What you don't know CAN hurt you! Retirement is the most expensive purchase you'll ever make and, because you only get one shot, you better get it right. This show is dedicated to helping retirees and Baby Boomers learn what they need to know so they can make informed decisions and retire successfully. And best of all, we make it understandable! If you want to learn how to avoid some of the more common mistakes I've seen retirees and Boomers make over the last two decades, tune in; and if you like what you hear, kindly consider giving us a review. It helps our show reach more people like you.
Many retirement plans are built with a "set it and forget it" mindset. As long as account balances look steady, it's easy to assume everything is working. But retirement doesn't work that way.
In this episode, we talk about why the biggest risk in retirement isn't always a market drop. It's the false sense of security that comes from calm markets and stable-looking statements. Real stability isn't tested when things are quiet. It's...
The "3-bucket strategy" is one of the most commonly used frameworks in retirement planning. Growth, conservative, and cash buckets may sound simple, but the rules governing how they work change dramatically once you retire.
Most traditional 3-bucket strategies are built around one core assumption: that retirement income will be generated by selling assets. The cash bucket is meant to be spent down, the conservative bucket tapped ne...
January has a way of restoring structure to daily life. The holidays fade, routines return, and expenses begin to arrive with predictable regularity. While working, that structure was anchored by a paycheck which was showing up consistently and making life feel manageable.
Retirement quietly removes that framework. And if you're not careful, it replaces freedom with uncertainty.
In this episode, we explore the critical difference b...
Happy New Year to all our followers, and welcome to Season 7 of the podcast!
Every January carries the promise of progress. The calendar flips, routines reset, and we make the assumption that something meaningful has changed - simply because the date has. But time passing is not the same as progress being made. Our first podcast of 2026 explores the dangerous comfort of automatic optimism and why unchanged habits, outdated strategi...
Most retirement conversations obsess over account balances - how much you've saved, how your portfolio performed, whether you've hit a "number." But retirement doesn't work like a scorecard. It works like a paycheck.
In this episode, we reframe retirement planning around the question that actually matters: How much reliable monthly income can your investments generate, and can you use it confidently? Take too much, and you risk run...
Most retirement conversations revolve around numbers - account balances, returns, tax brackets, required minimum distributions. But after working with retirees for more than a quarter of a century, one truth has become clear: emotional wealth matters more than financial wealth.
In this episode, we explore why peace of mind, confidence, and income stability ultimately define a successful retirement far more than hitting a specific ...
This episode delivers a deep-dive Q&A on the choices that shape a secure retirement. We break down whether to roll a 401(k) into an IRA, when Roth conversions are worth it, and why bonds, when used correctly, can provide essential income.
Discover how to build a portfolio that withstands loss, inflation, and the risk of running out of money, and learn a smarter way to rebalance using a function-based approach to investing.
We also...
Everything might look perfectly fine on the surface, but retirement is full of threats that can grow quietly in the background until they're suddenly too big to ignore. In this week's episode, we dive into the hidden pitfalls that can disrupt even the strongest retirement plans: relying too heavily on the stock market, rising living or health care costs, Required Minimum Distributions pushing you into a higher tax bracket, and more...
Thanksgiving is a perfect reminder that great outcomes never just "happen." A successful holiday meal takes planning, preparation, and thoughtful timing - and retirement is no different.
In this episode, we break down why intentional planning matters, why timing affects everything, and why scrambling last-minute (whether at 55, 65, or the week before retirement) only creates stress. And more importantly - why it's never too late to...
The holiday season is here, and while festivities take center stage, now is the critical moment to make smart financial decisions that set up next year (and your long-term retirement) on the right track.
In this week's podcast, we break down the key year-end actions retirees shouldn't overlook: Required Minimum Distributions, strategic withdrawals, potential Roth opportunities, rebalancing investments, reviewing charitable gifts, ...
Most people think retirement success depends on the stock market, but one of the biggest factors that determines whether your money lasts isn't what you invest in, it's when and how you withdraw it.
In this episode, we break down the 3 key tax levers that can dramatically impact your lifetime retirement income: Required Minimum Distributions, Roth Conversions, and Social Security. These income sources are deeply interconnected, an...
Investing isn't hard because of math; it's hard because of emotion. When the market's up, confidence soars and it feels easy to believe the good times will keep rolling. But when the market dips, fear takes over, and that emotional roller coaster can lead to costly mistakes.
In this episode, we explore the critical difference between reacting and reasoning, between emotional investing and intentional planning. You'll learn how to:
...
When most people hear the words "estate plan", they picture the ultra-wealthy - people with vacation homes, mansions, and millions in the bank. But here's the truth: estate planning isn't about how much you have, it's about what happens to your loved ones when you're gone.
In this episode, we'll break down what an estate plan really is, and why everyday families in California need one. If you own a home or have more than $184,500 i...
The calendar is winding down, and while most people are focused on the holidays coming up, the smart ones know this is also crunch time for tax planning. Once December 31st hits, many of your opportunities to save on taxes disappear, so now is the moment to act.
In today's episode, I'm walking you through eight smart, year-end strategies that can help lower your tax bill and keep more of your hard-earned money where it belongs - wi...
One of the most common questions we hear from retirees is, "How much income can I safely take from my portfolio?". It sounds simple - but it's one of the most difficult questions to answer in retirement planning. If you withdraw too much, you risk running out of money before you run out of life; if you take too little, you might live well below your means and miss out on experiences such as travel or special moments with family tha...
The strategies that built your wealth aren't always the same ones that will help you keep it. In this episode, we explore why financial approaches that worked so well during your working years can actually work against you in retirement. You've spent decades in accumulation mode, adding to your accounts month after month; but once you retire, the script flips. You're no longer the contributor; you're the withdrawer.
We'll talk abou...
Have you ever sat down with a financial advisor and felt like they were speaking a foreign language? Too often, industry jargon gets in the way of clarity. What sounds like everyday terms to advisors - "25 basis points" instead of "0.25%," "alpha and beta" instead of "risk and return," or "Monte Carlo simulations" when talking about withdrawal strategies - can leave the average person confused and frustrated ("are we gambling here?...
They say rules are meant to be broken - but in retirement planning, some rules are designed with exceptions that can actually work in your favor. In this episode, we explore where flexibility exists in the retirement system:
- IRA & Roth IRA: Special contribution and RMD exceptions that could save you money.
- 401(k)s: When you can contribute or withdraw outside the standard rules.
- Social Security: Situations where exceptions unl...
With so many listener questions pouring in lately, it was time for another Q&A session. In this episode we tackle the most pressing retirement topics on your mind:
- Social Security: How to maximize your benefits and avoid costly mistakes.
- Required Minimum Distributions (RMDs): What the new rules mean for your withdrawals.
- Inherited IRAs: The latest changes that could reshape your estate planning.
- Annuities: Where they fit (a...
Many of the "golden rules" of retirement no longer shine. The 4% withdrawal rule, the "set it and forget it" investment strategy, and even long-trusted programs like Social Security and Medicare aren't as reliable as they once were.
In this week's podcast, we unpack why these outdated approaches could put your financial future at risk, and more importantly, what you can do instead. You'll learn the new realities of retirement plan...
If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.
Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com
It’s the history of business. How did Hitler’s favorite car become synonymous with hippies? What got Thomas Edison tangled up with the electric chair? Did someone murder the guy who invented the movies? Former Planet Money hosts Jacob Goldstein and Robert Smith examine the surprising stories of businesses big and small and find out what you can learn from those who founded them.
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The official podcast of comedian Joe Rogan.