Some of the stories in this newsletter are about disparity. Many predictions for Google didn’t come true. Founders tend to lead with conviction, while hired leaders tend to proceed with caution. Most products are not designed for the most valuable travelers. Airbnb’s official loyalty score doesn’t match its NPS.
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Lori Timony, Christian Watts, and Bruce Rosard were kind enough to invite me to their event Experience it! Podcast conversation starts with my latest newsletter The Optimist’s Edge.
The core argument is that optimism is a timing advantage. Optimists take action before things become obvious but after they are in the right direction. They invest before the data looks good, and that’s their advantage.
But optimism used in the wrong places can kill a company. Patrick Collison of Stripe said it best: Macro optimism, micro pessimism. Be optimistic about long-term direction, be pessimistic and ruthless about execution. Founders who hit the runway are often optimistic about both. Those who never build are pessimistic about both. The only combination that works is macro optimism + micro pessimism.
In tours and activities this is more important than in other areas of tourism. Flights are logistics, but experiences are products built on belief and emotion. If you’re not a macro-optimist and don’t believe in humans’ inherent need to travel and explore, there’s no reason to build in this space. If you do, the reasons for macro optimism are obvious. From a customer’s perspective, if they don’t feel optimistic, demand disappears faster, but when optimism returns, this category grows faster than any other. This emotional need also makes the category resilient to disruption from artificial intelligence. If AI continues to automate digital execution, the most valuable companies in the travel industry may be those that get us to use less screens. Physical presence is the point.
“Is this the end of Google search?” has been a recurring headline. They’re snapshots of what analysts and the media think about the present, but they’re still mere musings and have a poor track record of guiding the future. Pieces like these are useful for entertainment and context, but founders shouldn’t rely too heavily on them when making long-term bets.
How is Google progressing (Q1 2026)…
→ Google search advertising revenue increased 19% year-on-year to $60.4 billion
→ Total revenue increased 22% year-over-year, driven primarily by search advertising and YouTube advertising
→ AI capabilities drive search query volume to ‘all-time high’ more Use of Google Search.
→ Google continues to hold about 90% of the global search market, processing trillions of searches every year.
→ Shares are up 330% since The Economist predicted the end of Google’s lucrative business.
It turns out that when disruption comes, established companies like Google rarely stand still like a deer in the headlights.
Over multiple cycles, the “founder effect” manifests itself in hard data. Bain’s data The study found that since 2015, total shareholder returns for founder-led companies have been 2.1 times higher than their non-founder peers, with technology companies rising to 2.6 times. data Data through early 2026 shows that companies whose founders have recently departed have a five-year average annual return of 6.9%, compared with 15.4% for companies still led by their founders.
Most CEOs are trained in risk management, but founders serve as chief risk officers. They are optimistic about where the world is going but ruthless about execution. In an era of disruption, the gap widens. Google is the most obvious recent example. After years of being viewed as a laggard in the field of artificial intelligence, co-founder Sergey Brin returned to the forefront of technology in 2023. The culture shifted and the results followed, with Google’s stock price growing 210% since then.
The founder’s job is to inject risk into the business. It’s filled with new ideas, things that seem hard to do, ideas that no one dares to try, bets that only those who started the damn thing are willing to make. – Jason Fried, founder and CEO of 37signals (makers of Basecamp and HEY).
Brian Chesky’s First Quarter Earnings Conference Call For Airbnb, it’s full of concrete AI thinking.
On the internal front, 60% of Airbnb’s code is now written by artificial intelligence, roughly double the industry average. Chesky concluded that the company needed to reorganize around speed. In his view, hands-off managers running teams remotely no longer have much of a role to play. Design managers and engineering managers are getting back to writing code.
On the customer side, Airbnb deliberately launched AI in bottom-of-funnel customer service because Chesky believed that was the hardest problem: no room for hallucinations, multilingual, high-stakes, real-time decision-making. More than 40% of support issues are now resolved without a human agent, up from one-third last quarter. Cost per booking fell 10% year-on-year.
