How I Got Here: Jacob Weisberg

A conversation with
Jacob Weisberg

Feb 5, 2020

Feb 5, 2020 • by Jacob Weisberg

Jacob Weisberg

  • Writer, The New Republic 
  • Editor, Slate 
  • CEO, Pushkin Industries 

As a kid, what did you want to be when you grew up?  

I wanted to be involved in politics or write about it. I grew up on the North Side of Chicago, in a very liberal milieu. My dad was a civil rights lawyer, later a judge. My mom worked for the government. We thought of ourselves as middle class. When I was eight years old, I sold buttons for George McGovern on our street corner. I raised $5.25, and my parents took me to the local campaign office to give them the quarters I had gotten. I was amazed when Nixon was reelected, because everyone I knew was for McGovern.  

In Chicago in those years, the Daley machine ran everything. I grew up thinking that this particular form of local despotism was really wrong, that breaking its stranglehold was an overwhelming imperative. The heroes of my childhood were local people who resisted, including my dad. I actually went to the 1984 Democratic convention as an at-large delegate for [Chicago Mayor] Harold Washington. 

Did you work on student papers?  

I did, but that wasn’t how I defined myself. I was drawn to writing about politics more than reporting news. In college, I had a summer job working for Chicago magazine and another working for the City News Bureau of Chicago. And then I took a year off to work at The New Republic and had a great time. After that, I knew I was going to do journalism. 

TNR was legendary in that era. What was it like? 

Michael Kinsley was the editor when I first got there. The New Republic was just a terrific magazine back then. It was troublemaking; it was clever; it was in the middle of all the interesting debates that were going on inside liberalism and the Democratic Party, but with open-mindedness and insight that transcended the ideological boundaries of the era. It was a place where young people just out of college or even still in it had tremendous opportunity. If your stories were good enough to publish, they were treated more or less on a par with those of much more experienced journalists and academics. You got to sit at the table with distinguished intellectuals and political thinkers. It was a lot of fun. There was an atmosphere of naughtiness: TNR never thought of itself as part of the establishment. Particularly under Kinsley, it saw itself as a place that hurled spitballs at the establishment. And I fell in love with doing that kind of journalism. I went back to college, graduated, went to graduate school at Oxford for a couple of years, and then came right back to The New Republic as a writer and editor as my first real job. 

In retrospect, were those wonderful opportunities open primarily to white Ivy League males? And was the debate more constricted within centrist technocratic liberalism than you realized at the time? 

It was more diverse intellectually than sociologically. Michael Kinsley was, and is, open to a range of ideas in a way that is very unusual. As for demographics, it was even narrower. Almost everybody was from Harvard. I was an outlier in that I wasn’t a student of Marty Peretz [then owner of TNR who taught at Harvard]. 

Are you actually saying you were a minority at The New Republic because you came from Yale?  

Funnily enough, that was kind of true. They all talked about Harvard. I thought of myself as a kid from Chicago. I may have gone to Yale, but I wasn’t from the East Coast. I didn’t feel like I fit in. A friend of mine—Evan Smith, who now runs an important experiment in nonprofit journalism called The Texas Tribune—had idolized The New Republic and always wanted to work there. He finally got a job there a bit later. He felt like he was meeting all these great figures—Charles Krauthammer, Leon Wieseltier, etc. His disappointment was unbelievable. He realized these people were petty, had dark and ugly sides. And he couldn’t get out fast enough. 

How come you ended up staying? 

Because you could have the opportunity to write. And there were some wonderful people there, too. Kinsley, Dorothy Wickenden, Ann Hulbert, Hendrik Hertzberg. It was my apprenticeship in journalism. I learned how to write from them. I learned about politics. I’ve counted them as friends and mentors my whole life—the core group of people who actually ran the magazine. The slightly extended group beyond them, the feuding aunts and uncles, could give you a different impression. 

Your first New Republic cover story was about Roger Stone. 

