Ryan Stewart writes about managing risk in your online business endeavors over at Shoe Money. Stewart recently purchased ad space from JohnChow.com and flipped it for a profit. He then used the publicity to sell a site he hadn’t done much with for much more than he expected. It’s a good article on how to take calculated risks.

So if you’re complaining about not making enough money online, stop complaining and start thinking about how you can take more risk. Write down the pros and cons of the situation and weight the results of success against the consequences of failure. In most cases, failure will teach you enough to make the risk worthwhile anyway. If my ad had gone 2 weeks without a bite, don’t you think I would’ve done everything in my power to convert the traffic? Definitely.

Don’t be stupid with risk, but don’t be a sissy either. If doing it doesn’t make you a little sick to your stomach, then it wasn’t risky enough.

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