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High Roller Bill Perkins Talks About His Plan To Die With Zero

Hedge Fund Manager And High-Stakes Poker Player Explains How To Optimize Your Life

by Julio Rodriguez |  Published: Dec 02, 2020


If you are an especially envious person, I wouldn’t recommend checking out Bill Perkins’ Instagram page. The 51-year-old just looks like he is having too much fun. But there’s a reason why the jet-setting Perkins is usually spotted with a smile on his face, even when he’s battling it out on the felt with some of the best players on the high roller cash game and tournament circuit. The Jersey City, New Jersey native is on a mission to Die With Zero, using all of his resources to make the most out of his time on earth.

Perkins has put together a wildly successful business career, working his way up from a part-time limo driver and screen clerk on the New York Mercantile Exchange, to being a broker and then running his own options desk. He currently manages the Houston-based energy hedge fund Skylar Capital, and specializes in managing risk with an emphasis on natural gas and other related markets.

He’s also a part-time film producer, and has worked with stars such as Samuel L. Jackson, Carrie-Anne Moss, Liam Neeson, Justin Long, Rene Russo, Oliver Platt, Billy Bob Thornton, Eva Longoria, Christina Ricci, and Michael Sheen.

Perkins is known to the poker world, however, mostly for his time on the high roller circuit. He has $5.5 million in career live tournament earnings, with his biggest score coming last year when he final tabled the £1 million buy-in Triton Super High Roller in London. In 2013, he narrowly missed out on a World Series of Poker bracelet, finishing third in the $111,111 buy-in Big One For One Drop high roller for a $1,965,163 payday.

He has also been the catalyst for some of the more outlandish prop bets in the poker world in recent memory. He once paid Jeff Gross $500,000 to get a specific tattoo that he has to keep for life. He’s had several high-profile bets with Antonio Esfandiari, including a must-lunge-to-move bet that got Esfandiari disqualified from a tournament, and a chastity bet that featured a quick buy out. He even paid out the Staples brothers when they were able to trade body weight.

Perkins lost nearly $1 million to Dan Bilzerian and later Brian Rast when the social media star and poker pro were both able to bike 300 miles from Las Vegas to Los Angeles. There was even talk about an insane rowing bet from New York to England.

Now, Perkins is hoping that his fast-living and fun-loving lifestyle catches on with others, sharing his philosophy in the new book Die With Zero: Getting All You Can With From Your Money And Your Life. The book focuses on optimizing choices to allow people to thrive, rather than just survive.

Card Player caught up with Perkins for an episode of the Poker Stories podcast, where he talked about his start on Wall Street, getting nervous playing high-stakes poker, and his new book. Here are some of the highlights. You can listen to the full episode on Apple Podcasts, Stitcher, Spotify, or any podcast app.

Julio Rodriguez: Your father (who later became a politician in the New Jersey General Assembly) and great uncle played in the NFL, and you played football at the University of Iowa. I’m assuming football was a big part of your life growing up?

Bill Perkins: This was the leather helmet days, right before the NFL was the NFL. My father ended up going to law school, so it wasn’t until my Pop Warner days that I really got into football. I didn’t really watch that much TV as a kid, definitely not much football.

JR: Other than football, what was your plan in school? You graduated with a degree in electrical engineering.

BP: The plan was to be the biggest slacker I possibly could and chase women across campus. (laughing) My mom told me that I was in college to learn, not to get a job. If I wanted a job, I could just go to trade school. I thought that was some of the better advice my mother gave me, because it allowed me to take classes I wouldn’t have otherwise taken.

Bill Perkins Playing In The Big One For One DropJR: After college, you went to work on the New York Mercantile Exchange, starting as a screen clerk and driving a limousine at night to pay the bills, before eventually becoming a broker and then running your own options desk. I read that you were inspired by the 1987 Michael Douglas and Charlie Sheen film Wall Street.

BP: It’s kind of cartoonish, right? It was this character (Gordon Gekko) that had just came out. The movie was really about the downside of unbridled greed, but that wasn’t the message I was getting. (laughing) The message I was getting was, ‘Holy shit, these equity guys make a f**k ton of money and are able to do whatever they want.’

JR: In the book, you talk about how you were fired from one of your jobs, and that it made you hungrier.

BP: It was a time when I was moving out of my slacker stage and into my integrity and driven stage. I think it kind of reignited me. You know, ‘Get your shit together!’
I was brokering over the counter. One of my clients had me come down and visit them, but it ended up being a job interview. You never know when you are being interviewed! They offered me the job to run their options desk in Houston, and I snap took it.

Prior to that, I was one of those northeast guys, New York City. You could never pay me to move to Texas. But I would have went to Siberia to trade. They could have told me they had a little trading station in the middle of a war zone and I would’ve gone for it.

JR: Throughout your career, you’ve seemingly never been afraid of risk. Is that an accurate assessment?

BP: I’m not afraid of failing. [Especially early on,] I had very little fear of getting egg on my face, crashing and burning, looking like an idiot, or being broke. When you’ve been broke, and you’ve gone through it and survived it, you kind of tell yourself that you’d be okay going back. You don’t want to go back, but you know it’s doable. You’re okay taking a prudent risk in order to get to what you really want. Having navigated being busted, and knowing that I could always hustle and get a job here or there, I was willing to shoot for the moon. That was my attitude back then.

JR: These days, the message you are preaching with your book Die With Zero is more about maximizing life experiences, using resources more effectively to enrich yourself.

