In 2013, Jessica Lessin, a reporter for the Wall Street Journal, left her paper to launch a competing publication, The Information.
A few years later, her fledgling newsroom grew into a reporter and editor for over $200,000, with more than $20 million in sales, as revealed in a profile she wrote for the Times Sunday Business. She has since doubled her editorial staff and continues to remain profitable, saying her revenue for 2024 was up 30% over the previous year.
However, what's been attracting attention these days is her investments other than information.
Her company Lessin Media put money into charter works and other titles by Semafor, Ankler, former business insider editor Nicholas Carlson, Dynamo, Kevin Delaney, and other titles when the news business seemed more obvious than before. But Lessin is optimistic.
I caught up with entrepreneurs about her latest media bet, tennis publication Racket magazine, and what she thinks about news changes. This interview was compiled and condensed.
This investment seems to be different from your other investments. How did you come to that?
I have actually introduced the racket by many fans of the magazine. And because I was reading a magazine, it seemed like the strangest experience, and because I wanted to buy all the clothes in the magazine. I went to the website and I wanted to buy all the items. And they are holding events at the US Open. And I seemed to want to go to it. And I want to read this incredible profile about the mental coach behind the world's No. 1 tennis player.
This sounds like something that hit you personally. I thought you would concentrate more on sales and market size and margins.
It's definitely both. I absolutely control your revenue and your fate and direct subscription revenue and it's about being the true north.
I've also always been on its founder who has real expertise. And I think the big media companies have rejected the niche. I think they are too small. Across all of these investments, the standard I'm looking for is that it needs to be a direct, user-driven revenue model where brands can control their own destiny. But he is also a very passionate founder.
Tell us about the founder of the racket.
This is led by Division I College tennis player Cait Lynn Thompson. And she too is a great player – I have not yet thought up the courage to play her. I love tennis. My whole family does that too. But I think it's very surprising 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 paper. Do all the companies that invest in have that component?
Not everything is. As you know Dynamo, the new Niche Carlson company I invested in, I don't think they are doing that yet, but every company has a plan and a roadmap.
Can you talk about that? His startup focuses on video. I still don't understand what he's going to do.
You're trying to trouble me!
i haven't.
So I can tell you what made me crazy about the dynamo. Niche was a world class editor who he knew from being a technology reporter and came to me and said, “When I was running a business insider, this was really going well, but I couldn't spend enough time, but it was a way to create it very efficiently from a cost perspective.
And as someone who was in a big company and saw a big opportunity and went to start a startup when they heard it from the founder, the light bulb went off. Dynamo wants to build a brand known for delivering high quality videos around very important topics. So I love that vision and I love coming from this spark in my niche as he sat in a bigger news organization.
Does it cost to create, create and edit videos?
no. That means you need to watch the video for my podcast. Very low quality. So it depends. Certainly in a few points, but the editing equations are transformed by AI. I don't think AI is a panacea at all, but certainly on the editor and packaging side, when you cut things off in different ways for different audiences, AI is already transformative.
You said that major media companies are missing out on photos of niche publications. Is that the future of news? Or at least one way to succeed?
Yes, absolutely.
So, did it end for the New York Times?
It's not finished. The last time I checked, the New York Times had a newscore and was growing up bunching up many other different things. Some of them are niches. So, look at the athletics. So I think the New York Times will get this. That's one of the reasons Business is enduring.
Good for us.
My point is that readers expect expertise. And that hasn't changed. Because everyone can go deep online anything. And I think what great media entrepreneurs are thinking right now is that after learning ten years of wrong lessons about how to build a media business, there is a lot of growth, opportunities and impact in serving these communities.
Does the Legacy Newsroom focus on older models?
I don't think many of the larger media organizations get their memos completely. In other words, it's fascinating to see the Wall Street Journal integrate coverage of its technology with media coverage.
He's been talking about how the journal recently cut tech reporters and paired them with the media team.
Yeah. Of course, it's in a landscape where there were many layoffs in different teams and publications, which is very sad. It's my alma mater, there are some amazing people there. But what's very interesting to me is the idea of integrating different thematic areas.
Info, our formula is very different. It becomes a very, very deep, beat report on the subject matter. I think the most ambitious, world-changing, and impactful stories come from gathering strings around businesses, people, and specialties. And I'm worried. Because we see many other newsrooms with extremely talented reporters putting them on a very spacious, corporate beat. How can you hold companies and leaders accountable without going out every day for such reports?
If you were running a show, how would you manage the journal?
Run it like information. So I built it because I felt that if I wanted to be the most prestigious publication for business leaders, I had to do this. You had to deeply own a very important field of reporting. I think it's very difficult to get around widely. The question is, what will the next decade or 20 years look like in terms of what the reader thinks they have to have, as opposed to “Is that okay?”
I think it explains material phenomena. Very targeted content.
I think the idea that talent is freed from the old world of media is real. I feel that because many of these people come to me for advice. People are aware of opportunities. This is how I felt when I started to get information. At the time, I didn't have to have a printed press, so I thought it was easier than ever to start a media company. And in more than a decade there's an even lower bar to get started.
But there are three, four, five things you really need to do right in between, where your investor is, and what your business model is like you're focusing on. And that's a role I really like to play.
We invested in seven media startups. Would you like to roll up?
I am very proactive and seeking to enhance information, and to enhance it, which is related and is an authority on technology. However, most of our investments do not fit that category. I'm the only one who really believes in the founders and what they're building. However, I absolutely believe that information has the opportunity to acquire many companies in many different areas.
So, am I always going to see the info, Semafor, Dynamo rollup anytime soon?
You might also see Dynamo's great information sema dinner party, and perhaps a tennis match.
The big media talk now is the Washington Post and we talk about investment opportunities, so my old boss, Kara Swisher, is trying to buy people together. What do you think?
I texted her when I saw it and I was like, “You're going!” I'm all for passionate journalists trying to help shape the future of the news business. She is certainly one of them. I think she's also a critic, but I think it can get in the way of some kind of journalism. But for those who really love news, love brands and want to shape them, it's a transformation that really helps readers.
However, there is no way for Jeff Bezos to sell the Washington Post.
Do you know anything?
There is no internal information. I think Jeff Bezos is finally flexing a bit. That is to say, his announcement that the opinion page primarily reflects “free markets and individual freedoms” or that he said.
Do you think that was a good move?
As the owner of the publication, I believe it makes sense for them to shape the perspective of their opinion pages. But that's too early.
Let's take a look at what he writes.
Yeah. And that's not the move you make if you're trying to offload something. It's the move you make when you're establishing yourself as the owner. He's really digging into it.
Maybe Kara should go with a band of supporters and do new things that challenge them. And she should call us on Lessin Media.
