I’ve been on this treadmill before, and it’s not a lot of fun. It’s often suggested as a business model for open source or bootstrapped product development — the idea is that the product itself is free or low cost, but development is supported through consultancy support gigs. In truth, this barely works, because you no longer have the freedom to take the product where it needs to go in order to fulfill the larger need. Because the needs of each customer are so different, the product can easily lose focus, and because foundational development is rarely something clients see a need to pay for, the underlying platform can be neglected.
Of course, circumstances vary. There’s a chance I won’t find the right person straight away. In a founding team, it’s important that everybody brings something concrete to the table. That might be strong business or development skills; it might be deep domain knowledge; it might be extensive, trusted contacts. It can’t be nebulous qualities like “being very organized” or “getting shit done.” And they have to be in it for the right reasons: motivated by mission rather than solely by personal gain.
Ideally, I wouldn’t want to leave my job until I had a pretty good idea that what I was working on would be a viable business. I certainly wouldn’t leave my job until I had some kind of functional prototype: very few people will fund or buy into just an idea. An InVision mockup also doesn’t count: having to actually execute forces you to answer a different set of questions. I would also want to have enough personal runway — the length of time before the money runs out — to last for at least six months. A year would be better.