Very Fine Day #31: James Hennessy

Brad Esposito

JAMES HENNESSY is a writer, reporter, and the current editor of Business Insider Australia. His newsletter, The Terminal, is a must-read. The dude’s wicked smart. In another life I worked with James, so this interview has a bit of - I don’t know - casualness to it? I enjoyed catching up with him. James studied media and philosophy, and though he acts as if he doesn’t care much about ~ thinking ~ about things, I think he does. And he’s good at it. Follow him on Twitter, where he has a pretty good ratio of hits / misses.

VFD: Are you in the office at all?

James Hennessy: No, no, no, no. I don't do essential work. Nothing about what I do is essential.

VFD: You’re informing the masses!

James Hennessy: OK, maybe,

VFD: Where are you at the moment? You moved, right?

James Hennessy: Yeah I’m in Erskineville. I've been in this place for about a year.

VFD: It's so nice there.

James Hennessy: It's great. I moved out of the last apartment because we did lockdown in it and we were like: this sucks. We should find a fresh place. And then obviously it happened again.

VFD: Are you running Business Insider from your study? From your bedroom?

James Hennessy: Actually, yes. I am. But mostly my desk that I have here. It's the command centre for Business Insider.

VFD: Is that easy?

James Hennessy: I mean there’s nothing that I cant really do from here.

VFD: Right. I guess I was trying to think about where to start here, because it's one of the few times I’ve talked to someone where I have a relationship with them previously. We worked together. I know you ahead of time.

James Hennessy: Yeah I thought that might be the case.

VFD: I was thinking about how far back to go. You grew up in The Shire, right?

James Hennessy: Yeah, I did.

VFD: Tell me about it. Do you think living there might have formed the way that you think about Australia, and living in Australia?

James Hennessy: I think it was pretty formative, actually, in the sense that The Shire is obviously still not diverse compared to the rest of the country but is significantly further along than it was. When I was growing up it was an extremely white, anglo part of Australia. I’m baptised catholic and there weren’t even catholics – that’s how WASPy it was.

But I think it was interesting because I then went to a selective school in The Shire which brought in a lot of people from well beyond the catchment.

VFD: Right

James Hennessy: So it was significantly more diverse than The Shire was. I think that was an illuminating moment and process to get through. You go to primary school – extremely white and protestant Australia – and then High School is significantly more diverse. I don’t remember what the culture shock was like because obviously I was 12-years-old,

VFD: But it wasn’t that big that it broke your brain,

James Hennessy: No, totally. But it was different. You realise how not-so-much “sheltered” you are but what a weird little microcosm you are a part of. And then obviously, now our prime minister Scott Morrison is from The Shire and that has become a big part of not only his constructed identity – constructed in the sense that he’s not from The Shire, he just moved down here or whatever.

VFD: I’m sensing a bit of local animosity: He’s not actually from here!

James Hennessy: Yeah he’s not from there. He’s not. He doesn’t really like the Cronulla Sharks. But the sense that The Shire is now extrapolated to the national scale and gets nationalised because people thing it as formative to how the Prime Minister thinks about himself, and therefore how Australia sort of thinks about itself. It’s kind of interesting. And I know that – because you’re from the Northern Beaches – there’s obviously some similarities there. They’re a little bit different but they both have that insular view of themselves.

VFD: Yeah, totally. Insular, white, and also an undercurrent of – like you said – Christianity and religion that you aren’t aware of until you get invited to an event on a Friday night and realise it’s actually a church group.

James Hennessy: Yeah there’s a bit of that. Obviously the actual bible belt in Sydney is up in the northwest in The Hills, but it has the same undercurrent.

I mean, you go to Cronulla now and it’s a massively different place to when I was growing up. I don’t know if I’d say it’s “hip” but it’s got the vibe that’s a lot more like what you would expect from modern Australia. It has that modern, metropolitan Sydney vibe. Whereas obviously, one of the big moments when I was a kid was the Cronulla Riots.

VFD: Yeah.

Worth checking out the ABC’s retrospective of the Cronulla Riots

James Hennessy: Which is, I think, the first moment where I was like: Oh, there’s something different about this area. There was a slightly more hostile undercurrent. Like the world was looking at it.

And when you’re that age, it’s hard to wrap your mind around the area that you grew up in – like your little mind palace – being the focus of the world. You can’t really contextualise that.

