Oprah became a millionaire 30 years ago, and her wealth has continued to increase into the billions since then.
Granted, reaching billionaire status doesn't stop others (Bill Gates, Warren Buffett, etc) from continuing to do whatever they can to earn more and more money, and yes, she's definitely earning something from WW. Have we figured out yet how much she's actually earning from her endorsement of WW? Given her long time financial status, I seriously doubt she's earning enough to warrant endorsing WW, just to continue on the weight loss roller coaster. I think she's just totally convinced that bread is the key to her dietary happiness, and WW gives her that bread. I think she truly does believe this is working for her and will continue to work for her for the rest of her life.
And it's possible that it may work for her, no matter how slowly she loses weight, or how difficult it is to maintain that loss. She has plenty of support all around her (a lot more than most WW members would have from weekly meetings) in order to stick to the diet, as long as she wants to stick to it. Not that her crew of support people wouldn't work the same way for her if she went on a normal, sustainable LC diet, but WW is so much more mainstream, more readily encouraged by doctors, nutritionists, and multiple versions of the USDA's food pyramid/plate.
It's so much easier to find a meal that fits WW when you go out to eat. How many restaurants have you gone to which proudly display the WW points for various items on their menu? And how many have you gone to that will even give you a clue how many carbs there are in the sauce they slather all over that perfectly LC steak? It's much more difficult to stay strictly LC when you eat out, but she's powerful enough, and rich enough that no matter where she goes, no matter what she chooses, her crew could always find out exactly what she's consumed in WW points for any given meal, and then set up portions for snacks and meals for the rest of the day/week for her. She doesn't need to do any of the work of counting points and figuring out what she still has left that she can eat the rest of the day/week, just eat what her chef gives her to eat.
The same could be done if she did a sustainable LC diet though - she has the support, and she has the money to stick to it with little effort. She just doesn't want to eat LC.
If I was in the position of choosing between continuing to accumulate more wealth than I could possibly spend in 5 lifetimes vs much more easily achieving and maintaining a healthy weight, I'm pretty sure no matter what fame and fortune I could achieve by going the WW route, I'd still be going for the much easier, much more sustainable LC route to a healthy weight.
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