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Investing in Ambiguity

Reputation Over Reach

What Luxury Can Teach Venture

The best early stage founders are not fully formed. They are still becoming who they are. And that makes them hard to evaluate using conventional filters.

As investors, we like to ask about traction, frameworks, market sizing. But many of the best decisions I have made came from backing someone before they had answers and sometimes, before they even had language for what they were building.

The mistake most funds make is thinking that clarity is proof of maturity. It is not. It is often just good coaching or good storytelling. But it says nothing about what that person will be like in year two or year four, when things get real.

I have started looking for different traits. Curiosity without flattery. Technical discomfort with being vague. Emotional calm in moments where most people posture.

Some of the best founders I know stumbled through early pitches. They built slowly. They changed their minds. But they had one thing that mattered more than polish, they had tension. A deep pull toward a problem they could not ignore.

I call this investing in ambiguity. It is the belief that clarity comes from movement, not from slides. That identity is earned during execution. That conviction is not something you present. It is something you live through.

This is not about lowering standards. It is about understanding where real potential hides. Not in the performance, but in the persistence.

As funds become more metrics driven, I think the best investors will return to instinct. Not gut feeling. But long cycle pattern recognition. The kind that sees beneath the surface and finds the people who are still shaping themselves, but who will, in time, build something that shapes others.