Very Fine Day #14: Henry Abbott

Brad Esposito

Henry is the founder and editor of TrueHoop, a blog (and now newsletter) that has maintained incredible sway and influence in sports journalism for almost two decades. TrueHoop was one of the first basketball blogs when it launched in 2005, and quickly developed a huge following based on NBA coverage and investigations, winning “Best of the Web” awards before eventually being purchased by ESPN. A lot has happened since then – including a long stint at ESPN NBA – and Henry now runs True Hoop independently again – right here on Substack.

VFD: OK, we’re recording. Where are you right now?

Henry Abbott: I'm in the attic of my house in New Jersey.

VFD: Wait, how long have you been in New Jersey?

Henry Abbott: Since the late ‘90s.

I grew up in Oregon and went to college on the east coast in New York. And then after living in Ecuador and Wisconsin, we moved here and got married in ‘98. I guess I bought this house in ‘99.

VFD: Wait, how long were you in Ecuador?

Henry Abbott: Hahah, yeah, it was so cool. It was around six months.

VFD: Right,

Henry Abbott: But it was literally, like: open the window and there's a toucan. And we had no electricity. We sort of had running water from a spring, and we worked at this cloud forest reserve and took people on tours and made the food and stuff. It was pretty cool.

VFD: Is your partner from Ecuador? Or was this just an idea…

Henry Abbott: No, no… So [my wife] Jessica and I went to NYU together and we lived in Brooklyn. This was like 1994/95. And we both got jobs – I worked at CBS News and she worked at Workman Publishing.

We both worked with people who had been there for 40 years or more. And suddenly, it seemed like we were done with college and now we just had our whole life routine set up. I had a union job, and people really did stay forever. People that I worked with are still absolutely there. The majority of them, even.

And so my sister had a German boyfriend for a while in high school. He was very keen on Ecuador, spent lots of time in Ecuador, and became friends with a lot of Ecuadorians. One of those Ecuadorians went to graduate school near where I grew up… and so this guy convinced my parents to become his home-away-from-home.

So that was Juan Carlos, and he spent a tonne of his Christmases and a lot of summers at my parents house. So he was like part of the family.

Juan Carlos came to visit us in New York and we were like: oh my gosh, we're on this boring career track to become boring people. And then he's like: Y’know, for $1,000 you can live like a king in Ecuador. And it’s like: we have $1,000, right?

And then what really sold it was him being like: you've never had a banana.

He's like: this thing they have in the grocery store in America? It's not a banana. Where bananas are from… bananas tastes vastly different. And there's lots of fruit you've never had: there's a thing called guanabana. And there's a thing called taxo.

And I don't know that much about food, but Jessica really knows a lot about food. And I think she was kind of mind blown by that. Just the idea that (a): she had never tasted a banana, and (b): there were whole fruits that were common that she'd never even heard of. And I guess now you can get those things from a lot of places, but we just saved very little money, maybe like $5,000 or $6,000, and we pretty much that night started getting our affairs in order to quit our jobs and go to Ecuador.

VFD: You were only there for six months, was that because you realised maybe it wasn't sustainable?

Henry Abbott: No, it's so stupid. So the first couple of months we lived in Quito and took Spanish lessons – intensive daily lessons – and lived at this guest house. And that was when our average daily spend was going to put us on a clock. But then we met these dudes and we got a job and we moved out into the cloud forest. And then we got room and board and tips. And frankly, we had nothing to spend it on. There was literally nothing to spend money on. So that was sustainable.

But what really happened was the place where we worked was owned by an Englishman of… questionable stability.

VFD: Yeah, like most hospitality / foreign entities.

Henry Abbott: And it just kind of blew up. The guy who was the manager, who was a good friend and is actually a fairly prominent journalist now in England, he left and it was sort of the end an era. So we took our cue that it was time. There had been a death in the family back here as well, and it sort of seemed like time to get back.

VFD: Still, a good experience to have.

Henry Abbott: Honestly, I think about it all time. And one of the things that still strikes me is that out in the middle of nowhere in Ecuador water is… not so hard to come by, but it's a lot of work. You have to get it from a spring to where you're going to wash the dishes and washing clothes is a giant chore.

