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

How to Diversify Concentrated Stock Without a Big Tax Bill

A strong market can create a new problem. A single stock or ETF grows to represent a large portion of your net worth. Now you face a difficult tradeoff: diversify and trigger a large tax bill, or hold the position and accept concentrated risk.
In this episode, Tyler Emrick, CFP®, CFA®, walks through practical strategies for managing concentrated stock positions in a tax-efficient way.
You will learn:
How a Section 351 exchange into an ETF can provide diversification while deferring capital gains
How tax-aware long-short strategies can help create ongoing tax offsets while gradually reducing a concentrated position
When Net Unrealized Appreciation may apply to company stock inside a 401k
How donor-advised funds and charitable planning can reduce capital gains on appreciated shares
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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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/ 
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The Retirement Spending Myth: Why the 80% Rule Gets It Wrong

Most retirement plans assume your spending will stay flat, or that you will need about 80 percent of your pre-retirement income.
But retirement does not actually work that way.
In this episode, Tyler Emrick, CFP®, CFA®, explains what the research shows about how retirement spending changes over time and why relying on outdated rules like the 80 percent rule can lead to over-saving and under-living or under-planning altogether.
Drawing on research from David Blanchett’s Retirement Spending Smile, Morningstar data, and EBRI studies, Tyler covers:
Why retirement spending is not a straight line
How spending often declines in mid-retirement and rises again later
The Go Go, Slow Go, and No Go phases of retirement
How fear of running out of money causes many retirees to under-spend
A practical way to estimate your real retirement spending needs
 
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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Why Most People Are Wasting Their HSA (And How to Fix It)

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Health Savings Accounts (HSAs) may be the most powerful tax-free retirement planning tool available, yet most people use them completely wrong.
If you’re enrolled in a High Deductible Health Plan (HDHP), your HSA could offer triple tax-free growth and a strategic way to fund healthcare and Medicare costs in retirement.
Tyler Emrick, CFA®, CFP®, breaks down how to turn your HSA from a simple medical spending account into a long-term, tax-efficient retirement asset.
In this video, you’ll learn:
HSA eligibility rules, 2026 contribution limits, catch-up contributions, and the December “last-month rule”
How High Deductible Health Plans qualify you to contribute
Why leaving your HSA in cash limits long-term growth
How to invest your HSA using brokerage options
The “invest now, reimburse later” strategy to build tax-free retirement liquidity
How HSAs can cover Medicare premiums, COBRA coverage, long-term care premiums, and other retirement healthcare costs
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

The RMD Tax Trap: Required Minimum Distribution Strategies That Lower Lifetime Taxes

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Required Minimum Distributions (RMDs) are not just mandatory withdrawals — they are forced taxable income that can quietly reshape your retirement tax picture.
Higher income from RMDs can trigger increased marginal tax rates, IRMAA surcharges, greater Social Security taxation, and long-term compounding tax consequences — especially for married couples navigating the widow/widower tax penalty.
In this episode, Tyler Emrick, CFA®, CFP®, breaks down how to think about RMD tax planning as a long-term process — not just a once-a-year withdrawal decision — including:
Why RMD planning is really tax bracket management over time
How Roth conversions can shrink future Required Minimum Distributions
Smart timing and withholding strategies that create flexibility
How Qualified Charitable Distributions (QCDs) reduce taxable income
The role of income targeting and IRMAA awareness
What types of assets to convert — and why it matters
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

Tax Filing Season 2026: Last-Minute Planning Moves for Individuals and Business Owners

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Tax filing season is here — and even though most tax planning happens before year-end, there are still important moves you can make before filing your 2025 return.
In this video, Tyler Emrick, CFA®, CFP®, walks through last-minute tax planning moves that still matter during the 2026 filing season for individuals and business owners. We cover what you can still do before filing, how to avoid penalties and surprises, and several common items that often get missed — especially for small business owners and self-employed individuals.
Here’s some of what we discuss in this episode:
🧾 HSA and IRA contributions you can still make for last year
⏳ Why income limits matter before funding Roth or IRA accounts
🏦 Safe harbor rules, extension payments, and avoiding penalties
🏢 Business owner deadlines, S-corp elections, and retirement plans
🔍 Common filing mistakes: 1099 errors and excess contributions
 
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

Retirement Cash Reserves in 2026: How Much Is Enough?

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How much cash should you really hold in retirement?
Too little cash can create stress and force poor decisions during market downturns. Too much cash can quietly erode a well-built retirement plan through inflation, taxes, and lost growth.
In this episode, Tyler Emrick, CFA®, CFP®, breaks down how to think about retirement cash reserves in 2026, including:
How much cash is actually enough in retirement — and when it becomes too much
How interest rates change the cash trade-off in 2026
Where cash really lives inside a well-built portfolio (not just checking and savings accounts)
This conversation is designed for people approaching retirement or already retired who want to make smarter, more intentional cash decisions — without chasing yields or taking unnecessary risk.
 
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

The 2026 Gift Tax Rules Explained: How to Gift Cash, Stock, and Family Loans Correctly

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Many parents and grandparents want to help family financially, but gift tax rules are often misunderstood.
In this episode, Tyler Emrick, CFA®, CFP®, breaks down the 2026 gift tax rules in plain English, including how much you can give without triggering tax, when gifting appreciated stock makes sense, and how to properly structure family loans using IRS guidelines. We also explain when a gift tax return is required—and why filing one doesn’t necessarily mean you’ll owe tax.
If you’re considering gifting money to children or grandchildren, this episode will help you do it the right way.
Here’s some of what we discuss in this episode:
🧾 Gifts over the limit require filing IRS Form 709
🧱 Using appreciated stock instead of cash to potentially lower taxes
📉 Kids in lower tax brackets can sell gifted stock at reduced or zero tax
📝 Family loans are an alternative to large gifts and offer more control
🧠 Gifting strategy should consider estate size, tax brackets, and family dynamics
 
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

How Much Can You Spend in Retirement? A Smarter Take on the 4% Rule

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For decades, the 4% rule has been used as a simple guideline for retirement spending—but it was never meant to be a guarantee.
In this episode, Tyler Emrick, CFA®, CFP®, will revisit the research behind the 4% rule and explore new findings from its creator, Bill Bengen, suggesting that retirees may be able to spend more under updated assumptions. We explain why sequence-of-returns risk matters more than average returns, how thinking in terms of portfolio “runway” can help manage downturns, and why dynamic withdrawal strategies often lead to better long-term outcomes.
If you’re wondering how much you can realistically spend in retirement, this episode will help you think about it the right way.
Here’s some of what we discuss in this episode:
🔄 Retirement spending should be dynamic, not static
🧱 Diversification and flexible withdrawal strategies help weather market downturns
🛫 A “runway” of preservation assets (cash/bonds) buys time during volatility
🔧 Rebalancing and spending flexibility are critical to long-term success
💬 Planning should be annual, adaptive, and personalized—not one-and-done
 
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

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.
http://bit.ly/calltruewealth
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

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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.
http://bit.ly/calltruewealth