The Information Age

Jessica Lessin (0:02)

The decision to go and build your own business is so personal, right? You have to really want to be the jack of all trades that is required to do that.

Dylan Byers (0:13)

Hello friends, and welcome back to The Grill Room. It is Friday, September 4th.

What a crazy week in media. If I needed any sign that summer is over, and we're back in the flow, this week delivered it. So many stories on the media beat. So I wanted to kick off today's episode with my partner, Julia, who is here with me. Hello, Julia.

Julia Alexander (0:39)

Hey, Dylan.

Dylan Byers (0:40)

And then we will get to today's main event, which is Jessica Lessin, the founder, editor in chief, and CEO of The Information, who's going to stop by, talk about her company's growth, record growth, according to Jessica. 13 years into that business's story. But first, Julia, honestly, like so much this week, I don't know where to begin.

I think the biggest story of the week, I think, is the Met Gala, Galeano, Anna Wintour clusterfuck.

Julia Alexander (1:19)

Do you think that's the biggest story? I was going to argue it was Pablo Torre being redeemed.

Dylan Byers (1:25)

Okay. Well, so this is great. Let's talk about that. And then, Dark Horse, we don't know yet, but Fox News on Thursday, just very abruptly parted ways with Maria Bartiromo. And we are, as you and I are talking, I'm in the process of trying to figure out what happened. All I know is they did not give her a sendoff. She hasn't actually been on the air for almost a month. She is not officially going to the Trump administration to be the new press secretary, although I suppose by the time folks are listening to this, Trump might have posted on Truth Social that that job is on offer.

That is potentially a huge story too, depending on why she left. But let's start with Anna and the Met, which I wrote about in depth this week for In the Room. I also talked about it with our partners, Marion and Lauren, on Lauren's podcast Fashion People. If anyone wants to dive into the world of fashion and New York High Society, jump over there. But yeah, to me, this is a massive story for one very simple reason.

There are a few people in any industry, certainly in the media industry, who have been as untouchable as Anna Winter. She, like, you know, you think about how long it took Bob Iger to retire, like Anna Winter has never retired. And in fact, she's expanded her remit, expanded her influence, not just over Vogue, over Condé Nast, and over, like, truly just the world of fashion. And the Met, which is, you know, sort of like the creme de la creme of public institutions and being a Met trustee is a BFD, she exerted a lot of power in that sphere. And I think that over the course of some four decades, she has become very accustomed to getting her way and watching people fall in line. And for whatever reason, she was so enamored with John Galliano. She was so, I don't know, obsessed was a word I heard often in the course of my reporting. Some people said she, you know, felt like sort of like either a big sister to him or other to him. She was hell bent, it seemed, on his rehabilitation despite a very well-known history of anti-Semitic remarks. And let's be honest, like these weren't subtle.

Julia Alexander (3:57)

Yeah, yeah, the remarks were-

Dylan Byers (3:59)

They're so terrible. I don't even know. They don't contain profanities, but I don't want to repeat them because they're so bad. Yeah. He has been involved in this rehabilitation process for like almost 15 years. And yet, and yet plenty of evidence that he actually had not been reformed. And reasonable concern among some Met trustees, certainly among the city's Jewish leaders, that this was a really, really bad idea. And Anna, again, who probably is not used to being told that she can't have it her way, somehow continued to try to press this through despite the mounting opposition of those leaders and those trustees.

And then finally was told, like, actually, no, you can't. And in typical Anna fashion, she and Galeana went out and got ahead of it and decided to resign before the event could be canceled, or pull out of the event before it could be canceled. But I don't know. To me, Julie, I just think there are titans in the industries we cover. She ranks high. If you say Anna, no one has to second guess who you are talking about. And lo and behold, in, you know, she's in her mid 70s, almost certainly getting on toward the end of her career.