A Florida executive whose family business once owned Playgirl magazine has pleaded guilty to conspiracy to commit securities fraud for misleading investors in another of his companies — one that made high-interest loans to small businesses.

Carl R. Ruderman, 82, was chairman and chief executive officer of 1 Global Capital LLC, a commercial lending company that filed for bankruptcy in July 2018. Federal authorities said he took part in a $250 million scheme that affected more than 3,400 investors in 42 states.

Ruderman pleaded guilty Thursday in federal court in Miami. Court records show sentencing is set for Jan. 3, and he faces up to five years in prison and forfeiture of more than $250 million.