Just jump right into it. If it fails then look and think what failed, then fix it and try again. Look how many space missions started up with explosions. We wouldn't be where we are if someone decide to stop trying after first failure.
The problem with this is that most startups don't have the runway to recover from a mistake. This is why you have to try things as early as possible - if you wait you won't have enough cash left to try something else.