Tax Planning for Million-Dollar Earners in Miami: Strategies Generic CPAs Miss

Earning Over $1 Million Annually? Your Generic CPA Is Costing You a Fortune

Are you a high-earning Miami professional, business owner, or executive with income exceeding $1 million annually? Maybe you're writing checks to the IRS for $300,000, $400,000, or $500,000+ every year and wondering if there are legitimate strategies to reduce this burden? Or perhaps your current CPA prepares competent tax returns but never discusses sophisticated planning strategies because they don't work with enough high-net-worth clients to develop expertise in advanced tax minimization?

You've found exactly the resource you need, and I'm genuinely glad you're here.

I'm writing this comprehensive guide with one specific purpose: to meet you, introduce Whittmarsh Tax & Accounting, and earn the opportunity to show you how sophisticated tax planning for million-dollar earners can save you $50,000 to $200,000+ annually through strategies that generic CPAs either don't know about or don't have the expertise to implement properly.

We specialize in helping high-net-worth individuals in Miami, Aventura, and throughout South Florida who earn $1 million+ annually and need advanced tax planning that goes far beyond basic compliance—including charitable remainder trusts, qualified small business stock strategies, opportunity zone investments, sophisticated entity structuring, family limited partnerships, and the comprehensive strategies that separate high earners who keep their wealth from those who surrender massive amounts to taxation.

Now, I understand you came here seeking information about advanced tax strategies for high earners. And I'm absolutely going to deliver that—you'll learn about the specific strategies available to million-dollar earners, which situations benefit from each strategy, how to implement them correctly, and why generic CPAs miss these opportunities entirely.

But here's the critical information your current accountant probably isn't sharing: high-income tax planning is a specialized field requiring expertise that most CPAs simply don't have. Generic accountants handle W-2 employees earning $80,000, small business owners making $150,000, maybe professionals earning $300,000. They don't work with enough million-dollar earners to develop expertise in the advanced strategies that this income level requires.

Why I Created This High-Earner Tax Planning Guide

Most million-dollar earners in South Florida are overpaying their taxes by $75,000 to $200,000+ annually because their CPA provides competent basic services—accurate returns, reasonable deductions, proper compliance—but never implements the sophisticated strategies available to high-net-worth individuals.

The result? You're paying effective tax rates of 40-45% (federal + state where applicable + Medicare surtax) when sophisticated planning could reduce this to 25-30% or lower through legitimate, IRS-approved strategies. You're missing charitable giving strategies that provide both tax benefits and philanthropic impact. You're not utilizing entity structures that would dramatically reduce self-employment taxes. You're failing to leverage qualified opportunity zones, installment sales, charitable remainder trusts, and dozens of other advanced strategies.

Generic CPAs don't implement these strategies because:

1. They don't know they exist (not their expertise area)
2. They don't understand how to implement them properly
3. They don't have the sophisticated clients requiring them
4. They prefer simple, repeatable services over complex planning
5. They don't coordinate with estate planning attorneys, wealth advisors, and other professionals

That's the problem we solve at Whittmarsh Tax & Accounting.

We don't just prepare tax returns for anyone who walks through the door. We specifically target high-net-worth individuals earning $1 million+ who need sophisticated tax planning that most CPAs can't provide. We coordinate with your entire advisory team, implement advanced strategies, and ensure you're not leaving six figures annually on the table through inadequate planning.

What This Comprehensive Guide Delivers

First, I'm going to explain why million-dollar earners face unique tax challenges—the 37% federal bracket, the 3.8% Net Investment Income Tax, the Alternative Minimum Tax, and how these create effective rates exceeding 40% that require sophisticated planning to mitigate.

Then, I'm going to walk through the specific advanced strategies available—charitable remainder trusts providing income and deductions, qualified small business stock exclusions, opportunity zone deferrals, sophisticated entity structuring, family wealth transfer strategies, and the comprehensive planning that keeps substantially more wealth in your family rather than sending it to the IRS.

But here's my direct ask: if you're earning $1 million+ annually, if you're paying $300,000+ in federal taxes, if your current CPA has never discussed charitable trusts or opportunity zones or QSBS with you, if you suspect you're overpaying but don't know what strategies are available—we need to talk immediately.

Schedule a consultation with Whittmarsh Tax & Accounting, and let's analyze exactly how much sophisticated tax planning could save you annually and which strategies make sense for your specific situation.

