Retire Smarter with Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®

Tax-Efficient Investing 2026: How to Cut Your Tax Bill by Thousands This Year

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Most investors focus on returns. Smart investors focus on what they keep after taxes.
In this episode of Retire Smarter, we break down how two portfolios can earn the same return—and still produce dramatically different tax outcomes. This isn’t about predicting markets or chasing performance. It’s about making structural investment decisions that reduce taxes and improve after-tax results in 2026.
We walk through how to use tax-loss carryforwards intentionally, including how they interact with capital gains, Roth conversions, and rebalancing decisions—and why waiting indefinitely to realize gains is often a costly mistake. We also cover asset location strategy, explaining why where you hold investments (taxable, tax-deferred, or Roth) often matters more than the investments themselves.
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
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Here’s some of what we discuss in this episode:
💰 Why after-tax returns matter more than headline performance
📉 Using tax-loss harvesting and carryforwards effectively
📍 Asset location: what belongs in taxable, IRA, and Roth accounts
🏦 The hidden tax impact of cash and high-yield savings accounts
🩺 How investment income affects Medicare IRMAA and healthcare costs
 
Our website:  https://www.truewealthdesign.com/ 
Phone: 855.TWD.PLAN
Contact our team: https://www.truewealthdesign.com/contact-a-financial-advisor/ 
Schedule your no-cost discovery call: http://bit.ly/calltruewealth 
Check out our other no-cost financial resources here: https://www.truewealthdesign.com/financial-resources/ 
Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

Retirement Planning 2026: The January Decisions That Shape Your Future

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth
In this episode of Retire Smarter, Tyler Emrick, CFA®, CFP®, walks through a practical Retirement Planning Checklist for 2026, focused on the financial moves that matter most in the first few weeks of the year. From front-loading 401(k) and HSA contributions to planning Roth conversions, setting up Qualified Charitable Distributions, and rebalancing after a strong 2025, we break down what to do—and what mistakes to avoid.
If you want to start 2026 with confidence—and avoid scrambling at tax time—this checklist is your roadmap.
Here’s some of what we discuss in this episode:
✅ January is the ideal time to reassess contributions, withdrawals & tax strategies
🔄 Retirees: map out your 2026 withdrawal strategy early
🔁 Split Roth conversions across the year for flexibility & potential tax efficiency
🎯 Use QCDs (Qualified Charitable Distributions) to lower taxable income after 70½
💸 Revisit cash positions: are they still yielding competitive returns?
📉 Consider rebalancing or realizing gains early to get ahead of tax strategy
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
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How TALS Help You Reduce Taxes and Stay Invested (The Full Series)

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Over the past month, we released a six-part video series breaking down how ultra-wealthy investors think about taxes, and more importantly, how they legally minimize them.
In this episode, we’ve stitched the entire Tax-Aware, Long-Short (TALS™) Strategy series together to allow you to hear the full framework in one place, and we’re making it our year-end podcast episode. We’ll talk about why traditional tax strategies fall short for high earners, how advanced tax-aware investing actually works, and the investment structures that have historically been reserved for ultra-high-net-worth families but are now becoming accessible to more investors.
If you want to see the charts, visuals, and examples that go along with this discussion, you can watch the full six-part video series on YouTubehere: https://www.youtube.com/playlist?list=PLz7lSTNSHng4fplwiwAD_26ou4CCU_GP-
 
Here’s some of what we discuss in this episode:
🧠 Understand how TALS generate real tax alpha
💼 When the strategy is best used and when it’s not
📉 Pairing with trader fund structure = business losses
❌ Why most CPAs and advisors miss this
💬 Real-world examples and implementation tips
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
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How You Should Be Using Roth Accounts: Before and After Retirement

