Very Fine Day #9: Judd Legum

Brad Esposito

Judd Legum is a journalist, lawyer, and the former Research Director for Hillary Clinton’s 2008 presidential campaign. He is the creator of Popular Information, a newsletter about politics and power, and is the founder and former editor of ThinkProgress.

VFD: Alright, cool – we’re going, Judd. Thanks for doing this.

Just to start, how have you been? What have you been doing? I know you mentioned that in the last year you've had a lot of Zoom meetings. How has that been?

Judd Legum: I probably shouldn't complain. I don't really have too many Zooms, because it's just me and my research assistant for my newsletter. So we, most mornings, will do a zoom to talk about the newsletter,

VFD: Yeah,

Judd Legum: And I don't do a tonne of meetings, but there's always people who want to talk to you, or you want to talk to them. And sometimes I do those on zoom. So I should have enough practice.

But I shouldn't complain because I know that people with office jobs, who have to manage people, their entire day is just zoom after zoom after zoom. So I feel fortunate for that. Even my son, who's eight years old is on zoom all day. So yeah.

VFD: Do you have to help him set that up? Is that like… homeschooling?

Judd Legum: No, he knows exactly how to do it now. I mean, in the beginning he needed to figure it out. But now he's, like, an expert.

VFD: That's spooky. Watching kids use technology freaks me out because nothing makes you feel older than watching a seven-year-old log onto an iPad. They’re just like: easy.

So has the last year changed the way you work? I guess the nature of what you do is quite solitary. So like you said, you've kind of been lucky.

Judd Legum: I mean, it's changed it a bit, because I used to just go out to a coffee bar or something. I had a routine. So some of the routines have changed, because I used to, y’know, drop my son off at school and then I would go to a coffee bar and then hang out there. And I also had these, like, long stretches of the day where I really was alone just with my thoughts.

But now I'm here in my apartment with my wife and my son, and we're all sort of working all together. So I'm, like, never alone. Which is… it's hardly the worst thing that's happened.

It has been great in a lot of ways, because you get a bunch of experiences that you wouldn't have had when everyone's busy with moving around the city in their lives. So it has been a change, but ultimately it's not like the barrier that it is for a lot of people. But also, because I don't do the kind of work where I have to get out and necessarily meet people or go to places. I mean, I never did that really anyway.

VFD: So are you in New York City?

Judd Legum: DC.

VFD: How long have you been in DC?

Judd Legum: Since 2000,

VFD: Oh, wow. OK, yeah. That's a good stint. And you were brought there for work? College?

Judd Legum: I came initially for law school. So I did that for three years. I don't really know why I went to law school, but I just did. And so I came here for that and went to Georgetown,

VFD: You say three years… What's a regular stint at law school?

Judd Legum: It's a regular stint. That's how long it's supposed to take: three years. It really shouldn't have to take three years. I did practice law for a couple of years in between doing online political writing and stuff, so I know that you wouldn't actually need to spend three years in law school in order to practice as a lawyer, but that's how long it takes.

VFD: Did you have a moment where you realised that being a lawyer was probably not the 30 year career you wanted to have?

Judd Legum: Yeah, I think I really always knew that. Especially, like, while I was in law school. My interest has always been in politics. I mean, from when I was a little kid, really. So I sort of figured I would do something like that.

I never really figured I would be writing about politics. That's never something I was that interested in or thought about. But I think – probably deep down – I knew that I didn't have it in me to just practice as a lawyer for my whole career.

VFD: Yeah. What was your first move into politics?

Judd Legum: In… 1997.

VFD: Oh, wow.

Judd Legum: I was – this was sort of my first official position, I would say – but in 1997 I was an intern for a congressman named Elijah Cummings, who actually recently passed away. But he was a congressman from Baltimore.

It was a really interesting experience because he was a member of the Congressional Black Caucus. And then as his intern, you were part of the Congressional Black Caucus. And I was the only white person in the entire, like, cadre of that… but they had this amazing programme with these special speakers and tours of the Capitol. I mean, it really opened my eyes to a lot of stuff that was going on. And I think that still informs a lot of my perspective. That was interesting.

