How Jessica Lessin Built a Digital Media Business by Covering Digital Media

Cynthia Littleton
·2-min read

Jessica Lessin was ahead of the curve on the boom in subscription media.

While working as a reporter for the Wall Street Journal nearly a decade ago, she saw an opening in the journalism market for more thoughtful longform reporting. The decision to follow her instincts meant that she has been in the business of launching a subscription business just as the companies she covers went headlong into an industry-shaking pivot to direct-to-consumer offerings.

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On the latest episode of Variety’s podcast “Strictly Business,” the founder and editor-in-chief of The Information discusses the growth of the eight-year-old outlet that has distinguished itself through deep-dive reporting, analysis and scoops in the tech and media worlds.

“It’s been fascinating to see the media business embrace [DTC services] and in some ways be upended by it,” Lessin says.

Lessin is the sole owner and financier of Information, which has a staff of about 40 at present. Running the company has given her perspective on what it takes to be an effective CEO and the factors that fuel a successful venture.

“I always come back to this one — as a journalist whenever I saw turnover at a company, I always thought it was a really bad sign,” she says. “And to be clear, it often is…But I haven’t gotten every hiring decision correct. I’ve made mistakes. As a founder you realize [personnel] is the only side you have to get right, right? If you can run a team and build a team, that will make you successful. If you can’t, you won’t. A different perspective on that is something I’ve felt while wearing this hat while still wearing my journalist hat.”

Lessin also offers her thoughts on what she sees ahead for Silicon Valley stalwarts including Facebook, Google and TikTok. TikTok’s Chinese parent company ByteDance, which tangled with the Trump administration earlier this year, is one to watch for sure, she says.

“They’re one of the world’s most valuable private companies headed for a big IPO in next 12 months or so,” she says. “I think they’ll be some more drama to the story.”

“Strictly Business” is Variety’s weekly podcast featuring conversations with industry leaders about the business of media and entertainment. A new episode debuts each Wednesday and can be downloaded on iTunes, Spotify, Google Play, Stitcher and SoundCloud.

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