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Exclusive: Progressive megadonors bet big on content crea...
David Weigel · 2026-05-01 · via Semafor

While the retreat in New Mexico, attended by 200 alliance members, included discussions of other investments — it ended with an emergency strategy session on responding to the Supreme Court’s Louisiana v. Callais decision — the emphasis on new media delighted activists who’ve worked to grow progressive channels.

“It was hard to get folks in the pro-democracy movement, on the left, to actually understand how the media ecosystem has changed,” said Tara McGowan, who in 2019 founded the left-leaning Courier Newsroom, which was closing in on 10 million subscribers.

“The old way of working through traditional and legacy outlets was not going to actually get factual reporting, never mind progressive values-driven reporting, in front of the American people,” she added. “The DA stepping up to the plate is a very good thing for democracy.”

Convincing donors that left-leaning media was worth investing in had been difficult. Some, said McGowan, associated the idea with Air America, a Bush-era startup that lasted less than six years. It produced or trained progressives who would end up hosting influential shows on traditional media, like Rachel Maddow, or popular independent programs, like Sam Seder and Marc Moran.

But the liberal philanthropy world saw more immediate benefit in funding turnout and campaign work.

“Everybody has their own media diets, and a lot of the donors and philanthropists in this movement are older, to be really frank,” said McGowan, 40. “I still find that there’s a pretty big learning curve with Boomers or older people about how media works today.”

Polls have consistently found that Democrats are more likely to trust established media outlets, while Republicans barely trust them at all. Democracy Alliance donors were being urged to stand up content creators whose work got to young voters that didn’t consume old media at all.

“I live in New York, and I saw the Mamdani campaign use media and tactics that reached people, that spoke to people, that resonated with people, and that was joyful and positive and compelling,” Shifman said. “It doesn’t have to be negative to reach people.”

Doing that didn’t mean moving to the right on cultural issues, either. “That is not why we are losing, because the Democrats are too ‘woke,’” said Shifman. “Our strategy really is about meeting people where they are. And we also need to have a vision of what we are going to do to improve people’s lives.”