Special thanks to Alpic for sponsoring this edition of the newsletter:

AI assistants are the new search bar for travelers. If your inventory isn't there, you're invisible. Alpic puts travel brands inside ChatGPT and Claude, with live inventory and real prices, bookable in the chat. We built it for Awaze and kiwi.com. We can build it for you. Catch us at Phocuswright Europe, Barcelona, June 16-17, or meet with our team online.

Story over solution

Barcelona’s intended 2028 ban on all short-term rental licenses is popular but the data is more complicated. No city that has implemented a full STR ban has demonstrated measurable housing relief. Berlin reversed its ban after two years. New York’s rents rose after Local Law 18 eliminated 90% of Airbnb listings. Hotel rates went up 12.6%. The housing crisis continued.

I built this analysis using Claude, combining research, data, charts, and design into a single published piece. It argues that Barcelona has chosen a story over a solution, and that the main beneficiaries are the hotel chains that lobbied for the ban. The process was as interesting as the output: research, writing, visual design, and publishing from a single workflow. Worth reading, and worth thinking about what that kind of AI-assisted work makes possible.

Your average customer, according to the Internet

JoseLuis Vilar (cofounder of Caravelo) asked ChatGPT to draw a caricature of the average customer of Europe’s top four low-cost carriers. The result is the internet's collective memory of a brand, averaged into a single image. Reviews, Reddit threads, TikToks, news articles, all compressed into one frame.

I asked JoseLuis to run the same exercise for the major OTAs. What the internet thinks your customer looks like is your brand, whether you built it that way or not. This accidental portrait may be more honest than anything your marketing team ever produced.

Fifty years of travel tips

Kevin Kelly has been traveling seriously for over 50 years. Take a look at his list of 50 Years of Travel Tips. Among them:

• If you hire a driver, or use a taxi, offer to pay the driver to take you to visit their mother.

• Your enjoyment of a trip will be inversely related to the weight of your luggage. Counterintuitively, the longer your trip, the less stuff you should haul.

• Don’t avoid tourist traps. They are world-famous for a reason: they usually have something special that keeps people returning. The trick is to visit them off-season, early morning, late at night, on foot, with a local, through the backdoor, off the main street, away from the vendors.

The paradox at the heart of AI

Dan Shipper has automated everything he can at Every. And yet his team keeps growing, with more human work than before. The better the models get, the more work there is to do.

In After Automation, he explains that AI progress creates more work for humans, not less, because AI is trained on the visible output of past work. Code, prose, support tickets, product specs, etc. It packages all of it cheaply. The problem is that once everyone has access to the same cheap output, the output stops being worth much. What becomes valuable is the judgment underneath it.

He calls this the frame/framer gap. Someone still has to decide which problem matters, why now, for this customer, in this market.

For travel operators, that judgment came from years of watching things go wrong in ways no one predicted. Pricing models that broke in specific edge cases. Booking flows that worked fine until they didn’t. Customer behavior that made no sense until it did. None of that is in a training corpus. It’s too specific, too lived, and too recent. That’s exactly why it holds its value while everything else gets cheaper.

The hindsight dilemma

“Quitting is not the problem. Quitting too soon is.” — Nir Eyal

“Three things you need: the ability to not give up something till it works, the ability to give up something that does not work, and the trust in other people to help you distinguish between the two.” — Kevin Kelly

There is no reliable way to know in the moment. The line between foolish and genius is only visible in hindsight. What you can do is improve your odds. Talk to more customers than feels necessary. Decide in advance what signals would make you change course, and write them down. And find two or three people who know your space, have no stake in your outcome, and won’t just tell you what you want to hear.

The personalization paradox

Travelers want brands to know them, but they don’t want to be known. A CapTech survey of 447 US consumers found that people are 40% more likely to buy from brands that tailor experiences to their needs. At the same time, 52% are reluctant to share the data that enables personalization, and two in three don’t understand how their data is used by AI. The gap between wanting personalization and trusting the systems behind it is wide.

This matters more in travel. Hotels, airlines, and OTAs hold some of the most intimate consumer data that exists: where we go, who we travel with, how much we spend, how often we cancel. The potential for genuinely useful personalization is real, but so is the possibility of getting it wrong.

Brands that resolve this will make the value exchange visible by clearly telling travelers what data is being used, why, and what they get in return. But most travel brands aren’t close. Hotels, for instance, still struggle with basics like remembering a returning guest’s room preference or not asking for information they already have. The paradox is real, but for most of the industry it’s still a future problem.

The moment of intent

Artem Simenenko, Director at Expedia Group, writes that ChatGPT is running ads in 1-2% of prompts, and most conversations that do have just one. According to data from Adthena, travel-related questions triggered ads across more advertisers than clothing or consumer electronics, with Expedia, Airbnb, Hilton, and Royal Caribbean already showing up.

Travel fits the format well. Booking a trip is a messy, multi-step decision involving destinations, dates, budgets, room types, cancellation rules, etc. A chat interface sees all of that happening in one conversation, which means an ad can appear at exactly the moment a traveler is narrowing down their options. Search can't do that. Read +

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Special thanks to Propellic for sponsoring this edition of the newsletter:

Did you know “shoulder” booking season delivers 2× the return on ad spend (ROAS) of peak booking season for travel brands? While most marketers cut spend when bookings slow, the top 25% scale up. Propellic analyzed $50M+ in paid media across 60+ travel brands to show what works. We’re reviewing the report on May 21st. → Learn More

1. Optimism gets you into the game, but pessimism keeps you there

Lori Timony, Christian Watts, and Bruce Rosard were kind enough to invite me to their Experience This! podcast The conversation started from my recent newsletter issue The Optimist’s Edge.

The central argument is that optimism is a timing advantage. Optimists act before something feels obvious but after it’s directionally true. They invest before the data looks good and that’s their edge.

But optimism applied in the wrong place kills companies. Patrick Collison of Stripe put it well: be macro optimist and micro pessimist. Optimistic about the long-term direction, pessimistic and ruthless about execution. Founders who burn through their runway are usually optimistic about both. The ones who never build are pessimistic about both. The only combination that works is macro optimism + micro pessimism.

In tours and activities this matters more than in other travel segments. Flights are logistics, but experiences are products built on belief and emotion. If you are not a macro optimist and don’t believe humans have an intrinsic need to travel and explore, there’s no reason to build in this space. If you do, the case for macro optimism is obvious. And from a customer perspective, if they are not feeling optimistic, demand disappears faster, but when optimism returns, this category grows faster than anything else. That emotional need is also what makes this category resilient to AI disruption. If AI continues to automate digital execution, the most valuable companies in travel may be those that make us use screens less. Being physically present is the whole point.

2. The end of Google Search (again)

'Is this the end of Google search?' has been a recurring headline. They’re snapshots of how analysts and the media feel about the present, but they’re still just ruminations and have a poor track record as guides to the future. Pieces like these are useful for entertainment and context, but they’re not something founders should lean on too heavily when making long‑term bets.

• The Economist: Is Google’s 20-year dominance of search in peril? (Feb 2023) - “Is Google’s 20‑year dominance of search in peril? ChatGPT‑like tools could disrupt a lucrative business.”

• Gartner: Search Engine Volume Will Drop 25% by 2026, Due to AI Chatbots and Other Virtual Agents (Feb 2024) - “By 2026, traditional search engine volume will drop 25%, with search marketing losing market share to AI chatbots and other virtual agents.”

• Skift Megatrends 2025: Google’s Search Dominance Will Face New Threats (Dec 2024) - “Google would face headwinds to its search volumes, which could be supplanted by SearchGPT, voice search and other competitors. Less traffic, fewer benefits to advertisers.”

• New York Times: Is Google Search Cooked? (March 2025) - “Google’s new A.I. Mode may signal the decline of traditional Googling as we know it.”

How it’s going for Google (Q1 2026)…

→ Google Search ad revenue up 19% year‑on‑year to $60.4 billion
→ Total revenue up 22% year‑on‑year, powered largely by Search and YouTube ads
→ Search queries hit an “all‑time high” with AI features driving more usage of Google Search.
→ Google continues to hold around 90% of the global search market share and processes trillions of searches annually.
→ Stock up 330% since The Economist predicted the end of Google’s lucrative business.

It turns out that incumbents like Google rarely stay frozen like a deer in the headlights when disruption arrives.

3. The founder’s edge

Across multiple cycles, the “founder effect” shows up in hard numbers. Bain’s data finds that since 2015, founder‑led companies have delivered 2.1× the total shareholder returns of their non‑founder peers, rising to 2.6× in tech companies. Data from early 2026 indicates that companies where the founder recently departed averaged 6.9% annual returns over five years, compared to 15.4% for those still led by founders.

Most CEOs are trained to manage risk but founders act as chief risk officers. They are optimistic about where the world is going and ruthless about execution. The gap widens in eras of disruption. Google is the clearest recent example. After years of being perceived as behind in AI, co-founder Sergey Brin returned to the technical trenches in 2023. The culture shifted, the results followed, and Google’s stock has grown 210% since.

A founder's job is to inject risk into the business. It's flooding it with new ideas, stuff that seems hard to do, ideas that no one else would dare try, placing the kinds of bets that only someone who started the damn thing would be willing to wager. - Jason Fried, Founder & CEO at 37signals (makers of Basecamp and HEY).

4. "Nobody has figured out AI for travel yet."

Brian Chesky’s Q1 earnings call for Airbnb was full of concrete AI thinking.

On the internal side, 60% of Airbnb’s code is now written by AI, roughly twice the industry average. Chesky’s takeaway is that the company needs to restructure around speed. In his view, there’s no longer much of a role for hands-off managers running teams from a distance. Design managers and engineering managers are going back to writing code.

On the customer side, Airbnb deliberately started AI at the bottom of the funnel, in customer service, because Chesky considered it the hardest problem: no hallucinations allowed, multilingual, high-stakes, real-time decisions. Over 40% of support issues are now resolved without a human agent, up from a third last quarter. Cost per booking fell 10% year-on-year.

He made the case for why chatbots, as currently built, don’t work for travel or ecommerce. Four reasons: too much text in a category that is fundamentally photo-forward; no direct manipulation of filters or sliders; comparison at scale becomes impossible inside a thread; and most bookings involve multiple guests while chatbots are built for one person. His conclusion was that nobody has figured out AI for travel yet.

5. Query framing is now a distribution strategy

A new study audited 1,357 Gemini citations across 156 hotel queries in Tokyo. Query framing determines whether AI cites an OTA or a hotel’s own website.

“Cheap hotel in Shinjuku” returned OTA citations 69% of the time. “Hotel with local charm in Shinjuku” dropped that to 44%. A 25 percentage point swing from rephrasing the same question.

Content depth mattered more than brand or technical polish. Hotel K5 has strong ratings and proper schema markup. Gemini mentions it, but cites Expedia, not K5's own site. Kadoya Hotel has no schema markup or SEO, but its 33-question FAQ and 13-attraction neighborhood guide got Kadoya's own website cited directly.

The study is Tokyo-specific and Gemini-only, so treat the exact numbers as directional. But the underlying logic is that AI search cites whoever answers the question best. For price queries, that’s still OTAs. For everything else, hotels with deep content can compete.

(Thx to Gene Quinn for pointing me to this paper)

6. A headline that works against itself

The title of this recent eDreams press release: “eDreams ODIGEO further Scales Agentic AI Ecosystem by Integrating Conversational Planning and Immediate Booking Fulfillment.”

Buried in the jargon is an in-app trip planner, ChatGPT integration, and voice AI that now handles 90% of call traffic across five languages, with call transfers down 33%, resolution time down 15%, and the whole thing deployed in weeks. Not bad!

The title is the opposite of clickbait. It actively discourages people from reading results worth reading.

7. Follow the money

This table shows the 25 countries with the highest outbound tourism spending in 2024, ranked by growth since 2022.

China and the United States are essentially tied at $250 billion each. No other country is close. Germany and the UK are third and fourth at $120 billion and $119 billion respectively.

Seven of the top ten fastest-growing markets in this group are in Asia, and all seven more than doubled.

8. The $1.4 trillion demographic

Every travel brand wants to reach Gen Z, but the traveler spending the most is twice their age. Baby Boomers spend an average of $8,242 per trip, more than double what Gen Z spends ($3,753). The 50+ segment accounts for over $236 billion in annual US leisure travel spending. By 2030, the 60+ cohort will reach 1.4 billion people globally and will account for over a third of all international trips. The silver tourism market is on track to hit $1.4 trillion by 2032. This segment still books mostly on desktop, still uses travel agents, plans months out, and has an 8% AI adoption rate for travel planning (94% of those who tried it found it helpful). A demographic with money, time, and demonstrated openness to tools that work for them. There seems to be an opportunity to build products specifically for them.

9. Who the product isn't working for

Comparably breaks down NPS by age and the pattern is consistent across Booking.com, Expedia and Airbnb; satisfaction drops as travelers get older, with detractors dominating from the mid-40s onwards. Paired with the senior travel spending data above, the charts below show that the most valuable travelers in the market are also the least satisfied with the products available.

10. The loyalty gap

Caravelo benchmarked the loyalty programs of the five largest OTAs using a framework built around three pillars: Access (exclusive inventory and belonging), Control (pricing transparency and flexibility), and Convenience (booking ease and digital experience).

Across all five programs, Convenience is well covered and Control is getting better. Access (exclusive inventory, belonging, the kind of thing AI cannot replicate) is where every one of them falls short.

Airbnb has operated for fifteen years without a formal loyalty program. No tiers, no points, and no member pricing. A traveler who has booked 100 nights receives the same treatment as someone booking their first. On formal metrics, Caravelo scores it near zero on Access.

And yet Comparably’s NPS data tells a different story. Airbnb scores 24, Expedia 4, Booking.com -1. Brand-driven loyalty, with no formal program, is outperforming two of the most sophisticated points programs in travel.

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This issue is full of examples: a great hotel location that works against you, a bad photographer who might make the best campaign, and a philosopher who had Instagram figured out in the 17th Century.

Special thanks to Alpic for sponsoring this edition of the newsletter:

A new channel for holiday discovery is growing fast, and most travel brands aren't on it yet. Cottages.com, the UK's leading provider of vacation homes and luxury properties, partnered with Alpic to build an AI app featured on ChatGPT and other assistants: live inventory, real pricing, direct to booking. Read how they did it and what AI distribution could look like for you.

1. Blaise Pascal predicted the travel influencer

Pascal (French mathematician, physicist, and philosopher) wrote this 350 years before Instagram.

“We usually only want to know something so that we can talk about it; we would never travel by sea if it meant never talking about it, and for the sheer pleasure of seeing things we could never hope to describe to others.” — Blaise Pascal (1623 – 1662)

2. Hotels are becoming subscription businesses

And they are targeting locals. Hotels across the US are launching private membership clubs inside underused conference rooms, rooftop pools, and ballrooms. The Clayton in Denver charges $1,900 to $3,200 a year. Seven24 Collective in New York has 600+ members paying $2,150+. The Auric Room in Montana charges $6,500 / year, with 95% renewal rates.

A membership club generates recurring revenue, builds a local community, and gives guests somewhere to be that isn’t a generic hotel bar. There’s a financing angle, too, as developers who once sold condos to fund hotel construction now sell memberships too. The obvious risk is that if clubs scale too far, paying hotel guests may start to feel like second-class citizens. Read + WSJ (no paywall)

3. The carry-on era

"Your enjoyment of travel is inversely proportional to the size of your luggage." — Kevin Kelly

About 52% of passengers now prefer carry-on only and carry-on spinners account for roughly 60% of luggage purchases. Airlines created this shift themselves. US airlines collected $7.27B in baggage fees in 2024, and globally, the world’s largest airlines generated $33.3B in 2023 (CarTrawler/IdeaWorksCompany).

The behavior airlines incentivized is now an operational headache. Boarding times have roughly doubled since the 1970s, partly because overhead bins can’t absorb the volume. Airlines are responding by enforcing size rules more strictly and adding gate-check fees.

4. Hotel design is more of a differentiator than location

A study from Lucerne University of Applied Sciences and Arts, conducted across 14 Swiss hotels, measured multiple factors (functionality, individuality, emotionality, location, and employee behavior) to understand what drives impact and recommendations.

Hotels scored 64% on functionality, 58% on individuality, and 51% on emotionality. Operations are easier to get right than emotional engagement.

The study found a negative correlation between location and impact scores; hotels with less prime locations outperformed on guest impact. The likely explanation is that a great location can make hotels lazy. Hotels without that advantage have to earn the guest through experience.

Design Impact, as the study calls it, covers differentiation, coherence, and consistency throughout the stay. As design impact increased, recommendation rates rose. Negative comments about the look and feel on Booking.com reduced scores by an average of 1.11 points, more than any other factor tested.

On the employee side, autonomy correlated directly with guest experience quality. When staff could act on behalf of the guest without asking permission, guests felt it.

(Thanks to Bashar Wali for surfacing this report.)

5. Icelandics keep out-marketing everyone

Apparently, Iceland doesn’t need help looking good.

Icelandair is looking to hire a bad photographer; one with no photography skills, bad framing, and unfamiliar with composition. The selected candidate gets a 10-day trip to Iceland in June 2026, travel expenses covered, plus US$50,000 for photography, content, and participation. To all bad photographers out there, the deadline to apply is April 30.

This follows a string of clever campaigns from Iceland’s tourism ecosystem, including the Icelandverse parody of Zuckerberg’s metaverse pitch, a conspiracy film claiming Iceland was AI-generated, and a letter to travelers explaining how to enjoy real, unreal experiences.

Most destinations try hard. Iceland keeps proving they don’t have to.

6. Kind lies, unkind truths

William Meijer put a chart on something most founders learn the hard way.

In travel startups, many early conversations fall into the category of kind lies.

A large partner says they need to discuss it internally. A hotel chain says they love what you’re building. An investor says “not the right time, but keep us posted.” Each one feels like forward motion, but most are just reducing social friction.

The founders who last develop a tolerance for unkind truths. They ask harder questions, push for clear commitments, and learn that enthusiasm without commitment is usually a no. In practice, anything without a clear next step is a no.

7. ​​A better way to think about B2B positioning

April Dunford’s post is a strong guide to a problem many B2B teams still handle poorly: positioning, which is essentially about how a product should be understood, by whom, and against what.

She makes the point that most companies are wrong about whom they compete with. Internally, everyone has a different answer. Marketing looks at the loudest competitors, product looks at future ones, sales fixates on the last deal they lost and founders often anchor on an outdated picture. But the only view that matters is the buyer’s; what would they do if you didn’t exist? Often, the answer is the status quo. Spreadsheets, email, manual workflows, or doing nothing. If you ignore that, your positioning ends up fighting the wrong battle.

She also notes that features are not the same as value, and that value is not the same as handling objections. Many products try to do all at once and end up with messaging that is technically correct but hard for customers to care about.

8. Value creation in travel

A few of the ideas I shared in a recent interview with Shiji Group

• For years, I thought the winners would be the ones with the best technology. Technology matters, but understanding your customer matters more. Data tells you what is happening. Customers tell you why.

• Personalization is less about adding options and more about removing irrelevant ones. Less cognitive load, faster decisions, higher conversion.

• The industry is obsessed with frictionless experiences, but the right kind of friction builds trust. A callback at the right moment, or a confirmation step that prevents mistakes, can create more confidence than a perfectly smooth flow.

