How Bari Weiss Took Over the Media

Bari Weiss is punk rock.

There's really no other way to explain what Bari Weiss has accomplished in the past four years since very publicly resigning her (relatively new) position as an editor for the New York Times. The DIY ethic and fiercely independent spirit with which she launched The Free Press and rode it to a practical coup in the corporate news world is about the most punk-ass thing we've seen in media in a long time.

With the recent announcement from Paramount that Weiss has been named the editor-in-chief of CBS News, the frenzied rumblings of the journalism world have been trying to figure out just how the forty-one-year-old writer stormed the gates of the Fourth Estate and won.

Since its founding in 2021, The Free Press has amassed more than 1.5 million readers and $15 million in annual subscription revenue, according to a person with knowledge of the company’s finances. In an interview, Hamish McKenzie, a co-founder of Substack, called CBS’s acquisition of The Free Press a “strong recognition that we’re in a new generation of media now.”

“What is undeniable is The Free Press built a new media business in a time when everybody thinks the news is dying as a business — and got it to a place of flourishing in a space of three years,” he said.

It's rare that disruptors are so effective so quickly in challenging institutions like the media. When The Free Press first came on my radar, I immediately thought of Arianna Huffington and the Huff Post. However, Huffington had quite a different starting point, obviously, with significant advantages over Weiss in terms of establishing a name and a news site. And, to be honest, I was never a fan of Huffington and her site which I believe took advantage of writers and certainly exploited many of them, making an obscene amount of money while paying virtually no one for the content.

Weiss deserves props for taking what amounts to a newsletter on the emerging platform Substack and turning it into a thriving news site which clearly filled a niche and a gap in the world of online freelance journalism. And with a prolific publishing schedule and podcast, she definitely put in the time and the effort to quickly build and grow her own unique platform. This was nothing short of pure DIY hustle, and Weiss carved out a market where none had existed.

Granted, as impressive as Bari Weiss' success with The Free Press is, the new leadership gig with CBS News is drawing serious scrutiny and criticism, and it undoubtedly should. Weiss is definitely a skilled writer, editor, journalist, and entrepreneur, but nothing in her career yet truly qualifies her to head one of the major news and media organizations in the world. And, while her greeting letter to her new team was certainly appropriate with many valid positions, her continued connection to The Free Press and its incorporation into the Paramount/CBS orbit is rather suspect. 

While The Free Press is in many ways a fresh and valued voice in the media landscape, it is by no means an unbiased, non-partisan, "fair & balanced" news site. The same goes for Weiss herself. And it's entirely fair for anyone to have and promote their ideas, perspectives, angles, preferences, and attitudes. In fact, that is the job of commentary writers, the side of journalism from which Weiss comes.

So, it will certainly be interesting to see what comes next for Weiss and The Free Press. It's definitely been a raucous and impressive ride so far.