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

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

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217

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Aug 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

August 13, 2026Episode 22218 min

The Most Important Investment Decision Isn't What You Think

Most investors spend their time deciding what investments to own. Far fewer spend time thinking about where those investments should be held. In this episode, Tyler Emrick, CFA®, CFP®, breaks down one of the most overlooked tax planning strategies in retirement: asset location. Using research from Vanguard, Tyler explains how placing the same investments in different accounts—taxable, traditional IRA/401(k), and Roth—can improve after-tax wealth without taking additional investment risk. In this episode, Tyler covers: What asset location is—and why it's different from asset allocation. Vanguard's research on improving after-tax returns. Where different investments generally belong. Why Roth accounts deserve special consideration. Common mistakes investors make when organizing their portfolios. Why asset location should evolve throughout retirement. 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

August 6, 2026Episode 22319 min

Why Are Retirees So Afraid to Spend Their Money?

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Many retirees spend decades building wealth, only to struggle with using it once they retire. If you've ever wondered, "Can we really afford this?" or found yourself hesitating to spend despite being financially secure, you're not alone. In this episode, Tyler Emrick, CFA®, CFP®, discusses why so many retirees struggle to spend confidently and how ongoing financial planning provides clarity around life's biggest financial decisions. Through real client stories, Tyler explains how retirement planning goes far beyond managing investments—it's about helping people confidently use the wealth they've spent a lifetime building. In this episode, Tyler covers: Why nearly 40% of retirees struggle to spend their savings. The shift from saving for retirement to spending in retirement. Real client stories about relocating and helping adult children financially. Why regular planning reviews create confidence. How a good advisor helps clients evaluate options and make better financial 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

July 30, 2026Episode 22120 min

How Do You Compare? New Retirement Savings Data Is Out

How much should you have saved for retirement? It's one of the most common questions people ask, and new retirement savings data from Fidelity gives us a chance to see how Americans compare. But while the numbers are interesting, they don't answer the most important question: Will your resources support the retirement you want to live? In this episode, Tyler Emrick, CFA, CFP® reviews the latest retirement savings data, explains why averages can be misleading, and shares real-life examples of why income, lifestyle, and thoughtful planning matter more than simply comparing account balances. We discuss: What Fidelity's latest retirement savings data shows by age and generation Why average and median tell two very different stories Why retirement readiness is about much more than your 401(k) balance How pensions and guaranteed income can significantly change the retirement equation Why two families with similar account balances can have completely different retirement outcomes A better way to measure retirement readiness than comparing yourself to everyone else 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

July 23, 2026Episode 22016 min

Can You Retire Before 59½? Here's What You Need to Know

Many people assume they have to wait until age 59½ before they can retire because that's when retirement accounts generally become available without the 10% early withdrawal penalty. But in reality, early retirement is often less about how much you've saved and more about how you access your money. In this episode, Tyler Emrick, CFA, CFP® discusses the planning strategies that can help bridge the gap before traditional retirement account access, why saving across different account types creates flexibility, and how thoughtful income planning can make early retirement a realistic option. We discuss: Why age 59½ matters—and why it doesn't necessarily determine when you can retire Planning opportunities including the Rule of 55, 72(t), and Net Unrealized Appreciation (NUA) Why taxable brokerage accounts, Roth IRA contributions, and cash reserves can create flexibility Building a retirement income bridge before Social Security, pensions, and Medicare begin Healthcare planning before age 65, including COBRA and ACA Marketplace coverage 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/ 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

July 16, 2026Episode 21924 min

How Much Money Is Enough To Retire?

How much money is enough to retire? It may be the most common retirement planning question, but it isn't always the right one. In this episode, Tyler Emrick, CFA®, CFP®, explores why financial security is often more psychological than mathematical and why some retirees with millions of dollars still worry about running out of money. Tyler discusses: Why "enough" often keeps moving Behavioral biases that affect retirement decisions Why many retirees struggle to spend after decades of saving The difference between financial independence and financial confidence Practical ways to think differently about retirement 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

July 9, 2026Episode 21820 min

Going Back to Work in Retirement? Here's What to Know First

More retirees than ever are choosing to work in retirement, whether for additional income, consulting opportunities, or simply because they enjoy staying engaged. In this episode, Tyler Emrick, CFA®, CFP®, discusses the financial planning considerations that often accompany returning to work after retirement. Tyler covers: Social Security earnings limits ACA health insurance before Medicare Medicare and IRMAA considerations How working affects retirement tax planning Deciding whether working is financially and personally worthwhile 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

July 2, 2026Episode 21720 min

The Most Valuable Tax Planning Window in Retirement

Many retirees have a unique period between retirement and the start of Social Security and Required Minimum Distributions (RMDs) when their taxable income may be significantly lower than it will be later in retirement. In this episode, Tyler Emrick, CFA®, CFP®, explains why this retirement tax planning window may be one of the biggest opportunities affluent retirees have to improve lifetime tax efficiency. Tyler covers: Why taxes often increase later in retirement Roth conversion opportunities before RMDs Capital gains harvesting strategies Social Security timing considerations Medicare IRMAA planning The widow's tax trap Why waiting too long can permanently reduce planning flexibility 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

June 25, 2026Episode 21618 min

The New Social Security Report Is Out: What Retirees Actually Need To Know

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth The 2026 Social Security Trustees Report is out, and it is already creating headlines about the future of Social Security benefits. In this episode, Tyler Emrick, CFA®, CFP®, breaks down what affluent retirees and pre-retirees actually need to know about the new Social Security report, including the 2032 trust fund projection, the 2034 combined trust fund projection, and why Social Security is not “going bankrupt.” Tyler covers: What the 2026 Social Security Trustees Report says Why benefits do not disappear if the trust fund is depleted Why the retirement trust fund projection moved to 2032 How much of scheduled benefits may still be payable The most likely Social Security fixes Congress may consider Whether Social Security claiming strategies should change What affluent retirees should focus on instead 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

June 18, 2026Episode 21519 min

Donor-Advised Funds Explained: The Most Underused Tax Strategy for Charitable Retirees

Donor-advised funds have become one of the most popular charitable giving tools in the country, with more than $326 billion now held in donor-advised fund accounts. Yet many retirees and investors still don't fully understand how donor-advised funds work, when they make sense, or how they can fit into a broader tax planning and retirement planning strategy. In this episode, Tyler Emrick, CFA®, CFP®, covers: What a donor-advised fund is and how it works Why donor-advised fund assets have nearly doubled since 2020 How donating appreciated stock can reduce taxes and avoid capital gains Why investment growth inside a donor-advised fund may increase charitable impact over time How charitable bunching strategies can create larger tax deductions Common donor-advised fund mistakes and misconceptions Real-world situations where donor-advised funds may fit into a retirement or tax planning strategy For retirees and investors who regularly support charities, a donor-advised fund can be much more than a charitable account. It can be a tax planning tool, an investment tool, and a way to simplify ongoing charitable giving. 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

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