Why The Information’s Jessica Lessin sees subscriptions as the future of journalism

Melissa Hovanes
May 6 · 6 min read
Jessica Lessin, founder and editor-in-chief of The Information (PHOTO / courtesy The Information)

When Jessica Lessin founded The Information in 2013, people questioned whether readers would pay the $399 yearly price tag for the media startup’s coverage of the tech industry. Five years later, the publication reports having more than 10,000 subscribers, who also get access to exclusive events, conference calls and a private Slack channel.

After spending the fall quarter interning with the business team at The Information, I sat down with Jessica Lessin, the tech news publication’s founder and editor-in-chief. We discussed her experience creating a subscription news startup, her path to helping others start similar businesses and how transitioning from journalist to entrepreneur has influenced her understanding of journalism.

“To me [journalism] is uncovering the truth to help people better understand the world they live in,” Jessica says. “And readers can tell it — I don’t think we would be seeing the growth we’re seeing if ultimately readers couldn’t tell the difference.”

Here’s my interview with Jessica, edited for length and clarity:

We just celebrated five years of The Information. Congratulations! What do you think has made you so successful in the transition from journalist to entrepreneur?

It’s an ongoing transition. [The two jobs] are very different. There are some things [about journalism] that are directly applicable, like a desire and curiosity around gathering information. That’s the core of journalism, and I think that it has served me well as an entrepreneur because every day there are things I don’t know how to do, whether it’s how to approach recruiting for a certain type of role or how to approach new business opportunities. Having a network of people I know through reporting, and then being comfortable just picking up the phone and asking for their opinion has served me very well.

What has been the biggest challenge you’ve faced as an entrepreneur?

Very hard to pick one! Some things are relative. The things I have less experience in are harder. Figuring out what makes a great story, hiring great reporters and editing stories — that comes more naturally to me because I’ve been doing it for more than a decade.

It’s taken time to figure out what a great engineering team is at The Information and also what role I can play, or even should play, in that. If you go back five years, understanding areas I was less familiar with and how I could be productive in helping in those areas, and not counterproductive, was challenging and was sort of a calibration. We’ve been really lucky that we’ve managed to have built such an awesome team. That’s one of the upside surprises and is obviously critical to a lot.

“Getting existing and new news organizations to see [subscription] as a path for them is really important to me because I really feel it’s how premium content journalism will survive.”

You’re about to kick off another year of The Information Accelerator. How did the Accelerator come to be? What’s your biggest lesson learned from helping others to start new subscription news businesses?

As more entrepreneurs and existing folks in news were interested in subscription, they were coming to us for advice … I feel [subscription news] got a bad rap for many years online and that people didn’t take it seriously enough to see the possibility. Getting existing and new news organizations to see that as a path for them is really important to me because I really feel it’s how premium content journalism will survive.

That message was starting to pick up and people were asking us a lot of questions. And I felt frustrated. I could have a phone call here or there, but I didn’t feel like we were leveraging our time and expertise and serving people coming to us well. So I happened to be reading an article about Disney’s accelerator after one of these calls and a light bulb went off.

Jessica Lessin announces The Information Accelerator’s second class at their 2018 San Francisco Subscriber Summit (PHOTO / Melissa Hovanes)

We’re going into the second year. I’ve learned so much from it, but the piece that is really exciting is that all these businesses are very new. They may have a year or two under their belt.

We’ve had over 110 applicants to the program each year, so it’s been encouraging to see that the entrepreneurial interest in news is alive and well… We just had our wrap up call with the first class and there were a couple things people said that made me think I should take another look at that for our business. For instance, we haven’t done a lot of academic subscriptions. Those are working really well for one company, so I thought maybe we should take a second look at those.

There are big ways that it is very rewarding in terms of feeling like we can be helpful, and then there are some very small, practical ways it’s very rewarding in terms of the ideas we’re getting.

What would you say to anyone interested in applying for the accelerator?

We’re looking for expertise in a very specific content area and the ability to generate mastery standout content in that area. That might be breaking news on a certain subject. It might be just having a bead on things that are particularly relevant to a local community or focusing on topics that other people aren’t focused on. But we’re really looking for what’s original, what’s exclusive. The reason for that is it’s very hard to build a media company around content that’s at all commodity.

As journalists, we think our story is so much better than this other story, but in the eyes of a reader who is maybe not paying a ton of attention, it may seem similar. I always say, you really need to go for the 10x and focus on the things that are 10 times better or different than what other people are doing.

“We don’t really create marketing content besides our reporting.”

To me, your weekly newsletter sits at the intersection of journalism and marketing — you send a version to leads and subscribers. What’s your thought process around creating the newsletter?

The core of the newsletter is just my column, which is journalism. Sometimes it’s what’s on my mind, but other times I’ve spent hours reporting.

The marketing factor comes in when we send a version that has offers and some extra communication around it. I think this approach has made The Information successful.

We don’t really create marketing content besides our reporting. When we reach out to people who aren’t subscribers to tell them how to subscribe, we say, “Hey, did you see this story?” That’s basically our marketing strategy. We’ve found that the best way to get people to give us a try is to give them a taste of the product.

“But it’s important to share success stories and impact that places like The Information and many others are having because it points to the fact that this could be one of the best periods for journalism.”

One of my first assignments in journalism school was to define journalism. Has your understanding of journalism changed since you’ve stepped out of a purely journalist role into an entrepreneurial one?

No, I think it’s only deepened. To me [journalism] is uncovering the truth to help people better understand the world they live in. I’m torn about what’s happened in this world the last five years, but there are still great journalists doing that. There are a lot of journalists who aren’t doing that, and who are in it to make themselves famous or to get a lot of retweets.

Observing the fate of some of those businesses, which are going out of business or laying off people, has given me more faith and conviction in this pure sense of journalism. And readers can tell it — I don’t think we would be seeing the growth we’re seeing if ultimately readers couldn’t tell the difference.

I really hope young people still feel drawn to the profession, and I see plenty of evidence they do. Sometimes negative headlines around the business give people pause. But it’s important to share success stories and impact that places like The Information and many others are having because it points to the fact that this could be one of the best periods for journalism.

Digital has opened up a tremendous amount in terms of distribution. It’s led to the ability to have much more cost-efficient operations that can invest in people because you don’t have to invest in printing presses. So I see a lot of super positive signs, and it’s made me more excited by the day to do what we’re doing.

Melissa Hovanes

Written by

Software developer studying Media Innovation and Entrepreneurship at Northwestern Medill

Medill Media Innovation & Content Strategy / Entrepreneurship

One-year academic program for people who want to develop, launch and grow digital publications and media startups

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