1. How I Discovered Booking Holdings
I first heard about Booking Holdings during the early stages of the COVID-19 pandemic, on a podcast that was unpacking the carnage unfolding in the travel and hospitality sector. Airlines were grounded, hotels were empty, and most travel stocks were getting hammered. But where others saw collapse, I saw an opportunity in patience.
It was April 2020, and I remembered Booking Holdings from its earlier days as Priceline Group—a name familiar to me not only as an investor, but as a frequent international traveler. I had used their platforms—Booking.com, Agoda, Priceline, and KAYAK—on trips over the years. The brands were trusted, easy to use, and increasingly indispensable to the modern travel experience.
And so, I began to dig deeper.
2. The Spark: When Disruption Meets Durability
Travel, at that moment, was one of the most dislocated and emotionally charged sectors of the economy. The headlines were grim. The public sentiment was fear. And yet, through a long-term lens, this looked like the kind of moment that Howard Marks writes about: “You don’t buy good things at any price—you buy good things well.”
I believed that the pandemic would have a 2–3 year impact, not a permanent one. Travel may pause, but it wouldn’t disappear. Human connection, global business, and cultural curiosity don’t vanish—they rebound.
3. My Investment Entry
So, on April 8th, 2020—a date that turned out to be the bottom of the market for many travel stocks—I made an initial investment in Booking Holdings. Total fluke? Perhaps. But the underlying conviction wasn’t: I believed that Booking’s scale, brand portfolio, and network effects would make it one of the first and strongest to rebound once global movement resumed.
Over time, I continued to dollar-cost average into the position. I’ve now deployed approximately 3% of my total capital into Booking Holdings.
4. The Outcome So Far
The results speak for themselves:
- 200% total return across my cost basis
- A compound annual growth rate (CAGR) of 14.8%
- Resilient margins, renewed growth, and a structurally stronger business post-COVID
And perhaps most important: I still believe the best is ahead.
5. Why Booking Holdings? The Business Behind the Brand
Booking Holdings is not just a travel agency—it’s an infrastructure layer for global travel commerce. Their brands are category leaders:
- Booking.com – Online accommodation juggernaut, particularly strong in Europe.
- Priceline – Discount and deals-focused travel services, mainly in North America.
- Agoda – Dominant in Asia-Pacific for accommodation and flights.
- KAYAK – Metasearch engine powering millions of price comparisons.
- OpenTable – The go-to for restaurant reservations in the U.S. and beyond.
- Wider ecosystem – Travel insurance, advertising, SaaS for restaurants, and more.
What ties this all together is platform leverage and customer loyalty. When a traveler books flights, rooms, cars, and even dinner reservations through one ecosystem, that data advantage and margin capture becomes compounding.
6. What Makes Them Durable
Booking Holdings’ moat is built on:
- Global scale and localization: operating across dozens of countries with tailored offerings.
- Brand equity: Booking.com and Priceline are trusted and top-of-mind.
- Two-sided network effects: Connecting millions of travelers with accommodation providers, restaurants, and experiences.
- Strong unit economics: High margin software/affiliate model over asset-heavy hotel chains or airlines.
Their continued investment in AI-driven personalization, mobile UX, and supply optimization also gives them staying power in a rapidly digitizing sector.
Latest Earnings
As at the 19th May 2025, latest earnings call, Bookings reported a ~$25bn annual revenue (quarterly revenue growth of 7.8% yoy), which indicates a approx 5% of total market share.
7. Role in My Portfolio
Booking sits in my G1 Fund – Core Compounders.
It represents long-term secular tailwinds, global diversification, and the return of discretionary consumer spend. It’s not just a recovery play anymore—it’s now proving itself to be a compounding platform business in its own right.
8. What I’m Watching
Looking ahead, I’m watching:
- Continued recovery and normalization of international travel, particularly in Asia-Pacific.
- Margin expansion as scale efficiencies from post-COVID restructuring take hold.
- Expansion into ancillary services (e.g., insurance, advertising, dynamic packages).
- AI-enabled recommendations and customer retention tools.
- Regulatory environments in Europe and data privacy implications.
9. What Would Break My Thesis
The risks I monitor include:
- A structural shift away from third-party aggregators (e.g., direct booking gains).
- Increased regulation around fees, advertising transparency, or algorithmic pricing.
- Major platform competition from Google Travel or Apple-native booking tools.
- Sustained macro shocks (e.g., global recessions, geopolitical instability affecting mobility).
However, even in that context, Booking Holdings has consistently adapted, acquired, and led.
Final Reflection
Booking Holdings is the kind of business that looks boring on the surface—but beneath it lies a beautifully complex, deeply optimized global engine for travel commerce.
If my children ever ask me why I invested in a travel company at the peak of a pandemic, I’ll tell them: “Because I believed in the return of wonder. And when the world started moving again, I wanted to be invested in the rails that helped people go.”
also
“The Market is often irrational, drive either by Extreme Fear or Extreme Greed, learn to look for these signs”
