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

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

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226

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Oct 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

October 16, 2026Episode 23221 min

Don't Automatically Renew Your Medicare Insurance: 5 Things Retirees Need to Check for 2027

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Medicare open enrollment is here, but automatically renewing your current health insurance could be a costly mistake. Your monthly premium is only one piece of the equation. Changes to prescription drug coverage, provider networks, deductibles, and out-of-pocket costs can significantly affect what retirees pay for healthcare. In this episode, Tyler Emrick, CFA®, CFP®, discusses five important things retirees should review before selecting their 2027 health insurance coverage. In this episode, Tyler covers: Why the lowest monthly premium isn't always the best deal. What to review when comparing Medicare Advantage and Original Medicare with Medigap. How prescription drug coverage changes can affect your costs. Why switching Medicare coverage isn't always as simple as it sounds. How retirement income, Roth conversions, and IRA withdrawals can affect healthcare costs. What to check before the Medicare open enrollment deadline. 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

October 8, 2026Episode 23121 min

AI Scams Are Targeting Retirees. Here's How to Protect Your Money.

Financial scams targeting retirees are becoming increasingly sophisticated, and artificial intelligence is making it harder to know whether the person calling, texting, or emailing you is actually who they claim to be. The numbers are significant. Americans age 60 and older reported nearly $7.75 billion in internet crime losses to the FBI in 2025. But protecting yourself isn't simply about learning how to recognize every new scam. It's about putting safeguards around your money before something happens. In this episode, Tyler Emrick, CFA®, CFP®, explains practical steps retirees and their families can take to protect their retirement savings from fraud and financial exploitation. In this episode, Tyler covers: How AI is making impersonation and other financial scams more convincing. Why retirees can be particularly vulnerable to large financial losses. How a security word or phrase can add protection to distribution requests. What a trusted contact is and what authority they do and don't have. Why families should consider establishing their own verification process. Account alerts, multifactor authentication, credit freezes, and other financial safeguards. Warning signs that an aging parent may need more help managing their finances. Why powers of attorney and trusted professionals should be in place before they're needed. 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. 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

October 1, 2026Episode 23018 min

Planning a Significant Charitable Donation? Here's Where the Money Should Come From"

If you're already planning to give money to charity, does it matter which account the money comes from? Absolutely. Retirees may have several ways to fund their charitable giving: cash, appreciated investments, or distributions directly from an IRA. While the charity may receive the same amount either way, the tax consequences can be very different. And new tax rules beginning in 2026 add another layer to the decision. In this episode, Tyler Emrick, CFA®, CFP®, explains how retirees can think more strategically about charitable giving and decide which assets may be most advantageous to give. In this episode, Tyler covers: The new charitable deduction available to non-itemizers in 2026. Why donating appreciated stock can help avoid capital gains. How the new charitable deduction floor affects taxpayers who itemize. How qualified charitable distributions, or QCDs, work after age 70½. Why QCDs can be valuable even if you don't itemize deductions. How future charitable giving can affect IRA withdrawals and Roth conversion planning. How to decide whether cash, appreciated investments, or IRA dollars are the best assets to give. If you're already planning to support the organizations you care about, the question isn't only how much to give. It's which dollars should leave your balance sheet. 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. 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

September 24, 2026Episode 22919 min

Your Retirement Plan Works for Two. Does It Still Work for One?

Does your retirement plan still work if one spouse dies? It's an uncomfortable question, but an important one for every married couple approaching or living in retirement. When one spouse dies, household finances don't simply get cut in half. One Social Security benefit generally disappears, pension income may change, and many household expenses remain. At the same time, the surviving spouse may eventually move from married to single tax brackets, creating what is sometimes referred to as the “widow's tax penalty.” In this episode, Tyler Emrick, CFA®, CFP®, explains what can change financially after the death of a spouse and what couples can do today to better prepare the surviving spouse. In this episode, Tyler covers: What happens to Social Security and pension income after one spouse dies. Why household expenses typically don't fall by 50%. How the “widow's tax penalty” and Medicare IRMAA can affect a surviving spouse. Why tax planning while both spouses are alive can matter later. Why both spouses should understand how their financial life works and know who to call. 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

