If I'm not convinced to invest after one meeting, I usually don't invest. On the other hand, if I'm convinced after five minutes, I'm usually asking where to send the wire by the end of the meeting.
Armory is a good example of an open source/open core company I did invest in. They had me convinced in just a few minutes. They had an answer for every one of my objections and made me feel like I'd be missing out if I didn't invest. And so far they're doing really well and it's one of my best investments to date.
And if you're selling a product, make sure you know your competitors well because a lot of objections will be in the form of "but competitor X does this, how do you solve that problem?" and "what do you do that X doesn't do?". So you better know X really well because the person you're talking to already does and will know if you're making stuff up.
As cynical and hollow as it sounds, pretty sure this advice is consistent with what I have heard in multiple videos and blogs from YC.
See also: "create investor fomo", https://html.duckduckgo.com/html/search?q=create%20fomo%20in...
Ultimately you care about the latter and you don't always need the former to get there.
And I’d modify one thing you said: I believe the #1 most important skill for a startup CEO to master is storytelling —- which is critical for selling, fundraising and recruiting. https://www.founderculture.net/c/new-noteworthy/the-1-must-m...