Before the Chairman’s Fund, before the Greenlight empire, before the title of “the nation’s No. 1 business, money and wealth coach,” there was a federal prison cell. Terrence Chalk, of Passaic, New Jersey and Orlando, Florida, was convicted in August 2009 of identity theft and conspiring to make false statements to financial institutions, sentenced to 76 months, and spent the better part of six years incarcerated for a fraud scheme he ran through a White Plains computer systems company called Compulinx Managed Services Inc. When he emerged and began pitching his next investment vehicle, he told prospective clients he had “retired after selling a computer company for $18 million in 2006.”
The company had not been sold. He had been in prison. Between 2017 and 2020, operating under the alias “Dr. Terrence Cash” and four entities operating under the Greenlight brand, Chalk raised approximately $5 million from approximately 40 investors — mostly elderly retirees and former civil servants, many of them recruited at Black church seminars — through a fictitious investment fund he called the “Chairman’s Fund.” The SEC filed its civil complaint on November 3, 2020. Chalk pleaded guilty to investment adviser fraud in May 2024. On June 10, 2025, a federal judge sentenced him to 36 months in prison and three years of supervised release. The final civil judgment was entered April 15, 2026.
The Identity He Built to Bury the One That Had Already Been Convicted
The alias was not incidental. Chalk constructed “Dr. Terrence Cash” with the specific intention of preventing investors from finding his criminal record. He was not registered with the SEC, held no securities licenses, and had no legitimate investment credentials. What he had was a criminal history that would have ended any pitch before it began. So he invented a new name, a new biography, and a new origin story.
On his website and at speaking events, Chalk presented himself as a seasoned entrepreneur and accredited private investor with over 25 years of experience, a coach, author, and philanthropist who had achieved financial independence and was now sharing the “hidden secrets of the wealthy” with ordinary working Americans. He spoke at minority networking conferences, hosted dinners for prospective clients, and invited them to company retreats. The origin story he gave — the $18 million company sale — was designed to explain both his wealth and his availability to coach. Investors who asked why someone so successful was holding seminars in church halls received the answer in his own brand language: he was a man of faith, giving back to his community.
How the Chairman’s Fund Recruited Retirees and Emptied Their Accounts
The Chairman’s Fund was not an investment fund. It had no portfolio, no audited financials, and no structure that could have sustained the returns Chalk promised. He told investors they could expect guaranteed quarterly cash payments of between 12 and 77 percent annually — returns no legitimate fund could offer without an underlying strategy Chalk had never developed. He described the fund as an elite arrangement in which clients purchased equity stakes in Greenlight and he personally vetted each investment opportunity before deploying their capital.
To maximize what he could extract, Chalk advised clients to transfer their existing retirement accounts and pension savings into newly established accounts at a self-directed IRA custodian, then direct those funds into the Chairman’s Fund. The result, in several documented cases, was that investors who followed his instructions incurred massive early withdrawal penalties before losing the underlying capital as well. One investor, the SEC complaint documents, incurred a $130,000 penalty for withdrawing from a pension account after Chalk told him the Chairman’s Fund would make up the loss within a year. The investor never recovered the penalty and lost more than 75 percent of his principal on top of it. At first, early investors received their promised quarterly checks — funded by the money of later investors, the standard mechanism of a Ponzi arrangement. By late 2019, most payments had stopped. When investors demanded explanations, Chalk told them they had committed not to withdraw their money for ten years. No such agreement existed.
The Spending Record That Replaced the Investment Portfolio
The DOJ’s arrest complaint and the subsequent criminal proceeding document where the $5 million went with specificity. Chalk directed approximately $1.8 million to Ponzi payments to prior investors — the minimum required to keep the scheme credible long enough to recruit more. What remained went to Chalk’s personal accounts and his personal life. He spent approximately $1.7 million on credit card bills charged to cards in his own name, in the names of associates, and through business accounts that commingled fraud proceeds with personal spending. He paid more than $74,000 to a luxury BMW dealership, approximately $17,000 on NBA season tickets, $30,000 at a jewelry retailer, and more than $20,000 to a prison inmate. He also paid tens of thousands of dollars to a criminal defense attorney handling a personal matter — drawn from the same accounts holding his investors’ retirement savings.
Of the approximately $5 million raised, Chalk invested at most $1.2 million in actual ventures — each described in court records as unprofitable. One $295,000 investment went to what the criminal complaint describes as a “speculative cannabinoid venture,” from which most of the money was lost. The swimming pool at his home was installed on investor funds. The Chairman’s Fund, the SEC’s complaint concluded, was fictitious from the moment Chalk described it to his first coaching client.
What the DOJ Said, What the Court Ordered, and Where Chalk Is Now
Acting Manhattan U.S. Attorney Audrey Strauss captured the scheme’s core at the time of Chalk’s 2020 arrest: he had concealed his criminal past, failed to make the promised investments, and routed most of what his clients gave him into personal spending while they were left with broken promises. FBI Assistant Director William Sweeney was more direct: “His real name was Terrence Chalk, and he was a previously convicted felon whose pseudonym spelled out exactly what he was after: cash, and lots of it.” Former SEC Chair Jay Clayton, serving as U.S. Attorney for the Southern District at the time of sentencing, noted that Chalk had exploited shared ethnic and religious backgrounds to build false trust — a pointed description of the church seminar strategy that brought in the majority of his victims.
Chalk pleaded guilty on May 7, 2024, to one count of investment adviser fraud before the United States District Court for the Southern District of New York. On June 10, 2025, he was sentenced to 36 months in federal prison and three years of supervised release in Case No. 1:21-cr-00049-ALC. The April 15, 2026 civil judgment orders disgorgement of $1,731,423 plus $13,078.64 in prejudgment interest, with those amounts deemed satisfied by the restitution ordered in the criminal case. On April 24, 2026, the SEC also permanently barred Chalk from association with any broker, dealer, investment adviser, municipal securities dealer, or transfer agent.
Conclusion
Terrence Chalk ran two fraud schemes separated by a federal prison sentence, and the second was more destructive than the first. He targeted investors whom regulators specifically identify as among the most vulnerable to affinity fraud: retirees, former civil servants, and members of faith communities who extended trust based on a shared sense of identity. The 36-month sentence reflects a man who returned from prison and immediately began building the infrastructure for a new scheme, this time under a name chosen to describe his intentions — and a title, “Dr. Cash,” that the FBI noted required no translation. The investors who transferred their pension accounts on his instruction are receiving restitution from a criminal judgment against a man who has spent the proceeds of two separate fraud schemes and now faces a third chapter of supervised release.
