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

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 income limits and contributio...

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, but the tax treatment is very diff...

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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, ...

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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 ...

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 learn:

• How a Section 351 exchange...

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Emrick, CFP®, CFA®, explains what the research shows about how retirement spending changes over time and why relying on outdated rules like the 80 percent rule can lead to over-saving and under-living or under-planning altogether.

Draw...

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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 Medicare costs in retirement.

Tyler Em...

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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 compounding tax consequences — especi...

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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 season for individuals and business ow...

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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 how to think about retirement cash...

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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 makes sense, and how to properly struc...

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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 retirees may be able to spend more under u...

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Most investors focus on returns. Smart investors focus on what they keep after taxes.

In this episode of Retire Smarter, we break down how two portfolios can earn the same return—and still produce dramatically different tax outcomes. This isn’t about predicting markets or chasing performance. It’s about making structural invest...

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In this episode of Retire Smarter, Tyler Emrick, CFA®, CFP®, walks through a practical Retirement Planning Checklist for 2026, focused on the financial moves that matter most in the first few weeks of the year. From front-loading 401(k) and HSA contributions to planning Roth conversions, setting up Qualified Charitable Distribu...

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Over the past month, we released a six-part video series breaking down how ultra-wealthy investors think about taxes, and more importantly, how they legally minimize them.

In this episode, we’ve stitched the entire Tax-Aware, Long-Short (TALS™) Strategy series together to allow you to hear the full framework in one place, and w...

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Roth IRAs and Roth 401(k)s are powerful tools — but most people use them without a clear strategy. In this episode, Tyler Emrick, CFA®, CFP®, breaks down how to think about Roth accounts before retirement, after retirement, and even how they impact your spouse and your legacy.

We’ll explore how to decide between pre-tax and Rot...

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Most retirees worry about whether their money will last—but few understand the real variables that determine success. In this episode, we go beyond the usual “spend less, earn more” advice and unpack the math that truly drives a sustainable retirement: the rate of return you actually need, how to stress-test your portfolio agai...

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For many retirees, healthcare costs before Medicare can be one of the biggest financial shocks — often exceeding $25,000 a year. But with the right planning, that same $25,000 can turn into a tax credit instead of an expense.

In this episode, Tyler Emrick, CFA®, CFP® dives into how the Affordable Care Act’s (ACA) Premium Tax Cr...

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In this episode of Retire Smarter, Tyler Emrick, CFA®, CFP®, breaks down how to gift smarter — whether your goal is to support family or give back to charity.

With the One Big Beautiful Bill Act (OBBBA) reshaping charitable deductions starting in 2026, now is the time to rethink your strategy. Tyler explains why cash may not be...