Koolen studied technical business administration at the University of Twente. Without completing his degree, he entered the business world as a management advisor and subsequently became an angel investor in internet startups during the sector's early growth years. He was one of the founding figures of Booking.com, a hotel price-comparison platform. In 2005 the company was sold to Booking Holdings for 110 million euros. Koolen remained in the chief executive role until 2011, by which point Booking.com had become one of the world's dominant online travel agencies.
By 2013 his wealth was estimated at 115 million euros, placing him 232nd on the list of the wealthiest people in the Netherlands. His international profile extended further when Uber established its headquarters in Amsterdam and founder Travis Kalanick named Koolen as COO. Simultaneously he founded Agri Brasil, a conglomerate of large-scale dairy farms. In subsequent years Koolen shifted focus toward renewable energy, becoming Chairman and CEO of Koolen Industries, a Dutch clean energy conglomerate with interests including battery technology.
Koolen entered the Dakar Rally for the first time in 2009, competing on a Honda CRF450 motorcycle and finishing 69th in the motorbike classification. It was the beginning of a long and varied Dakar campaign across multiple vehicle categories.
For the 2010 edition Koolen switched to a McRae Enduro buggy. A troubled third stage — in which he passed all checkpoints but became stranded before reaching the bivouac — forced his retirement. The following year he developed the GoKoBra, his own purpose-built off-road buggy, entering two cars for himself and teammate Jurgen van den Goorbergh. Koolen was disqualified after the sixth stage: despite completing it and initially receiving dispensation for finishing outside the time limit, the organisation reversed the decision after determining he had missed a checkpoint. In 2012 the GoKoBra programme returned and the team completed the event in 59th place overall.
Koolen entered the quad category for the first time at the 2013 Dakar Rally and completed the event in 17th place in class — a creditable result for a privateer in the discipline.
The 2014 Dakar Rally was Koolen's most historically significant participation. By combining a quad entry with truck co-driving duties alongside Jurgen van den Goorbergh and Gijs van Uden aboard a Ginaf truck run by the Maxxis Dakar Team, Koolen completed the rally in all four vehicle classifications — motorcycle, buggy, quad, and truck — becoming the first participant ever to accomplish that feat. The truck finished 37th.
At the 2015 event Koolen ran a self-developed quad. During the fifth stage he deviated from the prescribed route and drove through a protected area of the Atacama Desert; Chilean authorities arrested him, though he was released after questioning. He was not alone in the infraction — fellow competitor Matteo Cassucio also received attention from authorities — but Koolen retired from the rally in the following stage. In 2016 he returned on his Honda quad and recorded competitive top-ten stage results before retiring after stage nine, when an incident involving a helicopter caused his unmanned quad to fall fifty metres to the ground.
For the 2017 Dakar Rally, Koolen's team developed a new machine called the Barren Racing quad. With the new vehicle he scored his first Dakar stage victory, winning the shortened 219-kilometre stage between Tupiza and Oruro — a stage curtailed by severe weather. He finished the 2017 event in seventeenth place in the quad class.
Koolen's dual identity as a technology entrepreneur and motorsport competitor is unusual in the rally raid world. His record as the first finisher of the Dakar Rally in all four vehicle classes places him in a unique position in the event's history, alongside his business legacy as a founding figure of one of the world's largest online travel platforms.
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