[GianFabien]

The key to the disparity is that potentially having skin in the game is what makes a potential investor more analytical and critical than any non-investor. Furthermore, every investor has a different set of criteria. I don't believe that any simulation whether available persons or some software can ever be a viable substitute for reality.

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.

[fzwang]

I used to work in VC and second this. Nothing really preps you better than the real deal. Line up some practice rounds with low-stakes investors first.

The issue with using founders/friends is that they're too emotionally invested in you to ask the hard questions in ways the investors will. Founders also think differently than investors. For example, a friend who has built companies before would look at a potential issue and their "operator brain" would automatically come up with ideas on how to address it. As a result, they may downplay the problem. Whereas an investor may laser in on it to test your thinking/confidence.

If you had to practice, making the question submission anonymous (as you can) may help. I know I hate giving harsh feedback to friends directly, even if they ask for it. The sting still lingers around. Not knowing who asked the question could be helpful, but it's possible they would still be able to tell if they know you.

[johnzakkam]

This is incredibly valuable advice, thank you! You're absolutely right that nothing replaces real investor feedback - the skin in the game factor is huge. Your process of working up from least preferred to most preferred investors is brilliant and something I wish I'd known earlier.

I'm thinking the tool might be more useful in the prep phase, before you even reach out to that first investor on your list. The goal wouldn't be to replace your process, but maybe help founders feel more confident before that first real conversation? Especially founders who don't have experienced networks to practice with initially.

Does that positioning make more sense, or do you think even that prep stage isn't worth the effort vs just jumping straight into real conversations?