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Entertaining Entrepreneurship

Jessica Lessin of The Information

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Jessica Lessin is founder, CEO, editor-in-chief and sole owner of The Information, the influential subscription-only tech publication that was launched on a simple idea: write deeply reported articles about the technology industry that people won’t find elsewhere. As she shares in this episode, like many who work in the news business, she got the journalism bug early on, working on school papers and enjoying the permission it gives you to “be a little bit nosy.” While at Harvard, she covered the faculty beat for The Harvard Crimson, something she likens to covering Congress. Oh, and there was also “the other thing that was going on” — the launch of Facebook. Jessica went on to cover a new emerging tech beat for The Wall Street Journal, writing about startups and “what the kids were doing online.” But she had trouble convincing editors that companies like Facebook were worth writing about. She says they simply didn’t understand the business models that would ultimately propel these companies. 

Like many entrepreneurs, Jessica saw an opportunity within a disruptive moment. She was convinced that there was a broad audience for a business publication that focused on deep reporting around technology. As publishers tried to chase a business model based on “eyeballs and clicks,” she decided to develop her own model that would build and monetize audiences based on quality information. Jessica just celebrated the 7th anniversary of The Information, and it’s clear that her business model and her thesis — that you can’t remove business from the context of technology and disruption — are more relevant than ever. Tune in to hear more about what she learned covering tech startups and how it informed the launch of her own tech news startup.

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Highlights from this episode:


“The idea that I could keep learning about so many subjects and that would be my day job was really exciting. I think I also liked, you know, the sort of permission to just go around and kind of learn things and be a little bit nosy.”



“Seeing the earliest stages of a trajectory of a technology company and its impact certainly, you know, probably had the biggest impact — now I run a tech publication! And it was a very, very interesting experience that shaped my reporting a lot as well.”



“It opened my eyes and the eyes of the reporters I’ve worked with on the positives and negatives of technology, and to see sort of the power that really young founders get early on and to really understand what issues are at play there.”



“I remember editors at the Journal started saying, oh don’t write about Facebook, they don’t ever make any money. There wasn’t an understanding of the ultimate business models that would propel these companies.”



“[Working for the college paper is] a good setup for life as a journalist, where you have to separate different parts of your life, and you take your job very seriously and you have to have the courage to kind of ask the tough questions.”



“You’re writing, and you’re getting published on the front page of The Wall Street Journal. And so I think after a summer of working hard, covering the economy, I just rose my hand for any opportunity, any beat. I tried to keep extending my internship with coming up with more and more story ideas that would let them not inactivate my key card.”



“I moved out right when Microsoft was trying to buy Yahoo, and Yahoo was on my beat, so I also, you know, quickly became probably a mediocre M&A reporter.”



“It was what I love best about journalism — a kind of the fast-paced, fairly competitive environment but where you’re writing about companies where there was tremendous interest.”



 “The audience that needs to know about these companies and wants to know is much broader than the people who are living in the Bay Area, and that’s fueled me and The Information ever since.”



“Tech companies like Facebook and Google have these rocketship online ad businesses, and publishers were chasing that instead of chasing, I think, building and monetizing audiences based on quality information.”



“This idea of building a business publication for a broad audience that specialized in technology and disruption, to me, became really essential if we’re going to serve the next generation of business.”



About starting her business: “I just couldn’t stop thinking about. It was not an easy decision. I think people in my life who went through it often remind me that I now make it seem too easy.”



“I think everyone thought I was just completely nuts but they weren’t saying that to my face. They were, you know, making me feel like they had some confidence in me and that was very meaningful.”



“People talk with journalists they trust and, frankly, who they find utility in talking to. People talk to journalists also because they want to know what the journalist is hearing, or they want to influence something that journalists just heard that they may not think is totally accurate.”



“As a subscription business it’s not about a magic number. But as a startup, are you getting better? We’ve managed to accelerate our growth rate as we’ve gotten bigger and I think that is. if anything, what I use to, kind of, guide, Are we on the right track? Are we on the wrong track?”



“All startup founders know, you’re basically the recruiter-in-chief at some point.”



“I love commentary. I think what the world needs more is, like, digging out cold, hard facts.”



“I want journalists to kind of be greedy in the sense of, like, if they’re delivering great content and great value that should affect their compensation. So I’ve enjoyed watching journalists kind of talk through the rationale for starting a newsletter by thinking about their earning power, because I think it’s healthy for any business to really align, okay what’s the value of the journalism, the value business and having that go to someone directly.”

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