VFD: How'd you get into that? Was it just, like, a job application? How do you become a political intern?

Judd Legum: I think it's more difficult these days, to be honest with you. At the time, there was a guy from my hometown where I lived in Annapolis – Carl – and he ran for local office and stuff. And he was just friends with my family, and I would help him out. Like, he would be doing stuff… going to an event or whatever. I guess “helping him out” is not the right way to describe it, I would just hang around with him as he went about his day doing local politics stuff.

And he knew congressmen Cummings. And so he suggested it. He said, like: it would be a good thing for you to do, you should go intern there. And I think he called me or something and just said: Oh, yeah, I talked to him. And it's fine. It's set up, just write them a letter and tell them you're coming. So that's what I did. I just wrote… I remember in college that I sort of wrote up a letter. I talked to Carl…

VFD: And then it just happened? It's like, did you just show up and you were like: I'm here! Did you hear back from them?

Judd Legum: I can't remember… I must have heard back from them or something. They must have, like, written me back. It was really all via letter. I didn't email anyone. I remember that. Like, I didn't email anyone. I didn't call anyone. It was all via letter and I think they may have sent me a letter back telling me what day to start.

VFD: Right, OK. So doing the math in my head – you did that, then law school, and then you said you practiced law for for two years… Does that bring us to starting ThinkProgress?

Judd Legum: No, actually, I started ThinkProgress first. OK – So basically, when I was in law school, I became a research director for John Podesta, who at the time was famous for being Bill Clinton's chief of staff. He later became famous for getting his emails hacked.

VFD: Yeah… bit of a big name now.

Judd Legum: But at the time he was still well known. So I became his research assistant – he had just advertised in the law school flyer, or whatever, that he was looking for research assistant.

And so I was his research assistant for three years while I was in law school. And then when I was graduating, he was starting the Centre for American Progress, which is a centre-left thing. And he just asked me. He was like: Hey, do you want to come in and do this with me? Without any real description of what I would do. But I was just like: OK, I'll do that.

And so then I was there, and there was, like, 12 people there when I started. And I started a newsletter. That was the first thing I actually did there when I started – And then that's when blogs were really taking off. And I just got really interested in blogs and started reading and was like: Whoa, this is, y’know… this was interesting, because people could just get their opinions and ideas out at any time.

VFD: Yeah.

Judd Legum: And then I kind of pitched the Centre for American Progress – I pitched Podesta and said: Hey, we should start our own blog here. So that's how that started.

VFD: What was it like starting a blog back then? I guess, like, my own experience with the internet as a whole is pretty much only the social internet. Whereas starting in… what was this? ‘04, ‘05, early 2000s?

Judd Legum: Yeah.

VFD: How did you get stuff to take off, or get people's eyes on it, or make something successful? Because it seems like it must have been a lot harder. That's my guess.

Judd Legum: Well, that was the cool part about it, right? Because the blogosphere itself was social. So there was a network of folks and you would link to each other’s stuff and refer to it. And that's how stuff moved around.

So like, it wasn't getting stuff on Twitter, it was like… this is still around: Atrios. It was like a political blog – a liberal political blog. And he was like the first Twitter, because he would blog and his posts would be one sentence long, right? So if you got a link on his blog, that helped you be successful.

CNN had a little segment each day where they would say “Around The Blogosphere”, and they would highlight good blog posts that day.

And I remember we would gather around the televisions and be like: Hey, we were on today!

So that's what it was like, but it was very social and collaborative in a way that I don't think has really been replicated by social media. Really. I mean, it sort of is that way, but it's so… it's kind of just more competitive, I would say.

VFD: Why do you think it's harder? Just because there's more people in the schoolyard, I guess?

Judd Legum: Yeah. And in some ways the stakes seem higher, for some reason. And there was a spirit… I guess there was the feeling of a spirit of camaraderie, y’know? At least among the people who were generally doing the things that we were doing.

I think there was a feeling that we were all kind of helping each other. I don't know if that really exists too much among groups of people online now.

