Like the world’s richest men, Amazon founder Jeff Bezos is no stranger to investing his wealth in other companies to boost the number next to his fortune. Many of these wheels and deals, like Amazon’s acquisitions of Whole Foods, Audible and Twitch, have proven to be wise. Some — like SpaceX’s rival Blue Origin — have recently been in the news for one of the most recent launches spectacular explosions those filmed are still finding their place.
As any investor knows, not every speculation will pay off. Now that he’s been a member of the 0.01 percent for decades, it should come as no surprise that even Bezos has had his fair share. Some were failed ventures at reasonable ventures like Groupon rival LivingSocial. Amazon earned $175 million 2010 only to see it crash and be Purchased by Groupon six years later for $0. Other investment stumbles were the result of more seismic, industry-wide shifts—in a 2014 interview with Business InsiderBezos likened the loss of the $50 million Pets.com purchase to “getting a root canal without any anesthesia.”
But according to his soon to be published book New York Times writers Jonathan Swan and Maggie Haberman, Regime Change: Inside Donald Trump’s Imperial PresidencyThe tech titan laments a more recent investment as the worst of his life: The Washington Post.
In December 2024, at a dinner two months ago with President Trump It lays off more than 300 people Bezos was heard complaining about Post employees in the paper California Post after reviewing a portion of the book ahead of its June 23 release date.
“The people there are terrible,” Bezos told Trump. “They don’t listen. My other companies, they do.”
Bezos’ failure to shape his newsroom vision was not for lack of trying. It is a few weeks before the elections to be held in November 2024 personally intervened Crushing the paper’s already written endorsement of Kamala Harris. And like him Posted in X In February 2025, weeks after the staff cuts, the paper’s new defiant opinion page will “write daily in support and defense of two pillars: personal liberties and free markets.” However, the damage was already done. That’s no surprise after seeing a nearly 150-year-old media institution crumble into rags in the ill-equipped hands of a would-be Hearst. subscribers abandoned ship in droves.
Although Bezos points to the Post 100 million dollar loss in 2024 Swan and Haberman’s mention of that lunch with Trump as the impetus for the cuts points to a more complex, emotional reason.
“According to Trump, Bezos told him he lost half his friends because of the investment,” the authors told the California Post. “Bezos would tell others it wasn’t entirely true: He hadn’t lost friends, but people close to him had urged him to sell the paper.”
Ultimately, only Bezos knows what motivated his decision to lay off his staff. But if it’s simply lack of camaraderie at the root of his concern, but he still refuses to allow the paper to return to its former level of journalistic integrity and autonomy, there’s another type of investment he might want to try. RentAFriend.com.
