Journalists or Creators? How Media Entrepreneurs Are Reshaping News

On with Kara Swisher

New York Magazine

News Commentary, News, Society & Culture

4.2 • 2.2K Ratings

🗓️ 31 July 2025

⏱️ 66 minutes

🔗️ Recording | iTunes | RSS

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Summary

Legacy media isn’t dead, but journalists are leaving traditional outlets in swarms to launch their own newsletters, podcasts and social media ventures, and they may be forcing a reboot. As one of the early media entrepreneurs (and a trusted advisor to many of those who aspire to follow in her footsteps), Kara sits down to discuss the current landscape with Oliver Darcy, founder of the “must-read” media newsletter “Status”; Katie Drummond, Wired’s global editorial director; and Dave Jorgenson, The Washington Post's former “TikTok Guy”, who has recently launched his own site, Local News International. In a freewheeling conversation, they unpack the challenges of audience capture, the looming shadow of AI, and the surprising (financial) realities of being an independent journalist. Questions? Comments? Email us at [email protected] or find us on YouTube, Instagram, TikTok and Bluesky @onwithkaraswisher. Learn more about your ad choices. Visit podcastchoices.com/adchoices

Transcript

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0:00.0	Oliver, were you late?
0:02.0	I was two minutes tardy.
0:03.0	Yeah, right.
0:04.0	The rest of us were here on time.
0:06.0	Late is a strong word.
0:08.0	It's on.
0:09.0	Hi, everyone, from New York Magazine and the Vox Media Podcast Network.
0:22.1	This is on with Kara Swisher, and I'm Kara Swisher.
0:25.0	I don't know how many of you saw the picture of me in the New York Times a couple months ago, scaling a climbing wall.
0:30.3	It came out just after Scott Galloway and I re-upped our contract with Vox for our suite of podcasts.
0:36.0	But it was really, in my mind, the way I think about
0:38.7	media and entrepreneurship. I've been launching media ventures for over two decades. I am kind of
0:44.8	the OG of this kind of stuff, but it started with All Things Digital Conference with
0:49.2	Malta, we started at Dow Jones, which then morphed into the site All Things D, 2007. I wanted to do my
0:56.2	own thing because I was the world's worst employee, and I decided to work for myself because I could only
1:01.4	annoy myself. And one of the biggest learnings I got out of those days is if you have a great idea,
1:06.4	go ahead and do it. I kept doing it and shifted many, many times. In 2014, Walt and I broke off
1:13.1	and started Recode, and from there, we did the Recode Conference. We sold it to Vox Media. Then I
1:18.4	started a podcast at Vox. And here we are. The early Internet days with the blogging culture was a
1:24.2	moment in big upheavals in journalism and were in another one of those moments right now, sparked by the balkanization of the media landscape and AI. My guest
1:32.8	today are three media makers who are among those stirring things up, both within legacy media
1:37.7	and on their own. Katie Drummond is the global editorial director of Wired, where she leads
	...

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