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Uncomfortable Conversations with Josh Szeps

"Substack's Founders on the Future of the Media" with Hamish McKenzie & Chris Best

Uncomfortable Conversations with Josh Szeps

Josh Szeps

Comedy Interviews, Education, Society & Culture, Comedy, Self-improvement

4.5905 Ratings

🗓️ 1 September 2025

⏱️ 76 minutes

🧾️ Download transcript

Summary

What is the future of the media? Are we doomed to inhabit our own social-media news bubbles, tailored by algorithms to keep us “engaged”? Will readers return to old-school news outlets? Or is there a third way? That’s Substack’s bet. The platform is transforming the media landscape by enabling journalists and creators to speak directly to users.
 
Just as Josh was embarking on Substack’s first-ever around-the-world livestream marathon, the company announced a new round of funding, vaulting it past a billion-dollar valuation and making it one of Silicon Valley’s “unicorns”. 

Substack’s co-founders are Chris Best and Hamish McKenzie, who were kind enough to sit down with Josh to discuss the conflict between free speech and hate speech, the decline of legacy media, the role of video, the challenges of living in a social-media world… and the future of their little company that’s becoming very, very big.

Transcript

Click on a timestamp to play from that location

0:00.0

Duhay, humans. Welcome to the safe space for dangerous ideas. Here's a dangerous idea for you.

0:08.4

As the legacy media struggles to maintain trust, maintain market share, as more and more

0:16.2

young people get their news from scrolling, I was going to say mindlessly, but that sounds a bit

0:21.1

pejorative, doesn't it?

0:22.4

Scrolling actively and delightedly and delightfully through the labyrinth of their social media

0:28.6

feeds.

0:30.0

We are kind of doomed to a fate in which everybody will inhabit their own social media news bubble,

0:37.0

tailored for them by algorithms designed entirely

0:40.6

to keep us all, quote unquote, engaged, to keep us clicking, to keep us scrolling, to keep us

0:47.3

watching, to keep us liking, to keep us commenting, things that either pander to what we already

0:53.4

believe or demonize what we don't already believe.

0:58.0

That is the sort of dystopian possible fate of our information ecosystem

1:03.0

in the absence of gatekeepers like big public broadcasters that everybody tunes into at the same time every evening

1:09.4

to find out what's going on in the world

1:11.6

from an old straight white male talking at them.

1:15.8

Substack is trying to do something different, and today's episode is an interview with the two

1:20.8

co-founders of Substack, Chris Best and Hamish McKenzie.

1:25.8

I've just come off the back, as I'm sure you are no doubt aware,

1:29.1

having been bludgeoned over the head with it for the past few weeks, a world tour.

1:33.4

Substack's first ever substack live around the world podcast marathon. Lots of great content.

1:40.1

So if you've been asleep at the wheel, then go back over the past a dozen odd episodes.

1:44.4

And almost every single one, I think, is worth listening to.

...

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