How Long Gone podcast hosts discuss the art of conversation

Dubbed a “bro-cast” and the “podcast all your cool friends are listening to”, How Long Gone revives the lost art of conversation.

How Long Gone Podcast Hosts Chris Black and Jason Stewart. Picture: WISH/James Cant

Recently, the comedian Robby Hoffman came onto How Long Gone, the podcast hosted by long-time friends Chris Black, 40, and Jason Stewart, 41, and told a story that perfectly captured the MO of an outlet that has been described by others as a “bro-cast”, “an arbiter of non-toxic masculinity” and the “podcast all your cool friends are listening to”.

“She told us a half-hour story about her having to take a train from Portland to LA because of the storm and all of the things that happened on the train, who she met and why she had to get home,” says Black. “And it turned into basically the story for her life in a way. And that’s the perfect How Long Gone moment,” says Black.

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“[The podcast] creates a new space for things like that to happen,” adds Stewart, of whom the first thing you’ll notice, even when he’s sitting down for a Zoom call, is that he’s really tall (6 foot 9, and he once had an interview show called Tall Tales).

Started as an early pandemic “experiment” in March 2020, the podcast now cranks out three episodes per week, to an audience of more than 500,000 downloads per month. The sheer pace of the output means they don’t get to overthink it, says Black.

“We’re in a prison of our design. [The pace] is the bar we’ve set for ourselves. I think there is a momentum aspect to it for sure,” he says.

The audience includes the expected cool and cool-adjacent men in their 30s, but they also get the mums (“our favourite demo”, says Stewart). Black says the podcast has a 40 per cent female audience. Guests have included everyone from New Yorker staffer Naomi Fry to actress, writer and director Lena Dunham, singer Phoebe Bridgers and actor Lee Pace. No topic is off the table, including Black’s own sobriety, but also, and crucially, no topic is too inconsequential.

Mostly, being “down to clown”, says Black, is the prerequisite for the guests they get onto the show. “Are you happy to have a conversation where you don’t know where it’s going to go? We’re not going to ask you about what you’re promoting unless you really want to, and it’s going be something you probably haven’t done in this format … if you’re just down to have fun and enjoy the conversation the way we are, then it’ll work. And if you happen to be famous, that’s great too!”

The pair parlayed the voracious pace of the podcast into live tours – they hosted a show at luxury retailer Matches Fashion’s 5 Carlos Place boutique in London in January and have more US gigs planned for later in the year. The podcast’s range of merchandise has included canned cold-brew coffee and sweatshirts, and it generally sells out. The duo discovered they had a sizeable Australian fan base when people slid into their DMs on Instagram to ask that they start shipping to Down under. Earlier this year Black and Stewart signed with the CAA agency to represent them across the podcast, as well as an expansion into books, film and TV.

Hosts Jason Stewart and Chris Black.

At the centre of the podcast is the pair’s easy rapport, their willingness to make fun of each other, to offer a piping hot “medium take”, and their natural curiosity about people. They’ve been friends for years, having met when Stewart was a DJ and later a producer for other people’s podcasts and Black was a consultant for fashion brands such as Thom Browne. More recently, Black has consulted on the relaunch of menswear at JCrew.

Their friendship is something they take seriously, and not only because it’s partly why people listen to the podcast. Strangers will come up to them in the street, or recently for Stewart, the gym locker room (“first time at the gym, first time while I was nude”) to tell them they’re a fan.

“I think there’s definitely a generational shift, where it’s like, why would I talk to someone when I have my phone and my computer and my TV and my iPad?”

Black says that part of the reason they work well together as friends and business partners is that they put the friendship first, and also they’ve had enough life experience to speak up when they don’t agree on things. Which, both suggest, is on most things and almost all of the time, but except when it matters.

“I think that a show like this, birthed from friendship, that’s what people respond to, and you have to keep that at the top of the pyramid of importance.” says Black. “I don’t foresee Jason, no matter how popular this gets, I don’t see us becoming, you know, Keith [Richards] and Mick [Jagger] on separate planes for our shows, I don’t think that’s in our future.

Jason Stewart and Chris Black.

“But I think part of that is because we started this as adults with life experience. I think a lot of creative ventures that are successful are started when [people] are really young and you don’t know how to handle things; you have no experience, you don’t know how to talk about money, you don’t know how to deal with attention. I think starting this at our age is really helpful, because we understand how the game works a little bit and we understand how to communicate with each other. It’s just a different playing field.”

The pair’s willingness to follow all and any conversational tangents allows for such things as BJ Novak from The Office on bespoke sushi, being a cat mum with Naomi Fry, and seeing celebrities at the gym with musician Jason Isbell.

Both Black and Stewart see conversation, especially with strangers, as something of a lost art. “I think there’s definitely a generational shift, where it’s like, why would I talk to someone when I have my phone and my computer and my TV and my iPad?” says Black.

“I think it’s like anything else, it’ll probably return to … people will be desperately craving conversation in a more ‘old school’ way. But yeah, I think there’s definitely [been] a shift for sure. People use Snapchat instead of talking to each other, you know – it’s a real thing.”

Jason Stewart and Chris Black with Alexa Chung.

“As bad as that is for humankind and the future of our world, I want people to get progressively worse at having conversations so they have to listen to the podcast as though we’re like going to the museum of talking,” interjects Stewart.

He says a lot of people, especially “extremely online” ones, are yearning for “a real conversation”.

Something both can attest to is that, at the very least, it passes the time. “Chris and I are from an age and generation where if we’re bored we can entertain ourselves quite well just by talking to a stranger or even a friend or anyone – the waiter at the restaurant you’re at,” says Stewart. “We both have that skill where we can amuse ourselves with anyone.”

As for dream guests, Black nominates the British singers Jarvis Cocker or Liam Gallagher from Oasis, while Stewart opts for celebrity lifestyle maven, friend of rapper Snoop Dogg and one-time jailbird Martha Stewart. Ultimately, he says, you want someone who isn’t what they seem.

“I think when you look at a celebrity, [who] you know is really interesting and cool behind closed doors, but they kind of have a put-on persona publicly … those are the people I want to talk to the most because they’re a nut that looks fun to crack, you know? And to show a side of them that the other world doesn’t get to see unless they’re a close friend.”