Well, I can use myself as an example of something that works as i was in similar shape.
Basically the plan is to create many small meals that are healthy and spread them out throughout the day. This will help avoid hunger and over eating as a result, while helping getting used to eating smaller meals and keeping the metabolism running.
1. Find out his calorie budget for normal activity and make meal plans that are around 75% of normal budget.
2. Make a meal plan that meets the normal calorie budget. Eat this meal plan every 3rd day with low days in between. This will help the body keep from entering a conservative calorie mode.
3. Don't cheat
As far as exercise goes, he's probably not in great shape but will gain strength quickly. Starting out just do some cardio with 20 minutes at his target rate. As he progresses in endurance raise it to 40 minutes or so. I would suggest not overworking the cardio. If you acheive lots of endurance quickly, you're body will be more efficient at exercising.
I did a lot of elyptical(sp?) machine work starting out because jogging was so stressful and hard to keep at a steady pace for long enough to burn the needed calories. I also started hitting the weights, doing whole body workouts.
Anyways, i'm by no means an authority on weight loss but i am a good success story
