Holy crap. Who asked you? Certainly not the OP. Go crawl back under the rock you came from. Even if the OP is fat, he wasn't asking for your "help" with that. Life doesn't - certainly shouldn't - stop just because you're carrying more fat than someone on the internet thinks is the correct amount. If I listened to your type of bullshit, I would go hide in a hole rather than being an active mountain biker, skier, climber, etc.
Oh, and the quotes around "program"? That's classy as hell. There's a wide range of quality among crossfit programs, but again - OP didn't ask you what you thought of his approach to getting fitter and losing weight.
The OP asked. Pretty simply, when you put yourself out there on a public forum (albeit privately held); that's tantamount to asking for advice regarding skiing, which, sorry to say, is an athletic activity, which, sorry to say, can't be done if you're out of shape.
The internet doesn't think he's fat at 275 pounds and 5'11". Simple science does that for him.
If you want a "oh, that's okay that you're fat and you're out of shape, just buy some fat skis and have fun stopping 87 times on the side of that groomer because your legs can't keep up" you're not going to get it.
People need reality and tough love. Not a "oh that's okay you're fat and unhealthy, buy some fat skis that you'll never ski/never need and you'll feel better about yourself".
And the quotes around the "program" because I don't know what that means. I go to Crossfit classes and barbell club workouts about 7 times a week for strength, metabolic conditioning, and mobility/stretching. I didn't know what his "program" was, which is why I'm referring to that. (Also, when I was his size--actually a little under--I could NEVER do more than 4 times a week--simply because my body couldn't handle it.)
Hugs and kisses,