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On today’s episode, I sit down with Brian McMahon, co-founder and CEO of Pickle, a peer-to-peer rental marketplace built around the idea that the things sitting in our closets can function as income-generating assets.

Brian started his career in finance before teaching himself how to code and launching what was originally a social polling app designed to help people make purchase decisions. But after noticing that users were constantly recommending items they already owned, he and his co-founder (Julia) pivoted toward a marketplace model focused on renting, lending, and reselling personal items.

In this conversation, we talk about what that pivot looked like in practice, the scrappy early days of photographing inventory in friends’ apartments, personally completing thousands of deliveries across New York, and how an asset-light model shapes everything from supply dynamics to operational complexity.

We also break down how Pickle generated its first network effects, lessons from fundraising, and how Pickle is thinking about expanding into new categories as it works toward unlocking underutilized consumer assets at scale.

I learned so much from Brian and I hope you enjoy the conversation as much as I did.