VFD: How old were you when the riots happened?

James Hennessy: I would say I was around 13.

VFD: Right. So did they sit you guys down in school to be like: Hey, this is happening - or has happened…

James Hennessy: I’m pretty sure they did. I can’t really think about it but I do remember the school would sit us down and be like: this is not what we’re about. There’s a few events throughout my life where you get sat down at school like that, and it was the Cronulla riots and 9/11.

VFD: Yeah, obviously different cultural impacts in different parts of the world.

James Hennessy: Yeah totally.

VFD: So do you go back there often? Your family still out there?

James Hennessy: My parents are there, so I am – obviously not at the moment – but generally I go down pretty regularly.

VFD: You hate it?

James Hennessy: I don’t really. Y’know, returning to the suburbs – I can’t really imagine myself living in the suburbs – but it’s nice to visit.

VFD: What was your escape from The Shire, then?

James Hennessy: Ah, going on the computer mate.

VFD: Hahaha,

James Hennessy: Do you mean -

VFD: I was thinking physically but we can do mentally, too. If you saw the computer as a way to get out of The Shire.

James Hennessy: No, I was totally joking. I never felt like: I need to get out of here! I never really had that feeling. I did eventually leave because I went to Sydney University, I left high school, and then after a couple of years at university I moved out of home to the inner west where so many other people do. In fact, it’s a really popular place, specifically for people from The Shire to move.

VFD: Why do you think that is?

James Hennessy: I don’t know. The stereotype with The Shire- and it’s probably pretty similar with the northern beaches – is that if you don’t leave you’re there forever. That’s where you put up sticks. And when you buy a house you don’t really leave the area because you like the lifestyle and the culture. But I think the kind of person who wants to get out for a specific reason, I think it’s normally to go to university and to live in bohemian Sydney.

So many of my classmates from school ended up in the inner west. If they weren’t in The Shire they were in the inner west. And it wasn’t like friends moving to be with friends, it was just a spreading. Well, maybe it was that. But it’s interesting.

VFD: For me, and it’s a very, very, small realisation, but I remember when I moved out of the northern beaches and came into the city I just had this revelation that all of the food I’d been eating that I thought was really great and from all of these different cultures was actually just… shit. Like, the most white version of that food.

James Hennessy: Hahah, yeah.

VFD: So you don’t see yourself as a youth that was online heaps and using it as your escape?

James Hennessy: Well, I was online a lot. I don’t know if I was doing it as an escape. But I was really into computers as a kid. I vividly remember my parents taking me, when I was 5 or 6-years-old, to computer classes. I don’t know if you did that,

VFD: No, not me,

James Hennessy: It was extra-curricular. You’d go and learn computer stuff. This would’ve been early internet research things. I have no idea why they did it.

VFD: The boy likes computers! Let’s get him into computers!

James Hennessy: I think it was that I really enjoyed playing with the family computer and they were like these are the skills of the future so they sent me somewhere for an hour a week to get computer classes. I haven’t thought about that in ages, actually. But I was always really into that.

And I was always really interested in internet culture from an early age.

VFD: Like what?

James Hennessy: Just lurking on forums. Just looking around on these forums about all sorts of stuff – I’m trying to think of specifics. When I was a kid I was really into the Titanic.

VFD: The movie? The event?

James Hennessy: Yeah, like the ship. I was super into the Titanic. I remember I would read a lot of stuff online about the Titanic. It was a weird fascination because I had no interest in ships, otherwise. Today, I couldn’t tell you anything about ships. I haven’t really retained anything about the Titanic either. But I went through a period where I was really fascinated with this particular event.

VFD: Was it the movie that kicked that hobby along?

James Hennessy: I’m pretty sure I saw the movie at the time. This was like 1997-1998. That’s a pretty obvious connection, or at least it had everyone talking about the Titanic so you absorb that through osmosis. I definitely remember hearing about it on the internet and just reading bizarre blogs and shit about people from people who were clearly very interested in the Titanic. And that’s my earliest memory of an internet rabbit hole, right. You’re reading it and you just get this escalating sense that there’s a community there, but also that there are people who are properly obsessed.

