Podcast
Retire Smarter with Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP®
Hosted by Kevin Kroskey, CFP® & Tyler Emrick, CFA® CFP® · EN
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.
25episodes
Episodes
Newest firstAll episodes
Why Most Financial Plans Fail (And How To Build A Better One)
1w ago00:16:21Tap to summarizeMost 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
Transcribe →What a First Meeting with a Financial Advisor Should Look Like
2w ago00:19:43Tap to summarizeMost 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
Transcribe →5 Worst Money Moves to Avoid Before Retirement
3w ago00:22:39Tap to summarizeAs 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
Transcribe →Your Tax Return Is a Blueprint — Here's How to Use It for Better Planning
Apr 1600:22:46Tap to summarizeMost 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
Transcribe →Backdoor Roth IRA Explained: How High Earners Avoid Income Limits
Apr 900:22:29Tap to summarizeBackdoor 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
Transcribe →Trump Accounts Explained: $1,000 Free for Your Kids.... But Is There a Catch?
Apr 200:18:56Tap to summarizeTrump 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
Transcribe →Inherited IRA 10-Year Rule: Don’t Make This Costly Mistake
Mar 2600:19:41Tap to summarizeGet 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
Transcribe →Social Security Strategies for Couples: Timing Decisions Worth $100,000+
Mar 1900:20:22Tap to summarizeGet 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
Transcribe →How to Diversify Concentrated Stock Without a Big Tax Bill
Mar 1200:18:43Tap to summarizeA 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
Transcribe →The Retirement Spending Myth: Why the 80% Rule Gets It Wrong
Mar 500:20:56Tap to summarizeMost 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
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