And people will talk about: Oh, for you guys in America, how's the water situation? And I said to this woman, I remember being like: we shower in water you can drink. And for like a month it was a joke between us where she just couldn't believe I was telling the truth. She was just like: why would you shower in that water? I honestly thought that the last time I took shower. It’s so crazy. I'm like: you can drink this water that I’m showering with. You don't have to have water that clean to shower.

VFD: You don't even think about it, yeah.

Did you say you went to NYU?

Henry Abbott: I did. Yeah.

VFD: What did you do there?

Henry Abbott: I did journalism. But I didn't really have a lot of conviction about what I wanted to study. You're supposed to declare your major in the second semester of sophomore year - that’s the latest you can declare it. And I did that semester abroad in India, Nepal, and Tibet, and I was unreachable. This is before email. And so I came back and NYU was like: “hey you didn’t declare a major!

And I got them to give me four hours. That's all I could get. And so during the four hours I called one of my best friends from high school and he was like: well, you did this internship in journalism. You seem to have some connections in journalism. Why don't you just do that? And it was such a stupid reason to do it. But I have literally never questioned it. Like, I’ve been doing it since ‘93 and I'm still like: Yep! That's a good programme. Let’s do that.

VFD: Well it seems to have worked out alright.

Henry Abbott: Yeah,

VFD: So then out of college did you go straight into media?

Henry Abbott: Yeah, Yeah, I did. I was the news director of WNYU, the radio station.

VFD: Oh, wow. “News Director”.

Henry Abbott: Oh, no, actually, in fairness, I was the Co-news director. Shout out to Katie Chen. But that led directly to a little bit of a pipeline from that job to CBS News. One of my key professors in broadcast journalism had been a CBS News bigwig, and it was all radio people. And the news director who trained me when I was first working at WNYU, she had started working at CBS News. So I somehow got connected to them even before I graduated, and I was training and working some shifts even before graduation.

And then I was delightfully bullied. Like: it's very intense shift work. And it's a big corporation. And you don't really do meaningful work when you're a desk assistant at CBS News. So I had decided that I would decline the offer of a full time job, and then the executive I was in touch with - I had a moment to call her at a point in time - and in my head I was going to tell her: No, thank you. And she just bullied me. She literally started the call and was like: I want to talk about commitment! And just because I couldn't muster the self defence or whatever to say “No” I just took the job.

VFD: You should thank her, I guess.

Henry Abbott: Oh totally. Yeah, she's great.

VFD: So how long did it take you to get to sport as a beat?

Henry Abbott: Yeah, I didn't think it was possible. I didn't think it was a real job.

NYU journalism is a pretty small department and you're there long hours. You're in the building, you’re putting on a TV show, you're there for nine hours with, like, 20 people. So you know everybody pretty well. And the broadcasts are on there and there was just a handful of professors who were really there full time. But there was this guy Mike, who was like: Yeah, I want to be in sports journalism. And I remember the whole time thinking: I don't think that's possible.

It just seems too easy a job. It just seems like too much fun. Not, like… work. And I loved sports, but I just didn't think it could be a job. I don't know why I thought that. I had a mental block. And so I worked in “real news”.

Even when I got to CBS there was a sports guy, right? Tommy Tighe worked down the hall. And I still didn’t think I could ever do what he did, even if it was available to me.

And then the high school I went to in Oregon had a little alumni get-together in New York, which is a very niche affair, because it's very far from the high school. So I went and there's like five people there and one of them was a woman that I had known in high school who was now the managing editor of Slam Magazine. And I was so excited. I first had recognised her name from the message and was like: are you the same Anna Gebbie who’s the managing editor of Slam Magazine??? And she was so excited that I knew her work. So then a few months later… Actually, this is a great moment in NBA history. Do you know the story of the NBA airbrushing Alan Iverson’s tattoos?

VFD: Nope,

Henry Abbott: OK so this is a big moment of NBA media history: The NBA had two official magazines: “Hoop” and “Inside Stuff”. And they did a photoshoot with Allen Iverson when he was a young, rising star and they put them on the cover of one of those magazines and he suddenly didn't have tattoos.

