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

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 Meetings, and the ongoing planning conversations that happen throughout the year as life changes.
We also discuss why coordinated planning matters so much as retirement decisions become more interconnected — from Roth conversions and tax planning to Medicare, Social Security, estate planning, spending goals, and retirement income strategies.
In this episode:
What proactive financial planning actually means
Why preparation matters in advisor meetings
The difference between investment management and true financial planning
How we help families navigate retirement transitions and major life decisions
Roth conversion mistakes and tax planning coordination
Why written recommendations and ongoing advice matter
How taxes, investments, healthcare, and estate planning all work together
As retirement approaches, small financial decisions can have larger long-term consequences. The goal of proactive planning is helping families make informed decisions before those mistakes become expensive later.
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

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 discuss:
How to understand your true household allocation and risk exposure
Why many retirees naturally drift into an “all cash, all stocks” portfolio
Asset location and using different accounts efficiently
Required portfolio return and bear market testing
Dynamic spending throughout retirement
How strong markets can impact spending and gifting decisions
Roth conversions, IRA distributions, capital gains, and tax planning
Why retirement income planning is much bigger than simply withdrawing money from accounts
As retirement gets closer, every financial decision starts affecting the next one. The goal of a financial plan should not simply be to exist — it should help families make better decisions over time.
 
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

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 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

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

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

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 (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 (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

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

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