The point is, investors invest and thought leaders advise (and sometimes invest too). As an entrepreneur, you need both types of people involved in your startup, so it's natural to identify targets and phrase 'the ask'. From my experience, that approach doesn't work. But, I have found that the following approach works for both types of people.
Build a product, an MVP like I mentioned in my previous post, and get people using it. Once that happens, try to get face to face with your target. You should note that they probably won't take a meeting if they don't have a warm intro from someone they trust (ie someone that made them money). So, go to the events they go to. Politely introduced yourself, use your one-line pitch and show them your product. Then, here's the really important part, SHUT YOUR MOUTH AND OPEN YOUR EARS. If they aren't interested, they'll let you know. If they are interested, they'll start talking and that's a good thing. The most valuable commodity investors / advisors have is time. If you are getting it, make sure you don't fuck it up.
Investors are highly intelligent and have tons of experience. If they are interested their wheels start turning right away. They'll have suggestions and questions, make assumptions that may or may not be true, and they'll give you an opportunity to demonstrate to them that you are the person that can take an interesting idea and turn it into a big business. If all goes well and you jive, which is to say if they can believe they can convince their partners that you are investment worthy, they'll ask if you are raising money. It's their job to invest. They'll assume the reason you are talking to them is to raise money (b/c it is), so you don't have to ask.
Advisors are a little different, depending on their background / experience. When talking to them, approach them in the same way I mentioned above. If they are interested in you and / or your product, they'll come out and say, "What can I do to help?" At that point, you don't need to ask them to advise you, b/c they've already offered. FYI, you don't need to offer advisory equity to most people, especially if you haven't raised money / have a formal board. As a matter of fact, I'd caution you as to anyone who says they'll advise you if you give them X. Also, advisors are just that, so use them respectfully. Especially at first, limit your asks to things that can be solved over coffee, introductions, etc. After all, most advisors worth their salt are probably running their own companies / departments and advising multiple other startups, while trying to maintain some type of personal life.
Remember, you don't need to ask.
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