5. 11-Minute Flight to Space

Year Purchased: 2021
Estimated Value: $4.4 billion* 

Jeff Bezos described his adventure in his Blue Origin New Shepard capsule, which is autonomous and doesn’t require a pilot, as “the best day ever.” The eleven-minute spaceflight included the billionaire and three crew members, one of which was the oldest person to travel to space and the other the youngest.

The spaceflight cost $4.4 billion. Bezos’ entire flight was eleven minutes, but he only spent three of them actually in space. The flight wasn’t overly risky, as the New Shepard capsule had never had an accident in fifteen spaceflight tests. Blue Origin was founded in 2000, and, twenty-one years later, Bezos saw the fruits of his company’s labor.