Rob Rosenstein on the crazy early days, cowboy stories and capital flow | Conversations On Turning 20
11/04/2025 by WiT

When you get to the ripe young age of 20, you’re bound to collect lots of stories – not only about the past but lessons for the future.

As WiT marks its 20th year in 2025, we turn the spotlight on our community, our tribe pioneers and leaders, to tell their stories and share their views on the evolution of online travel and technology.

We ask them to look back on the past and their early days, reflect on the present and why this moment is pivotal for online travel and get them to imagine the future, the next 20.

This special WiT Studio series, “Conversations On Turning 20”, is the collective story of WiT.

As a Chinese saying goes, 以古为鉴,可以知兴替

“By using history as a mirror, one can understand the rise and fall of things.”

 


 

Episode 5: Rob Rosenstein, Chairman and Co-founder, Agoda

The year was (also) 2005. Picture two visionaries sitting on a beach in Phuket, Thailand, sketching plans for a revolutionary travel company that would sell hotel rooms in Asia online.

Well, that romanticised version of the beginnings of Agoda didn’t happen.

As Rob Rosenstein himself said in an interview, “No truth to that story at all. It sounds very romantic, but the real origin was much more mundane.”

The seeds of Agoda were planted in the early 2000s when Rosenstein, who had invested in a friend’s travel agency, saw the potential to take the business online. “We thought there was a great opportunity to service Asian consumers,” he recalls. Along with his co-founder, Michael Kenny, Rosenstein began working on what would eventually become Agoda.

It wasn’t easy. The partners argued “every day for two years” as they shaped their vision, ironing out details and learning on the fly. By the time Agoda launched in 2005, it had already become clear that they were operating in a fiercely competitive environment.

Then in 2007, something happened that changed the company’s fortunes. But even then, it was never smooth sailing.

Here, Rob Rosenstein, now living in Washington, tracks the story of online travel in Asia as it unfolded – from the ones who made it to those who didn’t, and those might survive the next 20.

Watch the full interview:

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