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Retirement Planning Masterclass

The 7 Retirement Risks Most People Never See Coming

How to Protect Your Income, Reduce Your Taxes, and Retire with Confidence

Social Security OptimizationTax StrategySequence RiskIRMAARoth ConversionsIncome Planning

Presented by JP Alexander, CEO & Wealth Manager · Greystone Wealth Management · Huntington Beach, CA

Fiduciary · Independent RIA · Registered Investment Advisor

About Your Host

You deserve a retirement advisor who sees the whole picture.

I'm JP Alexander, CEO and Lead Advisor at Greystone Wealth Management — an independent, fiduciary wealth management firm based in Huntington Beach, California.

We specialize in helping pre-retirees and retirees create clarity, confidence, and structure around retirement — covering income planning, tax strategy, Social Security optimization, investment management, and estate coordination.

Independent RIAFiduciary AdvisorRetirement SpecialistHuntington Beach, CA

What We Help You With

💰

Retirement Income Planning

Creating reliable, sustainable income you can't outlive

📋

Tax Strategy

Reducing what you pay in taxes — now and in retirement

🏛️

Social Security Optimization

Maximizing your lifetime benefit with smart timing

📈

Investment Management

Portfolios designed for retirement, not just accumulation

🏡

Estate Planning Coordination

Protecting your legacy and simplifying the transfer of wealth

Today's Webinar

What We'll Cover Today

Eight critical retirement planning topics — explained simply, visually, and practically.

Social Security Optimization

When to claim, how to maximize, and what most people get wrong

The Provisional Income Trap

How your retirement income can make Social Security taxable

IRMAA & Medicare Surprises

The hidden income thresholds that spike your Medicare premiums

Sequence-of-Returns Risk

Why the order of market returns matters more than the average

Withdrawal Rate Risk

How much you can safely take — and what happens when you take too much

Tax Rate Risk

Why your future tax rate may be higher than you think

Roth Conversion Strategy

How to move money into tax-free growth before it's too late

The Fiscal House Framework

Organizing your retirement into Foundation, Walls, and Roof

"The goal isn't maximum information — it's maximum clarity."

The Retirement Landscape

Retirement Is Not Just About Investment Returns

Most people focus on growing their money. But in retirement, the risks that matter most are often invisible — until it's too late.

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Sequence Risk

Early market losses + withdrawals = permanent damage

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Withdrawal Rate Risk

Taking too much, too fast depletes portfolios faster than expected

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Tax Rate Risk

Future tax rates may be higher — especially with RMDs

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Social Security Taxation

Up to 85% of benefits can become taxable income

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IRMAA Surcharges

One income spike can cost thousands in Medicare premiums

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Widow Tax Trap

Losing a spouse can dramatically increase your tax burden

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Longevity Risk

Outliving your money is the risk most people underestimate

The good news?

Every one of these risks can be planned for — with the right strategy.

Section 01

Social Security: The Most Important Decision You'll Make

Most people make this decision based on emotion, not strategy. The difference can be worth hundreds of thousands of dollars.

64%

of retirees claim before Full Retirement Age

$182,000+

potential lifetime benefit difference between age 62 vs 70

85%

of Social Security can be taxable income

guaranteed increase per year you delay past FRA

"Social Security isn't just a check — it's the foundation of your retirement income strategy."

Claiming Strategy

When You Claim Changes Everything

Claiming at 62 vs. 70 can mean a 54% difference in your monthly benefit — for the rest of your life.

Age 62 — Early

70%

Permanent 30% reduction

Age 67 — FRA

100%

Full retirement benefit

Age 70 — Maximum

124%

+8% per year past FRA

Section 02 — The Hidden Tax

The Provisional Income Trap

Most retirees don't realize that their other income sources can make their Social Security benefit taxable.

Provisional Income Formula

Adjusted Gross Income

Your IRA distributions, pension, wages, etc.

