Financing: the next step question?

You have a great coffee meeting with an investor but it isn’t quite a pitch.  How do you phrase the ask? Or will they ask if they are interested? How do you frame this so as not to sound desperate, but strongly enough to show you’re pushy enough to sell?  Silicon Valley insider stuff here, think experienced angels and vcs. Lots of angel friends who’ve met me for coffee but haven’t stepped up yet, so I wonder if I’m going about this wrong.  I was told if you want money, ask for advice, but now I wonder if that’s too passive.

  • have them compete. get one interested and use that to herd others. as for approach, how do you ask a girl out (assuming you are a dude) without showing too desperate?

  • I’ve found with angels a lot of it has to do with how much they like you and how highly they think of you. I’ve had cases where investors have offered to invest right after I asked them for advice even though I never brought up the subject of an investment.

    The classic way to broach the subject is to ask them if they think your company is ready for investment. Or what you should do to go about fundraising. That way it lets them know you’re looking without putting them on the spot.

  • (I’m a VC.)

    After giving your pitch, ask for feedback. If the feedback is negative or there’s a lot of (constructive) criticism, thank the investor and go home to think about whether the feedback is valid and how you can incorporate it into your product and pitch. If the feedback is mostly positive, you can say something like, “I’m starting to fundraise, and I’m not sure if this investment fits your focus. If it does, and this is something you’re interested in, I’d love to know what a good next step would be.” If the investor doesn’t like it, they’ll probably say “sorry, this isn’t the kind of thing I invest in.” If they like your pitch, they’ll tell you the next step.

    Actually, you can ask anyone for next steps. Even if someone doesn’t love your pitch, they might give you a concrete next step, like “let’s talk again when you have 5 pilot customers” or “let’s talk when you have a lead investor.”

  • OP here: let’s just say I don’t have a lot of experience asking women out. 😉

    VC, many thanks for your insights. I like this approach a lot–fits with my personality. I like the idea of leaving a polite “out” for the investor that preserves the relationships. So much of what we do in our networks is “not now;” so it’s important to keep those connections going in the most respectful way. Really appreciate it. I have been given signals like “call me when you have x customers” and that’s totally fine. As a first time founder I expect to be proving myself a bit, even to people who know me, because when it comes to money, the stakes are higher.

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