Money for The Rest of Us

Investment help and financial guidance for the rest of us.

  • Podcast
  • Guides
        • Asset Classes

        • A Complete Guide to Investing in I Bonds and TIPS (2025)
        • A Complete Guide to Equity REIT Investing
        • A Complete Guide to Mortgage REIT Investing
        • A Complete Guide to Investing in Gold
        • A Complete Guide To Investing In Convertible Bonds
        • Investing in Bitcoin, Oil, and Volatility ETFs
        • Carbon Investing and its Effect on Climate Change
        • Farmland Investing
        • The Opportunity and Risk of Frontier Markets
        • Investment Vehicles

        • A Complete Guide to Investment Vehicles
        • How to Invest in Closed-End Funds
        • What Are SPACs and Should You Invest in Them?
        • Money and Economics

        • A Complete Guide to Understanding and Protecting Against Inflation
        • Understanding Web3 Investing
        • Strategy

        • Why You Should Rebalance Your Portfolio
        • What Is Risk vs Uncertainty?
        • Tail Events and Tail Risk
  • Resources
        • General Resources

        • Topic Index
        • Glossary
        • Most Influential Books
        • Member Tools

        • Member - Getting Started Guide
        • Asset Allocation and Portfolio Tools
        • Current Investment Strategy Report
        • All Investment Conditions Reports
        • Strategic and Adaptive Model Portfolios
        • Member Tools and Downloads
        • Member Resources

        • Plus Premium Episodes
        • Submit A Question to the Plus Podcast
        • Member Forums
        • David’s Current Portfolio
        • David's Portfolio Trades
        • Courses

        • Investing in Closed-End Funds
  • Members
  • Join
  • Log In
You are here: Home / Podcast / 446: Die with Zero: Why You Should Start Spending Now

446: Die with Zero: Why You Should Start Spending Now

September 6, 2023 by David Stein · Updated September 25, 2023

How to balance saving, investing, and spending for a fulfilling life. Why you will probably reach your peak net worth sooner than you think and should start drawing down your nest egg earlier. Why we can’t optimize for a fulfilling life but can still have one.

Topics covered include:

  • How to estimate how much to spend from your retirement assets so you die with zero
  • What is time bucketing, and why it doesn’t work for everyone
  • How to balance the fear of making a change with the fear of missing out
  • The difference between making deliberate choices and maximizing our experiences

Show Notes

Die with Zero: Getting All You Can with Your Money and Your Life by Bill Perkins

The Pathless Path: Imaging a New Story for Work and Life by Paul Millerd

Four Thousand Weeks: Time Management for Mortals by Oliver Burkeman 

Anderson Cooper Is Still Learning to Live With Loss by David Marchese—The New York Times

Episode Sponsors

Monarch Money – Get an extended 30-day free trial

NetSuite – Get your free KPI checklists

Become a Better Investor With Our Investing Checklist

Become a Better Investor With Our Investing Checklist

Master successful investing with our Checklist and get expert weekly insights to help you build your wealth with confidence.

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Related Episodes

32: Die Broke

278: You Have Permission to Spend

437: How to Live Like You Are Already Retired

Transcript

Welcome to Money for the Rest of Us. This is a personal finance show on money, how it works, how to invest it, and how to live without worrying about it. I’m your host, David Stein. Today is episode 446. It’s titled “Die With Zero: Why You Should Start Spending Now.”

Two Personal Finance Books

I recently finished two books that seem to resonate with the personal finance community. They have sold well. The books have been recommended to me; I’ve seen them on social media. The first is Die With Zero: Getting All You Can With Your Money and Your Life by Bill Perkins. The second is The Pathless Path: Imagining a New Story for Work and Life by Paul Millard. 

I’ll admit, I was reluctant to read them. I assumed Die With Zero was about annuities, something we have covered numerous times on the show, including Episode 32, which was titled “Die Broke.” The Pathless Path had a more appealing title, but it felt like something I’ve already been on for more than a decade, and I wasn’t sure how helpful it would be.

