How long to wait for angel investor?

I have a big web project which I and my co-founder began our development on. We've been talking to our angel investor for a long time. He is very responsive but we cant get a final investment number from him. What is a delicate way to approach him to see if he's in or out. We want to form legal documents. What do you think?

Angels are the ones who are investing their own money. Naturally, they wouldn't take a call as soon as you'd expect them to. They are driven by their personal tastes and choices. Also, they would take longer time to get convinced about your position if you are not within their areas of expertise. In such a case you may have to go an extra mile to convince them.

With regards to a specific number, that's a stage which comes much late. First you need to make sure that the angel is really 'in' for your startup.

If you don't yet know how far you have gone in establishing the relationship, I think it would be too early to even think of any legal formalities. (Is it that you are, inadvertently, shooing the angel off, by thinking about legal aspects so soon?) As far as legal documentation is concerned, it's more a need for the investor than that of yours. After all it's his/her money at stake. So don't get into it so soon.

Concentrate on addressing the apprehensions of the angel. And remember, don't deviate from your main business. You shouldn't concentrate so much on securing an investment that your business get affected. In a worst case scenario, if the angel backs off, you shouldn't be in a situation where this exercise has taken a toll on your business and you are doomed.

You have one of several possible issues:

1. the angel doesn't want to invest, but doesn't have the courage to tell you "No"
2. the angel would invest, but has no reason to invest today
3. he is not a "lead", so he is waiting for another angel to decide on terms. It's often called "social proof"

Each problem has its own set of solutions. You first need to find out which it is. For instance, if the angel has been quizzing you about "who else is investing", you know you are in scenario #3.

In the angel game, it's all about the relationship. For whatever reason, this angel is still not convinced that your idea is worth investing in. As Sandeep said, focus on getting your product done if you can. Maybe this person wants to see some progress before they put any money in.

For an angel, you have to make the case that the opportunity is worth the risk of their investment and that they are involved with something great. It can be an ego thing with angels since they usually made their money by working in a startup. So, cater to their ego a bit.

The legal stuff is secondary and in some cases, puts them off. Of course, they want a good deal and protection but the main thrill is finding the diamond in the rough that will give them 10-20x return on their money.

Tell him bluntly that you need to focus on your business. Ask him if he is interested in investing and when. If he is not or can't make a decision then you should move on - it is all sunk cost.