You can absolutely continue writing massive checks to the IRS every year, assuming that's just the cost of success, never exploring advanced strategies. But if you're serious about wealth preservation—if you want sophisticated planning from specialists who work exclusively with high-net-worth clients—we need to have a conversation.

Call us at (305) 790-5604 or book your high-earner tax planning consultation here.

Understanding the High-Earner Tax Burden

Why Million-Dollar Earners Face Effective Rates Exceeding 40%

Before exploring strategies, you need to understand the tax burden that million-dollar earners face and why it requires sophisticated planning.

The Tax Structure for High Earners:

Federal Income Tax (2024):

Progressive brackets up to:

• 37% on ordinary income over $609,350 (married filing jointly)
• 20% on long-term capital gains over $553,850 (married filing jointly)

Additional Medicare Tax:

• 0.9% on earned income over $250,000 (married filing jointly)
• 3.8% Net Investment Income Tax (NIIT) on investment income over $250,000 (married filing jointly)

Self-Employment Tax (for business owners):

• 15.3% on self-employment income up to $168,600
• 2.9% Medicare on all self-employment income over that threshold
• Plus 0.9% additional Medicare over $250,000

State Income Tax:

• Florida: 0% (major advantage for Miami residents)
• High-tax states: Up to 13.3% (California), 10.9% (New York)

Effective Tax Rates for Million-Dollar Earners:

Example 1: $1 Million W-2 Income

Miami executive earning $1M W-2:

• Federal income tax: ~$315,000
• Additional Medicare Tax: ~$7,500
• Total federal taxes: $322,500
• Effective rate: 32.25%

Example 2: $1 Million Business Income

Miami business owner earning $1M profit:

• Federal income tax: ~$315,000
• Self-employment tax: ~$27,000 (after Social Security cap)
• Additional Medicare Tax: ~$7,500
• Total federal taxes: $349,500
• Effective rate: 34.95%

Example 3: $2 Million Mixed Income

Miami high earner with $1M W-2 + $1M investment income:

• Federal income tax on W-2: ~$315,000
• Federal income tax on investments: ~$230,000 (combination of dividends, capital gains)
• Additional Medicare Tax: ~$7,500
• NIIT (3.8% on $1M investment income): $38,000
• Total federal taxes: $590,500
• Effective rate: 29.5%

The Florida Advantage:

Million-dollar earners in Miami save substantially compared to high-tax states:

$1M income in Miami vs. California:

• California state tax: ~$133,000
• Florida state tax: $0
• Annual savings: $133,000 from residency alone

However, even with Florida's zero state tax, federal burdens require sophisticated planning.

The Alternative Minimum Tax (AMT):

High earners face potential AMT exposure:

• 26% on first $220,700 of AMT income (2024, married filing jointly)
• 28% on AMT income over $220,700
• Exemption phases out starting at $1,218,700

AMT removes many deductions (state taxes, certain deductions) and can increase effective rates further.

At Whittmarsh Tax & Accounting, we help million-dollar earners understand their complete tax picture and implement strategies reducing effective rates from 35-40% to 20-28% through sophisticated planning. Our comprehensive high-net-worth services coordinate tax, estate, and wealth planning for optimal results.

Strategy 1: Charitable Remainder Trusts (CRTs)

Generating Income While Creating Massive Tax Deductions

Charitable Remainder Trusts represent one of the most powerful strategies for high-net-worth individuals seeking both tax benefits and philanthropic impact.

How Charitable Remainder Trusts Work:

1. You transfer highly appreciated assets (stock, real estate, business interests) to an irrevocable trust
2. The trust sells assets tax-free (no immediate capital gains tax)
3. Trust pays you (and/or spouse) income for life or term of years
4. When trust terminates, remainder goes to charity
5. You receive immediate charitable deduction for present value of remainder interest

The Power of CRTs:

Example:

Miami executive owns $2 million of stock with $100,000 basis (purchased for $100,000, now worth $2 million):

Without CRT:

• Sells stock: $2 million
• Capital gains: $1,900,000
• Federal tax: $380,000 (20% capital gains)
• NIIT: $72,200 (3.8%)
• Total taxes: $452,200
• Net after-tax proceeds: $1,547,800

With Charitable Remainder Trust:

