Lou Pearlman, the mastermind behind 1990s household names the Backstreet Boys and 'N Sync, was sentenced Wednesday in Orlando to 25 years in federal prison for the decades-long defrauding of hundreds of investors and banks of nearly $300 through a complex scheme.

Lou Pearlman, born Louis Jay Pearlman in 1954 in Queens, NY, gave the world the Backstreet Boys and ‘N Sync in the 1990s. A decade before accomplishing such musical ventures, Pearlman had already embarked on a scam that would eventually lead to the bilking of nearly $300 million from banks and investors.

To add to the shock, many of Pearlman’s victims were in fact relatives and friends, as well as retirees in their 70s and 80s who lost their life savings. Senior U.S. District Judge G. Kendall Sharp said he had little sympathy for the disgraced entrepreneur.

Sharp nevertheless offered Pearlman a ray of light. For every $1 million he recovers, a month will be taken off his 25-year sentence. This means that if Pearlman can somehow come up with $300 million, he theoretically will not go to jail anymore. “I’m going to give you the keys to your jail cell,” Sharp commented, as quoted by Reuters.

Pearlman was sentenced the maximum Wednesday. In March, he pleaded guilty to two counts of conspiracy and single counts of money laundering and making a false claim in bankruptcy court.

As part of the plea deal, he also agreed to collaborate with prosecutors, FBI and IRS agents, banks etc, to track down his accomplices and as much of the money as possible.

Prosecutors presented at least 250 individual victims who lost a total of $200 million investing in two companies which only existed on paper - Transcontinental Airlines Travel Services Inc and Transcontinental Airlines Inc., and 10 financial institutions that lost $100 million.

Pearlman fled the country last year and was eventually found in Bali, Indonesia. He was living there under the name A. Incognito Johnson.

In court, Pearlman attempted to sound contrite – apparently not channeling alter ego A. Incognito Johnson, telling the judge he was “truly sorry” for what he had done to his victims. He said the past nine months had helped him understand “the harm that has been done.”

Sharp was not impressed and replied that the “sympathy factor” was parsimonious.

Court-appointed defense lawyer Fletcher Peacock said his client had always intended to pay back his victims. He also noted that approximately $103 million were returned over the years, but that the 53-year-old eventually lost his way around the intricacies of lawsuits against him, alleging fraud.

While his foray in the entertainment business was successful, the lawsuits apparently prevented him from returning the money.

Victims that testified said Pearlman had taken from the them the respite and safety they deserved in their old age. Many were forced to take a second job or live on modest Social Security payments.

Waneta Reynolds, of St. Petersburg Beach, made an emotional appeal, as she testified how her husband Roger was crushed by the scam. After investing, and losing, millions of dollars, he told his wife he had lost all his self confidence. He died seven months later, guilt-ridden that he had failed to provide for her, the woman said.

“My nerves are gone. My husband’s dead and I'm alone,” she said.

Pearlman’s clients in entertainment have also complained over financial issues.