The Startup Ideas Podcast · Greg Isenberg

The 2026 Anti-Trend That Will Make Millions

·43 min·3 clips

Jonathan rented an entire Italian village for a retreat and sold $7,800 tickets in two days via DMs.

AI is the setup. The cold open asks the blunt question: if you had to start over, how would you make a million dollars in 2026? Jonathan Courtney answers with the move most software people are ignoring. Instead of building another GPT wrapper or chasing audience growth, he points to IRL experiences AI cannot copy in a weekend. Then the idea gets concrete. Courtney explains how an Italian village retreat came together after COVID, when people wanted to be in the same room again. The screen share helps. They pull up the actual video, laugh through the thumbnail, and treat the whole thing like a live teardown instead of a pitch. The setting is the hook. Courtney says he and Laura first visited the Workation Village in Italy for a small team retreat, then started thinking bigger. The place could be rented as a full village, with buildings, rooms, a swimming pool, and even a forest. It is a little ridiculous, which is why it works. That becomes the business point. If everyone is piling into software, the harder thing to clone may be the room, the place, the people, and the taste behind it. The host keeps asking for specifics, including how DMs helped fund it and why a huge audience is not required. The episode ends casually with Courtney's Unscheduled CEO work, some social-platform joking, and the hint of a part two.

As heard by us

A contrarian founder story that turns IRL effort into a practical edge.

Jonathan Courtney's point lands as a case for building IRL when the market is crowded with AI plays. The pull comes from the concrete example: renting an entire village in Italy and funding it through direct messages.

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