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Die With Zero

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  • Mark Cuban Learned Boldness From Having Nothing
    • Mark Cuban started small selling trash bags and stamps and later built MicroSolutions, selling it for $6 million by age 32.
    • Cuban says he had nothing to lose moving to Dallas, so bold moves felt low-risk and led to high upside and pride from trying. Transcript: Bill Perkins Mark Cuban, the owner of the Dallas Mavericks and one of the investor sharks on Shark Tank, learned entrepreneurship at a young age. At 12, he was selling trash bags to his neighbors. At 16, he was buying stamps and then reselling them for a profit. Growing up in a working-class family in Pittsburgh, he remembers his mom urging him to learn a trade, like laying carpet. Instead, Cuban went to study business management in college, which he paid for by giving disco dance lessons and eventually buying and running a campus pub. As it turned out, police went on to shut down the pub for underage drinking. And when Cuban graduated, he was still broke. But he now had the skills and confidence to make it in business. So after a short stint working for a bank in his hometown, the 23-year Cuban packed his meager belongings into an old fiat and drove to Dallas, joining a friend from college who’d sung The city’s praises. There, the two shared an apartment with four other guys, where Cuban’s bed was a sleeping bag on a beer-stained carpet in the living room. But he kept hustling. He got a job as a bartender, and another as a salesman in a software store. And when he got fired for defying the boss at the store, he hatched plans for his own company, a computer consulting business called Micro Solutions. A few years later, when he was 32, he sold that company for $6 million and retired for five years. Bet when you have nothing or little to lose. Eventually, Cuban came out of his early retirement and started the business that made him a multi-billionaire. But that’s really besides the point here. What’s most interesting to me about Mark Cuban’s experience is that none of the bold moves that led to this success felt risky to him. Not the move to Dallas or the jobs he took there, not defying his boss, and not the business he started after getting fired. I had nothing, he recalled. So I had nothing to lose, right? It was all about going for it. What Cuban is saying is that he was facing a situation of asymmetric risk when the upside of possible success is much greater than the downside of possible failure. When you face asymmetric risk, it makes total sense to be bold, to grab the opportunity at hand. He said, At the extreme, when the downside is very low or non-existent, as in the nothing to lose case, the upside is really high. (Time 0:00:11)
  • High Upside Low Downside Unlocks Bold Choices
    • Asymmetric risk occurs when downside is small but upside is large, making bold action rational and emotionally rewarding.
    • Even failed attempts yield memory dividends and pride, increasing future happiness despite financial loss. Transcript: Bill Perkins What Cuban is saying is that he was facing a situation of asymmetric risk when the upside of possible success is much greater than the downside of possible failure. When you face asymmetric risk, it makes total sense to be bold, to grab the opportunity at hand. He said, At the extreme, when the downside is very low or non-existent, as in the nothing to lose case, the upside is really high. It’s actually riskier not to make the bold move. The downside of not even taking a chance is emotional, potentially a lifetime of regret and wondering, what if? The upside of taking a chance always includes emotional benefits, even if things don’t work out. There’s a great sense of pride at having pursued an important goal wholeheartedly. If you’re giving something your all, you get a lot of memories out of the experience no matter what happens. That’s just another form of the memory dividend I talked about earlier. When you look back from any point during your life, you will remember your actions in a positive light. In other words, even experiences that don’t end the way you’d hoped can still yield positive memory dividends. (Time 0:02:12)
  • The Younger You Are The Bolder You Should Be
    • Be bolder when younger because failures are easier to recover from and success yields more years to enjoy the payoff.
    • Use youth to Transcript: Bill Perkins The younger you are, the bolder you should be. Bear in mind what I said about investing in experiences, especially when you’re young. The idea is that it’s always good to invest in experiences, but it’s especially good to do it when you’re young. Well, a similar logic applies to being bold. When you’re older, some risks become more foolish than bold. It’s easy to see this with physical risks. When I was a kid, I used to jump off the roof in my garage. It was fun, and I never got really hurt. It didn’t even feel like a risk. But I’d be a fool to try jumping off the roof now. With my 50-year body, I’m heavier and my knees aren’t as good at absorbing shocks. So if I did jump, I’d probably end up in the doctor’s office. And even if the injury didn’t cause lasting damage, I would take a long time to recover from it. In other words, I have much more to lose than to gain from a jump like that. So my days of leaping off the top of my garage are behind me. That happens in a lot of areas, where the balance between risk and reward changes with time, until the window of opportunity is gone forever. When you’re young, every risk you take can pay off in a big way if you succeed. Your upside is huge. At the same time, the downside, in other words, what happens when you take the risk and fail, is low, because you have a lot of time to recover. In poker, for example, you can sometimes buy more chips or reload. Well, when you’re young, you’re at that stage in the game of life when you can reload and reload and reload. (Time 0:03:46)
  • Getting Fired At 23 Didn’t Break His Path
    • Bill Perkins recounts being fired at 23, taking a broker job, and later shifting paths without catastrophic consequences.