• For twenty years, whoever owned the interface owned the customer. AI is changing that. Discovery, comparison, and transaction no longer need to happen in the same place. The next battle is for the decision layer.

9. Founder CEOs: the loneliest job

“If the company’s doing poorly, you have to bring the positive energy and make people believe it’s possible. And if the company’s running hot, you want to bring them down to earth. Running counter-emotionally to what everybody else in the organization feels is exhausting.” — Bill Gurley (on My First Million Podcast [27:32])

10. How the Middle East conflict is hitting travel marketing

Propellic tracked sessions, search intent, and ad performance across 60+ travel brands to map the damage. Conversion rates have dropped across the Mediterranean. Southeast Asia, meanwhile, is showing peak performance while growing ad spend.

Their report, The Impact of the 2026 Middle East Conflict on Travel Marketing, examines why session data in frozen-zone destinations is misleading, which destination clusters are growing despite the crisis, and how to build retargeting audiences now so you convert at maximum ROAS when confidence returns.

Free live briefing on April 23rd (9:30 AM CT) with Propellic’s Brennen Bliss and John Matson. (Register here).

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1. Make something worth remarking

A message in a bottle thrown from a Canadian ferry just washed up in Scotland. It traveled 4350 km, survived two winters at sea, and was found intact on a beach by a dog. People are sharing it everywhere. The bottle has no utility. It just has an improbable story, and improbable stories are remarkable in the original sense: worth remarking about.

Psychologist Robert Plutchik defined delight as Joy + Surprise. The bottle delivers both. Travel products tend to get built around function. Ease of booking, speed of check-in, seamless payments. All of it matters, but almost none of it gets remarked about.

Pack Up + Go lets customers book a trip without knowing the destination. Days before departure, an envelope arrives: “You’re going to ______,” to be opened at the airport. People film it, photograph it, share it everywhere. No utility. Just an improbable moment landing exactly right. Most travel products optimize for certainty; Pack Up + Go introduces uncertainty at exactly the right moment, delivering both surprise and joy.

Like the bottle, it’s not the object that matters. It’s the story it tells.

If customers don’t have a reason to talk about you, growth has to come from somewhere else, and it’s usually expensive.

2. The brand test

Seth Godin draws a useful distinction. If Nike announced they were opening a hotel, you’d have a pretty good idea what it would feel like. If Hyatt announced they were making shoes, you’d have no idea whatsoever.

Casa Camper did exactly that. The Spanish shoe brand opened hotels in Barcelona and Berlin, and anyone who knew Camper could predict what they'd feel like: understated, design-led, and slightly unconventional.

Godin's answer to what builds a brand: a sustained point of view, the confidence to make an assertion, and the discipline to deliver on it consistently. Through design, service, and product, not through logos or ad spend. That's a longer game than most companies are willing to play.

Try it with any travel company you know. If they announced a product in an adjacent space, would you have a clear sense of what it would be like? If not, they don’t really have a brand yet.

3. Small signals, big brands

Eli Strick, Head of Customer Experience at Wells Fargo, shared a simple CX framework from Marriott’s CCO: get the basics right → make it easy → connect emotionally. For the last one (connect emotionally), small gestures can make a big difference. Strick’s example is how a plate of matzah during Passover in a United Club lounge would have cost almost nothing. He’d probably skip it himself, but he would notice and would appreciate the thought behind it, and that’s the point.

Ideas like this are easy to come by. What’s rare is seeing them repeated day after day across hundreds of locations and in the small moments that matter to travelers. That’s where most brands lose consistency. The ones that get this right build something competitors can’t easily copy.

4. Trying too hard

The number one reason younger consumers reject brands is that brands try too hard to reach them. Generational targeting is mostly a distraction from the harder work: building something worth noticing. Most of the time, “trying too hard” shows up as marketing doing the work the product should be doing.

5. Brand in a sign

Danica Smith says it well: “If a sign makes me laugh, I already like the hotel more. Low cost. High impact. Pure personality.”

6. Brand in a bottle

Tim Peter spotted this in a hotel bathroom. Whether it reads as careless or committed to sustainability depends entirely on everything else the hotel has already made you feel by the time you reach the bathroom.

7. The guest in front of you is your customer

In 2019, I shared this quote by Dara Khosrowshahi (then CEO of Expedia and now CEO of Uber), speaking to hoteliers:

“You guys all criticize me for how much I charge you for guests to come to your hotel. I think you’re looking at it wrong. Look at us as the cheapest source of referrals that you could imagine. If they come through me, you pay me once, and if they come back to me again and again, shame on you. You should make them a loyal customer.”

The cartoon below, published by Savvy, makes the same point. The hotel has a chance to make them a direct customer for life, and they pass.

8. Your customers know

Most companies survey everyone and hear mostly noise. The signal is in your best customers; the ones who came back, referred someone, or chose you over a cheaper option. Ask them why. The answer is usually simpler than whatever your marketing team came up with.

9. The new brand battlefield

Headlines such as ‘Cracks Emerge in the OTA Oligopoly' reflect the prevailing view that AI spells trouble for OTAs. Meltwater just tracked which travel brands LLMs recommend most across prompts and models. Both Booking.com (55% visibility) and Expedia Group (54% visibility) dominated AI-generated recommendations for Europe in spring 2026, while Tripadvisor, Hotels.com, and Kayak lag far behind.

Meltwater has a product to sell (so treat the numbers as directional rather than definitive), but the signal is that even in an LLM-first world, the brands that won the last era of online travel are still dominating in today’s AI search. The question this data doesn't answer is what share of traffic and bookings is starting with an LLM today.

Also worth noting: a few European OTAs with meaningful market share in Europe don't appear in this list at all. For them, the conversation about LLM visibility is even more urgent.

10. Parkinson’s Law in the age of AI

Last issue I wrote about an HBR study showing AI intensified work rather than reducing it.

Parkinson’s Law explains why that was predictable. The law says work expands to fill the time available. It held up for 70 years because time was the constraint. AI removed that ceiling. The law hasn’t changed, but the constraint has. Work now expands to fill capacity, and expectations rise with it.

Time limits are obvious, but capacity limits have no natural ceiling, and neither do expectations. No one calls them out and the expansion just happens until it feels normal. That’s not necessarily bad but it is worth knowing it’s happening.

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1. After craft, what?

Pete Flint at NFX uses photography to explain the possible impact of AI. When the camera arrived in 1839, painters panicked. Painting didn’t die. It exploded into Impressionism, Cubism, photojournalism, amateur photography, street photography, instant prints, and each disruption added layers. The game got bigger.

The same pattern is forming now. Flint maps out a hierarchy worth internalizing. Execution is getting automated. Craft is getting commoditized. Even taste (knowing what has worked before) will eventually be a learnable signal for AI. What survives is expression: a genuine point of view on what could be.

He gives the example of Picasso. He mastered realism first, then discarded it for something nobody wanted, until it became one of the most important paintings in history. He was using “skill” as a floor, then pushing toward something only he could make. The founders who pull ahead will do the same: treat commoditized execution as table stakes, and compete on what only they can see. Read + NFX

2. The jobs that don't exist yet

The fear of AI taking jobs is real, but it’s also misdirected.

US census data shows roughly 60% of the jobs people do today didn’t exist in 1940 as distinct occupations. New technologies created whole new categories of work.

The numbers looking forward are just as striking. The World Economic Forum's Future of Jobs Report 2025 projects 170 million new roles created and 92 million displaced by 2030, a net gain of 78 million roles. They also estimate that around 65% of today’s primary school students will end up working in jobs that don’t yet exist.

What we call “fear of AI job loss” is mostly fear of current job loss, which is understandable. But the historical pattern is consistent: automation reshapes and expands work, retiring old roles while creating new ones at scale. AI looks like a continuation of that pattern; faster, but not different in kind.

The disruption is real, but the ending isn’t.

3. The panic and the pattern

Every new technology triggers a moral panic. Marc Andreessen traces it back to Socrates, who thought written language was a mistake. The bicycle got its own version in the 1880s, when the press warned that young women who rode them would develop “bicycle face,” a permanent grimace from exertion that would make them unmarriageable. Jazz was going to corrupt youth. And so was rock and roll, hip-hop, the internet…each one was going to ruin everything.

The technologies change, but the panic is identical. What repeats is the reaction to disruption, and that reaction drives clicks and headlines.

AI is no different. But what makes this moment harder to read is that even the people closest to a technology often misunderstand where it’s going. Edison invented the phonograph and was certain its primary use would be religious sermons, envisioning families gathered around the device at night listening to preachers. The world had other ideas: music. The inventor of the technology that would reshape global culture and spawn entire industries had completely misread where it was going. Even Wozniak (Apple co-founder) publicly doubted the usefulness of computers.

In 1839, when the daguerreotype (the first publicly adopted photographic process) debuted in Paris, most portrait painters concluded their craft was finished. Samuel Morse, himself a painter and inventor of the telegraph, saw it differently. In a speech to the National Academy of Design, he called it “undoubtedly destined to produce a great revolution in art” and urged artists to understand its influence rather than fear it.

Most saw the end and Morse saw the beginning.

The gap between the catastrophist and the early mover tends to be where opportunity lives.

4 We've been here before

When you see these types of headlines…

Remember that history rhymes.

5. Air travel didn’t escape the trend

In 1903, the New York Times predicted manned flight would take between 1 and 10 million years. 9 weeks later, the Wright Brothers flew at Kitty Hawk. Once flight was proven possible, critics called it a rich man’s toy.

When Kennedy announced the moonshot, opponents coined “moondoggle” (a wasteful government vanity project, in American slang). Even Eisenhower (who created NASA) called anyone spending $40 billion to reach the moon “nuts.” When the moon landing finally came, a teacher’s union organizer went to bed early, calling it “a trivial prestige exercise.”

The full arc of every transformative technology: impossible → wasteful → obvious

The Pessimist Archive has the receipts.

6. The acceleration trap

The historical pattern has been that transformative technologies expand, not contract, the world of work. The pessimists have been wrong in the long run. But the short run is more complicated. A new HBR study tracked AI adoption at a 200-person tech company over eight months. AI didn’t reduce work. It intensified it. Workers moved faster, took on broader scope, and voluntarily extended work into hours that used to be off. Many participants felt busier than before they used AI. The mechanism is that speed raises expectations → higher expectations increase AI reliance → more reliance widens scope → wider scope creates more work.

The arc of AI adoption may end well, but the path there has a burnout risk that most companies are not yet anticipating.

7. You see what you believe

Nir Eyal on the Modern Wisdom podcast talks about how your beliefs shape your interpretation of the world, and they also predetermine what you see in it.

Two groups were asked to count photos in a specially designed newspaper. Self-identified pessimists averaged 2.5 minutes. Self-identified optimists averaged 11 seconds. On page two, a caption read “there are 48 photos in this newspaper.” Optimists saw it and collected their prize. Pessimists counted the photos one by one, never seeing the answer staring them in the face.

The same mechanism runs in reverse. In the Dartmouth Scar Study, women had a realistic fake scar applied to their faces. Before entering a room, researchers secretly removed it without them knowing. They reported being stared at, discriminated against, and made uncomfortable…for a scar that no longer existed. They expected a response and found it everywhere.

Hans Rosling gave university professors an exam on the actual state of the world (education, health, democracy, female empowerment, etc…). They scored worse than monkeys. Their existing beliefs made the evidence invisible.

Successful entrepreneurs see opportunities that others walk past. Not because they are smarter, but because they expect to find them. If you are looking for $100 bills on the floor, you will find them. If you are looking for reasons it won’t work, you will find those too.

8. The end of the middleman

One way to train your eye toward opportunity is to choose your sources deliberately. For most of history, if you wanted to understand what a founder was building and why, you had to trust a journalist to translate it for you, with all their biases, deadlines, and narratives intact. That era is over.

“Every company is a media company now. You should be publishing your own content, direct to your own blog, social media... I really don’t like this idea of putting information out through a traditional journalist who’s going to bring their own bias and filter to it.” — Brian Armstrong, founder of Coinbase, on the David Senra podcast

We are living through a golden age of primary sources. Founders and entrepreneurs talk directly to millions. No filters, less spin, and no headline written before the reporting begins.

Read the books, listen to the builders and skip the intermediaries.

9. The screen fatigue dividend

Social media usage appears to have peaked around 2022 and has been declining since. Young people are leading the pullback; they grew up online, saw the full cycle, and concluded that endless scroll doesn’t make you happier or smarter. Greg Isenberg calls it the anti-trend: attention shifting back to things that feel real, slow, and intentional.

His list of where the opportunity lives includes slow media formats, private communities, paid memberships that deliver depth, and IRL anything…dinners, meetups, shared experiences.

The internet’s oldest assumption, that more engagement equals more value, is breaking. What replaces it are spaces that make people feel grounded, informed, and connected.

Note: The data is self-reported, so treat the direction rather than the precise numbers as the signal.

10. The farm is the story

Agritourism, an $8 billion market today, is one form of what Isenberg's anti-trend looks like in the travel industry. By 2033, it will reach $21 billion, growing at nearly 12% annually. Ben Wolff explains why. 99% of consumers want transparency in fresh food sourcing. Farm hotels skip the certifications and the supply chain documentation because guests walk into the field and see it themselves. Visual verification builds trust instantly, and trust justifies premium pricing in a way that a sustainability claim on a menu never could.

The properties leading this category have figured out what Wolff calls the “seed-to-soul” continuum. The farm dictates the menu, the spa treatments, the educational experiences. Blackberry Farm in Tennessee, Babylonstoren in South Africa, The Newt in Somerset. High-margin F&B from hyper-local ingredients, beekeeping workshops, on-site retail, large-format events.

The model is also bleeding into residential real estate. Agrihoods (master-planned communities built around working farms) are one of the fastest-growing ideas in residential development, with 200 already operating across 28 states in the US.

The common thread across all of it is transparency, wellness, community, connection to the land. Guests can feel the difference between treating this as core product or using it as a sustainability marketing claim.

PS. Adding a second brain for fundraising

I’ve added a new mode to the Travel Tech Essentialist Copilot: pitch-deck review. It’s the same thinking partner for product and growth, but now it can also pressure-test your fundraising story.

When you share a deck or have a fundraising question, it switches gears and reviews it through the frameworks of the most influential Silicon Valley VCs, flags common mistakes, scores the strength of the pitch, and suggests rewrites and structural improvements. But more importantly, it diagnoses what’s underneath: unclear positioning, weak traction, or a story that doesn’t hold together.

Go ahead, share your deck and ask it to rate it, identify what’s weak, and how to improve it.

Try the Copilot

Travel Tech Essentialist Job Board

New companies on the job board: Navan and Stay22.

• Navan is hiring across sales, revenue operations, strategy, product, and data roles in the US and Europe, with a strong focus on go-to-market and commercial teams. See all open roles here.

• Stay22 is building out its Montreal team across product, engineering, data, operations, and business roles. See all open roles here.

→ Explore all 2030 open roles on the Travel Tech Essentialist Job Board.

• Navan | Vice President, Solutions Consulting | New York City | $244k - $325k

• Airalo | Quality Assurance Engineer, Roaming | Europe; Africa; Middle East; Brazil

• The Hotels Network | Partnerships Manager | Fort Worth, TX; Dallas, TX | $81k - $100k

• Plug and Play | Venture Associate | Sunnyvale, CA

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And, as always, thanks for trusting me with your inbox.

Mauricio Prieto

1. A small ask

A small ask. The Travel Tech Essentialist Copilot has had 400+ conversations since I launched it a few weeks ago. I have no idea what they’re about. ChatGPT doesn’t give me that data.

So I’m asking directly. If you tried it, I’d love to know two things: what problem you were trying to solve and whether it actually helped. One sentence or ten, whatever feels right. Just hit reply.

I built it for travel founders and operators. The only way I know if it’s working is if you tell me.

2. The TAM slide that fools nobody

Pear VC’s Pepe Agell breaks down what early-stage investors want to see. A relevant point for travel founders is that bottom-up market sizing beats top-down every time.

Travel founders are especially guilty of the “$1.5T global travel bookings” slide. It signals to investors you haven’t thought carefully about your customer or your path to them. A bottom-up number, customers you can plausibly reach multiplied by what they’ll actually pay, tells investors you understand your business. The trillion-dollar figure tells them you read Statista.

His traction framework also changes by stage. Pre-seed, you’re validating the idea. Seed, you need a handful of people obsessed with your product. Founders often confuse “we have hotel partnerships” with product love. Those aren’t the same thing.

3. The invisible tax

I shared a version of this on LinkedIn last week and it resonated, so I’m expanding it here with something I left out.

When you work at Google, McKinsey, or Booking.com, doors open, emails get answered, and people take your calls. Most of the time, it’s the logo. A borrowed coat. Entrepreneurs don’t have that. Every door you open, you open yourself. Every email that gets answered, you earned. No tailwind, no borrowed credibility. That’s the invisible tax.

I co-founded eDreams in 1999, served as CMO and a board member, and remained with the company for 15 years through our IPO. We felt it from day one. In Barcelona, convincing local talent to join an unknown startup was harder than recruiting people from Australia, Israel, or the US. Airlines and travel providers barely answered our calls. Every meeting we got, we fought for.

The tax doesn’t disappear when you build something real. It reappears the moment you step outside your context. When I moved to the San Francisco Bay Area in 2015, nobody had heard of eDreams, a European company that didn’t register on the Valley’s radar. Same person, same track record, different country code.

So if you’re sitting inside one of those institutions right now, here’s a small ask: reply to that founder’s email. Take that meeting. Make that intro. It costs you almost nothing. For them, it might change everything. You also never know how quickly the roles flip.

And if you’re the founder paying the tax…it’s real, it’s not just you, and almost nobody talks about it. But it’s also temporary. You’re building your own coat, one relationship at a time. Eventually, it feels better than a borrowed coat ever did.

4. Sell the work

Many AI companies are building tools that make agents, revenue managers, and ops teams more productive. That’s the copilot model: AI in the hands of a professional, making them faster and sharper. The autopilot model is different. Instead of selling the tool, you sell the work. The customer buys the outcome directly.

Julien Bek from Sequoia argues that the companies that win in the long term will be autopilots. Read + Sequoia

Travel already has the conditions for autopilots to take hold. Insurance distribution, revenue management, customer service at scale…these are areas where a significant share of the underlying work is rules-based and already handled by outside providers.

Bek's key insight is to start where outsourcing already exists. If a task is already done externally, the budget line exists, the buyer expects an outside provider, and replacing a vendor is far easier than replacing headcount. For every dollar spent on software, six are spent on services. Autopilots go after the six.

The wedge in travel could be in TMC contracts, outsourced revenue management retainers, distribution agreements with brokers, etc… Each one has a budget line, an incumbent doing repetitive work, and a buyer already comfortable with an outside provider.

The long-term question for travel AI founders has shifted from “What tool can I build?” to “What work can I own?” That’s where the real opportunity sits.

5. Agents will eat your App, but they can’t eat your network

Slow Ventures’ Yoni Rechtman makes a distinction easy to miss. Aggregation is collecting options in one place. Useful, but it doesn’t trap anyone. Users can leave anytime, and an agent can replicate it overnight. Network effects are different. The more people use the product, the better it gets, and the harder it becomes to walk away from. As Yoni puts it: “Aggregation creates value. Network effects capture it.“ Read + Yoni Rechtman

Agent can scan flights, hotels, and experiences across the web in seconds. If your value is “we have everything in one place,” an agent can and will replicate that. What agents can’t replicate is a genuine network. A platform where hosts and guests build reputations, or a marketplace where reviews compound over time.

