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

Deferred Compensation in 2025: What’s Changed, What to Watch For & New Planning Opportunities

Get your customized planning started by scheduling a no-cost discovery call: http://bit.ly/calltruewealth
Deferred compensation plans can be a powerful retirement tool — but they’re often misunderstood and carry unique risks. In this episode, Tyler Emrick, CFA®, CFP®, breaks down how these plans work in 2025, from 409A rules to 457(b) and 457(f) plans that are especially common in the healthcare industry. We’ll cover why so many executives and physicians use them, how payout rules can trigger unexpected tax bills, and what happens when your employer is acquired — including timely insights for those in Northeast Ohio as Summa Health transitions from nonprofit to for‑profit under a private equity firm.
Here’s some of what we discuss in this episode:
🧾 Know the fine print – Rules on payout timing are strict and often irreversible.
⚠️ Watch for triggers – Job changes or company buyouts can force unexpected distributions.
📉 Subject to credit risk – If your employer fails, you could lose your deferred comp.
📊 Plan your income – Coordinate payouts with your tax strategy to reduce the hit.
💡 Advanced tools – Strategies like TALS can help offset large taxable events.
 
Part 1: The Long and Short on Tax-Aware, Long-Short (TALS) Investing - https://www.truewealthdesign.com/podcasts/part-1-the-long-and-short-on-tax-aware-long-short-tals-investing/
 
Part 2: The Long and Short on Tax-Aware, Long-Short (TALS) Investing - https://www.truewealthdesign.com/podcasts/part-2-the-long-and-short-on-tax-aware-long-short-tals-investing/
 
Part 3: The Long and Short on Tax-Aware, Long-Short (TALS) Investing - https://www.truewealthdesign.com/podcasts/part-3-the-long-and-short-on-tax-aware-long-short-tals-investing/
 
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 Big Beautiful Bill Act Could Change Your Retirement Plan — Here’s How

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Congress passed the One Big Beautiful Bill Act — the biggest tax overhaul since the 2017 Tax Cuts and Jobs Act — and it could change the way you plan for retirement. From a brand‑new $6,000 senior deduction to new rules for charitable giving and major shifts in healthcare subsidies before Medicare, the law creates both new opportunities and new pitfalls for retirees and pre‑retirees.
In this episode, Tyler Emrick, CFA®, CFP®, unpacks what the changes really mean for you. We’ll explore how to take advantage of the charitable giving rules before new floors kick in, how to manage Roth conversions to maximize the senior deduction, and what to watch for as ACA subsidies become less generous starting in 2026. Whether you’re five years from retirement or already living it, this episode will help you understand the risks, the opportunities, and how to keep your plan on track under the new law.
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
Here’s some of what we discuss in this episode:
💸 Above-the-line charitable deduction coming in 2026
📦 SALT cap expanded = more families itemizing again
📉 New ACA subsidy cliff could cost early retirees $10K+
🔁 Roth conversions just got trickier, but they’re still powerful
Our website:  https://www.truewealthdesign.com/ 
Phone: 855.TWD.PLAN
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

Over 800 Pages of Taxes: Don’t Worry, We Read It So You Don’t Have To

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The One Big Beautiful Bill Act is over 800 pages long and packed with tax changes that impact retirees, individuals, and small business owners. From expanded standard deductions and new senior tax breaks to permanent small business deductions and the end of many green energy credits, this bill reshapes key parts of the tax code — at least for the next few years.
In this episode, Tyler Emrick, CFA®, CFP®, breaks down what’s actually in the bill and what it means for your planning. You’ll learn:
How the standard deduction and senior deduction are changing (and why it matters for Social Security taxation)
The permanent extension of reduced tax rates from the 2017 tax law
New above-the-line deductions for tips, overtime, and car loan interest
Changes to SALT deductions and charitable contributions
What small business owners need to know about the permanent QBI deduction and phaseouts
Whether you’re already retired or planning ahead for your business and family, this episode will help you understand the real implications — without having to read 800 pages of tax law yourself.
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
 
Watch the show now on YouTube: https://www.youtube.com/channel/UCjENBHOti-IEJFqeydZm_Fg?sub_confirmation=1

Cybersecurity and Your Retirement: Protecting What You’ve Built

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Retirees are increasingly targeted by cybercriminals — and the scams are getting more sophisticated. From fake emails and stolen phones to account takeovers and SIM card fraud, even cautious investors can be at risk.
In this episode, Tyler Emrick, CFA®, CFP®, shares a real story of an attempted security breach involving a True Wealth Design client — and what made the firm catch it before damage was done. You’ll learn the most common cybersecurity threats facing retirees, how to secure your financial accounts, and what to do if you think you’ve been scammed.
Plus, we cover smart strategies like using a password manager, enabling two-factor authentication, freezing your credit, and why every retiree should have a Trusted Contact on file.
If you’ve worked hard to build a secure retirement, this episode will help you protect it.
Here’s some of what we discuss in this episode:
🔐 $3.4 billion lost to scams in 2023—just from retirees📞 How a client’s phone was hijacked and nearly cost them big🎣 Phishing, fake tech support, romance scams & more🔁 Best practices: strong passwords, 2FA, credit freezes, and identity monitoring🛡️ New safety features: trusted contacts and “safe words” for financial 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

