Agreed! You'll never get anywhere without taking some sort of risk or making a bold move.
However, you should do as much homework as possible and not go into something blind - so I also agree that you should be taking calculated risks. At least if you fail, you will know that you did everything in your power to calculate your investment.
Be extremely persistent. This is the most important quality I can stress, in any sort of business. Keep looking for deals and continue in trying to innovate the industry. As long as you're persistent enough, your gem will come calling. It's very frustrating at first to see some people on here making these big deals when you first get in the game, but that could easily be an newbie out there with some time, effort, and a little luck !
I also agree with putting all your initial capital in a .com with traffic/revenue and start from there. Keep your day job and throw in your extra savings towards traffic/rev names and watch your earnings grow, month after month.
Get creative with how you monetize your names - try all the parking providers - the difference can be HUGE. Don't be afraid to try out some affiliate programs out there. Parking Empire offers some great deals from the looks of it and I'm getting excited to try out (btw, no affiliation with them at all) Affiliate commissions will likely dwarf your parking earnings, even with a fraction of the clicks/traffic.
Let's keep this thread going