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Category: Podcast

Ep. 125: 12 Roth Conversion Landmines That Could Cost Retirees Thousands

Last week, we covered why Roth conversions can beso powerful in retirement planning.

This week, we’re talking about what can go wrong.

In this episode, I walk through 12 real-world hurdles and“landmines” that can shrink — or completely eliminate — your Roth conversion window. These are the exact issues I see with retirees and pre-retirees whohave built substantial wealth in traditional IRAs, 401(k)s, and other tax-deferred accounts.

We cover:

  • Social Security timing
  • Pension income
  • Spousal employment
  • Selling a business
  • Deferred compensation plans
  • IRMAA surcharges
  • ACA premium tax credits
  • Inherited IRAs and the 10-yearrule
  • Tax-inefficient investments
  • The new senior bonus deduction

And more.

If you’re planning for retirement and want to minimize lifetime taxes while maximizing flexibility, this episode will help you avoid some very costly mistakes.

I hope you find it helpful.
~ 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. 124: 7 Reasons Retirees Should Consider Roth Conversions

If you’re approaching retirement with a large 401(k) or IRA balance, this episode could save you and your beneficiaries hundreds of thousands in future taxes.

In this episode I’ll break down 7 strategic reasons to consider Roth conversions and explain when Roth conversions actually make sense for retirees and pre-retirees.

Too many financial “gurus” push Roth conversions as a one-size-fits-all strategy. In reality, timing matters. Tax brackets matter. Medicare premiums matter. Legacy planning matters.

You’ll learn:
✔️ How Roth conversions can reduce future RMDs (Required Minimum Distributions)
✔️ Why retirees get trapped by large IRA balances later in life
✔️ The hidden “widow penalty” surviving spouses face
✔️ How Roth IRAs can create tax-free retirement income flexibility
✔️ Why the SECURE Act changed inherited IRA planning forever
✔️ How Roth conversions may protect your children from massive tax bills
✔️ The best Roth conversion window for retirees ages 55–75
✔️ When NOT to do Roth conversions
✔️ How market downturns can create Roth conversion opportunities
✔️ The impact Roth conversions can have on IRMAA, Social Security taxation, ACA subsidies, and Medicare premiums

Whether you have $1M, $3M, or more saved for retirement, understanding Roth conversion planning could dramatically improve your retirement income strategy and long-term tax efficiency.

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. 123: Trump Accounts: Smart Move or Overhyped?

In this episode, I’ll break down the brand-new TrumpAccounts created under the One Big Beautiful Bill Act and explain whether retirees and near-retirees should consider using them as part of their legacy planning strategy.

If you’ve built substantial retirement savings and are thinking about:

  • Helping children or grandchildren financially
  • Reducing future estate taxes
  • Gifting while living
  • Creating generational wealth

This episode walks through the pros, cons, tax implications, and alternatives to Trump Accounts in plain English.

I’ll also compare Trump Accounts to:

  • 529 college savings plans
  • Custodial brokerage accounts(UGMA/UTMA)
  • Roth IRAs for kids
  • Taxable brokerage accounts
  • Lifetime gifting strategies

I’ll explain:

  • How the new $1,000 government seed contribution works
  • Contribution limits
  • Roth conversion opportunities
  • The “kiddie tax” rules
  • Liquidity restrictions
  • Why many retirees may still prefer flexible brokerage accounts over these new retirement-style accounts for minors.

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. 122: 7 Tax-Free/Efficient Retirement Strategies Every Retiree Needs to Know

Are you approaching retirement with $1 million or more savedand wondering how to minimize taxes on your IRA withdrawals, Social Security income, Roth conversions, brokerage accounts, and retirement income strategy?

In this episode, I’ll break down 7 powerful retirement tax planning strategies that high-net-worth retirees can use to potentially reduce or even eliminate portions of their lifetime tax bill.

You’ll learn:
• How some retirees can take IRA withdrawals tax-free
• Why Roth conversions are often overused
• How the 0% long-term capital gains bracket works
• Strategies to reduce taxes on Social Security income
• Roth IRA withdrawal rules and common mistakes
• Qualified Charitable Distribution (QCD) strategies
• HSA planning opportunities in retirement
• How Net Unrealized Appreciation (NUA) works for company stock

If you are over 50, nearing retirement, or already retired with substantial IRA, 401(k), brokerage, or Roth assets, this episode will help you better understand how retirement tax planning impacts:
• Lifetime income
• Medicare premiums
• RMDs
• ACA subsidies
• Estate planning
• Legacy goals

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. 121: 5 Tax Planning Strategies When You’re High Net Worth, but Poor on Paper

After you retire, you might find your net worth continuing to grow, but your ‘taxable income’ drops significantly. That can create major tax planning opportunities. Hence, ‘High net worth, poor on paper.’

I’ll explain how that period of time can open the door to smarter planning around ACA subsidies, Roth conversions, Social Security taxation, and 0% capital gains harvesting.

Remember, these strategies should not be looked at in a silo. A move that helps in one area can easily impact another if it isn’t coordinated with your full retirement plan.

What you’ll learn in this episode:

  • What “high net worth, poor on paper” actually means
  • Why low-income years in retirement can be powerful planning years
  • How ACA premium tax credits work for early retirees
  • The tradeoff between ACA subsidies and Roth conversions
  • How the Roth conversion window can reduce future RMD problems
  • How Social Security taxation can potentially be reduced with proper timing
  • When 0% capital gains harvesting may make sense
  • Why these strategies must be coordinated, not implemented one by one
  • Why retirement tax planning is about timing taxes wisely, not just avoiding them

Resources / related episodes:
ACA Tax Credits:  The Cliff is Back in 2026:  

$3m Net Worth, Free Healthcare(case study): 

Aggressive Conversions to makeSocial Security Tax Free: 

Thank you for listening!

