Then he pulled an Oprah on his audience. In doing so, he became guru to a budding movement of "fatbloggers."
Calacanis, 36, decided that he was fed up with being overweight. A svelte 165 pounds a decade ago, he recently tipped the scales at 207 after spending day and night at his desk working to sell his company, Weblogs Inc.
After shedding the venture in a $30-million sale to AOL, Calacanis felt it also was time to say goodbye to the extra pounds that had gathered around his middle and made his boyish face look cherubic. He hauled a treadmill into his Brentwood home and vowed to slim down to 180 by summer.
But he wasn't doing it alone. As Oprah Winfrey has done on her show, Calacanis enlisted the help of his audience. He promised to post his weight -- whether it's up or down -- on calacanis.com every day.
Call it Weight Watchers for the blog set, with a dash of public humiliation for incentive.
"Support is always a good thing," he said recently.
When readers chimed in with dozens of supportive comments, he realized he had tapped into something special. After all, he wasn't the only tech geek struggling to lose weight. He began recruiting other techies to join.
"Fatbloggers unite!" he titled his next post.
Join they did. Dozens of other pudgy bloggers now write about their weight, caloric intake, exercise regimens and dieting mishaps.
"It's one part support group, one part catharsis, one part education," said Joseph Jaffe, who's lost nearly 30 pounds since he too began chronicling his efforts on his online marketing blog. "It's also a masochistic exercise. Every Friday, I log my weight. If I fail, I look like an idiot. It's highly motivating.'
There was the expected backlash from readers who valued Calacanis' thoughts on the Internet business landscape but couldn't care less how much he weighed. One called his posts "fatspam." Another pleaded for him to write about something else. Others pilloried his efforts with mock videos and websites.
"You start to build an audience, then the audience starts demanding stuff from you," Calacanis said. "That's the double-edged sword."
But something in the posts struck a nerve among the desk jockeys who read his blog. He says traffic to his site has gone up since he started fatblogging. And he has helped set the standard, devising ground rules for how to fatblog properly and urging others to chronicle their own weight-loss efforts.
"Format: One blog post a day with your weight as the title," he wrote one day. "You can also add to the post what you're doing in terms food consumption, exercise, and what's working for you -- however, the base line for involvement is three numerical characters a day in the subject line of a post."
Bill Reals, a marketing manager for a San Diego software company, heeded the call.
"Most people who work in technology have a weight problem," Reals said. "We sit at our desk for hours, work late and snack on junk food. It's a very sedentary lifestyle."
Adding pounds to the problem, many technology companies have coffee stations piled with free food. Managers put it there to motivate workers and keep them energized without having to stray far from their workstations, but it's not always low-calorie fare.
"We have a cupboard that's stocked with chips and candy," Reals said. During crunch time, when employees hunker down to meet deadlines, "we all end up gaining 20 pounds, easy. This year, instead of diving into the free food, I blog."