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

What a First Meeting with a Financial Advisor Should Look Like

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, 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

5 Worst Money Moves to Avoid Before Retirement

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 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

Your Tax Return Is a Blueprint — Here's How to Use It for Better Planning

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 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

Backdoor Roth IRA Explained: How High Earners Avoid Income Limits

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 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

Trump Accounts Explained: $1,000 Free for Your Kids.... But Is There a Catch?

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 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

Inherited IRA 10-Year Rule: Don’t Make This Costly Mistake

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 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

Social Security Strategies for Couples: Timing Decisions Worth $100,000+

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 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

How to Diversify Concentrated Stock Without a Big Tax Bill

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 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

The Retirement Spending Myth: Why the 80% Rule Gets It Wrong

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.
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

Why Most People Are Wasting Their HSA (And How to Fix It)

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 Medicare costs in retirement.
Tyler Emrick, CFA®, CFP®, breaks down how to turn your HSA from a simple medical spending account into a long-term, tax-efficient retirement asset.
In this video, you’ll learn:
HSA eligibility rules, 2026 contribution limits, catch-up contributions, and the December “last-month rule”
How High Deductible Health Plans qualify you to contribute
Why leaving your HSA in cash limits long-term growth
How to invest your HSA using brokerage options
The “invest now, reimburse later” strategy to build tax-free retirement liquidity
How HSAs can cover Medicare premiums, COBRA coverage, long-term care premiums, and other retirement healthcare costs
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