In fact, it continues to be a hobby Flynt has indulged in since the 1970s, when he offered up to $1 million (or more than $6 million in 2017 dollars) to anyone with “documentary evidence of illicit sexual relations with a Congressman, Senator, or other prominent officeholder.” He has also offered rewards for Mitt Romney’s tax returns or damaging tape of Trump when he was the Republican nominee, and has made multiple payouts to informants in a broad campaign to expose hypocrisy among right-wing “family values” politicians.

So I decided to do this…let's see what happens. pic.twitter.com/Xpy4qrwHU7

— Larry Flynt (@ImLarryFlynt) October 15, 2017

But how does he pay for it all? Many were shocked last month when Flynt’s peer, Hugh Hefner, died at age 91 with what may have been as little as $15 million in assets. That was in part because the rise of internet pornography gutted Hefner’s Playboy empire, and one might think Flynt had been battered by the same storm.

But when he was considering taking the company public in 2014, the now 74-year-old Flynt told USA Today that the privately-held Larry Flynt Publications was worth more than $500 million. That’s plausible because, while Hustler’s print circulation, like Playboy’s, was decimated by digital disruption, Flynt has aggressively diversified into a sprawling empire. His businesses now include video porn production, brand licensing, real estate, and even a casino. He told Forbes in 2014 that publishing accounted for less than 5% of his company’s revenue.

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One key to Flynt’s enduring wealth seems to be that, in contrast to the free-spending Hefner, Flynt has always been as focused on the bottom line as on political provocation. “My editorial staff on Hustler is 7,” he told the Daily Mail in 2015. “[Hefner’s] is probably somewhere between 40 and 50. I make a profit whereas he’s losing money every month.”

That attention to fundamentals has given Flynt the leverage to grow his core operation steadily, acquiring multiple other producers of adult entertainment, and growing divisions including the international cable TV operation Hustler TV. So while the Playboy empire was often on the rocks in Hefner’s final years, Flynt’s Beverly Hills headquarters still appear to be bustling. In fact, Flynt reportedly considered a bid to buy the Playboy Mansion last year.

Larry Flynt Publications has even periodically moved beyond adult content, running a few alternative newspapers starting in the late 1970s, and publishing music and video game magazines before they, too, were forced out of business by digital competition. Flynt also licenses the Hustler brand to a successful chain of gentlemen’s clubs, with more than a dozen locations spanning from Manhattan to Las Vegas, and even one in the U.K. (That marks an intriguing consonance between Flynt and Trump, who also heavily licenses his name).

It all adds up to an impressive run for a business that started as a single bar in Dayton, Oh. in 1965. The $10 million Flynt is promising for compromising dirt on the President is hardly pocket change, but he’s definitely good for it.