I was a college student. I’d been there about a month. Kinsley assigned me to do a piece on this shocking character, Roger Stone, who I thought embodied the corruption around the Reagan administration, the merger of political consulting and lobbying. Roy Cohn was one of his mentors. He worked for all sorts of horrible people, and I thought he was the epitome of everything rotten. Mike had this idea of putting it on the cover, with the headline “The State-of-the-Art Washington Sleazeball.” I said, “He’s going to sue us or kill us or both.” But the headline and the image got everybody’s attention. 

What would you have said if I had told you then that Stone’s style would come to dominate American politics and that three decades later his and Cohn’s client, the real estate developer Donald Trump, would be sitting in the White House?  

That would have been preposterous. But in the late Reagan era, there was something going on around the merger of celebrity and politics, and new ground was being broken. I’ve since written a biography of Reagan, and I think I understand the reality of his career much better now than I did then. We’d never had an actor elected as president, and that paved the way for a reality TV star. 

In the mid-1990s, you left behind print to follow Kinsley into digital, at Slate, boldly going where no journalists had gone before. 

Robert Wright, one of the really interesting thinkers at The New Republic, had written this piece about how important the Internet was going to be. We all had these early versions of email accounts. I remember one of them: you would send someone a digital message on your computer, and they would then get it in the mail, printed out like a Telex. Kinsley was focused on the question of how magazine editors could achieve greater independence. Mike had been the editor of Harper’s, which was run by a foundation, and he was fired because he tried to do gutsy journalism. The New Republic was subsidized by Marty Peretz. Mike always used to say, “There are worse forms of subsidy. A rich guy has weird quirks and tends to interfere. But it’s not a giant corporation, and you can have a lot of freedom when the rich guy gets bored or isn’t paying attention.” But he was always chasing the Holy Grail of a magazine that would pay for itself. He had this idea that the Internet might be a way to do that.  

He was also frustrated by lead times. Weekly political magazines were sent through the mail. You would finish, go to press Wednesday night, and the earliest anybody got the magazine was Saturday. Most people got it the following week. In politics, even then, a week was a pretty long time. You would have your idea or your reporting that you were so proud of and walk on eggshells until your piece came out, because you didn’t want to be scooped or overtaken by events. It’s funny now to think you could write something that people would read a week later, and it would still seem original. I mean, these days an original thought lasts 45 seconds. We thought of the Internet as a quick-distribution mechanism. We’d still do a weekly magazine, which people would get digitally and print out and read in order. 

By that point, I was working at New York magazine, doing a weekly political column covering the 1996 presidential campaign, one of the most boring ever. Kurt Andersen was the editor there, another mentor of mine, formerly the editor of Spy, one of the brilliant editors of our era. He got fired—partly, I think, because of negative stuff I wrote about Bob Dole—and I quit. Mike had just started Slate, and I called and said, “I just quit my job in New York. Do you still have a job for me?” And he said, “Yeah, great. When can you start? How’s tomorrow?” 

Did you go out to Seattle?

I never moved out there, because I was still covering the campaign, so I was traveling with the candidates. Jake Tapper was then at Salon, and we were the first two Internet journalists to cover a presidential campaign. With Bob Dole’s campaign, in particular, you would try to get on the bus and they would say, “What’s the Internet?” But eventually, you could talk your way on. 

How would you describe Slate’s role in journalistic history?

It was one of the first Internet magazines. A new medium doesn’t come around very often, and the chance to be part of figuring it out was really exciting. We thought, “This is like the early days of TV or radio.” There’s a period when the rules aren’t established, when nobody knows what to do, and it was great. There were so many features that we developed just because we could, thanks to email and the Internet. We used to do all these dialogues, online diaries, breakfast tables, book clubs. We did the first news aggregation, “Today’s Papers,” which Mike and I came up with. Scott Shuger was the original writer of that. There were five national papers—The New York Times, The Washington Post, The Wall Street Journal, the LA Times, and USA Today—and they were all released at 11 PM Eastern Standard Time. He was on the West Coast, where it was only 8 PM, and he would work the night shift, writing a cogent summary of what each paper played as the big story. You could read the whole thing in five minutes before getting out of bed and have a real understanding of what the news of the day was. No one had ever done anything like that before. 

There was a great feature on Fridays on what you could talk about to sound smart over the weekend. 