+ Tax-Exempt Interest

Municipal bond interest (yes, it counts)

+ 50% of Social Security

Half of your SS benefit always counts

= Provisional Income

This determines how much SS is taxed

Married Filing Jointly Thresholds

Below $32,000 → 0% of SS taxable

$32,000 – $44,000 → up to 50% taxable

Above $44,000 → up to 85% taxable

Interactive Example

Adjust other income to see how it affects SS taxation:

Other Retirement Income$50,000/yr

$0$100,000

Other Income$50,000

+ 50% of SS ($36k)$18,000

= Provisional Income$68,000

85% of SS is Taxable

~$30,600 of your SS benefit is added to taxable income

Section 03 — Medicare Surprise

IRMAA 2026: The Medicare Income Surcharge Most People Never See Coming

One income event — a Roth conversion, a home sale, an RMD — can trigger thousands in extra Medicare premiums.

2024 MAGI (2-yr lookback → 2026 premium)	Monthly Premium	IRMAA Surcharge	Extra Annual Cost
≤ $109,000 (Single) / ≤ $218,000 (MFJ)	$202.90	None	$0
$109,001–$137,000 / $218,001–$274,000	$284.10	+$81.20	+$974/yr
$137,001–$171,000 / $274,001–$342,000	$405.80	+$202.90	+$2,435/yr
$171,001–$205,000 / $342,001–$410,000	$527.50	+$324.60	+$3,895/yr
$205,001–$499,999 / $410,001–$749,999	$649.20	+$446.30	+$5,356/yr
≥ $500,000 (Single) / ≥ $750,000 (MFJ)	$689.90	+$487.00	+$5,844/yr

⚠️

The IRMAA Look-Back Rule (2026)

Medicare uses your income from 2 years ago to set your 2026 premiums. The 2026 standard Part B premium is $202.90/month. A one-time income event today can trigger surcharges for the next 2 years — even if your income drops back down. Proactive income planning can help you avoid or appeal these surcharges.

Section 04 — The Hidden Retirement Destroyer

Sequence-of-Returns Risk

"It's not just about the average return — it's about the order in which returns occur."

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Same Average Return

All three retirees earned approximately the same average annual return over 20 years

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Same Withdrawals

All three withdrew $50,000 per year from a $1,000,000 starting portfolio

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Different Outcomes

One thrived. One survived. One ran out of money — because of when the losses happened.

Here's the problem: When you're withdrawing money from your portfolio in retirement, a market downturn in the early years forces you to sell shares at low prices — permanently reducing the number of shares that can recover when the market bounces back. This is called sequence-of-returns risk, and it can permanently damage your retirement sustainability — even if your average return looks fine on paper.

Visual Demonstration

Three Retirees. Same Returns. Dramatically Different Outcomes.

Starting balance: $1,000,000 · Annual withdrawal: $50,000 · Average return: ~5%

Robert

Strong Early Returns

$1.0M

100% of original

Sandra

Mixed / Neutral Sequence

$1.0M

100% of original

Michael

Poor Early Returns

$1.0M

100% of original

Robert (Strong Early Returns)
Sandra (Mixed / Neutral Sequence)
Michael (Poor Early Returns)

The Solution

Protecting Your Foundation From Early Losses

The key is to avoid selling growth assets during a market downturn. That requires having a protected income layer that doesn't depend on the market.

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Income Buffer Strategy

Keep 1–2 years of living expenses in cash or short-term reserves. This allows your portfolio to recover without forced selling during downturns.

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Protected Income Layer

Create guaranteed income (Social Security, pension, annuity) that covers essential expenses — so you never have to sell investments at the worst time.

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The Fiscal House Foundation

Separate your 'Foundation' money (protected, guaranteed) from your 'Roof' money (growth). The Foundation absorbs the shock so the Roof can grow.

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Flexible Withdrawal Strategy

Have a plan to reduce withdrawals during major downturns. Even a 10–15% temporary reduction can dramatically extend portfolio longevity.