    • He emphasizes that even career setbacks provided learning, memories, and recoverable outcomes when young. Transcript: Bill Perkins When I was 23, I got fired from my job as a junior trader at an investment bank. In that job, I had been training for the career I wanted, but one day I came into work tired and was caught resting my head in the booth. Well, that was the end of that job. I was scared and uncertain about what I’d do next, and it was no fun being unemployed for the next month. My unemployment ended when I took a job as a broker, a job that paid well but was not what I really wanted to do, which was trading. Still, I knew I had to do something, and I figured I would see where this broker journey led. I was 23. It was easy to correct course. Even if I hadn’t found the broker job, even if I was an abject failure, I wasn’t going to die. And I wasn’t headed for a soup line. Notice that I’m not saying that being bold in situations of asymmetric risk always leads to success, the way it did for Mark Cuban. Sometimes things don’t go your way, no matter how hard you try. What I’m saying is that the loss is worth it. It was still a good bet because I knew I had little to lose, I had plenty of time to course correct, and I still acquired some great memories. (Time 0:05:23)
  • Give Competitive Dreams A Time-Bound Go In Your 20s
    • If you want a highly competitive career like acting, give it your all in your early 20s and set a time-bound trial before reverting to safer options.
    • Jeff Cohen moved from child acting to law after trying full-force then changing paths. Transcript: Bill Perkins Let’s say you want to become an actor, but you know it’s an intensely competitive field. Most people who move to Hollywood never make it and end up waiting tables between auditions. Your alternative to pursuing a career in acting is a safe office job that doesn’t excite you. So should you leave your safe job behind to move to Hollywood? Well, it depends almost entirely on your age. Not on what your parents are expecting of you or what your friends think you should do. If you’re in your early 20s, you should go for it. Give it your all. Really exhaust yourself trying for what you want. You can give yourself a few years, and if it doesn’t work out, you can still go back to an office job or to school to learn a trade. (Time 0:06:37)
  • Chunk Became A Lawyer After Hollywood Didn’t Stick
    • Jeff Cohen’s acting fame from The Goonies faded after puberty, so he went to college and law school and became an entertainment lawyer.
    • His pivot shows a bold early try can lead to a rewarding second act. Transcript: Bill Perkins If you’ve seen The Goonies, the 1985 movie about a group of kids on a quest for a lost treasure, you probably remember the character named Chunk, the chubby member of the gang of misfits. Chunk was Cohen’s breakthrough role. Until that point, his career had consisted of small parts in TV shows and commercials. After The Goonies, the exuberant funny Cohen seemed on track for a big career in Hollywood. But new roles failed to materialize. What happened? Puberty had turned him from chunk to hunk, Cohen likes to say with a laugh. Hollywood is full of sad stories of former child actors. But fortunately, Cohen’s story isn’t one of them. He went on to college and law school, specialized in entertainment law, and is now a partner in his own firm. (Time 0:07:24)
  • Don’t Defer Bold Life Choices To Retirement
    • Don’t postpone big life risks until retirement; health and years of enjoyment decline, so take major life experiments earlier.
    • Perkins warns the ‘I’ll do it when I retire’ mindset is often a massive blunder. Transcript: Bill Perkins A great plan. At that point, chances are you now have people in your life who are truly depending on you, like a spouse and children. If that’s the case, your failure is no longer your own. It affects other people. It’s for the same reason that I stopped riding motorcycles and taking flying lessons once I had kids. In my mind, I no longer had the right to put my life on the line for the sake of those thrills. And so it is with all kinds of risks. The older you get, the more you have to lose. But it’s not just the stakes are higher, the potential rewards are lower. So even if you’re a lone wolf or your kids are grown and flown, the risk-reward balance still isn’t in your favor when you’re older. In the best-case scenario where things go spectacularly well for you, you’ll have fewer years to enjoy that success. Wouldn’t you rather have taken the big risk earlier in life? I can’t say it’s foolish for anybody to start pursuing their dreams in their 50s because everybody’s circumstances are different. And if you missed your chance to do what you wanted when you were younger and you see your upcoming retirement years as your last chance to follow your dreams, I’d say better late than Never. (Time 0:08:19)
  • Quantify Moving Fears With Time And Travel Cost
    • Quantify relocation fears by calculating time spent with loved ones and the highest one-way travel cost, then compare to salary gains and opportunity.
