To build his resume and career Charlie approached people he wanted to work for with work that he would complete for them for free. He advises the same approach with a step by step process in his talk and guide.
I think Charlie’s guts and proactivity are admirable. I often counsel people to try low risk, low commitment test experiences as they are trying to hone in on what type of career they would like to have. Charlie takes this concept a step farther by implying that once you know the type of work you would like spending time pursuing ‘free work’ can lead straight to a job.
I will note that Charlie’s work appears to mostly be for internet solopreneurs rather than established companies. His approach may be best suited for such a marketplace.
I’ll also note this quote from Seth Godin about Charlie’s perspective, which I found to be quite striking: “Isn’t it odd that we’re willing to spend $300,000 to buy an accredited but ultimately useless academic line on our resume, but we hesitate to do a month of hard work to create a chunk of experience that’s priceless?”