Your Successful Retirement

Dennis O'Keefe
  • 4.9 (7)
  • Business
  • Updated Weekly

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.

  1. May 28

    Should I Be Doing This Annuity?

    Should you consider an annuity, or avoid it altogether?  This week, Dennis O’Keefe breaks down how annuities work, why they are often sold rather than bought, and when they may or may not make sense. Using a real client scenario, Dennis explains how annuity proposals can be positioned in ways that don’t always benefit the investor. He also walks through the structure of annuities, including insurance components, tax deferral, and the underlying costs that can impact returns. Key takeaways: What an annuity actually is Why annuities tend to be expensive How commissions and structure impact recommendations When annuities may make sense Why a second opinion can be critical 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.

    9 min

  2. May 28

    What Happens If We Have Another Recession?

    What should investors actually do during a recession? In this release of YSR Shorts, Dennis O’Keefe challenges the common reactions people have when markets decline and explains why those instincts often lead to poor outcomes. Using historical examples and a real-world perspective, Dennis explains why market downturns are part of the economic cycle and how disciplined investors approach them differently. He also highlights the importance of thinking long-term and viewing downturns as opportunities rather than threats. We share: Why investor instincts often work against them Lessons from past market downturns The difference between fear and strategy How to think about buying during declines Why long-term perspective matters 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.

    7 min

  3. May 14

    What Families Need to Know About College Planning Today

    College planning rarely works the way most parents remember it. In this episode, Dennis O’Keefe shares a personal and eye-opening look at today’s college financial aid system after recently guiding his son through the process. What’s changed over the years may surprise you. How applications are submitted, and how aggressively colleges are offering aid… More importantly, he talks about what families should actually be thinking about depending on where their student is in the process, whether college is right around the corner or still years away.  Key takeaways: How decreasing college enrollment is shifting in favor of students and families What the unified application system means for acceptance rates and decision timelines Why financial aid is more available than many parents expect The real cost versus value conversation when choosing between private and public schools How early exposure, relationships, and campus engagement can influence both admissions and aid Smart ways to think about saving for college, including 529 plans, custodial accounts, and flexible alternatives  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.

    29 min

  4. Apr 23

    What Is An Index Fund?

    Everyone talks about index funds.  Do they actually know what they are? Dennis O’Keefe cuts through the jargon and explains what an index really is, why the S&P 500 represents 85% of all US market wealth, and how an index fund lets you own a piece of it without the guesswork. He also covers the key advantages: low cost, simplicity, and flexibility, along with one important disadvantage worth knowing before you invest. You’ll hear: The difference between the Dow Jones and the S&P 500 (and why it matters) How index funds actually work and what you’re buying when you buy one Why the S&P 500 represents 85% of total US market dollars The cost and simplicity advantages of index funds vs. actively managed funds 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.

    8 min

  5. Apr 23

    What Are Asset Allocations?

    Most people confuse asset allocation with diversification, but they are two very different things. In this episode of YSR Shorts, Dennis O’Keefe explains how asset allocation works, where it came from, and why it is one of the most powerful tools in long-term investing. Dennis traces the concept back to Roger Gibson’s groundbreaking 1989 research, breaks down the pie chart model he uses with clients, and explains why maintaining category percentages matters more than picking individual winners. Key takeaways: The difference between diversification and asset allocation How Roger Gibson’s research changed the way portfolios are built Why the percentages between categories matter more than individual stock picks How asset allocation removes emotional decision-making from investing 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.

    7 min

  6. Apr 9

    Understanding Social Security: Myths, Mechanics, and What Happens Next

    Many people think they understand Social Security, until conflicting answers and uncertainty create confusion. What’s actually true about how benefits work, and what should you expect in the years ahead? In this episode, Dennis O’Keefe breaks down how Social Security really works and clears up common misconceptions. He explains how benefits are calculated, why the system is often misunderstood, and what the projected shortfall around 2032 could mean. Dennis also explores how policy changes like tax increases or benefit adjustments may shape the future, helping listeners better understand their options and expectations. Key takeaways: How spousal and dependent benefits can increase total Social Security income when coordinated properly Why Social Security is structured as an insurance program rather than a personal retirement account How the Social Security Trust Fund works and why funds are being drawn down over time The real reason behind the projected 2032 shortfall and what it means for future benefits Potential changes like higher payroll taxes or income-based benefits that could reshape the system 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.

    26 min

  7. Mar 26

    What Does “Fiduciary” Really Mean?

    What does it mean to be a fiduciary? In this episode of YSR Shorts, Dennis O’Keefe explains the fiduciary standard and why it matters in financial services. He discusses disclosure, compensation structures, and why fiduciary status should be part of your evaluation, not the only factor. Dennis also shares real-world examples that highlight the importance of asking deeper questions. Key takeaways: Definition of fiduciary in financial services Why disclosure matters Limits of fiduciary protection The importance of evaluating competence and trust 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.

    7 min

  8. Mar 26

    Should You Pay Someone to Manage Your Money?

    Should you pay someone to manage your money? In this episode, Dennis O’Keefe explains the behavioral side of investing. He shares why emotional reactions during market volatility can hurt long-term results and how professional management can help create separation and discipline. Dennis also compares corporate management firms and boutique advisory relationships, outlining the pros and cons of each. Key takeaways: Why investor behavior matters during market swings The value of emotional separation in decision-making Differences between large firms and boutique advisors The importance of proactive guidance 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.

    7 min
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4.9
out of 5
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About

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.

Information

  • Creator
    Dennis O'Keefe
  • Years Active
    2022 - 2026
  • Episodes
    146
  • Rating
    Clean
  • Copyright
    Copyright © 2024 Your Successful Retirement
  • Show Website
    Your Successful Retirement