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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.
131 Episodes
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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 … Read More Read More
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 … Read More Read More
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 … Read More Read More
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 … Read More Read More
In this episode, Dennis O’Keefe takes a candid look at the kinds of investments he personally avoids and why. From gold and crypto to private equity and AI, Dennis shares stories, history, and hard-won lessons about what happens when hype outweighs fundamentals. His goal isn’t to tell you what to buy, but to help you … Read More Read More
When Dennis O’Keefe was growing up, his family called him “Mr. Perfect” and “The Shell Answer Man” because he always had an answer for everything. Decades later, that nickname still fits, especially when it comes to the complicated, frustrating world of healthcare costs in America. In this episode, Dennis dives into one of the most … Read More Read More
When it comes to planning for retirement, most of us stop at saving and investing. But what about the years after 80, the stage when care, housing, and advocacy become crucial? In this episode, Dennis O’Keefe, CFP®, shares personal stories of his own family’s journey through late-stage care, housing transitions, and the emotional complexities of … Read More Read More
What if the greatest financial gift you could give your children isn’t money, but foresight? In this second installment of how to support your adult children, Dennis O’Keefe, CFP®, shifts the focus from today’s challenges to tomorrow’s realities. Drawing on personal stories, national trends, and decades of planning experience, Dennis explores the silent storm ahead: … Read More Read More
What if helping your adult children is holding them back? In this episode, Dennis O’Keefe explores the tough reality many parents face: when does financial support cross the line into enabling? Drawing on personal stories and over 30 years of financial planning experience, Dennis unpacks why today’s 30-somethings are struggling with independence and how parents … Read More Read More
What if the greatest threat to your retirement isn’t your income, savings, or investments, but your debt? In this eye-opening episode, Dennis O’Keefe, CFP®, breaks down why debt is the single most dangerous factor for retirees, often more damaging than people realize. Drawing from over 30 years of financial planning experience, Dennis shares personal stories, … Read More Read More
How are you planning to fund your child’s college education—cash, loans, or perhaps a towering pile of fortune cookies? Dennis O’Keefe dives into the ever-daunting topic of college expenses. With tuition rates soaring higher than vintage 1980s laptops, Dennis breaks down the different ways to prepare financially and discusses the value of a degree in … Read More Read More
Why do your investments soar when you’re least expecting them to, only to plummet when you’re not prepared? Join seasoned financial planner Dennis O’Keefe as he highlights the highs and lows of financial planning, focusing this time on mastering the art of managing a thriving portfolio. Drawing on over 30 years of experience, Dennis turns … Read More Read More
Curious about why markets crash and how our own brains can trip us up? In this episode, Dennis O’Keefe navigates the complex psychology guiding our financial decisions, specifically when our “reptilian brain” pushes us to act against our best interests during market volatility. Join Dennis, a seasoned financial planner, as he shares eye-opening tales from … Read More Read More
Ever wondered how inflation impacts your retirement nest egg? Or how the price shift from eggs to bananas affects your financial plans? Join Dennis O’Keefe, a seasoned financial planner, as he uncovers the complexities of inflation and its profound implications on your future finances. Dennis reflects on the evolving inflation rates through the years and … Read More Read More
Curious about what truly goes into planning a successful retirement? Why is retirement deemed the most challenging life event you’ll ever face? Join Dennis O’Keefe, a seasoned financial planner with over 30 years of experience, as he demystifies the retirement process in this episode. Dennis dives deep into why retirement can be more daunting than … Read More Read More
Is the real estate market heading for another crash, or have we simply hit a plateau? Dennis O’Keefe invites you on a journey through the patterns of past real estate markets that might just give you insight into today’s trends. Dennis breaks down whether we’re on the brink of a real estate bubble, what history … Read More Read More
Are you prepared to simplify the complex world of estate planning with trusts? Tune in as Dennis O’Keefe sheds light on the intricacies of living trusts and how they can become a vital component of your retirement planning strategy. Whether you’re considering a trust yourself or just eager to enhance your financial literacy, Dennis breaks … Read More Read More
What exactly do financial planners do? Explore valuable insights into retirement planning with Dennis O’Keefe, a seasoned, certified financial planner with over 30 years of experience. Whether you’ve been retired for years or on the verge of retirement, or are wondering how to plan for your someday retirement, this podcast is your go-to guide. Tune … Read More Read More
When it comes to financial planning, the first meeting is about more than just crunching numbers—it’s about understanding your full financial picture, addressing your concerns, and setting a foundation for informed decision-making. Join CERTIFIED FINANCIAL PLANNER™, Dennis O’Keefe walks you through what happens in that initial conversation and how he and his team have designed … Read More Read More
Are you overwhelmed by investment management ads promising to handle your money easily? What’s the deal, and are they worth it? Dennis O’Keefe dives into the world of automated investment management and the critical differences between computer and personal touch in retirement planning. With over 30 years of financial planning experience, Dennis shares invaluable insights … Read More Read More
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