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

Not all Roth dollars are created equal—especially during times of market volatility. In this episode, Tyler Emrick, CFA®, CFP®, unpacks when Roth contributions, conversions, or pretax savings make the most sense, and how recent market declines may present timely Roth conversion opportunities. You'll learn how to be strategic with what assets you convert, when conversions might come with risks, and how tools like the mega backdoor Roth can help high earners build tax-free wealth. Whether you're retiring early or just looking for more tax-efficient growth, this episode offers practical guidance for getting Roth right. Here’s some of what we discuss in this episode: 🔄 Roth IRA vs. Roth 401(k) vs. Mega Backdoor Roth 📉 How market drops create conversion opportunities 💡 Using Roths strategically before Medicare or RMD age 🧾 Why tax bracket awareness is essential 🧠 Advanced strategies like asset location and timing Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

Markets have been shaken by a sharp selloff, with the S&P 500 down around 15% and the Nasdaq nearly 20% year-to-date. Much of the recent volatility is being driven by escalating trade tensions and a new round of tariffs that took effect on April 9. In this episode, Kevin Kroskey, CFP®, and Tyler Emrick, CFA®, CFP®, unpack what’s driving the recent market moves — from global supply chain disruptions to shifting investor sentiment and international dynamics. Here’s some of what we discuss in this episode: 📉 Why the market hates uncertainty—and how that’s showing up now ⚖️ Risk vs. uncertainty: what’s the difference and why it matters 🔁 How “Runway” helps retirees avoid emotional investment decisions 🧰 Strategies we’re using: rebalancing, dry powder, diversification 🧠 What to do (and not do) when tempted to time the market Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

If the recent market drop has you feeling uneasy, you’re not alone — but sharp swings are regularities you need to navigate. The S&P 500 and Nasdaq have both taken hits this year, but history shows that intra-year declines like these are common and something long-term investors have weathered time and again. In this episode, Tyler Emrick, CFA®, CFP®, breaks down recent market moves, highlights where diversification is working, and shares how tax strategies and disciplined rebalancing can help keep your investment strategy running smoothing and financial plan on track. Here’s some of what we discuss in this episode: 📉 Market pullbacks are normal—even healthy 📊 Diversification is your protection in volatile times 🔁 Rebalancing can improve long-term returns 💸 Tax-loss harvesting can create future tax benefits 🧠 Discipline beats emotion when markets get rocky Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

Big tax changes could be coming soon! On February 25, the House passed a budget resolution setting a $4.5 trillion cap for a new tax bill that could replace the Tax Cuts and Jobs Act (TCJA) before it expires at the end of 2025. But what will the new law look like, and how will it impact your financial plan? In this episode, Tyler Emrick, CFA®, CFP®, breaks down the key debates in Congress, what changes might be coming, and how you can prepare now to optimize your tax strategy. Here’s some of what we discuss in this episode: 📉 TCJA Expiration in 2026 – What happens when the current tax cuts expire? ⚖️ New Tax Bill Proposals – The biggest changes lawmakers are considering 💰 How to Prepare – What you should do now before changes take effect ⏳ Why Timing Matters – Waiting too long could cost you thousands 📊 Tax Planning for Retirement – Strategies to minimize your tax burden Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

Are you leaving money on the table? For families weighing their options when choosing a financial advisor, Vanguard’s Advisor Alpha study has long been the go-to guide—and now, fresh research from SmartAsset echoes the sentiment that the right advisor could boost your net returns by over 2% annually. In this episode, Tyler Emrick, CFA®, CFP®, reveals why many advisors miss that extra edge and how True Wealth Design’s holistic approach—integrating smart investments, proactive tax strategies, and comprehensive financial planning—ensures you capture every opportunity. Here’s some of what we discuss in this episode: Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

Retirement isn’t just about your savings—it’s also about where you choose to live. In this episode, Tyler Emrick, CFA®, CFP®, explores WalletHub’s 46-factor framework for ranking states for retirees, examining everything from tax rates and cost of living to leisure opportunities and healthcare access. We also unpack the key financial and personal considerations, such as state taxes on Social Security and the importance of staying close to loved ones. Tune in for practical insights to help you pick the retirement destination that fits your lifestyle and financial goals. Here’s some of what we discuss in this episode: Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