VFD: I think there was probably a 2007-2010 podcast version of that. And there was probably, like, a two month newsletter version of that maybe two years ago? But yeah, like you said, the competitiveness of it is… I guess it’s the creator economy. Everyone wants to make something for themselves.

So with ThinkProgress, what was the remit and goal when you started when you were there? And then you were there for two years, right? And then came back later?

But in that two years, did you feel like you'd set up what was planned?

Judd Legum: Yeah, it evolved over time. Y’know, I think the initial concept was: At the time, it was like, all opinion on blogs. Which was interesting. I mean, I was reading all of the time and it was interesting. But I noticed that there wasn't that much of people trying to dig up stuff. And I really didn't know how to do reporting then, but I knew research. So that was the idea. This would be a research blog, and we would find new research bits and put them on the internet. So that was the concept. And it just kind of developed over time.

I mean, one of the things that we did early on that was super interesting and was hugely important for our success was just picking something that happened on TV, like some dumb thing that somebody said, and clipping and figuring out a way to get it from your TV - this was before YouTube or anything - from your TV on to your blog.

And I remember we had someone there create a custom system for us to do this. We couldn't… there was no place to upload it and just embed it. Like, we had people who knew what they were doing to like, create some crazy system. And it took like them a couple of months to do it. But once we did it, we were like: Oh my God, we can now put stuff from TV onto the internet! And it was amazing. Like, people were losing their minds because they're like: Oh my God, someone said that on CNN today??

So that was very interesting. Now over time, that became very boring, because everyone's doing that. And today, it's sort of almost one of the lowest… there's nothing wrong with it, but it's just that no one thinks you've done something interesting if you've done that, right? It's just, like, standard internet fare.

VFD: Yeah, totally. You ever think back to that time like: Well, we could have made YouTube! We had it all there and we didn't do it!

Judd Legum: Yeah, I mean, so many things. So many things. I'm sure things are happening exactly right now that are passing us by. But yes. You know, people forget that YouTube is not… it wasn't so long ago that there really wasn't that much video on the internet. Crooks and Liars was another blog back at that time doing similar stuff,

VFD: Is that still around?

Judd Legum: I think they're still around. Yeah, I think they're still around. But they were, like, a blog that only did video. So they were really known for it.

VFD: Right.

Judd Legum: And they did it before we did, but then we figured it out. And we had more people so we could watch more TV shows. And we were able to get a lot of good stuff, y’know, just by watching TV.

VFD: So then when you left ThinkProgress after two years, was that a conscious decision where you're like: I'm kind of ready to move on.

Or was that a decision where someone came to you and gave you an opportunity?

Judd Legum: Yeah… the Hillary Clinton campaign basically came to me and asked if I wanted to be the research assistant.

VFD: How does that happen? Do you get, like, an email? It's like: “”. And she's like: Hey!

Like, what is this process? Because I find it interesting - the entry points into politics. I think a lot of people don't really understand that.

Judd Legum: I think it started because - well for one thing, just, y’know, obviously [John] Podesta is part of that world and everything. But that's not really how it happened. Because I don't think he was ready for me to leave CAP at that time.

So, we did a bunch of reporting on this ABC News special called “Path to 9/11”. And, y’know, at the time this was a big thing that was being discussed on blogs: Who was responsible for 9/11. A lot of that information was coming out around that time.

But there were a lot of problems with this documentary. And so what we were doing on the blog is reporting on those problems. And I think that we attracted the notice of the Clinton folks, because they saw that we were actually pretty effective at pointing out the errors in this and then getting them to fix them and put different kinds of disclaimers. So I think they sort of saw that operation as something they wanted to kind of translate over to the Hillary campaign.

VFD: So it was just you? Or was it a few people that went?

Judd Legum: No, it was just me.

I mean, once I got there, I had to hire a bunch of people. Maybe 30 people, y’know, doing that. And once we got there… I mean I couldn't really take any of the others. We just had a small team. And so I couldn't really… it was bad enough that I was going. I couldn't take the team also.

VFD: What was that like? I guess… maybe emotionally, but to go from “kind of media”, to “law media”, and then, like, into politics. And really into politics, right? Because Hillary was getting ready for a presidential campaign – or a go at it. And it feels like there would be a lot more pressure in that role you had, and a lot more responsibilities – or different responsibilities.