VFD: Yeah,

James Hennessy: I was just a kid with a fascination and I wanted to read about it. But you get the sense that there are people where this is their life. And there are people who are super visible now, like that, on any topic. You can find the expert internet mystics obsessed with any topic.

VFD: Yeah, you blew it forgetting about all that.

James Hennessy: Yeah, I blew it. I could’ve been a Titanic guy. I haven’t retained any of that information. But at some points my parents got me a book about it for my birthday or something.

VFD: You just threw it against the wall,

James Hennessy: Yeah like: This is nothing. Let me read some crazy blogs online! But yeah, I was invested on that level. And then within the culture you can find more forums and I did that a fair bit when I was a kid as well, and that moves into the early days of the social web. I would have been early in High School when social media really started to take off. Myspace and stuff.

VFD: You big on Myspace?

James Hennessy: No, I was just present. I never really invested too much time making my profile look shmick or doing HTML stuff.

VFD: What was the point of the computer classes then, man!

James Hennessy: Well, I learned to google facts about, like, rabbits really quick.

VFD: When you went to university – I think I’m getting this right – did you do psychology, or philosophy? Something like that.

James Hennessy: Philosophy was my Arts major, yeah. It was a course at University of Sydney which was Arts and then in brackets “Media and Communications.” So it was basically a media degree but under the umbrella of Arts.

VFD: Why’d you do that?

James Hennessy: Why did I do media? I didn’t really have any aspirations of being a journalist. I think it was like that I really liked to write and that was just my thinking: Oh, I’m going to study something where I can develop that. Or, maybe more cynically: this is the only thing I know how to do. I’m no good at maths, no good at science. I’m going to do something that I’m good at. And hopefully this will turn into something I can actually make a career out of. And luckily I have – I don’t think particularly due to the degree. Look, going to university was good. You meet people and you make connections, and it’s hard to seperate those things. But I don’t think I learned anything from it that has been absolutely vital.

VFD: Yeah: I learned nothing.

James Hennessy: Yeah it was like: well, I’ve got to go to university. It was just that compulsion.

VFD: Do you think the philosophy part of your degree has helped you?

James Hennessy: Yeah I think that was useful in the sense that philosophy, like English literature and a bunch of other humanities subjects, is something that a really great lecturer or teacher could help you understand better but there’s nothing really about university that you need for that. You can just read all of this material and you don’t need to go to university for it.

VFD: Will Hunting over here,

James Hennessy: But at the same time, being in those classes and talking to people points you in the right direction. And that was helpful to introduce me to a whole bunch of ways of thinking that I think was useful.

VFD: Did you have a guy? Or a girl?

James Hennessy: No, I never really had a guy. Not one of those types. I didn’t have a philosophy thing that I really glued onto. Y’know, there’s politics stuff. Reading my Marx. I do love all of that.

But despite majoring in it I’m definitely not one of those guys who’s completely fascinated by Wittgenstein and the phenomenology that dictates our lives. I mostly just thought it was learning stuff that was very useful in framing my thinking and helping me to think a certain way about things logically.

VFD: Did you get work out of uni? Did you do an internship or something?

James Hennessy: Yeah, I did. I did an internship at a social media company and then worked at that company straight out of university.

VFD: Just scheduling posts,

James Hennessy: Yeah, community management. Stuff like that. And it was a startup so I got that insight. It was a relatively successful startup, and it was especially interesting to be around because you get the sense of what it’s like to run that environment. Y’know: the founder is always there. And this was my first job that wasn’t retail, basically, or fast food.

VFD: Yeah

James Hennessy: And it was that really, often shambolic, startup environment. There were so many things about it – which even at the time - I was like: this is fucking stupid that it’s operated this way. And in retrospect, even moreso. But I found that a really helpful learning experience just to be around that. And I moved into digital media after that. I guess almost my entire professional life, post-graduation, has been in that startup world. I don’t think I have ever worked somewhere that doesn’t have a little bit of that energy.

VFD: Yeah, it’s a nice energy.

James Hennessy: I mean it can be – for sure. In a lot of ways it has been really beneficial, but it means that I don’t know what it’s like to work in a really big organisation that’s very structured with systems in place. I’ve had insights into that at various points but I’ve never worked in an environment like that long term.

VFD: So how do you think you became a writer? And a good writer – there’s a compliment in there for you. Because I do think you’re a good writer. It sounds like your didn’t just jump straight into writing stuff.

