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Category: Podcast

Ep. 105: Whiteboard Retirement Plan (Retire with $2.3 million AND Die with $2.3 million)

PFR Nation,

I hope you all had a wonderful Thanksgiving holiday! It’s been a while since we did a Whiteboard Retirement Plan breakdown, so lets get this back in the rotation!

In this scenario, we are looking at a baseline scenario for Jack and Barbara, who have saved $2.3million for retirement, mostly in tax-deferred accounts. They would like to retire at 61 (2026), but they are very concerned about financial legacy for their two adult children. In fact, not only do they want to protect and preserve their assets, but they also want to do so on an inflation-adjusted basis! Let’s see how they are tracking with the baseline plan, and let’s see what levers they need to pull in order to achieve their retirement AND legacy objectives.

And I’d love to hear from you all. What levers would YOU pull if you were Jack and Barbara?

Thanks for tuning in and please make sure to leave us a nice review if you are finding value in the content!

-Kevin

⁠⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 104: 8 Roth Conversion Tax Traps

PFR Nation,

It’s the most wonderful time of the year…

You guessed it…it’s ROTH CONVERSION time! 😊

In all seriousness, Happy Thanksgiving all of you! Wishing you a wonderful start to the holiday season.

Roth Conversions are a hot topic in our business at the end of the year, so I thought I’d do a video about some common tax traps every day retirees run in to as they are converting assets to Roth. I hope you find it useful!

Let me know if there are any other tax traps you can think of.

Also, drop a comment…do you plan to convert your IRA to Roth during your Roth Conversion window?! I would love to hear from you.

-Kevin

Resources mentioned:

  • The ACA Premium Tax Credits Are Changing in 2026 (video)
  • 7 Reasons NOT to convert your IRA to Roth (episode)

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website, so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 103: 100 Episodes, 100 Lessons (Part 4)

Welcome to PART 4 of 100 Episodes, 100 Lessons (for retirees and pre-retirees).

In this episode, we’ll walk through episodes 76-99 and bring home some key takeaways for you as you plan for and execute a successful retirement. I hope you enjoy this one!

If you are over 50, you’ve saved north of $1million for retirement, and you want to maximize retirement income, minimize your lifetime tax bill, and worry less about money…hit the FOLLOW button so you don’t miss out on the next 100 episodes!

-Kevin

⁠⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 102: 100 Episodes, 100 Lessons (Part 3)

PFR Nation,

Welcome to PART 3 of 100 Episodes, 100 Lessons (for retirees and pre-retirees).

In this episode, we’ll walk through episodes 51-75 and bring home some key takeaways for you as you plan for and execute a successful retirement. I hope you enjoy this one! 

If you are over 50, you’ve saved north of $1 million for retirement, and you want to maximize retirement income, minimize your lifetime tax bill, and worry less about money…hit the FOLLOW button so you don’t miss out on the next 100 episodes! 

-Kevin

⁠⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 101: 100 Episodes, 100 Lessons (Part 2)

The journey continues. We are walking through 100 lessons from the first 100 episodes in this 4-part series. I hope you enjoy part 2!

If you are over 50, you’ve saved north of $1million for retirement, and you want to maximize retirement income, minimize your lifetime tax bill, and worry less about money…hit the FOLLOW button so you don’t miss out on the next 100 episodes!

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website so we can learn more about how we can help in your journey to and through retirement.
~ Kevin

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 100: 100 Episodes, 100 Lessons (Part 1)

PFR Nation:

Thank you all for supporting this show for the last few years. Especially for those of you who supported me in the early days when I thought nobody was listening. I even took a 4 month hiatus without announcing it because we were so in the trenches with our boys. All of a sudden I get an email out of the blue asking “Are you still doing the podcast?” That was the motivation I needed to get back in the game and just ‘hit record.’ In 2023, I began posting consistently ever 2 weeks. And in the beginning of 2025, I decided to go weekly! It hasn’t been easy, but I just want to thank all of you for keeping me motivated, this is why I do what I do. Keep the comments coming and make sure to share our show with someone you care about who is PFR Nation caliber!

Naturally, I was overthinking what I would do for this episode. However, my wife helped me simplify it per usual. I will be breaking down my top takeaway/lesson from all of the previous episodes, and we’ll do it in 4 parts. Part 1 covers episodes 1-25, so lets take a walk down memory lane together and recap important points from those early episodes. I hope you enjoy this series!

-Kevin

⁠⁠⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website, so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 99: How Do We Design a Plan When My Spouse And I Feel Differently About Retirement Income? How Do I Possibly Calculate How Much For Long-Term Care, Medicare, Health Care? (Retirement Q&A)

PFR Nation,

As you know, we are well underway with our free giveawaysfrom a couple of weeks ago. And as I mentioned last week, we received a lot of great comments in that YouTube thread! So last week, I touched on three of the questions in a Q&A format.  Today, I’ll address three more! 

