Dear Jeremy: It sounds to me like this is the kind of idea that would require more in the way of brain sweat and time than money. I would just think of it as a part-time side job and go for it. However, make sure you have a clear understanding of exactly how much — if any — financial support would be required. Set these financial boundaries, and also be clear on when you expect the business to make money.
One thing I would warn against is ending up in a partnership if this thing becomes a success. Partnerships are bad news in the business world, so I'd advise you to figure out a way to structure things where you each own different parts — something more along the lines of a joint venture.
But in terms of doing some side deals, creating some cool new apps, and making money in the process? Absolutely, I would do that. Just figure out an intelligent way to structure the business and finances so you don't get pinched..