“Cocktail Party Chatter,” by Jim Surowiecki. It’s had a few other lives since then. 

Did everything you tried in the 1990s work?

No. We tried writing a collective novel, with five writers using email. It was a fun experiment, but it didn’t catch on, and we didn’t do a second one. We tried a digital art gallery, but people were still connecting with slow modems, so it was too difficult to download. A bunch of the ideas we had were just too early; they relied on the kind of always-on, high-speed connections we got a few years later. That is the still underheralded tipping point around digital media and digital journalism—when large numbers of people got high-speed connections. They started to become standard in 1999, 2000, and everything became possible. Before that, we used to always think, “Is it too much bandwidth? Will people wait while this downloads?” 

You took over from Kinsley in 2002.

Yes. The Internet in 2002 was a different creature than in 1996, and it was different again in 2008. For Slate’s first few years, we were so innovative that we were ahead of the technology. We got a little complacent. And then The Huffington Post came along, which was the first digital publication to really take advantage of search and social media. And they became much bigger than Slate very quickly, and it was a wake-up call for us. The Huffington Post was never good journalistically. You would never hear people talking about their pieces, except the people who would tell you, “I wrote a piece on The Huffington Post,” which was like putting something on your Facebook page. But they were very innovative with the tools of digital journalism, the way they interacted with the audience. 

And HuffPost leads to BuzzFeed, and the monetization of Internet journalism starts in earnest and leaves Slate’s political journalism behind as an interesting, innovative journalistic story, but not one that captured the main monetary value of the Internet? 

It’s worth noting that The Huffington Post never made money. It achieved a high valuation based on the idea that it could someday make money, which as far as I know never happened. BuzzFeed became the place you could learn the most from if you were a competitor. But that’s a parallel story about how difficult it is to make money in journalism.  

Slate was originally backed by Microsoft, which insulated us and gave us a lot of freedom to experiment. We tried to make money, and we didn’t lose much. But we didn’t have to raise capital or satisfy investors, so we didn’t participate in the Internet boom-and-bust cycle. Slate always had around 30 people. Other early publications had gotten big as part of this frothy, bubble mentality; Salon at one point had 120 staff, with offices around the world. Then it all went kaboom. When the bubble popped, people became very skeptical about whether anything on the Internet could work as a business. The audience for Internet journalism was growing, but so was skepticism about whether it could ever be successful as a business. I came to the conclusion that Slate needed different ownership, that we needed to be part of a media company and not a technology company. And so I more or less engineered the sale of Slate to what was then the Washington Post Company, because I knew that Don Graham and the Graham family were the best stewards of journalistic businesses around. 

Where did you get the self-confidence to do that?

I was part of a group of people who were trying to solve a big problem—not just for our publication but also for the world, because independent journalism is the backbone of a healthy democracy, and figuring out how to make that work economically is a crucial issue. It didn’t really matter whether Slate made or lost a million dollars. But it mattered a lot whether independent journalism could support itself. So once I took over as editor, I had a strong sense of mission about trying to solve that problem—which remains fundamentally unsolved. The New York Times has more or less worked out an answer for itself, but nobody can say that there is a healthy, sustainable economic model for serious journalism as a whole. 

Michael Kinsley helped teach Bill Gates what it meant to be a good owner of a media business: that you could never interfere, you could never pursue your private agenda—basically, that if you wanted to be taken seriously, you couldn’t be Marty Peretz. Bill got that very quickly. He could be really annoyed by stuff Slate would write, including around the Microsoft antitrust case. But he understood that he couldn’t say anything, and couldn’t try to influence us, even if we overcompensated to try to prove how independent we were.  

When Gates went to work on his foundation, it became clear that Microsoft wasn’t really the best place for us. I didn’t know Don Graham, but I called the switchboard and asked for him, and he picked up the phone. And I said, “Would you have any interest in buying Slate?” He said, “I love Slate. Does Bill Gates really want to sell it?” I said, “I think he would, to you, under the right circumstances.” And he said, “Great. I’d love to.” It took a while to work it out, but Bill agreed to sell it to Don because he thought he’d be a good steward of it going forward—which he was. Don supported and invested in Slate for the rest of his career as CEO, and the Graham family proved to be the kind of owners that I hoped they would be. 

