"It's still prison. It's still not fun to be there," said Foster Winans.
Winans, a former Wall Street Journal columnist, served nine months in Danbury after being convicted of insider trading in 1985.
"I think it'll be terrible for her," he told CBS News Correspondent Anthony Mason.
"I thinks it's gonna be a crushing experience. When you're that powerful, that wealthy, that used to having your way in all things, one of the things you discover in prison is that you have absolutely no control over almost every aspect of your life."
The moment she reports to prison, Stewart will be strip searched, surrender her street clothes and put on a prison issue khaki jumpsuit.
Stewart won't be going to a penitentiary with barred doors. But she can say goodbye to her privacy in prison. She'll be living in a dorm room with at least a dozen other inmates. And forget all those jokes about "Martha, The Style Maven" redecorating her cell. Federal inmates aren't allowed to put anything on the walls.
"Convicts will get a kick outta this. My advice to Martha Stewart is keep your toilet clean," said Ray Hill, who hosts "The Prison Show" on KPFT in Houston.
"And there are no porters," he added. "They don't have people come in and do that for you Martha. You're going to have to do that for yourself."
Hill has personal experience. He was convicted of burglary in 1970.
"I spent four years, four months and 17 days in a Texas prison," he said. "And doing time in federal custody is the same thing, only the food is better."
Hill, who now advises convicts on what to expect behind bars, says whatever prison might be Sewart sent to, "The guards are gonna be very careful not to treat her favorably. So she's not gonna be a star anymore. She's gonna be a convict."
Minimum security prisons are essentially work camps. The only good news for Stewart: new inmates are usually given work duty in the kitchen.