I wish him luck, but wow, his track record on the subject is just so poor that I don't know why he expects this time to be different.
On the surface of it, his approach makes logical sense to me: Set a goal weight and a completion date. Divide by time to figure out what you need to lose each week. Figure out how many calories equal a pound. Keep track of estimated calories burned and calories consumed. Ensure that the difference between calories burned and calories consumed for the week is greater than the equivalent amount that you want to lose. And then just stick to the plan...
BUT, I recognize that it's not that simple. Just figuring out the numbers like that is the engineer's approach, and the human body doesn't behave like a machine, computer, or standard process. Going to the extreme ends (which Adam is wont to do) tricks the body into thinking it's starving and has the opposite effect. And for reasons that I don't understand but I'm sure someone with a medical or nutritional background could explain, it's easier to lose the first few pounds than it is the last few, so assuming an even amount of weight loss each week just doesn't seem realistic.
Again, on the surface, 2 pounds per week doesn't sound too terribly unreasonable... but when he said he wanted to drop from 260 to 200 in total, that seems like a lot -- it's nearly 25% of his body weight. I don't want to crap on his plan because no one knows less about weight loss than me, but the DIY approach he's taking just seems haphazard. With as much as he brags about how well he's doing financially, I feel like he'd be better off consulting with a nutritionist or someone with professional expertise in the area if he wants to see real results that are different from his past efforts.
And this is what we're dealing with.
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Oh, for goodness sake!
He also did not know that the YOUGURT parfait contains yogurt! He under values the calories again! 
