But here's the thing. Hiring is not an exact science. There are tons of variables in play beyond simple work experience and skill set. There's a whole art to negotiating employment (from the employee side) that most programmer types just don't get at all.
Engineers want everything to be a skills test. But in reality, skills come roughly 18th in a hiring situation, way behind questions like "did this candidate tell me any amusing anecdotes?", "was this candidate tall?", and "did this candidate say anything that inadvertently made me look bad?" Somewhere further down the list you might indeed find "did this candidate try to strike out on his own and fail?", but it'll be lost in the noise.
So if you want to work on something, work on your "being a guy that a CTO would want to have a beer with" skills. That, combined with a bit of networking, will often let you skip the "previous work experience" and "resume" portions of the hiring process entirely.