1. Having dev skills
2. Building a mobile app or WP plugin (i.e., something simple) vs. a SaaS app (i.e. tons of moving parts and more ongoing maintenance)
3. Experience outsourcing in the past. It is absolutely a learned skill and the more you do it the better you get.
If you have none of the things Ruben and I have listed (so you're not a dev, you're building a SaaS or other complex app, it's your first time outsourcing, etc...) you have a very, very low chance of succeeding. And if you have every single one you're on the opposite end - IMO the swing could literally be from 10% chance to 90% chance of success depending on the factors you have in place.
So, if you're new to development, it's probably best to build small products (wp plugins, niche sites etc.) to build your portfolio, earn a little cash and more importantly increase your knowledge and experience. Amy, I'm not sure you would agree with this but I'd love to hear your views.
Aside: Rob, you mentioned that outsourcing is a continuum and something that needs to be learned. Is it possible that some people just get lucky with a great outsourced developer? For example, you've said on various podcasts that you're an advocate of VAs but have you had more than 1 or 2? Presumably, as soon as one works, you stick with him/her - perhaps that's luck rather than learning?
Yes, this is the tact I would take. I talked about this exact topic in-depth on a recent episode of Foolish Adventure: http://foolishadventure.com/audio/how-to-market-your-softwar...
Early successes are huge not only for you learning the ropes of outsourcing/marketing and giving yourself a small financial cushion, but also for building your confidence that you can make this happen.
>>Rob, is it possible that some people just get lucky with a great outsourced developer?
Good point. This is definitely possible. In my list of the 3 factors above I should have added a 4th: You find an awesome developer, whether through luck, having a great network, or knowing how to hire.
But it's just another variable that impacts that continuum I mentioned and pushes you more towards that 90% or 10% end.
>>For example, you've said on various podcasts that you're an advocate of VAs but have you had more than 1 or 2? Presumably, as soon as one works, you stick with him/her - perhaps that's luck rather than learning?
My success rate at hiring and managing VAs, developers, designers, writers, etc... is waaay better than it was when I started (at least 2x better, maybe 3x). I attribute this to getting better at both hiring (i.e., choosing the right fit) and managing/delegating (i.e. having more skill with outsourcing).
Oh, of course I agree. One of the things I harp on over & over is the idea of stacking the bricks:
http://unicornfree.com/2012/9-years-ago-37signals-had-no-pro...
The whole concept says "Don't try to build a SaaS the first time. Build something small. Don't try to build a huge business the first time. Focus on selling SOMETHING." etc. :)
One more q: Were these single people with limited budgets, or companies?
These are the ones that were successful at it...many more were not. But I don't know if the ratio is the same for people with/without dev experience (plus sample size is too small).
What I do know is that most:
1. Got help picking a developer initially
2. Had some guidelines on how to work with a developer
3. Had no development experience
4. Had to get learn how to outsource and made some mistakes (but eventually made it work)
Outsourcing is tough at first but it gets easier. Like any skill, you have to get better at it.
In any case, I do think it's a great idea to learn how to program so you're not so helpless if/when problems come up.