A booking site got big because of domain names

Why I finally enjoyed reading again

I hate reading. Always have. Even as a kid I’d find any excuse to avoid books.

Ten years building companies and I still force myself through business books. Most are garbage anyway. Same recycled advice wrapped in different stories.

Then I picked up The Machine by Stijn Bronzwaer. It’s about how Booking.com started. Finally found a book I couldn’t put down. (first book I read in Dutch since ages too)

Here’s the thing. Reading about a business that mirrors your own changes everything. Suddenly the struggles make sense. The growth hacks feel familiar. The mistakes hit different when you’ve made them too.

Booking’s origin story starts with Geert-Jan Bruinsma in his Amsterdam apartment in 1996. He was pissed off trying to book hotels over the phone. Language barriers. Busy signals. Hotels hanging up on foreigners.

So he built Bookings.nl (later Booking.nl). The premium domain Booking.com was owned by someone else and would cost serious money to acquire.

The real breakthrough came from their obsession with SEO. While competitors were still figuring out Google, Booking went all-in on massive landing page generation. They’d create dedicated pages for every city, every type of accommodation, every search combination they could think of.

Deep internal linking. Scaled content architecture. They understood early that Google rewarded sites that could answer every possible travel query.

Similar playbook to what we run in the EOR space. Dedicated pages for different countries make sense because employment law is genuinely different everywhere. The content has to be tailored anyway.

But here’s what the book actually reveals about their obsession with testing. They didn’t just test button colors. They tested everything. The shade of blue on their logo. Whether to show prices in ascending or descending order. Whether hotel photos should be landscape or portrait.

Koen Riedijk, their head of user experience, would run hundreds of A/B tests simultaneously. Most changes moved conversion rates by tiny fractions. But those fractions added up to millions in revenue.

The book describes countless experiments with button colors, text copy, page layouts. Some moved the needle significantly. Others barely registered. But they kept testing because at their scale, even 0.1% improvements were worth millions.

They also had zero shame about copying competitors. The book describes how they’d monitor competitor sites daily. New feature launches? Copied within weeks. Better search filters? Implemented faster.

Competitive intelligence was built into their DNA. They’d analyze every successful booking site, travel agency, even airline websites for ideas worth stealing.

The growth was brutal. Constant pressure to expand into new markets before competitors could establish themselves. They’d hire country managers and figure out regulations as they went.

Booking nearly died in 2000. The dot-com crash hit right as they were gaining traction. Funding dried up. Staff got slashed from 150 to 25 people. Survival mode kicked in hard.

They survived by being scrappier than competitors. While Expedia held strategy meetings about European expansion, Booking was already live in multiple countries. While others hired consultants, Booking hired locals and figured it out.

The regulatory battles were constant. Germany tried to ban their business model entirely. France required them to register as a travel agency. Italy demanded they pay tourist taxes for customers.

They fought these battles market by market. Sometimes they won in court. Sometimes they just paid the fines and kept operating. The book shows how they’d rather ask forgiveness than permission.

The Priceline acquisition in 2005 was wild too. Priceline was struggling in the US. Their stock was under $7. But they saw Booking’s European growth and bought them for $133 million.

Within five years, Booking was generating more revenue than Priceline’s entire US operation. The subsidiary became bigger than the parent company.

Reading about their expansion into Asia felt like déjà vu. Cultural misunderstandings everywhere. They assumed European hotel booking behavior would translate globally. It didn’t.

In Japan, hotels wanted fax confirmations for every booking. In China, customers expected to pay cash on arrival. In India, dealing with massive overbooking was standard practice because hotels assumed many reservations wouldn’t show.

Their technology kept breaking in unexpected ways. Systems that handled Amsterdam’s internet infrastructure couldn’t cope with Bangkok’s spotty connections. Mobile sites that worked perfectly in London were unusable on older phones common in Southeast Asia.

But they kept adapting. Built separate mobile sites for different connection speeds. Created country-specific payment methods. Hired local staff who actually understood the markets.

The best part of the book? Brutal honesty about their mistakes. Like when they tried to expand into flights to compete with Expedia. Burned through millions. Never gained traction. Eventually shut it down.

Or their restaurant booking venture. Seemed logical. Hotels and restaurants both take reservations. But the business models were completely different. Another expensive lesson.

The book admits most of their early success was timing. The internet was becoming mainstream exactly when people wanted alternatives to travel agents. Mobile adoption happened right as they were scaling globally.

Most business books pretend success was inevitable. That every decision was genius. This one shows the chaos. The near misses. The stupid mistakes that somehow worked out.

Like how they discovered their review system almost by accident. Hotels kept complaining about bad reviews, so Booking started verifying that reviewers actually stayed at the property. Turns out verified reviews converted way better than anonymous ones.

Or how their “free cancellation” policy started as a desperate attempt to differentiate from Expedia. Hotels hated it. Booking’s finance team hated it. But customers loved it, and it became their biggest competitive advantage.

The book also reveals how they built their company culture around data and testing. New employees had to understand statistics. Marketing campaigns needed testing plans before approval. Even office decisions got measured for impact.

That obsession with measurement extended everywhere. They tracked customer service response times by individual agent. They measured how long people spent on each page. They tested email signatures, page load speeds, checkout flows.

Reading about a business that mirrors your own changes everything. Their struggles with international expansion. Regulatory uncertainty. Scaling customer service across time zones. Competition from better-funded rivals.

Every challenge felt familiar. Every breakthrough made me think about our own growth strategies.

That’s why I actually enjoyed reading for once. It wasn’t some consultant’s framework divorced from reality. It was real people figuring it out as they went. Making mistakes. Learning from them. Building something massive through iteration rather than inspiration.

The chaos wasn’t sanitized into clean lessons. The victories weren’t inevitable. The failures weren’t glossed over with wisdom.

It was just honest about how messy building something actually is. How many experiments fail. How much depends on timing and luck and being willing to try stupid things that might work.

Funny how finding the right story changes everything. Maybe I don’t hate reading. Maybe I just hate boring books written by people who’ve never actually built anything.

Here’s the link to the book on Amazon: https://www.amazon.com/Machine-How-Booking-com-Took-World-ebook/dp/B0BW8YY5QG - not affiliated, just actually worth reading.