Sarasota's self-proclaimed 'Annuity King' sentenced to 15 years in federal prison

Diane Wasserman stood before U.S. District Judge Charlene Edwards Honeywell on Wednesday evening, asking in a shaking voice to allow her husband to remain out on bond pending an appeal.

Sitting behind her at the defendant's table in the marble and dark-wood chamber, Phillip Wasserman leaned back in his chair. He already knew his fate was incarceration. Now, he waited to find out how long.

Wasserman's wife told Honeywell she'd known her husband for 44 years and that they had an amazing family, adding that he wasn't a flight risk. As she walked away from the stand, she wiped away a tear.

The self-proclaimed "Annuity King" of Sarasota, Wasserman was sentenced to 15 years of incarceration followed by three years supervised release after he was found guilty in May 2023 on multiple counts of wire fraud and mail fraud, as well as conspiracy to commit wire and mail fraud.

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Wasserman, a former lawyer and licensed insurance agent, was indicted in June 2020 by a federal grand jury for running a "fraudulent insurance venture" called FastLife that included Ponzi-style payments from elderly, retired investors that funded his lavish lifestyle, including a beach house on Casey Key, Tampa Bay Lightning season tickets, jet skis, and luxury cars.

Wasserman operated investment businesses, including Phillip Roy Financial Consultants and Phillip Roy Financial Services, in the Sarasota area for years before FastLife and billed himself as the "Annuity King" in promotional materials. He organized investment seminars attended by thousands of seniors in Florida.

"It isn't my intent to impose a death sentence in this case," Honeywell said following her sentencing decision.

As part of his sentence, the 67-year-old must also pay approximately $6.8 million in restitution, including more than $5.9 million to victim-investors and more than $903,000 to the Internal Revenue Service. Honeywell also entered a forfeiture of approximately $6.3 million as a penalty meant to further punish. Wasserman also effectively lost his license to be able to market insurance, thus rendering him without a job.

While Honeywell denied Wasserman's request to remain on bond pending appeal, he was not immediately taken into custody Wednesday. The judge granted Wasserman's request for voluntary surrender, and he must report to the U.S. Middle District Court in Tampa on Feb. 23 before 2 p.m. at which time he will be taken to either the Coleman or Montgomery penitentiary.

Standing outside the Tampa courthouse, Wasserman said that there was no fraud and that his case was because of political persecution. It's a sentiment he's stood by, as well as his continued claim of innocence, following Honeywell's decision about incarceration. He indicated in an email he plans to appeal.

While Wasserman said during the hearing that he understood investors' anger towards him, he blamed the government for stoking the anger by not allowing him to make payments to investors as the case progressed. Wasserman is adamant no crime occurred with FastLife and that it would have been a profitable business had the government not interfered.

Wasserman sought to be sentenced to probation with a plan to pay restitution to investors, and during the hearing, he presented several witnesses who explained that Wasserman was doing affinity marketing work and that the money he earned would go to pay restitution. Wasserman estimated he could pay back all the investors within 12 years.

A sentencing hearing was initially scheduled for Aug. 17; however, the hearing was postponed until Jan. 12, only to be extended again to conclude on Jan. 31.

Father and daughter who invested in FastLife speak out

Ivan D'Souza believed in the American dream before he came to the U.S. in 2011. He moved into The Villages with his wife, ready to enjoy retirement with the funds set aside during all the years he'd worked.

“He was the kind of man that wanted to give me and my sister everything, but teach us the value of hard work,” Laine D'Souza described her father.

Wasserman's fraudulent scheme would wipe out more than $600K from both him and his now 48-year-old daughter.

It started with Ken Rossman, a Florida certified public accountant and licensed insurance agent, who worked on Ivan D'Souza's taxes and soon befriended the retiree, coming by the D'Souza residence for lunch and speaking about his own life, Laine D'Souza said.

In January 2014, Wasserman and Rossman held an annuities seminar which included a free lunch at the exclusive Arnold Palmer Country Club. Rossman convinced Ivan D'Souza to invest in Wasserman's insurance venture, FastLife, which he said aimed to help retirees with medical coverage.

Since Ivan D'Souza moved to the U.S. for his retirement, he didn't have access to medical insurance coverage and the insurance venture seemed like a good investment.

Ivan D'Souza then helped his daughter to also invest in the company, convinced by Rossman that the two would see a 12% return on their investment.