VFD: Is this the ‘90s?

Henry Abbott: Yeah, the ‘90s. It’s totally ridiculous to think about now.

VFD: It's a very ‘90s kind of thing to happen.

Henry Abbott: Oh, my goodness. Just amazing. So that led to some furore. And Allen wasn't the kind of guy to just smile and nod, to his credit. And so they needed to make drastic changes in the administration of these magazines.

“That’s not right. Hey, I am who I am… Who are they to remake me?” - Allen Iverson (2000).

Henry Abbott: So at that time Slam Magazine had the most credibility with players of any publication in the world. So they just imported the management of Slam, Tony Gervino and Anna Gebbie and Scoop Jackson, to run the NBA’s magazines. Which was a pretty cool thing to do, I guess.

And so then Anna calls me and they had learned that they couldn't bring their freelancers with them for legal reasons. So the reason I got into basketball was Anna called me and said: Look, I just left this meeting where we learned that all of the work that we have in process for our first issue… we can't use those freelancers because we could be in some legal exposure for it.

So I'm wondering if you would do me a favour of just doing one interview – a Q&A for basketball. I know you're a serious journalist, and I know you don't want to work in sports, but I'll give you $100 to go and interview Jayson Williams of the Nets. And we'll give you the questions. You just drive over there and ask them questions.

VFD: Yeah, wow.

Henry Abbott: And it turns out I've never done a better interview. Like: he is an absolute wizard. One of the questions was – this is how long ago it was – “Do you use email?”

And he said: Every time I'm in the hot tub, I have my staff print them all out and bring them to me!

VFD: Hell yeah. I want to live that way now.

Henry Abbott: Totally, totally. Oh, he's way ahead of his time. And I just thought it was so fun. I was like: this is so much better than the other crap I'm doing.

Let's say that was November, maybe, when I was interviewing Jayson Williams at the Nets practice facility. And then by February, I was at the All Star game for that magazine with so many assignments that a couple of times I had to use a fake name because otherwise my byline would be too many times in the magazine.

I just started writing so many feature stories for them. I was still a freelancer, but I'm guessing half my income probably was, well, just writing for basketball magazines.

VFD: So were you big on basketball before that? Or was it kind of like a passion that grew into you?

Henry Abbott: No, I really was born of it. I got a Walkman when Walkman were new things. I want to say I was in middle school, so 6th grade or 7th grade, and I went to this pretty intense private school. We had tonnes of homework and the Walkman was like a loophole. It was a way that I could look like I was doing my homework when I was really doing something fun.

And the Blazers, via radio, are really how I became an NBA fan. There would be some nights where I'd be so excited about the game and then the game would end and it'd be 10:15PM and I'd be like: holy shit, I haven't done my homework!

But it was a personal thing. I had friends who were a little into the Blazers in middle school and stuff, but they didn't really become good until almost the end of high school. So the day I graduated high school The Blazers were in the finals, and people were sneaking earpieces into their cap and gown because they wanted to follow the game. It became a big thing. But yeah, mostly my friends were like: we all like these things. And Henry likes basketball.

VFD: So you must have been pinching yourself when you went over into magazines. That's nuts. Like that alone… I feel like your career could’ve ended there. You’re obsessed with a sport and you write for the actual brand of sport. I can only think of the equivalent for me, it's like the EPL, like Premier League football or something.

So then how do you think sports journalism is different to, I guess what we were saying is “real news” before?

From my perspective, when I look at it, all I can think is it seems so much more about contacts, and who you know, and also, it seems a lot more about being a very good writer.

I think you can get by being a poorer writer doing other forms of journalism, but sports journalism and sports writing, if you can nail it, like… it's fucking good. It's really good, right?

Henry Abbott: Yeah. It has a lot of funny aspects to it. It doesn't behave like most media I don't think. One of the funny things about it is it’s like, say, Hollywood journalism. Most of the audience just wants to hear everything's fantastic.

So let’s say, if Tom Hanks were kind of a jerk, that's not getting published anywhere.

