I've been there, and could stand to lose 50 or 60 pounds, so I'm going to be "straight", in this post at least.
* He's right in starting where he is, with something challenging. If a mile is what he can do in 20 or 25 minutes, it's a start.
* As a mile gets less difficult, he should increase both distance and speed. Keep increasing what he does.
* He needs to be safe. Pay attention to the weather, especially temperature and humidity. Heat is not a walker or runner's friend. If he's doing more than 20 or 30 minutes at a time he should take 16-24 ounces of water, or some sort of sports drink with electrolytes. If he's out in the sun he should wear sunscreen and a cap.
* He needs to be properly equipped. The big thing is good shoes, and he should buy 1/2 to 1 size larger, as his feet will expand. He should be ready to look into Dri-Fit type (it need not be Nike) T-shirts, compression socks to reduce the chance of blisters, and compression calf sleeves to reduce calf cramps and shin splints.
* He needs to have a "Plan B" for weather - hot, cold, or rainy. A mall, a gym, a community center - whatever is available and he can make work.
* Walking is good. He should also work on strengthening his leg, arm, back, abs, and chest muscles. Balance in what one does is important, and muscle strength and endurance will help with the walking.
* Come next spring he should look into walking/running in a 5K race. Schools do them for fundraisers. Charities do them. There may be local race organizers. Another possibly good timing would be to do a Thanksgiving turkey trot 5K or 10K next year.
Been there, done all that, though not running much yet. After doing a lot of walking for about 8 months I started with a turkey trot 5K in 2011. Over the past 12 months I've averaged completing a half marathon a month, walking, some of them on very challenging hilly courses. I see myself as having a long way to go; I sincerely wish Steve well in his effort.
And now, back to our regularly scheduled sarcasm and raillery!