Your Successful Retirement

Protecting Your Money from Modern Scams

From “Nigerian princes” to “crypto investments,” scams have evolved, but the playbook hasn’t changed.  In this episode, Dennis O’Keefe draws from three decades of experience helping retirees avoid costly traps.  Through real stories and a bit of humor, he breaks down how con artists prey on emotion, urgency, and trust and how you can protect yourself and the people you love. What you can expect from this release: Why even intelligent people fall for scams The red flags every retiree should know How technology has made old scams new again The one simple tech switch that can reduce fraud risk by 95% And so much 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.

Long-Term Care: The Most Overlooked (and Misunderstood) Part of Financial Planning

Planning for long-term care is one of the hardest and most personal financial challenges families face.  Let’s cut through the noise to unpack what really works, what doesn’t, and what might cost you dearly down the line. From irrevocable trusts and annuities to asset transfers and Medicaid’s five-year lookback, he explains the real-world tradeoffs every family must understand before taking action. You’ll also hear why many people default to “doing nothing,” and how that can either preserve flexibility or destroy options completely. What you can expect from this episode: The truth about Medicaid and nursing home coverage How irrevocable trusts actually work (and when they don’t) Why “doing nothing” can sometimes be the smartest short-term move The one type of advisor Dennis says to avoid And more! Previous Episodes of Interest: Elderly Planning: What You Need To Know Care Options for Older Americans 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.

Your Guide to Layoffs, Severance, and Retirement Decisions

When layoffs or retirement offers appear, whether planned or not, they can stir panic and uncertainty. In this episode of Your Successful Retirement, Dennis O’Keefe, CFP®, draws on more than 30 years of experience helping telecom employees navigate these pivotal transitions. He shares a calm, practical approach to managing the emotional and financial stress that follows a sudden career shift. You’ll learn what to consider before signing a severance agreement, the hidden tax implications many overlook, and why COBRA coverage may not be your best option. Dennis also unpacks key strategies around timing your Social Security, managing 401(k) withdrawals, and avoiding the costly pitfalls that can derail your long-term plan. Key takeaways: How to evaluate a severance package and understand its real after-tax value Why preparation matters more than panic when a layoff hits Smarter health insurance choices after employment ends When and why to consider taking Social Security early 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.

Are Roth IRAs Worth It?

You’ve seen the Roth conversion hype, the slick Instagram reels, the pushy advisors, the calculators promising massive tax savings. But here’s the real question: Is it actually right for you? We’re breaking the spell of oversimplified Roth conversion advice. The truth? A Roth might not be about you at all; it might be about your children, your legacy, and what happens 20–30 years from now. If you’ve ever wondered whether a Roth conversion is a smart move or a shiny distraction, this episode delivers the clarity you didn’t know you were missing. What you’ll learn: Why tax savings aren’t always the goal (or the outcome) How tax brackets silently kill Roth conversion benefits When a Roth becomes a powerful estate planning tool What you must know before acting on social media advice 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.

Care Options for Older Americans

It used to be simple: either your family took care of you at home, or you went into a nursing home. But those days are long gone.  Dennis O’Keefe walks through the four levels of elder care today: home care, senior living, assisted living, and nursing homes, and explains what each one actually means, how much they cost, and what kind of planning families should be doing now to prepare. He shares stories from his own family, clients, and favorite TV shows (yes, The Sopranos) to help illustrate just how much the landscape of aging has changed and how important it is to drop the outdated myths.  Whether you’re caring for aging parents or thinking about your own future, this episode will give you the clarity and confidence to move forward. What to expect in this episode: What “home care” really includes and why it’s more than just medical help Why food and activities might be the most important factors for long-term independence The truth about Medicaid: what it pays for, and what it doesn’t The emotional and financial trade-offs of preserving money for your kids vs. paying for your own care And more! Previous Episode of Interest:   Elderly Planning: What You Need To Know 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.