You went from being editor to being the head of the Slate Group. What did that involve?  

We washed up at the Washington Post Company at the beginning of 2005. I was still the editor but effectively also the CEO. I always thought the traditional division between church and state was a bad idea, because the business side and the content side needed to work together to solve the problem of paying for journalism. 

So a unified media operation is OK, as long as editorial’s in charge?

When the person who has business responsibility comes out of a strong background in journalism, it’s OK, because they have the right values. I always say that when people have integrity, you don’t need a detailed set of rules. And if people don’t have integrity, the detailed set of rules doesn’t help you. So the fundamental thing is for people to be focused on the principles of independent journalism. And those principles are that in an advertising-supported business, the advertisers don’t affect the content and you don’t confuse the audience about what is advertising and what is content. 

During those years, you gained ever-greater executive responsibility and became a suit rather than just a journalist. How did that change your perspective? 

That’s a good question, because if you’re a good journalist, you get promoted, and suddenly you find yourself managing people. But the thing that makes good journalists is usually a high degree of independence. The great reporter, classically, is a lone wolf who doesn’t necessarily work well in an office. So there is a flaw in the system. To gain the respect to run a big newsroom, for example, you need to have been a reporter, but the skills of running a big newsroom are not necessarily those of a reporter. I became the editor of Slate in my mid-30s. I’d never really managed anybody before and was very conscious that I had to learn about it. I didn’t go to business school, but I read a fair amount and talked to a lot of people. In some ways, the biggest influence on me was Bob Rubin, the former treasury secretary. As a side project, I’d written a book with him, and we talked a lot about management. He saw it as fundamentally psychology—understanding what motivates people and tailoring the way you manage them to their goals and ambitions. That influenced me a lot. There were also a lot of negative examples that were really useful to me, people I had seen manage badly, in a self-centered, thoughtless way. I was very conscious of some of the pitfalls and things to avoid. 

Do you feel a responsibility to make the field and the workplaces that you’re in better than the ones that you were in and experienced early in your career? 

Absolutely. And that started for me when I took over at Slate. The staff skewed male. I thought it would be a better environment if it were more balanced. I didn’t have a rule against hiring men, but I hired mostly women, and eventually, the senior management and staff became, if anything, skewed female. 

You make it sound so easy. 

It was easy. It is easy. 

So all the people who say, “We would do that if we could, but we just can’t find the people,” are not really trying? 

Certainly in that period, women were undervalued. You could find women who were better than men, and it wasn’t at all hard to hire them. It was harder to retain African American writers, because Slate was very much a training ground. We didn’t hire established talent; we liked to develop talent ourselves. And we hired a lot of terrific African American journalists. But they would make their name, become known at Slate, and then suddenly everybody wanted them. And it was very hard to retain people when they would get offers from The New Yorker and The New York Times

Has the Me Too movement changed your view of the institutions you were involved in?  

Yes. I was unaware of a lot of things that were going on around me. And also, particularly at TNR, I might have been dismissive of things or thought that they weren’t my business if they didn’t involve me. But we had a very different kind of environment at Slate. There was no Me Too scandal at Slate. We had a female editor during my later years there. There was a strong sense of equality and fairness. No place is perfect, but I think Slate was exceptional compared to some other media organizations.

In recent years, you’ve pioneered yet another journalistic revolution, in podcasting. What got you interested in that?

In the early 2000s, Slate formed a partnership with National Public Radio to create a midday show. They wanted something between Morning Edition and All Things Considered. I hired Andy Bowers, who’d been an NPR reporter and producer, to produce it. We had a really good time and got to do all kinds of crazy, fun stuff. But over time, the show became more conformist, more like the other things on NPR, and hence less interesting. Andy came to me and said, “The show’s getting less fun, but there’s this new thing called podcasting. I think Slate should start doing that.” I hadn’t heard of it but said, “Great,” and we started not long after that. Our first show was the Slate Political Gabfest, with John Dickerson, Emily Bazelon, and David Plotz. It’s one of the longest-running podcasts. All three of them have left Slate, but they still do that show every week, and I still listen to it every week.