He explains why chatbots currently built are not suitable for travel or e-commerce. Four reasons: too much text in one category, which is basically photo-forward; no direct manipulation of filters or sliders; large-scale comparisons within threads become impossible; most bookings involve multiple guests, and chatbots are built for one person. He concluded that no one has yet explored the application of artificial intelligence in travel.
a new study Reviewed 1,357 Gemini citations from 156 hotel queries in Tokyo. The query frame determines whether the AI refers to the OTA or the hotel’s own website.
“Budget hotels in Shinjuku“OTA citations are returned 69% of the time.”Shinjuku hotel with local charm” dropped to 44%. After rephrasing the same question, there was a 25-point swing.
Content depth is more important than branding or technical polish. Hotel K5 has high ratings and appropriate architectural markings. Gemini mentions this, but citing Expedia, not K5’s own website. Kadoya Hotel has no schema markup or SEO, but its 33-question FAQ and 13 nearby attractions guides directly reference Kadoya’s own website.
This study is for Tokyo and Gemini, so the exact numbers are considered directional. But the underlying logic is that AI searches will cite the person who can best answer the question. For price inquiries, it’s still OTA. For the rest, hotels with deep content can compete.
(Thanks to Gene Quinn for pointing this paper to me)
Titled Recent eDreams press releases: “eDreams ODIGEO further expands the Agentic AI ecosystem by integrating conversational planning and instant booking fulfillment.”
Hidden in the jargon is an in-app travel planner, ChatGPT integration and voice AI that can now handle 90% of call traffic in five languages, with a 33% reduction in call transfers and a 15% reduction in resolution time, with the entire deployment completed in a matter of weeks. good!
Headlines are the opposite of clickbait. It actively prevents people from reading results worth reading.
This table shows the 25 countries with the highest outbound tourism spending in 2024, ranked by growth since 2022.
China and the United States basically have $250 billion each. No other country comes close. Germany and the UK ranked third and fourth with US$120 billion and US$119 billion respectively.
Seven of the top ten fastest-growing markets in this group are in Asia, and all seven have more than doubled.
Every travel brand wants to attract Gen Z, but the travelers who spend the most money are twice their age. Baby boomers spend an average of $8,242 per trip, more than double what Gen Z spends ($3,753). People over the age of 50 spend more than $236 billion in annual U.S. leisure travel spending. By 2030, the number of people aged 60 and over worldwide will reach 1.4 billion, accounting for more than one-third of all international travel. By 2032, the silver tourism market is expected to reach US$1.4 trillion. This segment still primarily books via desktop, still uses travel agents, plans for months, and has an 8% AI adoption rate for travel planning (94% of those who have tried it find it helpful). People who have money, time and are open to the tools that work for them. There seems to be an opportunity to build products specifically for them.
Compare Breaking down NPS by age, the pattern is consistent across Booking.com, Expedia, and Airbnb; satisfaction declines as travelers age, with detractors dominating starting in their 40s. Combined with the senior travel spending data above, the chart below shows that the most valuable travelers in the market are also the least satisfied with existing products.
Carabello Benchmark loyalty programs The five largest OTAs use a framework built around three pillars: access (exclusive inventory and attribution), control (pricing transparency and flexibility), and convenience (booking ease and digital experience).
Across all five plans, convenience is well covered and control gets better and better. Access (exclusive inventory, a sense of belonging, things that AI can’t replicate) is where they fall short.
Airbnb has been operating for 15 years without a formal loyalty program. There are no tiers, no points, and no membership pricing. Passengers who have booked for 100 nights will enjoy the same treatment as first-time guests. On formal metrics, Caravelo scores close to zero on Access.
However, Comparously’s NPS data tells a different story. Airbnb scored 24, Expedia 4, and Booking.com -1. Brand-driven loyalty (with no formal program) outperforms two of the most sophisticated points programs in the travel industry.
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