    • Perkins used this method to justify moving from New York for a trading job. Transcript: Bill Perkins Quantify the fear, the case for moving. One of the biggest ways people avoid bold action is an aversion to moving and travel. Many people won’t even consider moving to a different city. And when an opportunity far from home does arise, I often hear them saying things like, I won’t know anybody there, or I want to stay close to my mom. It’s amazing to me that people will root themselves and not seek any new life adventure because they are fearful of moving away from two or three people. If you do that, it’s like letting those two or three people choose where you live. It’s not that you shouldn’t care about maintaining relationships. It’s that if you think about the problem rationally, you might discover that you can have the adventure and still maintain wonderful relationships, in addition to making new friends Where you go. How do you think through this question rationally? My answer is to quantify every single fear. For example, let’s say you have an opportunity to move across the country or across the world for an exciting job that pays $70,000 a year more than your current job. But you’re afraid you’ll lose touch with your friends and family. When I hear something like that, I ask a couple of questions. One is, how much time do you spend with these people? Often, it’s not that much time at all because we tend to take for granted what is readily available. The other question I ask is, how much is a round-trip first-class ticket from here to there on no notice? This is the highest price you would have to pay to see people you’d be moving away from. So how does that price compare with your salary gain, not to mention everything else you stand to gain from moving? Even after doing these calculations, people still sometimes decide to stay put. That’s their choice, of course, but what I want to point out is what they are doing is saying that they are willing to pay $70,000 for the comfort of not having to move. If I had never been willing to move, I would have passed up the biggest career opportunity of my life. (Time 0:12:11)
  • He Left New York To Trade In Texas And Loved The Outcome
    • Perkins moved from a high-paying broker job in New York to become a trader in Texas after an unexpected interview during a client trip.
    • He embraced risk, built a new life in Houston, and remembered owning a horse and buying a shotgun at a charity auction. Transcript: Bill Perkins I was hired for after getting fired two years earlier. As a natural gas broker, I was making good money, about 10 to 15 times what I was earning in my first job out of college. And I was having fun with my high salary, but I hated that job. I hated having to cold call people. And I found it distasteful that my success was so dependent on whether a particular person I was calling liked me or not. Also, the nature of being a broker was that my upside was capped no matter how well I performed. I had some control, but not as much as I wanted. That’s why I wanted to be a trader. If a broker is like a real estate agent, a trader is like the person who buys and sells houses. As a trader, you take all the risk and get all the reward. The opportunity to become a trader came unexpectedly. As part of my broker job, I was making what I thought was a routine trip to visit a customer in Texas. Little did I know that I was actually being interviewed. At the end of my visit, my customer offered me the job of head options trader at his company. I remember negotiating with him, as if I were not sure this was a job I wanted to take. But in the back of my head, I was thinking, where are my bags? I’m ready to move. Other people didn’t understand why I’d want to leave a cushy job in New York City to take a job so risky that I didn’t know if I’d make any money. I moved to Texas, of all places. I’ll admit, I had my own stereotypes about Texas, or anywhere south of the Mason-Dixie line. Really, especially as a black person. But my desire for potential riches that being a trader could bring was so great, I would do anything for the chance to try. I would move to Siberia if I had to. I also knew that I’d hate myself if I didn’t take the job. And what did I really have to lose? If it didn’t work out, I could have gone back to New York City and become a broker again. And knowing that I had tried it would make me proud of myself for the rest of my life. And would make me feel that my life was more meaningful. In this way, even negative experiences can bring positive memory dividends. High upside, low downside. Everything happened to work out. I succeeded as a trader and came to Love, Texas. (Time 0:14:14)
  • Upbringing Shapes Risk Tolerance And Fears
    • Risk tolerance often stems from upbringing; Perkins contrasts his moon-lassoing ambition with his mother’s preference for secure government work.
    • Understanding this origin helps distinguish prudent caution from fear-driven paralysis. Transcript: Bill Perkins Easy for you to say, Bill. Not everybody gets offers to make a ton of money in trading, and certainly not everyone has a cushy job to leave in the first place. But the logic of my experience works at any scale. From someone who leaves a six-figure job and can borrow money from their rich parents, to guys have only two nickels to rub together. The guy working at Burger King who takes night classes to learn computer programming, or the woman who joins forces with a friend to start a food truck business. That’s being bold too, just on a smaller scale. In all these cases, you can take the safer path of quiet misery, or the bolder path that’s less certain but potentially much more rewarding, both financially and psychologically. How to be bold as an older person. Everything I’ve said in this chapter points to being bold when you’re young, but there are ways to be bold as an older person too. And those have to do with being brave enough to spend your hard-earned money. You have to have the courage to do the things I described in the Know Your Peak chapter. The courage to walk away from a career so that you can spend your remaining time doing what’s more fulfilling. People are more afraid of running out of money than wasting their life. And that’s got to switch. Your biggest fear ought to be wasting your life and your time, not am I going to have X number of dollars when I’m 80? What if I’m risk averse? I can understand the fear of risk because my mom is like that. She was a teacher working for the state and always wanted me to get a government job of some sort too. (Time 0:17:02)
  • Weigh Inaction Risk And Quantify Worst Case Scenarios
    • Prefer making bold moves earlier, but also evaluate the risk of inaction by comparing lost experiences to peace of mind.
