Tag: Retirement
Greed vs. Fear: Managing Emotions in Your Investment Portfolio

Greed vs. Fear: Managing Emotions in Your Investment Portfolio

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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:

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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.
Outsmarting Instincts in Market Chaos

Outsmarting Instincts in Market Chaos

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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: 

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.
How Inflation Shapes Your Financial Strategy

How Inflation Shapes Your Financial Strategy

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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: 

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.
Overcome Financial Anxiety and Retirement Fears

Overcome Financial Anxiety and Retirement Fears

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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: 

 

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 We Headed for Another Real Estate Crash?

Are We Headed for Another Real Estate Crash?

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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: 

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.
Unlock the Secrets of Living Trusts

Unlock the Secrets of Living Trusts

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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: 

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.
Financial Planning Unveiled: What You Need to Know for a Secure Future

Financial Planning Unveiled: What You Need to Know for a Secure Future

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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: 

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.
Financial Wellness: Your First Meeting with an Advisor

Financial Wellness: Your First Meeting with an Advisor

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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: 

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.
The Pros and Cons of Automated Investment Services

The Pros and Cons of Automated Investment Services

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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 into automated investment services, how they work, the pros and cons, and whether they truly offer the expertise and personalization you need.

If you’re questioning whether a target date fund is the best choice for your long-term financial goals, this episode is for you! Tune in for a better understanding of how these funds operate and whether they align with your financial future.

Highlights include:

  • The ins and outs of investment management services
  • The potential pitfalls of relying solely on automation
  • Why personalized advice and relationships matter 
  • Personal tales that underscore the value of a tailored approach
  • And more

Connect with Dennis O’Keefe: 

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.
Estate Planning Mistakes That Could Cost You Everything

Estate Planning Mistakes That Could Cost You Everything

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Estate planning is one of those things we all know we should do, yet most of us keep pushing it off—just like changing the furnace filter (which, by the way, can have disastrous consequences if ignored). But failing to plan your estate properly can leave your loved ones with unexpected legal and financial nightmares. 

Join Dennis as he breaks down why having a will is essential, common estate planning mistakes, and a surprising history lesson on how modern wills came to be.

Top takeaways include:

  • The importance and function of wills in estate planning [00:01:23]
  • Common mistakes people make with estate planning [00:06:45]
  • A historical journey beginning with the Magna Carta to understand current practices [00:14:50]
  • The American perspective on individual rights in estate planning [00:24:30]
  • Practical advice for managing your estate and why you shouldn’t DIY your will [00:37:15]
  • And more

Connect with Dennis O’Keefe: 

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.