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Feb. 4, 2021, 11:51 a.m.
Business Models

The Information’s Jessica Lessin built a newsroom she wanted to work in — and coaches other journalists-turned-founders on doing the same

“Frankly, the really hard part is the journalism. Everything else can be learned and shared.”

Jessica Lessin is all in on paywalls. The founder and editor-in-chief of The Information — an ad-free tech and business publication where subscriptions cost $399/year — has long been a vocal advocate for sustainability through reader-generated revenue. It’s something that comes up often in her interviews, the weekly column on media and tech she writes, and the formal (and informal) advice she doles out to other journalists-turned-founders.

Lessin left The Wall Street Journal to launch The Information in 2013 and retains full ownership of the profitable company. In the seven years since the first WordPress post, Lessin has been tapped for advice — particularly on recreating her publication’s envy-inducing subscription business — by newsy startups including The 19th, Punchbowl, and Rest of World. She’s mentored a dozen more emerging outlets through The Information Accelerator, half of which have at least one female founder.

Lessin is sharp, thoughtful, and downright bullish about what subscriber-driven journalism can do. The Information itself is planning a newsroom expansion in 2021, including a just-hired tech and media reporter covering antitrust and other regulatory issues. (Sure to be a quiet beat!) We talked about mentoring, the best advice she got as a new founder, and what matters more than building “the fanciest website.” My conversation with Lessin, edited for clarity and length, is below.

Sarah Scire: You launched The Information Accelerator back in 2017. Can you tell me how that’s going — and what changes you’ve seen in the last three years?

Jessica Lessin: There’s been a proliferation of outlets and entrepreneurs building new media businesses. I’ve felt that we’re on the cusp of a golden age for journalism and the news business, which has been a little contrary to others’ points of view about the space. But the combination of what technology allows a very small team to do and distribute and the importance of quality journalism right now has led to an explosion in writers and teams of writers starting very successful publications.

We’ve seen a huge uptick in the number of entrepreneurs we’re working with. In some cases, it’s a little more formal. In other cases, we host publications for Zoom calls. We had one last week on the very sexy topic of funnel optimization.

Scire: Are there questions that come up again and again? Are there some things that tend to keep founders up at night, in your experience?

Lessin: There are definitely some similar patterns — across teams that are just starting out or larger companies that are trying to pivot their business model and really embrace subscriptions. [Subscriptions] have been in our DNA for more than seven years so that’s usually why people come knocking on our door.

Everybody wants to grow fast. That’s expected, but how do you achieve the right kind of growth? Everyone knows you could slash your price and get a boost that day, but what’s the long-term path? Any startup is going to be very focused on the team and getting hiring right. That’s a big focus, as well. How to leverage — or not — the tech platforms is another recurring theme. When do you partner with Google and Facebook and Apple? When do you not? That calculus is a very different if you’re a smaller company or a larger company.

For me, what’s most exciting is to see the excellence everyone has when it comes to their domain in terms of reporting. Take Punchbowl, which launched a couple of weeks ago, as a new outlet in Washington. I’ve just been glued to them. The amount of news they’re breaking about dynamics in Congress every day is true journalistic excellence. Our expertise sits in in the world of technology and business, and it’s been fascinating to see others in other areas just crush it. A lot of my advice is around embracing that, and doubling down on that, and tripling down on that.

Frankly, the really hard part is the journalism. Everything else can be learned and shared. That’s the philosophy of how I approach advising these companies: “Let me help you get up to speed as fast as possible on everything else, as much as we’ve learned, so you can focus on the journalism.”

Scire: Are there times where you advise a news organization or new media startup against paywall or prioritizing paid subscriptions? I’m thinking of Axios writing that journalism shouldn’t be “an exclusive privilege” and pledging to provide free access to the majority of their content.

Lessin: I think it should always be part of the mix. There’s so many different ways to approach it and I think that gets lost in the conversation. Just as an example, we have some folks in the Accelerator that I think about often. Ashley [Woods] started Detour Detroit as a newsletter covering local news in Detroit and what she saw as the next generation of business there. She has some free content. She has a paid membership that — in different times — included in-person events. That revenue and support directly from her community is essential. Now, that doesn’t mean that people can’t access some of your content for free. But I think we will only achieve this goal of quality information in the world if we have a business model behind it. You can do 10 times more if you have a sustainable model.

I certainly believe in other models. The 19th [where Lessin serves as board chair] is a nonprofit but also has a booming membership program. That’s a key asset both in terms of revenue to support the journalism but also in terms of the community it’s building.

We have to get over this idea that membership and subscription models are premium or lock some people out. The problem I’m worried about most is that if we don’t have ways to pay and support and encourage professional journalists, the amount of professional reporting that’s going to happen is going to be diminished. I think we need to come up with great models and just because a publication has a portion of its revenue stream that is paid doesn’t mean that it’s locking out readers. I think you’d be hard pressed today to find a publication that doesn’t do that to some degree. I mean, even Axios now has a B2B subscription product. I’m encouraged that news organizations are exploring a bit.

