Die Broke, Annuities, and Tax-Free Retirement Income Artwork

Divorce the IRS

Welcome to Divorce the IRS, the Retirement Income Planning Podcast—built for people who want to pay the least amount of taxes possible and create retirement income that actually lasts. Inspired by Jimmy Miller’s bestselling book Divorce the IRS, this show takes you behind the scenes of the tax rules, retirement strategies, and planning decisions that can quietly determine how much of your money you keep.

The truth is, taxes aren’t just “something you deal with later.” The U.S. tax code is massive, confusing by design, and full of traps that can hit hardest right when you need your money most. From 401(k)s and IRAs to Social Security and Medicare, many common “smart moves” can turn into expensive surprises—like required minimum distributions, Medicare surcharges, the widow’s penalty, and other retirement tax time bombs most people don’t see coming until it’s too late.

With 20+ years of experience as a global wealth manager, Jimmy breaks these topics down in a clear, practical way—so you can plan proactively, avoid unnecessary taxes, and build a retirement where your delayed gratification finally pays off. Subscribe so you never miss an episode, and remember: this podcast is for general education only and isn’t legal, tax, or investment advice—always consult a qualified professional for guidance specific to your situation.

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Divorce the IRS

Die Broke, Annuities, and Tax-Free Retirement Income

July 15, 2026 • James Miller

0:00 | 6:00

In this episode of the Divorce the IRS Podcast, Jimmy Miller discusses a retirement philosophy that has become increasingly popular: die broke, also known as die with zero.

The idea behind this strategy is to maximize retirement income and enjoy more of your money during your lifetime, especially when leaving a financial legacy is not a major goal. Jimmy explains why the concept can make sense in theory, but why trying to personally spend your portfolio down to zero without guarantees can create serious risks.

Jimmy also explains how the die broke philosophy can work together with the Divorce the IRS framework when lifetime income annuities are used properly, especially inside Roth IRA accounts.

In this episode, Jimmy discusses:

What the die broke or die with zero philosophy means
Why the concept appeals to many retirees and future retirees
The danger of becoming too frugal and never enjoying your money
Why aiming for exactly zero can be risky without the right structure
How lifetime income annuities can support a die broke strategy
Why guaranteed income may help reduce retirement stress
The risk of running out of money before running out of life
How annuities can allow retirees to spend both growth and principal
Why Roth IRA annuities can create tax-free lifetime income
The importance of understanding annuity rules before purchasing one
How fixed index annuities may help address inflation concerns

Jimmy also shares why dying broke can be a reasonable goal for some people, but only when the plan is built carefully and includes the right guarantees. When structured correctly, the goal is not simply to spend everything. It is to create a retirement income strategy that allows you to enjoy your money with confidence while reducing the risk of outliving it.

SPEAKER_00 0:01

Welcome to the Divorce the IRS Podcast, the retirement income planning podcast designed specifically for those who want to pay the least amount of taxes possible and build a retirement income that lasts. Inspired by the best-selling book, Divorce the IRS, you get to go behind the scenes with financial planner, author, and speaker Jimmy Miller. Learn how to set yourself up to pay the least amount of taxes in retirement when you'll need your money the most. And now, here's your host, Jimmy Miller.

SPEAKER_01 0:27

Welcome. Welcome to episode 29 of the Divorce the IRS podcast. Today, we're going to discuss another retirement philosophy, one that is becoming more and more popular, and that I get a lot of questions about. That philosophy is called die broke or die with zero. Let's dive right in. There are several books out there these days about dying broke and bouncing a check the day that you pass away. This financial strategy is generally about maximizing your retirement income to the fullest possible. If there aren't any legacy considerations, and for many people there are none, it can also be about spending more before retirement and not saving as much. Books like Die With Zero attempt to make the case that you should spend more while you're young, healthy, and can enjoy your money more fully. I'll admit, I love the core intention behind that message. It pushes back against the toxic, hyperfrugal mindset that plagues so many savers. While the philosophy sounds beautiful on paper, when you look at how human psychology and actual life play out, shooting for exactly zero can be a deeply flawed strategy if done incorrectly. Done the right way, though, divorcing the IRS and dying broke can easily go hand in hand. They are complementary ideas, I would say, as both are really about maximizing how much income you have in your retirement years. The successful concepts of dying broke usually involve guaranteed lifetime income annuities. This is when an insurance company takes your money in exchange for a guaranteed stream of income that you can't outlive, no matter how old you become. When you are done, the income is also done. With these strategies, there is no chance that your income will run out before you do. There are even studies showing that people who utilize annuities in retirement for income actually live longer and are happier than those who don't use annuities. There is just something about living for that next direct deposit into your bank account that keeps people going. Combined with the fact that those with annuity income don't have to worry about things like the stock market or running out of money allows them to have less stress in retirement as well. Now trying to die with zero by personally managing your money to zero and attempting to reach that point at the same time you pass away can be disastrous. Running out of money before you run out of life is one of the biggest worries that retirees face today. Spending too much early on in retirement can lead to real regret later on, as well as not having enough money for things like comfort care if you get sick later in life. So if you are going to attempt to die broke, then make sure you do it with the guarantees necessary to make it work well for you and use annuities from big, well-established annuity companies. These types of products, if purchased correctly, can increase the amount of income you can receive in retirement because they plan the spend down of both your growth and principal. Many people, not wanting to invade their principal, only live on the interest or growth and dividends from their nest egg. And this is fine and it definitely has its benefits, but it won't get you as much income in retirement as planning to spend both your growth and your principal like an annuity will. Spending your principal down to nothing in retirement can only really be done safely within the context of an annuity, since the risk is shifted to an insurance company and your income will remain even if or once your principal is gone. To make the two concepts of divorce CIRS and DIPROKE work together, all you need to do after following the concepts in this podcast is purchase those lifetime income annuities within your Roth IRA accounts. It's no problem at all to have a Roth IRA annuity. And when you do this, all the income that comes from the annuity company over your lifetime will be tax free, just the same as if you took the income out of your Roth IRA at a brokerage or investment company. The tax rules remain the same for both. It's important to understand the annuities you are purchasing though and how they work if you're following a dye broke strategy. Annuities can be complex and have many rules about how they pay out and how the investments within them work as well. Revisit the recent episode about how dividends work inside most annuities so that you have a proper understanding. Utilizing a more modern annuity, like a fixed index annuity, will usually be your best bet. These newer annuities may also have the opportunity for your income to increase and keep up with inflation over time. This becomes a very important issue over a two-person 30-year retirement as inflation erodes the real value of your income over time and what you can actually purchase with it. My dad always likes to joke about this subject, my inheritance, and I've heard him say on more than one occasion that you don't ever see the Brinks truck in the funeral procession. And regardless of how you feel about leaving a legacy after you're gone, dying broke can be a reasonable goal for some people.

SPEAKER_00 5:23

Want even more ideas, tools, and resources on how to navigate through financial life? Check out all the resources on the Divorce the IRS website at divorce-the-IRS.com or the Bayob Wealth website at bayobwealth.com and subscribe to the blog to stay up to date on issues affecting retirement income planning. Don't forget to subscribe to the podcast so you never miss an episode. Bayob Wealth and Bayabot Wealth Abroad are DBAs of Bayob Wealth LLC, a Florida registered investment advisor. This podcast is designed for general education purposes only and shouldn't be taken as legal investment or tax advice. You should seek out a qualified tax professional or licensed financial advisor to determine what is best for your personal situation.