Mark: The fable of the Ant and the Grasshopper taught us all a lesson: work hard, save for winter. But what if the ant is the one who loses? What if the ant works its whole life, saves a huge pile of grain, and then just... dies on top of it? Michelle: Huh. I’ve never thought of it that way. The grasshopper starves, but the ant never really lives. You’re taught from childhood that the ant is the hero, the responsible one. But you’re right, what’s the point of all that work if you never get to enjoy the harvest? Mark: That's the provocative question at the heart of Die with Zero by Bill Perkins. It’s a book that fundamentally challenges our most deeply held beliefs about money, work, and the purpose of life. Michelle: And Perkins is a fascinating character to be asking this. He's not some philosopher in an ivory tower; he's a billionaire hedge fund manager and a high-stakes poker player. He lives and breathes risk and reward. His perspective is shaped by a world where you make calculated bets, not just for money, but for a better outcome. Mark: Exactly. And he argues that most of us are playing the game of life all wrong. We're so focused on accumulating wealth—our net worth—that we forget to maximize what he calls our net fulfillment. Michelle: Okay, I’m intrigued. 'Net fulfillment.' That sounds a lot more inspiring than 'net worth.' But what does that actually mean in practice? Is it just about having more fun?

Mark: It’s deeper than just 'fun.' Perkins introduces this powerful idea he calls the 'memory dividend.' He says that when you spend money on an experience, you get the joy of the experience itself, but you also get to enjoy the memory of it for the rest of your life. That memory pays you dividends in happiness, storytelling, and identity, year after year. Michelle: A memory dividend. I like that. It’s like an investment that keeps paying out in a non-financial currency. Mark: Precisely. He tells this great story from his early days in New York. His roommate, Jason Ruffo, was making a tiny salary, something like $18,000 a year. One day, Jason announces he's taking three months off to go backpack through Europe. To fund it, he borrows money from a loan shark. Michelle: Oh boy. That sounds like the exact opposite of what any financial advisor would recommend. That’s a one-way ticket to financial ruin. Mark: That's what Perkins thought too! He was horrified. But Jason went. He had these incredible, life-changing experiences—he saw London, visited the Dachau concentration camp in Germany which deeply moved him, fell in love on a Greek island. He came back broke, but fundamentally changed. Years later, Jason said, "Whatever I paid, I feel it was a bargain because of the life experiences I gained. You can’t take those away." Perkins, on the other hand, had stayed, worked, and saved. And all he had to show for it was regret. Michelle: Wow. So Jason's memory dividends from that one trip probably outweighed years of small, incremental financial gains that Perkins made. Mark: They compounded over his lifetime. That’s the core idea. Your life is the sum of your experiences. The more you invest in them, the richer your life becomes. Michelle: I can see that. But that sounds great for a 20-something with no responsibilities. What about when you have a mortgage, car payments, and kids? Isn't being the responsible 'ant' the right thing to do then? You can't just go backpacking with a loan shark's money. Mark: That's a fair point, and Perkins addresses it. The value of experiences doesn't diminish with age; it actually changes. He tells another, much more personal story about his father. Towards the end of his father's life, his health was failing and he couldn't travel or do much. Michelle: A situation many families face. Mark: Right. So for his birthday, Perkins digitized a highlight reel from his dad's 1959 Rose Bowl-winning football season at the University of Iowa and put it on an iPad. His dad, who could barely move, would watch it for hours, reliving those moments of glory. He told Perkins it was the best gift he'd ever received. Michelle: That gives me chills. Mark: The insight Perkins had was profound: we all, in a sense, 'retire on our memories.' When your health is gone and you can't create new, active experiences, those memories—the dividends from your past investments—become your primary source of joy. If you wait too long to have those experiences, you might not be healthy enough to enjoy them, and you'll have fewer memories to retire on.

