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.
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/
If our original scenario is:
Scenario 0: 25 1-hour meetings over the course of a few days. Investments = 25-n
You seemed to be suggesting in an earlier comment you might end up with:
Scenario 1: 25 20-minute meetings followed by 25 1-hour meetings. Investments = 25-n
I think you'll actually end up with:
Scenario 2: 25 20-minute meetings, eliminate x companies, (25-x) 1-hour meetings. Investments = (25-x)-n.
Saves you and the founders some unnecessary hour long meetings.
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.
40-min meetings might be a little awkward because usually the first 5-10 minutes of a meeting are social / chit-chat, so it might feel a little weird to immediately start a 2nd meeting exactly where you left off on the first meeting. Also, most of the time a 40-min meeting still takes up a full 1-hr time-slot since most people schedule meetings on the hour.
This is the homework we do:
https://www.zillionize.com/data/
>>do you feel like you can complete that homework prior to demo day
Yes the time is very tight so we have built an app to automate that.