In 2013, Jessica Lessin, a reporter at The Wall Street Journal, left the paper to start a competing publication, The Information.
A few years later, her fledgling newsroom had grown to nearly two dozen reporters and editors and booked more than $20 million in sales, as she revealed in a profile I wrote for The Times’s Sunday Business. She says she has since doubled her editorial staff and continued to stay profitable, with revenue growing 30 percent in 2024 over the previous year.
But it’s her investments outside of The Information that are gaining attention these days.
Her company Lessin Media has put money into Semafor, The Ankler, the former Business Insider editor Nicholas Carlson’s Dynamo, Kevin Delaney’s Charter Works and other titles at a time when the news business appears bleaker than before. Lessin, however, is optimistic.
I caught up with the entrepreneur about her latest media bet, the tennis publication Racquet magazine, and what she thinks about the changing news landscape. This interview has been edited and condensed.
This investment seems different from your others. How did you come to it?
I actually got introduced to Racquet by a number of fans of the magazine. And it was like the weirdest experience, because I was reading the magazine, and then I wanted to buy, like, all the clothes in the magazine. I went to the website, and I wanted to buy all the merch. And they’re hosting an event at the U.S. Open. And I was like I want to go to that. And I want to read this great profile about the mental coach behind the world No. 1 tennis player.
This sounds like it was something that just struck you personally. I assumed you’d be more focused on sales and market size and margin.
It’s absolutely both. I’m absolutely all about revenue and controlling your destiny and direct subscription revenue, and that being the true north.
I’ve also always been about that founder that has the real expertise. And I think big media companies dismiss the niches. They think they’re too small. Across all of these investments, the criteria I’m looking for is there’s got to be real revenue and a revenue model that is direct and user-driven where the brands can control their own destiny. But also a very passionate founder.
Tell me about Racquet’s founder.
It’s led by Caitlin Thompson, who’s a Division I college tennis player, who, you know, if she doesn’t have Novak Djokovic’s cellphone, she knows how to get it pretty quickly. And she also, so she’s an amazing player — I have not worked up the courage yet to play her. I adore tennis. My whole family does as well. But I think it’s so amazing to see the authority she has in the space, and she has a background as a journalist.
Subscriptions are a big part of your media thesis. Do all the companies you invest in have that component?
Not all do. You know Nich Carlson’s new company, Dynamo, that I invested in, I don’t think they do yet, but all the companies have plans and road maps.
Can we talk about that? His start-up is focused on video. I still don’t understand what he’s trying to do.
You’re trying to get me in trouble!
I’m not.
So I can tell you what hooked me on Dynamo. Nich, who is a world-class editor I’ve known since he was a tech reporter, came to me and said, “Look, when I was running Business Insider, there was this thing that was working really well, but we could never spend enough time or enough attention on — and it was really how to create very efficiently from a cost perspective, very high quality videos.”
And as someone who was inside a big company and saw huge opportunities and went to start a start-up — when I hear that from a founder — a lightbulb just goes off. Dynamo wants to build a brand that is known for delivering quality video around really important topics. So I love the vision, and I love that it came from this spark inside of Nich as he was sitting inside a bigger news organization.
Isn’t video expensive to produce and create and edit?
No. I mean, you should look at the video of my podcast, and it’s very low quality. So, it depends. It certainly is in some respects, but the editing equation has been transformed by A.I. I don’t think A.I. is a panacea at all, but certainly on the editing side and on the packaging side, and on cutting things in different ways for different audiences, A.I. is already transformative.
You mentioned that big media companies are missing the picture on niche publications. Is that the future of news? Or at least one way to be successful?
Yes, absolutely.
So is it over for The New York Times?
Not over. The last I checked, The New York Times had a news core and was growing by bundling lots of different other things — some of which are niche. I mean, look at The Athletic acquisition. So I think The New York Times gets this. That’s one of the reasons the business is holding up.
Good for us.
My point is readers expect expertise. And that’s not changing, because anyone can go so deep online about anything. And I think what great media entrepreneurs are figuring out now — after a decade of learning the wrong lessons about how to build media businesses — is that there is so much growth and opportunity and impact we can have by serving those communities.
Are legacy newsrooms too focused on the old model?
I do think that many of the large media organizations haven’t gotten the memo fully. I mean, it’s fascinating to watch The Wall Street Journal integrate its tech coverage with its media coverage.
You’re talking about how The Journal recently cut some tech reporters and combined it with the media team.
Yeah. Of course, it comes in a landscape where there have been a lot of layoffs across different teams and publications and it’s very sad. It’s my alma mater, there are wonderful people there. But what’s so interesting to me is the idea of consolidating different thematic areas.
At The Information, our formula is just very different. It’s going very, very deep into subject matters, into beat reporting. I think the most ambitious, world changing, impactful stories come from gathering string around companies and people and areas of expertise. And I worry, because I see a lot of other newsrooms with very talented reporters put those reporters on very broad and enterprise-like beats. How can we hold companies and leaders accountable without that kind of reporting day in and day out?
How would you manage The Journal if you were running the show?
I’d run it like The Information. I mean, I built it because I felt that if you wanted to be the most authoritative publication to business leaders, you had to do it this way. You had to deeply own very important areas of coverage. I think it’s very challenging to go broad. The question is, what are the next 10, 20 years going to look like in terms of what readers think will be a “must have” as opposed to a “nice to have?”
I guess that explains the Substack phenomenon. Very targeted content.
I think the idea of talent being unleashed from the old media world is real, and I feel it, because a lot of these people come to me for advice. People are realizing the opportunities. I felt this way when I started The Information. I thought at the time that it had never been easier, financially, to start a media company because I didn’t have to have any print presses. And a decade plus later, there’s an even lower bar to getting started.
But there are, like, three, four or five things you really have to get right in between that, like, ranging from who your investors are and what your business model is to the kind of things you focus on. And so that’s a role I really like to play.
You’ve invested in seven media start-ups. Are you going to do a roll up?
I am very actively trying to do deals that would enhance The Information and that are related to it — being the authority on tech — so rolling up things like that within The Information, absolutely. But most of our investments don’t fit into that category. It’s just me believing so much in the founder and what they’re building. But I am absolutely a believer that there will be opportunities for The Information to acquire a number of companies in a lot of different areas.
So I’m not going to see a roll-up of The Information, Semafor and Dynamo anytime soon?
You might see a great Information-Semafor-Dynamo dinner party, and maybe even a tennis match.
The big media story right now is The Washington Post, and since we’re talking about investment opportunities, my old boss, Kara Swisher, is out there trying to get people together to buy it. What do you think?
I texted her when I saw it, and I was like, “You go!” I am all for passionate journalists trying to help shape the future of news businesses. She’s certainly one of those. I think she’s also a pundit, and I think that can get in the way of some types of journalism. But for people who really love news and love brands and want to shape them, that’s the kind of transformation that’s going to serve readers really well.
But there’s no way Jeff Bezos is going to sell The Washington Post.
Do you know something?
I have no inside information. I just think Jeff Bezos is finally flexing a little, and by that I mean his announcement that the opinion pages would now primarily reflect “free markets and personal liberties” or however he said it.
Do you think that was a good move?
I do believe that as the owner of a publication it makes sense for them to shape a point of view of their opinion pages. But it’s way too early to tell.
Let’s see what he writes.
Yeah. And that’s not a move you make if you’re trying to offload something. That’s a move you make when you are establishing yourself as a proprietor. He’s really digging in.
Maybe Kara should go with her band of supporters and do something new that would challenge them. And then she should call us at Lessin Media.