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I sat down with Sam Thompson (⁠⁠https://x.com/ImSamThompson⁠⁠) again, and this time we tried something completely different. We used a random word generator to come up with totally random words and then challenged ourselves to turn each one into a real business idea that could make $20K a month. What started as a fun experiment turned into one of the most creative brainstorming sessions I’ve ever done.

We came up with ideas like an Office-themed chess set, a blue-collar Stoicism community, and even a nightclub marketing agency called Full Lounge. We debated which ideas would actually work, which ones could scale, and how fast each could become profitable. Sam also shared why most people overcomplicate online businesses when simple local plays like garage cleanouts can hit $20K a month with just one person running them.

We wrapped up talking about how important it is to start small, stay consistent, and focus on momentum instead of waiting for permission or the “perfect” idea.

Enjoy!

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IT: Welcome to Derry - S01E02 - The Thing in the Dark