"The goal isn't to avoid market risk entirely — it's to make sure a bad year in the market doesn't become a bad decade in your retirement."

Section 05 — Withdrawal Risk

Withdrawal Rate Risk: How Much Is Too Much?

Starting with $1,000,000 — here's what happens over 30 years at different withdrawal rates.

✓ The "4% Rule" as a Starting Point

Research suggests 4% is a reasonable starting withdrawal rate for a 30-year retirement. But it's not a guarantee — it depends on your specific situation, tax strategy, and income sources.

⚠️ Market Volatility Makes It Worse

These projections assume steady returns. In reality, market volatility combined with high withdrawals creates compounding stress — especially in down years. This is why sequence risk and withdrawal rate risk work together.

Section 06 — The Tax Time Bomb

Tax Rate Risk: The Retirement Risk Nobody Talks About

Most retirees assume their taxes will be lower in retirement. For many, the opposite is true — especially once Required Minimum Distributions begin.

Why Your Tax Rate May Be Higher in Retirement

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Required Minimum Distributions (RMDs)

Under SECURE 2.0, RMDs begin at age 73. The IRS forces you to take distributions from your IRA — whether you need the money or not. Large IRAs can push you into higher brackets.

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Social Security Taxation

As your income grows, up to 85% of your Social Security benefit becomes taxable — stacking on top of your other income.

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The Widow Tax Trap

When one spouse dies, the survivor files as Single — facing higher rates on the same income with smaller standard deductions.

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Tax Cuts Expiring in 2026

The TCJA brackets were made permanent under the One Big Beautiful Bill (2025). However, Congress can always change tax law — and with $36T+ in national debt, future rate increases remain a real risk.

2026 Federal Tax Brackets (Married Filing Jointly)

⚠️ The RMD Problem

A $1M IRA at age 73 requires ~$36,500 in mandatory distributions. A $2M IRA requires ~$73,000. Combined with Social Security, pension, and other income — many retirees find themselves in the 22–24% bracket or higher.

✓ The Solution: Tax Diversification

Having money in taxable, tax-deferred, and tax-free (Roth) accounts gives you control over your tax rate in retirement. Roth conversions now can reduce your tax burden significantly later.

Section 06 — Tax Rate Risk

You Have $1,000,000 in Your IRA.

But how much of it is actually yours?

Select a tax rate scenario:

IRA Balance

$1,000,000

minus taxes at

22% Tax Rate

What you actually keep:

$780,000

The IRS gets: $220,000

The Planning Problem

Every dollar in a traditional IRA is pre-tax. You've never paid taxes on it. When you withdraw — or when the IRS forces you to at age 73 — every dollar is ordinary income. The question isn't just how much you have. It's how much you'll keep after taxes.

Section 06 — Tax Rate Risk

The History of U.S. Tax Rates

The top marginal rate has been as high as 94%. Today's 37% is historically low. With $36 trillion in national debt, the direction of future tax rates is an open question — and a real planning risk.

70%+ (Extreme)

50–69% (High)

37–49% (Elevated)

Under 37% (Low)

94%

Highest Rate Ever

1944–45, WWII era. Stayed above 70% for nearly 40 years.

70%

Post-War Era

Top rate from 1965–1981. Applied to the highest earners for nearly two decades.

50%

Reagan-Era Cut

ERTA 1981 dropped the top rate from 70% to 50% — a landmark tax reduction.

37%

Today's Top Rate

TCJA brackets made permanent under the One Big Beautiful Bill (2025). Historically low.

$36T+

National Debt

Future tax increases are a legitimate planning risk. The window to act is now.

"We are in one of the lowest tax environments in the last 80 years. The question is: are you taking advantage of it?"

Section 07 — The Roth Strategy

Roth Conversion: Paying Taxes Now to Save More Later

Strategic Roth conversions during the "tax window" — before RMDs begin — can dramatically reduce your lifetime tax burden.

