Navigating the AI Investment Landscape: Risks and Strategies

Henry Blodget can’t help himself. The Business Insider founder is starting another media business, knowing full well how difficult the industry can be. You can watch him build it in real time: Regenerator on Substack, and Solutions on TikTok, YouTube and everywhere you hear your favorite podcasts.

Henry — who hired me to work at Business Insider in 2007, back when it was called Silicon Alley Insider — sat down for a chat about what’s changed in media and the internet over the years, and what hasn’t. We also took time to talk about the AI boom, whether it’s a bubble, and why bubbles can be useful. It’s a blast from the past and a look at the future, all in one chat. Enjoy!

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