I did freelance consulting for years, and will undoubtedly do it again, because it's fun to see a small slice of many different companies. And it's not just sta

I did freelance consulting for years, and will undoubtedly do it again, because it's fun to see a small slice of many different companies. And it's not just startups who need custom software—many small businesses need it as well, and they rarely give up big chunks of equity to hire a CTO. Two major factors will affect how well outsourcing works for most people: 1) The quality of your programmer. It's an old cliché that the productivity of programmers varies by a factor of 10. You also need to take into account how good their code is, whether they write unit tests, what languages and platforms they use, and whether they're reliable business partners. If you're using open source tools, there's a shortcut to finding somebody good: Track down the project maintainers, and see if any of them run consulting businesses. 2) How well you understand your business. Some business people have a good grasp of what they need, and it's very easy for a good programmer to help them succeed. But my least favorite clients were always the ones who didn't understand their markets, who had dysfunctional committees, or who otherwise made it impossible for a programmer to earn them money. If you have $10K to spend and a good grasp of what you need, you absolutely can succeed by hiring a good hacker. (Assuming, of course, what you need is genuinely in the $10K range.) On the other hand, I've seen small businesses spend the better part of $1 million on a simple database application and still crash and burn. And finally, ask yourself what happens if don't quite achieve product / market fit, and you end up needing to pivot twice before you get traction. Nobody's going to lose too much sleep over a lousy code base if your business is successful. But can you afford two more iterations at $10K a pop?