Money·3 min read

Skimm'd from the Couch: Jessica Lessin

February 24, 2021

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Jessica Lessin has broken some of the biggest stories on the tech companies we all know  (think: Facebook, Google, and Apple). Now, after years of covering founders and entrepreneurs, she’s become one herself. She started The Information - a subscription-based digital media company covering technology and business. This week, she told us how her perspective has changed since going from employee to founder. And what she’s still trying to learn on the job. 

On Internships

Carly: One of the most popular questions that we get asked is, "How do I turn my internship into something full-time?" What is your advice on how to do that?

Jessica: Don't leave the building…. I say this and I still cringe a little, because it's clearly quite aggressive, but you know what, reporting requires being aggressive…. Every boss just wants to know is this person gonna be a great fit and contribute? And I think if you can demonstrate that, particularly at a company like ours where we're growing quickly and we need to hire more people, that's the best sorta ticket to any job.

On Her Work Personality

Carly: Do you have a work personality and a real life personality?

Jessica: ....My work personality is fairly impatient and to the point I think. And especially now when we're all just feeling pulled in so many directions, I'm not big on small talk. I'm not big on what I think I sometimes perceive as not wanting to waste other people's time. It's not so much that I think my time is this precious, but I know everything people are doing and that I'm asking them to do. And so I'm kind of all business.

….One of the things I miss about being in an office is actually I think the ability for people to see different sides of me, and me sorta different sides of them. But at the end of the day, we're in a competitive field. We are hyper-ambitious with what we're trying to do. And I like to get down to business, I guess.

On Being A Founder

Carly: I'm so curious about your experience of covering founders for so many years, and then becoming one yourself. What were the things that you realized maybe you didn't appreciate beforehand? How has your perspective shifted?

Jessica: I love this question, because it continues to shift and evolve. I think one of the first things was as a reporter I was so focused on just sort of news and getting scoops and stuff that I never really thought about what I think founders spend most of their time on, which is management and recruiting and internal stuff.

And so, you know, I think that is a good angle to kind of have, right? To understand how the leadership of companies big and small actually spends their time, and all the things related to that. You know, by the same token, as a reporter, if I see a huge amount of turnover at a company, that's a red flag. And I think it should be, but of what? I mean, sometimes that's a sign that a leader is fixing their mistakes or that they're just making a different strategic choice and making some hard calls. 

Many times as a reporter, you know, I see a story and a story is the facts point to some sort of story or angle that's really tough on the company or something that isn't working. And as a founder, I might empathize, but, you know, it's still newsworthy. And so, yeah, I think most of the time the dual perspective helps, but there are times it's at odds as well.

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