Your Successful Retirement

Hosted by Dennis O'Keefe

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Episodes

155

Latest episode

Aug 2026

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EN-US

About the show

Discover the secrets to a successful retirement with Dennis O’Keefe, a seasoned CERTIFIED FINANCIAL PLANNER™ with over 30 years of expertise. Whether you’ve been retired for years, are on the verge of retirement, or are wondering how to plan for your “some-day” retirement – this podcast is your go-to guide. Gain exclusive strategies tailored to optimizing your retirement benefits, hear real-life stories from retirees, and absorb invaluable wisdom from our guest leaders.

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60 recent

September 10, 202625 min

How to Buy Your Next Car Without Overpaying (Ep. 143)

Thinking about buying a car? It can feel overwhelming, especially when prices, financing, trade-offs, and dealership tactics all compete for your attention. How do you know you’re paying a fair price, and what steps can help you avoid expensive mistakes before you sign? In this episode, Dennis O’Keefe shares practical strategies to help you make more confident car-buying decisions. He explains why keeping your current vehicle longer can often save more than upgrading, how thorough research changes negotiations, considerations when evaluating a lease, and why buying used may offer meaningful advantages. Dennis also walks through negotiating over the phone, comparing total ownership costs instead of monthly payments, and researching rebates before stepping into a dealership. Key takeaways: Why keeping your current vehicle longer can often reduce long-term ownership costs and financial stress. How researching pricing, reliability, recalls, and ownership costs changes your buying position. What lease agreements often hide beyond the advertised monthly payment and why it matters. Why buying a used vehicle can reduce depreciation and avoid early ownership headaches. How negotiating remotely and verifying incentives helps compare offers more accurately. And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

August 27, 20265 min

Should You Contribute To Your 401(k) On a Roth Basis?

A Roth 401(k) can be a powerful retirement savings tool, but is it the right choice for everyone? In this YSR FAQ episode, Dennis O’Keefe discusses how Roth 401(k) contributions work and the factors that determine whether they make sense for your situation. The conversation explores current versus future tax brackets, the benefits of tax-free withdrawals in retirement, and why age can play a major role in the decision. Dennis also explains the importance of understanding tax rules and why younger investors often have more to gain from Roth contributions. If you’ve been wondering whether to save on a traditional or Roth basis inside your workplace retirement plan, this episode offers practical guidance to help evaluate the tradeoffs. Key takeaways: How Roth 401(k) contributions work The role tax brackets play in the decision Why younger savers often benefit more from Roth accounts The five-year Roth rule Factors to consider before making a change And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

August 27, 20266 min

How Much Money Do I Need For Retirement?

One of the most common retirement questions is also one of the hardest to answer: How much money is enough? In this YSR FAQ episode, Dennis O’Keefe explains why there is no universal retirement savings target and why your spending habits matter far more than a simple rule of thumb. Dennis shares a real-life example of two workers with dramatically different retirement account balances and reveals why the person with less money was actually in a better position to retire. He also walks through how retirement income, pensions, Social Security, debt obligations, and lifestyle choices all factor into the equation. If you’re trying to determine whether you’re financially ready for retirement, this episode highlights the importance of understanding your true spending needs before relying on generic retirement benchmarks. Key takeaways: Why retirement savings rules of thumb can be misleading The difference between income and spending How pensions and Social Security affect retirement readiness A simple way to estimate your retirement spending needs And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

August 13, 202626 min

How to Filter Market Noise and Focus on What Really Matters

Trying to predict the market can feel overwhelming when headlines, opinions, and daily volatility are everywhere. How do you separate meaningful economic signals from distractions? What information actually helps you make better financial decisions over the long term? In this episode, Dennis O’Keefe shares why market predictions are often little more than educated guesses and explains how he evaluates the economy through practical observations and reliable data instead of media headlines. He explores why consumer sentiment can be misleading, how job reports should really be interpreted, and why everyday experiences sometimes reveal more than breaking news. The conversation offers a calmer way to think about investing and long-term financial decisions. Key takeaways: Why trying to predict the market is often less reliable than many people believe How media incentives can distort the financial information people consume every day Why consumer sentiment often lags behind what’s really happening in the economy What everyday observations can reveal about economic trends before headlines do How to interpret employment reports beyond the headline job numbers And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

July 23, 20267 min

What Is a Trust?

What is a trust, and why do so many families use them in estate planning? In this YSR FAQ episode, Dennis explains the basics of revocable living trusts and how they help simplify estate settlement while avoiding probate. This conversation covers how trusts are structured, how assets are transferred into a trust, and why many people use trusts to help manage property, investment accounts, and inheritance instructions. Dennis also explains the difference between trustees and executors, as well as common mistakes people make after setting up a trust, including forgetting to properly retitle assets. If you’ve ever wondered whether a trust might make sense for your family or what actually happens when property is placed inside one, this episode provides a practical overview in plain language. Key takeaways: What a revocable living trust is How trusts help avoid probate Why assets must be retitled correctly The role of a trustee And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

July 23, 20266 min

Should I Put My House in an Irrevocable Trust?

