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Stack Overflow users don’t trust AI. They’re using it anyway

Today, I’m talking with Prashanth Chandrasekar, who is the CEO of Stack Overflow. I last had Prashanth on the show in 2022, one month before ChatGPT launched. While the generative AI boom had tons of impact on all sorts of companies, it immediately upended everything about Stack Overflow in an existential way. Stack Overflow, if […]

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Sen. Ed Markey wants media companies to fight for the First Amendment

Today, I’m talking with Sen. Ed Markey of Massachusetts, and you’ll hear me start with the only question I think anyone should be asking any politician in the federal government right now: What the hell is going on here? Sen. Markey didn’t mince words with his answer. You’ll hear him compare the Trump administration to […]

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Square’s product chief on the death of the penny and the future of money

Today, I’m talking with Willem Avé, who’s head of product at Square. You know Square — it was started by billionaire Jack Dorsey, of Twitter fame, more than 15 years ago, and it got big on the back of that little magnetic reader that plugged into the headphone jack of the iPhone and let small […]

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