BP: When I was younger, I had this idea that it was okay to be rich, but that you didn’t want to be old and rich. When you are 21 or 22 and trying to make it, you see these old rich guys and you think to yourself, ‘So what if you [have money], what are you going to do with it?’ At a certain point, the money is useless. So, I started exploring that concept, about the utility of money and how it changes with age.

JR: You bring up examples in the book of people who spend their whole lives working and saving for retirement, only to pass away before being able to enjoy the money. Or perhaps they live long enough, but don’t have the health or energy to do what they wanted to when they were younger. They suddenly look back at their life and don’t have any experiences to show for it.

BP: They wasted no money, but they certainly wasted their lives. We focused on the book on [the concept of] converting money into experiences, but also converting health into experiences at the right time. You might not be able to hike later in life, so those experiences are meant to be done earlier. If you want to stay home and watch Jeopardy!, you can do that when you are 80. You might want to go hike that mountain now instead.

What makes you, you? What constitutes you? It literally comes back to your memories and experiences. You are loaded with these memories and experiences, and they give you fulfillment. Why do I smile when I see my daughter? Well, I made her, I’ve spent time with her, and I have experiences with her.

From this point now, until the grave, you have to think about modeling your life. You have got to think about life cycle modeling. What is your life experience going to be from now until the day you die?

JR: Of course, not everyone has your financial resources, so it’s easier said than done for many who are paycheck to paycheck and have to work long hours to survive. But your book points out that this concept of maximizing your resources isn’t just for those who are wealthy.

BP: Get off autopilot and be deliberate about your life. Plan it out. That’s resource agnostic. There’s time, health, and money, and those variables will change over the course of your life. How am I going to allocate those resources to get the maximum fulfillment, the maximum experience? I use the word ‘experience’ very broadly. It’s not just about traveling the world. It could be going to a club, giving money to charity, or just spending some time playing cards with your daughter.

When people ask me how I [became successful], I tell them I don’t watch TV. I don’t get that much value out of television, because it sucks a lot of hours. If there’s a great show and you love it, and it gives you enjoyment, then go ahead and watch it. I’m not here to tell you what to do. You have a finite number of hours on earth, and TV sucks a lot of them. In the amount of time you are watching TV, you can be creating all of these experiences or enriching your life in some way. If you have an extra two hours a day back, it’s amazing what you can do.

JR: Time is a very important resource to you, and the book mentions a few examples of how you let time guide you in your decision making.

BP: If I eat 600 calories of cookies, that’s an hour on the treadmill at a 15 incline at 3.1 miles per hour. I’m not one of those guys that loves being on the treadmill. In fact, I hate it. Is the cookie worth an hour of my time? A lot of time, the answer is yes. There are some damn good chocolate chip cookies out there. Sometimes it’s no. The cookie isn’t worth it.

I’m on the area of the curve where I’m now converting money to time. I buy things to save me time. Things like cleaning services, private travel, food delivery, etc. I’m just into soaking up and enjoying life as much as possible. I’m trying to get this one right.

I’m going to die. That is going to happen in no uncertain terms, and it’s not that far away. I’ve been alive [longer] than I will most likely live. I don’t get a second chance. It’s not like I’m going to hit the grave and get a do-over like Mario Brothers. The moment passes and then it’s gone forever, so I want to soak it up and savor it. I’m all about net fulfillment over net worth.

JR: Is that why you don’t work as much as you used to, and spend a lot of your time on a yacht in the Caribbean?

BP: I mix the work into my vacations, these trips that I take throughout the year. It’s not like I just set aside two weeks every year for Disney World. I’m fortunate that I’ve gotten to the point where I can make my office wherever I want, wherever is most enjoyable.

JR: Why aren’t more successful businessmen living life like you do? Why do they continue to keep their foot on the gas even after making more than enough money to live out a lavish life?

BP: Habits have a way of making you believe that the habit is the goal. In order to get good at something, you have to spend a lot of time on it, obsess over it, and spend many hours honing that craft. You became habituated into doing things.

A lot of people when they drive home, they don’t remember anything from the drive. They are on autopilot, just making the right turns when they need to, not thinking about their actions. It’s the same with careers. People put in 10,000 hours working at something, it becomes a habit, and they become disconnected from the reason why they went to work in the first place. They lose sight of the other important things in their life.

You can put a rat in a wheel with some cheese, and after a while, you don’t even need the cheese. You just show the rat the wheel and they’ll start running. This happens to a lot of people. They go to work, and they put off the reward, convincing themselves that they actually love running in the wheel, when it’s actually just the habit.

JR: You started playing poker in high school with games like acey deucey, and then started taking the game more seriously after moving to Houston. Given the vast amount of money you work with on a daily basis trading, do you have to play the high rollers to feel any sort of a rush?

BP: I like playing poker, and I really like the social aspects of it. But it’s not my day job, I have no delusions that I’m there to make a bunch of money and be a professional. I want to win and I do compete, but I flip for rolls in natural gas trading. That’s where you’ll see me splashing around.

I do get the rush, however, even at the lower buy-ins. There’s a certain number where it needs to aggravate me if I lose. It’s not going to change my life, but it is aggravating. I remember playing $500-$1,000 online, and I shipped kings. I could feel my heart pounding. Then I realized, this was nothing. The amount of money that I had shipped was nowhere near my P&L (profit and loss attribution) trading that day, but the fact that it was in poker, my heart was beating [like crazy].

It’s a great feeling. I’m not as stoic with poker as I am with natural gas trading. With gas, it can be 50x that number, and it is what it is. I’ve done my research, I think it’s the right trade, and if I lose, I lose. There’s really no big sweat on anything. But in poker, I’m not as stoic. I’m way more nervous in poker than in trading. ♠