Selling Trump Isn’t What It Used to Be

“In the grander scheme of things, this collection has not replicated the big hitters emerging during the NFT boom,” said Arda Akartuna, a senior analyst at Elliptic, a blockchain analysis firm.

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Neither Mr. Zanker nor Mr. Trump responded to inquiries about the arrangement. Kevin Mercuri, a spokesman for Mr. Zanker, confirmed his participation in the Trump NFT, noting that it was his first deal with Mr. Trump since 2015. He did not answer questions about precise deal terms.

Mr. Zanker founded the Learning Annex in 1980, using $5,000 he had saved from his bar mitzvah, according to past interviews. It started in New York before spreading across the country and offered nontraditional courses such as “How to Flirt,” “How to Talk to Your Cat” and “How to Marry Rich.”

He became a tireless promoter with a knack for making headlines. In 1982, he cooked up a plan to drop $10,000 in dollar bills off the Empire State Building, in a promotional stunt for the company. He ended up on the front page of The Times after he was interrupted by a bank robbery in the same building and chaos erupted in a mad crush of TV reporters, the police and bags of money.

While he pursued a series of ventures, including an ill-fated chain of massage emporiums called the Great American Backrub Store, his most successful business was the Learning Annex. Its classes doled out advice on both spiritual enlightenment and financial enrichment from celebrities, including Tony Robbins, the self-help guru, and George Foreman, the former heavyweight champion.

But nobody pulled in more people than Mr. Trump, whose first Learning Annex speech, delivered in 2002, was called “Thinking Big: There’s Nothing You Can’t Do!”

“Everybody could see that Trump’s brand was a big thing and growing,” said Steven Schragis, the company’s national director at the time.

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