I was going to look for a job and got a lot of interviews through angel list.
It came down to one for me. I got flew out to san francisco and had a nice time for the founders. In the meantime while waiting for some references to get back to me. I actually finished the product and started getting customers.
In the end, the founders came to the conclusion I wasn't looking for a job, but more mentorship and I launched the product instead. Regardless of what happens, networking is your best asset.
If your own company is eminently practical, say less like twitter and more like ditch-digging then you should be able to bootstrap it eventually if there's a demand already out there. For a long shot where you have to monetize something secondarily to the product, I'd be less inclined to go into debt for example.
In my opinion, a spouse and especially children would be indicators against taking bigger risks in the form of debt. I also recommend against relying on a working spouse to support your effort for more than about a month - too much at risk.
Ask yourself how far have you come and where is the business headed? If it's consistent month-by-month and headed in the right direction that's certainly a big plus.