Lots of founders are gearing up to raise a round in the next couple months. If that's you, here are some things to think about... (1/..)
Timing in the fall matters. The window is smaller than you'd think. Everyone comes back after labor day. There's lots of activity until Thanksgiving. There's a slower period between TG and about week 1-2 of December, where you *might* be able to close. After that, it's done.
That means you *need* to be ready to go, with investor meetings scheduled, by mid Sep latest. Hopefully earlier. It will always take longer than you think. You also want to compress your timeline and pitch as many investors as you can in parallel (eg venturehacks.com/articles/creat… …)
That creates a pseudo market for your shares, and makes everything easier. Pack those pitches in as short a time frame as you can. So be scheduling your first pitch meetings now, or very soon. How? ....
You need three main things to get in front of investors. 1) a lead list of targets, 2) a short list of 'Champions' who can connect you with them, and 3) a strong fundraising narrative to tell.
Let's talk about your Champions first. These people are critical to your fund raise. They're people who a) want to support you, b) know what they're talking about, and c) know investors you can pitch.
They're often other entrepreneurs, or advisors. If you've done a round already, they'll also be your existing investors. You need a few - I'd say 5-10.
Great Champions will support you emotionally, be helpfully critical of the pitch, brainstorm and sort leads, and when you're ready, connect you with investors with strong endorsements.
Now, investor leads: do the work to get a list of names for people to react to. Start here in spirit: brendanbaker.tumblr.com/post/422852061… (although the specifics are super outdated).
The number of targets will depend on the round. You should be able to come up with 100 names for an angel/pre-Seed round, maybe 50 for a Seed round, and at least 30 for a Series A.
Format it something like this. You start with the names. Let your Champions add any contacts they have at those firms (+ their names, because you'll be showing this to several), and add any notes. Quickly rank your investors - first choice through third. You'll use that later. 
As for a great pitch, that's a larger discussion. But above all, you're looking to communicate inevitability, urgency, progress, and a large opportunity. A great narrative isn't just box-ticking slides to include - it's an iterative process.
Before you pitch investors, practice with your Champions. An easy way to distill their feedback as a group is to ask each to note any exciting things, or hesitations, on a piece of paper as they listen to the pitch.
After a few practice pitches, you'll see patterns emerge. Lean into the exciting parts and give them good real estate in the story. Remove or rethink how to talk about anything that keeps causing hesitations. Iterate on the pitch.
At the same time, start schedule meetings (i.e. *soon* for first 2 weeks of Sept!). Quarterback this process. Direct your Champions to make introductions that make sense for you. Tell them when/how to help you specifically. Give them tools to work with (i.e. a blurb to forward)
I like to start with some 2nd choice investors first if possible, then the bulk of the 1st choice. Your pitch is going to suck at first, so these are almost practice pitches. If you get commitments, then great, it's a stronger pitch to your first choice investors.
As you're going out to pitch, know that it's a full time, emotionally-taxing job. It helps to get your cofounder or spouse ready to help/support in whatever way makes sense. Make sure your team knows you'll be focused 80%+ on that, and they need to step up.
You'll get a ton of rejections. It's hard to put a number, but as a rough guideline, if you're converting 10% of your pitches to commitments, you're doing ok. Although that depends on the stage, geo, etc. See here for an (old) example: slideshare.net/brendanbaker/a…
Most of those rejections aren't necessarily your fault. Many times it's just not an inherent match, but you don't know until you get to the table.
Fundraising is non-linear, and momentum-driven. Often you'll have me-too investors waiting to see who's interested. It'll seem like herding cats, without a lot of leverage. That's common. I don't have a good solution for forcing commitments, but ask your Champions what they'd do.
Ideally this is done by Thanksgiving. Do everything you can to avoid letting the process sprawl, but also know that sometimes it happens.
If you have the luxury of more interest in the round than available space, remember that you get to choose. Optimize for people you want to work with, who have solid reputations (reference check!), and can help the business in specific ways. It's ok to say no to investors.
If it's going well, congrats! If not, try to be easy on yourself. Know that all those fancy unicorns had (at least!) a round that was tough to get done. And know that many people have been through what you're going through. You're not alone.
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