In probably every meeting we’ve taken to date, there’s one question we make sure to ask:
"Walk us through a deal."
You’d think after 100-plus interviews we’d pick something else, but that one prompt does two jobs at once:
Spot the universal pain point.
Surface the weird edge cases we haven’t heard before.
Most founders fixate on the shared headache because that’s where the TAM slide lives. Kash and I agree it’s critical, but the second bucket is where the fun hides. Edge cases reveal how adaptable your product really has to be when the perfect-world workflow inevitably breaks.
So what do the edge cases teach us?
The “one-off” is never truly one-off. That oddball you heard from a client? Two weeks later another fund mentions the same workaround in a different gown. Edge cases rhyme; if you solve one elegantly, you’re halfway to solving five.
People want Legos. Canva works because it doesn’t care whether you’re making a birthday invite or a pitch deck. It hands you Lego bricks and gets out of the way. Software for private markets should do the same: let teams snap in a customer concentration calc, rip it out, reuse it on the next deal, no tickets to engineering required.
We’ll keep opening with “Walk us through a deal” until the answers get boring. Luckily for product people, they never do.