When the D'Souzas started asking for the interest owed, Rossman and Wasserman didn't come through. Instead, Laine D'Souza said the two attempted to evade her, offering to buy lunch or ads on Facebook and making excuses.

Then the Florida Office of Financial Regulation wrote to everyone in 2019 to say they were looking into the financial aspects of FastLife and saw that something wasn’t quite right.

Wasserman and Rossman reached out to investors to reassure them that this was the normal procedure because it was a new business and told their investors not to worry about the regulator’s letter, Ivan D’Souza said.

Later, IRS agents and the Attorney General’s Office started contacting investors, but for the D’Souzas, it was too late to recover their money.

Wasserman and Rossman were arrested in June 2020, and a federal grand jury indicted the two on multiple counts. The 18-page document claimed FastLife convinced elderly investors to liquidate traditional investments, and to borrow funds against their life insurance policies, to generate cash to put into the new business. However, Wasserman hadn't told investors about surrender fees and other costs associated with the liquidations.

'Protect the seniors of Florida'

Mickey and Thomas Bohan first met Wasserman 21 years ago when he was working under his other company, Phillip Roy Financials, and invested thousands with him, according to Mickey Bohan's testimony during the Jan. 12 sentencing hearing.

As Mickey Bohan testified behind the solid wooden podium before the judge, her husband, a legally blind veteran, sat to the right of her in his wheelchair.

Before the retired couple could present their testimony, Wasserman leaped up to object to Mickey Bohan reading her statement, stating that the couple already had a case against him that they had won. U.S. District Judge Charlene Edwards Honeywell overruled Wasserman's objections, allowing Mickey Bohan to speak.

Mickey Bohan acknowledged in her statement that she and her husband had won a $500,000 judgment against Wasserman and that he was supposed to pay them in $5,000 increments.

Manatee County court records indicate Thomas Bohan sued Wasserman in June 2012, corroborating Mickey Bohan's testimony. In the complaint, Thomas Bohan states he invested $550,000 with the Phillip Roy Fund in December 2003.

The complaint states that Wasserman closed Phillip Roy Financial and Phillip Roy Fund, and no longer responded to phone calls or written communications from Thomas Bohan. It also alleged that Wasserman failed to provide year-end accounting and tax information and that Wasserman was personally responsible for preventing Thomas Bohan from accessing his money.

A final judgment was entered in June 2015 allowing Thomas Bohan to recover from Wasserman the principal sum of $500,000.

They never saw a penny of the money, Mickey Bohan said.

Because of their investment and lack of returns, the couple were forced to sell their retirement home in Sarasota and their summer home in New England, Mickey Bohan said.

"Please, judge, protect the seniors of Florida," Mickey Bohan urged Honeywell several times during her statement.

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Bruce Stone, an advertising executive for iHeartRadio,said it was unfortunate that a person who was in a position to do good and could help people chose instead to do the opposite — stealing not only from victim investors but his company as well.

Stone said Wasserman acted in a systematic and deplorable way, and that Wasserman's company did exactly what it was designed to do. He added that Wasserman is someone who needs to sit in a room with bars for the rest of his life.

"He's earned a place outside of society," Stone said.

Laine D’Souza wasn’t in the Tampa District Courthouse on Jan. 12 to give her testimony in person before Honeywell. Instead, a video recording was played on a projector hanging above the courtroom.

In the recording, Laine D’Souza sounded angry, accusing not only Wasserman of the pain he's caused her family and others but also his wife and son.

Following the video, Wasserman jumped up to stand up for his wife and son. He stated he was fine being targeted and having accusations thrown at him, but he was tired of accusations and hatred being directed toward his family, whom he said had nothing to do with the business.

'Investors were collateral damage': Wasserman speaks during hearing

Wasserman said he doesn't blame his investors, whom he hasn't spoken to in more than three years, for being angry, but he blamed the government for stoking that anger in their pursuit to get to him, treating the investors as collateral damage in the process.

"There is no evidence I ever sought to take advantage of these clients," Wasserman said.

For the last time during the case, Wasserman presented his side and maintained his innocence while addressing the anger directed towards him by investors and attempting to change the narrative about his characterization.

Wasserman pointed out that the government said he had shown no remorse for his actions, yet, when he asked about whether he could send money to certain investors to pay them back, he was told he'd be open to more charges. He told the judge that the government hadn't wanted him to pay back the investors while the case was ongoing so they would be angry.

In addition to blaming the government for the investors' anger, Wasserman also blamed his former co-defendant and employee Ken Rossman, who worked with Wasserman to convince retirees to invest in FastLife.