OK, if he's a totally scandalous jerk, alright, maybe that's a book and a movie, whatever. But if it's just like: no he's not really quite perfect then you're not getting anywhere with that. Because the audience doesn't want it. I think sports works a little bit like that, where the primary market for Damian Lillard stories is in Portland, and in Portland, they think he's a god. So good luck. You got some choices to make there. Like: are you gonna say he's a god? Are you gonna do anything? It's not really trafficking in truth as a base level.

But most of what I think about, when I think about that stuff – and I think you're making a really good point – is that I'm born of this incredible journey I went on once my work became digital. It will surprise you, maybe, to learn that almost nobody in my industry really got story-by-story feedback on what succeeded.

Even on Sports Centre. They don’t know which segment of Sports Centre is the most popular. I mean, they can find it out. But it's not routinely – at least when I worked at ESPN – it wasn't routinely part of the mix of what they learned, right?

So if this five minute segment at the top of the hour was really, really, good or not… it's just a matter of anecdote. And I've been in so many media meetings where people are like: oh, that's a classic! Or: that one killed! And it's like: well, why do we think that? And really it’s because we’re all in this meeting and we decided it was a fuckin’ classic, right?

And True Hoop became full-time digital in 2005 and I would get traffic for every post, inbound links to every post, social media responses, emails to every post, mainstream media response to every post, and there was just a big bundle of feedback that I never wanted… but it sent these very confusing messages. Like, when I was checking the boxes of what would have made it into a magazine…. Topic was fine, but occasionally, there'll be some really weird stuff.

The one that really got my attention was I wrote a post about how NBA players love The Cheesecake Factory.

VFD: Who doesn't.

Henry Abbott: I mean, everybody likes The Cheesecake Factory, right?

“Nowadays, if ever someone tells me that they bumped into an NBA player out in public, I like to stop them mid-sentence and guess: "Was it at the Cheesecake Factory?" It can make you look like a freaking genius, because once in a while, you'll be right.” - The Cheesecake Factory Did Not Pay Me To Write This (2008).

Henry Abbott: It just became a bit of a phenomenon, right? And in my head the best thing you could do is have a Q&A with Michael Jordan. But in fact, I think that a more popular thing is – and we all know this now from Instagram – but that story on NBA players on the Cheesecake Factory is way better. It's not serious journalism, but it's definitely akin to humans, right? Like, this is the kind of thing people care about.

So I spent literally a decade with things pinned to the wall. Like: what are the qualities of the things that over-performed? And then eventually I got the big jobs revising all the NBA coverage of digital and print for ESPN NBA and could see tonnes of data.

And I do think a lot of the assumptions underlying sports media are totally wrong. The core one is that almost every sports media executive believes that the core of their audience is people who follow a team. And so that's why beat writing is the core of sports media. But it sucks. Like, it's a terrible business. Very few people follow teams in the NBA - I think the NFL is different. I think EPL is probably different. But in the NBA, a regular Dallas Mavericks story has as little audience as anything you can put on You can publish a random fact about a rock and it would get that much audience. So meanwhile, some stories – what you're getting at is these absolutely beautiful award winning type stories – not all of them, but some of them would get 1000 times the audience of your Maverick story.

VFD: Yeah.

Henry Abbott: And because I printed them all out and I put them on the wall, and I read them many times, I'd spent years messing with it. And then I built a team to test it.

But the qualities that work… It doesn't matter who the author is, it doesn't matter as much as you think who the subject is, it matters that it has narrative qualities whereby somebody who reads paragraph one must get to paragraph two, and you can't break that chain all the way to the end. But if you have an incredible storyteller like that, and you set it in sports, it is pretty magic. I think that setting it in sports gives you people who will initially sample it and spread the word about it. That has sort of become my life obsession over the last 5-10 years: what are those stories? How do you tell those stories?

VFD: What triggered in your mind the - I mean, it's not quite a data approach to writing – but you said you had that influx of information and you went digital and you didn't, at first, know what to do with it. I imagine a lot of people would have just – well, a lot of people did just continue to ignore that for as long as they could.

Henry Abbott: Yeah, yeah.

VFD: Because it’s like: I’m happy doing what I'm doing. I'm quite happy believing in what I’m doing and just telling myself it works. And I bet that's some of why the media industry collapsed.

Henry Abbott: Yeah, yeah, I agree.