Can money really buy a longer, healthier life? In this episode, Tyler Emrick, CFA®, CFP®, dives into the surprising connection between wealth and longevity, uncovering how financial freedom can unlock better health, reduced stress, and more fulfilling retirement years. We also tackle the challenges of cognitive decline, exploring its impact on financial decision-making and how a trusted financial advisor can help safeguard your investments and create a solid aging plan to spend smarter, plan better, and protect your legacy as you age. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

The Social Security Fairness Act is shaking up the retirement landscape, eliminating the Windfall Elimination Provision (WEP) and Government Pension Offset (GPO) for millions of retirees. These long-standing provisions have impacted Social Security benefits for public sector workers like teachers, firefighters, and police officers—until now. In this episode, hear Tyler Emrick, CFA®, CFP® dive into what the changes mean, how retirees can expect retroactive payments, and the broader impact on the Social Security system. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

In this episode, Tyler Emrick, CFA®, CFP®, explores the key financial and psychological factors driving early Social Security claims. Discover how a well-optimized strategy could boost your lifetime spending by more than 10%. Your Social Security decision isn’t just about dollars and cents—it’s a critical piece of your retirement puzzle. Join us to learn how to sidestep common pitfalls, maximize your benefits, and secure a more confident, fulfilling retirement. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

Remember in 2022 when both stocks and bonds fell in lockstep? Did you think diversification failed? Want to build a more diversified, resilient portfolio to better grow and protect your hard-earned dollars? Hear Kevin Kroskey, CFP®, MBA discuss how the TALS strategy adds unique sources of returns to your portfolio outside of traditional stocks and bonds. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

Have a sizable brokerage account? Have unrealized capital gains? Pay income taxes at the highest rates? Want to pay your fair share but no more? If so, this is an episode not to miss. In part 1 of this series, Kevin Kroskey, CFP®, MBA explored why adding the TALS strategy may yield significant investing and tax benefits. He described how TALS can help you defer, avoid, and potentially eliminate your capital gains. For the most successful investors that meet the definition of an SEC Qualified Purchaser, generally one with $5m+ of investments, there is another leg to the TALS strategy that can help you solve your ordinary income tax problems too. Whether derived through your business or from non-business income such as wages, interest, non-qualified dividends be sure to tune in and listen closely. Here’s some of what we discuss in this episode: Learn more about tax strategies and tax-aware investing here: https://www.truewealthdesign.com/part-2-the-long-and-short-on-tax-aware-long-short-tals-investing/ Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

For successful investors and high-income earners, this is an episode not to miss... Sure, you can own an S&P 500 ETF or mutual fund. You could also own the 500 stocks individually, a strategy nowadays called direct indexing. Direct indexing aims to capitalize on individual stock volatility and add tax benefits by harvesting losses. Or you may choose to go a step farther up the complexity ladder to own the 500 stocks individually with a tax-aware, long-short overlay. Let's call that TALS for short. Here you expect to obtain the return of the S&P 500, add an extra return from the overlay, increase diversification, and provide significantly more tax benefits than direct indexing. It's a mouthful, but it sure sounds good! Have a sizable brokerage account? Have unrealized capital gains? Be sure to listen to Kevin Kroskey, CFP®, MBA explore why adding the TALS strategy can help solve these good problems to have. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth Tax-Loss Harvesting: Wall Street’s New Strategy Cuts Rich Americans' Bills – Bloomberg - https://www.bloomberg.com/news/features/2024-10-24/tax-loss-harvesting-wall-street-s-new-strategy-cuts-rich-americans-bills Watch Wall Street Finds Another Workaround With Taxes, Losses – Bloomberg - https://www.bloomberg.com/news/videos/2024-10-25/wall-street-finds-another-workaround-with-taxes-losses-video

