Advertise on podcast: Retire Smarter with Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®

As you get closer to retirement, it’s usually not one big mistake that throws things off — it’s a handful of smaller decisions that can quietly add up over time. In this episode, Tyler Emrick, CFA, CFP®, walks through five of the most common money moves near retirees make and what to be thinking about instead as you transition into retirement. We cover: Why your investment strategy needs to change as you shift from saving to spending How tax planning becomes more important once you’re no longer relying on a W-2 The impact of Social Security timing decisions, especially for married couples The risks of taking on more investment risk to “catch up” And how healthcare costs — both before and after Medicare — can affect your plan If you’re within a few years of retirement, this episode will help you avoid some of the most common pitfalls and make more intentional decisions with your money. 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

Most people get their tax return back, sign it, and move on. But your 2025 tax return is more than a summary of last year — it’s a roadmap for smarter tax planning going forward. In this episode, Tyler Emrick, CFA, CFP®, walks line-by-line through the key parts of your return and shows you exactly what to look for, including: Where interest income may be creating unnecessary tax drag How dividends and capital gains impact your tax bill (and what to do about it) Why your Adjusted Gross Income (AGI) drives decisions like IRMAA, IRA eligibility, and Roth strategies When it makes sense to itemize vs. take the standard deduction How to use your taxable income to identify Roth conversion opportunities and manage tax brackets Whether you’re approaching retirement or already there, this episode will help you turn your tax return into a planning tool — not just paperwork. If you have your return handy, follow along and see how these strategies apply to your situation. 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

Backdoor Roth IRA explained (2026): how high-income earners can legally contribute to a Roth IRA, step-by-step, and avoid the pro-rata rule tax trap.   If your income is too high to contribute directly to a Roth IRA, the Backdoor Roth strategy is one of the most important ways to still build tax-free retirement income—but it has to be done correctly.   In this episode, we break down: 2026 Roth IRA income limits and contribution limits How the Backdoor Roth IRA works step-by-step How to make a non-deductible IRA contribution and convert it to Roth The pro-rata rule and how it can trigger unexpected taxes How to handle existing Traditional, SEP, or SIMPLE IRA balances When a spousal Backdoor Roth makes sense 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

Trump Accounts explained (2026): how they work, who qualifies for the $1,000 government contribution, and whether they’re actually worth using compared to a 529 plan, Roth IRA, or custodial account. Trump Accounts are a new investment account for kids created under 2025 legislation. The accounts promise $1,000 in initial funding from the government and allow up to $5,000 per year in contributions, but the tax treatment is very different from other strategies families are used to. In this episode, we break down: What Trump Accounts are and how they work Who qualifies for the $1,000 government contribution (2025–2028 births) Contribution rules, including employer and third-party funding How withdrawals are taxed (ordinary income vs capital gains) Trump Accounts vs 529 plans, Roth IRAs, and custodial brokerage accounts 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

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth If you’ve inherited an IRA, the rules have changed — and getting them wrong can be costly. The SECURE Act replaced the old “stretch IRA” with a 10-year distribution rule for most non-spouse beneficiaries, creating new complexity around when and how withdrawals must be taken. Many beneficiaries don’t realize that in some cases, required minimum distributions (RMDs) still apply within that 10-year window. In this episode, Tyler Emrick, CFP®, CFA®, breaks down how the 10-year rule works, who it applies to, and the key mistakes that can lead to unnecessary taxes and penalties. Tyler covers: How the 10-year rule works for inherited IRAs When annual RMDs are required — and when they’re not Exceptions for eligible designated beneficiaries Key considerations when a trust is named as beneficiary Tax planning strategies to avoid bracket creep 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

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Social Security is often treated as a simple decision — pick an age and file. But for couples, it is much more than that. In this episode, Tyler Emrick, CFP®, CFA®, explains how Social Security decisions should be coordinated between spouses and why the timing of those decisions can impact your retirement income by $100,000 or more. With growing concerns around system changes and long-term funding, making the right decision matters more than ever. Tyler covers: The three types of Social Security benefits couples need to understand Why the higher earner’s decision has the biggest long-term impact How to coordinate timing between spouses Key considerations like working while claiming and the earnings test   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

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. 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

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. http://bit.ly/calltruewealth

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

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

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

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

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

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

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