To Find Obsession, Ask a Simple Question and Keep Going Deeper

A founder-investor who holds hundreds of conversations with early builders each year uses them to spot generational talent before there is traction. The system compresses those calls into four checks, and one of the most usable is a test for depth of obsession.

The method borrows from investor Marc Andreessen. As the founder-investor puts it, "Ask a simple question. Then go deeper. Then keep going." After enough layers, it becomes clear whether the preparation is real. "Obsession is revealed in the details."

In practice, that means staying on one topic instead of moving across topics. Pick how the product works, who exactly will use it first, or what breaks at scale, ask for the plain version, then ask what sits underneath that answer, and then what sits underneath that. Do not rescue the other person with a new question when the specifics get uncomfortable.

Listen for whether the answers get more specific as you push. The strong candidates can talk through the hard parts of the work, and some of what they say is not what you would expect. A good conversation leaves you with something unexpected and useful.

Be wary of people who speak in generalities or abstract principles. One red flag is when answers stay vague under pressure.

If you want to try it this week, you could start with the simplest version of the question you actually care about, and keep asking why and how exactly, even past the point where it feels polite to stop.