The reason I chose to bootstrap was because of my answer to a very simple question: What does success look like to me? May not seem clear how that helps, but just follow me for a few paragraphs.
For me, the epitome of success doesn't look like the CEO of a Fortune 500 company. I'm sure it's fantastic, but I don't think it's for me. To me, success comes in the form of being Time Rich and having the freedom of travel.
With that in mind... I now ask myself... Bootstrap or Venture Capital? Well... does Venture Capital align with how I want to live my life? Maybe you say.. of course! Once you sell the company for a billion dollars you can retire and do whatever the hell you want! Well... that is, if everything goes right, 3-5 years from now I'll maybe be able to live the life I want.
So.. what about bootstrapping? Can you really pay for a business to run? How can you possibly make enough to fit the lavish lifestyle of traveling?
The great thing about technology today is that there is so much SaaS products and other tools to help start your business for almost nothing at all. For general tools, you can click here, and for more internet startup specific tools check this page out on Product Hunt.
As for the lavish lifestyle, it's a myth you have to be rich to travel often. Case in point, How to travel to exotic, Expensive cities on $50 a day.
With a modest $3,000 monthly recurring income, ( which is only $36,000 salary, crazy low for a developer ), I can travel through most of the year working remotely.
And with the benefit of being a developer, I can build apps and SaaS products that can mostly run with little to no supervision, helping me free up my time to do whatever I like. Of course, if you're not a developer, automation tools can help on this side of things.
It's important to know where you want to go, how you want to live your life, so that you can make the right decisions that will help you get there. That's why I feel like "What does success look like to you?" is The Most Important Question to Ask before starting a business. That's why I'm bootstrapping this baby!