Judd Legum: Yeah, it was definitely much more intense. And I'll probably never work that intensely, like every day, no weekends, just straight through for that period of time.

I don't really mind working, but that was a grind. And the stakes were very high, just because it was Obama versus Hillary and like, no one was really interested in the Republican primary. Y’know, it was just like… it wasn't as interesting. And so everything that the campaign did was just highlighted. Any mistake you made was just highlighted and repeated.

VFD: That sounds like a really fun, relaxing, kind of environment to work in.

Judd Legum: It was not. It was not at all relaxing. The only relaxation I would do is we had this big - the headquarters were in Virginia - and they had this big building that I think used to be an immigrant detention facility or something. Like, it was very… brutalist architecture. But they didn't quite have it filled up because this was just the Primary.

So the idea was, I think we had half the building full of people. And then the idea would be, hopefully, if you won the Primary, which of course she didn't, but if she had won they would have filled up the other two floors. So if there was any downtime during the day, I was always so tired. I would go to one of the empty floors into an empty office and just like rest my arm and curl up and sleep for half an hour. That was the way I would relax.

VFD: Was there a particular moment where the scales begin to tip and yourself and the rest of the team began to realise that Obama's sailing away here. What do you do when you notice that? What happens within a political team when they notice that and it's writing on the wall? Or is it just: we keep going until it's absolutely done.

Judd Legum: Well, it’s interesting, because the time that it seemed like that happened was after Hillary lost Iowa, right? And I mostly just stayed at the headquarters. But I was also involved in the preparation for debates.

So once the Iowa caucus started, I was kind of on the road a little bit because I had to be there for the prep, because I was supposed to know what the other attack lines were going to be from the other candidates. So they had me out there because she wasn't going to be coming back to do prep or anything.

So I was in New Hampshire for a few days and there wasn't that much time between Iowa and the New Hampshire Primary. And I remember it was just like a funeral. Like, there was a pit in my stomach. I was feeling sick. Because it just sort of seemed like… I don't know why I was feeling sick. It was hardly like the world was ending. But you put so much time into it and everything, you sort of seem like: this is horrible. Everything's going wrong. And then she won! And it was like: Oh my god… it's amazing. You know: it's a miracle. I thought she was gonna lose and it was just like from being at a funeral to jubilation. But then it kind of slowed over time and obviously it went the other way.

So there wasn't one blow. But there was a moment when you thought it was happening. Then all of a sudden she was on top of the world again and then… the death was more of a slow death.

VFD: And are these jobs, like, contract jobs? When it’s over do you need to find something else to do? Or was that a decision you made?

Judd Legum: I mean, it was a decision that I made afterwards. Because obviously, I think for a lot of a lot of politicians, if they lose it's just like the whole thing packs up. For somebody like Hillary Clinton, she obviously kept up an operation.

Jake Sullivan, who's the National Security Adviser, he was involved in all that. He just stayed on and was with her by her side when she was Secretary of State, and y’know, just kept going. And now he's National Security Advisor. But as I was saying, it was very intense. I was just like: I think my time was over. Y’know: this isn't what I want to do.

VFD: Did it make you realise things about politics that you didn't know before? Did it turn you off?

Judd Legum: Yeah, I mean, one thing you realised is, when you’re so close to the centre of everything, things are so intense that you lose a lot of your agency, right?

Like, I can't just talk about what I think when I’m Hillary Clinton’s researcher. Because it all gets attributed to her.

VFD: Yeah, yeah.

Judd Legum: It's not really her fault – it's not really anyone's fault, necessarily. But when you have a position like that, you can't do it. And I just realised that I don't like that.

I don't like feeling constrained like that. You do have power, I guess, because you can be like… I could suggest a line that maybe gets used in the debate and millions of people see it or whatever, but it's not my line. It's somebody else's, right? So I didn't like that as much. It sort of felt too constrained to me.

VFD: So then what did you do after the Hillary campaign?

Judd Legum: Well, then I got in my head that I was going to run myself.

