He Grew Up in the Shadow of the ‘Wolf of Wall Street.’ Then He Got Into Debt Settlement.

In the early 1980s, 19-year-old Jordan Belfort — who would go on to become known as the Wolf of Wall Street, a title he bestowed on himself in a tell-all memoir — had a fortuitous encounter on Jones Beach, on Long Island, with another teenager selling ice cream named Stephen Drescher.

The two became friends. Prosecutors would later note their shared hustling spirit, a drive for entrepreneurialism that curdled into a drive for grift. Within a few years, Mr. Belfort started building a pump-and-dump stock-scam empire. He took Mr. Drescher under his wing as he built a boiler room brokerage that would go on to defraud more than 1,000 investors, later memorialized in Martin Scorsese’s box office hit “The Wolf of Wall Street.”

Mr. Belfort’s enterprise collapsed in the late 1990s, when he was arrested and pleaded guilty to fraud and money laundering. Mr. Drescher went down not long after, convicted of securities fraud and sent to federal prison for nearly four years.

He, too, had a spiritual successor of sorts: his stepson Ryan Sasson.

Bronzed, athletic and self-assured, Mr. Sasson is chief executive of Strategic Financial Solutions, a large employer in Buffalo often hailed by politicians and business publications as a fast-growing exemplar of corporate citizenship. Its call center, packed at its peak with hundreds of workers, offers well-paying jobs in a region eager for economic expansion. Strategic regularly makes four- and five-figure philanthropic donations to local causes; New York’s lieutenant governor cut the ribbon at its Buffalo office opening. On its website, the company, which also has a Manhattan office, boasts of luxe perks like massage therapy rooms and bonus trips.

The company’s primary business is debt settlement, helping consumers buried in credit card bills negotiate down what they owe and extract themselves from financial turmoil. Strategic has more than 75,000 clients and has saved them $1 billion over the last three years through its negotiated debt deals, the company’s president said in January in a legal filing.