Michelle: Okay, so invest in experiences early and often. I’m on board with that. But the title of the book is Die with Zero. That’s a much more extreme proposition. It sounds terrifying. You’re supposed to aim to have your bank account hit zero the moment your heart stops? Mark: It is a terrifying thought, and that’s why it’s so powerful. Perkins clarifies it’s a guiding principle, not a literal command to bounce the check for your own funeral. The point is to shift your entire mindset. He argues that any money you have left over when you die represents wasted life. You exchanged precious hours of your one and only life for money that you never converted back into enjoyment, experiences, or impact. Michelle: Wasted life energy. That’s a heavy way to put it. But are people really leaving that much on the table? I feel like most people worry about not having enough. Mark: That’s the conventional wisdom, but the data is absolutely shocking. Studies from the Federal Reserve and the Employee Benefit Research Institute show that the vast majority of retirees don't spend down their savings. In fact, their net worth often increases in retirement. One study found that retirees with over half a million dollars had only spent down about 12% of it after two decades. A third of them actually grew their assets. Michelle: Wait, so they’re living more frugally in retirement than they need to, and their nest egg is just getting bigger and bigger until they die? Mark: Exactly. It’s a massive, widespread tragedy of underspending and unlived life. Perkins tells the story of his friend and colleague John Arnold, a legendary energy trader. Arnold was a genius and started his own hedge fund. His initial goal was to make $15 million and then quit to enjoy life. He even told Perkins, "If I’m still trading when I hit that, punch me in the face." Michelle: I have a feeling no one got to punch him. Mark: You guessed it. He hit $15 million. Then the goal became $25 million. Then $100 million. He eventually retired at 38, but with a net worth of over $4 billion. He had worked years past the point where the money could bring him any additional utility, driven by habit. He now faces the much harder problem of figuring out how to wisely give away this vast fortune. He completely overshot the runway. Michelle: That’s a problem most of us would love to have, but I see his point. He traded years of his youth for money he couldn't possibly spend. But this brings up the biggest objection I have, and I’m sure many listeners do too. What about the kids? This whole idea feels incredibly selfish. You're telling people not to leave an inheritance? Mark: This is the most controversial part of the book, and where it gets really interesting. Perkins argues that the traditional way we think about inheritance is completely backward and, in his words, "uncaring." Michelle: Uncaring? How is leaving your children money uncaring? Mark: He calls it the three Rs: giving a Random amount of money at a Random time to Random people, because you don't know who will be alive or what their needs will be. He says if you truly care, you should give with intention. The data shows the peak age for receiving an inheritance is around 60. But the time when money has the most impact on someone's life is between 26 and 35. That’s when they’re buying a first home, starting a family, or launching a business. A $50,000 gift at age 30 is life-changing. At age 60, when you’re already established, it’s just a nice portfolio bump. Michelle: That makes so much sense. You’re giving them the resource when their need—and their ability to use it for life experiences—is at its peak. Mark: Precisely. He shares the story of a woman named Virginia Colin, whose parents were well-off but waited to pass on their wealth. Virginia struggled for years as a single mom on the edge of poverty. She finally received her inheritance of $130,000 when she was 49. It was welcome, but she said it would have been a world of difference 20 years earlier when she was scrambling to raise her kids. Perkins’s point is this: your real legacy isn’t the number in a bank account after you’re gone. It’s the experiences you share with your loved ones and the support you give them when it matters most.

Michelle: Alright, I'm intrigued, but still a bit terrified. The philosophy is compelling, but it feels like you’re walking a tightrope without a net. How does anyone actually plan for this without messing up and running out of money too soon? Mark: This is where the book moves from philosophy to a practical framework. The first tool he offers is something he calls 'Time-Bucketing.' Michelle: Time-Bucketing. Is that like project management for your life's fun stuff? Mark: That’s a great way to put it! He says a traditional bucket list is flawed because it’s reactive—it’s a list of things you want to do before you die, often created when you’re older and facing mortality. Time-bucketing is proactive. You divide your life into five or ten-year blocks—your 20s, 30s, 40s, and so on—and you start plotting out the key experiences you want to have in each of those buckets. Michelle: Why the buckets? Mark: Because some experiences are better suited for certain ages. Hiking the Inca Trail is probably best done in your 30s or 40s, not your 70s. Taking a year off to travel is easier in your 20s than your 50s. By bucketing, you force yourself to think about the timing and to plan for these experiences, ensuring you don't delay them until it's too late. It creates a tangible roadmap for your life's fulfillment. Michelle: I like that. It turns a vague wish list into an actual plan. But planning is one thing; having the courage to act on it is another. Many of these things require taking risks—quitting a job, spending a lot of money. Mark: And that’s the final piece of the puzzle: being bold, but not foolish. Perkins argues you should take your biggest risks when you have the least to lose. He calls this 'asymmetric risk'—situations where the potential upside is massive, and the potential downside is minimal. Michelle: Like his roommate borrowing from a loan shark. The downside was debt, but the upside was a lifetime of memories. Mark: Exactly. And the best example he gives is Mark Cuban. Before he was a billionaire, Cuban moved to Dallas after college with nothing. He slept on the floor of a three-bedroom apartment with five other guys. He took a job as a software salesman and was fired for defying his boss to go close a sale. Instead of panicking, he saw it as an opportunity. He had nothing, so he had nothing to lose. He started his first company, MicroSolutions, right then and there. Michelle: And the rest is history. His point is that when you're young and have no assets, your downside is basically... sleeping on a floor again. Which you can recover from. The upside is building a multi-million dollar company. Mark: That’s the asymmetry. For someone in their 20s, the risk isn't taking a chance on a new career or moving to a new city. The real risk is not taking it, staying in a safe but unfulfilling path, and regretting it for the next 40 years. The risk of inaction is often the biggest risk of all.

Michelle: So when you pull it all together, this isn't really a personal finance book in the traditional sense. It's a philosophy book that uses money as a lens to talk about how to live a more intentional life. Mark: Exactly. The ultimate point is that your life is the sum of your experiences. Perkins argues that we're all, in a way, energy-processing units. We spend our life energy—our time and health—to acquire money. The entire purpose of that money is to be converted back into life experiences. The question he forces you to ask is, are you converting that energy back into a life well-lived, or are you just letting it sit in an account until the power goes out for good? Michelle: That’s a powerful reframe. It makes hoarding cash feel less like security and more like a waste of a finite resource—your own life. So maybe the first step for listeners isn't to create a new budget, but to just do a mini time-bucket exercise. Write down one big, meaningful experience you want to have in the next five years. Mark: I love that. Not a financial goal, but an experiential one. And then you can work backward to figure out how to fund it. It puts the 'why' before the 'how.' Michelle: And it makes the saving feel purposeful, not like deprivation. You’re not saving from your life; you’re saving for your life. Mark: That's a perfect way to put it. And we'd love to hear what that experience is for our listeners. Share it with us on our social channels. What's the one thing you’re going to stop delaying? Michelle: Let's fill up those time buckets. Mark: This is Aibrary, signing off.