    • Quantify worst-case scenarios and available safety nets to see downside is often smaller than feared. Transcript: Bill Perkins First, whatever level of risk you’re comfortable with, whatever bold moves you might contemplate for your life, you’re generally better off making those moves earlier in life. Again, that’s when you have the higher upside and a lower downside. Second, don’t underestimate the risk of inaction. Staying the course instead of making bold moves feels safe, but consider what you stand to lose. The life you could have lived if you had mustered the courage to be bolder. You’re gaining a certain kind of security, but you are also losing experience points. For example, realize that if you avoid certain risks, you will get 7,000 experience points instead of 10,000. That means you end up with a life that’s 30% less fulfilling. If you say that 30% less fulfillment is worth the peace of mind you get, well, that’s okay. My grandma, for example, wouldn’t have been able to sleep at night if she’d lived a bolder life. And I can’t fault her for that. How much risk you take on is your own personal choice. I just want you to be aware of the decision you’re making and the full consequences of that choice. Third, I’ll remind you that there’s a difference between low risk tolerance and plain old fear. Fear tends to take the actual risk and then blow it out of proportion. If you’re prone to knee-jerk fear reactions to taking bold moves, think through the worst-case scenario. When you consider all the safety nets you’ve got in your life, from unemployment insurance provided by your job, to private insurance you can buy against any kind of disaster, to good Old-fashioned help from your family, the worst-case scenario is probably not as bad as you think. (Time 0:19:52)
  • Aim To Die With Zero To Prioritize Memories Over Savings
    • ‘Die With Zero’ is an aspirational target that shifts behavior from hoarding wealth to maximizing life experiences and memories.
    • Perkins argues aiming for zero won’t be exact but moves your autopilot toward living fully now. Transcript: Bill Perkins Conclusion. An impossible task, a worthy goal. I’ve given you an impossible task, to die with zero. You can follow every rule in this book. You can closely track your health and life expectancy. And you can recalculate your financials every day. Yet, you’re not going to hit exactly zero. When you take your last breath, you might still have a few dollars in your pocket and maybe even hundreds more in the bank. So technically, you will have failed to die with zero. That’s inevitable. And it’s okay. Why? Because that goal will have done its real job of pushing you in the right direction. By aiming to die with zero, you will forever change your autopilot focus from earning and saving and maximizing your wealth to living the best life you possibly can. That’s why dying with zero is a worthy goal. This goal in mind, you are sure to get more out of your life than you otherwise would have. Millions of people go to church or temple every week trying to be like Jesus or Moses. Millions more try to emulate Muhammad. Most don’t even come close. And that’s okay. None of us is perfect. And even the most virtuous among us aren’t always kind, always wise, always courageous. But by pushing these ideals, we do move in the right direction. We become at least a little bit kinder, wiser, and more courageous. And so it is with this ideal of dying with zero, try as you might, you will never hit the target exactly, but with any luck, you will get closer than if you’d never tried. So go ahead, not only living your life to the fullest, but saving the only life you’ve got. I hope my message has at least jarred you into rethinking the standard and conventional approaches to living one’s life. Get a good job, work hard through endless hours, and then retire in your 60s or 70s and live out your days in your so-called golden years. But I still ask you, why wait until your health and life energy have begun to wane? Rather than just focusing on saving up for a big pot full of money that you will most likely not be able to spend in your lifetime, live your life to the fullest now. Chase memorable life experiences, give money to your kids when they can best use it, donate money to charity while you’re still alive. That’s the way to live life. Remember, in the end, the business of life is the acquisition of memories. So, what are you waiting for? (Time 0:22:21)
  • Spend While Healthy To Maximize Experience Value
    • Spend money while healthy: chase memorable experiences, give kids money when they can use it, and donate while alive.
    • Perkins frames life as acquisition of memories, urging immediate action over deferred gratification. Transcript: Bill Perkins Chase memorable life experiences, give money to your kids when they can best use it, donate money to charity while you’re still alive. That’s the way to live life. Remember, in the end, the business of life is the acquisition of memories. So, what are you waiting for? (Time 0:24:53)