Like many of the world’s richest people, Amazon founder Jeff Bezos is no stranger to investing his wealth into other companies in order to make the number next to his net worth keep going up. Many of these wheelings and dealings have proven wise, such as Amazon’s acquisition of Whole Foods, Audible, and Twitch. Some, like SpaceX competitor Blue Origin—recently in the news for delivering one of the most spectacular explosions ever caught on film—are still finding their footing. As any investor knows, not every speculation will pay off. Now decades into his time as a member of the 0.01 percent, it should come as no surprise that even Bezos has hit his share of whammies. Some were unfortunate whiffs on reasonable ventures like LivingSocial, the Groupon competitor Amazon sunk $175 million into in 2010 only to see it collapse and be bought by Groupon for $0 six years later. Other investment stumbles were the result of more seismic, industry-wide shifts—in a 2014 interview with Business Insider, Bezos likened the loss of his $50 million Pets.com buy-in to “getting a root canal with no anesthesia.” But according to a soon-to-be-published book by New York Times writers Jonathan Swan and Maggie Haberman, Regime Change: Inside the Imperial Presidency of Donald Trump, the tech titan bemoans a much more recent investment as the worst of his life: The Washington Post.