Amazon founder and CEO Jeff Bezos has once again taken a dive onto the risky end of the pool by buying the Washington Post for $250 million. Bezos, who according to the Bloomberg Billionaires Index was in 2012 listed as one of the wealthiest people in the world with an estimated net worth of $22.1 billion is no stranger to risky endeavors. One of his other passions is space. He owns Blue Origins, a company that is developing low-cost space habitats. And earlier this year his expedition firm trolled the Atlantic to find spent NASA Apollo-era rockets. But that’s just the beginning. Here’s a quick look at some of Bezos’ more interesting activities over the years.