I am an investor and my experience is, if you have done enough homework about the startup you want to meet, twenty minutes shall be long enough to clarify a few key things so you can make an informed decision.
I personally like asking a lot of questions, so I'd still prefer >20 minutes. I 100% agree with you though that preparation can save a lot of meeting time. One catch with YC companies in my experience is that they rarely have detailed pitch decks or significant web presences, so there's often not that much to research before a meeting.
Did you check out The Macro - http://themacro.com/ ? Yes the info disclosed by YC for each startup is still limited but better than nothing in the before.
Definitely helpful, but AFAIK only about a dozen startups from the 100+ startup batch have been covered so far (https://www.google.com/#q=%22meet+the+batch+s16%22+inurl:the...). I can imagine the coverage will double or triple by demo day, but I'm skeptical that all startups will be covered. Btw, I love the /data subsection of your website!
I typically do 1-hour meetings and that works pretty well. 45 min would be okay. I haven't tried 20 min before, but that feels a little short. To apply the over-applied analogy that fundraising is like dating, 20 minutes would be enough time to tell if a date is terrible, but I'm not sure if it's enough time to distinguish between a B date and an A date.
Two ideas related to Investor Day that I'd be interested in:
- let investors ask for one or two consecutive 20-minute slots. Founders can just allocate one slot to someone asking for two, but asking for two slots would be a good signal of investor interest and/or investing style.
- don't automate scheduling, but instead host all founders at a single location for a few days, and make it easy for investors to book slots on founders' calendars once those founders opt-in to meeting up. Maybe this could use something like https://calendly.com/
Roughly speaking, our investing process is: 1 hour one-on-one meeting, then 1 hour full partner meeting, then decision.
The way I think about the math:
Current scenario: 25 1-hour one-on-one meetings -> 10 full-partner meetings -> 2-3 investments.
Worst case for Investor day: 25 20-minute meetings -> still don't have enough info -> 25 1-hour one-on-one meetings -> 10 full partner meetings -> 2-3 investments.
Good case for Investor day: 25 20-minute meetings -> 10 companies don't seem like a fit -> 15 1-hour one-on-one meetings -> 10 full partner meetings -> 2-3 investments.
Best case for Investor day: 25 20-minute meetings -> I get all the info I need -> 10 full partner meetings -> 2-3 investments.
These four cases represent 25, ~33, ~23, and ~8 hours of one-on-one meeting time, respectively.
This is probably sufficient for many angel investors, a few seed investors, and very few series A investors. No matter how much homework you've done on a company you can't responsibly deploy $5M after 20 minutes of diligence on the team.