Scire: Taking a step back, should individual publications worry about contributing to a situation where rigorous, high-quality journalism is only available to those able to pay for it? Looking at the information ecosystem at large, are you worried that many people will end up reading whatever they can find without a paywall, even if it’s misleading or inaccurate or funded by undisclosed interests?

Lessin: I think any leader in the news business, myself included, thinks about this all the time. The rise of disinformation in society is a huge problem and you don’t get into the news business unless you believe we need to fight misinformation. It’s very easy to say what’s outside of a paywall, what’s in front of a paywall, but the reality is, it’s not how news influences, right? Think of The Information or The Wall Street Journal breaking a huge story for, first, its subscribers and that story then getting picked up by dozens and dozens of outlets. Millions of people could get the information in that story even though the story was broken by a subscription publication. I think that when those big stories happen, the world is better off for it if people are getting the information they need.

Many people — and people I respect — say the rise of subscriptions has led to more partisanship in journalism. I actually think the opposite is true, if you look at the facts. The days of clickbait and sensational, ad-driven news models put us in this place. We have to be careful; you see subscription publications that have a narrowing of perspective because they’re catering too much to their subscribers. But the bigger problem for society and the bigger crisis around misinformation would be if we don’t have outlets breaking the real, important, true information. That’s the thing we need more of. If the story is important enough, everyone will know about it.

Scire: If I can ask you to generalize on what you’ve seen as an advisor, why does a new news organization succeed? Why do some fail?

Lessin: I think every organization I’ve seen produce really differentiated content is successful. I think it’s really that simple. It’s no different than asking,”Which of these 10 new video apps will survive?” What’s the differentiated value? I think the demand for journalism and for commentary is so great right now that there’s a huge market for content creators that are doing something original and important. I’ve seen so many businesses that double down on that succeed.

I think that’s a bit counterintuitive to people. I certainly know that when I started The Information, it didn’t seem like the world needed another tech publication. There were so many blogs and it just seemed like we were swimming in it. But what we saw is that that coverage was skewed, it was often hype-y, and it was not very deep. We found this huge open field of coverage no one was doing by digging and trying to get to the bottom of how businesses were actually doing. There’s a huge market for that. It really comes back to the originality of the journalism.

Most of the people I work with are building companies and teams — they’re not one-man shops. But I think you’re also seeing the rise of individuals go to platforms like Substack and others and the same dynamics play out there. The ones that are saying things that are unique and valuable are seeing very substantial audiences and ones that are not doing that aren’t. It’s kind of that simple.

Scire: Well, now I’m curious. What’s the worst advice you got when you were starting The Information? Or an example of pretty good advice?

Lessin: Oh, man, I got a whole host of it. I was coming from having been a reporter at The Wall Street Journal for eight years and knowing very little about starting a business. The thing that really sticks in my head is advice I got from one entrepreneur telling me to focus on the things I uniquely knew and experienced as a journalist that I thought I could fix. When you look at your business, you ask, “How are we going to be different?” You could build the fanciest website, you could have the biggest launch party, you could do 1,000 things. But his advice — which I think about all the time — was to take those things about a newsroom that you think stood in the way of doing the best journalism and try and fix those.

For me, it’s a small example, but I hated the fact that if I wanted a chart made, I had to email my data to some person who I’d never meet and there was no back and forth between me and the data journalists around building this visual that I think really explained my story. Again, it’s a very small thing, but it’s something that we could fix day one with how we structured our team. I also really felt like readers didn’t really want another, “Is this founder really worth $3 billion?” kind of story. They wanted to understand, “What is this business? Why are people using it? How is it making money? How may it make money 10 years from now?” It’s funny how often you go back to the same advice, even at our scale.

Scire: Since it’s been in the news a fair amount recently, can you talk to me a little bit about The Information’s social media policy for journalists? And how you communicate your expectations for objectivity or online commentary to your reporters whether it’s about the folks that they’re covering or, say, politics?

Lessin: I think this is a tricky area and I wouldn’t say my views are fixed in stone. In general, we take the approach that — and we remind our journalists that — sharing political opinions or, really, a whole range of opinions on social media could compromise your reporting down the line because someone may use that against you to show some bias. That may not be fair, and may not be true, but it’s out there.

As a publication that cares about our journalists’ reputations and protecting them, we can’t ignore the fact that if someone is really active on social media around certain causes or issues that could that could impede what they can report and it could also unfairly create complications for their team. Maybe you’re not covering that CEO that you’ve been critical of, but someone else is. We’ve asked our journalists to take that very seriously — and I think they do. It isn’t something I like to have black and white lines around. We put a lot of confidence in our reporters to understand the dynamics and feel grateful that they do.

Photo by Julie Mikos.

POSTED     Feb. 4, 2021, 11:51 a.m.
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