Maybe Information Actually Doesn’t Want to Be Free

In June 2017, the site landed one of its biggest scoops: a feature that revealed sexual harassment allegations against one of Silicon Valley’s most well-connected venture capitalists. Six women had accused Justin Caldbeck, a partner at Binary Capital, of unwanted sexual advances, with three of them speaking to the reporter, Mr. Albergotti, on the record.

The story exposed a pervasive culture of misogyny and harassment within tech, immediately raised The Information’s profile and was a precursor of the broader #MeToo movement. But Mr. Albergotti, who now works at The Washington Post, remembered the staff’s anxiety as they got closer to publishing. They were keenly aware of what had happened to Gawker, which was sued for invasion of privacy by Hulk Hogan. The suit, which was financed by the venture capitalist Peter Thiel, drove Gawker into extinction and stoked a fear among publishers that anyone with enough money and willpower could vaporize a news outlet.

As the Caldbeck story was about to go to press, Ms. Lessin was in Italy attending a conference. She consulted the company’s liability insurance, which she had printed out, in her hotel room before heading to a dinner where she would be seated with Jeff Bezos. “I don’t remember if I vomited or not,” she said. “But I was very nervous.” She gave the green light.

Mr. Caldbeck didn’t sue. Instead, he resigned. A short while later, his venture firm collapsed. As a female entrepreneur, Ms. Lessin felt The Information’s work was “deeply personal,” especially as several men in the industry, who had heard the piece was in the works, contacted her to suggest the claims were overblown. These were “men I respect, who I was close to,” she said.

She wouldn’t name them. Ms. Schuker Blum, who worked with her at The Journal, said Ms. Lessin is not a gossip, like many reporters. “She’s not the journalist who’s always complaining,” Ms. Schuker Blum said. “She’s not a conspiracy theorist. She sees the best in people.”

Daniel Ek, the chief executive of Spotify, said he found the occasional, critical story on his company “not unfair.” But he added that Ms. Lessin “has to walk a tightrope given the level of access that she has. That’s got to be tough.”

Ms. Lessin’s connections continue to raise eyebrows, particularly those to Facebook. She and her husband are friends with their Harvard classmates Mark Zuckerberg, the company’s chief executive, and his wife, Priscilla Chan, who runs the couple’s philanthropy efforts. They attended each other’s weddings and both have young children. (Ms. Lessin’s two boys, Lion and Maverick, are both under the age of 3.) Mr. Zuckerberg was at The Information’s launch party, where she joked that for the super-high subscription rate of $10,000 a story could be killed (but just one). Recently, Ms. Chan was a speaker at an Information event.