Did you imagine when you started that it would be going strong nearly two decades later and would help pioneer an entire new industry?

Not remotely. But I did know that the people on the show loved making it, that there was a loyal audience, and that it didn’t cost much to make. There was always this fantasy in journalism that what was really interesting was the reporters talking to each other at the bar at the end of the day, and it would be great if you could figure out some way to capture that. That’s what the Slate Political Gabfest was, and still is. It’s the journalists telling each other what they really think and mixing it up and arguing. And the format we developed for that show, with three regulars talking every week, we then applied to culture, to business, to sports, to economics, and it’s one of the fundamental forms of podcasting that’s turned out to work.

How has the podcasting sector developed?

There was an early boom in 2005 and 2006. Twitter was originally a podcast directory company, before they pivoted and became a version of what they are now. Then the bottom fell out, and everyone gave up on it. We figured if we kept doing it and growing it, there’d be some revenue at some point, and that’s in fact what happened. People point to Serial [first launched in 2014] as the breakthrough show, but if you look at the audience growth, it’s more of a straight line. Apple putting an undeletable podcast app on iOS was the crucial thing. The term “podcasting” comes from the iPod originally, which is how people first listened.

You eventually decided to leave Slate and start a podcasting company. How come?

I’d started a podcasting company with Andy Bowers at Slate called Panoply. We thought of it as a content company, but it evolved to be more a technology company. The CEO I hired thought that the opportunity around technology was bigger, and he was probably right, but I wasn’t sure how much I had to contribute to a technology company. I was very excited about podcasting and had started a number of successful shows, including Revisionist History, with Malcolm Gladwell, who’d been a friend of mine since I was in college. I’d been thinking about leaving Slate someday. So I said to Malcolm, “Maybe it’s time.” And we started Pushkin.

What’s Pushkin?

We’re an audio publisher, a little more than a year old. We create editorial content—mostly podcasts, although we’ve just made our first audiobook, which is actually the audio of Malcolm’s new book, Talking to Strangers, which we produced like a podcast, with recorded interviews, archival sound, music scoring. We make shows that we want to listen to. We started Against the Rules with Michael Lewis, which made an interesting argument on the role of the referee in American life. We’ve just launched a show with Laurie Santos driven by psychological research into the science of happiness. A lot of podcasting comes out of the world of public radio. It’s firmly grounded in narrative and storytelling but tends to be less comfortable with opinion and argument. Malcolm and I come out of book and magazine writing, and the shows tend to have a different tone, more driven by a thesis or a hypothesis.

While you’ve been doing all of this, you’ve also had a separate career as a pundit and a writer. How did those paths intersect?

I’ve written several books, generally alongside other jobs. But in each case, I would take a couple of months’ leave. I like to write short books you can do fast. You can lay the groundwork, then plunge in and write, then finish up when you’re back at your job. But you can’t do that when you’re a CEO of a startup; it’s full-bore. I can write one or two articles. And I teach a course at Yale each spring term on the ethics of journalism.

What are you proudest of in your career?

I’m proudest of the work we’re doing at Pushkin right now. Everyone here is fired up and inspired about it. But I’ve loved every job I’ve had. When you’re not excited about it anymore, it’s time to do something else. I’m less proud of things I’ve written myself than I am of the people whose careers I’ve helped. I think Slate is a really good magazine, and I’m proud of that, but I’m really proud of the people who came out of it and who got their start there. That’s really satisfying, when you look back and say, “I was the first person to give that writer a place to write for a large audience,” the same way The New Republic gave me a chance to do that.

And your greatest regrets?

Gosh, I don’t know. I was at Slate a very long time. I had a lot of responsibility, and there wasn’t an easy way to separate myself from it. But I think I would have liked to have tried a few other things in that period of time.

Any advice for those starting out?

There’s never been a better time to be a journalist. The range of forms of storytelling is vast, and the opportunity for a young person to reach audiences everywhere is absolutely unprecedented in history. Journalism today has great economic challenges and is under attack in so many places around the world, including, shockingly, here in the United States. But there are fantastic creative opportunities. It’s very exciting!

This interview has been edited and condensed.