Many travel startups are building a list. A curated set of suppliers, experiences, or options. That was a defensible business when search and discovery was hard, but it’s a much weaker one when search is free and instant.

Take solo travel startups. Flash Pack, for instance, has leaned into the community layer: alumni groups, repeat travelers, a sense of belonging that outlasts the trip. Each returning traveler makes the product better for the next one. That’s a network. A startup that plans great trips for strangers, but where most people do one trip and move on, has a compelling brand and curation. But the value is in logistics and taste, not in a compounding community. One is agent-proof, the other is not yet.

Before your next product decision, ask whether adding one more user makes the product better for every other user. If the answer is no, you’re building aggregation. It’s not a death sentence, but you should know which game you’re playing.

6. Agents in the wild

Anthropic published a detailed study on how AI agents are being used in practice. Software engineering accounts for nearly 50% of all agentic activity. Travel ranks last at 0.8%. Read + Anthropic

That gap has less to do with how sophisticated travel operators are and more to do with what’s at stake when something goes wrong. Most agent activity today happens in domains where mistakes are assumed to be detectable and reversible, though even that assumption is being tested (Amazon recently had a nearly six-hour site disruption tied to AI-related issues). In travel, the consequences land harder. A bad booking propagates into real-world logistics…wrong hotel, missed transfer, ruined trip. The adoption curve will likely follow that risk gradient: research and price monitoring first, supervised booking next, and fully autonomous transactions once accountability structures are in place to support them.

It’s also worth questioning the 0.8% figure itself. Travel is less absent from the agent data than it appears. Software engineering includes the PMS, RMS, booking engine systems, back office automation, CRM, marketing tools that run this industry and that travel operators use daily. BCG reports that 37% of travelers already use AI embedded in online travel sites to plan and book trips, and AI-driven pricing has delivered upward of 15% RevPAR growth at some hotels. Travel’s AI activity is real. It’s just being counted in someone else’s column.

7. Selling to agents

One of the most important questions for founders is how to make sure agents know about their product/service and choose it? All the old tricks won’t work.

Brian Flynn makes the argument that AI agents don’t browse; they query. They have no brand loyalty, they are not driven by impulse and not subjected to the attention economy. They simply focus on: can you solve my problem, how fast, how much, how reliably? What matters for that is your API.

In one sweep across 44 agent services, only 2 had fully working endpoints. 53% of direct service calls succeeded. Flynn’s conclusion is that, in agent commerce reliability is the entire product. Read + Brian Flynn

For travel, this reframes the distribution question. The industry spent decades mastering human-facing distribution: search ads, metasearch rankings, OTA placement, landing page optimization. Machine buyers don’t respond to that. A hotel, airline, or activity provider that wants to be visible to AI agents needs machine-readable capabilities, protocol-based pricing, and provable reliability scores.

8. The Personalization shortcut

Hotels have spent years and enormous sums trying to crack personalization: loyalty programs, CRM platforms, tracking pixels, third-party data partnerships. Most still can’t do it effectively. The data flywheel that powers Amazon doesn’t have the same physics in hospitality. A loyal guest stays twice a year, and that’s not enough of a signal.

On this post, Gautam Lulla makes a sharp observation. A generative hotel website (one that responds dynamically to what each visitor asks rather than serving static pages waiting to be browsed), short-circuits the entire problem. The site assembles content around the guest’s specific question in real time. No behavioral profile required and no prior data needed. The guest’s intent replaces years of accumulated data.

The same content architecture that powers this also makes a hotel visible and accurately represented to AI agents, the next distribution surface.

9. Algorithmic relevance

BCG zooms out on the same problem. Brand equity in hospitality is shifting from name recognition to algorithmic relevance. In an AI-driven discovery environment, a hotel that can't be read and confidently recommended by an AI agent won't appear in the results at all. It’s not a problem of being ranked lower or being penalized or paying too high of a commission. The problem is being absent.

The mechanics matter. AI engines favor properties with comprehensive, high-trust, multisource content. Guest reviews, syndication across authoritative platforms, consistent digital presence: these become core commercial levers. Sparse or inconsistent footprints get filtered out.

The industry spent two decades figuring out their complex relationship with OTAs. This is the same battle, with higher stakes and less time to prepare. Read + BCG AI-First Hotels

10. Travel’s search dependency

Travel puts more of its ad budget into search than many other consumer categories.

The harder question is what happens in a world where AI agents make recommendations that ad spend doesn’t directly influence.

According to this BCG report, only 10% of travel executives outside the CMO role have prior marketing experience, compared to 40% in other consumer industries. BCG flags the stat without drawing the conclusion, but it’s hard not to. When the people approving the budget lack marketing instincts, long-term brand building loses to short-term performance marketing every time.

Travel Tech Essentialist Job Board

→ Explore all 2194 open roles on the Travel Tech Essentialist Job Board now.

• Stay22 | Head of Innovation Operations | Montreal, Canada

• WeRoad | Finance Automation & AI Specialist | Milan, Italy

• Acai Travel | Founding Marketing Lead | Barcelona, Spain | $60k - $100k

• Airbnb | Staff Data Scientist, Marketplace Optimization and Ranking | | Remote | $194k - $240k

📩 For monthly updates on the latest roles, subscribe to the Travel Tech Jobs newsletter

Raising a round?

If you are a startup looking to raise a round (from pre-seed to Series D), I can help (for free). Travel Investor Network is a private platform where I recommend innovative travel startups to investors and innovators. If you’re interested, please start by completing this form.

If you like Travel Tech Essentialist, please consider sharing it with your friends or colleagues. If you’re not yet subscribed, join us here:

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And, as always, thanks for trusting me with your inbox.

Mauricio Prieto

1. The Travel Tech Essentialist Copilot just got a lot smarter

Six weeks ago, I introduced an AI agent for travel founders, operators, and execs. But in the past two weeks, I rebuilt it from the ground up, and it's a much-improved tool.

The new Travel Tech Essentialist Copilot is an AI thinking partner for travel founders and operators that combines the best thinking on growth and product with deep travel industry knowledge.

It draws on three sources: six years of Travel Tech Essentialist newsletters covering the full arc of travel tech; every episode of Lenny's Podcast with conversations with 300+ of the world's best product and growth minds; and my hard-won lessons from building eDreams into Europe's largest OTA, plus years of advising, investing in, and mentoring travel companies since.

You can use it to diagnose a conversion problem, pressure-test your landing page, think through a marketplace strategy, or just ask a hard question about your business.

“Just tried this. “Dangerous” levels of useful. The way it reframes positioning questions is exactly what you want at 11 pm when you can’t sleep because of a strategic problem.” — JoseLuis Vilar, Co-founder of Caravelo

It’s free. Try it and let me know what you think.

2. Two rounds worth pausing on

I don’t usually dedicate space to funding announcements because money raised and value created are two different things, and I care more about the latter. I’ll highlight these two because I wrote a Deep Dive on each last year, so I’ve seen the work firsthand. Both have spent years building something real, and the capital finally caught up.

Stay22 raised $122M from Summit Partners. Five years ago they had 7 people and negative revenue. Today, they process over $1B in annual transactions and serve 5,500+ creators and publishers. They 20x’d revenue in five years while staying profitable. The round validates the core infrastructure they’ve been building quietly for the creator economy. → Deep Dive from April 17 2025

Wheel the World closed a $3.5M extension, bringing their Series A to $11M. They are solving both a moral and a structural problem. Accessibility information in travel is unreliable by default. Six years of verified data across 150+ destinations and 8,000+ services is how they’re fixing that. → Deep Dive from May 30 2025.

I only write Deep Dives when I’d put my own reputation behind the recommendation. Here is my Deep Dive philosophy, and what it takes for me to write about what you’re building.

3. The doorman fallacy

Imagine replacing a hotel doorman with an automatic door sensor. A consultant celebrates the cost savings, but no one accounts for what disappears: security, recognition for regulars, and a warm welcome. Someone gets credit for the savings and no one gets blamed for the experience getting worse.

Rory Sutherland, vice-chairman of Ogilvy, says the same pattern is playing out with AI. The easiest way to sell it to clients is as a cost reduction tool, so that’s how it gets deployed. He describes how companies push customers into their lowest-cost channels, with phone numbers disappearing and self-service becoming the default.

“A visitor to the site converts at about 0.5%. Anyone who phones converts at about 30%. Are we really sure this is intelligent?” — Rory Sutherland, in reference to a travel company

He thinks most businesses will use AI for “the same but cheaper.” A few will use it to add back human elements that never scaled before. Read + Sutherland

4. The “11-star” exercise

Rory Sutherland’s closing thought is the challenge: how do we use AI to add back human elements that never scaled before?

For one answer, look to Brian Chesky’s “11-star” design exercise. In Airbnb’s early days, Chesky mapped the guest experience from 5 stars to 11. At 5 stars, you knock, the host opens the door, you’re in, and it works. At 6 stars, there’s wine on the table and toiletries in the bathroom. At 7, your host knows you surf, and there’s a board waiting, lessons booked, and a restaurant reservation made. At 10, it’s The Beatles landing in 1964. At 11, Elon Musk meets you at the airport to take you to space. The point is not to reach 11. It is to find the sweet spot between “the door opened” and “I’m going to space.”

Historically, that sweet spot was a doorman problem. It didn’t scale because it required a human who knew you; that was expensive, manual, and one guest at a time. Personalization at scale was unrealistic. AI changes that constraint. It can infer preferences, anticipate needs, and act on them before the guest asks, enabling companies to move higher up the scale.

Companies will choose between automating away from people or toward them.

5. Thinking fast, slow, and artificial

AI can make travelers and operators smarter. It can also make them confidently wrong.

Daniel Kahneman, the Nobel-winning psychologist behind Thinking, Fast and Slow, gave us System 1 (fast, intuitive) and System 2 (slow, deliberate). A new Wharton paper proposes a third: System 3, the AI systems we increasingly outsource our thinking to.

The researchers tested what happens when people rely on AI to answer reasoning questions. When the AI was right, accuracy jumped 25 points. When it was wrong, accuracy fell 15 points below the no-AI baseline. People followed faulty AI recommendations four out of five times. Confidence went up either way.

They call this “cognitive surrender”; not just using AI as a tool, but abandoning critical evaluation entirely.

6. AI makes you better. It also makes you worse.

The Wharton finding got me thinking (it happens, sometimes). Cognitive surrender explains what happens, but it doesn’t explain why some people fall into it and others don’t. Two variables explain it.

• Restraint: how carefully you decide what deserves AI’s help. Low restraint means you outsource the thinking. High restraint means you do the thinking first.

• Leverage: how aggressively you use AI to increase your output. Low leverage means you barely use it. High leverage means you use it everywhere and always.

Think of leverage as the engine and restraint as the steering. Most people are upgrading the engine, but fewer are paying attention to the steering.

The dangerous quadrant isn’t the bottom row. It’s top-left. Noise Factories aren’t junior people producing mediocre work. They’re experienced operators who know what good looks like but stopped checking whether AI got there.

Pre-AI, carelessness was capped by effort. You could only move so fast, but now it scales.

The habit that separates Compounders is that they formulate the question clearly, with assumptions made explicit, before opening the prompt. AI accelerates a thought that already exists. It doesn’t replace one that doesn’t. That's the difference between System 3 working for you and working against you.

7. Booking’s February sell-off

Despite beating Q4 earnings and revenue expectations on February 18, Booking’s stock has dropped 17% this month, hitting a 52-week low of $3,870. The market’s reaction has less to do with the results and more to do with AI anxiety.

I heard a useful framework from Chamath Palihapitiya that can help explain this. In “when” mode, investors are confident the cash flows are real and durable; they’re just debating how long before they become less certain. That gets priced in gradually. But now the question has shifted to “if.” Investors are no longer confident that the cash flows are durable at all. Could agentic AI bypass OTAs entirely? That’s a binary outcome, and markets price those harshly. Multiples get cut because the uncertainty becomes existential, even if the business is breaking records today.

That’s the context for Booking.com’s $700 million AI reinvestment announcement. The company remains a massive cash-flow engine, but the market is pricing in a disruption that hasn’t yet shown up in the booking data. The real question is whether $700 million is a defensive move to plug a leak or an offensive bet to own the next era?

8. Fogel’s “Third Spouse” vs. The Agentic Threat

Looking back at Glenn Fogel, CEO of Booking.com, in his interview with Ben Thompson last September, this $700 million reinvestment starts to look less like a panic move and more like the “phase transition” he’s been signaling for years. Fogel’s core thesis is the “Connected Trip”, the idea that technology should finally recreate the role of the 1980s travel agent. He often describes this as a digital “third spouse” that doesn’t just book a room, but proactively fixes your dinner reservations or car service when your flight is delayed. The market is currently obsessed with the idea that AI will allow users to bypass OTAs, but Fogel’s bet is that while a generic LLM can plan a trip, it lacks the backend API integrations across flights, hotels, and attractions to actually execute and manage it when things go wrong in the real world. In a recent McKinsey interview, he was blunt about it: “It will be a very long time before LLMs crack the combination of execution complexity and trust that OTAs have spent two decades building.”

The tension here is between the search engine of the past and the service agent of the future. Fogel told Thompson that over 60% of their B2C traffic already comes to them directly, bypassing Google entirely. If Booking can use this capital to move from being a “toll collector” for hotel rooms to a proactive travel partner, that direct loyalty becomes much harder to break. The investment that Wall Street is currently punishing is essentially the price Fogel is willing to pay to ensure that when the Agentic AI era fully arrives, Booking is the one providing the infrastructure rather than being displaced by it.

9. Tryp.com’s feed hypothesis

Sharing a guest post from André Rangel, co-founder of Tryp.com: Tryp.com: Beyond the Search Bar.

His core argument is that the future of travel isn’t chat interfaces or better search bars; it’s algorithmic discovery. The new generation of travelers wants machines to handle the searching and discovery for them. Half of Tryp’s sales come from users who never typed a destination. They just swiped.

He also makes a sharp case for why LLMs can’t solve real-time pricing, how “feed data” beats 20 years of legacy booking history, and how they’re acquiring customers at under €5 CAC.

Worth reading if you’re thinking about the next generation of OTAs.

10. AI vs OTAs: Early signals from real travel sessions

The core finding from Directo’s new post on how AI assistants and OTAs coexist inside real user journeys is that AI is winning the moment of inspiration and OTAs still win the moment of payment.

Some key signals:

• 15-18% of OTA sessions already include a ChatGPT interaction in the same browsing session.

• Across the top 30 travel brands tracked in January 2026, ChatGPT referral rates ranged from 0.2% (Agoda) to 3.6% (Skyscanner). Small numbers, but in January 2025, most of these brands were near zero.

• 75% of travel AI conversations are purely informational.

This mirrors early metasearch dynamics. Influence without conversion.

Travel Tech Essentialist Job Board

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• Fora | Senior Product Manager, AI Agents & Data| New York City | $160k - $200k + Equity

• Expedia | Media Business Director | Los Angeles, CA; Seattle; NYC | $207k - $291k + Equity

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In a recent newsletter, I wrote about the conflict between eDreams and Tryp.com. Shortly after that, I reached out to André to hear his perspective. I wanted to understand the actual product philosophy they are building, beyond just the legal noise.

André argues that the future of travel isn’t about better search bars or “agentic” prompts; it’s about algorithmic discovery and “Feed Data.” Equally disruptive is their approach to customer acquisition. By leaning into a decentralized network of local “Country Managers,” Tryp is bypassing the traditional CAC trap in favor of viral, peer-to-peer narratives.

His thesis on the bias of legacy data and the limitations of LLMs for pricing logic is a compelling read for anyone tracking the next generation of OTAs. Thank you, André, for sharing these insights with the Travel Tech Essentialist community.

We don’t actually know what we want. But we think we know.

For two decades, the foundation of online travel—the “Search Bar”—has relied on the assumption that we do. Travel planning has historically been a risk minimization challenge. We go to the same places because, with limited vacation time and budget, we can’t afford to risk it on the unknown.

But this premise is becoming obsolete. The next generation of travelers—specifically Gen Z and younger Millennials—isn’t looking to minimize risk; they are looking to maximize discovery. They are traveling more than ever, but they aren’t searching anymore. They want machines to handle that for them.

Yesterday, I saw a LinkedIn post from a travel executive that perfectly illustrated the industry’s blind spot. He wrote:

“For 20 years, trips started inside an OTA. Guests opened websites. Scrolled. Compared. Booked. Now they say: ‘Plan me a 3-day trip to Copenhagen’”

The executive is right about the change, but wrong about the behavior.

I don’t want to type, “Plan me a 3-day trip to Copenhagen.” That is still work. That is still a prompt. The reality is that I don’t know if I want Copenhagen. I might want Lisbon, or maybe a hidden gem in Albania, provided the deal is right and the vibe matches my feed.

At Tryp.com, we now have behavioral data on over 6 million users. Half of our sales come from users who never searched for a specific destination. This confirms that the behavior we see on TikTok and YouTube—passive, algorithmic discovery—has finally arrived in travel.

The Chatbot Fallacy: Why You Can’t Build a House with Only a Wrench

This is where I strongly disagree with the current industry narrative. The travel world is obsessed with “Agentic AI” interfaces (LLMs) that force users to chat, type, and prompt.

But LLMs are a tool, like a wrench. They are incredible at what they do—completing phrases, understanding semantics, and sounding human. But just because you have a new wrench doesn’t mean everything suddenly needs to be built with hex bolts.

You cannot use a wrench to solve a math problem. And you cannot use an LLM to solve the “Traveling Salesman Problem” of real-time pricing.

LLMs are language calculators, not logic calculators. They cannot efficiently compute the price of 80 million ticket combinations in milliseconds. If you ask a chatbot to “find me a trip,” it is simply converting your words into a standard database query. It is just a “smarter” search bar.

The Data Paradox: Why “Less” Data is More Powerful

A skeptic might ask: “Expedia and Google have 20 years of booking history. How can Tryp win with just a few clicks?”

The answer lies in the difference between Search Data and Feed Data.

Legacy OTAs sit on mountains of data, but it is biased data. It is a record of intent, not preference. If a user searches for “London,” Expedia assumes they love London. But maybe they only searched for London because they assumed it was the only place they could afford. The data captures their constraints, not their true desires.

Our data is different. Because we show users a feed of everything—destinations they never thought of, at prices they didn’t know existed—their reaction (to swipe, to pause, to click) is unbiased. We don’t need 10 years of history to know what you want; we need 4 interactions with a truly open inventory to see who you are.

The Real Moat: Extreme Computation

Knowing what the user wants is useless if you can’t price it instantly.

Legacy OTAs rely on caching systems that are excellent for “A-to-B” queries but fail at open-ended discovery. If you don’t ask a legacy OTA exactly where and when you want to go, it literally cannot answer you.

booking.com, no cache = no offers:

Expedia, doesn’t try:

We built a graph database that ingests pricing for 80 million tickets (rail, bus, air, and ferries) across 7,000+ locations. We can bundle a flight, a train, and a hotel into a single price for a trip to “Anywhere” in milliseconds.