September 17, 2026Episode 22822 min

Your First Year of Retirement: What You Need to Get Right

You've spent decades preparing for retirement. But what happens once you're actually retired? The first year of retirement is a major transition. Your paycheck disappears, healthcare works differently, your income may come from several different places, and your daily routine can change almost overnight. In this episode, Tyler Emrick, CFA®, CFP®, walks through some of the most important financial and lifestyle decisions new retirees face during their first year of retirement. In this episode, Tyler covers: How to navigate healthcare once employer coverage ends. Different ways to create and manage cash flow without a regular paycheck. How to decide where your retirement spending should come from. Tax-planning opportunities that can emerge after your W-2 income disappears. Why retirement planning shouldn't stop with the financial numbers. How work, purpose, social interaction, and routine can change after retirement. Why your first year of retirement doesn't have to look exactly like you planned. 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. 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

September 10, 2026Episode 22718 min

Retiring in 2027? Don't Pick Your Retirement Date Until You Check These 7 Things

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Thinking about retiring in 2027? Before you pick your last day of work, there are several financial planning opportunities worth considering. Your exact retirement date can affect more than just your final paycheck. Bonuses, pension benefits, employer retirement contributions, health insurance, Medicare, taxes, Social Security, and even Roth conversion opportunities can all be influenced by when you leave your employer. In this episode, Tyler Emrick, CFA®, CFP®, walks through seven things to consider before deciding exactly when to retire. In this episode, Tyler covers: Why your retirement date shouldn't be chosen arbitrarily. Bonuses, stock compensation, pension milestones, and other benefits you could leave behind. How your final paychecks can potentially be used to maximize 401(k) and HSA contributions. Why employer matching and true-up provisions matter. How to bridge health insurance between work and Medicare. Why retiring in December versus January or February can produce different tax-planning opportunities. Why retiring from work and starting Social Security or a pension don't have to happen at the same time. How to balance financial optimization with actually being ready to retire. 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

September 3, 2026Episode 22618 min

Think You're Maxing Out Your 401(k)? The 2026 Rules Just Got More Complicated

Think you're on track to max out your 401(k) this year? The answer may be more complicated than you think. New rules took effect in 2026, requiring certain higher-income workers to make their catch-up contributions as Roth contributions. But employers and retirement plan providers aren't all handling the process exactly the same way. In this episode, Tyler Emrick, CFA®, CFP®, explains what changed and why this is a good year to take a closer look at your employer retirement plan before year-end. In this episode, Tyler covers: The 2026 401(k) contribution and catch-up limits. Who is affected by the new mandatory Roth catch-up rule. Why different employer plans may handle catch-up contributions differently. How to determine whether you're actually on pace to maximize your contributions. Why employer matching and true-up provisions should be part of the calculation. How after-tax 401(k) contributions can allow some employees to save substantially more. How after-tax contributions may be converted to Roth through a Mega Backdoor Roth strategy. Why your employer retirement plan deserves an annual checkup. 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

August 27, 2026Episode 22525 min

You Just Inherited Money. Now What?

You just received an inheritance. Now what? Before you sell investments, take distributions, pay off debt, or make a major purchase, it's important to understand exactly what you've inherited and the tax rules that come with it. In this episode, Tyler Emrick, CFA®, CFP®, walks through the biggest financial decisions that can come with an inheritance and explains why some seemingly simple moves can create unintended tax consequences. In this episode, Tyler covers: What to do first after receiving an inheritance. Why you shouldn't immediately liquidate inherited assets. Tax considerations for inherited brokerage accounts, IRAs, Roth IRAs, annuities, and real estate. How inherited IRA distribution rules can create tax planning opportunities. Why you shouldn't automatically keep the investments you inherit. How an inheritance can create an opportunity to rethink asset allocation and asset location. How an inheritance could change your retirement, tax, estate, and spending plans. 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 20, 2026Episode 22423 min

Do You Need a Trust? Estate Planning 101 for Retirees

Do you need a trust, or is a will enough? And even if your estate documents are complete, are your accounts and beneficiary designations actually set up to follow your wishes? In this episode, Tyler Emrick, CFA®, CFP®, breaks down the estate planning basics retirees should understand. From beneficiary designations and transfer-on-death instructions to wills, revocable trusts, irrevocable trusts, and powers of attorney, Tyler explains how the pieces of an estate plan work together. In this episode, Tyler covers: Why beneficiary designations and account titling should be one of your first estate planning reviews. What a will actually controls and why it doesn't avoid probate. When a revocable living trust may make sense. The key differences between revocable and irrevocable trusts. Why simply creating a trust isn't enough if assets aren't properly coordinated with it. The core estate planning documents retirees should consider. Why communicating your estate plan with family can be just as important as creating it. 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

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