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Roth IRAs and Roth 401(k)s are powerful tools — but most people use them without a clear strategy. In this episode, Tyler Emrick, CFA®, CFP®, breaks down how to think about Roth accounts before retirement, after retirement, and even how they impact your spouse and your legacy.
We’ll explore how to decide between pre-tax and Roth contributions while you’re still working, why your tax bracket today may not be your tax bracket in the future, and how early retirees can position assets to maximize ACA healthcare credits
Then, in retirement, we dive into one of the biggest planning questions: Should you prioritize Roth conversions or taxable gain harvesting? We explain the differences, how each affects your tax bill, and why IRMAA, NIIT, and future cash-flow needs all play a major role.
Here’s some of what we discuss in this episode:
🔍 Roth 401(k)s ≠ Roth IRAs - No income limits inside employer plans — huge advantage.
📊 Tax Bracket Targeting - Use your future bracket to decide Roth vs. pre-tax.
🏥 Near 65? Watch ACA Rules - Roth savings can preserve subsidies pre-Medicare.
🔄 Conversions After Retirement - Pay taxes strategically when income drops.
👩‍❤️‍👨Protect the Surviving Spouse - Single tax brackets + IRMAA penalties make Roths crucial.
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
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How Long Will Your Money Last? The Real Math Behind Retirement Success

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Most retirees worry about whether their money will last—but few understand the real variables that determine success. In this episode, we go beyond the usual “spend less, earn more” advice and unpack the math that truly drives a sustainable retirement: the rate of return you actually need, how to stress-test your portfolio against bear markets, and why flexible withdrawals can extend the life of your nest egg.
Tyler Emrick, CFA®, CFP®, walks through how a real financial plan uses Monte Carlo simulations, withdrawal sourcing strategies, and tax-smart distribution planning to give you confidence—even in volatile markets.
If you want your money to last as long as you do, this episode will give you the framework to make smarter decisions today and a stronger plan for tomorrow.
Here’s some of what we discuss in this episode:
📉 Do You Know Your Required Return? Most people don’t — yet it determines your entire investment strategy.
📊 Sequence-of-Return Risk - What happens if you retire into a 2008-style crash?
🔍 Monte Carlo Simulations - Not a Formula 1 race — a tool that models thousands of possible retirements.
🧮 Retirement Smile Concept - Why your spending won’t stay the same over 30 years.
💸 Smarter Withdrawals - The order of withdrawals can save thousands in taxes.
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth
 
Our website:  https://www.truewealthdesign.com/ 
Phone: 855.TWD.PLAN
Contact our team: https://www.truewealthdesign.com/contact-a-financial-advisor/ 
Schedule your no-cost discovery call: http://bit.ly/calltruewealth 
Check out our other no-cost financial resources here: https://www.truewealthdesign.com/financial-resources/ 
Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

How to Get A $25,262 Healthcare Tax Credit Even If You Are Affluent

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For many retirees, healthcare costs before Medicare can be one of the biggest financial shocks — often exceeding $25,000 a year. But with the right planning, that same $25,000 can turn into a tax credit instead of an expense.
In this episode, Tyler Emrick, CFA®, CFP® dives into how the Affordable Care Act’s (ACA) Premium Tax Credits work, what is and what isn't expiring after 2025, and how affluent retirees can still qualify through smart income control. From understanding Modified Adjusted Gross Income (MAGI) to leveraging Roth accounts and taxable savings, you’ll see how advanced tax planning can make a big difference in bridging the healthcare gap to Medicare.
Listen to learn:
How the ACA subsidy formula really works
The “$1 cliff” that can cost you $17,000 or more
Which income sources to use — and avoid — in early retirement
How to coordinate investment, tax, and income strategies to seek maximum benefits
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth
 
Our website:  https://www.truewealthdesign.com/ 
Phone: 855.TWD.PLAN
Contact our team: https://www.truewealthdesign.com/contact-a-financial-advisor/ 
Check out our other no-cost financial resources here: https://www.truewealthdesign.com/financial-resources/ 
Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