That is why “4 interactions” on our platform drives a 2x higher conversion rate. It’s not magic; it’s just the ability to compute a complex price the moment interest is detected.

The “Unsexy” Reality: Operations and Risk

Of course, building this is a nightmare.

We utilize Virtual Interlining (VI)—combining, say, a Ryanair flight with a FlixBus connection. This creates routes standard GDS systems never see, but it also creates “edge cases.” What happens if the bus is late? What happens if the flight is canceled?

Early on, we underestimated the operational weight of this. We thought code could solve everything. We were wrong.

We learned that you cannot automate empathy. We built “Sandra,” our AI agent, to handle 90% of queries, but we back her with a human Ops team that maintains a response time of under 5 minutes. We offer self-transfer guarantees to de-risk the bundle for the user. If a connection is missed, we step in. You cannot sell complex, multi-modal travel without owning the messiness that comes with it.

The Economics of Virality

Another hard lesson? You cannot beat the giants at Google Ads. Like many startups, we initially burned cash trying to acquire users via Performance Marketing. It was a race to the bottom where CAC eventually destroys earnings.

We pivoted to Decentralized Content. We recruited over 50 “Country Managers”—entrepreneurial students and scouts across Europe. They create localized, viral content (e.g., “How to visit 3 cities for €100”) that speaks the language of their peers.

The result is a Blended CAC of <€5 (vs industry standards often 10x higher). But more importantly, we are building a habit, not just a transaction engine.

• A very high percentage of users return.

• The median time between bookings is below 2 months

• 70% of revenue comes from mobile interfaces.

Entering the “Glass Box” Era

We are leaving the “Black Box” era of travel—models built on hidden pricing and dark patterns designed to confuse users.

We are building the “Glass Box.” We treat AI not as a trick to maximize conversion, but as a transparent agent for the user. If we do this right, we won’t just help people search for a trip. We’ll show them the one they didn’t know they wanted.

Special thanks to Propellic for sponsoring this edition of the newsletter:

On March 24th in NYC, Propellic, the leading AI-First Marketing Agency for travel brands, is partnering with Phocuswright to drive the future of the industry at their upcoming Travel Marketing AI Summit. It is a curated executive forum designed to cut through the noise, focusing entirely on real-world strategy from leaders deploying these technologies at scale, including executives from Google, G Adventures, Hopper, Tripadvisor, and Booking.com.

P.S. Do you want 20% off the ticket price? Find it here.

1. First-principles-driven tech trends

Contrary’s 2026 Tech Trends Report is a dense but sharp read on where value may accrue in the next cycle. The report groups the future into a few major waves: smarter AI (especially specialized agents), cheaper and more powerful computing, frontier technologies becoming real industries, and a new phase in medicine and healthcare innovation.

The analysis stays close to first principles. Rather than listing gadgets, they focus on how changing cost curves, data moats, and infrastructure bottlenecks will shape durable advantages. It’s a useful lens for thinking about which parts of the stack are becoming commodities versus where new defensibility might emerge.

What I appreciate about this report is that it treats “trends” as deep, slow-moving technology currents rather than surface-level vibes and consumer fads. It starts from foundational shifts in AI, compute, industrialization, and healthcare, then traces how behavior and business models will reorganize around them. That kind of first-principles lens is far more useful for travel than yet another list of hot destinations and trendy travel buzzwords, because it helps you see where value, power, and constraints in the broader tech stack are heading.

On transportation and mobility, the report argues that the real action is under the consumer layer: logistics orchestration, autonomy-ready infrastructure, and electrification. The advantage won’t be another slick booking front end. It will be control over how routes are optimized, who gets access to capacity, and who owns the underlying data.

2 The autonomous car risk-perception gap

An interesting section in Contrary’s Tech Trends Report is the gap between how safe driverless cars are and how safe they feel. Only 13% of US survey respondents say they trust autonomous vehicles; a clear majority remain afraid or unsure, despite millions of miles driven by autonomous vehicles now on the road.​

Waymo passed 100 million fully driverless miles in July 2025 and shows 80–90% lower crash rates than human drivers across Phoenix, San Francisco, Los Angeles, and Austin, depending on the metric. The authors estimate that if all US vehicles operated at Waymo-like safety levels, the country could prevent roughly 37,000 deaths per year and save around $1 trillion in societal costs.

Behavioral scientists would call this a risk‑perception gap; people anchor on rare, vivid incidents and headlines rather than the boring, statistical base rates. A media environment focused on AI-doomer narratives amplifies every driverless-car crash while largely ignoring the thousands of routine road deaths that happen every week. That distortion is also an opportunity for whoever can convert invisible safety into felt safety through product design, onboarding, transparency, guarantees, and narratives that make the math legible.

3. The Mexican standoff of roles

In a recent podcast with Lenny Rachitsky, Marc Andreessen described a “Mexican standoff” among PMs, engineers, and designers. His point was that with modern AI, each role now plausibly believes it can do the others’ jobs. Engineers think they can PM and design, PMs think they can design and code, and designers think they can code and PM; and they’re all a little bit right.

Underneath the joke is a serious career reframing. A “job” is just a bundle of tasks, and AI is rapidly rebundling who does what. Instead of asking “Will PM/engineering/design survive?”, the better question is: which tasks in my bundle get automated, and which new ones can I pick up?

This task rebundling is not new. Fifty years ago, a CEO dictated memos and an assistant did the typing and distribution; today, executives write their own emails, while assistants focus on higher‑leverage coordination and orchestration.

4. From T‑shape to F or E-shape

Marc highlights the opportunity to become a super‑powered individual. His advice starts with the classic T‑shaped idea: go very deep in one discipline, then build enough breadth across adjacent ones to collaborate intelligently. AI supercharges that model. You keep one serious spike, say engineering, but now have leverage to add PM and design skills across the top of the T without starting from zero each time.

Then he pushes it further. Instead of a single vertical and one horizontal bar, he imagines something closer to a sideways F or E, with multiple deep spikes, not just one. Scott Adams’ Dilbert only worked because he combined being a decent cartoonist with real business experience; Hollywood “auteurs” stand out because they can both write and direct; Taylor Swift is powerful not just as a singer but as a singer‑songwriter who also architects her brand and tours. The pattern is the same; rare combinations compound, they don’t just add. In an AI world, the goal is not to be just a PM, engineer, or designer, but to be unusually strong in at least two of them, with AI filling in the rest of the stack.

5. What airlines can learn from fashion retailers

The most interesting airline ideas could be in rewiring how demand is shaped. In a recent piece, JoseLuis Vilar (Caravelo co-founder) argues that some airlines no longer need seasonal sales because they have quietly embedded Zara‑style behavioral mechanics into their business model through subscriptions.

He highlights four principles of sales psychology that make Zara’s sales powerful: predictability, pre‑commitment, privileged access, and ritual, and shows how travel subscriptions deliver all four on a permanent basis. Instead of waiting for a January sale, subscribers know exactly when their flight quota refreshes each month, and the data he shares shows the median time from signup to first booking is under two days. They stop spending five hours and 141 page views per trip hunting (Expedia’s average) and start planning around a known rhythm and airline.

The kicker is that most of this demand is incremental. Across Caravelo partner airlines, only a minority of subscription flights cannibalize trips passengers would have taken anyway; the majority are either new trips or share‑shift from competitors. Subscriptions turn “looking around” into “using what I already paid for,” shifting the game from price competition in metasearch to competing on access, control, and cognitive offload.

6. When funders leave

Matt Lerner’s post about PayPal illustrates what happens when leadership loses its founder mentality. The inflection point came after the eBay acquisition; the founders left, former consultants and MBAs took over, and asset allocation thinking filled the organization. Of course, the travel industry is not immune to this phenomenon.

Lerner’s biggest wins came from unsexy work like fixing onboarding, tightening referral loops, and A/B‑testing service to reduce churn, all of which generated hundreds of millions in ARR with essentially no extra ad spend. Yet it became easier to get more budget for paid acquisition than to get engineers to fix the funnel. Departments began prioritizing their own P&L over customers. The focus shifted from solving customer problems to managing internal budgets. When more energy goes into “spending money” than into removing bottlenecks, the post-founder decline phase has usually begun.

7. Intensity as a founder’s strategy

That’s why a recent My First Million podcast about NBA owner and mortgage billionaire Mat Ishbia feels like the mirror image. Ishbia describes walking the floor of his thousands‑person company every day, talking to everyone from sales reps to IT, looking for three problems and fixing them on the spot. Over a year, that is roughly a thousand bottlenecks removed. The hosts call this “intensity as the strategy”; combining a simple, sharp thesis with obsessive attention to the details that block it. Founders live on a day-to-day contract with themselves; there is no guaranteed five-year, $150 million deal regardless of performance. Set against Lerner’s account of PayPal, the contrast is clear. Healthy companies still look like Ishbia’s daily floor walk, not like a budgeting meeting centered on how much more can be spent.

8. Travel & Hospitality Tech market update

AGC Partners just released its data- and insights‑rich “Travel & Hospitality Tech Market Update” for Q4 2025, showing where money and power are moving in travel tech. The report shows Travel & Hospitality Tech shares have grown roughly 2.8x since 2019 with expanding margins, and argues that investors are rewarding “quality growth” far more than raw profitability.

A few key points:

• This is now a big‑deal market. 2025 was the third consecutive record year for M&A value in travel tech, with large PE platforms and late‑stage VC‑backed players driving consolidation, particularly in aviation, restaurant tech, and hotel technology.

• Capital is there to keep the party going. PE funds are sitting on roughly $345 billion of dry powder, while listed travel‑tech firms collectively hold about $62 billion in cash and equivalents.

• The centre of gravity is increasingly B2B. Within lodging, the report argues that the highest‑value M&A is shifting toward commercial and marketing platforms that help hotels acquire and keep demand, not just core PMS infrastructure.

If you want a grounded view of how investors are pricing travel tech, who is buying what, and where capital is flowing within the stack, this deck is worth reading.

9. Solo travel seems to be more than a “trend”

Google searches for “solo travel” were flat from 2021 through 2024. Then something shifted. Starting in late 2024, interest spiked, and by early 2026, searches hit record highs.

The spike maps to a deeper behavioral shift. There has been an uptick in time spent alone, particularly among younger people, though it is present in all age groups (see first image below).

Activities done alone (such as gaming, social media, eating and drinking…) have surged. Social activities like walking with others or playing with children have declined (see second image below).

Lennart Dobravsky recently highlighted a striking data point: 29% of US households now consist of just one person, the highest share ever recorded, according to Apollo Global Management. That's 40 million Americans living alone.

The travel industry has not paid enough attention to this structural change. Solo travelers don’t need “singles cruises” or awkward mixer events. They need pricing that doesn’t penalize them, booking flows that don’t assume a “+1”, experiences that are also designed for one and restaurants that don't relegate them to the worst table by the kitchen or serve only shareable plates.

8. Travel tech job market insights 2025

I analyzed more than 10,000 active roles and thousands of candidate clicks and applications from the Travel Tech Essentialist job board. For this analysis, “engagement” refers to candidate actions on listings, primarily clicks and applications. A few clear patterns emerged:

• Remote roles generate roughly 5x more engagement per listing and account for about 30% of searches, yet represent only ~3% of posted roles.

• Sales and Business Development roles attract the most attention, driving 28% of searches and 31% of engagement. Product roles follow.

• The US leads in engagement (30%) and captures 22% of searches. Spain, Portugal, and Italy combined represent roughly a quarter of both search volume and engagement.

• Seniority matters. Manager roles see ~1.6x average engagement, Directors/Heads around 3–4x, and VP/C-level roles roughly 15x the average.

I break down the full analysis here.

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• Expedia | Head of Learning & Culture, Experience Design | San Jose, CA; Seattle; NYC | $231k - $398,500 + Equity

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1. The new speed of software

Meta spent $2B to acquire Manus, an AI agent startup. In only 10 days, Anthropic built and shipped their competitor, Claude Code, a full agent-powered dev tool, with every line of implementation code written by AI.

The big story is how fast software is changing, collapsing the layer between intent and execution. Shashwata Bhattacharjee’s post shows how engineers’ roles are shifting from writing code to orchestrating AI agents, managing validation pipelines, and identifying failure modes. The result is roughly 95% cost savings, 92% timeline compression, and development capacity that scales exponentially with human oversight instead of linearly with headcount.

In travel, agent-based planning tools, dynamic packaging, pricing systems, AI-native customer service and internal tooling from fraud to schedule optimization are all ripe for this kind of acceleration.

2. Management beats coding now?

That same compression is happening at every level. Ethan Mollick ran an experiment at Penn in which he gave executive MBA students four days to build a startup from scratch. Most had never written code. They used Claude Code and AI tools to build working prototypes, run market research, and create financial models, etc… What normally takes a full semester took four days. The prototypes had fully working features, the market analysis was sharp and the financial models made sense.

These weren’t CS students. They were doctors, managers and executives taking night classes. What they did bring to the table was years of experience scoping problems, defining deliverables, and spotting when a financial model or customer analysis was off. The students who performed best were those who already understood how to delegate and set clear goals. Their real-world experience gave them mental frameworks that translated directly into effective AI prompts.

Mollick built an equation for when handing work to AI makes sense. It has three components:

1. Human baseline time: how long would the task take you to do yourself

2. Probability of success: how likely the AI is to produce output that meets your bar on each attempt

3. AI process time: how long each round takes (prompting, waiting, evaluating)

If something would take you 10 hours but you can get AI to nail it in 2 hours of back-and-forth, you saved 8 hours. If something would take you 1 hour but you spend 2 hours getting AI to do it right, you wasted time. A key variable is Probability of Success. That’s where management skills matter. People who can write clear specs, evaluate output quickly, and give useful feedback get better results in fewer attempts. The AI doesn’t magically know what good looks like. You have to tell it. Read + Ethan Mollick

3. Your travel domain expertise matters more now

Mollick’s experiment has direct implications for travel founders. You can build a booking flow prototype in hours instead of months. Test pricing strategies in minutes. Generate customer service responses at scale. The constraint is whether you can explain what good looks like.

Can you describe what makes a trip planning experience work? What should a helpful rebooking email say? Which checkout friction actually costs conversions? Years in travel operations, customer service, or product work gave you judgment about these things. That judgment is what AI needs from you. The “soft skills” companies used to treat as nice-to-haves are now essential. When everyone can code via AI, the advantage goes to those who understand travel problems well enough to direct AI toward real solutions.

Your competitor who’s never worked in travel can spin up a booking platform over a weekend now. What they can’t do is recognize that handling rebooking chaos when connections get missed might be more of an issue than finding flights. They don’t know which support questions signal bugs versus confused users working around bad UX. You know these things. That knowledge just got more valuable.

Can you articulate what good service looks like clearly enough that someone else could execute it? If you can’t explain it to a person, you can’t explain it to an AI either. Domain expertise always mattered in travel. Now that execution speed is no longer the bottleneck, the advantage goes to those who know what to build.

4. ChatGPT’s 4% agentic commerce fee just went live

Starting January 26, Shopify merchants using ChatGPT to sell will pay OpenAI a 4% fee on every transaction. That’s on top of standard payment processing costs, bringing the total merchant costs closer to $7.10+ on a $100 order vs. $3.10 for traditional e-commerce.

As Dwayne Gefferie points out, this puts ChatGPT in direct contrast with Google Gemini and Microsoft Copilot, which currently charge 0%. OpenAI is betting their 800 million weekly users justify premium pricing. OpenAI controls distribution and now it’s extracting margin from it. They’re positioning closer to Amazon’s marketplace fees (8-15%) than affiliate rates.

5. AI’s balance sheet reality check

ChatGPT still dominates public perception of AI, with 800M+ weekly users and the #1 spot in Apple’s App Store. But OpenAI is burning cash fast at an estimated $14 billion in 2026 alone. Between the new 4% Shopify fee and ChatGPT ads, OpenAI is in a rush to monetize. For a company that once positioned itself as a research lab, this is a clear shift.

Meanwhile, Anthropic is pacing itself differently. Claude Code hit a $1B run rate in just six months. The company is targeting $20B–$26B in ARR for 2026, with 80% coming from enterprise customers, and expects to be cash flow positive by 2027 (source).

Google isn’t rushing at all. With $300B in annual ad revenue, Google's 650M monthly Gemini users won’t be seeing ads anytime soon (source).

The race is still open.

6. Tryp.com vs eDreams

eDreams has sued Tryp.com, accusing it of abusing the eDreams Prime subscription system to resell discounted Prime fares to Tryp customers and auto‑canceling Prime trials via AI. eDreams then canceled hundreds of tickets, which Tryp says included non-Prime fares. Tryp argues it’s merely acting as an OTA, representing users in finding the lowest fares, while eDreams similarly “scrapes” Ryanair. Airlines license inventory to intermediaries via explicit contracts and APIs, but Ryanair and eDreams have no such agreement, which makes eDreams’ position toward Tryp.com look uncomfortably similar to the airline stance it has fought for years. The clash has become a test case about fare access, dark‑pattern subscriptions, and whether an OTA can block a rival from using its consumer‑facing fares while still claiming a right to “open” access to airline inventory.

Maybe Tryp should spin out a new business to help people cancel their eDreams Prime subscriptions…😉

Quick poll…

7. The problem with most problems

Mike Maples famously passed on investing in Airbnb, and in this piece, he explains why. The problem wasn’t with the idea or the founders. It was with his framing.

Most founders look for pain points to solve. Ask someone in 2007 what frustrated them about travel accommodations. They’d say hotels were too expensive or poorly located. Nobody said, “I wish I could stay in a stranger’s apartment.” Those are conventional problems. You’re asking customers what they want improved within the current rules.

Maples argues the biggest opportunities come from explanatory problems: moments when reality stops matching what everyone believes should be true. The Airbnb founders launched a basic WordPress site offering air mattresses to make rent. The response surprised them. Standard theory said strangers wouldn’t trust each other with accommodations, but people did anyway. The anomaly exposed a broken assumption.

Most investors dismissed the anomaly with excuses: “Those early customers are a tiny market.” “That only works in San Francisco.” Each excuse let them ignore the evidence and stick with the old explanation.

In an AI world where execution is cheap and fast, solving conventional problems gets commoditized. What’s scarce now is perception…the ability to spot when reality has shifted and build a new explanation before anyone else sees it.

8. The rainy night every product needs

Jim Moylan died last month. You’ve never heard of him. But you’ve seen his invention thousands of times. In 1986, the Ford engineer pulled into a gas station on a rainy night and parked on the wrong side of the pump. He got soaked repositioning the car, then drove back to the office, still dripping, and typed a memo before taking off his coat. His idea was to put a small arrow next to the fuel gauge showing which side the gas tank is on. Ford added it within months, and then every automaker copied it.

Moylan’s frustration was real because he was living the customer experience. The arrow works because he felt the problem firsthand and was annoyed at the wasted time, just like countless drivers before him who couldn’t do much about it.

Travel companies that win obsess over tiny friction points. The ones that lose treat customer experience like a dashboard metric instead of something they’ve lived through. When Ryanair CEO Michael O’Leary flies his own airline, he experiences what budget travelers experience. When Airbnb’s Brian Chesky stays in listings, he sees what hosts and guests see. When Lyft’s CEO, David Risher, spends hours each quarter driving riders, he sees real driver UX, pricing, and support issues firsthand.

