Where my opinions differ:
> Asking questions in a meeting is one thing, but following up in an e-mail with an itemized list of; "how do you think about [x], what about [y] competitor, have you thought about [z]" is a surefire indicator that an investor's not willing to move right now
That's not true in my case, and also not true for many funds I sometimes share notes with (w/the founder's permission). I often see Q&A email exchanges that either the founder or an investor in a startup forwards to me. So I can see firsthand that other investors are asking email questions (and then making investments), too.
Furthermore, how much follow-up there is depends on check size. If someone is investing $15k or $50k as an angel, they might make a decision after a single meeting because that meeting is often their sole shot to meaningfully interact with a founder. But if a fund is writing a $400k or $1m check, more diligence will be required. My fund can't write a $1m check just because I really hit it off with someone. That would be extremely irresponsible financially. Similarly, a founder shouldn't take a $1m check from me (or any other investor) without doing some of their own due diligence.
> For every 1 in 100 founders you invest in this way, you passed on the other 99
Yes, but if most investors (esp. funds) want to do more diligence, and you have to go through more diligence to be the 1 in a 100, then avoiding investors who want to do more diligence means you might not end up anyone's 1 in a 100. A crude dating analogy: a typical person might need to go on a date with 100 people to find their life partner. But if you set a filter like "if you want a second date before deciding whether we should get married then you obviously don't like me that much," then you might end up filtering out most or all of your suitable partners.
> If you, as an investor, really wanted to invest in a founder and they snubbed you a bit after a follow up question (not rudely, they just have to choose where to focus), would you suddenly lose interest, or would you pursue a great deal / great opportunity?
It depends. If I already want to invest, then being snubbed would give me pause, but I would probably continue trying to make the investment work. If I wasn't sure I wanted to invest, then being snubbed would make it much less likely that I'd try to invest. Whether you're a founder or an investor, how someone treats you during the diligence/courtship process is a decent indicator of what working with them will be like after the investment. Working together might be worse than the preview, but in my experience it's very unlikely to be better.
> I have a hard time believing you'd let somebody you thought was the next Zuck walk out of the room without a term sheet.
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.
> I've seen friends put through the ringer by getting too caught up in the weeds with VCs that clearly weren't interested, or were tire-kicking. Can happen to amazing founders and it's wildly distracting.
100% agree here. This behavior really upsets me.
