I made close to 50k selling Everquest items/money/accounts on Ebay between 7th and 8th grade. It began when I got mono in 7th grade and was stuck at home for 3 months (milking it). I took the EQ money, invested it in Nike and Chevron (reinvesting dividends) and pretty much forgot about it through high school (except for a car down payment) and into college. After my first year in college I was starving to death, but was afraid to squander that EQ money that had been growing really well. That's when I made friends with an eccentric math genius jew who turned me onto day trading. I got super interested in the markets, sometimes to the detriment of my college studies. In 2008 I recognized the coming crisis, and sold before the major crash. That same year I bought back in at the bottom called by CNBC's Mark Hanes, RIP. I still miss hearing him in the mornings. Anyways, by the time I graduated from college the markets had rebounded and my money had grown substantially. FOE was my biggest winner, with my average return being over 300%. Scared and astonished by the opportunity presented to me, I sold about half of my holdings to have a strong cash safety net. After graduation I used some of the money to start a few different small businesses, two of which failed and one of which sold for enough money to cover the losses of the other two and even generate some profits. Since college I've studied the markets and trading strategies fervently. Now I trade options almost exclusively. Most my trades last less than a day, as I try not to let any option contracts ride overnight. Of course, sometimes there are exceptions.
I'm not rich, but I pay myself around 4k a month. Sometimes, I lose money and pay myself less or bonus myself after a good month. I focus on maintaining a large cash reserve for trading that I can also use for travelling, etc. My lifestyle is pretty awesome since I can work from anywhere, as much or as little as necessary. Last year I maxed out my european tourist visa, which was fun.
I wouldn't recommend it to everyone. I'm one anxious fuck and consider what I do 1 degree north of gambling. The lows are really painful and the highs require extreme discipline to quell the anxiety brought on by tough, important decisions. I walk a chemical tight rope, balanced by caffeine and THC. It's not a lifestyle for the cautious or fearful, but to me it's pretty damn fun.
I'm approaching 30 and am beginning to seek a more stable lifestyle, i.e. real job, etc. But the trade-off between freedom and stability is a tough one to balance...