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.
At a December 2024 dinner with President Trump, just two months before laying off over 300 people at the paper, Bezos was heard complaining about Post staffers, reports the California Post after reviewing an excerpt ahead of the book’s June 23 release date.
“The people there are terrible,” Bezos griped to Trump. “They don’t listen. My other companies, they listen.”
Bezos’ failure to shape the newsroom in his worldview wasn’t for lack of trying. In the weeks leading up to the November 2024 election, he personally intervened to squash the paper’s already-written endorsement of Kamala Harris. And as he posted on X in February 2025, weeks after slashing staff, the paper’s new insubordination-free opinion page would be “writing every day in support and defense of two pillars: personal liberties and free markets.” The damage had already been done, however. After seeing the nearly 150-year-old media institution reduced to a rag in the ill-equipped hands of a would-be Hearst, it’s no surprise Post subscribers abandoned ship in droves.
Though Bezos points to the Post’s $100 million in losses in 2024 as the impetus for the downsizing, Swan and Haberman’s recording of that dinner with Trump hint at a more complicated, emotional reason.
“In Trump’s telling, Bezos told him he had lost half his friends over the investment,” the authors told the California Post. “Bezos would tell others that wasn’t quite right: He hadn’t lost friends, but people close to him had urged him to sell the newspaper.”
Ultimately, only Bezos knows what motivated his decision to cut staff. But if it’s simply a lack of camaraderie at the root of his angst, but he still refuses to let the paper return to its former levels of journalistic integrity and autonomy, there’s a different kind of investment he might want to try over at RentAFriend.com.
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