Basically, you've described a Mastermind group. :) It need not be in-person, though. I have one, and we're scattered across the US. You definitely want to have somewhat similar timezones if you go remote, just because it's easier to schedule things. More than 3 hours time difference and someone is eating lunch when another is getting dinner ready, etc.
Gotta keep things simple to make them successful.
Re:Ask HN: single founders – how do you do it?
by andkon on Tuesday May 06, 2014 @02:13PM
(#7706155)
Thank you for putting a name to that! A search for 'Mastermind group' got me a few things to tweak for next time. Part of the focus of our group is geographical - we're all in Toronto, and Toronto startups have some specific problems because of the cultural (read: overly polite) landscape we're a part of, but I could see this working well over skype.
We get together once every two weeks and hold one another accountable. I bring donuts. Everyone shares a good thing and a bad thing that happened, explains what they accomplished and failed to accomplish, and commits to what they'll complete next time.
One thing: it helps to make sure everyone in the room is at a similar stage, or at very least working on product-focused startups (or all ecommerce, or whatever). That way there's a lot more value in hearing what other folks are going through.