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.

Your Telecom Retirement
Claim This Podcastby Dennis O'Keefe
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Podcast Overview
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.
Language
🇺🇲
Publishing Since
4/14/2022
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Recent Episodes

July 9, 2026
Estate Planning Mistakes That Can Burden Your Family (Ep. 141)
<p><span style="font-weight: 400;">Estate planning is easy to delay until the people you love are left sorting through the fallout.</span></p> <p><span style="font-weight: 400;">What happens when missing documents, wrong beneficiaries, or an unfunded trust create delays, costs, and family stress?</span></p> <p><span style="font-weight: 400;">In this episode, Dennis O’Keefe shares hard-earned lessons about estate planning mistakes that can burden children and other loved ones. He covers why wills matter, how powers of attorney work, why beneficiary choices are critical, how to choose the right people for key roles, and why funding a trust may be one of the biggest steps families overlook.</span></p> <p><span style="font-weight: 400;">Key takeaways:</span></p> <ul> <li><span style="font-weight: 400;">Why a will helps direct assets instead of leaving major decisions to state intestacy laws</span></li> <li><span style="font-weight: 400;">How durable and springing powers of attorney can affect family decisions during illness</span></li> <li><span style="font-weight: 400;">Why naming an estate as a beneficiary can create taxes, probate delays, and family conflict</span></li> <li><span style="font-weight: 400;">How choosing trustees, executors, and proxies requires judgment, not family rank</span></li> <li><span style="font-weight: 400;">Why an unfunded living trust may still leave your family dealing with probate costs</span></li> <li><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O’Keefe: </b></p> <ul> <li style="font-weight: 400;" aria-level="1"><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="mailto:dennis@successfulmoney.com"><span style="font-weight: 400;">dennis@successfulmoney.com</span></a><span style="font-weight: 400;"> </span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">(508) 730-2300 </span></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O’Keefe</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>

June 25, 2026
What Is Probate?
<p><span style="font-weight: 400;">What exactly is probate, and why do so many families want to avoid it? In this YSR FAQ episode, Dennis explains how the probate process works, where it originated, and why having a will does not automatically keep your estate out of probate court.</span></p> <p><span style="font-weight: 400;">Using stories from English history to modern-day estate settlement examples, this episode breaks down why probate can become slow, public, and expensive for families handling an estate after a loved one passes away. Dennis also explains how probate laws developed over centuries and why estate planning today still relies on systems created hundreds of years ago.</span></p> <p><span style="font-weight: 400;">If you’ve ever wondered how assets get distributed, what courts actually do during probate, or why trusts are often used to avoid delays, this episode offers a clear and practical explanation.</span></p> <p><span style="font-weight: 400;">Key takeaways:</span></p> <ul> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Why a will still goes through probate</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">How probate began centuries ago</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Why probate can become public and expensive</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">What executors and personal representatives do </span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O’Keefe: </b></p> <ul> <li style="font-weight: 400;" aria-level="1"><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="mailto:dennis@successfulmoney.com"><span style="font-weight: 400;">dennis@successfulmoney.com</span></a><span style="font-weight: 400;"> </span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">(508) 730-2300 </span></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O’Keefe</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>

June 25, 2026
Do You Need a Will?
<p><span style="font-weight: 400;">Do you actually need a will? In this YSR FAQ episode, we break down one of the most common estate planning questions and explain why a will still matters, even if some of your assets already have built-in protections. Dennis walks through how jointly owned property, beneficiary designations, and transfer-on-death accounts work, and what happens when someone passes away without a will.</span></p> <p><span style="font-weight: 400;">This episode also explores the probate process, how state intestacy laws decide who inherits your assets, and why outdated or missing beneficiary forms can create major problems for families. Along the way, Dennis shares real-world stories and practical insights that help simplify a topic many people avoid talking about.</span></p> <p><span style="font-weight: 400;">Key takeaways:</span></p> <ul> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">Why most adults should have a will</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">How joint ownership affects inheritance</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">The importance of updated IRA and 401(k) beneficiaries</span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">What happens if you pass away without a will </span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">And more!</span></li> </ul> <p><b>Connect with Dennis O’Keefe: </b></p> <ul> <li style="font-weight: 400;" aria-level="1"><a href="https://www.successfulmoney.com/"><span style="font-weight: 400;">Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="mailto:dennis@successfulmoney.com"><span style="font-weight: 400;">dennis@successfulmoney.com</span></a><span style="font-weight: 400;"> </span></li> <li style="font-weight: 400;" aria-level="1"><span style="font-weight: 400;">(508) 730-2300 </span></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/in/dennisokeefe-/"><span style="font-weight: 400;">LinkedIn: Dennis O’Keefe</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.linkedin.com/company/successful-money-strategies-inc./"><span style="font-weight: 400;">LinkedIn: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.facebook.com/successfulmoneystrategies"><span style="font-weight: 400;">Facebook: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.instagram.com/successfulmoneystrategies/"><span style="font-weight: 400;">Instagram: Successful Money Strategies, Inc</span></a></li> <li style="font-weight: 400;" aria-level="1"><a href="https://www.youtube.com/@SuccessfulRetirementPodcast"><span style="font-weight: 400;">YouTube: Your Successful Retirement Podcast</span></a></li> </ul> <p><span style="font-weight: 400;">All content presented is for educational purposes only and </span><span style="font-weight: 400;">should not be construed as </span><span style="font-weight: 400;">an endorsement of any third party, or as</span><span style="font-weight: 400;"> 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 </span><span style="font-weight: 400;">reliable, but it is not guaranteed as to its accuracy or completeness. All examples are hypothetical and for illustrative purposes only. </span><span style="font-weight: 400;">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.</span></p>
152 total episodes available
Deep-dive analytics for Your Telecom Retirement
Frequently asked questions
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- What is Your Telecom Retirement?
- How often does this podcast release new episodes?
This podcast updates weekly.
- Where can I listen to this podcast?
This podcast is available on 9 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
- Does this podcast accept guests?
No, this podcast does not typically feature guests.
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