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

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 Medica...

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 ef...

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, includi...

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...

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-efficie...

So you’ve decided to do a Roth conversion… now what? Most Roth conversion conversations focus on whether you should do one. But the long-term value often comes from how the strategy is actually implemented. In this episode, Tyler Emrick, CFA®, CFP® walks through the overlooked decisions that can materially impact the outcome of a Roth conversion strategy. Topics include: When to complete a Roth co...

Investment management is often framed around picking stocks, predicting markets, and finding outperforming investments. But many of the decisions that have the biggest long-term impact on investor outcomes come from diversification, tax strategy, portfolio construction, and how investments are implemented over time.   In this episode, Tyler Emrick, CFA®, CFP®, discusses the often-overlooked side o...

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth This episode walks through what proactive financial planning actually looks like beyond investment management alone. Tyler Emrick, CFA, CFP® breaks down how ongoing advice should work for retirees and pre-retirees, including the structure of our Progress Meetings, Tax & Investment Review M...

Most financial plans get built once, put in a drawer, and rarely used again.   But real financial planning should actively help guide decisions throughout retirement.   In this episode, Tyler Emrick, CFA, CFP® walks through three practical ways your financial plan should actually be helping you right now: investment decisions, spending decisions, and income & distribution planning.   We discus...

Most 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 pr...

Most 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,...

As 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...

Most 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...

Backdoor 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...

Trump 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,...

Get 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...

Get 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 you...

A 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 lea...

Most 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...

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Health Savings Accounts (HSAs) may be the most powerful tax-free retirement planning tool available, yet most people use them completely wrong. If you’re enrolled in a High Deductible Health Plan (HDHP), your HSA could offer triple tax-free growth and a strategic way to fund healthcare and Med...

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Required Minimum Distributions (RMDs) are not just mandatory withdrawals — they are forced taxable income that can quietly reshape your retirement tax picture. Higher income from RMDs can trigger increased marginal tax rates, IRMAA surcharges, greater Social Security taxation, and long-term co...

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Tax filing season is here — and even though most tax planning happens before year-end, there are still important moves you can make before filing your 2025 return. In this video, Tyler Emrick, CFA®, CFP®, walks through last-minute tax planning moves that still matter during the 2026 filing sea...

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth How much cash should you really hold in retirement? Too little cash can create stress and force poor decisions during market downturns. Too much cash can quietly erode a well-built retirement plan through inflation, taxes, and lost growth. In this episode, Tyler Emrick, CFA®, CFP®, breaks down...

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth Many parents and grandparents want to help family financially, but gift tax rules are often misunderstood. In this episode, Tyler Emrick, CFA®, CFP®, breaks down the 2026 gift tax rules in plain English, including how much you can give without triggering tax, when gifting appreciated stock mak...

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth For decades, the 4% rule has been used as a simple guideline for retirement spending—but it was never meant to be a guarantee. In this episode, Tyler Emrick, CFA®, CFP®, will revisit the research behind the 4% rule and explore new findings from its creator, Bill Bengen, suggesting that retiree...