James Hennessy: I wrote fiction in high school – just dicking around. And I definitely like to write, casually. Like I said, back then I was like: This is the only thing I’m good at, so that’s what I want to study at university.

VFD: What was your genre: sci fi? Fantasy?

James Hennessy: Yeah, I’ve been into sci fi and speculative fiction – sci fi and horror have absolutely been my genres forever.

I wrote a lot in high school, but in terms of what really honed my skill as a writer it was probably starting a blog at the beginning of the last decade, around 2011. It was a politics blog. And a lot of it was done as imitation. You read a lot of bloggers that you think are great – and this was the late-2000s blogging scene – and I read a lot of that. And obviously when you’re a dude who is 20-years-old you’re reading Hunter S Thompson like: this is so sick. Everyone does that.

VFD: And: I can do this too!

James Hennessy: Exactly. And that’s not the worst impulse. I think this is how you get good at writing – doing exactly that. I think everyone does it, to a certain degree. You read the people you like and then you try to write like that. And that can often border on plagiarism on a sentence-by-sentence basis. But a lot of it is flair – you’re trying to imitate flair – but you can’t really do that. You have to develop it. But it teaches you a bit about how that works.

So I wrote a blog back then which, in retrospect, was not particularly great.

VFD: Is it still online?

James Hennessy: No, no, noooo. It’s gone. I obliterated it. It was like: now I’m going to have a professional presence and I’m getting published places and I’d rather just point people towards where I have been published. And it was the death of blogs. Like, no one was actually reading blogs anymore. It’s kind of back now with newsletters, and I was boosting it on Twitter - Australian politics Twitter. I think it really helped me hone the chops of writing stuff, having people read it, and respond to it. But a lot of it was trying to write poison pen takedowns of shitheads.

VFD: John Howard… was it John Howard? No, that’s too far back.

James Hennessy: It wasn’t so much politicians as it was conservative commentators. And people still do this. But I think it’s a really interesting process – which still kind of exists but definitely did back then – which is that doing a great takedown is a shortcut to becoming known.

VFD: Absolutely. If you can do it.

James Hennessy: And I feel like now a lot of that energy gets diverted into doing a takedown of a TV show that everyone likes, or some contrarian thing that everyone else thinks is good. Whereas I think this was more like: I’m gonna write something about Andrew Bolt and I’m going to write the one piece that destroys him. And if I write it in a way that is sufficiently venomous or powerful that’s going to resonate. Because, y’know, people will always engage with and share shit about people they don’t like.

VFD: Yeah

James Hennessy: So it was definitely a significant amount of that. It probably crossed the line into defamation. But in a way I think that was helpful because it teaches you to write in a way that’s emotional and punchy and interesting. At least you like to think so. When you’re writing against something and you’re trying to really express why you don’t like something…

Y’know when you’re reading a really great piece of writing that’s a bit hateful, the rhythm of it is: Yes, yes, yes. You read it like: Fuck yes I also hate this shit. And that’s a skill to be able to write like that. But it was definitely trying to - at the tail end of the blogging era - hack together a blog and write in that internet-y way that I think helped develop my writing skills.

VFD: Did you ever come to any sort of realisation or revelation that, by doing those hit pieces, you were kind of just feeding the beast. Like: you’re never gonna kill Andrew Bolt.

James Hennessy: Yeah, totally. I think that was a big part of why it completely petered out for me. It was exactly what you say. But at the same time I don’t think I ever had the belief that I was doing it – it was just what I found enjoyable writing. I thought that was fun. It’s the state that’s enjoyable to be in when you’re an angry young man.

But I think you’re right. There’s definitely an element of feeding the beast which then gets transposed to Twitter. Like: That’s what people do on Twitter all day. And I think everyone has, to a certain extent, come to that realisation over the past few years. Like: this just sucks. It sucks being this way.

VFD: Well it’s kind of like that, right. Kind of. But sometimes I feel like it’s only media people – or people with a certain logged on-ness. Australian Twitter in particular is a really good microcosm of this because you have – without naming them – but let’s say broadly “teardrop Twitter”.

James Hennessy: Got it.

VFD: But a lot of that is driven by individuals with no profile picture or identity writing long screeds about how Scott Morrison actually has secret Hillsong holiday trips. All this shit.

