So the question I have for existing & successful entrepreneurs is, how do you handle the migration from Wantrepreneur to Entrepreneur in terms of dealing with all aspects of running the business? Do you higher employee's/freelancers on a needed basis to cover the fields you lack the experience in? If thats the case, how do you financially support it when your just starting out(no sales). How do you just wing it and hope for the best on your weakest links of the chain and hope to learn from mistakes?
Do everything that you are capable of doing yourself, yourself. Hire whatever you can't. The goal should be to get the MVP (minimum viable product) operating as fast as possible.
Example: If your business is going to be a software of some kind, and you've never coded a day in your life, it'd be better to hire out some coders than to spend X amount of time and frustration to do it yourself, and have it end up being sub-par quality, or simply taking forever to get any sort of MVP off the ground. When it finally does get off the ground, what if you realize that no one wants this software in the first place, and you just wasted 2-3 years of your life trying to save money by doing it yourself?
That wasn't the best example. I guess what I'm getting at, is: Weigh the time value of how long you think it would take for you to learn X skill that you need. And if it significantly affects the timeline on the MVP, then outsource it.
Obviously, this takes money, so if you're going to outsource, then you need some.
And my 2cents is that if you want to travel and be location independent, I wouldn't want to run a service business. It's possible.... but there are other business models that fit your mold better (ecommerce/product businesses, software businesses).
Start with the goal: Location independence, and work backwards.