NICK DOUGLAS — "Life is grand," says Jason Calacanis in his new profile on StumbleUpon, but he chose the saddest-looking headshot he could find. Maybe it's a hint that things aren't going as well as planned for the serial entrepreneur's latest startup, Mahalo. Another hint could be that Jason's first three links for StumbleUpon (a site where users share great web pages, sometimes causing a cascade of visitors to one site like the "Digg effect"). All his "great finds" link to pages on Mahalo — a pretty sorry way to drive traffic to one's own site. But I can't get over the mopey profile photo. As a friend said, "It's the idea of him posing to look sad — and that it probably took dozens of shots to get the right sad one."

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