Poker tournaments tend to be a bit more expensive for Bill Perkins than for other people.

Aside from the high-ticket prices of Super High Rollers, Perkins often loses thousands of dollars in side bets while he’s playing.

A few days ago, during Day 1 of the $100k Super High Roller, Perkins lost another $10,000 when he bet Mike McDonald that he couldn’t do 300 squats during a level of play.

McDonald succeeded in that, but failed in the following bet when he had to complete 350 push-ups in a level. Because McDonald did pass 300, though, Perkins donated a portion of the bet to charity instead.

Perkins: Donated 50% to Charity

Perkins’ increased costs of playing tournaments aren’t even offset by an increased ROI. Before the PCA, Perkins announced that he was going to donate 50 percent of his winnings to charity.

In case you haven’t figured it out, Perkins has a lot of money. Most of it comes from a massive fortune he amassed as a commodity trader and venture capitalist.

That makes his bad track record of prop bets all the more surprising. How can a man who built a fortune making well-informed bets be so terrible at prop betting?

Betting Against Motivation = -EV

“A lot of the prop bets I do are motivating bets,” Perkins said. “So, if I have a friend that’s overweight I’ll prop bet him to better himself.

“Not all of them, but a lot of them are designed for some benefit to come out of the prop bet,” Perkins said.

“When you’re betting against the ability of a human being to do something, you’re generally going to lose.

“Human beings are very very adaptable, fantastic creatures and when they put their mind to it they can pretty much do anything.” 

These prop bets are a combination of two of Perkins’ favorite things: Gambling — Perkins said prop betting was the “relaxation sport of trading”– and helping people.

In one prop bet, Perkins challenged someone to travel only with carry-on suitcases for 16 months because they travelled with far too many things.

Perkins lost the bet but his friend learned to live with less, save hours at airports and value what was truly essential when travelling.

Just for Fun

One of Perkins’ most famous prop bets was when he paid Jeff Gross $550,000 to tattoo a rainbow on his back.

But that was far from Perkins’ favorite.

“I’ve had so many, I probably couldn’t pick out a favorite,” Perkins said. “You probably couldn’t even print my favorite.”

After a bit more recollection, Perkins smiled and remembered the time he offered Antonio Esfandiari $250,000 to abstain from sex for a year.

Could the Magician hold it in for so long?

“Of course not!” Perkins said. “He was getting married, that was a shoe-in. He’s even having a baby right now.”

There’s no evidence more damning than a child in a no-sex bet. Every now and then, Perkins enjoys being on the challenger’s side of prop bets.

“I got to 7.7 percent body fat once once,” Perkins said. “I gained like 6 pounds of muscle and lost fat, it was all natural too, you couldn’t take steroids or anything like that.”

Perkins managed to reach that goal in two months.

“When you’re motivated, there are few things you can’t do,” Perkins said. Motivation and a positive attitude are what helped Perkins succeed in trading.

“Certain people have the ability to handle risks better than others,” Perkins said. “There’s been some work done that when something negative happens to you, the average person needs five to seven positive things to balance it out.

“So a trader can win 6 or 5.5 out of 10 days. If you’re looking for the 5 to 1, 7 to 1 ratio in trading, you’re not going to get it.”

Gratitude is the Key to Success

The trick, Perkins says, is gratitude.

“Being grateful will help give you perspective,” Perkins said. “I’ve seen people in the most dire conditions who are grateful for something and it changes their perspective.

Perkins is an expert at gratitude and can list a number of things he’s grateful for instantly.

“I have two wonderful daughters that I am extremely ecstatic about,” Perkins said. “I was also born at the right time.

“I was born in the post-civil rights era, a time of relative peace and in an expanding economy which allowed me to make a lot of money in trading.”

“I was born to two college-educated parents and had just about every single advantage in life. I have my health too. I’m very happy that in these 10 seconds, I have my health.

“I could keep going and going. I’m also grateful that at times I can pause and just enjoy it all and be present in the moment.”