VFD: So you weren’t that damaged by the Clinton campaign…

Judd Legum: I mean, I don't want to… Yeah, I wasn't damaged. But I was thinking about where I would fit. So then was like: I'm gonna be the candidate.

So I moved from DC to Annapolis where I was from, started practising law with my dad, because he has a small firm in Annapolis. And just got ready to run for state delegate, which is basically the equivalent of like, the House of Representatives for Maryland.

VFD: Sure.

Judd Legum: So that's what I did.

VFD: And how was that experience?

Judd Legum: It was also very hard. I actually – I know we talked about it before, but I actually did enjoy a lot of practising law. I got to do a lot of criminal defence work. That was really interesting. Some of the other stuff… we also did, like, civil litigation. When people get in an accident and things like that. I was just like: I don't really care that much about what happened in this accident. I think that's what I sort of realised. But the running for office was really interesting. I knocked on 10,000 doors, talked to a lot of people in the entry way to their homes, basically,

VFD: What would you say the percentage rate is of people saying: Yeah, I'll talk.

Judd Legum: Gosh, maybe… one in….. I mean, it depends on when you're doing it, right? Because if you're doing it at a good time, when people are home, maybe one in four open the door. And then maybe – and most people are polite – but maybe only one in five of those are gonna talk to you for more than 10 seconds.

So if you're getting one in 20 with a five minute conversation, then the problem becomes you get somebody who really wants to talk, but you don't really want to talk to them for an hour, right? You just want to talk to them for like, a good, two - three minutes so they like you. And then you want to get out to your next door, because you're trying to get as many doors as possible.

So it's sort of like there's a fine line because you definitely get to people. You definitely get people who just… they've been waiting, probably their whole life, just for someone to knock on their door and want to talk to them about politics, and they've got a lot of things to tell you. And you're just like: I don't have time for this, this is gonna wreck the whole plan of my afternoon.

VFD: I think I would struggle with that. I think I'd be in a lot of four-hour conversations. Well, maybe just listening sessions where I have someone just going…

Judd Legum: Yeah, I found that I actually like the doors because you kind of got a sense of people's lives a little bit. Like, what they were doing. Even the people who are angry that you came; you just got a little window into them. It was really fascinating.

The things I didn't like were political events where you go into a room and it's all just a bunch of political people like you, but your job is to just talk to as many people as you can. That was kind of was draining, because it just wasn't interesting, because you had seen all of these people before.

VFD: So did that work out?

Judd Legum: I mean no, I lost. I was able to get through the Primary. It was kind of a complicated type of election where there were multi-member districts. So you had three Democrats and three Republicans, one advances through the primary and then the top three vote getters.

So I came kind of close, in terms of my vote total, but I didn't get it. It was a tough year to run as a Democrat. And the whole theory didn't pan out of how I was going to win. So I lost.

VFD: And then you went… it was back to ThinkProgress? Was that transition someone saying: Hey, it's time. We've been waiting…

Judd Legum: I knew I didn't want to run again, because I really didn't want to raise the money. Like, yeah: that's the worst part. Just calling people up for money.

VFD: Yeah.

Judd Legum: And I just didn't want to do it. So yeah, I think I went back. I just started talking to people because I would need a job. I knew I didn't want to keep practicing law, or stay in Annapolis if I wasn't going to be involved in politics there. So I moved back to DC.

And I talked to Podesta again. And actually, at the time, he was saying they really need someone to come back and develop the social media, because it was 2011 and they really didn't have a built out social media programme. So he asked if I could do that, for ThinkProgress and for CAP overall. So that's how I kind of came back.

I don't know why. I didn't really necessarily do too much with social media at that time, but I guess they just figured I could figure it out.

VFD: Yeah, yeah. And that was during that time, I think, when all the algorithms were pointed towards media platforms, and publishing, making some of them very good and very successful. And y’know, getting us to tie business models to social media, which is… an interesting move.

Judd Legum: Exactly. I looked like a genius. And for the first few years, it's like: wow, we brought you in to do social media, and all of a sudden, traffic's booming…

VFD: Did you believe it? Because I look back at when I was at BuzzFeed. And there was a period where I was like: How the hell is this getting 2 million views or getting this many shares on Facebook? You can't be serious.

