How am I?
Along the road, I tried to succeed with some "start-ups"... all failed. I picked up my first freelancing job... and didn't get paid. My first job interviews were horrible: I didn't have a clue about professional programming and sucked at technical interviews.
But at some point thanks to my "start-up" projects I had kind of a nice portfolio and gained something you might call "experience".
Since then I didn't have any problems finding new job opportunities. Now I'm working as a contractor. I often can pick from multiple offers. Most importantly I have the luxury and freedom to take several months of vacation each year.
As a contractor, I switch my jobs regularly and have been through lots of interviews. At the same time, I was often part of the hiring process inside the companies that I was working for. I've been on both sides of the table.
I hope I can make your path a bit easier by sharing the experience and insights I gained.