The media entrepreneur Jessica Lessin chats with DealBook about the news landscape and her latest media bet.
In 2013, Jessica Lessin, a reporter at The Wall Street Journal, left the paper to start a competing publication, The Information.
A few years later, her fledgling newsroom had grown to nearly two dozen reporters and editors and booked more than $20 million in sales, as she revealed in a profile I wrote for The Times’s Sunday Business. She says she has since doubled her editorial staff and continued to stay profitable, with revenue growing 30 percent in 2024 over the previous year.
But it’s her investments outside of The Information that are gaining attention these days.
Her company Lessin Media has put money into Semafor, The Ankler, the former Business Insider editor Nicholas Carlson’s Dynamo, Kevin Delaney’s Charter Works and other titles at a time when the news business appears bleaker than before. Lessin, however, is optimistic.
I caught up with the entrepreneur about her latest media bet, the tennis publication Racquet magazine, and what she thinks about the changing news landscape. This interview has been edited and condensed.
This investment seems different from your others. How did you come to it?
I actually got introduced to Racquet by a number of fans of the magazine. And it was like the weirdest experience, because I was reading the magazine, and then I wanted to buy, like, all the clothes in the magazine. I went to the website, and I wanted to buy all the merch. And they’re hosting an event at the U.S. Open. And I was like I want to go to that. And I want to read this great profile about the mental coach behind the world No. 1 tennis player.
This sounds like it was something that just struck you personally. I assumed you’d be more focused on sales and market size and margin.