1440’s newsletters are short, popular and profitable

1440’s newsletters are short, popular and profitable

Newsletters are not a new idea. Yet every few years the media business rediscovers them, anyway — either as a way to quickly launch a startup with bigger ambitions, or as a standalone business. Tim Huelskamp took the second route in 2017, when he co-founded 1440 — a newsletter that promises to quickly bring you the most important news of the day. Again — not a new idea. But Huelskamp seems to have figured out how to build something pretty big: He says 1440 has 4 million readers, and is turning a profit on something like $20 million in annual revenue. How’d he do it? What’s he going to do next? And how will he compete with AI companies that can do all of this faster, and cheaper? I’m glad you asked: I’ve got the same questions, so I asked him myself. Learn more about your ad choices. Visit podcastchoices.com/adchoices

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Episoder(596)

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...

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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 Jul 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 Jul 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 Jul 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 Jul 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 Jul 58min

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