The next time you design a booking flow, walk through it on mobile with a bad connection. Check into your own hotel exhausted at midnight. Call your customer service line with a real problem. Your best product ideas will come from the moments that annoy you enough to fix them.

9. The next Golden Era of travel

This new Google × Alvarez & Marsal study is a 90‑page report packed with travel data to model travel’s long‑term future. It builds predictive models on 20‑plus variables, billions of Google searches, and 90,000‑plus tourism datapoints (plus airline data) to estimate future tourism flows and outline what a ‘next golden era of travel’ might look like. They expect global travel to roughly double to about 3.5 billion international trips and around 6 trillion dollars in international spend by 2050, with APAC becoming the largest source market, Europe staying the top destination, and domestic travel remaining the industry’s backbone at over 90% of trips. They also argue that volume alone won’t deliver profitability and that AI should be the industry’s primary enabler. This well‑structured scenario set is worth a read.

10. The physical world as competitive advantage

We spend a lot of time talking about digital tools, AI agents, and automation. This piece by my friend Isaac French is a reminder of what they can’t replace. His thesis is that AI will commoditize tools, creativity, and information. What it can’t commoditize is physical beauty and human care. You can’t download an environment. In the age of infinite outputs, what people are starving for is not more to do, but places to be. Places to belong. The hunger for real environments, for truth you can touch, will only grow.

This matters for travel. When AI handles booking, discovery, and personalization, the physical experience becomes your only real moat. Not your app. Not your algorithm. The room, the light, the thousand small acts of care that make people feel something. Most operators treat place as a backdrop. French argues it’s the product, and he’s probably right.

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• Airbnb | Communications Lead, U.S. Latino | $160k - $200k + Equity | USA; Remote

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What happens when AI explains your brand instead of your website?

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1. I ran Lenny’s podcast through an LLM

Lenny Rachitsky is a writer, investor, and host of one of the most popular product and growth podcasts. I ran Lenny’s 320 podcast episodes through an LLM to pull out insights especially useful for travel tech founders and entrepreneurs. Here are three that stood out:

1. Start with a narrow wedge (guest: Elena Verna, Growth advisor at Dropbox, Miro, SurveyMonkey). The best early traction usually comes from solving one specific, painful problem for a small group. A narrow starting point creates momentum and clarity. Strong use cases tend to grow outward on their own.

   • Implications for travel → Instead of going wide on use cases or audiences, focus on one clear pain, like planning for groups, or managing boutique hotel inventory, and build from there.

2. Community is part of the product, not a channel (Gina Bianchini, Founder of Mighty Networks). A strong community can drive retention, surface insight, and deepen engagement. It works best when it’s built into the product and connected to how people get value, not treated as a separate channel.

   • Implications for travel → For any travel business with creators, hosts, or user-generated content, the community can create trust and momentum. It’s especially useful for categories where peer input drives behavior.

3. Activation is the real bottleneck (Andrew Chen, General Partner at a16z, ex-Uber growth). Many products don’t struggle with discovery; they struggle to get users to the first valuable action. Activation is where most users drop off, and where growth teams should focus.

   • Implications for travel → Helping users complete a booking, share a trip, or take the first planning step matters more than just getting them to the site. Travel flows are complex, so activation deserves extra attention.

2. New: Travel product & growth co-pilot, powered by Lenny’s Podcast

I just released a new ChatGPT agent built for travel founders, operators, and execs. Try it here.

It draws from all 320 episodes of Lenny Rachitsky’s podcast and is designed to help you apply the best product and growth thinking to travel-specific problems, from onboarding and activation to PMF, retention, and go-to-market. It’s free to use and open to anyone building in and around travel.

Would love feedback if you give it a spin.

I asked it whether I should launch a generalist OTA. It gave a reasonable, nuanced, and well-argued answer. Short version: almost certainly no. Longer version: read it here.

3. Travel’s zombie narratives

If you’ve been reading travel news long enough, you start to see the loop. I say this with some guilt as I’ve echoed a few of these myself.

There’s the eternal Ryanair vs. eDreams feud; Michael O’Leary hurling “digital pirate” insults while an always unnamed eDreams exec issues a legal rebuttal no one reads past the second sentence. The Direct vs. OTA rivalry resurfaces every few months too, complete with “best rate guarantees,” assuming the guest remembers their loyalty number from three phones ago.

Then comes the Google Travel cycle, where OTAs spend billions outbidding each other in an ecosystem they call unfair. Every year, someone declares independence, only to quietly raise their ad spend a few weeks later. The Super App prophecy returns next, while last quarter’s “super” quietly gets sunset. Spring brings the Sustainable Travel Pledge. Q2 earnings quietly make it disappear.

Lately, the new zombie headline is AI ending metasearch or OTAs. It pops up every time someone demos a travel chatbot or flight tool, framed as the latest “existential threat.” The tech shifts, but the “end-of-an-era” script doesn’t.

And then there’s the “Brussels will fix it” arc. Offstage, the EU drafts another rulebook and billion-euro fines for “gatekeepers” and “unfair platforms” (almost always American), with promises to restore balance. A year later, the fines are priced in, the lawyers are paid, and the biggest players have turned compliance into a moat. Travelers foot the bill through higher prices, clunkier UX, and the products that never get built.

It’s a carousel of déjà vu headlines and recycled fights. If a story promises “the end of something,” a “revolution,” or “a new era of booking,” you can probably skip it. The ones worth your time aren’t on repeat.

4. Five clear rules for building in 2026

This deck from Megan Lightcap and the Creator Fund team highlights five clear principles for building trust, distribution, and staying relevant, especially in a crowded market where AI makes it harder to stand out.

• Customers trust people more than institutions. A real voice with accountability beats a polished brand every time.

• Go deep in a niche instead of chasing a category. Depth wins. A clear, specific audience with shared values is more powerful than a broad, generic market.

• Build a world around the product. Great products are easy to copy. What lasts is the story, culture, and community around them.

• AI culls the undifferentiated. If you’re generic, AI will beat you. If you’re specific, AI makes you more scalable.

• Short the mass market. Reach is cheap. Relevance is rare, and it’s what algorithms now reward.

5. McKinsey hires a creator economy advisor

More companies are starting to treat creators not as a marketing tactic, but as part of their core distribution strategy, including the ones you wouldn’t expect. Monica Khan, a former YouTube and Meta executive, has joined McKinsey as a senior advisor focused on the creator economy. She’ll work with Fortune 500 clients across media, tech, and consumer to build creator-led strategies for growth, go-to-market, and brand. She’s also helping build internal frameworks that shift enterprises away from one-off influencer campaigns toward long-term systems where creators act as partners in trust, storytelling, and distribution. McKinsey making a dedicated creator economy hire is a clear signal that creators are no longer just a side channel and should increasingly be treated as strategic partners and operating infrastructure for trust and distribution.

6. Google’s UCP: Agentic commerce comes for distribution

Google just announced the Universal Commerce Protocol (UCP), a new open standard that lets AI agents communicate with retailers, payments, and loyalty systems throughout the entire shopping journey, from discovery to checkout and post‑purchase support. In practice, it is an attempt to standardize how “agentic commerce” works so that agents can plug into Shopify, Walmart, Target, etc., without custom integrations every time.

The interesting bit is that UCP shows up directly in Google’s AI surfaces during checkout, using payment credentials already stored in Google Pay, with the retailer still the seller of record. That is Google moving one step closer to owning the intent, the interface, and now a clean hand‑off to transaction, without having to run the inventory or the risk.

Two travel‑relevant takeaways:

• Change “rug” for “hotel” or “tour” in their example and you can see exactly how this logic extends to trips: rich natural‑language queries, agent‑filtered options, and an inline checkout that never leaves the host surface. Whoever controls the agent and the protocol ends up setting the rules for discovery and value capture.

• Google is also introducing “Business Agent”, a new way for shoppers to chat with brands, right on Search. It’s like a virtual sales associate that can answer product questions in a brand’s voice, enabling retailers to connect with consumers during critical shopping moments and help drive sales. It keeps brands inside Google’s conversational environments rather than sending them off to build truly independent agents.

The rails for agent‑mediated distribution are being laid right now, and they’re being laid by the same players that already sit closest to demand. In consumer internet, the uncomfortable truth is that it’s rarely the “best” product that wins; it’s the product riding the strongest distribution rails. Google’s UCP is an attempt to lay those rails for agentic commerce. If you’re building anything that depends on owning the customer relationship, you need a view on whether you integrate into these agentic rails, try to compete with them, or design around them altogether.

7. Travel in 20 years

Instead of asking what will happen in 2026, OAG’s Travel 2045 report asks “Where will travel be in 20 years?” That long view forces sharper questions. What systems are becoming obsolete? What labor, infrastructure, and data dependencies are quietly breaking? Which categories haven’t been invented yet?

The report opens with a look back at five defining shifts from 2005 to 2025 and then offers ten long-range bets for what comes next. It frames this moment as a once-in-a-generation transition, one where autonomous systems begin making more of the decisions travelers used to make themselves.

8. Google Maps moves deeper into travel advice

Google is rolling out a new “Know Before You Go” section in Maps, a feature that surfaces practical, context-specific tips for places like restaurants, hotels, and venues. Powered by Gemini, it pulls from reviews and online content to answer questions travelers often ask too late: Is there parking nearby? What’s the dress code? Is there a secret menu? Read +

One implication is that reviews are making a comeback. As AI models rely more on real-world experiences to generate recommendations, the substance of those reviews starts to matter again. Not just the star rating, but the details, patterns, and context they contain.

Another step in Google Maps evolving into a real-time travel assistant, one that learns from what people actually say, not just what places claim to offer.

9. “Since when is life about happiness?”

When Dara Khosrowshahi was offered the Uber CEO job, he told his friend Daniel Ek (the founder of Spotify) that he was happy running Expedia. Ek responded: “Since when is life about happiness? It’s about impact.” [source]. That single line captures a mental model many founders quietly operate with but rarely articulate.​

Ek frames happiness as a trailing indicator of impact. You define the game, the arena where you want to matter, and happiness follows from doing consequential work there. In Dara’s case, Ek sensed he was “content, not happy”; he had largely solved the “Expedia puzzle”, life was easy, and that ease was a warning sign. Uber was a mess; chaos, regulation, and a chance to shape how cities work.

Two nuances are worth highlighting. “Impact” is personal and highly idiosyncratic. For another friend, Ek says he might give the opposite advice.​ “Go for greatness” is more a question than a universal command. Is the game you’re playing still worthy of your next decade? For founders, that’s a useful litmus test before the next raise, pivot, or exit conversation.

10. Dara Khosrowshahi: impact, measured in market cap

If Ek’s question to Dara was about upgrading the game he was playing, the market has since kept score in a very public way. The contrast between Dara’s Expedia chapter and his Uber chapter is, in many ways, what impact looks like when it shows up as market cap.

At Expedia, he took over a $4–$6 billion business in 2005 and left in 2017 with a company worth around $20 billion. That growth came from a decade of roll-ups, supply-side integration, and a relentless focus on turning a fragmented OTA landscape into a scale game, which made Expedia one of the two dominant global online travel agencies.​

At Uber, he walked into a cultural crisis: heavy burn, broken culture, and no clear path to profit. The private valuation in 2017 was around $76 billion. Today, it’s about $179 billion. That’s more than $100 billion in public-market value added during his tenure.

It’s not the only way to measure impact, but in Dara’s case, the scoreboard at Uber shows he stabilized a broken company and added over $100 billion in market value.

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1. Why agents aren’t booking travel yet

This post from Theory VC looks at why AI agents still struggle with real-world tasks like buying a car or booking international flights. The issue isn’t tools or intelligence. It’s trust. Most decisions fall outside a user’s “zone of comfort,” where the perceived consequences are too high or reversibility is too low. Booking travel, especially across systems and currencies, is still seen as a one-way door decision. There’s no good way to undo a bad booking, so users (and agents) hesitate. In contrast, software development works well for agents because it’s full of systems that make decisions easy to reverse and consequences easier to manage. Until those support systems for travel and other domains exist, agents will be limited to safer, more controlled environments.

2. AI prompts to find cheap flights

An X thread by Gina Acosta, viewed over 4.6 million times and bookmarked 63,000 times, shares six prompts she used in Grok to uncover flight-pricing tricks. One of them surfaced a $340 fare on a route that usually costs $1,200.

One of them: "Explain hidden city ticketing for my route from [departure] to [destination]. Find flights where [destination] is a layover city on a longer route that costs less. What are the risks, rules, and how much could I save? Give me specific flight examples."

3. What early AI success looks like

Bessemer Venture Partner’s State of AI report is a monster and well worth a read. It tries to make sense of the post–ChatGPT landscape with real benchmarks and clear patterns for what early success looks like. The report doesn’t just describe patterns; it backs them up with detailed examples of real startups.

They analyze two winning AI startup archetypes:

• “Supernovas” grow fast, hitting ~$40M ARR in year one and ~$125M in year two, but often with lower (average 25%) or negative margins and ~$1.13M ARR per FTE.

• “Shooting Stars” look more like great SaaS companies: ~$3M ARR in year one, 4x YoY growth, 60% gross margins, and ~$164K ARR per FTE in their first years

Bessemer’s point is that this era won’t be defined by a few outlier Supernovas, but by hundreds of Shooting Stars. That’s the benchmark most founders should focus on.

The report also looks into fast-moving areas such as vertical AI, agent-native browsers, and memory as a product feature. It looks at how AI is changing not just what software does, but how it works…tools that don’t just store data but act on it. It’s not travel-specific, but if you’re building in or around AI, there’s a lot in here that applies.

4. What gives AI founders an edge right now

Bessemer’s report is also about why some teams get there and others don’t. The difference is founders who understand what AI is genuinely good at, where it breaks down, and how to design around both. Products that remember, adapt, and plug into real workflows are proving harder to replace.

A few of their takeaways:

• Start with an AI wedge: Solve a narrow, high-friction problem (e.g., legal research, sales notes). Deliver 10x value fast, then expand.

• The browser is your canvas: Agentic AI is shifting to the browser layer; now a programmable environment where agents observe and execute. Build for this surface; it’s the new operating layer.

• Vertical AI is the new SaaS: “Technophobic” industries are adopting AI fast. Win by embedding deeply, proving ROI from day one, and scaling quickly.

• Incumbents are awake and acquisitive: SaaS giants are buying their way into AI. Build technical and data moats. Be M&A-ready, but operate like you’ll own the category.

• Taste and judgment are your differentiators: In a world of agents and automation, human insight is the edge. Founders who intuit what should exist (not just what can) will define the next era.

5. $1B plan to make airports more “family-friendly”

The U.S. Department of Transportation is investing $1 billion to improve the airport experience, with a focus on families. Plans include kids’ play areas, nursing pods, yoga rooms, and healthier food options. The initiative follows a recent DOT call for more civility and “elegant attire” in air travel. Some airport architects point out that many of these upgrades are already underway, while others question whether amenities like gyms or kale will move the needle. Critics say the focus should be on basics: clearer announcements, working infrastructure, and less crowding. Read + AFAR

6. How travel companies score on culture

The Economist partnered with CultureX, a firm co-founded by MIT Sloan’s Donald Sull, to analyze employee reviews from 900 companies across 19 industries, including Travel & Leisure. Using language models to assess how employees describe their experience (not just ratings), they scored companies on topics like leadership, work-life balance, transparency and agility. The interactive tool lets you explore how companies compare and how their cultures have shifted post-COVID. Read +

7. The quiet return to office

Return-to-office pressure is picking up again, but more through signals than mandates. Promotions tied to face time, tighter tracking, and the quiet understanding that being in the room still matters. The WSJ calls it “hybrid creep,” and the data backs it up: office buildings tracked by JLL are now 67% full on Mondays and 56% full on Fridays. Mondays are now as busy as Wednesdays were in 2023. Fridays have almost caught up to Wednesday levels from 2022.

Culture is shaped more by what gets rewarded than what’s written down. Shout out to my friend Dave Morgan, founder and CEO of Simulmedia, who doesn’t play games with this stuff: “If companies believe that their teams are better together, in person in office, they should be open & explicit about it. That’s what Simulmedia does. No stealth. No games.”

8. Where the leverage is

In 2025, Alphabet’s market cap rose from $2.3 trillion to $3.8 trillion, adding $1.5 trillion in value in a single year. That’s more than five times the combined market caps of Booking (~$175B), Airbnb (~$84B), and Expedia (~$34B). Put differently, Google created more value in one year than three decades of the world’s largest online travel agencies.

Of course, it’s an apples-to-oranges comparison…search, ads, and infrastructure operate on a very different scale than travel transactions. But that’s the point. The deeper you are in the intent layer, the more everything compounds.

9. Brand quakes: details that redefine loyalty

Rory Sutherland’s “brand quake” is the moment a brand does something so unexpectedly good that it permanently upgrades how a customer feels about it. It is less about being good on average and more about a vivid, emotional peak that rewires loyalty and drives word of mouth. He often illustrates this with the post office: if your postman is unexpectedly kind, reliable, and genuinely helpful, that interaction overwhelms whatever the official marketing says about the postal service. And vice versa, of course. The everyday human contact becomes the brand, because that is what people actually feel and remember.

In travel, disruption moments (delays, cancellations, failed bookings, medical or logistical scares, etc…) are prime quake territory. Most brands respond with rigid policies, but a brand-quake mindset asks: how can this be turned into a story the traveler can’t stop retelling? Proactive rebooking, generous credits, or a human follow-up can create a quake that makes price and feature comparisons less relevant and turns a functional platform into a trusted companion. Faye Insurance is a good example of a company that appears to understand this, operating as if its main job is to turn stressful, high-stakes situations into reassuring, story-worthy experiences rather than bureaucratic nightmares.

10. The offline experience is a growth bet

In the past month, over $500M in funding has gone to companies betting on in-person connection. Andreessen Horowitz launched an invite-only dinner series for founders. Rodeo, started by Hinge’s former COO, is building tools to help people spend more time with friends offline. The former Hinge CEO is working on Overtone, an AI-powered dating app focused on IRL outcomes. Ari Emanuel, CEO of TKO, just launched MARI, a new global live events company. Startups are also hiring for roles focused entirely on real-world engagement.

There’s clear momentum behind products that bring people together face-to-face. Travel has always been about in-person connection. The opportunity now is building tools that make those moments easier to access, share, and return to. (Via The Collective)

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This is the last newsletter of the year. I’m grateful to all of you for subscribing, reading, and engaging. Wishing you a Merry Christmas, a Happy New Year, and a great start to 2026!

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1. Storytelling needs humans

Microsoft is hiring storytellers at $300k. Google, USAA and others are doing the same. This short post by Paul Stanton breaks down why narrative is becoming a core requirement for big tech, and for anyone building in public or raising capital, whether for a startup or a fund.

Founders (and GPs) who can clearly communicate their market view, traction, and long-term vision are separating from those who just update a pitch deck. Customers, investors, and talent still care about the numbers, but what they remember is the story, especially early on when the numbers are insufficient or nonexistent.

2. Personalization is only real when it’s human

I got this email from Frontier with a subject line telling me to “leave the cold behind.” The only problem: I live in New Orleans, which isn’t exactly a cold place. It was 76°F (24.5°C) that day…hardly a reason to “leave the cold behind.” It also claimed the offer was “just for me,” which, of course, it wasn’t. Mail merge ≠ Personalization.

