What are the signs of an entrepreneur who is over-prepared for meetings with investors?

Just a few thoughts to add.

Things that are a negative for me and are sort of in the “over-prepared” category:

  • A written business plan.  A deck is great.  And a detailed operating plan in a Google Sheet or Excel is an A+++.  But … a traditional, 20+ page written business plan though … tells me you don’t know how to start building the product, but instead, need to just talk about it more.
  • Too many / wrong folks at pitch.  Never, ever bring a consultant or anyone that isn’t an employee.  Never bring someone that isn’t full-time.  Ever.  Bringing a wing-man is great.  It shows you have a team.  Bringing 2 with you — only do this if there’s a real reason to do so.
  • A thoughtful exit strategy.  I’m entering, not exiting.  This tells you may take the first off ramp.  Which may be the right thing for you.  But — I immediately lose confidence in Unicorn potential.
  • Talking too much about my other investments / my portfolio.  Cool you know the companies.  But kinda weird when you know them too well.  It’s not your space, not directly at least.
  • Talking about specific terms (too much / too early).  Telling me the exact terms of the raise in a pitch or when we’ve just met … unless you’ve already closed a lead, and therefore, have real terms … is too rookie.  Telling me how much you want to raise — very helpful.  Dictating very specific terms before you are in a position to do so, before we’re looking to do a deal together … tells me I may not want to work with you.  It tells me you may be trying to over-engineer something that shouldn’t be over-engineering at this stage, at least.

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