Pod Save America’s Jon Lovett wants to win an election and make money

Pod Save America’s Jon Lovett wants to win an election and make money

Jon Lovett and his cofounders at Crooked Media are a good story - former Obama aides who started their own media company after the 2016 election, and are now generating 25 million podcast downloads a month. But for a few weeks this summer, after they became prominent voices in the push to replace Joe Biden on the Democratic ticket, their story got even more interesting. I’ve wanted to talk to Lovett about that experience for months, so a week before the election seems like good timing, no? Also discussed here: How to navigate a media landscape dominated by Donald Trump; Elon Musk, and the upside of getting kicked off of Survivor. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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The $12.5 Billion Lakers, the NFL’s TV Fight, and Sports Media’s Big Split

The $12.5 Billion Lakers, the NFL’s TV Fight, and Sports Media’s Big Split

Sports teams keep selling for more money because, in theory, their media rights keep becoming more valuable. But the companies that actually pay for sports TV are starting to push back. John Ourand o...

19 Aug 42min

Joanna Stern on the New Siri, OpenAI’s Weird Gadget, and Life After the Wall Street Journal

Joanna Stern on the New Siri, OpenAI’s Weird Gadget, and Life After the Wall Street Journal

Joanna Stern spent more than a decade explaining technology to Wall Street Journal readers. Now she’s doing it on her own — with a new media company, New Things, and a new book, I Am Not a Robot, abou...

12 Aug 48min

Oliver Darcy on Status, Bari Weiss, and Why Media Reporters Are Too Soft

Oliver Darcy on Status, Bari Weiss, and Why Media Reporters Are Too Soft

Two years ago, Oliver Darcy left CNN and launched Status, a paid newsletter focused on the media business. The basic bet was that readers would pay for the scoops and insider reporting he had been pro...

5 Aug 52min

Lucas Shaw on Warner Bros' Limbo, Netflix's Anxiety, and Hollywood’s Sort-of Comeback

Lucas Shaw on Warner Bros' Limbo, Netflix's Anxiety, and Hollywood’s Sort-of Comeback

When I last talked to Bloomberg’s Lucas Shaw, Netflix was buying Warner Bros. Discovery. Six months later, Paramount has the deal — but, surprisingly, it’s on hold while a group of states tries to blo...

29 Juli 44min

Substack Wants To Become A Social Network; Beehiiv Wants To Stay Invisible

Substack Wants To Become A Social Network; Beehiiv Wants To Stay Invisible

You are a normal person, so if you think about “people writing their own newsletters” you probably think: “Substack”. But just as Xerox isn’t the only way to make photocopies, Substack doesn’t own th...

22 Juli 42min

Inside Podcasting’s Fight Over Netflix, YouTube, and Creator Control

Inside Podcasting’s Fight Over Netflix, YouTube, and Creator Control

Chris Balfe is the CEO of Red Seat Ventures, the company behind some of the biggest names in podcasting, including Megyn Kelly, Tucker Carlson, Bill O’Reilly, and, more recently, Kill Tony. Since we l...

15 Juli 45min

"We’re in a Race Against Time," Joe Kahn on Running the New York Times in the Age of AI Slop

"We’re in a Race Against Time," Joe Kahn on Running the New York Times in the Age of AI Slop

Joe Kahn runs the New York Times newsroom, which means he runs the most powerful news operation in the world. He joins me to talk about what that power is for — and why he thinks the Times’ next big t...

8 Juli 1h 4min

Encore: Inside Joe Weisenthal's brain

Encore: Inside Joe Weisenthal's brain

We originally published this interview with Bloomberg's Joe Weisenthal on Feb. 11, 2026, and it's one of my favorite chats of the year. We'll be back with a new conversation on July 8. If Joe Weisent...

1 Juli 58min

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