But did you ever have a moment like that, where you're just looking at these stats and going: Really? That's how successful our content is? Is our content that great?

Judd Legum: I think I probably should have said that. I don't think I did. I just thought, like: wow, we've really figured it out. Like, I wasn't even thinking about it. Everyone else was also having success. I was just like: we're really doing well.

But I think later I realised, y’know, when you can see them sort of pull the rug out from under you and in a second everything crashes to the floor. That's when I thought about it. About how it was kind of artificial.

VFD: Do you consider yourself a journalist now then? And back then?

Judd Legum: More recently, now I do.

VFD: Right

Judd Legum: It took me a while to think of myself in that way.

VFD: What was it? What were you before then?

Judd Legum: I always thought of myself more as like a researcher.

VFD: Sure.

Judd Legum: Honestly. But eventually I moved back in to be the editor. You know, when I first came back, my friend Faz, who actually was just Bernie Sanders’ campaign manager, he was the editor. But he left - he was there for a couple years, we worked together - but then he left and then I became editor again.

And just because a lot of the research stuff, the pulling clips off the TV, all of that became less interesting because everyone was doing it. That's when we really started shifting ThinkProgress to do more journalism. Like: Let's hire journalists, let's do investigative reporting. Let's send people like that. We started to be like: send people to Iowa, let's send people to CPAC, let's send people to wherever is going on.

We used to bring those flip cams initially. This was before people had iPhones. I mean, I guess iPhones were around, but nobody really had an iPhone. So we'd send people with those cameras and record stuff.

And so then, as I'm sort of surrounding myself with journalists, then I sort of started thinking of myself that way a little bit more. But then really it was more when I left and all I'm doing is writing and reporting, and I don't really have any other agenda other than writing about stuff that I think is important. Then I started thinking of myself that way.

VFD: So you leaving ThinkProgress was 2018 right?

Judd: Yeah

VFD: Why did you leave?

Judd Legum: Primarily because what had happened was… we started doing well, and then as a result, we grew. And so when I left to the Hillary campaign, it was like a team of five people. And then when I came back, there maybe was 12 people, but then we had grown to almost 40 people.

And I just found that my whole day was managing personnel, hiring, managing interpersonal conflicts with different people. Having different kinds of issues, budgets, things like that.

And I was just like: this is not really what I like to do. I like to find stuff out and write about it and try to make things happen. So I started casting it around, tried to figure out where I could do that, so I can just do the work that I actually like to do.

VFD: I mean, that's still a big decision. To go: well, I'm just gonna do it all myself. And hope it works out.

Did you set rules in front of you? Did you do the classic thing of: OK, I'll give myself six months. And then if it doesn't work out, I'll come back.

Judd Legum: Yeah, I mean it was a little scarier then, because it wasn't like anyone was doing a political newsletter. So I had no idea. And honestly, I had started thinking about it for a while.

But really, there was a period of six weeks from when I first thought about it, and started thinking that no one really pays for a political newsletter, because there are already good free ones. Like, there were some people making money, but they were doing stuff that you could write off as a business expense. So I kind of talked myself out of it at first.

But yeah, eventually, I kind of talked myself back into it. And I told myself that I would give myself a year

VFD: Right OK,

Judd Legum: And then in a year there was other stuff kicking around as possibilities. And I could probably just go do one of those if it didn't work. So that was my initial plan – I was going to do this full bore for a year.

VFD: OK. And if I may assume - I assume people did end up paying for it. Why do you think they did?

Judd Legum: I think, over time, I figured out how to play to my strengths and find things that people were interested in. Initially, I had this whole thing of what I thought was going to be a newsletter. One of the things I thought was pretty much what you're doing with this newsletter. Like, I thought: oh, you should do long form Q&As. But I found I'm not really that very good at them.

I did a few of them and people were like… there was no response. Like… at all. But once I kind of sorted through that, and really got down to my strengths, which is drawing on my research background and a political sensibility about where the country is and where the lines are, then I kind of found different niches where the work can have some impact. And then that's, I think, what people really respond to.

