[UPDATED] If We Meet, I Will Ask You…

After blogging about a variety of topics, I find that they form the core nucleus of the things I care about before investing in a startup. Yes, I also care about the usual stuff like smart entrepreneurs, great idea, etc. But I think there are things that I’ve been focusing on assuming we get past the basic stuff.
So if I meet with you, you can expect discussions on:
1. What’s your world domination plan (and more on why it’s important to have one)? How can you avoid just becoming another small business which is not a reason for not existing, but does bring danger to us investors?
2. I’m most likely going to try to talk you out of being an entrepreneur.
3. Most startups I meet are working on me-too products, even if they don’t think so. How can you not be about just developing a me-too product?
4. Are you planning on lasting two years? If you aren’t and you need time and money to pivot, you won’t be able to raise money in this climate because second chances are impossible to come by.
5. How are you going to make money? Please, no more projects that are just going to gain lots of users…
6. If I were to envision the The Ultimate Product (and Part 1.5), would what you’re building be that product, or on the path to that product?
7. How are you going to gain customers – distribution is by far the number one problem facing internet startups today (see me-too post and my combining startup investing and distribution post).
8. [UPDATED: 2/4/11] How will you get to $100,000,000 in revenue per year?
9. [UPDATED: 6/14/11] Study past startups and competitors and learn from their mistakes and successes. Tell me how and why you’re not going to let history’s mistakes repeat themselves.
My hope is that not only you will have great answers to all these questions, but you will also internalize and truly believe in those answers yourself, and that your answers aren’t just lip service. Hope to see you soon at a cafe near you!