Should you place your house into an irrevocable trust? In this YSR FAQ episode, Dennis explains why irrevocable trusts can become far more complicated than many people expect. This conversation covers why families consider irrevocable trusts for nursing home or Medicaid planning, along with the long-term tradeoffs that come with giving up control of property. Dennis also explains the tax implications of selling a home inside an irrevocable trust, how step-up in basis rules work, and why timing matters when considering these strategies. If you’ve heard that irrevocable trusts automatically protect your assets, this episode provides a balanced perspective on both the potential benefits and the risks families should carefully evaluate before making permanent decisions. Key takeaways: What makes an irrevocable trust different Why timing and age matter The risks of losing control over property Potential tax consequences for heirs And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

July 9, 202627 min

Estate Planning Mistakes That Can Burden Your Family (Ep. 141)

Estate planning is easy to delay until the people you love are left sorting through the fallout. What happens when missing documents, wrong beneficiaries, or an unfunded trust create delays, costs, and family stress? In this episode, Dennis O’Keefe shares hard-earned lessons about estate planning mistakes that can burden children and other loved ones. He covers why wills matter, how powers of attorney work, why beneficiary choices are critical, how to choose the right people for key roles, and why funding a trust may be one of the biggest steps families overlook. Key takeaways: Why a will helps direct assets instead of leaving major decisions to state intestacy laws How durable and springing powers of attorney can affect family decisions during illness Why naming an estate as a beneficiary can create taxes, probate delays, and family conflict How choosing trustees, executors, and proxies requires judgment, not family rank Why an unfunded living trust may still leave your family dealing with probate costs And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

June 25, 20266 min

What Is Probate?

What exactly is probate, and why do so many families want to avoid it? In this YSR FAQ episode, Dennis explains how the probate process works, where it originated, and why having a will does not automatically keep your estate out of probate court. Using stories from English history to modern-day estate settlement examples, this episode breaks down why probate can become slow, public, and expensive for families handling an estate after a loved one passes away. Dennis also explains how probate laws developed over centuries and why estate planning today still relies on systems created hundreds of years ago. If you’ve ever wondered how assets get distributed, what courts actually do during probate, or why trusts are often used to avoid delays, this episode offers a clear and practical explanation. Key takeaways: Why a will still goes through probate How probate began centuries ago Why probate can become public and expensive What executors and personal representatives do And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

June 25, 20266 min

Do You Need a Will?

Do you actually need a will? In this YSR FAQ episode, we break down one of the most common estate planning questions and explain why a will still matters, even if some of your assets already have built-in protections. Dennis walks through how jointly owned property, beneficiary designations, and transfer-on-death accounts work, and what happens when someone passes away without a will. This episode also explores the probate process, how state intestacy laws decide who inherits your assets, and why outdated or missing beneficiary forms can create major problems for families. Along the way, Dennis shares real-world stories and practical insights that help simplify a topic many people avoid talking about. Key takeaways: Why most adults should have a will How joint ownership affects inheritance The importance of updated IRA and 401(k) beneficiaries What happens if you pass away without a will And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.

June 11, 202626 min

Don’t Trust the Easy Answer: How Bad Information Can Hurt Your Financial Decisions

It’s easy to believe something just because it sounds confident or is widely accepted. But what if the stories we trust most, from history to headlines to financial advice, are often simplified, distorted, or just plain wrong? In this episode, Dennis O’Keefe discusses how human nature pushes us toward easy answers and how those shortcuts can lead to poor financial decisions. Whether it’s viral social media claims, sensational media narratives, or even government policies that sound helpful on the surface, Dennis shares why it’s critical to pause, question, and look more deeply before taking action. Key takeaways: Why people are wired to accept simple stories, even when they’re misleading How social media can spread confident but inaccurate financial ideas What drives media narratives, and why they may not serve your best interests Real-world examples of policies that sound helpful but may create bigger problems And more! Connect with Dennis O’Keefe: Successful Money Strategies, Inc dennis@successfulmoney.com (508) 730-2300 LinkedIn: Dennis O’Keefe LinkedIn: Successful Money Strategies, Inc Facebook: Successful Money Strategies, Inc Instagram: Successful Money Strategies, Inc YouTube: Your Successful Retirement Podcast All content presented is for educational purposes only and should not be construed as an endorsement of any third party, or as a solicitation or offer to sell securities or provide investment, tax, legal, or consulting services, and should not be acted upon without obtaining specific advice from a qualified professional. We believe the information presented to be reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. Any opinions or statements by third parties are their own and may not be representative of the experience of others or indicative of future investment performance or success. No compensation has been exchanged for any testimonials, endorsements, and/or recognitions.