James Hennessy: That’s true, you are right. And I often try to think about what anger looks like online now, right?

Just before we were talking about how I came up reading in forums – and a lot of people have made this observation – but the old, pre-social internet was in some ways immensely more hateful than the current social internet. Because there were no checks and balances. Yes, it was kind of all cordoned off and everyone had their stack where they lived and conversed, but when I was a teenager I spent an inordinate amount of time on Something Awful, for example, which is often talked about as one of the originators of a lot of internet culture.

VFD: Yeah,

James Hennessy: And I didn’t post very much but I certainly looked. And the social web is kind of defined by the scale of it and that’s what gives it power. Yes, it’s hateful and angry, but it’s the fact that there’s a million people screaming at you rather than 20. But in terms of its character there was something about the old forums that was so much more interesting in a lot of ways but also had so much more to dislike. And it was, well, awful.

VFD: Yeah, certainly awful.

James Hennessy: And there’s no moderating impulse that everybody has now.

VFD: And there was a lot more anonymity, right? Or at least it felt like a lot more anonymity. And because of that you would click “next” on a forum, go to page six, and then there would be a picture of a dead body or something.

James Hennessy: Yeah exactly. And you can find that sort of stuff on Twitter right now but you really have to dig for it. And there’s definitely the sense that if you're anonymous on Twitter, or pseudonymous, it’s kind of the aberration. A lot of people assume the natural mode is to be out there and if you're not doing that, then you're kind of against the grain.

On forums, no one would sign up with their actual name and sit there and post with their face.

VFD: And if they did they were thought of as even more insane.

James Hennessy: Yeah, totally.

VFD: I want to talk about your newsletter because I really enjoy it. And I have been reading it, also. It has probably been a few months since you kicked it back into gear, but you have been publishing it, on-and-off, for 18 months or so.

James Hennessy: Yeah. I mean, I started it back when the first Substack boom happened, which was around 2019. And for the past however many years whenever a new thing comes out like Medium I always write a few things to see if it’s something that actually snowballs and gets a bit of exposure. But every single time I’ll do a few posts and then leave it like: Well, guess I’m not going to be one of the big guys on here.

VFD: It’s been three weeks and I can’t be fucked.

James Hennessy: Exactly, can’t be bothered. But again, it just became one of those things where I was like: I’m just going to write some stuff here, some thoughts I have, that I wouldn’t want to write on Business Insider.

But anyway, when I decided to kick it back into gear I wanted to see if I could build something where I could potentially turn subscriptions on. A little side hustle where I can make some money and get paid to share my thoughts. And there are probably some people who can get away with doing just their thoughts on things and people pay for it. But obviously, when you look at the list of the best performing substacks, there’s always a point to it.

VFD: Right,

James Hennessy: There’s always someone there doing something specific. Writing about climate change, whatever – just some higher concept going on. So I asked myself: what am I actually interested in and what do I want to write about? And that’s when I decided to hone in on things that I am obviously interested in but try to form a coherent thrust behind the newsletter. And I kind of settled on how I like thinking about things esoterically. The weird and unusual in the world of tech, I guess, but also where it intersects with politics and business and philosophy to a certain level. It’s hard to articulate which is probably not great when I’m trying to sell this to people.

VFD: Hahaha,

James Hennessy: But basically, we’re in a really strange place right now in the world. There’s a huge amount of political realignments going on, everything’s in flux: social flux, political flux, what have you. And we have a huge amount of technological and network development which feels like it has been accelerating for the past 20 years, building up to a leap into the unknown. And to the extent to which that’s actually true – or just seems that way – you could probably debate. So there’s these two things happening at once and it’s kind of hard to tell at times what are material political developments and what is caused by technology. And I think this is a really interesting debate.

For example, you have this political battle over radicalization, right? There’s been so much stuff over the past few years, especially since Trump was elected, and certainly after, where it’s people being radicalized online into becoming Nazis or far-right.

And so there are all of these investigations into how YouTube algorithms and Facebook groups cause people to go crazy or right wing or whatever, but on the other side of things we’re also living in a really disjointed time for economic reasons, for social reasons, and for political reasons. And it's sometimes difficult to extricate those things.

VFD: Yeah.

