Started making websites when I was 14. Sold first one in 2004 for $500, a game review site.
After that decided to get involved in online storage to fill a niche I spotted, sold my first storage site for $2500.. It was growing far too fast, I was 15 and didn't have the faintest clue how to scale it up. It was sold again 6 months later to a social network for mid-6 figs. Probs my biggest business mistake.
When I saw it sell again, saw the new social network basically fuck the site up. Had no non-compete, so started another online storage site and basically stole back all the customers who were getting disgruntled with the original site, as I knew exactly where they were coming from. Just outbid the guys on the traffic sources, and turned out they had let most of the contracts end anyway. (Idiotic, we're talking $300/mo for something in the region of xxK visitors a month.)
Started putting links back to my site in all the sharing links people used with files, and dominated all the search phrases based around file storage for a couple years, until the modern guys (Dropbox, Box, etc..) came on board, and the customer base & traffic sources I had started to shrink due to the decline of Myspace.
Had lost interest in online storage and wasn't really interested in investing into it to change the model and direction, although had plans to focus more on small business storage.. (Accountants, lawyers, etc.. looking to manage files between each other and also clients)
Website was sold last July for a fair sum:
Cloud Storage Company CX Raises $5M From Eric Schmidt And Others, Acquires FileDen | TechCrunch and got to have some conversations with some pretty awesome people.. Under NDA for the sale price though.
Article amuses me, CloudExperience had 500k members, we added 3 million to that count, lol.
Now I've strolled more into the content side, focussing on niches I have a passion in, building out a couple lists and building up a new online income stream. Alongside that I'm working on a business locally with my father, selling into independent restaurants, hotels, etc and small retailers.