Here they are:

1.       “So how do you actually build a retirement income plan that both people can sleep at night with when one side wants market exposure and the other wants safety?”

2.       “I’ve set aside (spreadsheet) my calculated number to self-fund my long-term care, but the variables and assumptions concern me.”

3.       “How do we pay for health care before Medicare?”

You’re not going to want to miss this one, and hope you find it useful!  Thanks for tuning in.

-Kevin

Resources Mentioned in this Episode:

  • Genworthand Carescout Cost of Care
  • The ACA Premium Tax Credits AreChanging in 2026! (PFR Video)

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠You can start with our Retirement Readiness Questionnaire linked on our website, so we can learn more about how we can help in your journey to and through retirement.

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal, or investment advice.

Ep. 98: Convert to Roth before RMDs? Scared to Spend? Age Gap Early Retirement! (Retirement Q&A Session)

PFR Nation,

We just announced our FREE GIVEAWAY winner and runner-up on the YouTube channel last Thursday. Thank you all for participating and making that process super enjoyable and engaging. One of the questions I asked for the giveaway was “What is one thing related to planning for retirement that keeps you up at night?” We received some amazing responses!! So, I thought I would dedicate this episode and the next to addressing some of the best questions in that YouTube thread.

This episode, we will wrestle with three of them:

  1. I have the majority of my retirement savings in pre-tax accounts, so I am worried about how to do the complex math to optimize Roth conversions before RMDs kick in.
  2. I worry that after a lifetime of saving, will I be able to draw down my retirement savings?
  3. My wife is 9.5 years younger than me. I want to retire in a few years at 55, not sure how long after that she’ll keep working. But with that age gap it’s a long retirement timeline. How best do you plan for that?

You’re not going to want to miss this one and hope you find it useful! Thanks for tuning in.

-Kevin

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal or investment advice.

Ep. 97: The Four Phases of Retirement – And How To Skip The Dark and Depressing Phase

PFR Nation,

I recently discovered a Ted Talk by Dr. Riley Moynes about the “4 phases of retirement.” 

We talk a lot about the financial side of retirement planning.

–             Safe withdrawal rates

–             Tax efficiency

–             Investing to and through retirement

–             Legacy

–             Insurance

However, it’s equally important to understand and think about the softer side of retirement planning. In this episode, you will want to hear Dr. Moynes’ take on the 4 phases,and I’ll talk about a real-life hero in the College Football world that canhopefully inspire you to SKIP the dark and depressing phase! 

I hope you enjoy this one.

-Kevin

Takeaways

·     Retirement is not just a financialtransition; it’s an emotional journey.

·     Understanding the four phases ofretirement can help avoid pitfalls.

·     The vacation phase is characterized byfreedom and excitement.

·     The loss phase involves identity andpurpose challenges.

·     Michael Phelps’ experience illustratesthe emotional struggles of retirement.

·     Therapy and seeking help can be crucialduring transitions.

·     Finding new meaning in retirement isessential for fulfillment.

·     Engaging in service and mentoring canenhance retirement satisfaction.

·     Financial independence allows forexploration of new passions.

·     Planning for purpose in retirementshould start before retirement begins.

Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal or investment advice.

Ep. 96: Short-form Media is Ruining America, and Their Retirements

PFR Nation,

In this episode, I’m tackling America’s “headline culture,” how short clips and soundbites dominate not only politics, but also the way we think about retirement planning. With the tragic assassination of Charlie Kirk as a starting point, I reflect on how social media algorithms amplify the loudest, most divisive voices, while thoughtful, nuanced conversations get drowned out. When I dug into Charlie’s long-form interviews, like his sit-down with Gavin Newsom, I realized how much context gets lost and how much more common ground we really share when we go deeper.

The same thing happens in retirement planning. Viral soundbites like “Social Security is going bankrupt,” “Never pay off your mortgage,” “The 4% rule always works,” or “Financial advisors can’t beat the market, so don’t hire one” may sound convincing in 20 seconds, but they can be misleading and even harmful if you base major decisions on them.

In this episode, I break down why these headlines don’t tell the full story and what you should consider instead.

At the end of the day, just like politics, retirement requires long-form thinking. The clips may get clicks, but the deeper conversation is where the truth, and a confident retirement, really lives.

-Kevin

⁠⁠⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠ 

⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire

Connect with me here:

Or, ⁠⁠⁠⁠⁠⁠⁠⁠visit my website

This is for general education purposes only and should not be considered as tax, legal or investment advice.

info@imaginefinancialsecurity.com
(904) 323-2069

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