VFD: But what made you realise: No, this is serious. I should think deeper about these things.

Henry Abbott: Well, think about it: True Hoop was on starting in 2007. So I'm publishing basically anything I want, any time of day or night, around the clock, on one of the busiest websites in the history of the world. And I don't have to look it up. I just get feedback that 95% of it is a total flop.

I would just feel like I have the stage at Madison Square Garden and I go out there and everyone just leaves for the exits. Night, after night, after night, after night. And not always – sometimes they love this one song. Or they love this one thing. So at some point, you have to be really fucking dumb to not be like: what did it take for them to stay for more songs?

Like, I don't pretend that it was immediate for me to have this epiphany but I definitely was like: I better get to the bottom of this. I just had this huge advantage in data, right? Everybody with a Substack or a blog has this kind of data now. I had it starting in 2005. And so I think by 2009 or something I was a little bit like: OK, let's try to figure this out.

I do remember when the NBA lockout came in 2010 / 11 we had a legal shut down, and there weren't stories to write. I remember Brian Windhorst called and he was kind of like: what should we do with all this time? And I was like: I think we need to study this storytelling thing, right? I think we need to actually get good at the narrative structure of a good story. Find out who were the characters that we need to follow. This kind of stuff.

And it's everything that matters now. And I was just beginning to learn it then and I was the exact wrong kind of journalist to apply the lessons I was learning. I was like: let me give you professorial lectures on things that are niche concerns. Whereas the fact is, you want big, expensive, narratives about love and death and sex, right?

I didn't really know that stuff. I had to learn that, and I'm still not particularly good at it. But I think I'm better at it as an editor than as a writer. But yeah, that's sort of how it came about.

VFD: And what did you launch True Hoop on? Does it exist still?

Henry Abbott: Yeah, so True Hoop had many iterations. It was a blog in 2005. On ESPN in 2007. And then it became True Hoop TV, a blog network, it had a podcast. Other things I'm forgetting at ESPN. And then, in 2019, they gave me back the intellectual property. And so we launched it on Substack.

So I first talked to Substack before it existed. Like, they hadn't launched it yet when we had a little meeting about: oh, well, we're gonna cobble together the tools independent publishers need and maybe we would try it. And we were like: Oh, no, thank you. Of course later we were like: Oh, yes, please!

So now we have grand ambitions in storytelling, outside of email newsletters, but we have not launched those grand ambitions to date.

VFD: In 2005, this is pre what you’d consider the social internet, so what was the distribution like? Was it just traditional advertising, and hoping that people came to your site, and emails?

Henry Abbott: No, so blog software has this crazy Google advantage which is that inbound links are the biggest determinant of Google PageRank. And blogs were just machines of inbound links.

I honestly think the day I launched True Hoop it was the 11th blog about the NBA in the world. And we mostly were friends. It was a small enough list that we will sometimes meet for drinks, right? “The NBA bloggers”. You won't get everybody but you get half. And this is before Deadspin, so we all read each other and we all linked to each other. And so in the world of: if you're googling Latrell Sprewell in 2005, the True Hoop posts about him would probably have a higher ranking than an page about it, because we were part of this link sharing mafia.

It was totally organic, but the other thing we did, and I think this might have mattered very early, was this thing they called The Carnival. Have you heard about this?

VFD: No.

Henry Abbott: I think it should come back, to be honest. So the idea was: let's say you're an avid Chicago Bulls fan. And one of the first few blogs in the world is a Bulls blog. You might have no way to discover True Hoop, or a good Warriors blog, or any other blogs.

I don't remember how it started – I suspect I was not part of it but I may have been – but in different corners of the blogosphere they would rotate what they call The Carnival: one person would host each week, and they would write a roundup of all the best stuff from all the NBA blogs. And I would publish it on my blog, and then I think everybody else would publish it, too. And then that way we’d cross-pollinate our audiences. And it was actually really fun. Like, you wanted to read The Carnival. It was a pretty cool thing.

And it outlasts its usefulness once there are 150 blogs around. But when there were 10, or 12, or 15, or 20, I think it was a pretty cool way to get from 500 readers to 1000.

