I wear two hats right now. As an attorney at Lowenstein Sandler, I spend my days – among other things –helping founders prepare for investor due diligence. As the founder of Fansmit, I’m currently living through that same process myself, raising a pre-seed round. That combination has taught me something I didn’t fully appreciate from the legal side alone: questions investors ask aren’t a perfunctory checklist topunch. Rather, they’re a window into how investors actually evaluate risk, and founders who understand why a question is being asked answer it far better than founders who just answer what was asked.

Before your first pitch call, know your own numbers and documents inside out, your formation paperwork, cap table, IP assignments, key contracts, and financial model. The founders who win the room have those answers ready before anyone asks. To borrow a concept from David Letterman, here are the top ten questions that come up in nearly every pitch call I’ve had recently, and what’s really behind each one.

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