Jake Paul knows that he will have his work cut out for him in the ring ahead of his next fight.

He will also have to get far more creative when it comes to another pre-fight tradition.

Paul has made a point to challenge his opponents to a side bet in the build-up to their eventual clash. He extended such an offer to his next foe, record-breaking former UFC champion Anderson ‘Spider’ Silva. The two will collide atop an October 29 Showtime Pay-Per-View event from Gila River Arena in Glendale, Arizona. The financial stakes are already set, though the bonus for the winner has yet to be determined as the two have yet to find common ground.

“I was gonna say, if you beat me, I’ll get a Spider tattoo,” Paul offered up during their kickoff presser Monday afternoon at NeueHouse Hollywood in Los Angeles.

A similar bet was made with former UFC welterweight champion Tyron Woodley ahead of his first fight with Paul last August 29 in Cleveland, Ohio. Paul won by split decision, which left Woodley (0-2) on the hook to get a tattoo reading, “I Love Jake Paul”, which he had etched on the inside of his middle finger.

The same offer was respectfully rejected this time around.

“No, no, no, stop. You don’t need a Spider tattoo. I know you’re my fan,” Silva shot back, drawing a rise from the media and crowd and even a hearty laugh from Paul. “Don’t worry. I’m your fan, too. But I hate tattoos.”

Facing an opponent with whom there is no real animosity for the first time in his pro career, Paul (5-0, 4KOs) was momentarily at a loss for words while honoring his opponent’s beliefs.

“I’ll come up with a different bet, none that doesn’t have anything to do with tattoos,” promised Paul. “We’ll come up with it during fight week.”

Paul sought additional stakes for scheduled bouts with a pair of far more contentious rivals in England’s Tommy Fury (8-0, 4KOs) and second-generation boxer Hasim Rahman, Jr. (12-1, 6KOs), neither of whom made it to fight night for a variety of reasons.

Woodley satisfied the terms of their bet ahead of their first fight, prompting Paul to grant him a rematch. It came as a backup plan, as Woodley replaced an injured Fury last December. Paul won via sixth-round knockout, leaving him with the honor of knocking out every opponent he’s faced after going the distance with Woodley four months prior.

One bet that Paul claims to remain unsatisfied was a seven-figure wager with UFC president Dana White ahead of his eventual knockout win over former MMA fighter Ben Askren last April in Atlanta, Georgia. Paul claims that the outspoken UFC figurehead still owes him a cool million, though is also willing to provide White with a second chance.

“Even Dana White did not think I would take this fight. Dana, I know you’re watching bro. You still owe me a million dollars from when you bet against me on Ben Askren,” noted Paul. “I want you to come out of hiding, stop being a bitch and make a bet against me—and actually pay up this time.

“You didn’t think I’d take this fight, so let’s make a bet. Let’s up up a mill, let’s put up two mill, let’s put five-mill on it. But I bet you won’t, Dana, because you’re a bitch.”

Jake Donovan is a senior writer for BoxingScene.com. Twitter: @JakeNDaBox