VFD: How many parallels do you see between what you went through with blogs and what is currently happening with Substack and newsletters? I guess I should preface that by saying that I feel like even using the word “newsletter” for what it is makes it seem so dated. And it’s not what this moment is. But I mean, that’s the easiest way to describe it.

Henry Abbott: So I guess there's the famous saying about 100 monkeys with 100 typewriters or whatever, right?

VFD: Yeah. Yeah,

Henry Abbott: Like, both are that in a way.

Everyone can publish, which comes with a very familiar set of challenges. It means some people are going to publish crazy things. Like, bad people are going to publish things, right? With all of these things either there are gatekeepers, or there are not gatekeepers, and if there aren't, then that's going to be very problematic. And if there are, that's gonna be very problematic. That's just how life is. If you hand out microphones to everybody, people will say bad things into microphones. So it feels very familiar in that regard.

Categorising people as bloggers or Substackers is too sloppy. There's just gonna be a wide array of people doing all of those things. And some of them are totally careful geniuses, and some of them are totally sloppy idiots. That part feels exactly the same.

There's a big difference, I think, in the early era of blogs, where there was a period of everything moving online. And it had this Google effect - it was like a discovery mechanism. So everybody's audience shot up. Even your grandmother's blog would have tripled in audience in 2005 because audience was just growing. And it's different now.

It's a more mature market, people are doing more mature things to reach this key audience for all media. Back then it was like, ESPN TV didn't care about web traffic. They weren’t competing for it. Now, every TV show has a rich social presence because we're all competing for people on their phones. So that's different.

And then this being an email product, it doesn't really have a way for people to trip across it. There's very little discovery. So that'll be the challenge of this industry, and it’s probably true of all paywall stuff, but particularly email stuff.

Like, we get the data and I can see sometimes I'll publish something that's very successful to our subscribers. They're clicking the links, they're opening it, they're forwarding it. And nobody outside of our subscribers has any idea it happened. That's a missed opportunity.

VFD: I have the exact same thing going on in my head. I've been thinking about that a lot the last month or so. It's weird, because you want to avoid the obvious solution, which is you build a website and then you port your audience over in some way. But that seems simple. And it also seems like you're you're just doing the old thing. Like: look at me I built or whatever.

Henry Abbott: Like: “No way you have a website. That's cool!”

VFD: So did you sell True Hoop to ESPN? Because you went and worked there as well. Like, it wasn't like you just sold the brand.

Henry Abbott: Yeah, it was a stressful year. But basically, they were interested in True Hoop. And I had a buddy, a partner, who had – it wasn't like a shocking amount of money – but it basically covered my living expenses while we were getting it going. And so he owned it too. And so there was a confusing year of: are we gonna be able to figure this out? And Disney, and corporate lawyers, and conference calls. And all this sounds like I'm walking away with a helicopter, but it really wasn't. It was just, y’know, I was learning the phrase “theory of valuation”…

I got to be involved with lawyers a lot. But the upshot of it was they wrote a cheque to my buddy and I got a job. And they purchased the name True Hoop. And then I worked there for 10 years.

VFD: And in that role were you always related to True Hoop? Or did you float around ESPN and the NBA?

Henry Abbott: Yeah, there was a bit of floating.

So I started out as a full time blogger publishing on, building a network of other bloggers. So that's when we hired Kevin Arnovitz who was my partner in crime in recruiting other people to be affiliated. So they were not on staff, they owned their work, but we would drive them traffic… That was a lot of work and involved a lot of cool people.

I mean, lots of people you know are from that. People who work for NBA teams now, or Zach Lowe, or other people, are from the True Hoop network.

So that was like, 2007. And then I think it was 2014 when I went to a fancy lunch in Manhattan and they were like: we're gonna make some changes. We'd like you to consider taking over this department, which is 60 people. And it wasn't something I'd ever thought about doing. I don't know how I feel about it. I sort of felt like I had to take the job, or else I would be in jeopardy in a different way. It was clear that the future wouldn't be like the past. And I wasn't sure where to be, but I got the weekend to sort of think about it, and ended up making a YOLO-type decision and just going for it. And it was a giant amount of learning for me.

