Tag: Telecom 401(k) Retirement Savings Plans
Can AI Really Replace Human Financial Guidance?

Can AI Really Replace Human Financial Guidance?

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Join us this episode as Dennis O’Keefe outlines the ways AI tools are being used in financial planning and where they currently fall short. He explains how automated systems process information, where they provide efficiency, and the limitations that appear when personal context or situational nuance is required. 

Dennis also describes the differences between automated platforms, large national firms, and independent fiduciary advisors, focusing on how each model approaches service and decision support.

Key takeaways:

  • AI can help organize data and handle defined tasks, but it does not interpret personal context or long-term considerations.
  • Large firms provide structure, yet personalization may vary depending on how their service models are designed.
  • Independent advisors may identify risks or opportunities that automated systems do not detect.
  • Retirees should consider what level of support they want when evaluating technology-based planning tools.
  • 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 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.
Protecting Your Money from Modern Scams

Protecting Your Money from Modern Scams

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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: 

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

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

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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 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:

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 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?

Are Roth IRAs Worth It?

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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: 

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

Care Options for Older Americans

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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: 

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 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.
Elderly Planning: What You Need To Know

Elderly Planning: What You Need To Know

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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: 

 

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 To Financially Support Your Adult Children, Without Enabling Them (Part 2)

How To Financially Support Your Adult Children, Without Enabling Them (Part 2)

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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: 

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 To Financially Support Your Adult Children, Without Enabling Them (Part 1)

How To Financially Support Your Adult Children, Without Enabling Them (Part 1)

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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: 

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 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 Debt Can Derail Your Retirement

How Debt Can Derail Your Retirement

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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: 

 

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.
Funding College Without Breaking the Bank

Funding College Without Breaking the Bank

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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: 

 

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.