Costly Retirement Mistakes To Avoid Before It’s Too Late

Some retirement mistakes are obvious. Others are silent — slowly eroding your plan year after year without setting off alarms. From investing the same old way to ignoring tax planning and claiming Social Security without a strategy, these missteps can cost you more than you think.
In this episode, Tyler Emrick, CFA®, CFP®, walks through five of the most common — and avoidable — financial mistakes people make in and near retirement. You’ll walk away with practical strategies to strengthen your plan, avoid missteps, and make more confident decisions as you approach — and live in — retirement.
Whether you're five years from retirement or already in it, this episode will help you spot hidden risks and take smarter action today.
Here’s some of what we discuss in this episode:
📉 Mistake #1: Investing the same way you always have💰 Mistake #2: Taking too much risk trying to “catch up”📊 Mistake #3: Not measuring progress against your plan🧾 Mistake #4: Ignoring tax planning opportunities🕰️ Mistake #5: Claiming Social Security without a clear strategy
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth
 
Check out our other no-cost financial resources here: https://www.truewealthdesign.com/financial-resources/
 
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Warren Buffett’s Final Chapter: Purposeful Wealth and Practical Planning

Warren Buffett announced his retirement as CEO of Berkshire Hathaway at the company’s 2025 annual meeting — marking the end of one of the most legendary investing careers in history. But his lessons aren’t just for billionaires or portfolio managers. They’re surprisingly relevant for anyone approaching retirement or looking to live more intentionally with their wealth.
 
In this episode, Tyler Emrick, CFA®, CFP®, explores the timeless wisdom behind Buffett’s philosophy—from staying invested through downturns to making confident decisions when fear is high. We also discuss how a strong financial plan helps you make purposeful choices: knowing when to spend, when to give, and how to align your wealth with the life you want to live—now and in the future.
 
Here’s some of what we discuss in this episode:
📈 What 90% of Buffett’s wealth after 65 teaches us about patience
🧠 "Be greedy when others are fearful" — and how to actually do it
📉 What to do when market fear clouds good decision-making
🌱 Giving while living — and planning to do it with confidence
🔧 Why your financial plan is your most powerful tool
 
Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth

One Year from Retirement: A Critical Window for Planning and Perspective

When you're 12 months away from retirement, everything starts to feel real. From hard deadlines like pension elections and Medicare sign-ups to emotional shifts around identity and purpose, this final year before retirement can feel like a perfect storm.
 
In this episode, Tyler Emrick, CFA®, CFP®, explores the unique challenges clients face in this transition — and how the financial planning process needs to evolve accordingly. You'll hear how True Wealth Design helps clients navigate not just the dollars and cents, but also their lifestyle risk, time horizons, and the often-overlooked emotional aspects of leaving a long career behind.
 
Here’s some of what we discuss in this episode:
📆 Why the last 12 months before retirement matter so much.💸 The truth about lumpy spending and how to plan around it.💑 Pension decisions, Social Security timing, and survivor benefits.🧠 How to navigate identity shifts and relationship changes.📊 Why advisors should be more than number crunchers.
 
Resources
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/
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Should You Roth? Making the Right Call at the Right Time

Not all Roth dollars are created equal—especially during times of market volatility.
In this episode, Tyler Emrick, CFA®, CFP®, unpacks when Roth contributions, conversions, or pretax savings make the most sense, and how recent market declines may present timely Roth conversion opportunities.
You'll learn how to be strategic with what assets you convert, when conversions might come with risks, and how tools like the mega backdoor Roth can help high earners build tax-free wealth. Whether you're retiring early or just looking for more tax-efficient growth, this episode offers practical guidance for getting Roth right.
Here’s some of what we discuss in this episode:
🔄 Roth IRA vs. Roth 401(k) vs. Mega Backdoor Roth
📉 How market drops create conversion opportunities
💡 Using Roths strategically before Medicare or RMD age
🧾 Why tax bracket awareness is essential
🧠 Advanced strategies like asset location and timing
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth

Tariffs, Turbulence, and How To Stay On Track

Markets have been shaken by a sharp selloff, with the S&P 500 down around 15% and the Nasdaq nearly 20% year-to-date. Much of the recent volatility is being driven by escalating trade tensions and a new round of tariffs that took effect on April 9.
In this episode, Kevin Kroskey, CFP®, and Tyler Emrick, CFA®, CFP®, unpack what’s driving the recent market moves — from global supply chain disruptions to shifting investor sentiment and international dynamics.
Here’s some of what we discuss in this episode:
📉 Why the market hates uncertainty—and how that’s showing up now
⚖️ Risk vs. uncertainty: what’s the difference and why it matters
🔁 How “Runway” helps retirees avoid emotional investment decisions
🧰 Strategies we’re using: rebalancing, dry powder, diversification
🧠 What to do (and not do) when tempted to time the market
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals.
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Don’t Panic: Navigating Market Downturns and Boosting After-Tax Returns

If the recent market drop has you feeling uneasy, you’re not alone — but sharp swings are regularities you need to navigate. The S&P 500 and Nasdaq have both taken hits this year, but history shows that intra-year declines like these are common and something long-term investors have weathered time and again.
In this episode, Tyler Emrick, CFA®, CFP®, breaks down recent market moves, highlights where diversification is working, and shares how tax strategies and disciplined rebalancing can help keep your investment strategy running smoothing and financial plan on track.
Here’s some of what we discuss in this episode:
📉 Market pullbacks are normal—even healthy
📊 Diversification is your protection in volatile times
🔁 Rebalancing can improve long-term returns
💸 Tax-loss harvesting can create future tax benefits
🧠 Discipline beats emotion when markets get rocky
 
Have questions?
Need help making sure your investments and retirement plan are on track? Click to schedule a free 15-minute call with one of True Wealth's CFP® Professionals.
http://bit.ly/calltruewealth