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

Many people assume they have to wait until age 59½ before they can retire because that's when retirement accounts generally become available without the 10% early withdrawal penalty. But in reality, early retirement is often less about how much you've saved and more about how you access your money.
In this episode, Tyler Emrick, CFA, CFP® discusses the planning strategies that can help bridge the gap before traditional retirement account access, why saving across different account types creates flexibility, and how thoughtful income planning can make early retirement a realistic option.
We discuss:
Why age 59½ matters—and why it doesn't necessarily determine when you can retire
Planning opportunities including the Rule of 55, 72(t), and Net Unrealized Appreciation (NUA)
Why taxable brokerage accounts, Roth IRA contributions, and cash reserves can create flexibility
Building a retirement income bridge before Social Security, pensions, and Medicare begin
Healthcare planning before age 65, including COBRA and ACA Marketplace coverage
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/
 
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How much money is enough to retire?
It may be the most common retirement planning question, but it isn't always the right one.
In this episode, Tyler Emrick, CFA®, CFP®, explores why financial security is often more psychological than mathematical and why some retirees with millions of dollars still worry about running out of money.
Tyler discusses:
Why "enough" often keeps moving
Behavioral biases that affect retirement decisions
Why many retirees struggle to spend after decades of saving
The difference between financial independence and financial confidence
Practical ways to think differently about retirement
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/ 
Schedule your no-cost discovery call: http://bit.ly/calltruewealth 
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

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
Medicare and IRMAA considerations
How working affects retirement tax planning
Deciding whether working is financially and personally worthwhile
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

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 efficiency.
Tyler covers:
Why taxes often increase later in retirement
Roth conversion opportunities before RMDs
Capital gains harvesting strategies
Social Security timing considerations
Medicare IRMAA planning
The widow's tax trap
Why waiting too long can permanently reduce planning flexibility
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

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, including the 2032 trust fund projection, the 2034 combined trust fund projection, and why Social Security is not “going bankrupt.”
Tyler covers:
What the 2026 Social Security Trustees Report says
Why benefits do not disappear if the trust fund is depleted
Why the retirement trust fund projection moved to 2032
How much of scheduled benefits may still be payable
The most likely Social Security fixes Congress may consider
Whether Social Security claiming strategies should change
What affluent retirees should focus on instead
 
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.
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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®, covers:
What a donor-advised fund is and how it works
Why donor-advised fund assets have nearly doubled since 2020
How donating appreciated stock can reduce taxes and avoid capital gains
Why investment growth inside a donor-advised fund may increase charitable impact over time
How charitable bunching strategies can create larger tax deductions
Common donor-advised fund mistakes and misconceptions
Real-world situations where donor-advised funds may fit into a retirement or tax planning strategy
For retirees and investors who regularly support charities, a donor-advised fund can be much more than a charitable account. It can be a tax planning tool, an investment tool, and a way to simplify ongoing charitable giving.
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

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-efficient planning opportunity that may allow investors to exchange appreciated stocks and ETFs into a diversified ETF without first selling and realizing capital gains taxes.
Tyler covers:
What a 351 Exchange is and how it works
The difference between a 351 Exchange and a traditional exchange fund
Rules investors must satisfy before qualifying
Which assets qualify and which assets do not
ETF eligibility requirements
How highly appreciated ETF portfolios may be consolidated into a diversified ETF
How concentrated stock positions may fit into a 351 Exchange strategy
The potential benefits of reducing concentration risk without immediately triggering capital gains taxes
How 351 Exchanges compare to tax-aware long-short strategies and other tax-efficient diversification techniques
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/ 
Schedule your no-cost discovery call: http://bit.ly/calltruewealth 
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

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 conversion
Whether to spread conversions throughout the year
Tax bracket management and conversion timing
Why recharacterizations no longer being available matters
How to pay Roth conversion taxes efficiently
Roth conversions before age 59½
Estimated tax payments and withholding strategies
Which investments may be best suited for Roth accounts
Why higher-growth investments are often prioritized inside Roth IRAs
Coordinating Roth conversions with investment management and rebalancing
Tyler also explains why many Roth conversion mistakes have less to do with the conversion itself — and more to do with poor timing, tax management, and implementation decisions.
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/ 
Schedule your no-cost discovery call: http://bit.ly/calltruewealth 
 
Check out our other no-cost financial resources here: https://www.truewealthdesign.com/financial-resources/ 
 
Facebook: https://www.facebook.com/TrueWealthDesign/ 
LinkedIn: https://www.linkedin.com/company/true-wealth-design/ 
X: https://x.com/truewealthdesgn 
 
Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

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 of investing and why portfolio management involves much more than simply picking investments.
 
Topics covered include:
Why diversification still matters despite years of U.S. market dominance
Emerging markets outperformance and the importance of global exposure
How ETFs and asset location can improve after-tax returns
Asset location strategies across taxable and retirement accounts
Public REIT dislocations and investment vehicle structure considerations
Managing concentrated stock positions more tax efficiently
Donor-advised funds, QCDs, and gifting appreciated securities
Tax-aware long/short strategies and multi-year planning
The “architecture before allocation” philosophy at True Wealth Design
Tyler also explains how coordinated planning across investments, taxes, retirement income, estate strategy, and charitable giving can help improve long-term outcomes.
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/ 
Schedule your no-cost discovery call: http://bit.ly/calltruewealth 
 
Check out our other no-cost financial resources here: https://www.truewealthdesign.com/financial-resources/ 
 
Facebook: https://www.facebook.com/TrueWealthDesign/ 
LinkedIn: https://www.linkedin.com/company/true-wealth-design/ 
X: https://x.com/truewealthdesgn 
 
Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

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