The biggest breakthroughs often come from looking at things differently. Snapchat wasn’t just about photos; it was about messaging. Ryanair didn’t just serve passengers; it served airports. The Swag’s walking stick isn’t just a souvenir; it’s a loyalty program. And as AI reshapes search and advertising, those who reframe their strategies now will be the ones who win.

Thanks to Propellic for sponsoring this edition of the newsletter:

AI just crashed your organic traffic party. Propellic’s AI Strategy Guide breaks down how travel marketers can navigate AI-overhauled search results, future-proof content, and recover lost clicks. Don't fight the robots—beat them at their own game. Your playbook awaits →

Personal note: Many stories in this edition highlight how fast search is changing, why adapting now is critical, and why I recommend checking out this edition’s sponsor, Propellic, as a possible partner in navigating this shift.

0. Your favorite story in the previous newsletter

It was a tie between AI’s impact on online travel (story #1) and Fifty Travel Tips (#10). The very first and the very last :)

1. Reframing to see the full potential

I recently heard Shaan Puri from My First Million tell a story about an investor named Justin. He didn’t say the last name, but my guess is that he was talking about Justin Kan, the entrepreneur behind Justin.tv (which became Twitch) and an early investor in several major tech companies.

Back when Snapchat had only 100k-150k users, most investors dismissed it as a silly college app for disappearing photos. But after meeting Evan Spiegel (Snapchat’s founder) Justin asked a key question: "What if this isn’t about photos at all? What if it’s actually about messaging?" That question changed everything. Instead of comparing Snapchat to Instagram and Facebook, Justin looked at iMessage and WhatsApp, apps people use constantly to communicate. So he did some research and found:

• Almost all iMessage and WhatsApp users send messages daily.

• Way fewer Instagram users post daily

• Snapchat’s engagement patterns matched messaging apps, not photo-sharing platforms.

That’s when it clicked for Justin. Snapchat wasn’t just about sharing photos, it was about communication. Justin saw the full potential, bet big, and won.

Some takeaways for founders:

• Reframe the narrative. If people see your product the wrong way, change how they think about it.

• Track the right metrics. Sometimes, the key to unlocking growth is looking at your business through a different lens.

• Question assumptions. The biggest opportunities aren’t in what people are looking at, but in what they’re missing.

2. Who’s your customer?

Most airlines compete by offering better service, more comfort, and free perks. Ryanair flipped the script. Instead of selling to passengers, it sold to airports. By cutting costs to the extreme and offering ultra-low fares, Ryanair guaranteed small airports a flood of passengers, and those airports paid Ryanair millions to bring them traffic.

Innovation isn’t always about new technology or products. Sometimes, it’s about rethinking who your real customer is. This insight comes from a post by Andres Pereira on LinkedIn. For travel entrepreneurs, it’s a reminder to stop playing by old rules and start rewriting them.

Sometimes, the most powerful pivots do not come from changing your product but from redefining your true customer and value proposition.

3. The real business of US airlines isn't about flying people

Ryanair found profit by redefining its real customers. But what if an airline's real business isn't about flying people? As Courtney Miller shows in Visual Analytics, for many US airlines, the real money isn’t in selling tickets but in printing their own currency (aka loyalty programs).

In 2024, no major US network airline turned a profit from ticket sales alone. Without frequent flyer revenue, every airline would have operated at a loss.

Here’s how it works: Airlines print miles like a central bank prints money. Banks and credit card companies buy these miles in bulk and distribute them to customers. Airlines book this as revenue, sometimes immediately, sometimes when miles are redeemed. If you forget to use your miles, the airline can "expire" them and recognize the revenue.

Loyalty programs have become so valuable that airlines now operate like financial institutions that happen to run flights. Without them, ticket prices would likely be much higher.

If you’re building in travel, this is another reminder that the most valuable part of a business isn’t always the most obvious.

4. A simple and memorable hospitality loyalty program

My wife and I recently celebrated our 25th anniversary at The Swag, a charming mountain hotel in North Carolina. It was our first time there, but their repeat guest rate is far above the industry average, in part due to a refreshingly simple, inexpensive and effective loyalty program.

Every first-time guest receives a wooden walking stick, a practical keepsake for hiking the Smoky Mountains. Attached is a tag engraved with the year of your stay (e.g., The Swag – 2025). Returning guests receive a new tag for each visit, creating a personal record of their stays over the years.

