Some stories in this week’s edition are about surprise, others are about deep shifts: AI concierges sending birthday cakes unprompted, mystery flights to unknown destinations, solopreneurs building million-dollar startups, Shopify doubling down on AI, fintechs embracing eSIMs to power global connectivity, and more. I hope you enjoy it!

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

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0. Most clicked in the previous newsletter

The most clicked link in the last issue was the GetYourGuide report on how reviews impact conversion rates.

1. The bridge between content and commerce

New deep dive. This one’s on how Stay22 is building the bridge between travel content and monetization, and becoming core infrastructure for the travel creator economy. They’re driving 3x to 10x revenue lifts for travel players, blogs, weather sites, and now YouTube, with tools that are smart, subtle, and built for conversion. Big thanks to Andrew Lockhead and Rami Nuseir for giving me an insider look at how everything works and letting me share the story. Hope you enjoy it as much as I did researching and writing it. Read Stay22 Deep Dive.

2. Is Lean Startup dead, or just evolving?

Fletcher Richman wrote a post about the Lean Startup being dead. With AI tools like Cursor and Replit writing most of the code, he argues it's faster and smarter to ship first and validate later.

He's right that AI is transforming development speed. But I think the core of Lean Startup was never just about saving time or money on code. It's about reducing waste by making sure you're solving the right problem. Building faster doesn't mean building better if you skip customer discovery. Understanding customer problems remains fundamental, no matter how quickly you can code a solution.

If anything, this new speed only raises the stakes. As Fletcher points out, the realt code anymore; it's user attention. With more products flooding the market, distribution matters more than ever. The Lean Startup principles of validating what you build and understanding real needs are still essential. The method may evolve, but the mission remains the same.

3. The AI concierge that sends cakes

At a recent Travel Tech Thursdays event in Kuala Lumpur, industry leaders shared how AI is transforming guest experiences. One story from The Luxe Nomad stood out. Their AI concierge, Bella, surprised everyone by sending a birthday cake to a guest, completely unprompted. During a chat, the guest casually mentioned a birthday, and Bella picked up on it, triggered a ticket, and arranged the delivery. Bella does more than just respond. She anticipates needs, sends personalized offers before guests ask, and adjusts her approach based on past interactions. Her creators added a slight delay to her replies to make her seem more human-like. That pause makes conversations with her seem natural and thoughtful. Bella’s proactive approach shows how AI in hospitality is moving from reactive to intuitive. Read +.

4. Travel eSIMs are showing up in Fintech roadmaps

Roaming has emerged as a powerful growth engine for fintechs like Revolut and Nubank. Digital SIM cards let users access mobile data seamlessly across borders with no physical cards, no surprise fees, just instant activation and easy top-ups, all managed directly from an app. For fintechs, this is becoming a new revenue stream that deepens user engagement. Read + Kintxo Cortes

But it’s not just the big fintechs pushing the trend. Players like Kolet and Airalo are finding product-market fit with traveler-focused eSIM solutions, reshaping how users stay connected abroad.

5. How AI is supercharging solo founders and reshaping tech investing

In How AI Disrupts Tech Investing, Tomas Pueyo explains how AI is rewriting the rules for startups. Founders can now build and launch products solo, with minimal upfront costs. This rise of solopreneurs is cutting VCs out of early-stage funding, as individuals or small teams can compete with established players. Competition is rising, and the need for big funding rounds is shrinking.

6. Shopify makes AI mandatory for all employees

In an internal memo, Shopify CEO Tobi Lütke announced that AI usage is now mandatory for all employees. Lütke called it the most rapid shift in how work is done he’s seen in his career. Key points:

• Employees are expected to use AI as a core part of their workflow.

• Lütke sees AI boosting productivity by 10x to 100x for top performers.

• All projects are required to prototype with AI to accelerate learning.

• Mastery of AI tools and skills is now part of evaluation metrics and performance reviews.

• Teams need to prove that AI can’t solve their problems before requesting additional headcount.

7. Lighthouse + The Hotels Network

I have known Juanjo Rodriguez for nearly two decades and had the privilege of serving on the board of The Hotels Network. Juanjo is one of the most inspiring entrepreneurs I know. Visionary, grounded, and relentless in execution. I remember when he first shared the idea for THN with me in San Francisco, and from that moment, I knew he was going to build something extraordinary. But what he created goes beyond that. He built a remarkable company with a vibrant culture, powered by a passionate and motivated team. I’m thrilled to see THN reach this new chapter by joining forces with Lighthouse. The work they’ve done to power direct bookings and personalized guest experiences is now part of an even bigger platform, and it’s a testament to the team’s dedication and Juanjo’s leadership. Congrats Juanjo & the entire THN team!

8. See you at Phocuswright Barcelona

Looking forward to seeing some of you at Phocuswright in Barcelona next month. I’ll join Gillian Tans, former CEO of Booking.com, for a session moderated by Chris Hemmeter of Thayer Investment Partners. The session is on Thursday, June 12, from 9:45 to 10:10 CET. If you’re planning to attend and haven’t gotten your tickets yet, you can use this personalized link to get 10% off the current ticket price.

9. Destination unknown

Scandinavian Airlines has a mystery flight, where passengers book tickets but do not know the destination. Last year the destination was Athens, and this year they ended in Seville.

10. He’s right

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Mauricio Prieto