In 2013, Jessica Lessin, a reporter at the Wall Street Journal, left the newspaper to start a competitive publication, the information.
A few years later, her young 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 Sunday company of Times. She says that since then she has doubled her editorial staff and remained profitable, with the turnover grow by 30 percent in 2024 compared to the previous year.
But it is her investments outside the information that attract attention nowadays.
Her company Lessin Media has put money in Semafor, the Anler, the former Business Insider editor Nicholas Carlson's Dynamo, Kevin Delaney's Charter Works and other titles at a time when the news industry seems more gloomy than before. However, Lessin is optimistic.
I caught up with the entrepreneur about her newest media bet, the Tennis Publications 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 get there?
I was actually introduced in Racquet by a number of fans of the magazine. And it was like the weirdest experience, because I read the magazine, and then I wanted to buy all the clothes in the magazine. I went to the website and I wanted to buy all Merchandus. And they organize an event on the US Open. And I was like I wanted to go there. And I want to read this great profile about the mental coach behind the tennis player of the world.
This sounds like it was something you just met personally. I assumed that you would be more focused on sales and market size and margin.
It is absolutely both. I am absolutely entirely about income and control of your lottery and direct subscription income, and that is the true north.
I have always been about the founder who has the real expertise. And I think large media companies reject the niches. They think they are too small. In all these investments are the criteria I am looking for, there must be real income and an income model that is direct and user -driven where the brands can control their own destination. But also a very passionate founder.
Tell me about the founder of Racquet.
It is led by Caitlin Thompson, who is a tennis player division I, who, you know, if she doesn't have a mobile phone from Novak Djokovic, she knows how to get it pretty quickly. And she too, so she is a great player – I haven't worked up the courage to play her. I love tennis. My whole family does it too. But I think it's so great to see the authority she has in space, and she has a background as a journalist.
Subscriptions are a large part of your media hose. Have all the companies in which you invest that component?
Don't all do it. You know that the new company of Nich Carlson, Dynamo, in which I have invested, I don't think they don't do that yet, but all companies have plans and road cards.
Can we talk about that? His start-up is focused on video. I still don't understand what he is trying to do.
You try to get me into trouble!
I'm not.
So I can tell you what Dynamo has affiliated. Nich, a world-class editor I know since he was a technical reporter, came to me and said, “Look, when I ran business insider, there was something that worked really well, but we could never pay enough time or enough attention and it was really how we could create very efficiently from a cost perspective, very high quality videos.”
And if someone who was in a large company and saw enormous opportunities and started a start-up when I hear that from a founder's just a light bulb. Dynamo wants to build a brand that is known for supplying quality video around really important topics. So I love the vision, and I think it's great that it came out of this spark while he was in a larger news organization.
Is video not expensive to produce and make and edit?
No. I mean, you have to watch the video of my podcast, and it is very low quality. So it depends on it. It is certainly in some respects, but the editing comparison has been transformed by AI I do not think that AI is not a panacea at all, but certainly on the editing side and on the packaging side, and to cut things in different ways for different target groups, AI is already transforming.
You said that large media companies miss the image 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 one I checked had the New York Times a news core and grew by bundling many different other things – some of which are niche. I mean, look at the athletic acquisition. So I think the New York Times will get this. That is one of the reasons The company lasts.
Good for us.
My point is that readers expect expertise. And that does not change, because someone can go so deeply online. And I think that some great media – entrepreneurs now pick out – after a decade of learning the wrong lessons about building media companies – is that there is so much growth and opportunities and impact that we can have by serving those communities.
Are legacy newsrooms too focused on the old model?
I think many of the major media organizations have not received the memo completely. I mean, it is fascinating to see how the Wall Street Journal integrates its technical reporting with his media attention.
You're talking about how the diary recently cut some technical reporters And combined it with the media team.
Yes. Of course it comes in a landscape where many have been fired in different teams and publications and it is very sad. It is my Alma Mater, there are great people there. But what is so interesting for me is the idea to consolidate different thematic areas.
With the information our formula is simply very different. It goes very, very deep in topics, in Beat reporting. I think the most ambitious, world -change, impactful stories arise from collecting string around companies and people and areas of expertise. And I am worried, because I see many other newsrooms with very talented reporters who place reporters on very wide and business -like beats. How can we keep companies and leaders responsible without reporting that kind of day out?
How would you manage the diary if you performed the show?
I would perform it if the information. I mean, I built it because I felt that if you wanted to be the most authoritative publication for managers, you had to do it this way. You had to possess deep, very important coverage. I find it very challenging to become wide. The question is, what will the next 10, 20 years look like in terms of what readers think that a “must -have” will be in contrast to a “nice to have?”
I think that explains the substit phenomenon. Very targeted content.
I think the idea that talent is being released from the old media world is real, and I feel it, because many of these people come to me for advice. People realize the opportunities. I felt so when I started the information. At that time I thought it had never been so easier to start a media company because I didn't have to have print presses. And a decade plus later there is an even lower bar to get started.
But there are three, four, four or five things that you really need, such as, such as, ranging from who your investors are and what your business model is to the kind of things you are concentrating on. And that is a role that I love to play.
You have invested in seven media startups. Are you going to do a roll -up?
I try to do very actively deals that would improve the information and that are related to this – the authority in the field of technology – so rolling up such things within the information, absolutely. But most of our investments do not fit in that category. I just believe so much in the founder and what they build. But I am definitely in favor that there are opportunities for the information to acquire a number of companies in many different areas.
So I'm not going to see a role of the information, Semafor and Dynamo quickly?
Maybe you see a great information semafor dynamo dinner party and maybe even a tennis competition.
The big media story at the moment is the Washington Post, and because we are talking about investment options, my old boss, Kara Swisher, tries to bring people together to buy it. What do you think?
I texted her when I saw it, and I had something like: “You're going!” I am entirely for passionate journalists who try to help shape the future of news companies. She is definitely one of that. I think she is also an expert, and I think this can stand in the way of some types of journalism. But for people who really like news and love brands and want to form them, is that the type of transformation that readers will serve very well.
But there is no way in which Jeff Bezos will sell the Washington Post.
Do you know something?
I have no information inside. I just think that Jeff Bezos is finally bending a bit, and by that I mean his announcement that the opinion pages would now mainly reflect 'free markets and personal freedoms' or as he said.
Do you think that was a good move?
I really believe that it is logical as the owner of a publication to shape a position of their mening pages. But it's way too early to tell.
Let's see what he writes.
Yes. And that is not a movement that you make if you try to discharge something. That is a movement that makes you when you establish yourself as an owner. He really digs in.
Maybe Kara should go with her band from supporters and do something new that would challenge them. And then she should call us on Lessin Media.