So that's good. Like, I'm happy. I'm happy that I found this place. Because I sort of feel like finally I'm in the place where everything is kind of synced up a little bit.

VFD: Did the political climate in the US inspire you in any way? Given, I mean, I think the last four years, at least in my life, are the most chaotic I've seen. Did that give you any sort of motivation to be like: I can make something that is making a difference or point things out in a way that others aren't?

Judd Legum: Yeah, but I think it's less about that. I mean, I think definitely, without a doubt, the Trump presidency was by far the most chaotic part that I've lived through. But, y’know, a lot of it, going back to what we were talking about… The Iraq War is my central point. That was what made the blogosphere so essential then. It was really the only place where there was really critical discussion of what was going on in the Iraq War, like it really hadn't reached The New York Times or The Washington Post yet. So I'm always feeling that way.

Well, maybe not always feeling that way. But I'm always looking out for the thing that isn't being talked about that might actually be important. And that's kind of the approach I take to the newsletter. It's like: What's going on? Oh, these people are still giving money to Steve King while he's using white nationalist talking points on a regular basis. Like: that's a big deal. It does matter. So that's kind of my approach.

VFD: So is that the big story right now that no one's talking about? I've seen you writing things about the funding of these, let's say, interesting politicians. Do you think that's the thing that's not getting enough attention right now?

Judd Legum: That's what I've written a lot about this year. But I think it changes, y’know? In the start of the pandemic, like a year ago – and I've written about this pretty recently, too – but I started writing about paid sick leave and how there's no guaranteed paid sick leave in the United States.

And I first started writing about it when the restaurants were still open. So I was like: There's people who are working in restaurants, they can't call in sick, or they won't be able to pay their bills.

So I think there's different stuff that happens and I'm also worried that I get too locked into one thing, and that maybe I need to shift. So I’ve been on this corporate donors thing for a while, and I feel an obligation to stay on it. But then I also start to worry that maybe I'm missing something else.

VFD: What do you think of the state of politics in the US right now, then?

I mean, I visit the US every few years, because I have family there. And I see a lot of issues at the Civic level, and financial divide, and homelessness, and it never seems to get better. And the political side of things seems to just get more chaotic. And that is obviously a very outsider perspective. I'm in Australia. But what do you think of the state of politics in America right now?

Judd Legum: I don't think it's great! I don't think it's great.

I think that there are factions that used to be relegated to the fringes that basically took over the mainstream, and they can still drive, and are still effective at driving, the conversation.

So I don't think that's great. I've never been a cynic, though. I've always kind of believed that I don't think necessarily about the overall state of things and more just where the potential for things to get marginally better is. And I use that to stay motivated. And I do think that change is possible.

Like, even in the 2008 primary, which I was a part of, all of the major candidates opposed same sex marriage. All the major Democratic candidates opposed same sex marriage. And then I saw a report today that 67% of the country of the United States now supports it. And obviously, like, you couldn't even think about running to be the Democratic nominee if you didn't support it.

So we're in the middle of all of these really – some of which are just dumb – but just all these cultural battles, and things like that, but I do think it's possible that things get better.

Yeah, some of the things get better. Some of the things will probably get worse, but, I guess I'm just never… If I was cynical about it, I couldn't keep doing it. It’d be hard to pump out four newsletters a week if I was feeling cynical.

VFD: Yeah. I think I need to work on being less cynical.

Judd Legum: I mean I just don’t have it in me. I think I'm just… I view things very earnestly. Which is probably annoying to a lot of people. But that's just … I think, the way I am wired.

VFD: Sure, OK. So then the next question will probably be interesting. I was gonna say when have you failed, but I think probably a better way to talk about it is: when have you made a big mistake and what do you do when you approach failure or approach not getting something right?

Judd Legum: I mean, I think that I've had so many. As we've talked through my career, it's basically like a string of failures, right?

VFD: It's a pretty good string of failures, I'd say. It's a pretty good string of failures.

Judd Legum: It's been interesting, the failures: I worked on the Hillary campaign and she lost that. I ran my own campaign and lost. I started a website and fairly shortly after I left that website, it was closed down. So, no, I definitely had my share of failures.