I think I had something like a dozen weekly fixed meetings. So just to start my week there's that many hours filled, and then questions like: can we in four months deliver 1.5 million video viewers on content with the subject of “Team”? If so, there is millions of dollars that we will have – but we have to commit right now. Like, can we do that?

You really think about it, like: that's how the business runs. There is so much stuff. And year one I was kind of just running and just answering questions that I had not well considered. And even just the day-to-day, it was ridiculous. I remember by the NBA Finals, the alarm goes off because I have to be prepping for some meeting. I'm getting up at 6am. But I was up at 2:30am, finishing the day before with all the content that performed.

And there are tonnes of ways that I was new at this high-level management thing. However, all that said, after settling in a bit I built this team with four editors and eight writers: the True Hoop Presents team, which was like Jackie Macmullan, Baxter Holmes, Pablo Torre, Kevin Arnovitz, Tom Haberstroh. And we were just dedicated to the stories that I think had an irrational likelihood of big audience, these kind of beautifully told, award-winning type stories. And that was like… we fucking slaughtered it.

Every single writer on the team had by far the biggest audience of their lives. Everybody had at least a million readers on a story, which like… a lot of famous writers have never had a million readers and all of them did. And we did it as a group. We published twice as many stories as the year before.

So my main job was like: being a general in the military with the army and you have to move resources around. Whereas this was like the Special Forces part of the job where it's like: 12 people, and it's hard to get into that meeting. It's hard to get on that team. But once you're there, you are prepared to handle all kinds of challenges and move fast. And that kind of management, turns out I love more than anything else. That’s my favourite. I’m addicted to that.

VFD: That's really cool. I mean, that kind of makes sense, because that's probably not dissimilar to what you do now, right?

Henry Abbott: Yeah, so I have proposals and have spent a lot of time with fundraising where it’s like: let's rebuild that a little bit more.

I think there's a little bit of an advantage to doing audio, too. The disadvantages – in the pandemic nobody's in their car. And there's too many podcasts, and there are problems with that.

But the advantages are that it forces you into the storytelling structure that would then apply with a number of characters, and three act structure. I think that gives it a chance to become a movie.

So if you took all of the stories that we got huge audiences with at ESPN, and gave them to a movie producer, half of them they would just throw away right away, because they just don't have a lead character in the right way. Or they don't have character development or emotional shift - these kinds of things. But I think if you look at produced storytelling, This American Life-style audio, then they almost always have the right ingredients because it works the same way. Or similarly with audience. So this is my scheme, like what I’d like to do for 2021. I have a weird and promising bunch of things happening in that area, but really nothing to report today.

VFD: Yeah yeah, alright alright alright… I get it. You can’t say.

VFD: So when you left ESPN, how long did it take for you to start up and to regroup again? And what did you do between then?

Henry Abbott: Oh, it's such a crackers period of my life. I was still under contract. It was such a strange thing. It's pretty boring but a group of us were let go with 100% pay and benefits.

VFD: Sounds about right for a large media company stuff up. Was that deliberate? Or were they like: Oh, we forgot to check a box. And now you guys are free.

Henry Abbott: So the bigger company definitely wanted to cut salaries and make changes. And a lot of people who were let go that same day weren’t paid. In this little corner, where we were making money and things did generally work, it was a different political thing that happened. I have a pretty good idea of what happened, but it wasn't about saving money. They actually spent more money.

VFD: Again, classic media.

Henry Abbott: Yeah, yeah. It’s a long and sordid story. But I feel pristine. Like, I did nothing wrong, nor did anyone who was let go at that time. It was just a little, like… some career stuff happened and blah, blah, blah. Somebody will probably write a magazine story about it one day. But it’s kind of swept up in this thing.

I had a little hint it might be coming and I talked to my attorney and was like: if I get this call do I have some sort of offer? Like, do I accept it or not? And he said, basically, if they offer you 80 percent or more of your contractual salary, just take it. If it was less than that, call me and we'll figure it out.

VFD: Yeah.

Henry Abbott: And so I did get that call. It happened to me in a car. And a very high boss with an HR person on the phone calls and I pull over and we have this…Honestly, I know the guy pretty well. And we sort of pledged to be nice about it. And I meant it. But then I was waiting to get to the part where they're gonna offer me something. And they're like: oh, we're gonna offer you 100%. And I was like… that's weird.

