> FWIW, my fund has made ~65 investments in the last 5+ years. Exactly one of those investment offers was made during the first meeting while the founder was in the room. The majority of investments took 2-4 meetings, a few email questions between meetings, and several reference calls. From what I know, most funds that write $250k+ checks work in a similar manner.

Sure: but let's dig in. I'm interested. Out of those 65 investments, how many did you explicitly lead? Sure: the majority took 2-4 meetings. But...

(1) What's a meeting to you? Keep in mind that your Principals and / or Associates conducting meetings and diligence should not qualify as meetings. If it's not with a GP it's not really a fundraising meeting and no founder should reasonably consider it such. Yes, I'm adding a semantic layer here, but this semantic layer is extremely important to founder psychology and how we classify meetings, fundraising success and more.

(2) How many of these investments had a term sheet after only one meeting? Not necessarily with the founder in the room, but this is, for all intents and purposes, functionally equivalent to an investment offer made in the room?

On top of that, is the a correlation between leading an investment round and a fewer number of meetings with a founding team before investing? My intuition based on my own experience and anecdotes of other founders would be that there should be a correlation - happy to be wrong, though.

Also, out of the investments that took "2-4 meetings", did the founders ever roadblock you from investing (i.e. it's a meeting but the founder "isn't fundraising"?) - because this is pretty common (some use it as a tactic but often it's just flat out true), in which case "2-4 meetings" isn't actually "2-4 fundraising meetings." If a founder is at this stage, they don't need this Medium Article's advice: they've already developed the maturity to execute upon a fundraising strategy, you just might not see it due to selection and / or survivorship bias (seems natural, and just how things are done). In fact, they're executing the latter part of the strategy outlined here (have found a lead via "focus", or relatively confident in their ability to receive a term sheet when they pull the fundraising trigger).

We're really pulling apart the fabric at the seams here: there's a reason this article isn't a hundred pages or more, which is realistically the volume of information a founder has to internalize while they're developing their own understanding of the fundraising and investment landscape. They'll also find their experience to be very personal. This advice is meant as a launchpad, and I think it's a good starting point for novice founders.

If I were to give advice to new founders (and I do get asked occasionally, but I'm literally nowhere close to a celebrity fundraiser and still a fledgling entrepreneur) it's, "I still don't understand fundraising. Just be yourself and build something you're passionate about, have confidence, be persistent, be kind, and the right people will come along. You'll probably trick yourself into thinking you understand something about the process, but realistically, fundraising is just about people and relationships, and shit is messy. Be humble and thankful, and try not to waste too much time discussing fundraising strategy with investors on Hacker News."

Disclaimer: I often don't follow my own advice.