❌ Traditional IRA Only

IRA Balance at 73$1,000,000

Required RMD (Year 1)$36,496

Total Taxable Income$85,000

Tax Bracket22%

Estimated Tax Bill$18,700

SS Benefit Taxable85%

The Problem

With all savings in a traditional IRA, every dollar you withdraw is taxed as ordinary income. Your RMDs are mandatory — you can't control the timing. And as your IRA grows, your RMDs grow with it, potentially pushing you into higher brackets every year.

Annual tax bill: ~$18,700

Over 20 years: ~$374,000 in taxes

Section 08 — The Framework

The Fiscal House Framework

Think of your retirement like a house. Every layer serves a different purpose — and a strong foundation protects everything above it.

The key insight: Sequence-of-returns risk and withdrawal rate risk are dramatically reduced when your Foundation is strong enough to cover essential expenses — because you never have to sell growth assets at the wrong time.

The Greystone Approach

The WISE Blueprint™

An integrated retirement process that coordinates all four dimensions of your financial life — so nothing falls through the cracks.

Wealth

Investment Strategy & Portfolio Design

Building and managing a portfolio designed for retirement income — not just accumulation. Asset allocation, risk management, and rebalancing.

Income

Income Distribution Planning

Creating a reliable, sustainable income stream you can't outlive. Coordinating Social Security, pensions, annuities, and portfolio withdrawals.

Strategy

Tax, Social Security & Distribution Strategy

Minimizing taxes over your lifetime through Roth conversions, bracket management, Social Security timing, and strategic distribution planning.

Estate

Legacy & Protection Planning

Ensuring your assets transfer efficiently to your heirs. Beneficiary designations, trusts, estate tax planning, and legacy coordination.

"Most advisors focus on one piece. We coordinate all four — because in retirement, everything is connected."

Real-World Examples

These Situations Are More Common Than You Think

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Case Study

The $14,000 Social Security Tax Surprise

Jim & Carol, Ages 67 & 65

The Situation

Retired with $1.2M in IRAs, $3,800/mo combined Social Security

What Went Wrong

Took IRA distributions without planning — pushed provisional income to $72,000

85% of Social Security became taxable. Paid $14,000 more in taxes than necessary.

What Could Have Helped

Roth conversions at 62–65 could have saved $8,000–$14,000 annually

"Every one of these situations was preventable — with the right planning in place."

Know Who You're Working With

Not All Financial Advisors Are the Same

Click any row to expand details

Role

Primary Focus

How They're Paid

Fiduciary?

Investment Manager

Portfolio management

AUM fee

✓ Yes

Insurance Agent

Protection products

Commissions

✗ No

Broker / Dealer Rep

Buying & selling investments

Commissions + fees

✗ No

Wealth Manager (Fiduciary RIA)

Greystone's Role

Complete financial picture

AUM fee (typically)

✓ Yes

"As a fiduciary, we are legally required to act in your best interest — not ours. That's not just a title. It's a legal obligation."

Your Next Step

Ready to See How This Applies to Your Retirement?

Schedule a complimentary Retirement Strategy Session with our team. We'll review your specific situation and show you exactly where the opportunities — and risks — are in your retirement plan.

🎯

Personalized Review

We review your specific income, tax, and Social Security situation

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Retirement Income Analysis

See a clear picture of your projected retirement income and gaps

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Action Plan

Leave with specific, actionable next steps — no obligation

📅 Schedule Your Strategy Session 📞 Call Our Office

Greystone Wealth Management · Huntington Beach, CA 92647

In-office or virtual via Zoom · Complimentary · No obligation

The information presented in this webinar is for educational purposes only and does not constitute financial, tax, or legal advice. All examples are hypothetical. Past performance is not indicative of future results. Greystone Wealth Management is a Registered Investment Advisor.