I want to start a web design company, and ultimately a brand name. I am hoping to acquire skills, financing, and contacts simultaneously. Is this possible? Can one generate enough money with freelance work and basic skills to sustain itself (and me for a while) and grow? I was thinking about starting a blog to document my experience. Is that marketable? I welcome any advice and direction!
10-15 years ago, a lot of people with little or no experience set themselves up as a "web design company" and made a living from it. Nowadays, I suspect it'd be much harder as unless you are doing the top-end jobs, there is much less money in it.
It isn't impossible, but I think it'd be difficult to do now, unless you were very lucky in finding some high-profile jobs that nobody else knew about.
It can be done, but you've got a lot to learn. I build some sites on the side ($300-$5000 projects), and I was self taught. Still, I find there are lots of people out there who know way more than I do. If you're serious about this, learn WordPress. With little more than a good understanding of html and css, and a basic understanding of php, you can build template websites (WordPress has tens of thousands of themes) for people and reasonably charge $20-$30 an hour. I've gotten to the point where I can install and create a basic WordPress site with 3-5 pages in less than an hour. Just a warning though, doing these small $100-$300 sites sucks. Understand it will take you 2-3 times as long as it should.