Thinking about building a tool that generates realistic VC questions based on your pitch deck - the skeptical stuff like "Your TAM math doesn't add up" or "Why can't BigCorp clone this?"
Is this actually a problem other founders face? How do you currently get honest pitch feedback before investor meetings?
I suggest a simple process, one that I have used in the past:
Make a list of at least 5, pref 10+ potential investors.
Rank them in order of how much you would like them to invest.
Start with the lowest one on the list
Present and gather feedback
Refine pitch deck to incorporate feedback
Repeat with next investor, working up the list, repeat the feedback and refinement process.
Ideally by the time you reach your more ideal investors, your pitch deck is much improved and you increase your chances of a favorable outcome. In fact, you could end up with bidding rounds.
Often friends aren't simply polite, they just don't have the experience. They haven't invested in things that fail... heck, many won't even know a guy who invested in a failure. And when they do, it's a single data point and they'll come to some dumb conclusion like "it was losing money," as if every successful startup wasn't.
And you will encounter them again again even during your GTM phase.
The team at Wiz (acquired by Google for USD 32 billion) has the perfect strategy to overcome the sugar-coated feedback when pitching. They called it the "false positive"
I covered it here https://www.sandrasletter.com/p/the-design-strategy-behind-t...