Gift Smarter: Tax-Wise Giving to Family and Charity

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth
In this episode of Retire Smarter, Tyler Emrick, CFA®, CFP®, breaks down how to gift smarter — whether your goal is to support family or give back to charity.
With the One Big Beautiful Bill Act (OBBBA) reshaping charitable deductions starting in 2026, now is the time to rethink your strategy. Tyler explains why cash may not be the best asset to give, how Donor-Advised Funds (DAFs) and Qualified Charitable Distributions (QCDs) can maximize your tax efficiency, and what to know about new AGI floors and deductions.
If you want to make your generosity go further — for your loved ones, your favorite causes, and your long-term financial plan — this episode will help you do just that.
Here’s some of what we discuss in this episode:
💸 Cash isn’t king – Gifting appreciated assets can save you (and your kids) significant taxes.
🎁 Donor-advised funds – Get the deduction now, give later, and simplify your recordkeeping.
🙌 QCD advantage – Over 70½? Give directly from your IRA and reduce taxable income.
🧮 Annual limits – Gift up to $19,000 per person (or $38,000 per couple) tax-free each year.
👨‍👩‍👧 Family strategy – Thoughtful planning builds multi-generational wealth and avoids tax traps.
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
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Structure Matters for Tax Efficiency: From Mutual Funds, ETFs, SMAs to Tax-Aware Long-Short

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth
Most don't realize how important structure and strategy impacts an investment's tax efficiency.
Tyler Emrick, CFA®, CFP®, breaks down how investment vehicles — from mutual funds to ETFs, Direct Indexing, and Tax-Aware Long/Short (TALS™) strategies — impact your after-tax returns.
Learn why mutual funds can surprise you with taxable distributions, how ETFs use in-kind redemptions to avoid them, what SMAs are and how they may help, and how modern innovations like long-short overlays unlock new levels of tax efficiency.
Here’s some of what we discuss in this episode:
💼 Investment structure matters – How mutual funds, ETFs, and more advanced vehicles impact your tax bill.
📈 ETFs = efficiency – Learn how they avoid unwanted capital gains distributions.
🔄 Tax loss harvesting – The strategy behind realizing losses for long-term tax benefits.
🧮 Direct indexing – Owning individual stocks for customized control and better tax outcomes.
⚙️ Tax-aware long-short investing – The next evolution in creating ongoing, flexible tax advantages.
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth

Year-End Tax Planning & Tax-Smart Retirement Withdrawal Strategies

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth
It will soon be that time of year again … the fourth quarter. Before you get swept up in the holiday season, it’s the perfect time to take stock. Have you accomplished the financial goals you set for yourself this year? If not, there’s still time to act.
In this episode, Tyler Emrick, CFA®, CFP®, walks you through True Wealth Design’s year-end tax and investment review process — our end of the year tax focused meeting to help families stay on track. You’ll hear what we look for in these meetings, the common year-end items you should be reviewing, and the key decisions that can save you money on taxes. We’ll also highlight why it’s just as important to look ahead — from contribution limits and healthcare enrollment to income targets for the coming year — so you’re prepared for 2026 and beyond.
Here’s some of what we discuss in this episode:
📑 Filing vs. planning – April files the return; December sets the strategy.
💰 Max out contributions – 401(k), HSA, IRA, and catch-up opportunities.
🎁 Charitable giving – Donor-advised funds and bunching strategies can cut your tax bill.
🏥 Healthcare choices – Open enrollment decisions can save thousands.
🧾 Legislative updates – New senior deduction and higher SALT cap change the math in 2025.
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth
 
Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

$1M Saved for Retirement – Can I Retire?

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In today’s episode, we’re tackling the big question: Can you really retire with $1 million? 
We’ll look at what the data says about how much people actually have saved
How other assets like Social Security and pensions fit in, why your spending patterns matter more than you think
Then we will finish up with the key planning opportunities — that can make all the difference.
If you’ve ever asked yourself, “Do I really have enough to retire?” this episode will help you cut through the noise, understand the numbers, and feel more confident about your retirement readiness.
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 20-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth