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

Hosted by Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®

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209

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Jun 2026

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About the show

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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60 recent

June 11, 2026Episode 21419 min

How to Rebalance a Highly Appreciated Portfolio Without Selling: The 351 Exchange Strategy

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Many investors have highly appreciated stocks and ETFs they would like to diversify, simplify, or replace, but selling those investments can create a significant capital gains tax bill. In this episode, Tyler Emrick, CFA®, CFP®, discusses the 351 Exchange Strategy, a little-known tax-efficient planning opportunity that may allow investors to exchange appreciated stocks and ETFs into a diversified ETF without first selling and realizing capital gains taxes. Tyler covers: What a 351 Exchange is and how it works The difference between a 351 Exchange and a traditional exchange fund Rules investors must satisfy before qualifying Which assets qualify and which assets do not ETF eligibility requirements How highly appreciated ETF portfolios may be consolidated into a diversified ETF How concentrated stock positions may fit into a 351 Exchange strategy The potential benefits of reducing concentration risk without immediately triggering capital gains taxes How 351 Exchanges compare to tax-aware long-short strategies and other tax-efficient diversification techniques 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

June 4, 2026Episode 21315 min

So You’ve Decided To Do A Roth Conversion… Now What?

So you’ve decided to do a Roth conversion… now what? Most Roth conversion conversations focus on whether you should do one. But the long-term value often comes from how the strategy is actually implemented. In this episode, Tyler Emrick, CFA®, CFP® walks through the overlooked decisions that can materially impact the outcome of a Roth conversion strategy. Topics include: When to complete a Roth conversion Whether to spread conversions throughout the year Tax bracket management and conversion timing Why recharacterizations no longer being available matters How to pay Roth conversion taxes efficiently Roth conversions before age 59½ Estimated tax payments and withholding strategies Which investments may be best suited for Roth accounts Why higher-growth investments are often prioritized inside Roth IRAs Coordinating Roth conversions with investment management and rebalancing Tyler also explains why many Roth conversion mistakes have less to do with the conversion itself — and more to do with poor timing, tax management, and implementation decisions. 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/ Facebook: https://www.facebook.com/TrueWealthDesign/ LinkedIn: https://www.linkedin.com/company/true-wealth-design/ X: https://x.com/truewealthdesgn Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

May 28, 2026Episode 21219 min

The Biggest Investment Mistakes Aren’t What You Think

Investment management is often framed around picking stocks, predicting markets, and finding outperforming investments. But many of the decisions that have the biggest long-term impact on investor outcomes come from diversification, tax strategy, portfolio construction, and how investments are implemented over time. In this episode, Tyler Emrick, CFA®, CFP®, discusses the often-overlooked side of investing and why portfolio management involves much more than simply picking investments. Topics covered include: Why diversification still matters despite years of U.S. market dominance Emerging markets outperformance and the importance of global exposure How ETFs and asset location can improve after-tax returns Asset location strategies across taxable and retirement accounts Public REIT dislocations and investment vehicle structure considerations Managing concentrated stock positions more tax efficiently Donor-advised funds, QCDs, and gifting appreciated securities Tax-aware long/short strategies and multi-year planning The “architecture before allocation” philosophy at True Wealth Design Tyler also explains how coordinated planning across investments, taxes, retirement income, estate strategy, and charitable giving can help improve long-term outcomes. 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/ Facebook: https://www.facebook.com/TrueWealthDesign/ LinkedIn: https://www.linkedin.com/company/true-wealth-design/ X: https://x.com/truewealthdesgn Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

May 21, 2026Episode 21122 min

Is Your Retirement Advice Already Too Late? Why Proactive Planning Matters

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth This episode walks through what proactive financial planning actually looks like beyond investment management alone. Tyler Emrick, CFA, CFP® breaks down how ongoing advice should work for retirees and pre-retirees, including the structure of our Progress Meetings, Tax & Investment Review Meetings, and the ongoing planning conversations that happen throughout the year as life changes. We also discuss why coordinated planning matters so much as retirement decisions become more interconnected — from Roth conversions and tax planning to Medicare, Social Security, estate planning, spending goals, and retirement income strategies. In this episode: What proactive financial planning actually means Why preparation matters in advisor meetings The difference between investment management and true financial planning How we help families navigate retirement transitions and major life decisions Roth conversion mistakes and tax planning coordination Why written recommendations and ongoing advice matter How taxes, investments, healthcare, and estate planning all work together As retirement approaches, small financial decisions can have larger long-term consequences. The goal of proactive planning is helping families make informed decisions before those mistakes become expensive later. 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

May 14, 2026Episode 21017 min

Is Your Financial Plan Doing Its Job? (3 Things to Check)

Most financial plans get built once, put in a drawer, and rarely used again. But real financial planning should actively help guide decisions throughout retirement. In this episode, Tyler Emrick, CFA, CFP® walks through three practical ways your financial plan should actually be helping you right now: investment decisions, spending decisions, and income & distribution planning. We discuss: How to understand your true household allocation and risk exposure Why many retirees naturally drift into an “all cash, all stocks” portfolio Asset location and using different accounts efficiently Required portfolio return and bear market testing Dynamic spending throughout retirement How strong markets can impact spending and gifting decisions Roth conversions, IRA distributions, capital gains, and tax planning Why retirement income planning is much bigger than simply withdrawing money from accounts As retirement gets closer, every financial decision starts affecting the next one. The goal of a financial plan should not simply be to exist — it should help families make better decisions over time. 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

May 7, 2026Episode 20916 min

Why Most Financial Plans Fail (And How To Build A Better One)

Most people think a financial plan is a set of projections… a retirement number… or a long report that tells you whether you’re going to be okay. In reality, many of those plans end up as 60–90 page documents that sit on a shelf and rarely get used. But a real financial plan should do a lot more than that. In this episode, we walk through what a financial plan should actually do, especially for pre-retirees and retirees making important decisions around retirement, taxes, income, and long term planning. We cover: What most financial plans focus on and where they fall short How a real plan connects taxes, income, investments, healthcare, and estate planning Why spending and life transitions are critical to building a plan that actually works How a financial plan becomes a decision making tool, not just a report A real example of how planning helps navigate an unexpected life change 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

April 30, 2026Episode 20819 min

What a First Meeting with a Financial Advisor Should Look Like

Most people walk into their first meeting with a financial advisor expecting a presentation—charts, investments, maybe even a pitch. But a real discovery meeting shouldn’t feel like that at all. In this episode, we break down what a first meeting with a financial advisor should actually look like, especially for pre-retirees and retirees trying to make important decisions around retirement, taxes, income, and long-term planning. We walk through: What typically happens in a real discovery meeting What most people expect vs what actually happens How to tell if an advisor is taking a holistic financial planning approach or just focusing on investments Real client examples—from families who didn’t know where to start to those who had an advisor but weren’t getting coordinated advice The biggest red flags to watch for when meeting with a financial advisor 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

April 23, 2026Episode 20722 min

5 Worst Money Moves to Avoid Before Retirement

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

April 16, 2026Episode 20622 min

Your Tax Return Is a Blueprint — Here's How to Use It for Better Planning

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

April 9, 2026Episode 20522 min

Backdoor Roth IRA Explained: How High Earners Avoid Income Limits

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