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

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

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229

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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

November 5, 2026Episode 23516 min

4 RMD Mistakes That Could Cost You Thousands in Retirement

Required minimum distributions (RMDs) are an important part of retirement, but simply taking the required amount doesn't mean you're making the best financial decision. In this episode, Tyler Emrick, CFA®, CFP®, and Walter discuss four common RMD mistakes that could create unnecessary taxes or cause retirees to miss valuable planning opportunities. You'll learn: When you can combine RMDs across IRAs and why 401(k)s follow different rules How qualified charitable distributions (QCDs) can help reduce taxable retirement income Why inherited IRA rules differ depending on who inherits the account How eligible designated beneficiaries may qualify for life-expectancy distributions Why Roth conversions and other tax-planning opportunities don't necessarily end when RMDs begin 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 29, 2026Episode 23421 min

2026 Year-End Tax Planning: 5 Things Retirees Need to Check Before December 31

The end of the year is approaching, and for retirees, some of the most valuable tax-planning opportunities disappear on December 31. In this episode, Tyler Emrick, CFA®, CFP®, and Walter discuss five important year-end tax planning considerations for 2026, including how recent tax law changes could affect your retirement. You'll learn: How the new senior tax deduction could influence Roth conversion decisions and retirement income planning Whether changes to the standard deduction, SALT limits, and itemized deductions create new opportunities How charitable giving strategies, including qualified charitable distributions, could reduce your tax bill Which retirement account distributions, Roth conversions, and investment decisions need attention before December 31 Why planning for next year's taxes, Medicare premiums, and future retirement income matters just as much as minimizing this year's tax bill 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 22, 2026Episode 23324 min

Mortgages in Retirement: How to Buy, Borrow, and Pay Off Your Home

Can you qualify for a mortgage after retirement? Should you pay cash for your next home, borrow against your investments, or take out a traditional mortgage? And with mortgage rates elevated, how should retirees think about paying down debt? Whether you're downsizing, purchasing a second home, or helping your children buy their first house, financing decisions can have a significant impact on your retirement plan. In this episode, Tyler Emrick, CFA®, CFP®, explores three common mortgage situations retirees face and the financial planning decisions behind them. In this episode, Tyler covers: How retirees can purchase a new home before selling their current one. Why qualifying for a mortgage without a paycheck may be easier than you think. How home equity lines of credit and securities-backed loans can provide temporary financing. Why your retirement plan should determine how much mortgage debt you take on and how aggressively you pay it off. How to compare 15-year, 30-year, and adjustable-rate mortgages based on your expected payoff timeline. When mortgage recasting or paying points might make sense. How taxes and investment withdrawals can influence your mortgage payoff strategy. How to help adult children buy a home without jeopardizing your own 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

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