Rossman pleaded guilty in July 2021 to conspiracy to commit wire fraud and mail fraud, as well as aiding and abetting the preparation of a false and fraudulent income tax return, according to previous Herald-Tribune reporting. He was sentenced to a probationary period of five years, with 12 months of home confinement. Rossman testified against Wasserman during the trial as part of his plea agreement.

During his allocution, Wasserman divulged details of his upbringing and past to set the record straight about his character, including his multiple charitable acts in Sarasota and Manatee counties.

Wasserman described how his grandfather and father were both involved with the mafia in Chicago and that at one point his father had told Wasserman, who was 13 years old at the time, that if anything happened to him, Wasserman was to slit the throat of a mobster's daughter.

Determined to not end up like his father, Wasserman said that "everything in my life was designed to be anti of my father."

After opening his financial services firm in Sarasota, Wasserman said he donated to various organizations and schools and paid for several funerals while remaining mostly out of the spotlight.

Of the various charitable acts Wasserman said he did, previous Herald-Tribune reporting confirmed that Wasserman donated $5,000 in 2007 to the Booker High School wind ensemble so they could play at Carnegie Hall in New York City, and he started an annual Holiday Gift Shopping event where "Littles" of the Big Brothers Big Sisters of the Sun Coast received gift cards to shop at Walmart.

Further, Wasserman pointed out that according to an expert in financial forensic reviews who went over an audit of the company, it showed that FastLife wasn't a Ponzi scheme because most of the money was going back into the company and not to an offshore account like in a typical Ponzi scheme.

Franklin Worrell, a private investigator focused on financial forensic reviews with a firm called Quick Group, was called during the Jan. 12 hearing to walk through the loss amounts from FastLife by looking at FastLife's financial activities from August 2016 through 2019.

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Worrell said that according to the government's exhibits which he was basing his testimony on, FastLife was breaking even in 2019, with only about $18,000 from investors coming into the company and $778,000 being made in commissions, with Wasserman only taking about $83,000 for himself.

Worrell added that a large portion of the money brought in went back into the company for payroll, marketing and rent, and about $126,000 went to investors.

Several of Wasserman's witnesses who appeared via Zoom Wednesday gave statements about how he was working with them through affinity marketing and with his unique skill set, had helped them secure high-paying clients. Not only did the witnesses speak to his ability to make and close sales, but also his work ethic. One witness described how Wasserman worked seven days a week from about 7 a.m. to late at night.

Wasserman added that despite the bad publicity from the case, there were still people who wanted to work with him. Since his living expenses are low — only about $3,000 monthly — he said the rest of the money he would make from the agents closing deals would go directly towards paying restitution. It was estimated that he could make an excess of six figures in a year.

Wasserman also listed off his health problems, including Stage 3 Kidney Disease, and his fear of catching COVID-19 while incarcerated as reasons why home confinement, or home incarceration as he put it, would be better for him.

It would also allow him to focus on restitution and his civil case against the government and the Department of Financial Services, which has a tentative trial date set for next year, according to Wasserman.

Wasserman faced numerous lawsuits in Sarasota County before conviction

Previous Herald-Tribune reporting from 2007 indicated that Wasserman's company, Phillip Roy Financial Services, had been sued previously by several couples, including at least two Sarasota couples, who said the company's representatives misled them.

"There are 11 other recent complaints on file with state regulators against the company's president, Phillip R. Wasserman, who holds investment seminars about annuities and life insurance for thousands of Florida seniors every year," the reporting said.

An additional nine complaints were filed with the Office of Insurance Regulation, which oversees equity-indexed annuities.

At the time of that reporting, Wasserman stood firm in believing he hadn't done anything wrong and that the couples that sued him simply could have asked for their money back. He also said some of the complaints were from competitors who lost investors when they switched to his company.

Wasserman continued to host seminars following the lawsuits in 2007 in the Sarasota area for retirees who had a net worth of more than $1 million, according to previous reporting.

Sarasota court records indicate that at least seven more lawsuits were filed against Wasserman between 2009 and 2020 for contract and indebtedness.

Gabriela Szymanowska covers the legal system for the Herald-Tribune in partnership with Report for America. You can support her work with a tax-deductible donation to Report for America. Contact Gabriela Szymanowska at gszymanowska@gannett.com, or on Twitter.

This article originally appeared on Sarasota Herald-Tribune: Phillip Wasserman sentenced to federal prison for 15 years for fraud