Welcome to Message Box Mailbag #3. Hope everyone has survived Halloween and that those with young kids and dogs are prepared for daylight savings tomorrow. Another great set of questions this week — far more than I can answer. Like last week, I tried to pick questions that reflected consistent themes and covered what many of you asked about. As a reminder, these will come every Saturday as a special feature for paid subscribers. Subscribe today to read these posts and ask anything you want. Don’t forget to post your questions for next week’s mailbag in the comments section of this post. David
Answer This is a question near and dear to my heart. I have spent the last decade traveling the country, going from meeting to meeting, boardroom to boardroom, trying to convince the Democratic donor class to take some of the billions lit on fire every cycle on TV ads and invest it into content and progressive media. After years of failing, we are finally seeing some money move toward winning the information wars. But your question isn’t about progressive media like Pod Save America or investments in content creators like Brian Tyler Cohen or Carlos Espina. You want to know why they aren’t spending their money on traditional journalism... Continue reading this post for free in the Substack app
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Saturday, November 1, 2025
Should Liberal Billionaires Invest in Journalism?
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November 11, 2025
In 1918, at the end of four years of World War I’s devastation, leaders negotiated for the guns in Europe to fall silent once and for all on...
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