it.
When travel moved online, inventory scale took over curation, from three hotels you could now see fifty, which became hundreds, then thousands, and at some point the search results page became the only interface that worked. Even if not totally happy with it, Brian Chesky believes it is our best option for now, saying “AI chatbots are not the right interface for travel.” Ben Hylak, a former Apple designer, tweeted back: “I can very clearly imagine how to build this.” Given Airbnb’s recent product flop, I’d side with Hylak.
Where AI wins is curation: you only see options that match what you actually want, not everything that technically fits the dates. The fair objection is the visual layer, at some point you need to see photos, check a map, compare options side by side. But tools like Claude and Perplexity already generate that inline, in the same conversation. You don’t have to choose between chatting and browsing.
Twenty years of travel tech innovation, just to realize the answer was there all along: we just needed to ask questions.
Dating apps and OTAs have more in common than they’d like to admit. Both give you a catalogue and call it discovery. You flip through pictures, choose based on vibe, pray for the product to look like the photos, and hope there are no bed bugs. The swipe is a search result page with better UX, but the volume problem remain the same underneath.
Whitney Wolfe Herd, Bumble’s CEO, announced this week that the swipe is out. In its place: Bee, an AI agent that learns your values, preferences, and relationship goals, then suggests matches and explains why it picked them.
Airbnb’s founder meanwhile, spent much of 2025 talking publicly about his loneliness. Maybe he should sign up to Bumble. And if Bee can’t find him a match, at least he could steal the UI.
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The New York Times released its list of NY 100 best restaurants and the internet spent the next 48 hours explaining why it was wrong. Either the list is genuinely broken, or the NYT team planned the uproar and delivered a masterclass in digital marketing. Honestly, both are possible.
The takes I read all converged on the same three problems: the list reflects one critic’s palate, not yours; it’s technically impossible to review every restaurant in a city, let alone the three visits that food critics consider the minimum; and there’s no rational grid for putting a taco spot in Greenpoint on the same list as a French Michelin-starred bistro on Upper East Side.
I agree with all three problems, especially the first one. A list like this is great for filling your bookmark app with new ideas — but nobody has ever responded to “Do you have a good Italian place for tonight?” with “Let me open the NYT 100 restaurant list.”
Nobody has cracked discovery yet, not search pages, not ranked lists, not AI agents. The field is wide open and I’m here for it.