Hi Rob - per your comment, I like the idea of beta-testing executive summaries before peers before pitching to potential investors. I will put together a version of an exec sum I've used in the past to post here.
In terms of questions investors ask, in my experience I have been asked the following regularly:
- Who is the target market/user for your site/product?
- What is your typical user's pain, and how does your site/product address it?
- What's your marketing plan?
- What does it cost for you to acquire a customer/user?
- What is the size of the market, and what share of the market can you achieve with the product?
- Who is on your team? Are they all full-time? What have they done before in this space?
- How much money are you raising, and what will it be used for? How much runway will it give you?
- Who are your competitors, and how does your site differ?
- How do you think you can exit (i.e., "How will I make big money here?")
- Who is on your Board of Directors (or equivalent)?
- Do you have any tech that is unique and/or patentable?
- What's your 'secret sauce'?
I'm sure I can think of other investor questions, but these are front-of-mind this morning.