Contrast that with what United did. I flew yesterday (1 day after my birthday), and the crew handed me a handwritten card from the pilots and flight attendants, wishing me a great year of travel. The fact that it was the day after my birthday made it feel even more real.

One was automated and off-target. The other was small, thoughtful, and spot on. The tech is easy. The trust is the hard part.

3. Airbnb’s 2026 predictions are out

In my last newsletter, I shared my own take on 2026 travel trends, including the Belgian who moved to Barcelona last Tuesday and is already yelling at tourists to go home. This week, Airbnb released its official 2026 predictions. It’s more polished than mine, but we’re in synch. Airbnb’s key takeaways:

• Gen Z travelers love 1-2 day international trips to cool cities

  (Translation: young people with limited time and money still want to go to fun places)

• Interest in outdoors and nature is surging
  (Translation: Parks are pretty, good for your brain, and free/low-cost)

• Big events drive bookings
  (Translation: Turns out people want to be where things are happening)

• Travelers to France like food
  (Translation not needed)

All jokes aside, their release is worth a look; unlike most “Megatrends” out there, their data brings real depth and context to what travelers are doing.

4. VCs are not investing in non-AI (at all)

Bill Gurley spent decades as a partner at Benchmark, one of Silicon Valley’s most respected venture capital firms, backing companies like Uber, Zillow, and OpenTable. He has seen multiple technology cycles play out from the inside. When someone with that background speaks plainly about startups and capital markets, it is usually worth paying attention.

In a recent conversation with Tim Ferriss, Gurley described the current funding environment in the simplest possible terms:

“Institutional investors have zero interest in non-AI deals. Zero.” — Bill Gurley

Gurley was simply describing how capital is being allocated right now. This has little to do with whether AI is overhyped or whether every product truly needs it. Capital moves in waves, and the current wave is entirely focused on AI.

If you are building something that is not AI-related, you may still be building a good business, but you are operating outside the attention span of institutional investors. That matters because venture funding is path-dependent. Angels think about follow-on rounds. Founders think about who will fund the next stage.

As a result, even solid, sensible businesses can struggle. Not because they’re flawed but because they sit outside the current narrative. Right now, the funding market is highly concentrated, and almost all of that attention is on AI.

5. Where the real AI opportunities are

Bill Gurley believes that the era of building a new foundation model as a startup is effectively over. That game now requires enormous amounts of capital, infrastructure, and access. If you think you are going to back the next OpenAI as an angel investor, you are not being realistic.

Where he sees opportunity is in companies that sit deep inside specific industries, applying AI to complex workflows, proprietary data, and real operational problems. Areas that require context, domain expertise, and an understanding of how work actually gets done. Software that automates processes, connects fragmented systems, and reduces friction inside complex organizations. Not the kind of things that show up on OpenAI or Anthropic’s immediate roadmap.

“I don’t think it will make sense for OpenAI to go crush every little vertical.” — Bill Gurley

For industries like travel, hospitality, and logistics, this should sound familiar. Workflows are messy, data is fragmented, and a lot of the work is still very human. Bill Gurley and Tim Ferriss

6. A practical note on careers and AI

One of Bill Gurley’s most practical points had little to do with startups or venture capital. It was about careers.

AI is going to affect almost every role, whether you work in tech or not. And ignoring it is not a neutral choice. Gurley’s view was straightforward. The safest response is familiarity.

“I don’t care what field you’re in, you should be playing with this stuff. It has the potential to impact your career, and the best way to protect it from AI is to be the most AI-enabled version of yourself you can be.”

This is not about becoming technical or chasing every new tool. It is about understanding what these systems can do, where they help, and where they fall short. What disappears in technology shifts is rarely expertise. It is rigidity. Expectations around speed, output, and judgment are already changing, and they will continue to change whether we like it or not.

For most professionals, the risk is lower that AI will replace us overnight. It is that someone else learns to use it better, faster, and more comfortably than we do. Over time, that gap compounds. Those who reject these tools on principle fall behind, often without noticing it until it is too late.

Standing still and acting like change/progress/technology is bad has never been a great career strategy. It is even less so now.

7. Travelers are highly receptive shoppers

Rory Sutherland, Ogilvy’s Vice Chairman and a longtime behavioral economist, recently shared this post on LinkedIn explaining that people planning a trip are unusually open to change and more likely to say yes to new things.

In his work with Expedia, he found that travelers are 20% more likely to be shopping for a car, 27% more likely to be seeking cosmetic advice, 29% more likely to make in-app purchases, and 12% more likely to want to try new restaurants. Travel planning puts people in a different headspace. They’re more open, more curious, and more willing to try things they wouldn’t consider in day-to-day life. That creates real opportunities for non-travel brands to get in front of people when they’re paying attention.

8. Building travel brands for the AI economy

This guest post from Mario Gavira explores a provocative idea: if AI reduces the need for entry-level knowledge work, we could see downward pressure on middle-income wages — even as services powered by AI become cheaper to produce. If that shift plays out, the structure of consumer spending may change in ways travel companies can’t ignore. Mario suggests that travel may need to position itself less as entertainment and more as a way to deliver meaningful outcomes, such as health, growth, and a personal reset. He offers clear, practical examples of how brands might respond.

9. Flight subscriptions done right

Everyone's been dunking on Ryanair for killing off its subscription model after less than a year, calling it proof that flight subscriptions don’t work. But as Caravelo points out in this report (based on 600,000+ subscription flights and 200,000+ travelers), the real issue was the execution. According to the report, Ryanair’s version likely didn’t attract new customers or deepen engagement with existing ones. In other words, it didn’t change behavior. People just used it to get discounts on flights they were already planning to take, which looks more like couponing than loyalty.

The report is specific and grounded in actual behavior, rather than vibes or survey answers. Their key takeaway is that when done right, subscriptions build habits, attract under-45s who’ve long disengaged from traditional loyalty, and unlock travel that wouldn’t have happened otherwise. It's worth a read if you’re in the business of loyalty, subscription models, or trying to understand what modern travelers are actually doing (vs. what we think they might do).

10. This explains a lot

Your privacy settings might be the reason your 2026 wishlist didn’t happen.

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Mauricio Prieto

I’ve been lucky to know Mario since our time working together at eDreams Odigeo. His perspective is always clear-eyed and thought-provoking. Grateful to him for sharing this piece with us.

I recently fell down a rabbit hole reading Simon Taylor’s brilliant piece, “AI is Rewiring the Economy,” and it stopped me in my tracks.

While the travel industry is busy buzzing about how AI can make our booking engines 10% faster or our customer service chats slightly less robotic, we are ignoring a structural tsunami that is about to hit all industries. We are obsessing over efficiency, but we aren’t talking about solvency.

Taylor argues that AI isn’t just a tech upgrade; it’s a “rewiring” of value. This creates a fundamental question: What happens to your business model when the technology you use also destroys the purchasing power of the people buying them?

Here are the 3 phases Taylor describes in the piece and how monetization will evolve:

“Phase 1 (Today): We’ll apply AI to existing commerce - better ads, smarter checkouts - but volume remains low because fewer people can afford to buy

Phase 2 (2027): Winners emerge by commoditizing knowledge work, creating abundance in services, while scarcity emerges in consumer spending

Phase 3 2030+: Consumer-facing AI shifts from facilitating purchases to optimizing human outcomes.” — Simon Taylor

By 2030, we will face a paradox: an abundance of cheap services, but a scarcity of consumer cash. The only way to generate revenue from a poorer global customer base is to stop selling “Luxury” and start selling “Necessity.” People will not spend money on “fun”; they will only allocate resources to things that tangibly improve their survival—health, self-fulfillment, and well-being.

As Taylor puts it: “The companies building for ‘Gross Domestic Flourishing’ instead of Gross Domestic Product get to define it.”

Why Travel is the Ultimate “Flourishing” Engine: Travel is uniquely positioned to win in this outcome-based economy because it is the ultimate “pattern interrupt.” Travel physically acts as a visceral reset for the brain and body. Whether it’s the physiological benefits of forest bathing or the cognitive plasticity gained from navigating new cultures, travel is not just a leisure activity—it is the single most effective vessel for self-realisation. It isn’t just a break from work; it is the infrastructure for becoming a better human.

The New Business Model in Travel: Architecting the “Better Angel”

This is where the rubber meets the road. If the economic model changes, the relationship between the travel company and the traveler must undergo a radical transformation.

To survive, travel brands must evolve into new roles. Some examples how Travel Brands can reposition themselves are:

• The Chief Vitality Officer:
  Stop acting like a booking agent and start acting like a doctor. In this model, you aren’t selling a “vacation”; you are selling a biological intervention. The AI rigorously selects destinations and itineraries not for their “Instagrammability,” but for their proven ability to lower cortisol, improve sleep latency, or boost cardiovascular health. You don’t sell the trip; you sell the outcome.

• The Architect of Ambition:
  An “Architect” designs the structure that makes success inevitable. Here, travel becomes the vehicle for the user to become the person they want to want to be. The travel company uses data to curate experiences that force creative breakthroughs, deep work, or skill acquisition. The metric of success isn’t “did they have fun?”, but “did they grow?”

• The Destiny Steward:
  In a world of infinite choice and limited means, the ultimate luxury is curated constraint. The Destiny Steward uses AI to align every spending decision with the user’s long-term life goals. If a customer has limited funds, the Steward ensures those funds are directed only toward travel experiences that compound in value—networking, education, or family cohesion.

The Final Thought: The Era of Radical Customer Centricity

In a few years, AI agents will act as the gatekeepers of commerce. These agents will filter the world for us, selecting products and services based strictly on outcomes, not marketing. An AI agent doesn’t care about your glossy Instagram ad or your catchy slogan; it cares about measurable outcomes. It will ask: Does this trip measurably improve my principal’s health? Does this itinerary actually lower their stress levels?

Growing revenue in this world requires radical customer centricity. You are no longer fighting for attention; you are fighting for alignment. To win, you must optimize each individual service as a flourishing experience for your travelers.

Beware.

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1. Travel Megatrends 2026: Ctrl+C, Ctrl+V + a few new buzzwords

Right about now, the usual suspects are preparing to release their groundbreaking 2026 megatrend reports. New year, same trends. Here they go:

• Sustainable Travel. Pay extra to feel bad, then pay more to feel good about feeling bad.

• The End of the OTA: For the 14th year in a row.

• AI: Your new travel agent now judges your life choices and books you a 10-day vow of silence in Bhutan because you seemed tense.

• Loyalty: Gamified Stockholm Syndrome. Earn your way back to basic benefits you used to get for free.

• Personalization: The algorithm noticed you like hotels. So now it shows you more hotels.

• Off-the-beaten-path luxury: Private jets to secret coves already tagged 4.7M times on Instagram by the same people warning you about overtourism.

• Overtourism: Loudest from the influencer on her fourth Bali trip this year and the digital nomad who moved to Barcelona last Tuesday and now wants tourists gone.

• Slow Travel: Luxury trains, boutique cruises, e-bikes, and walking, the slower the better, while lecturing about planes.

• Bleisure Nomadism: Nothing screams freedom like WiFi-dependent serfdom

• Experiential Travel: deep connection means chasing the northern lights while live-streaming to strangers

• Wellness: Expensive mud baths, mushroom ceremonies, and sound healings now rebranded as “mitochondrial realignment.”

• Live Event Tourism: Sports, music festivals, eclipses, reunions... basically herding cats with passports.

• Luxury Class: Happily spends 40% more to stay nowhere near you, then posts black-and-white reels captioned “This used to be paradise… before everyone came.”

• The Connected Trip: although it’s now rebranded as “agentic experience environment”.

My personal 2026 megatrend is Nostalgia Tourism to 2020—staying home and avoiding carbon shaming and overtourism outrage. Who’s with me?

2. Groceries as souvenirs

This WSJ article makes a strong case for food as the most underrated souvenir. Instead of buying junk you’ll throw out in a year, travelers are bringing home ingredients from local supermarkets and hosting dinner parties to share the experience. It also reflects a clear behavior shift: 40% of travelers now make a point of visiting grocery stores abroad, and 44% go out of their way to find foods they can’t get at home. TikTok grocery walkthroughs now get up to hundreds of thousands of views.

The article highlights some examples, such as hot sauce from Belize, cloudberry jam from Norway, barley-rusk croutons from Greece, paprika chips from Spain, Portuguese sardines, and Japanese matcha…plus a few practical tips for packing, cooking, and gifting.

And if you’re visiting New Orleans, here are a few things you’ll want to bring home with you…

3. 2026, if you’re building with AI

Greg Isenberg’s 2026 predictions are the kind I like: actionable and grounded in what builders are already experimenting with. Some are out there (agents with crypto wallets), but plenty feel immediately useful if you’re working on lightweight tools, agent workflows, or new consumer interfaces. Here are a few standouts and their implications for travel:

• Micro-companies built on agents serving niche communities could open up new paths for solo founders…think destination-specific concierge agents or personalized travel planning tools.

• Search replaced by answer synthesis. Browsers that read 50 sources and return a single output will reshape how people find and book. The trip-planning funnel could be up for grabs.

• Disposable software. One-off apps that exist for a single trip, event, or experience. Useful for short-term campaigns or personalized services.

• Agent-run media. Daily travel digests, hotel content, or local guides produced autonomously or with just a human editor.

• The invite-only web. As trust and reputation become scarce online, curated, closed ecosystems become more valuable. Lots of implications for marketplaces and discovery layers.

4. A crash course in building with AI agents

More from Greg. He put together a tactical guide to launching an AI startup in under 3 hours for less than $500. The playbook leans heavily on off-the-shelf AI agents to handle everything from product ideation to coding and sales ops. It’s framed around a 5-step workflow:

• Find the right idea/trend with tools like ideabrowser.com

• Sketch out the idea with tldraw

• Feed it into Manus to scope and structure your MVP

• Use Bolt.new (a code generation tool) to build a working prototype

• Set up automated lead-gen and sales agents with Lindy

Greg’s full breakdown is here

5. How to ask for an investor intro

If you’re asking for an investor intro, make it easy for both the person forwarding the email and the investor to decide whether it’s worth their time. This is a clear, no-fluff guide from David Booth, who used to write the “featured startup” blasts at AngelList and has helped thousands of founders get connected. He breaks down exactly what to send, how to structure it, and what to leave out. Here’s the format he recommends:

• Send a fresh email with the subject line: “intro: [your name (company)] <> [name of investor you want to meet]

• Open with a short note such as “Thanks for offering to intro me to X. I’d particularly love to connect because [one clear reason…specific to their thesis, past investments, etc.]”

• Four bullets (one sentence each) on:

  1. What you do and the problem you’re solving

  2. What traction you have, or why it’s working

  3. Who’s on the team, and why they’re right for this

  4. Fundraising status (what you’re raising, what’s committed, past investors, etc)

If the bullets are strong, you don’t need to attach a deck. Just send that once you’re introduced. The goal is to make it easy for someone to help you while giving the investor just enough context to decide if it’s worth a conversation.

6 Where private equity money might be moving in travel

This new McKinsey report (framed for private equity) is also a helpful map of where consumer demand and infrastructure gaps are emerging in travel. It covers three primary shifts: experiential travel, luxury demand, and tech integration. A few points worth pulling out:

• Discretionary spending in the US has been steadily shifting toward experiences over goods since the 1990s (see image) and travel is taking a growing share of wallet, with rising interest in categories like adventure, culinary tourism, wellness, and night-based activities (northern lights, nocturnal safaris…). More than 60% of travelers want to explore lesser-known spots.

• Luxury is expanding. High-net-worth travelers are younger and more global, and they’re showing a strong preference for multi-trip, high-touch travel, often blending luxury with adventure or wellness. From 2015–2025, luxury travel in North America grew at 12% CAGR, compared to 3% for the overall sector.

• Planning behavior is changing fast. 29% of consumers already use gen AI for some part of their travel planning and AI-driven referrals show a 45% lower bounce rate on travel websites, suggesting higher user intent and trust.

• Infrastructure is lagging behind demand. There are ~210,000 yachts globally but only ~160,000 marina berths, and marinas are adding just 300 berths every 5–10 years. The gap is sharpest in the Mediterranean. There’s similar friction in expedition cruises. Founders building around logistics, services, or tech for these categories could benefit from that mismatch.

• Live event tourism. Nearly 1 in 5 travelers now plans trips around concerts or sporting events. There’s growing opportunity in bundling around these events and some brands are already building hospitality products around this behavior.

7. Experiential rewards work better

Not one to share too much academic research in this newsletter (I usually favor things that are closer to the ground and tested in-market), but “When rewards connect to the self: Unlocking customer engagement through experiential rewards” from researchers at Michigan State, San Diego State, and the University of Alabama stood out when I saw it in the Science Says newsletter.

Across six studies (four in the lab, two in the field), they found that even small experiential rewards consistently drive more engagement than material ones. That includes more word of mouth, stronger loyalty, more redemptions, and more spending both before and after the reward.

People see experiences as part of their identity, not just a transaction. That makes them feel closer to your brand. Experiences feel more personal, and they lead to better results. The value of a reward lies more in the connection it generates than in its size.

8. AI adoption is mainstream, but true transformation hasn’t really started.

McKinsey’s State of AI in 2025 report shows adoption is broad, but depth is lacking. 88% of companies say they use AI, but only a third have scaled AI agents, mostly in tech, media, healthcare, and insurance. Travel ranks lower on the spectrum. Most companies remain in experimentation and pilot mode.

The high performers (top 6%) approach it differently:

• 55% have redesigned workflows (vs. 20% of non-high performers)

• 82% set growth targets for AI use (vs. 50%)

• 50% intend to use AI for enterprise-wide transformative change (vs 14%)

• 35% invested more than 20% of digital budgets in AI (vs. 7%)

• They’re 3x more likely to have senior leaders personally accountable for AI

9. The lawsuit that could change how travel is sold

According to this post by Mario Gavira, a court case between Amazon and Perplexity might be one of the most important legal battles for the future of online commerce and travel.

At stake is whether AI agents have the legal right to act as digital proxies for consumers. In other words, can they browse, compare, and book on your behalf without permission from the sites they interact with?

This piece outlines two diverging scenarios depending on who wins:

• If Amazon prevails, the current ecosystem of OTAs, metasearch, and supplier partnerships stays “protected”, but AI agents must go through formal partnerships and gated APIs. Some sort of a certified agent program.

• If Perplexity wins, we enter a free-roaming, agentic web. AI agents can scrape and transact independently, potentially disintermediating OTAs while reshaping how inventory is found and booked.

10. All we need is…

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1. The Charlie Munger Mindset: Design Against Human Error

Charlie Munger’s legendary talk, The Psychology of Human Misjudgment, was originally meant for investors, but it provides an essential roadmap for founders and entrepreneurs. By detailing 25 psychological tendencies, Munger shows why smart people make predictable errors. We should be aware of these biases and design products and companies that actively counteract them. Here are a few takeaways based on Munger’s key tendencies:

• Your friends give you bad feedback. The Liking/Loving Tendency means your friends and early supporters will give you dangerously positive feedback. Useful feedback comes from strangers with no incentive to be nice.

• Incentives drive everything: Munger warns that the Reward/Punishment Bias is always underestimated. Understand the incentives of every market participant (user, competitor, supplier) and design your product’s flow and revenue model to align the user’s long-term outcome with your financial incentives.

