The first one
In 2011, Steven Vaile invested his last $25,000 as a deposit on a property in Phnom Penh, Cambodia. That was the first Mad Monkey hostel.
It was not a plan that arrived fully formed. He was already in Southeast Asia, working as a management consultant on the Credit Bureau Cambodia project — helping establish the country's first credit bureau alongside the IMF and World Bank. The hostel was a parallel bet, made with co-founders, on the idea that the backpacker category in Southeast Asia was ready for something that combined decent design, a genuine social environment, and operations that actually worked.
It turned out to be right.
What it became
From one property in Phnom Penh, Mad Monkey grew to 21 properties, 21 restaurants, and 20 bars across seven countries in Southeast Asia. At its height the company employed approximately 1,000 people. It became the market leader in its category.
Steven served as Founder, CEO, and Chairman. The growth was real and the operational complexity was significant — managing staff across seven countries, maintaining brand consistency across 21 properties, and building a culture in a fast-growing hospitality business in one of the world's most logistically challenging regions. None of it was straightforward.
The Mad Monkey article "Yesterday Was My Last Day Leading Mad Monkey" — published on LinkedIn — covers the departure in Steven's own words. The earlier piece, "Panic Is Optional," draws the through-line from Royal Navy engineering to the chaos of building a business from nothing.
Why it matters beyond hospitality
The standard reading of the Mad Monkey chapter is that it demonstrates entrepreneurial range. That is true. What it also demonstrates is something more specific: Steven has built a business from zero to market leadership in a category that had nothing to do with his technology background. That requires understanding what a customer actually buys — which is almost never what the company thinks it is selling.
That commercial insight is the same skill that a board needs when a CTO presents an AI strategy. The CTO is selling the technology. The board needs to evaluate the business case. Steven can do both because he has had to do both — in radically different contexts, under real pressure, with real money.
Current status
Steven founded Mad Monkey in 2011 and led the company through its growth phase. He is no longer operationally involved in the business.