Selling Trump Isn’t What It Used to Be

When Donald J. Trump announced his foray into NFTs late last year, capitalizing on public interest in his presidential campaign to sell cartoonish virtual trading cards depicting him as a superhero, he was derided for retreating to his huckster impulses.

Anyone seeking insight into Mr. Trump’s decision need look no further than his partner in the enterprise.

The online trading cards are the brainchild of Bill Zanker, a serial entrepreneur who has sold back rubs, gym equipment, self-help courses and, at times, Donald Trump himself. Before Mr. Trump’s political rise, Mr. Zanker co-wrote a book with him, teamed up in a crowdfunding business and, for several years, made Mr. Trump the centerpiece of a real estate road show that sold out sports arenas. Mr. Zanker once boasted in ads of paying Mr. Trump $25,000 a minute to speak.

Times have changed for both men. Mr. Zanker’s best-known business, a for-profit education company called the Learning Annex, has gone dark, and a recent foray into fitness equipment hasn’t taken off. Mr. Trump, who is facing several investigations into his conduct, including his attempts to overturn a fair election, has become far less a symbol of American prosperity than of the nation’s polarizing politics.

In business together again for the first time in more than seven years, the two are seeking to resuscitate a once-dependable formula blending celebrity with unabashed hype. Early sales results hint at just how difficult that project really is.

Mr. Zanker first approached the former president with the idea last year, telling him that the enterprise could bring in as much as $100 million, according to a person with knowledge of the discussions who asked for anonymity to reveal private conversations. In exchange for licensing his name and likeness, Mr. Trump would receive a significant portion of any revenues from sales of what would become known as Trump Cards.

Mr. Trump agreed, much to the disappointment of those around him who wished he had been focused on his 2024 presidential campaign. On Dec. 14, Mr. Trump used social media to promote what he called a “major announcement”: the sale of thousands of digital cards showing him dressed, variously, as a cowboy, an astronaut, and a superhero shooting laser beams out of his eyeballs. The cards looked strikingly similar to images of Sylvester Stallone that Mr. Zanker had commissioned for a separate NFT project last year.

The venture was an unusual step into brash commercialism at a time when politicians typically streamline their finances: Mr. Trump formally announced his new campaign just 30 days before the NFTs were issued for sale. For Mr. Trump, who in the past has sold frozen steaks, vodka, deodorant, eyeglasses, perfumes, vitamins, shirts and mattresses, it was a shift back into branding and licensing.

Some Trump advisers worried that the enterprise would come across as a tacky marketing gimmick. Of even greater concern was the idea that every dollar spent by his supporters on the NFTs might translate into a dollar not contributed to Mr. Trump’s campaign, according to two people familiar with internal conversations who requested anonymity because they were not authorized to discuss the matter.

Despite Mr. Trump’s promotional efforts, the Trump Cards have not, as of yet, become the cash cow they were pitched as.

To date, Trump Cards sales have hit $17.3 million, generating about $5.6 million in revenue, according to an analysis conducted by CryptoSlam, a blockchain data aggregator, for The New York Times. That total includes the $99 original price for each of the 44,000 cards that were sold on the first day, plus a 10 percent royalty each time any of those cards is resold on the secondary market.

For example, when an anonymous buyer paid $43,865 on Dec. 18 for a single Trump card that depicted him in black tie and tails, a $4,386.50 royalty went back to Mr. Zanker to be shared with Mr. Trump. It is not clear how revenues are split.

Industry experts said the Trump Cards’ sales were respectable, particularly after a cryptocurrency crash last year. Still, they pale in comparison to other NFT projects. Perhaps the best known, the Bored Ape Yacht Club, racked up $1.57 billion in sales in 2022.

Many of the cards bearing Mr. Trump’s image were bought by accounts that hold no other NFTs and have not tried to resell their holdings, according to public data. The numbers suggest that the buyers are core Trump supporters rather than avid crypto traders, who speculate on the value of NFTs.

“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.

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.

In 2004, Mr. Zanker began the Real Estate Wealth Expo and built it around Mr. Trump, plastering his face on thousands of copies of his course catalogs, which were stacked in boxes on seemingly every street corner in Manhattan, and on prominent billboards around the country.

“Having Donald Trump speak on real estate is like having Tiger Woods give you a personal lesson on hitting a golf ball,” Mr. Zanker said in a news release. “It’s a once-in-a-lifetime experience for anyone trying to get rich.”

In fact, Mr. Trump’s real estate career has been a financial roller coaster. In 2005, for example, Mr. Trump wrote off more than $100 million in business losses to reduce his federal taxes.

That year, Mr. Zanker bragged of paying Mr. Trump $1.5 million per appearance. Mr. Trump later acknowledged, in a court deposition, that he actually received just $400,000 in cash for each speech. The rest of the fee went to “promotional expenses” such as the billboards and newspaper ads, he said.

Mr. Trump and Mr. Zanker expanded their partnership. They co-wrote a book, titled “Think Big and Kick Ass in Business and Life,” which urged readers to “go with your gut instincts” on major business decisions. To draw attention to the book’s launch, Mr. Zanker handed out thousands of dollars in cash at a bookstore in Manhattan.

The two men founded a crowdfunding platform in 2013 intended to rival Kickstarter. Mr. Trump, perhaps inspired by his partner’s flashy approach, promoted the start-up by giving away three suitcases of cash at an event in the Trump Tower lobby.

As Mr. Trump turned to politics, he walked away from the crowdfunding site. But Mr. Zanker still was able to get in one more deal, helping negotiate his partner’s next book, “Crippled America: How to Make America Great Again.”

While Mr. Trump was in the White House, Mr. Zanker’s businesses struggled. FundAnything ceased posting new donation campaigns in early 2015. The Learning Annex stopped promoting courses online, holding what appears to have been one of its final classes — a speech on podcasting featuring Adam Carolla, a comedian, in Irvine, Calif.

Mr. Zanker looked for new ventures. He opened a fitness club that boasted of always having a fully stocked bar. During the pandemic, he sought $10 million from investors in a home gym equipment company, but publicly available documents suggest he raised only $372,000. The home gym never hit the market.

Last March, Mr. Zanker unveiled his newest reinvention, announcing plans to sell 9,997 NFTs featuring fanciful images of Mr. Stallone.

Despite considerable promotion by Mr. Zanker and Mr. Stallone, the PlanetSLY cards were never released. Mr. Mercuri blamed “the crash in the cryptocurrency market.” A spokeswoman for Mr. Stallone said she was not authorized to comment on the matter.

In August, Mr. Zanker put his 20-acre ranch in Park City, Utah, up for sale for 445 Bitcoin, or about $9 million at the time, announcing in a news release that it was the first time a house was available for cryptocurrency. The release also noted that Mr. Zanker “is now working on a large NFT project with a major celebrity.”

The property is still on the market, now for a cash price of $11 million.

The current listing reads, in part: “Owner must sell — make an offer!!!”

Maggie Haberman, Ben Protess and Russ Buettner contributed reporting.