James Hennessy: Like, the YouTube algorithm might turn you into a Nazi. But what put you in a position where you were receptive to that kind of messaging? This is just kind of an example of something that I think about. And that’s kind of what The Terminal is about, to me. It's exploring technological development like fintech and social media and internet culture, and then the politics of the other side, and trying to work out where these things intersect in a way that I hope is thoughtful.

VFD: Being in Australia, how do you find that affects, I guess, creating a media anything? Because personally, I find it does have an impact on my creation, my place in the cycle of the media, where and when I can inject my content into the world. Because we’re all the way on the other side of it, right?

James Hennessy: Yeah, I think it definitely does. On the one hand, Australia is very much plugged into all of this stuff. And Australia is a very online country. There’s the joke that the National Broadband Network is really slow but we have fairly sophisticated infrastructure, we’re early adopters, and we’re always on top of this stuff. So if something happens online it’s generally happening in Australia as well. And when you’re talking about these things in culture we’re at the coalface, in some respect. But also, Australia’s media environment is very small and it can only sustain so many enterprises that are oriented towards Australia.

So this is the weird thing. On the people that are subscribing to The Terminal, its evenly split between Australian and primarily American subscribers, and you kind of get into this weird position where you’re like: should I write about Australian stuff? Because if you’re American why would you care about that? Because it’s just like America only smaller, in a lot of ways. So I’m still trying to figure out: Am I trying to be Australia’s substack guy where a bunch of Australians will subscribe to it and I’ll talk about Australian things and try and build a media product? Or am I going to look to greener pastures like the US and the UK, where between those two countries there’s 400 million people? But again, those are really crowded markets.

It puts you in a weird space between two worlds when you’re trying to do something like that in Australia.

VFD: I don’t think that’s isolated to being an individual creator, either. I think if you are the editor of Business Insider, or you work for any of the media orgs that aren’t News Corp, or even do work for News Corp, it’s not uncommon for people who work in the industry in Australia to feel like: I can’t be different enough. Because there’s actually not space to do that.

James Hennessy: Yeah totally. There’s very little space to do that.

VFD: Alright man, well I wont keep you any longer. But thanks for chatting. Actually, I did want to ask you, have you seen “Nomadland”?

James Hennessy: I have.

VFD: I watched it by myself a week ago - which is probably the best and the worst way to watch it, and I haven’t had anyone to talk to about it. I know I’m very late. Sitting here being like: wow, it’s a good movie! Like: no shit.

James Hennessy: Yeah, it’s good. I’d be interested to hear what you think about this actually. Because I do remember that it got massive critical acclaim and then there was that period where there was a discourse about the Amazon stuff.

VFD: Right, because Amazon let them film in the warehouse.

James Hennessy: Yeah, and some people associated with it, the director I think and then Francis Mcdermott, talked about how great Amazon was. And everyone was saying the movie was this great piece of Amazon propaganda.

But I read that stuff long after I watched the movie. And when I watched it I was kind of horrified by the Amazon stuff in there. Because it’s like this idea of the unstable work economy and her life absolutely fucking sucks. And yes, it does sort of depict that she’s like: Oh, I want to work at Amazon because they pay better. But I still think, taking it in its totality, I did not walk out of it thinking: Oh, Amazon! What a company!

VFD: Yeah, I agree. To be honest, I didn’t even really think about that a whole lot. I recognised it when I saw it and was like: oh, that’s neat, Amazon made this movie. That’s interesting. But I think that if the role of the film is to depict what is probably a a more commonplace way of living, particularly in America, then working in Amazon is also incredibly commonplace, right?

I also felt like the more I thought about the film – and like you said, thinking that her life fucking sucks – the bit that I keep coming back to is that I don’t think she thinks that her life sucks. And then it’s like: well then, does it suck? And then that’s the cycle I get stuck in.

James Hennessy: And honestly that’s kind of what the movie is trying to answer. But you watch the movie and from top to bottom are horrified by that situation. And obviously they find community on the road, and all of the real people are fascinating people, but the situation that makes you drive around the country working for nothing is not good.

VFD: Yeah, it’s not the sign of a society or huge world power that is functioning correctly. Anyway, I don’t know if I’ll keep that in but it felt good to talk about.

James Hennessy: Yeah totally. Thanks for having me.