Bernie Madoff once had the best that money could buy when it came to his many homes. For his latest accommodations, he sought out a different kind of broker: a type of prison consultant increasingly popular among white-collar wrongdoers.

Madoff, now serving a 150-year sentence at the Butner Federal Correctional Complex near Raleigh, N.C., isn’t the only high-profile individual to seek out a specialist to help prepare for life behind bars.