You're asking the wrong questions — and it's costing you

Wes Kao put out a note on what he calls the fundamentals of sharing your point, and there's something worth paying attention to here that goes beyond the usual startup playbook.

The gist is this: most people are asking the wrong questions when they try to figure out what to say, what to pitch, what to build next. Instead of starting with the right questions, they start with the wrong ones — and then wonder why nothing lands. Wes frames it as a discipline problem, not a talent problem. You don't need more ideas; you need to ask the right questions before you start generating ideas.

The real move is figuring out what's actually interesting to you — not what's trendy, not what's raising the most capital, not what your cousin's side hustle is doing — and then asking what questions about that thing are still unanswered. That's the part that trips people up. Everyone's chasing the same questions and everyone's wondering why nothing feels new.

Why this matters for us: When Brown founders keep asking the wrong questions, we end up building for Silicon Valley's calendar instead of our own.