-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. 120: 5 Retirement Strategies to Protect Your Portfolio During the Iran Oil Crisis

Are you retiring soon or recently retired and worried about market volatility, sequence of returns risk, and what the Iran conflict could mean for your plans?

In this episode, I’m diving into what retirees should be considering as we head into potential prolonged volatility.

I’ll discuss the short term market impact of the conflict.

Then, I’ll touch on what I think might be an underlying long-term goal for the US getting involved.

And most importantly, we’ll touch on 5 strategies to help you prepare for and execute a successful retirement, despite this new wave of uncertainty. I hope it helps!

-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. 119: Social Security for Married Couples: The Survivor Benefit Mistake

If you’re married, your Social Security claiming strategy is not just about your benefit — it’s about protecting your spouse’s income for life. In this video, I’ll explain the most overlooked Social Security rule for married couples and how it can dramatically affect the surviving spouse’s financial security.

Many retirees don’t realize that when one spouse passes away, one Social Security check disappears. The surviving spouse only keeps the larger of the two benefits, which means the higher earner’s claiming decision may be the most important Social Security decision you make.

Using a real-life style example, we’ll walk through how delaying Social Security can significantly increase the survivor benefit, potentially adding thousands of dollars per month for the spouse who lives the longest. I’ll also explain why couples who claim too early may unintentionally reduce the surviving spouse’s income during the most financially vulnerable years of retirement.

However, this strategy doesn’t apply to everyone. I’ll also share three situations where it may actually make sense to ignore the typical advice to delay Social Security, including health considerations, investment strategies, and withdrawal rate concerns.

If you are within 5–10 years of retirement, married, and have saved $1M or more, this Social Security strategy could have a major impact on your long-term retirement income plan.

Enjoy the episode!

~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. 118: Should You Annuitize in Retirement?

Are annuities really that bad?

I’ve spent most of my career skeptical of annuities.  Especially the expensive, complicated products often sold to retirees. I don’t sell annuities. I don’t earn commissions from them. And in most cases, I still am skeptical of how they are ‘sold’and not planned for.

In this episode, I break down four surprising benefits of annuitizing part of your fixed income, especially if you’re approaching retirement with $1M+ saved and want a smarter retirement income strategy.

We’ll cover:

• Why everyone is a bull… until the market drops 10%
• How annuitization can reduce sequence of returns risk
• Why payout rates (like 6%–8%+) is hard to replicate with a ‘safe withdrawal rate’
• How annuities can actually improve legacy outcomes in certain scenarios
• The math behind lowering withdrawal pressure on your equity portfolio
• How to evaluate TIAA Traditional payout options and vintages

Retirement isn’t just about asset allocation.

It’s about income design.

And if you’re over 55, retiring soon, or already retired, understanding annuitization could materially impact your retirement income, stress level, and long-term legacy. Hope you find this useful.

-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. 117: TIAA Traditional Explained: How Much to Keep, When to Use It, and What to Do at Retirement

If you’re a TIAA participant, there’s a good chance you own TIAA Traditional—and it may be one of the most misunderstood “investments” in retirement plans.

In this episode, I’m breaking down TIAA Traditional, TIAA Real Estate and answering the biggest questions I hear from TIAA participants:

✅ Should I own TIAA Traditional?
✅ If so, how much should I keep there?
✅ Should I use the TIAA Real Estate Account?
✅ What should I do with TIAA Traditional after I retire?
✅ Bonus: How do I compare to other retirement savers?

We’ll talk about the real issue most people miss—liquidity and contract type—and how TIAA Traditional can be used as a bond alternative or even as a retirement income floor depending on your plan.

Resources mentioned:

TIAA Real Estate Account

Video, How to get money OUT of TIAA (contract breakdown)

Video, Retirement Savings Relative to Peers

⛳ PFR Nation (Who This Is For)

If you’re over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place.

💬 Comment Below

What is your biggest TIAA question?

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. 116: Are You Stuck in “One More Year Syndrome”?

Lately, I’ve been seeing a TON of retirement planning content telling people:

“Don’t work another year. Retire now. You’re wasting time.”

And honestly… as a retirement-focused financial planner, that message kind of rubs me the wrong way.

Not because it’s always wrong… but because I think there’s an angle behind it.

In today’s episode, we break down what One More Year Syndrome really is, why it’s become such a popular retirement planning trend on YouTube and podcasts, and why you may want to take this advice seriously… but also why you might need to take it with a grain of salt.

Because retirement isn’t just about sitting on the beach 7 days a week.

Retirement should be about purpose, meaning, freedom, and using your time, talents, and treasure in the way that matters most.

I also share a powerful story from a recent conversation with a prospective client who reached out after losing three of his closest friends last year, and how that kind of wake-up call can completely change the way you think about retirement timing.

At the end of this episode, I give you 3 questions to ask yourself to determine whether you’re truly delaying retirement for financial reasons… or if you’re simply afraid of stepping into the unknown.

If you’re in your 50s or early 60s, have saved $1M+ for retirement, and you’re wondering whether you should retire now or work longer, this episode is for you.

✅ Questions Covered In This Episode:

  • Should I retire now or work one more year?
  • Is One More Year Syndrome real?
  • How do I know if I’m financially ready to retire?
  • How do I find purpose after retirement?
  • What if I retire too early?
  • What if I wait too long and regret it?

⛳ PFR Nation (Who This Is For)

If you’re over 50, have saved seven figures (or multiple seven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place.

💬 Comment Below:

Are you stuck in “one more year syndrome”?

What’s holding you back from retiring today — taxes, market uncertainty, healthcare, or fear of the unknown?

I’d love to hear from real retirees and pre-retirees.

⁠⁠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.

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