In 2013, Jessica Lessin, a reporter at Wall Street Journal, left the newspaper to start a competitive publication, information.
A few years later, her new newsroom had grown in nearly two dozen reporters and editors and reserved more than $ 20 million on sale after she discovered in a profile I wrote about the Times business of Sunday. She says she has doubled her editorial staff since then and has continued to stay profitable, with income growing 30 percent in 2024 a year earlier.
But it is her investments outside the information that is attracting attention these days.
Her company Lessin Media has put money in traffic lights, Ankler, former Business Insider Nicholas Carlson’s Dynamo, Kevin Delaney’s Works card and other titles at a time when the news business appears more gloomy than before. Lessin, however, is optimistic.
I was caught with the entrepreneur for her latest media bet, Racquet Magazine of Tennis publishing and what she thinks of the change of news. This interview has been edited and condensed.
This investment seems different from your others. How did you come to her?
I actually got acquainted with Racquet by a number of fans of the magazine. And it was like the strangest 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 wanted to buy the whole trade. And they are waiting for an event in the US Open. And I was like I want to go to it. And I want to read this great profile about the mental coach behind the tennis of the world no. 1.
It sounds like it was something that just hit you personally. I assumed you would be more focused on market sales and size and margin.
Absolutely absolutely both. I am absolutely everything about income and controlling your destiny and direct revenue of reconciliation, and which is the true north.
I have also always been about the founder who has the real expertise. And I think big media companies reject niches. They think they are very small. In all these investments, the criteria I am looking for is that there must be real income and a model of income that is direct and user -driven, where brands can control their destiny. But also a very passionate founder.
Tell me about the founder of Racquet.
Led is led by Caitlin Thompson, who is a tennis player of the Division I college, who, you know, if she does not have Novak Djokovic’s cellphone, she knows how to get it very quickly. And she too, so she’s an amazing player – I haven’t worked yet the courage to play it. I adore tennis. My whole family does. But I think it’s so amazing to see the authority she has in space, and she has a background as a journalist.
Subscriptions are a large part of your media thesis. Do all the companies in which you invest have that component?
Not everyone does. You know Nich Carlson’s new company Dynamo, in which I invested, I don’t think they still do, but all companies have plans and road maps.
Can we talk about it? Its start is focused on the video. I still don’t understand what he is trying to do.
You are trying to get me in trouble!
I’m not.
So I can tell you what tied me to Dynamo. Nich, who is a world-class editor that I have known since he was a technology reporter, came to me and said, “Look, when I was leading Business Insider, it was this thing that was working really well, but we could never spend enough time or enough attention-and it was really how to create a very high quality video.”
And as someone who was inside a big company and without great opportunities and went to start a start-when I hear it from a founder-a light lamp is just turned off. Dynamo wants to build a brand that is known for distributing quality videos about really important topics. So I love the vision, and I like it came from this spark inside Nich while sitting inside a larger news organization.
Isn’t it an expensive video to produce and create and modify?
No. I mean, you need to watch my Podcast video, and it’s very low. So it depends. It is definitely in some respects, but the editing equation is transformed by him I do not think he is at all a medicine, but of course on the editing side and on the side of the packaging, and in cutting things in different ways for different audiences, he is already transformative.
You mentioned that large media companies lack photography in warm publications. Is the future of news? Or at least one way to be successful?
Yes, absolutely.
So is it finished for the New York Times?
Not finished. The last I checked, the New York Times had a news essence and was growing by uniting many different things – some of which are warm. I mean, see the purchase of athletics. So I think the New York Times gets that. This is one of the reasons The business is holding up.
Good for us.
My pointing is for readers to expect expertise. And that is not changing because someone can go so deep online for nothing. And I think what the great media entrepreneurs are understanding now – after a decade of learning the wrong lessons on how to build media businesses – is that there is so much growth and opportunity and influence we can serve to those communities.
Are many inheritance news editorials focused on the old model?
I think many of the big media organizations have not completely received the memorandum. I mean, it is interesting to see Wall Street Journal integrate its technology coverage with its media coverage.
You are talking about how magazines Recently cut some technology reporters And he combined it with the media team.
Yes, of course, it comes to a landscape where there has been a lot of breaks from working through different teams and publications and is very sad. It’S’S’S ALMA MATER, there are wonderful people there. But what is so interesting to me is the idea of consolidating different thematic areas.
In information, our formula is just very different. It is going very, very deeply in the subject matter, in reporting the beating. I think the most ambitious, changing stories of the world come from gathering wires about companies and people and areas of expertise. And I worry, because I see many other newsrooms with very talented reporters, they put those reporters in very wide beats and similar to enterprises. How can we keep companies and executives responsible without that type of reporting day and day outside?
How would you manage the diary if you were to run the show?
I would execute it as the information. I mean, I built it because I felt that if you wanted to be the most authorized publication for business leaders, you had to do it this way. You had to deeply own very important coverage areas. I think it’s very challenging to go widely. The question is, what will they look like, the next 20 years in terms of what readers think they will be “should have” compared to a “beautiful to have?”
I think this explains the phenomenon of Substack. Very target content.
I think the idea of talent released from the old world of media is true, and I feel it because many of these people come to me for advice. People are understanding 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 print. And a decade plus later, there is an even lower grass to start.
But there are, like three, four or five things that you really need to get immediately in that, how, starting from who your investors are and what is your business model for the kind of things you focus on. And so is a role that I really like to play.
You have invested in seven media beginners. Will you make a flip?
I am very actively trying to make deals that will improve information and related to it – being the authority for technology – so roll such things within the information, absolutely. But most of our investments do not fit into that category. Just just trusting me so much in the founder and what they are building. But I am absolutely a believer who will be able for the information to receive a number of enterprises in many different areas.
So I will not see a summary of information, traffic lights and dynamo at any time soon?
You can see a great dinner for information-semapor-dunamo, and maybe even a tennis match.
The big media story is now The Washington Post, and since we are talking about investment opportunities, my old boss, Kara Swiser, is there trying to unite people to buy it. What do you think?
I texted him when I saw him, and I like, “You go!” I am all for passionate journalists trying to help form the future of news businesses. She is certainly one of them. I think she is also an expert, and I think she can get on the way of some types of journalism. But for people who really love news brands and love and want to form them, this is the type of transformation that will serve readers really well.
But there is no way Jeff Bezos will sell Washington Post.
Do you know something?
I have no information inside. I just think that Jeff Bezos is finally bending a little, and by that I mean his announcement that the pages of opinions would now reflect mainly “free markets and personal freedoms” or yet he said it.
Do you think it was a good action?
I believe that as the owner of a publication makes sense for them to form a perspective of their pages of thought. But it’s too early to say.
Let’s see what he writes.
Yes and this is not an action you do if you are trying to charge something. This is an action you do when you are placing yourself as the owner. He is really digging.
Maybe Kara has to go with her group of supporters and do something new that would challenge them. And then she has to call us to Lessi Media.