Beyond the emotional connection, the walking stick is something guests can use for years on hikes anywhere. Each time they take it on a trail, it brings back memories of their time at The Swag, keeping the hotel at the top of their minds and reinforcing the desire to return.

Einstein once said that simplicity is the highest form of intelligence, because it makes things easy to understand. The Swag’s loyalty program is a perfect example. There’s no app, no points to track, no complicated tiers. Just a meaningful, physical connection to the place. Loyalty isn’t just about rewards; it’s about creating a reason to return.

If you’ve run across other simple loyalty examples, please share.

5. Google’s AI overviews are pushing travel sites down

AI Overviews in Google search have surged 558% in just two months, expanding from 2,832 to 18,652 keywords. They now occupy 42% of desktop and 48% of mobile search space, pushing organic results down by 980 pixels. As a result, organic CTR has dropped from 1.41% to 0.64%, making visibility a growing challenge for travel brands.

There is an opportunity, though; being cited in an AI Overview raises CTR from 0.74% to 1.02%. But citations are volatile, with 70% changing every 2-3 months. Travel marketers need a new approach to stay visible.

Propellic’s AI Strategy Guide offers a roadmap to adapt. It covers AI-resistant content strategies, ways to rank within AI Overviews when necessary, and how to get cited in AI-driven search tools like Claude and Perplexity.

And now, as we see in the next story, Google is taking things even further. AI Overviews were just the beginning—now, a new experimental feature called AI Mode lets users ask multi-part questions and get even deeper AI-generated answers.

6. Google’s AI search shift

As mentioned above, AI Overviews are rapidly expanding and reshaping search. Matt Lerner shares more data reinforcing this trend: Google now shows AI Overviews for 40% of all searches (and growing at 14% MoM) and for 57% of informational intent searches. And searches with AI overviews get 70% fewer clicks. Big changes open big opportunities for those who can get in early and rank for AI responses. Big new traffic sources are opening up.

For those who wish they had gotten in early on the Google SEM game and locked in a big PageRank advantage, now is the time to move fast and secure prime positioning in AI-driven search.

7. Google’s new AI Mode takes search even further

Google just launched AI Mode, an experimental search feature that lets users ask complex, multi-part questions and follow up for deeper answers, similar to Perplexity AI and ChatGPT Search. Unlike traditional search, AI Mode simultaneously compiles results from multiple sources, providing detailed comparisons and insights without extra queries. This could mean even fewer clicks for travel brands, as travelers get more answers without leaving Google. But AI Mode still pulls from external sites, meaning content optimized for AI citation could gain visibility.

8. Google Search is still dominating…by a lot

Despite the rise of AI tools, Google Search isn’t shrinking. It grew over 20% in 2024, handling more than 14 billion searches per day. Meanwhile, ChatGPT gets at most 37.5 million search-like prompts daily, meaning Google still sees 373 times more searches than OpenAI’s tool. Read + SparkToro

While AI-driven search (like Google’s AI Overviews and AI Mode) is changing how people find information, this data shows that Google remains the dominant player. For travel marketers, this reinforces the need to prioritize SEO, AI citation strategies, and organic visibility on Google, rather than shifting focus entirely to AI search tools.

9. The $1 Trillion question: who will you advertise to?

Ken Mandel recently wrote an interesting post about what happens when AI agents start making more purchasing decisions than humans.

For over a century, advertising has been about grabbing human attention. But with AI filtering search results, handling bookings, and making automated purchases, traditional ads could become irrelevant. Instead of competing for clicks, brands will compete for AI-driven shelf space, the digital equivalent of being a top recommendation in an AI’s decision-making process.

Search and display ads could fade as AI agents filter content before humans even see it. Rather than bidding for impressions, brands will need to optimize for AI assistants, structure data for machine readability, and build trust through verified reviews and sustainability metrics.

For travel brands, this means ensuring AI assistants rank them as top choices, integrating with AI-driven booking systems, and embedding themselves in personalized AI commerce experiences. The future of advertising isn’t about persuasion but making sure AI agents recognize and recommend you.

The shift has already started. The question isn’t if advertising will change, but how fast brands will adapt.

10. The art of snack time eye contact

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