Sarasota's self-proclaimed 'Annuity King' found guilty in $6.3 million fraud case

The self-proclaimed "Annuity King" of Sarasota has been found guilty on multiple counts of wire fraud and mail fraud, as well as conspiracy to commit wire and mail fraud, according to the U.S. Attorney's Office of the Middle District of Florida.

Phillip Roy Wasserman, 66, faces a maximum penalty of 20 years in prison on each of the conspiracy, mail fraud and wire fraud counts. Prosecutors are also seeking at least $6.3 million in monetary judgment, which is the amount they believe Wasserman bilked out of elderly investors. It is unclear when Wasserman is expected to be sentenced.

Wasserman, a former lawyer and a licensed insurance agent, was indicted in June 2020 by a federal grand jury for running a "fraudulent insurance venture" that included Ponzi-style payments from investors which funded his lavish lifestyle, according to previous reporting by the Sarasota Herald-Tribune.

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Prosecutors stated the money taken from victim investors was used to fund a beach house on Casey Key, vehicles, Tampa Bay Lightning season and playoff tickets, jet skis, and other luxuries.

The 'Annuity King' and Billy Ray Cyrus

Wasserman operated investment businesses, including Phillip Roy Financial Consultants and Phillip Roy Financial Services, in the Sarasota area for years prior to FastLife and billed himself as the "Annuity King" in promotional materials, according to previous Herald-Tribune reporting. He held investment seminars attended by thousands of seniors in Florida.

Months after the first indictments, more charges were filed against Wasserman in November 20202 which included filing false income tax returns and tax evasion. Wasserman asked that the tax counts be tried separately prior to the trial, according to the news release.

Kenneth Murray Rossman, of Bradenton, who was a codefendant with Wasserman, 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 the news release. He will be sentenced on June 8, 2023.

Evidence at trial showed that Wasserman and Rossman falsely misrepresented and concealed information from their victim investors to prompt them to invest in Wasserman's insurance venture, FastLife, according to the news release. Investors were convinced to liquidate traditional investments and borrow funds against their life insurance policies.

Wasserman also appeared to have taken steps to evade payment of more than $900,000 in taxes he owed, while also failing to disclose numerous civil judgments and other pending debts against him, according to the news release. During an investigation into his company, it was discovered Wasserman created a second set of books and fabricated a compensation agreement in order to conceal FastLife's mounting business debts from many individuals, including from business vendors and service providers to employees and independent contractors.

Prosecutors also stated that Wasserman attempted to thwart the investigation by urging one witness to lie and tried to dissuade victim-investors from cooperating with law enforcement, the news release states.

The venture was promoted through television, radio, and print media outlets, according to previous Herald-Tribune reporting.

In 2018, country music singer Billy Ray Cyrus signed on to be one of FastLife's celebrity spokespersons, according to a news release at the time.

Sarasota restaurant owner pleads guilty to conspiracy to defraud the U.S.

Madeline Nikolson, who owned and managed a restaurant in Sarasota, pleaded guilty in mid-May to one count of conspiracy to defraud the U.S. after scamming the IRS out of more than $726K, according to a news release by the U.S. Attorney's Office of the Middle District of Florida.

Nikolson faces five years in federal prison, according to the release. Beginning in August 2013, Nikolson and her partner and co-owner of the restaurant began removing records of daily cash sales from the registers at the restaurant, leaving the record to consist only of credit card sales.

The two then submitted falsified records to tax preparers for their personal income tax returns and corporate tax returns for 2016, 2017 and 2018, according to the release. By doing so, they removed any reference to the approximately $726,105 in sales income from their records, which as a result means they owe more than $100,000 in taxes, according to the news release.

An attorney on behalf of the Boatyard Waterfront Bar and Grill sent a statement to the Herald-Tribune regarding the case.

“The Boatyard Waterfront Bar & Grill has been a standard of the Sarasota food scene for over 12 years. In that time, we have weathered the impacts from the BP Oil Spill, Red Tide, and COVID-19 — all the while staying in business. Indeed, throughout the pandemic, we never took a dollar of government assistance," the statement states.

"We are in the process of resolving tax issues from 2016 thru 2018. This agreement with the government is designed, from all sides, to ensure the restaurant stays open, all the while staying in business and employing dozens of members of our community," the statement continues. "We look forward to resolving this matter with the government and continuing to be a mainstay of this community.”

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: Fraud cases: Phillip Roy Wasserman and Madeline Nikolson are guilty