Your Successful Retirement

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.

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.

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.

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.

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.

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 slow down, ask sharper questions, and protect your retirement from unnecessary risk. Key takeaways: Why “hero stories” of big wins can mislead investors The hidden risks behind gold’s surge and crypto’s speculation Why private equity funds may not belong in a 401(k) The uncertainty of monetizing AI and emerging trends The importance of research, perspective, and clarity in retirement planning 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.

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 confusing and emotionally charged questions in retirement planning: Why is healthcare so expensive, and where is all that money going? From drug pricing myths to the ripple effects of private equity, Dennis brings over 30 years of financial wisdom to help you make sense of what’s really driving healthcare inflation (and what you can and can’t do about it). What to expect: A personal story that explains why Americans are wired to demand choice and how that affects cost A breakdown of the real drivers behind rising expenses, including specialization and advertising The truth behind generic vs. name-brand prescriptions Why private equity is quietly reshaping the healthcare landscape and what that means for you 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.

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 supporting loved ones.  He explains why thinking conceptually about your future needs before jumping into legal documents or strategies lays the foundation for confident, compassionate decisions later on. What You’ll Learn: Why family proximity matters for future care How housing design today can save stress tomorrow Why “thinking ahead” beats rushing to estate documents What questions to ask now to prepare for your 80s and beyond 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.

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: rising living costs, delayed parenthood, demographic shifts, and a changing retirement landscape. You’ll learn how to prepare your family for: The high cost of urban living and the difficulty of building in America’s cities Declining birth rates and what that means for care in old age The future of Social Security and the role immigration may play Your changing role in the family, from “king” to “sage” 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 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.

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 may be unintentionally making things harder. From soaring housing costs to student loan debt, and from generational shifts to emotional decision-making, this episode offers perspective, clarity, and some hard truths about the future. What to expect: A nostalgic story about mall culture and generational change Why do many young adults delay marriage, kids, and homeownership How over-supporting your kids can hurt more than help Why struggle builds strength and how to let it happen And more! Resources:  What Happens When a Whole Generation Never Grows Up? – The Wall Street Journal 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.

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, historical examples, and common traps that lure people into debt, including 0% offers, home equity loans, credit card traps, and extended auto loans. What to expect: Why debt is so destructive for retirees The hidden dangers behind seemingly “good” debt offers How generational attitudes toward debt shift after economic crises Actionable steps you can take today to protect yourself or your loved ones 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.

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 today’s world.  Spoiler alert: It’s not as clear-cut as it once was. Highlights of this episode include: Is a college degree still worth the cost?  The historical rise in college tuition and what it means for your wallet  Understanding 529 plans for savvy college savings  The hidden costs and pitfalls of student loans  Real-world strategies for building your education fund  The frightening reality of college financial aid and family contributions  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.

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 the spotlight on the dangers of greed when everything seems to be going well.  Dennis discusses:  The powerful emotions driving investment decisions: fear and greed The famous Wall Street saying: “Bulls make money, bears make money, pigs get slaughtered.” Cautionary tales from the dot-com bubble with telecom and tech stocks Understanding asset allocation and its impact on reducing portfolio volatility And more Previous Episode of Interest: Outsmarting Instincts in Market Chaos 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.

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 history, like the notorious 1987 crash and recent 2025 market fluctuations, to showcase why instincts might lead us astray. Discover practical strategies to ride out financial storms and avoid the pitfalls of panic selling. Dennis discusses:  [00:04:30] The emotional urge to sell during a market drop [00:12:45] A tale of missed opportunities from the ’87 market crash [00:28:22] Why predicting market tops or bottoms is nearly impossible [00:35:40] Tips on how to approach buying during downturns [00:42:10] Lessons from behavioral economics on decision making 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 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 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.

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 breaks down the Consumer Price Index (CPI), providing you with a solid understanding to navigate your retirement in today’s economic climate Dennis discusses:  Historical inflation trends [00:02:30] Understanding the CPI and its impact [00:08:45] Changes in consumer spending habits [00:15:10] The disparity in price changes [00:18:05] Planning for retirement with inflation in mind [00:26:00] 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 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.

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 it seems and highlights the importance of preparing for this significant life transition. Listen in as he shares a compelling story of a retiree who learned the hard way about the potential pitfalls of poor financial planning.  Dennis discusses:  The permanent nature of retirement decisions [01:42] Real-life anecdotes from retirees’ financial journeys [06:04] How to effectively calculate your expenses and resources [22:42] Strategies for reducing anxiety around financial planning [25:56] 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 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.

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 tells us about market patterns, and how experiences from past decades can inform current decisions.  From reminiscing about infomercials to personal anecdotes about the joys and pitfalls of past real estate investments, this episode is a must for anyone interested in financial wisdom through time. Dennis discusses: The concept of patterns in financial markets and their importance [00:05:23] Personal experiences with real estate investments during different market cycles [00:12:47] Real estate trends from the 1980s to today and what they could mean for the present [00:25:16] Critical considerations for current and future real estate transactions [00:38:45] 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 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 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 it all down in a friendly and digestible way.  Dive into the podcast as Dennis shares insights on: The history and purpose of living trusts Differences between various types of trusts and when they might be needed Real-life examples demonstrating the efficiency of living trusts compared to traditional wills Common pitfalls to avoid when setting up a trust Cost considerations and strategic benefits of trusts  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 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.

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 in as Dennis covers: The essence of a true financial planner vs. the common misconceptions [00:02:00] The five pillars of financial planning: retirement, investments, income taxes, estate planning, and asset protection [00:15:00] Real stories and the nuanced financial planning process that starts with a friendly chat and evolves into a customized strategy [00:30:00] How staying proactive with adjustments and engaging in the OODA loop helps keep your financial plan relevant [01:25:00] 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 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.

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 it to be a comfortable, collaborative experience. Whether you’re preparing for retirement, evaluating your investments, or simply seeking guidance, this episode will give you a clear understanding of what to expect in your first meeting with a financial advisor—and how it can set the stage for a secure financial future. Dennis discusses:  The stress of initial financial meetings vs. doctor visits [00:05:00] How personal history shapes our interactions with professionals [00:10:00] Importance of building trust and privacy in financial consultations [00:20:00] Comprehensive financial assessments tailored to individual needs [00:35:00] An engaging explanation of why client comfort is key to long-term success [00:45:00] 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 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.