Is diversification dead? Over the last decade, putting all your eggs in the S&P 500 basket has outperformed diversified strategies. In this episode, hear Tyler Emrick, CFA®, CFP®, explore why the U.S. market has been on an unprecedented run, why the global market portfolio hasn't kept up, and whether diversification is really the best move for long-term investors. We dive into the rise of ETFs, global market trends, and why the "SPY or die" mentality might not hold up in the future. Learn why diversification should still be a priority despite the recent performance gap. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

The clock is ticking on the 2017 Tax Cuts, and big changes are looming. In this episode, Tyler Emrick, CFA®, CFP®, breaks down the complexities of the 2017 Tax Cuts and Jobs Act and its upcoming expiration in 2025. We dive into the original intent behind these cuts, what changes were made, and the impact on your bottom line. Learn how the expiration could lead to a significant tax hike unless new legislation is passed. We highlight key strategies—like maximizing retirement accounts under lower rates and leveraging deductions—so you can prepare for the changes on the horizon. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

This episode explores the disconnect between retirement expectations and reality, referencing a recent Gallup report that shows most retirees live comfortably despite fears about running out of money. Hear Tyler Emrick, CFA®, CFP®, discuss why non-retirees may be more fearful than needed, the role of Social Security, and how age-based spending patterns contribute to the relative success of sustaining a retirement lifestyle. And be sure to pay attention to how working with the right financial advisor can help you achieve financial independence earlier (data suggests up to three years earlier) by measuring and modeling your current spending and retirement goals more appropriately. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth Check out the Social Security episode referenced in this show: https://www.truewealthdesign.com/social-security-timing-reframing-your-thinking-for-better-decision-making/

Over the last few years, significant changes have been made to how retirement accounts are managed after death, especially with new RMD rules. In July, the IRS issued its new Final Regulations regarding the SECURE Act’s provisions. In this episode, hear Tyler Emrick, CFA®, CFP®, break down the key provisions, including the 10-Year Rule for beneficiaries and updates to RMD timelines, and how these changes impact your retirement and estate planning. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

In this episode, Tyler Emrick, CFA®, CFP®, reviews the rich insights from Fritz Gilbert's blog post, "Six Lessons From Six Years of Retirement." Exploring the complexities of retirement that go beyond financial concerns, highlighting how true fulfillment often lies in navigating the non-financial aspects of this life stage. Join us as we unravel the lessons that can guide you to a more satisfying retirement. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

There is no such thing as a free lunch – or is there? Discover the world of buffered ETFs, a fast-growing segment in financial markets designed to offer investors defined outcomes with built-in downside protection. In this episode, hear Tyler Emrick, CFA®, CFP®, dive into the mechanics, benefits, and potential drawbacks of these complex financial instruments. And be sure to listen to the comparisons of buffered ETFs against traditional investment options and how each may fit (or not) in your diversified investment strategy. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

In this episode, hear Tyler Emrick, CFA®, CFP®, discuss why meticulous budgeting isn’t necessary for most people approaching retirement. Discover how understanding your lifestyle spending and anticipating future changes can lead to more effective financial planning. Learn about the "Retirement Spending Smile" concept and why focusing on your lifestyle expenses is more beneficial than a line-by-line budget. Plus, we’ll explore how your financial advisor should be helping you monitor spending against your goals. Here’s some of what we discuss in this episode: Check out our interview with retirement researcher Dr. David Blanchett: Part 1 - https://www.truewealthdesign.com/ep-101-interview-with-retirement-researcher-dr-david-blanchett-part-1/ Part 2 - https://www.truewealthdesign.com/ep-102-interview-with-retirement-researcher-dr-david-blanchett-part-2/ Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth

It's almost Election Day in the US, and opinions are flying. But should elections sway your long-term investment strategy? Find out in this episode as Tyler Emrick, CFA®, CFP®, cuts through the political noise exploring historical market performance in past election years and Presidential terms. Sharing how you can use this data to set your emotions aside and make more informed investment decisions. Here’s some of what we discuss in this episode: Have questions? Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals. http://bit.ly/calltruewealth