One large problem for a lot of entrepreneurs, regardless of whether it's their first startup or their eighth, is motivation. We slowly become less motivated due to delays, or thinking about how long things are taking, and whether it's worth it to continue pursuing the idea.
One solution to remedying this valley is getting entrepreneurs together, talking about their work, and having them work on their separate startups, but together. We have Jellys, we have DevHouses, but this needs to happen more often. Events like these offer a connection back into reality and a community to associate with, and for the most part, motivates entrepreneurs to journey on.
How do we make events like these happen more often?
I know some entrepreneurs who get together once a month to commisurate in person. That alone can go a long way.
See everything Howard Mann has every written, but in particular his little (free) book.
Making events happen more often is, IMHO, a local and specific thing, rather than a movement or general strategy. Surely you can find some folks in your local area. Totally agree it's a good idea, and I feel your pain on the burn-out (which you can't share with your employees of course).
I help put on an conference every year for MicroISVs. Nothing beats networking with hundreds of fellow software developers, web designers, internet marketers, and service providers. This will be the 20th annual Software Industry Conference. It has 3 days of interactive sessions, networking events, and exhibits by e-commerce providers. This year the conference will be held in Dallas, TX July 15-17 (Thur - Sat). Conference details are available here and the conference schedule is available here. Events include an Exhibit Night where you can test drive the latest in e-commerce, software protection, SaaS, and more. There is also a Gala Networking Dinner that wll bring together experts with decades of experience.