• Fight your own ego. The Self-Regard Bias makes it impossible to kill your own ideas. Munger admired Darwin because he actively sought out facts that contradicted his own theories and wrote them down immediately. Build systems that force disconfirming evidence into the room.

• Loyalty from failure: Your best moat can be great service during a crisis. Reciprocation and Kantian Fairness mean investing in recovery during high-stress moments builds vastly more loyalty than when everything is working smoothly. (Munger reminds us this tendency is so strong that a favor, even one with clear strings attached, creates an automatic bond.)

The full text with all 25 principles is worth a read and will help you design better systems by understanding how people actually think.

2. The art of procrastination

In this post, Paul Graham argues that since it’s impossible to work on everything, the question isn’t how to stop procrastinating, but how to procrastinate well. The most impressive people he knows are all big procrastinators, but they’re strategic about it. Graham defines three types of procrastination:

• Type A: Doing nothing (paralysis). This is often rooted in fear or feeling overwhelmed by a large task. Overcoming it requires building momentum by breaking the goal down into extremely small, controlled starting steps.

• Type B: Doing something less important (busy work): This is the most dangerous type. It involves completing low-leverage tasks (such as constant email checking) that give a false sense of accomplishment. The simplest test for this is: Will this task be mentioned in your obituary? If not, it’s stealing time from your mission.

• Type C: Doing something more important (the good type of procrastination). When an individual avoids a small administrative task (like an errand) in favor of working on a more complex, higher-leverage problem, they are strategically prioritizing. Successful figures who eliminate small decisions (like wearing the same outfit daily) reserve their mental energy for their biggest goals.

Graham argues that real work needs two things that errands don’t: long stretches of time and the right mindset. Type C procrastination protects those conditions. By putting off small tasks, we can avoid the interruptions that break focus and kill momentum. Sometimes that’s the only way to carve out space for work that actually moves the needle.

Graham suggests asking “What’s the best thing you could be working on, and why aren’t you?” He advises that instead of letting a to-do list push you, you should let delight pull you into an ambitious project. If you are working on the biggest things you could be working on, you’re leaving the right things undone.

3. The cost of interruption

Context switching is the silent killer of deep work. Research from the University of California, Irvine (UCI) shows that constant digital interruption attacks your focus in a compounding, two-part cycle.

These studies, conducted over two decades ago (2004-2008) using IM and telephone interruptions in an office environment, are even more relevant now because our smartphones put the source of constant distraction right in our pocket.

The UCI results suggested that after a digital interruption, it takes over 23 minutes to fully reorient and regain deep concentration. That’s the baseline time lost. However, later UCI experiments found that when workers were constantly interrupted, they completed tasks faster than those who weren’t. This speed is forced compensation. Your brain attempts to beat the 23-minute reorientation cost by rushing, pushing you into a frantic, high-stress work mode that results in significantly higher frustration and mental effort. The consequence is that your brain trades mental stability for speed, which leads to burnout and compromises the quality of your output. The most vital strategic work requires mental stability, so we should be ruthless about carving out interruption-free blocks.

4. WeRoad on My First Million

I was listening to My First Million and was happy to hear them talk about WeRoad. Sam Parr described it as solving a loneliness problem for solo travelers (WeRoad segment from the episode). The company started in 2017 and is now doing over $100M in revenue ($160M projected for 2025), with 30% gross margins. They’re doing it with sharp packaging, smart ops, and community-first design.

WeRoad offers small-group, Millennial-only trips built around shared moods and travel styles such as Patagonia treks or cultural tours in Japan. Groups are 8 to 15 people, logistics are handled, and the trips are led by passionate travelers, not professional guides. The vibe is more like a group of friends than a traditional tour. Many come back with new best friends. Some come back in relationships.

There’s still room to rethink classic travel formats. Seniors have group tours. Students have options like EF and others. WeRoad tuned the model for a generation with disposable income, limited time off, and a desire for connection. A newer player, YourFriendsAreBoring, launched in 2022 and is exploring similar territory, starting with trips for people tired of group chat indecision and ready for real adventure. Whether you call that solving loneliness or just building community, it’s clearly working.

5. Agentic AI moves from demos to bookings

In a recent Travel Weekly piece, Robert Silk wrote about how agentic AI is starting to shape real traveler workflows. Perplexity’s Comet browser can already search for flights, fill in your personal info, and complete a booking without you lifting a finger. Hopper is using voice/chat to manage rebookings. SkyLink is building full itineraries for corporate travelers, factoring in policy and personal preferences.

Since that article, Google has launched its own set of agentic tools inside Search (link). It starts with Canvas, a new workspace that builds flexible, real-time trip plans using flight data, hotels, Google Maps info, and local suggestions. Their AI Mode can help you choose between tradeoffs (like proximity vs. price), remember where you left off, and refine plans over time. There’s also a new Flight Deals feature that shows low fares based on broad prompts like “somewhere warm in February.” It currently stops short of handling bookings directly, but Google says its AI will soon be able to complete flights and hotels as well, thanks to new partnerships with Booking.com, Marriott, Expedia, and others.

Agentic AI is moving to becoming a default interface. Some tools still pause at checkout and others don’t, but the search–plan–book gap is closing.

6. Inside the Marriott–Sonder collapse

Last year, Marriott partnered with Sonder to add 9,000 apartment-style rentals to its platform. Guests could earn Bonvoy points and Marriott could boost inventory without building more hotels. This month, the partnership imploded: guests were suddenly told to vacate, and digital keys stopped working. Marriott says it had already sent Sonder $1.5 million just to cover a week of payroll and taxes. Now it’s in court trying to recover $17.7 million.

The WSJ has the full story, including how the deal came together, why Sonder ran out of runway, and what it signals for asset-light inventory models.

7. Since the launch of ChatGPT…

On November 30, 2022 OpenAI launched ChatGPT, marking the start of the generative AI boom. AI has reshaped investor expectations across every sector. Since then, the gatekeepers (Google, Microsoft) and the enabler (Nvidia) have surged. Expedia, Booking, and MakeMyTrip have roughly 2.5x’d since launch, while Tripadvisor and eDreams are now in the red.

8. When founders watch from the sidelines

Chip Wilson, founder of Lululemon, no longer runs the company, but in a full-page ad in the Wall Street Journal, he laid out precisely what he thinks is going wrong and painted a vision of where the brand could go. Agree with him or not, it’s a sharp contrast to the polite silence most ex-founders keep. Maybe more should speak up when the companies they built start going off track. This ad had more strategic clarity than any media or investor analysis I’ve seen on Lululemon.

9. Low-Cost flights and high-impact memes

Europe’s top low-cost airline keeps winning on social media by staying irreverent and refusing to take itself too seriously.

10. Flygaroo is live on Kickstarter (with a Travel Tech Essentialist perk)

Back in August, I shared the story behind Flygaroo, a vest built to avoid the costly baggage fees by turning your torso into extra carry-on space. After flying 40+ low-cost routes, founder Nicolas Gutierrez de Esteban decided there had to be a smarter way to travel light without paying high fees.

Now it’s live on Kickstarter and already fully funded, but they’ve added a special Travel Tech Essentialist–only reward tier with €60 off retail. Same deal they offered in the first 24 hours (which sold out fast), now unlocked again for us.

(Waiting to see if Ryanair’s social team has thoughts on this one.)

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Special thanks to the Airobot for sponsoring this edition of the newsletter:

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1. Altman on travel bookings: they’ll do it, eventually

At the Progress Conference last week, Sam Altman responded to a story from the interviewer, who mentioned that during a recent trip, nearly every hotel and restaurant he picked was discovered through GPT-5. None of those bookings went through OpenAI, and the company earned nothing from it.

Altman acknowledged the gap, but didn’t seem bothered. ChatGPT gives recommendations without bias, he said, and that’s what builds trust. If it ever took money to promote a worse hotel over a better one, that trust would evaporate. But if it recommends the best option and takes a flat commission without that influencing the result, that feels to him like a sustainable model.

He expects hotel and travel commissions to shrink. Once people ask their AI to find the best hotel, the agent may complete the booking through the service that charges the lowest fee. According to Altman, this dynamic will make “margins go dramatically down on most goods and services, including things hotel bookings”

OpenAI still plans to support bookings at some point, but Altman doesn’t see it as a major business priority. It’s not where OpenAI will make most of its money, and it’s not the point of the company. His primary focus is on breakthroughs such as curing diseases, unlocking new scientific discoveries, or building abundant clean energy. In that view, travel is just one of many real-world use cases they’ll likely end up supporting simply because it makes ChatGPT more useful in everyday life. Podcast - Sam Altman on Trust, Persuasion and the Future of AI

“The way to monetize the world’s smartest model is certainly not hotel booking... I want to discover new science and figure out a way to monetize that” - Sam Altman

2. Useful opposites

These less common words work as counterweights to the more popular ones, and often make more sense. A way to think more positively about work, stress, success, and other people.

• Pronoia: Opposite of paranoia. When you believe the world is conspiring in your favor

• JOMO: Opposite of FOMO. The joy of missing out

• Eustress: Opposite of distress. Helpful stress that sharpens and motivates

• Mitfreude: Opposite of schadenfreude. Taking joy in someone else’s joy (German)

• Flâneur: Opposite of grinding. French term for someone who strolls and observes, creatively present

• Kintsugi: Opposite of perfectionism. Japanese art of repairing broken pottery with gold, making the flaw part of the story

• Lagom: Opposite of excess. Swedish idea of “just enough,” not too little or too much

• Ubuntu: Opposite of individualism. African philosophy meaning “I am because we are”

• Ikigai: Opposite of productivity for productivity’s sake. Japanese concept of purpose, or reason for being

3. Broken, but useful

Some things still work even when they stop working.

An escalator that’s out of order still works as stairs. A powered toothbrush is still a toothbrush. An electric bicycle with a dead battery is still a bike. They fail in a way that leaves their core function intact.

This is a useful lens in product design: not just “what happens when it works,” but “what happens when it doesn’t.” What parts still work? What do people reach for anyway? What fallback becomes the default?

You see it in travel too. A maps app with offline mode still shows your cached route when you lose signal. A hotel key card with the room number printed on it helps when you forget which room is yours. An itinerary in your email still loads offline.

It also shows up in customer service. When flights get cancelled, or a partner goes bust, or a traveler is stranded and stressed—those are the moments that matter. At eDreams, some of our most loyal customers came from travel nightmares, simply because we showed up and had their back.

Designing for failure earns trust. When your product still works in the worst moments (dead battery, no signal, unfamiliar city, high stress…), people remember. That resilience builds more loyalty than a hundred perfect-condition experiences.

4. The Benefits of bubbles

Everyone’s calling it a bubble. And they’re probably right. The hype around AI is overblown in places, money is flowing too fast in others, and a lot of ventures chasing it will fail. Ben Thompson’s The Benefits of Bubbles offers a timely and thoughtful counterpoint to the AI-bubble cynicism that’s in vogue right now. Thompson makes the case that bubbles, when they’re about transformative technologies, can be deeply productive. They overbuild capacity, fuel invention, install the physical and cognitive infrastructure and create the mechanisms that help an entire ecosystem grow. You saw it with railroads, fiber optic cables, and the early internet. Most of those bets didn’t pay off for the investors, but they did for society. And let’s be honest…most of the people yelling “bubble!” aren’t the ones risking their own money. They (we) are the ones who’ll end up reaping the benefits: faster tools, cheaper compute, better infrastructure, and a front-row seat to the fireworks, all without putting a cent on the line.

Thompson builds on Carlota Perez’s idea (Technological Revolutions and Financial Capital) of the “installation phase” of a technology, when money-losing investments are necessary to lay the groundwork for a more productive future. He also draws from “Boom” by Byrne Hobart and Tobias Huber, who refer to these as “inflection bubbles”: the kind that spur foundational change across entire industries.

This AI cycle may follow a similar arc. Even if some investments fail, they’re helping to build capacity in chips, energy, talent, and ambition. They’re also unlocking hard-to-justify projects that might not happen without the FOMO and froth of a bubble. That includes deep infrastructure like fabs (the places where the chips are made) and power generation, as well as totally new chip architectures and AI-native startups pushing in every direction.

As Thompson writes, “Optimism can be a self-fulfilling prophecy.” You don’t get enduring change without some speculative fever along the way. Read + Ben Thompson

5. The anti-trend moat

The bigger the trend, the more leverage in going the other way. Taking the other end of a dominant shift can open up space others have stopped paying attention to, often with less competition and more loyalty. In the constant stream of AI tools, virtual products, and automation hacks, Jonathan Courtney and Greg Isenberg (on the Startup Ideas podcast) talk about how in-person experiences are becoming a real advantage again. They don’t scale easily, and they take more effort. That’s exactly what makes them stand out. People remember them, trust them, and talk about them later.

Jonathan shares examples from his own business, such as launching a $ 15,000 in-person certification, renting out an Italian village for a retreat, and running high-ticket summer camps with no recordings, no livestream, and no virtual pass. Just real people in a room. He explains how that constraint became the hook, offering a clear, hard-to-copy offer in a format that people miss.

In travel/hospitality, layering real-world presence into the offer, even if the core product is online, could lead to good surprises.

6. The impact of Google AI Overviews

New data from Seer Interactive shows sharp declines in both organic and paid click-through rates (CTR) on queries that trigger an AI Overview (AIO). Organic CTRs are down 61%, and paid CTRs are down 68% compared to a year ago. Even queries without AI Overviews have CTRs dropping between 25% and 41%.

Fewer people are clicking, and there is also a shift in how people search. More are getting answers directly from the AI box or skipping Google altogether for ChatGPT, Reddit, or trusted brands.

What’s working now is being cited in the AI Overview itself. Brands that were cited saw 91% higher paid CTRs and 35% higher organic CTRs than those that weren’t. The new moat is being cited, not just ranked.

(Methodology: 25 million organic impressions, 1 million paid, across 15 months and 42 companies.)

7. How to live a miserable life

Most life advice tries to tell you what to do. This flips it. Sam Parr (from My First Million) lays out 5 ways to live a miserable life, and what happens when you do the opposite

Parr’s framing is clever: don’t chase happiness. Just stop doing the things that make you miserable.

8. What airports might feel like by 2040

Airports have barely changed in decades; McKinsey’s “Next Normal” report imagines what airports could look like by 2040. Some takeaways:

• Facial recognition replaces IDs and boarding passes. Walk through check-in and security

• Personalized signage point you to your gate, in your language, with real-time updates.

• Flying taxis. First-mile transportation might be a drone ride from your backyard straight to the runway.

• Robots handling luggage, refueling, and runway ops behind the scenes, helping planes take off on time.

The airport of the future is going to be a place where people want to meet, even if they’re not flying — Vik Krishnan

9. Brand building starts with a human voice

Avi Meir, founder and CEO of Perk (formerly TravelPerk), was one of the most followed (and the most engaging) travel tech voices on LinkedIn, according to my analysis in my previous newsletter.

His latest post is a perfect example of why: it sounds unmistakably like a human. Not a press release, not an LLM, no posturing, no performative virtue. Just Avi…clear, direct, and human. That’s what makes him so effective. Personal authenticity also reinforces the values of the company he leads. When a founder/executive shows up as a real person, it strengthens the corporate brand too. People follow people. And they remember how you made them feel.

10. US startups are pulling ahead

This chart from a16z (via Stripe data) shows just how much faster US startups are growing than their European and UK counterparts; nearly 1400% since 2020, compared to ~600% for the EU and ~500% for the UK. Even when you exclude AI startups, US companies still lead by a wide margin. Around 2024, the AI-led growth accelerated.

Stripe’s Patrick Collison attributes this gap to faster tech adoption in the US, less regulation, a larger domestic market, and a stronger consumer appetite for new technology. Whatever the mix, it’s delivering results. US startups are building faster, scaling harder, and taking bigger swings. Read + a16z

Travel Tech Essentialist Job Board

→ Explore all 1479 open roles on the Travel Tech Essentialist Job Board now.

• Viator | Vice President of Distribution Partnerships | Multiple Locations

• Acai Travel | Founding Marketing Lead | New York City

• Expedia | Data Scientist II - Revenue Optimization Strategy | Madrid

📩 For monthly updates on the latest roles, subscribe to the Travel Tech Jobs newsletter

Raising a round?

If you are a startup looking to raise a round (from pre-seed to Series D), I can help (for free). Travel Investor Network is a private platform where I recommend innovative travel startups to investors and innovators. If you’re interested, please start by completing this form.

If you like Travel Tech Essentialist, please consider sharing it with your friends or colleagues. If you’re not yet subscribed, join us here:

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And, as always, thanks for trusting me with your inbox.

Mauricio Prieto

Special thanks to Zoftify for sponsoring this edition of the newsletter:

Looking for a digital partner who truly understands travel? Zoftify helps tour operators, OTAs, and travel startups modernize platforms, optimize booking flows, and craft beautiful, high-converting digital products — built by a 100% travel-specialized team.

If you’re attending WTM in London, book a meeting or stop by stand S2-209 to connect. And don’t miss Tourseta, a flagship platform for multi-day tour operators.

1. Designing travel products people love

Many of you responded positively to Nesrine Changuel’s Product Delight framework when I mentioned it in an earlier newsletter. So I asked Nesrine if she’d write a guest post on how it applies to travel, and she kindly agreed. In “How to Build Travel Experiences People Love,” she shows how travel products can transcend utility to create a genuine emotional impact. Well worth a read. Thanks again to Nesrine for the contribution.

2. Who’s worth following in Travel Tech?

In the last newsletter, I included a quick survey asking readers to name the people they consistently find valuable for travel tech insights on LinkedIn or X. No brands, just individuals.

From 60 responses, 133 names were mentioned*. Christian Watts was the clear standout, mentioned by 7 different respondents. Others mentioned three or more times: Peter Syme (5); Brennen Bliss, Lennart Dobravsky, Rafat Ali, and Timothy O’Neil-Dunne (4 each); and Avi Meir, Gilad Berenstein, JoseLuis Vilar, and Martin Soler (3 each).

The conversation in travel tech still feels broad, with many voices contributing rather than one overwhelming leader. The sample size is small, so it’s hard to draw broad conclusions, but it gives a glimpse into who’s moving the needle for this audience.

*Note: I’ve excluded myself (Mauricio Prieto) from the analysis. Since the survey was shared on this newsletter and on my own social channels, the results are skewed.

3. How do these voices engage on LinkedIn?

I analyzed LinkedIn engagement for the individuals who were mentioned 3+ times in the survey, along with two benchmarks: Phocuswire and Skift, two leading travel media brands.

The stats are based on a sample of each account’s last 30–50 posts. The table includes three metrics: number of LinkedIn followers, median engagement (likes + comments) per post, and engagement per 1,000 followers to account for differences in audience size.

A few quick takeaways:

• Martin Soler and Lennart Dobravsky lead in engagement relative to their follower base.

• Christian Watts, the most mentioned in the survey, also performs strongly both in absolute and relative engagement.

• People seem to be paying more attention to individuals than to brands, with a growing premium on authenticity and personal perspective. The two media brands rank lowest in both raw and relative engagement. Despite having nearly half a million followers, Skift ranks at the bottom in both total and relative engagement

• The most-followed aren’t the most engaging. And some under-the-radar voices are clearly resonating.

4. Kayak’s $457M writedown

In a recent Skift interview/article, Kayak CEO Steve Hafner attributed a $457 million writedown on the brand to shrinking SEO traffic. He’s not wrong that AI summaries and paid placements are reshaping how people find travel options.

