Jason Calacanis is running the risk of trying to do too much, too fast in his new exercise regime - jumping into what amounts to interval training almost immediately is likely to give him a bum knee or shin splints. Here's the thing, and I say this as someone who's been running/jogging since for over 30 years now: find a routine you can do consistently, and stick with it. Don't get obsessed over your daily weight, or over utter irrelevancies like the number of calories burned in a single workout. Get into a groove that you can stay with for the long haul - because your progress over the course of a month, or even a year, just doesn't mean that much.
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