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1. Who else have you spoken to?

I believe every single investor asked this early on and I’m not completely sure why they cared so much since they should be basing their judgment and strategy on the strength of the idea and not on its popularity. I think it’s because Silicon Valley is a lot like high school in that you’re basically as cool as the people who talk to you. Being funded by Sequoia, is not unlike dating the hottest cheerleader in the squad. Then again, maybe it’s just natural human curiosity. Either way, it’s a good idea to keep at the top of your head who you’ve talked to and their appropriate place in the pecking order.

2. How will you make money?

If Adsense is your stratetgy, you might want to start thinking of some alternate revenue models. After one investor asked us this question, he quickly said under his breath in a little prayer, “Please don’t say Adsense.” If you already have a million users, then the investors are going to listen to you no matter what you have planned. That said, investors are getting hip to the notion that funding a Web 2.0 startup that’s obsessed more with the technology than the revenue is just asking for trouble.

If you need help thinking of alternative revenue models, I highly recommend checking out Startup Pricing Models and Giving Your Software Away For Free for some good reading on the subject.

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