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Ben Gilbert on how Acquired launched their paid podcast

Ben Gilbert on how Acquired launched their paid podcast

It’s weird, but in some ways, side projects require better strategy than regular businesses. They’re so easy to quit. Even if you love it, y

Dec 19, 2019 · 10 min readUpdated May 15, 2026

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It’s weird, but in some ways, side projects require better strategy than regular businesses.

They’re so easy to quit. Even if you love it, your hours are constrained, so you have to be absolutely ruthless in choosing what not to do. (A critical skill in creating any strategy.)

Plus, there’s pressure to build the right thing from the outset. If the project doesn’t find an audience quickly, it usually dies on the vine. I mean, who wants to pay the emotional toll of pivoting a project that’s supposed to be a fun thing?

But even if you beat the odds, and manage to make something people want, the challenges just get tougher. You have to decide how to spend your limited time and money to make it grow. It’s a process that forces you to get extremely clear on what your goals are.

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