Both Perkins and Millard have taken unconventional paths. Perkins is in his 50s; he was a successful energy trader. He’s still a hedge fund manager, a Hollywood film producer and spends time at high stakes tournaments playing poker. Paul Millard is younger. He’s in his 30s, he’s an independent writer, freelancer, coach, is not financially independent at this point. Perkins obviously is, although he says he’s not a billionaire. But it sounds like he’s very wealthy because he said he was one of the most successful energy traders in history.

Both books provide insights on answering this question. I’ll use Perkins’ phrasing of the question: “What is the best way to allocate our life energy before we die?” Perkins was trained as an engineer, so he sees his question as an optimization problem. How to maximize fulfillment while minimizing waste. And the problem he says we’re trying to solve is total life enjoyment. It’s such an optimization problem in his mind he’s developed an app. 

And I’ve not used the app, but he talks about different experiences can have different experience points, because he believes the goal is to maximize our fulfillment across our lifespan by having experiences. And it’s figuring out the right balance between earning money and then spending that money on experiences. And because in his mind it’s a complex optimization problem, that’s why he developed an app. 

Is Life an Optimization Problem?

I disagree. I believe we should strive to achieve fulfillment in our life, but I don’t see it as an optimization problem. When I hear the word optimization, even within investing, I tend to pull back, because there’s so many uncertainties. There isn’t a formula to have a fulfilling life. There isn’t an optimal answer.

Perkins believes the way that we maximize our fulfillment is by achieving the biggest peaks through a combination of our time and money. And then by investing in these experiences, we’ll have long-lasting memories that we can reflect on even as our health declines. And he calls this a memory dividend, that essentially our experiences and memories compound over time.

He is so focused on optimization that he says he has an app on his phone that shows how many days, weeks, even hours, I suspect until he’s expected to die if he dies at his actuarial life expectancy. I find that appalling. But I’m not an engineer, and that’s fine that he finds that app useful.

As a Money For the Rest of Us Plus member, you are able to listen to the podcast in an ad-free format and have access to the written transcript for each week’s episode. For listeners with hearing or other impairments that would like access to transcripts please send an email to team@moneyfortherestofus.com Learn More About Plus Membership »

Ready to get serious about your investing?

Access professional-grade portfolio tools, training, and a community to help you stay on track, tune out the noise, and grow your wealth with confidence.

Learn How

Filed Under: Podcast Tagged With: Perkins (Bill), retirement, retirement spending, spending

Contact | Team | Topic Index


Darby Creek Advisors LLC
P.O. Box 68544 • Tucson, AZ • 85737

Copyright © 2025 • Disclosures, Privacy Policy, and Cookie Policy • Site by Tempora

Manage Cookie Consent

We use cookies to optimize our website, marketing, and services. 

Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
Manage options Manage services Manage {vendor_count} vendors Read more about these purposes
View preferences
{title} {title} {title}
Manage Cookie Consent
We use cookies to optimize our website, marketing, and services. We never sell users' data.
Functional Always active
The technical storage or access is strictly necessary for the legitimate purpose of enabling the use of a specific service explicitly requested by the subscriber or user, or for the sole purpose of carrying out the transmission of a communication over an electronic communications network.
Preferences
The technical storage or access is necessary for the legitimate purpose of storing preferences that are not requested by the subscriber or user.
Statistics
The technical storage or access that is used exclusively for statistical purposes. The technical storage or access that is used exclusively for anonymous statistical purposes. Without a subpoena, voluntary compliance on the part of your Internet Service Provider, or additional records from a third party, information stored or retrieved for this purpose alone cannot usually be used to identify you.
Marketing
The technical storage or access is required to create user profiles to send advertising, or to track the user on a website or across several websites for similar marketing purposes.
Manage options Manage services Manage {vendor_count} vendors Read more about these purposes
View preferences
{title} {title} {title}