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

Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®
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Planning Retirement Smarter. Living Retirement Better. With Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP® of True Wealth Design. #Retire #Stocks #Investing #401k #IRA #CFP #TrueWealthDesign. Contact at https://www.truewealthdesign.com/ or by calling 855-893-7526.

  1. 2D AGO

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

    Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth 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

    19 min

  2. FEB 5

    Retirement Cash Reserves in 2026: How Much Is Enough?

    Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth 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

    18 min

  3. JAN 29

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

    Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth 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

    13 min

  4. JAN 23

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

    Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth 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

    27 min

  5. JAN 15

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

    Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth 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

    18 min

  6. JAN 9

    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. http://bit.ly/calltruewealth

    16 min

  7. 12/31/2025

    How TALS Help You Reduce Taxes and Stay Invested (The Full Series)

    Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth 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. http://bit.ly/calltruewealth

    53 min

  8. 12/11/2025

    How You Should Be Using Roth Accounts: Before and After Retirement

    Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth 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. http://bit.ly/calltruewealth

    36 min
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About

Planning Retirement Smarter. Living Retirement Better. With Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP® of True Wealth Design. #Retire #Stocks #Investing #401k #IRA #CFP #TrueWealthDesign. Contact at https://www.truewealthdesign.com/ or by calling 855-893-7526.

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