Over the past year, Google has pushed its own AI-driven answer formats in response to the ChatGPTs of the world. So Google’s answers to consumer queries are often self-contained and don’t require a click to a third party, such as Kayak or Expedia. The free links have lower visibility than paid links, so companies such as Kayak have to spend more to acquire customers. — Skift

Fair. But the deeper issue is platform dependency.

It’s like a pop-up shop blaming the department store for a drop in foot traffic. If your business depends entirely on someone else bringing people to the door, you’re not in control; they are.

Kayak’s issues are not about Google getting greedy. It’s facing pressure because the discovery it relied on was never really its own. When your visibility depends on someone else’s platform, your margins are always at risk.

5. Cheat sheet for emotional travel marketing

Expedia’s Science of Wanderlust study used emotion-tracking, eye-tracking, and surveys to understand what kind of content actually gets people to book. It’s a marketing piece, but there’s solid insight here for anyone building travel inspiration, media, or AI-driven tools.

Video stood out as the most effective format, influencing 71% of travelers, compared to just 24% for static images. But effectiveness didn’t come from polish or production value. The videos that worked best are grounded in emotional, human storytelling, with a clear narrative, steady pacing, and a sense of authenticity. People respond to content that feels honest, not overly produced or AI-generated. Representation also matters: 34% said they trusted content more when they saw themselves reflected in it. And while travelers are open to AI-assisted content, most don’t trust AI-generated influencers or travel advice. There’s also a generational divide. Gen Z and Millennials tend to engage more emotionally and socially. Older travelers still value brand trust.

What moves us is less about where we could go, and more about how it might feel to be there. Emotion and authenticity still carry more weight than anything an algorithm can optimize for.

6. A better way to do performance reviews

Lenny Rachitsky shares the system he used at Airbnb, covering everything from how to prepare for the conversation to how to structure the review itself, and what follow-up looks like, so that people actually improve. It includes the templates he used, questions to ask, and mistakes to avoid. It’s especially useful if you don’t have a full HR team but still want your reviews to be thoughtful, honest, and helpful. Read + First Round. And here’s the template you can download and use.

7. Airbnb adds social features to Experiences

Airbnb just introduced new social tools for Experiences. Guests can now see who else is going, message each other, and stay connected after the trip. It’s framed as a way to build community, but it also opens the door to something more.

Mathias Coudert made the point that this starts to look a lot like the foundation of a dating app: shared activity, low-stakes context, real-life interaction. It’s the same logic behind joining a run club or pottery class. You meet people doing something you already enjoy. Airbnb might not market it this way, but the mechanics are already in motion.

8. The travel startups that YC has backed

YC has backed 24 travel, tourism and leisure startups since 2007. Here’s a quick breakdown:

• One (Airbnb) has gone public. A handful have been acquired (Flightcaster, Solve, Momence, Songkick, Hipmunk, VacayHero, Vayable). Most are still active and independently operating.

• Includes vacation rentals, local experiences, AI-powered travel search, loyalty tools, group booking, airport logistics, and fractional home ownership.

• 17 of the 24 are US-based. Four are based in the UK (Let’s Do This, Shoobs, Tab, Songkick), two in Mexico (Shuttle Central, Ancana), and one in Germany (Airhelp)

9. Advertising for emotional connection

10. Job Board: Top 10 roles and locations

Here’s a look at the top 10 job functions and locations from applications on the Travel Tech Essentialist Job Board over the past two months.

Travel Tech Essentialist Job Board

→ Explore all 1479 open roles on the Travel Tech Essentialist Job Board now.

• TravelPerk | Sponsorships & Brand Partnerships Manager | Barcelona; London

• Fora | General Manager - Mexico | New York City | $150k - $180k + Equity

• Airbnb | Senior Marketing Lead, Experiences & Services | USA | $196k - $245k + Equity

📩 For monthly updates on the latest roles, subscribe to the Travel Tech Jobs newsletter

Raising a round?

If you are a startup looking to raise a round (from pre-seed to Series D), I can help (for free). Travel Investor Network is a private platform where I recommend innovative travel startups to investors and innovators. If you’re interested, please start by completing this form.

If you like Travel Tech Essentialist, please consider sharing it with your friends or colleagues. If you’re not yet subscribed, join us here:

Subscribe now

And, as always, thanks for trusting me with your inbox.

Mauricio Prieto

This is a guest contribution by Nesrine Changuel, product coach, speaker, and author of Product Delight. She’s spent over a decade in product leadership roles at Google, Spotify, and Microsoft, and now helps teams build more thoughtful, human-centered products.

After seeing the significant interest her Product Delight framework generated in past issues of this newsletter, I reached out to invite her to explore how it applies to the travel industry. I’m thankful she agreed.

In this piece, Nesrine examines how travel products can transcend their utilitarian purpose to create emotionally charged, memorable experiences.

Turning Journeys into Emotional Experiences

Travel is one of the richest grounds for product delight. It is full of emotion: anticipation, excitement, stress, and discovery. Yet, most travel products focus almost entirely on functionality, including booking, check-in, itineraries, and support. They help us move, but they rarely move us.

I created the Product Delight Model to help teams design for emotion as well as for utility. It focuses on three key elements: Functional Motivators, Emotional Motivators, and Deep Delight, the moment where both come together.

In my book, Product Delight, I emphasize that great products honor both functional and emotional motivators. Functional motivators are about solving clear, practical needs such as booking a flight or checking a gate. Emotional motivators capture how people want to feel while using the product: calm instead of anxious, cared for instead of ignored, excited instead of bored.

This model has guided my thinking across industries, but it feels especially relevant to travel, where emotion is the heartbeat of every experience.

The Three Types of Delight

Not all delight is the same. The Product Delight Model distinguishes three levels of experience: Low Delight, Surface Delight, and Deep Delight.

Low Delight occurs when a product solves a functional problem effectively but without emotional resonance. It’s useful and necessary, but not memorable. In travel, this could be a smooth booking flow or accurate flight updates. These moments matter because they build trust, the foundation on which deeper emotions grow.

Surface Delight focuses on small, human touches that create warmth or joy. Imagine a hotel app greeting you by name or an airline celebrating your birthday with bonus miles.

These gestures may not change functionality, but they remind users that there are humans behind the product.

Deep Delight is where function and emotion meet. An example? Hilton transformed the hotel stay experience with Digital Key, available through the Hilton Honors app. Guests can check in from their phone, choose their room, and use their smartphone or smartwatch to unlock it, no waiting at the front desk, no keycards to lose.

On the surface, it’s a convenient functional feature. But the real delight comes from how seamless and personal the experience feels. After a long day of travel, guests can walk straight to their room, tap their phone, and instantly feel at home. It’s smooth, predictable, and empowering; you feel like the hotel already knows what you need.

Hilton took this even further with Connected Room, which allows guests to personalize their environment directly from the app: adjusting lighting, temperature, or TV preferences even before arriving. The next time they stay, the room “remembers” their choices.

The Three Pillars of Delight

Delivering delight isn’t about random surprises. It begins with understanding what truly makes an experience great. The three pillars of delight, addressing pain points, anticipating needs, and exceeding expectations, form the foundation of the Product Delight Model.

Addressing Pain Points

Users often turn to products because they want to solve a specific problem or eliminate a source of frustration. Delight happens when a product removes that friction and does so seamlessly.

Think about the moment you’re rushing through an unfamiliar airport, trying to find your gate, and the app instantly guides you to the correct terminal. That quick sense of calm that replaces stress is delight. Great travel products earn trust by quietly resolving problems without drawing attention to themselves.

Apple Wallet’s boarding pass is a perfect example of this principle. By anticipating the traveler’s context and surfacing what they need exactly when they need it, Apple turns what used to be a stressful task into a moment of calm and confidence. It’s a powerful demonstration of product delight through frictionless design.

Anticipating Needs

Not every need stems from frustration. Many are subtle and only revealed when the right solution appears. Truly delightful products anticipate these needs before users express them.

Revolut’s eSIM is a strong example. Frequent travelers often struggle to stay connected abroad, juggling SIM cards and worrying about roaming charges. Revolut anticipated this pain point by offering an eSIM that users can activate directly within the app, choosing data packages for their destination.

The result goes far beyond convenience. Travelers feel relaxed and in control. Revolut extends this mindset to security, with location-based protection, instant card freezing, and virtual cards for online purchases. These features may look functional, but the real impact is emotional: they create peace of mind.

Even small touches like Vaults, Revolut’s automated savings feature, follow this same principle. They anticipate a user’s intent to save and make it effortless. Anticipating needs means observing behaviors, listening between the lines, and building features that make people feel understood.

Exceeding Expectations

Meeting user needs is essential, but true delight happens when a product goes further and delivers more than expected, in a way that feels personal and human.

I experienced this recently with Uber. I booked a ride to the train station, but the driver canceled a few minutes later. Frustrated, I flagged down a taxi instead. Later, I noticed I had been charged for the canceled ride. Expecting a long, tedious process, I opened the app to request a refund. To my surprise, it took only two simple steps, and the refund arrived instantly with a short, polite message of apology.

This was an obvious example of exceeding expectations. I thought I’d have to submit a case and wait a few days for a response. However, the process was much faster and smoother than I expected.

Designing for Deep Delight in Travel

Creating delightful travel products isn’t about flashy animations or motivational quotes. It starts with understanding human motivators and the emotional rhythm of travel.

Map the traveler’s journey: the anticipation before departure, the anxiety at security, the fatigue of waiting, and the joy of arrival. Find the moments where functionality and emotion can meet.

Start by getting the basics right. That’s your foundation of trust. Then, identify a few key touchpoints where you can surprise, reassure, or celebrate the traveler. Finally, make it effortless. The most delightful products often feel invisible. When technology fades into the background and emotion takes the lead, that’s where true delight lives.

Looking Ahead

As travel continues to evolve, delight will become one of its strongest differentiators. Whether the journey is physical or digital, people will never forget how a product made them feel: calm, cared for, confident, or inspired.

Delight isn’t about luxury. It’s about empathy. It’s about designing for humans who experience both stress and wonder, who want to be guided without being controlled, and who crave reassurance in moments of uncertainty.

When your boarding pass appears before you even think about it, that’s more than good design. That’s care, turned into experience.

And that is the essence of the Product Delight Model, as I explore in my book Product Delight: transforming practical interactions into emotional memories that people love to relive.

Special thanks to Propellic for sponsoring this edition of the newsletter:

While you’re still optimizing for keywords, Google’s AI is rewriting the rules of travel search. Our NavLog readers are ahead of the curve with Google’s AI search surfaces. Don’t get caught playing catch-up when your competitors are already adapting. Get the travel marketing intelligence that matters. → Join 1,500+ travel marketers.

1. Where will value accrue and decline in an AI-generated world?

In his recent post, “The AI Slop Arbitrage,” Greg Isenberg argues that as AI makes creation abundant, the value shifts to what can’t be easily generated. He maps out where value will accrue and where it will decline in this new landscape.

Some examples of where value will increase:

• The value of trusted brands, recognized experts, taste, and curation increases because reputation, credibility, and knowing what to ignore can’t be automated.

• Unique insights and “un-Googleable” knowledge gain value, since AI can easily replicate what’s already online but can’t fake domain expertise earned over time.

• Proprietary data and community-built products create moats because when everyone has access to the same public training data, the edge is in what nobody else can see.

• Real-world distribution, retail shelves, and in-person relationships become key differentiators because they can’t be automated.

On the flip side, Isenberg suggests that some areas will see their value decline, such as:

• Generic AI wrappers because simply wrapping ChatGPT in a UI is mostly decoration.

• Average content because AI can now create it in abundance.

• Audiences without trust because a million disengaged (or acquired) followers are worth less than a hundred loyal ones.

• Faceless brands, because people buy from people, and when everything is generated, humanity becomes the premium.

In an AI-generated world, the most valuable things will be the hardest to automate or fake. Differentiation will come from authenticity, curation, real-world presence, and above all, trust and humanity.

2. The shared language of delight

In my last newsletter, I wrote about Nesrine Changuel’s product framework for delight. Last week, she published a post that draws a connection between product design and hospitality, specifically, the story behind Will Guidara’s Unreasonable Hospitality and how Eleven Madison Park became the best restaurant in the world.

She advances nine shared principles between dining and digital products, from removing friction to exceeding expectations to energizing the teams behind the work. Read + When Hospitality Meets Product

Functionality creates trust, but it doesn’t create love. Whether it’s the way a waiter remembers your name or how Google Photos quietly curates your best memories into a story, connection comes from the human layer around functionality. Delight begins where functionality ends, when products and experiences start speaking to our emotions, not just our needs. — Nesrine Changuel

3. What the data says about reaching $1M ARR (and beyond)

Kyle Poyar teamed up with ChartMogul to analyze growth data from 6,500+ SaaS companies. Just 2% of these startups reach $25 million in ARR within 10 years. Even hitting $1 million ARR takes longer than most founders might expect: 2 to 5 years after monetization. Only 3% get there in under a year.

The piece includes useful benchmarks but is honest about the caveats. These are companies serious enough to track SaaS metrics, which likely skew the data a bit more optimistically. And the dataset starts with first revenue, not founding… so it doesn’t capture the quiet years before launch or the startups that shut down early.

AI-native startups are 3x more likely to reach $1 million ARR in 6 months, and 8x more likely to reach $10 million ARR within a year. Vertical SaaS and enterprise startups grow more slowly: only about 1.2–1.7% reach $1M ARR in 6 months, and fewer than 0.1% make it to $10M ARR in a year.

The data also shows geography still matters, but less than it used to. Bay Area startups are about 70% more likely to hit $1M ARR within three years, yet companies in locations like France, Canada, or New York often show more staying power. Read + The Odds of Making It.

4. Simulating demand

New research shared by Ethan Mollick shows that you can replicate real purchase intent with 90% accuracy by prompting an off-the-shelf LLM to act like a customer with a demographic profile. Show it a product image, ask for a free-text reaction, and compare the response to reference statements on a 1–5 scale using semantic similarity. The researchers tested three methods and found that this semantic approach was the most accurate, required no fine-tuning, and outperformed classic machine learning models.

This could make early demand testing much faster and cheaper. Still, real conversations remain essential for understanding nuance, emotion, and context. AI is a valuable complement, but not a substitute for that kind of learning.

5. Visitor dynamics among Spain’s top travel players

This data comes from a special partnership between Travel Tech Essentialist and Directo, one of the most-installed browser extensions in the global travel category. Directo uses AI to help travel brands capture demand and convert browsing intent into bookings.

A few highlights from the dataset (each stat is circled in the chart for quick reference)

• Booking vs Airbnb: 79% of Airbnb visitors in September also visited Booking.com, while only 24% of Booking.com visitors also visited Airbnb in September.

• eDreams vs Skyscanner: 53% of eDreams visitors also visited Skyscanner, but only 23% of Skyscanner visitors visited eDreams.

• 72% of Kiwi visitors also visited Skyscanner…the highest cross-visit share to Skyscanner of any player. But only 7% of Skyscanner users visited Kiwi.

• eDreams and Skyscanner are the only major players where fewer than 75% of users also visited Booking.com. Still high, at 71% and 70%, but lower than others.

• Vrbo (65%) and Hostelworld (49%) have the highest share of users also visiting Airbnb.

• 36% of Kiwi users visited eDreams; the highest share for any competitor. But only 8% of eDreams users went to Kiwi.

Data limitations: i) The dataset is primarily desktop-based, since Directo operates via browser extension. Mobile behavior is thus underrepresented. ii) These insights reflect the behavior of Directo’s user base, which may not fully represent all traveler segments.

6. Revolut integrates travel into the core product

Revolut just acquired Swifty, a Lufthansa Innovation Hub spinout that built a conversational AI travel agent. The product handles the whole booking process, from search to invoicing, through a chat interface. The team is joining Revolut to help expand its loyalty and lifestyle products by combining financial guidance with automated action across spending, travel, and rewards.

In my last newsletter, I pointed to Revolut’s eSIM as a clear example of how delight comes from anticipating real pain. Swifty brings that same approach, but across the whole booking stack. It’s also another signal that fintechs with high user engagement are moving into lifestyle automation and shifting from helpful content to helpful action. Capital One’s work with Hopper is another good example of integrating travel directly into the credit card experience. These companies already own the payment moment, and they’re coming for everything around it.

7. Showing traction before you have it

In this LinkedIn post, Andrew Chen discusses a catch-22 many startups face: needing traction to raise money, but needing money to gain traction. He highlights tactics like launch videos, waitlists, and “building in public” that can help demonstrate momentum before achieving “real” metrics like revenue. The key is finding creative ways to validate interest and bridge the gap to more substantive traction. While not as solid as revenue, these tactics can generate buzz, engage potential customers, and prove to investors that you’re on the right track.

8. The ultra-rich are giving up on luxury assets

The ultra-wealthy are losing interest in traditional luxury assets, according to this article in The Economist. Prices for Bordeaux first growths have dropped 20%, and second-hand Rolexes are down 30%. Even prime real estate in global cities is stagnating. But as The Economist reports, the cost of ultra-luxury services keeps rising. A table at a three-star Michelin restaurant, a room at an iconic hotel like Paris’s Le Bristol, courtside seats at the Super Bowl, and front row at Wimbledon are all becoming more exclusive and expensive.

The dynamics driving this shift align with Thorstein Veblen’s theory of luxury: scarcity and rivalrousness are what make something truly luxurious. In an era of abundance, it’s the unique, unrepeatable experiences that are most valued.

9. Travel tech voices worth following

Quick ask: Who are the individuals you follow/trust on LinkedIn or X for travel tech insights? Not media brands, just people. Founders, execs, operators, analysts, researchers. People who consistently share useful ideas or help you think more clearly about where travel is headed.

Please answer directly (and anonymously) on this Google Form. If you’ve already voted from my LinkedIn or Twitter post, I have your votes, no need to vote again. And please, no voting for yourself :)

Would love to know who’s on your radar. I’ll include the results in a future edition so others can follow and learn from them too.

10. A small test that reveals a lot in hiring

Trent Innes, former MD at Xero and now CGO at SiteMinder, uses a simple rule in interviews: if a candidate doesn’t take their coffee cup back to the kitchen, they don’t get hired, regardless of their credentials. Read +

These small behaviors speak volumes. They signal a specific mindset, respect, and cultural awareness. Often more powerfully than a résumé.

Travel Tech Essentialist Job Board

→ Explore all 1501 open roles on the Travel Tech Essentialist Job Board now.

• Expedia | Director Global Markets - Mexico | Mexico City

• TravelPerk | Product Design Manager | London

• Airbnb | Data Scientist - CRM | USA | $194k - $240k / year + Equity

• WeRoad | Head of Sales and Customer Experience | Milan

📩 For monthly updates on the latest roles, subscribe to the Travel Tech Jobs newsletter

Raising a round?

If you are a startup looking to raise a round (from pre-seed to Series D), I can help (for free). Travel Investor Network is a private platform where I recommend innovative travel startups to investors and innovators. If you’re interested, please start by completing this form.

If you like Travel Tech Essentialist, please consider sharing it with your friends or colleagues. If you’re not yet subscribed, join us here:

Tools and Tactics, No Fluff

And, as always, thanks for trusting me with your inbox.

Mauricio Prieto