I wasn't going to be in journalism before I went to Columbia. I wanted to go into the government or military intelligence or CIA. I wanted to be an analyst. But I was gay and, at the time, it was just impossible. You couldn't do it without lying, and I didn't think it was a very good idea for an agent to be a liar, I had to find other things.

I had worked for the school newspaper at Georgetown and I did very well. I was the top writer and I won awards, and for various and sundry reasons, I ended up working for the Washington Post in college as a stringer and at night sometimes as a news aid. So that's how I got into it. Because it was my second choice.

I wanted to be an architect at one point, and I just shouldn’t have been. I'm an untalented person in that regard. I recognized in high school: I really can't do something I'm not good at. And I was very good at journalism from the get-go.

I always liked writing. I liked the fame. I like talking to people. I like the work itself a lot. And I liked being at the Washington Post, too. I had a lot of regard for it and when I started to see success pretty quickly, I was pretty happy. 

I took whatever work I could get at each section of the Post. I literally buttonholed editors and I said, ‘Do you need someone to fill in? Is there a maternity leave?’ And eventually, I went to the business section—which at the time was a backwater for the paper. I was interested in business and started writing about all kinds of things. I covered retail for many years, and wrote a series of stories on the Haft family, which was essentially a Succession story here in Washington, D.C. with a bunch of really mean people. It got me a lot of attention, but I didn't love the topic and I wanted to get off retail. 

At the time there was a little company called AOL and a bunch of other internet service providers. I started covering them. I was the young person on the staff at the time, so the editors would say, ‘You’ll take this, right? This seems young.’ And so I covered the internet at its beginning stages in the early 1990s. Nobody understood it, but I did. I understood the implications of it. And it was right away that I understood how important it was going to be.

They're not that different. There are still the same issues around privacy, surveillance, and monopoly. I covered the Microsoft trial in ‘98 with its monopoly. I understood the power of tech and that these companies weren't just, say, creating a monopoly in cigarettes or whatever the heck, they were custodians of our minds. Of ourselves. 

I reported with the premise that everything that can be digitized, will be digitized. And there would eventually be a digital self, that was you. I understood its power right away. It reminded me a great deal of the printing press or television. But again, a lot of people at the newspaper were like, ‘What are you covering that for?’ And I just thought, ‘The internet is going to kill you. You music people, you Hollywood people, you newspaper people, you're all dead. Lie down.’ You had no way of fighting it.

I'll tell you why I'm successful: I work harder than everybody else. That's it. I mean, you have to have a couple of things. You have to be persistent. You have to be consistently excellent. Don't cut corners. You have to do so much research. And I also am very good at seeing systems and linking things together that may not make sense to link at first. After all, I was going to be an analyst for the CIA and I was good at building scenarios and puzzles. So that's why I think I was good at journalism.

I was running a whole website [Recode] and then I said, ‘I'm not doing it anymore. I'm doing podcasting.’ This was eight or nine years ago. And I love podcasting. I love interviewing people. I love talking to people. It’s the best job in the world. I ask anybody any question I want, and they're challenging. They're like puzzles, too. And the purpose is to understand the real person. It's very hard to be tough on them and, at the same time, humane. It’s something I try really hard to do. 

Now I spend a lot of time doing things I like. Just today, I had a ball on a call about my podcast for Succession, I recorded a great podcast about Section 230, and I'm going to work on my book next. But if I don't like it, I stop doing it. No is a complete sentence

I wear the same clothes I wore when I was in seventh grade. So I, in fact, dress like a seventh-grade boy. I wear my sunglasses—the Ray-Bans—they're my look. I just like very simple clothes. As long as it's comfortable and I look good. I like to have good work clothes when I can, although now I've moved away from ‘hard pants.’ Is there anything even more comfortable? Whatever—people should wear what they want. If they like dressing up, good for them.

I'm very good at picking talent and seeing who has what it takes because I remember when I was not given that chance. Women aren't given that chance as much as men are. People of color are almost never given that chance. White guys get a pass—for some reason standards never apply. I'll give you a tech example: In 2013, I wrote a piece about the board of Twitter and it had 10 white men on it. The company was doing shitty and I asked the then-CEO, ‘why are there 10 white men on the board? How did that happen?” It's mathematically impossible that these were the 10 finest people in the land you can find. Half of Twitter’s usage was female, 30% at that time was African American. It was so obvious, if you looked at their demographics, they should have a more diverse board.

After my article was published, I came to ask the CEO why he didn’t have more people of color or women on the board. And he said, ‘you know, we have standards.’ It was right at that moment I said, ‘You had no standards for them. Everybody else gets judged differently.’ It’s like you get a tax if you're a woman, you get a tax if you're a person of color. You're assumed to be incompetent until proven otherwise. And white men are assumed to be competent until they're proven otherwise.

I'm super intrigued by video. I want to know why cable and television are so shitty in the news business. I'm fascinated by their travails. There is something brewing between TikTok videos and broadcast or cable news. You don't have to be stupid and quick and fast, but there's something very exciting going on at TikTok, Twitter, or Instagram Reels, and there's something not exciting going on with cable. And so I'm interested in why that is. I'm studying it, I'm looking at it, but I haven't come up with the solution yet.