Can you say that last question again, though, because I forget where I was when I was getting to that.

VFD: How do you approach failure? How do you, as someone who is not a cynic, keep going and not let it get to you?

So the broader context is – and it's kind of part of the whole project – is I think there are interesting and high profile people on social media, on Twitter, in media, who have big followings or otherwise. And there is a consensus from a lot of people that like: this person is a killer at their job. And they are a machine. And they are just better than me in every way, which is what has led to them being so successful. Which I don't think is very true, but because of social media, it's easy to fall into that trap.

So I guess the reason for the question, and the way I'm trying to unpack it for you is, explain how that's not the case. Unless you are just a whip and you’re like: I'm actually the best!

Judd Legum: I think what motivates me is just the the fear of failing, I would say. But I don't expect it always to work out. So I guess I'm not surprised. I think when I fail, I think my first reaction is sadness. I remember Hillary losing – not so much for her, because I was pretty sure she would be okay.

VFD: Yeah I think she was OK.

Judd Legum: But when I ran myself, like for office, I put everything I had into it. Like, I would just… I totally changed my life. I went there, put everything I had in for it, called every single person I knew, begged them for money. And when I lost and it didn't work out, I just… I mean, I was just really, genuinely, earnestly upset. Crying. Just devastated.

But I think that a lot of times, sometimes that ends up being good, right?

Sometimes you just need to go through those things. Because I think if I would had won, I probably would still be in the Maryland legislature some place, or maybe if things worked out I'd be like… maybe one day I'd be a member of Congress. But I think I kind of found, looking back on it, it kind of led me to a place where I can be more of myself, right?

Part of the problem with that was, I wasn't really able to be myself. I had to pretend like I was the kind of person who would go to neighbourhood meetings and gatherings when really that's the absolute last thing I want to do. I don't want to go, I don't want to talk to anyone there. I want to not be there at all. So, I think after I’m sad I can try to figure out something from that.

VFD: Sure

Judd Legum: So I think that’s how I approach it.

VFD: I think that's a good approach. Every conversation I have with someone I’m making a note in my head like: do that! And there's just so many notes that I have to read, I probably need to sit down and go through it myself.

OK, well, conscious of time. Thank you so far. I know we're kind of going over a bit, so last question then. It's kind of just about the future and what’s on the horizon for you, whether that's the newsletter or any projects you have in mind. Is anything exciting or new about 2021, besides the fact that maybe you'll be able to go to a restaurant and live a somewhat normal life?

Judd Legum: I want to go to Australia is what I want to do. Seems like things are much better there.

VFD: They are, but we don't have the vaccine. I mean, it's here, but it's very slow. And I know I sound like I'm complaining about having, like, too much money or something because we have zero cases.

Judd Legum: I think that's the issue. The countries that are doing well, they're less motivated for the vaccine because they're not living in a hellscape.

I feel like I found that I like writing the newsletter. One of the things that I'm very conscious about is like, extending myself too much. People will say: oh, why don't you start a podcast? People always, over the last three years, probably once a month, somebody says that to me. But I don't think I'd be very good at doing a podcast but also like… it's hard to do a podcast! That takes a lot of time! You have to book guests, you have to figure out what to say, you have to figure out how to make it different.

So for me, my future plans are to really try to make the newsletter better, and just try to build it out. And I think I'm just scratching the surface about what you can accomplish with this model. So that's really my plan. My plan is to kind of just try to invest in it and see what I can make out of it. Yeah.

VDF: OK. Well, cool. Thanks so much again, for talking and taking time out of your night responding to a strange DM from me. I am aware that it's probably pretty weird to get an Australian guy being like: hey, talk to me about your entire life for over an hour.

Judd Legum: Everyone likes talking about themselves.

VFD: That’s the theory.

Judd Legum: You'll always get people who want to like talk about themselves. That's the key they gave you – like when I used to knock on the door and it's like: How do you get someone talking? Ask them about themselves. People love it. And I'm no exception.

VFD: Well, enjoy the rest of your night, and your week, and thanks again.

Judd Legum: Yeah, you too.