Ben and Jerry are two hippies in Vermont who some years ago started a successful homemade ice cream business.
One of their most popular flavors is "Cherry Garcia"

Selling out commercially means that you gave your soul and integrity for money, making money wisely is not "selling out" it's intelligent.
Advertising in a magazine isn't "the" example of selling out commercially. Many years ago, I used to be an illustrator, I'd done renderings for magazines, all of which I was paid for. The period when I sold out was when I did jobs I hated for money.
Now I make money playing music, which I love, I play only music that I want to play, that's intelligent. The health-food person we're referring to sounds intelligent, doing something worthwhile that provides for her. Anyone can sit in the street and earn nothing.
As for the Grateful Dead and selling out, yeah, they were "artists" at the beginning, but then they became a corporation as any other commercial venture. Read Phil Lesh's auto-biography, he'll fill you in.

Re: "cutting hair, wearing suits..."
How one wears their hair and clothes means nothing beneath the skin, I know more deeper, spiritually based people who work at careers and have suits and short hair, and I know more phony people with dirty feet, smoke pot, and drench themselves in pachuli, and visa-versa.