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How to Die With Zero | Bill Perkins artwork

How to Die With Zero | Bill Perkins

Your Money Guide on the Side

July 14, 2025

And in case you missed it, check out last week's episode of Your Money Guide on the Side where we answered the question, How do I beat the stock market? Is Future Planning Ruining Your Future? What if your financial advisor told you to spend your money now? To give away your inheritance early?

Speakers Bill Perkins, Tyler Gardner

TopicsInvestingBusinessEntrepreneurship

Bill Perkins (0:00)

I'm not an anti-delay gratification person. I'm a think about the context of your situation, and what experiences do you want when? Life is now, life is urgent. Would you rather have one ski trip in your 30s, or let's say two and a half ski trips in your 50s? What is the money for?

Tyler Gardner (0:21)

Hello, friends. This is Tyler Gardner welcoming you to another episode of Your Money Guide on the Side, where it is my job to simplify what seems complex, add nuance to what seems simple, and learn from and alongside some of the brightest minds in money, finance and investing. So let's get started and get you one step closer to where you need to be. Today's guest is someone whose work hit me harder than I expected. Bill Perkins is the author of Die With Zero, a book that came recommended to me by so many people I trust that I finally had to pick it up, and not only did I pick it up, but to be honest, at this point, I think I've read it five times. Because throughout my life, I've been a great saver and investor. I followed all the rules. Save early, save often, invest in low-cost index funds, you know the deal. But what I hadn't realized until reading Bill's book was that the years were indeed starting to pass, and I'm still not quite finding how to balance my investing with my healthy spending on every day experience. Bill Perkins doesn't just question the wisdom of saving for some day. He challenges it head on. Die With Zero is about optimizing your life while you can, turning money into meaningful experiences, and measuring wealth in time well spent, not just dollars saved. And Bill brings more than theories to the table. He's been a hedge fund manager, a high stakes poker player, an entrepreneur, and a world traveler to say the least. Someone who knows what it means to manage risk and reward in the real world, not just on spreadsheets. In this conversation, we explore why saving too much can be one of the biggest mistakes you ever make, how to reframe money through the lens of time and meaning, what traditional financial advisors, and many of us, get wrong about retirement and estate planning, and how you can start designing a deliberate and action-oriented life that you actually get to live before it's too late. So without further ado, a conversation I have been waiting so long to have with Bill Perkins.

It's funny, you're one of the only books that has been recommended to me consistently over the last three years by every demographic to which I connect. It's pretty awesome, man. Seventy-year-olds are like, have you read Perkins? And then my 20-year-old connection is like, dude, you got to read Bill Perkins. I'm like, this is awesome. You hit on something pretty deep, which I'm sure you know by now. But one of the things that obviously drew me to Die With Zero is there's an incredibly cool core of contrarian thinking to a lot of the nonsense we hear throughout life about deferring joy and just letting all the money sit, and letting our lives and bodies break down along the way. You made a comment early in Die With Zero that you kind of understood this, and I'll even say kind of like this wisdom when you were at the University of Iowa, and you were majoring in engineering, and you realized early that you didn't necessarily want to go the traditional route of working for a company like IBM. Could you just share a little bit about how you came to that realization so early, whereas it takes so many people decades, if not their entire lives, to figure out, they want to try to kind of break the traditional money script or job script?

Bill Perkins (3:53)

Yeah, I think there was a couple of things that happened. I think I was leaning towards that or was in me, and I was going to engineering because it was like, you need to find something to do, and I was interested in engineering, but I wasn't interested in engineering enough to study real hard and get good grades, right? I was interested enough to go and learn, this is interesting, maybe show up for the test, maybe not, play football, chase girls, that type of thing. It just seems so like death to me, but something that needed to be done, like you need to get a job. I was having a discussion, I don't even know what the discussion was about with this other football player named Dwight Sistrunk. He came back at me, he was like, listen Perkins, I'm not like you, I don't want a white picket fence in a house and then a job and two car garage, whatever, I want a different life. I just thought it was odd at the time. I was like, who doesn't want that? That's kind of like every Chevy Chase movie I've seen. You know what I mean with Steve Martin, they got the nice house. How do I get a house like that?

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