VFD: Like: You know I’d still just keep doing this for the same cost, right?

Henry Abbott: Yeah it’s like: was I so terrible to have around the office? Is that the problem? Do I talk too much in meetings? It could be that.

So then I had – to start getting to your question – I forget exactly how long you have but it was something like 20 months where if I got another job I would lose my ESPN salary and benefits. So it didn't make a lot of sense to get another job. And then they also said that they would give me back the True Hoop name at the end of it all, but it wasn't in writing. But I wanted the name back. So I was particularly interested in seeing out this period of time in a very calm way.

VFD: I mean, it's not the worst thing in the world, I guess.

Henry Abbott: I kind of loved it. So then basically I was like: I'm writing a book. I just did a tonne of research and, well…I didn't write a book,

VFD: Well, writing a book is hard.

Henry Abbott: I mean I basically did write a book right here at this desk. I had 20 months. I'm a hard worker, I got up early. I did all this stuff. I interviewed people, I travelled. But I then pitched a book that was 70% written and the offers that I got to publish it were like: Oh, yeah, we would love it if you would make every chapter like this chapter or like this whole other definition of the book. And by then my time was wrapping up and I didn't really have time to rewrite the whole book.

So a lot of it I have done nothing with, and some of it should be thrown away. Some of it I fold into what's going on with the newsletter. Some of it, I'm just kind of keeping for another day. So I did it. But it’s just the book part of it that seemed like I had an opportunity to work for 2000 more hours on it for $20, and I just didn't do it. Didn't seem like a great idea.

VFD: Yeah, I think that’s smart.

OK, last question. Because we're getting deep into time now. And this is a question that everyone gets asked and it's about failure. And it's about how you approach failure, or about how you approach making mistakes. And I mean, you don't have to go into deep personal details. You can if you want. But I think it's important. It's an important question, I think, because everyone needs to know how everyone else deals with shit periods of time.

Henry Abbott: It is a shit period of time, just to be clear. That time is now! Pandemics are terrible.

But yeah… I'm not good at raising money. And I kind of have to. And so I'm like every 19-year-old who's trying to cosy up to a venture capitalist over Zoom, right? Like, I'm that, only I'm less appealing. And, y’know, more know-it-all, right? It's really bad. It’s media, too, and people don't really want to invest in media other than a few exceptions.

So I've had to have these moments of shit where it’s like… I have had a career where really, I've just been incredibly lucky. And if I've had a bad meeting or a failed project, there was a bigger victory tomorrow, right? I have just had people clap me on the back and be like: great job! I just had so much of that. I've been blessed with that. And so I'm a little bit of a baby when it comes to this last year, which has been alarmingly not like the rest of my career.

VFD: Oh really? Why’s that? No… let's not even talk about the pandemic.

Henry Abbott: But I mean, it has just been hard for everybody. And that's what we've done very well. I’m very proud of what we've done. But there are some things left for me to solve. And honestly, it's such a boring metaphor, but the way that I genuinely think about it is like: I'm a runner, and I've run several marathons and it feels to me like that.

I don't like to know how many miles I am into a marathon until we're getting close to the end, because I can't really intellectualise or visualise that distance. It's too stressful. It's too heavy. When you're 23 miles from the finish line… just run.

Like, you just don't have enough miles to count yet. Just do something else in your head for an hour, then check in again. And I feel with this kind of thing it's very grindy. You just need to get to the next phase.

There's not really a magic teleportation device, right? It's more just like we kind of need to inch up. Get things a little better, get vaccines in arms, get case loads down, get travel back, get all of these sort of habits back. Then let's assess where we are. This is how I've been thinking about failure: Is it failure, or is it just like a really rough patch that everyone has to get through at some point? So I tell myself that. It has inconsistent results in lifting my mood, to be honest. But that's what I'm doing and I feel pretty gritty. I feel pretty tough. I mean, I would like to do this again, and you can ask me that in a year, hopefully.

VFD: For sure. Alright, well, thanks so much. I really appreciate it.