Planning for Retirement with Kevin Lao

Kevin Lao
  • 4.9 (29)
  • Investing
  • Updated Biweekly

After more than 17 years serving retirees, I’ve seen the same pattern: people spend 30–40 years building wealth, but the biggest financial decisions happen right before and after retirement. I’m Kevin Lao, a fiduciary financial advisor specializing in retirement income planning, Roth conversions, Social Security, tax strategies, RMDs, and smart investing for those with $1M+ saved. If you’re within 10 years of retirement or already retired and want clarity, confidence, and tax-efficient income, this podcast is for you. Bonus points if you love golf!

  1. 2d ago

    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. 📌 Topics Covered: Roth Conversion StrategiesRetirement Tax PlanningIRA to Roth IRA ConversionRMD PlanningTax-Efficient Retirement IncomeSECURE Act & Inherited IRAsRetirement Planning for High Net Worth RetireesMedicare IRMAA PlanningSocial Security TaxationFinancial Planning for Retirees👇 If you enjoyed this episode:✅ Subscribe for weekly retirement planning videos✅ Leave a 5-star review on Spotify or Apple Podcasts✅ Share this with someone nearing retirement 📞 Want help building a retirement tax strategy? ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Clickthis link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Connect with me here: YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠JoinMy Company Newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

    31 min

  2. May 19

    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 arethinking about: helping children or grandchildrenfinancially, reducing future estate taxes, gifting while living, or 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 and lifetime gifting strategies. I’ll explain: how the new $1,000 government seedcontribution works, contribution limits, Roth conversion opportunities, the “kiddie tax” rules, liquidity restrictions, and why many retirees may stillprefer flexible brokerage accounts over these new retirement-style accounts forminors. ⁠Are you interested inworking with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement ReadinessQuestionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multipleseven figures), love golf and travel, and you want to make work optional whileminimizing taxes… welcome to the right place. 💬 Comment Below: Are you prioritizing a Trump Account over other alternatives?   Connect with me here: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Follow the podcast ​⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠JoinMy Company Newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

    36 min

  3. May 12

    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 retiredwith substantial IRA, 401(k), brokerage, or Roth assets, this episode will help you better understand how retirement tax planning impacts: 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, • and legacy goals. ⁠Areyou interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Clickthis link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multipleseven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place. 💬 Comment Below with one or two major takeaways from this episode! This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

    36 min

  4. Mar 24

    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 thedoor 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 asilo. 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 If you want help building a retirement plan thatcoordinates investments, taxes, income, and leaving a legacy, you can learnmore at www.imaginefinancialsecurity.com Or, start with requesting a Mutual Fit Meeting by filling out this shortquestionnaire: https://form.jotform.com/250847998463173   Resources / related episodes:ACA Tax Credits:  The Cliff is Back in 2026:  https://youtu.be/iZcF5IuH1Bg?si=x5l4SnH2nl3wnYS1 $3m Net Worth, Free Healthcare(case study): https://youtu.be/iZcF5IuH1Bg?si=x5l4SnH2nl3wnYS1 Aggressive Conversions to makeSocial Security Tax Free: https://youtu.be/oeo3jT5iUbQ If you enjoyed this episode Please leave a 5-star review, follow the show, and shareit with someone who is close to retirement or recently retired. Thank you! -Kevin

    44 min

  5. Mar 17

    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 Request A “Mutual Fit Meeting” here ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multipleseven figures), love golf and travel, and you want to make work optional while minimizing taxes… welcome to the right place. ***This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

    35 min

  6. Mar 10

    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, Kevin walks 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. He also explains 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. ⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ 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. This is for general education purposes only and should not be considered as tax, legal or investment advice.

    8 min

  7. Mar 3

    118: Should You Annuitize in Retirement? 4 Surprising Benefits

    Are annuities really that bad? I’ve spent most of my career skeptical of annuities.  Especially the expensive, complicatedproducts 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 ofannuitizing 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 withdrawalrate’ • 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?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ PFR Nation (Who This Is For) If you're over 50, have saved seven figures (or multipleseven figures), love golf and travel, and you want to make work optional whileminimizing taxes… welcome to the right place.   This is for general education purposes only and shouldnot be considered as tax, legal or investment advice.

    14 min

  8. Feb 24

    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 ⁠Are you interested in working with me 1 on 1?⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Click this link to fill out our Retirement Readiness Questionnaire⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Or,⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠visit my website⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠   ⛳ 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!?   This is for general education purposes only and should not be considered as tax, legal or investment advice.

    22 min
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About

After more than 17 years serving retirees, I’ve seen the same pattern: people spend 30–40 years building wealth, but the biggest financial decisions happen right before and after retirement. I’m Kevin Lao, a fiduciary financial advisor specializing in retirement income planning, Roth conversions, Social Security, tax strategies, RMDs, and smart investing for those with $1M+ saved. If you’re within 10 years of retirement or already retired and want clarity, confidence, and tax-efficient income, this podcast is for you. Bonus points if you love golf!

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