Tell HN: Things I Learned From Meeting an Angel Investor
* Know in advance of the meeting whoever your most popular competitor would be. Be prepared with a damn good answer to answer the question "Why wouldn't I just use [most popular competitor]"?
* Be prepared with a damn good answer to the question "How are you going to get users?" My experience is the best answer is to both have something on your website that can go viral and also have a good way for users to easily refer more people (like searching their address book for contacts, clicking a button to send somebody an email, etc). Tweets and Facebook Likes are not aggressive. You need to use email.
* When you're making a mock-up of your start-up, be sure to make a mock-up of however you plan to make money. The monetization plan is the last thing on the founder's mind and the first thing on the investor's mind. Potential investors will absolutely ask "how are you going to make money?" "We're going to get big fast and then rely on Google/Yahoo/Facebook to buy us out" is crazy talk and your investor's won't believe it. Seriously: Even if you have a good answer for monetization, BE PREPARED TO ACTUALLY SHOW INVESTORS AT LEAST A MOCK-UP OF A MONEY-MAKING FEATURE ON YOUR SITE - SOMETHING THAT WILL ACTUALLY ACCEPT REAL PAYMENTS WHEN ITS DONE!
* Many, if not basically all, start-ups these days rely on user-submitted content. Be prepared to answer how you will deal with the legalities of that and potentially compensate the users that do the submitting.
It was a tough sell with this potential investor. It didn't work out but I learned a lot. As I meet with other investors, I will share my experiences.