• Transfers $2 million stock to CRT
• CRT sells stock tax-free
• Full $2 million available to generate income
• CRT invests $2 million, pays 5% annually to donor
• Annual income: $100,000 for life
• Charitable deduction: ~$650,000 (present value of remainder)
• Tax savings from deduction: ~$240,500 (37% bracket)

Advantages:

• Deferred capital gains taxes (never paid)
• Immediate charitable deduction
• Lifetime income stream
• Full $2 million working instead of $1,547,800
• Philanthropic impact
• Estate tax reduction

Types of Charitable Remainder Trusts:

Charitable Remainder Annuity Trust (CRAT):

• Fixed dollar amount paid annually
• Cannot add assets after creation
• More predictable income
• Better for conservative investors

Charitable Remainder Unitrust (CRUT):

• Percentage of trust value paid annually (revalued each year)
• Can add assets over time
• Income fluctuates with trust performance
• Potential for income growth if trust appreciates

Ideal Situations for CRTs:

1. Highly Appreciated Assets: Stock with low basis, appreciated real estate, business interests
2. High Current Income: Already earning $1M+, don't need sale proceeds for living expenses
3. Charitable Intent: Want to support causes while receiving tax benefits
4. Estate Planning: Want to reduce estate size for estate tax purposes

CRT Planning Considerations:

Income Requirements:

• Minimum 5% of trust value must be paid to income beneficiaries
• Maximum 50% of trust value
• Typical range: 5-7%

Charitable Remainder:

• At least 10% of initial trust value must be projected to go to charity
• Cannot structure trust so charitable remainder is less than 10%

Irrevocability:

• Once established, cannot be revoked
• Assets permanently committed
• Requires certainty about not needing assets

Example: Real Estate CRT

Miami real estate investor owns rental property:

• Current value: $3 million
• Basis: $500,000
• Rental income: $120,000 annually
• Wants to exit real estate, generate retirement income

Traditional Sale:

• Capital gains: $2,500,000
• Taxes: ~$550,000
• Net: $2,450,000 available to invest

CRT Strategy:

• Transfer property to CRT
• CRT sells tax-free
• $3 million available to invest
• 5% payout = $150,000 annually
• Charitable deduction: ~$900,000
• Tax savings: ~$333,000

Result:

• Higher annual income ($150,000 vs. $122,500 from $2,450,000 invested at 5%)
• Massive tax savings
• Philanthropic legacy

At Whittmarsh Tax & Accounting, we coordinate with estate planning attorneys specializing in charitable trusts to structure CRTs properly for our high-net-worth clients. This requires collaboration between CPA, attorney, and wealth advisor.

Strategy 2: Qualified Small Business Stock (QSBS) Exclusion

Excluding Up to $10 Million in Capital Gains Tax-Free

Section 1202 provides one of the most powerful tax benefits for investors and entrepreneurs—potential exclusion of 100% of capital gains on qualified small business stock.

QSBS Requirements:

To qualify for exclusion, stock must meet:

1. Qualified Small Business:
   • C-Corporation
   • Gross assets under $50 million when stock issued and immediately after
   • Active business (not passive investment)
   • Not certain excluded industries (financial services, hospitality, farming, etc.)
2. Original Issuance:
   • Acquired directly from corporation (not secondary purchase)
   • Acquired in exchange for money, property, or services
3. Holding Period:
   • Must hold at least 5 years
4. Active Business Test:
   • Corporation must use at least 80% of assets in active business

The Exclusion Benefit:

For stock acquired after September 27, 2010:

• 100% of gain excluded (not just 50% or 75% from earlier dates)
• Maximum exclusion: Greater of $10 million or 10× adjusted basis
• No AMT preference item (unlike earlier QSBS)

Example:

Miami entrepreneur starts tech company in 2019:

• Invests $100,000 for founder shares
• Company grows successfully
• 2024: Company acquired for $8 million
• Entrepreneur's shares: $6 million

Without QSBS:

• Capital gain: $5,900,000
• Federal tax: $1,180,000 (20%)
• NIIT: $224,200 (3.8%)
• Total taxes: $1,404,200
• Net after-tax: $4,595,800

With QSBS (if qualified):

• Capital gain: $5,900,000
• QSBS exclusion: $5,900,000 (under $10M limit)
• Taxable gain: $0
• Total taxes: $0
• Net after-tax: $6,000,000

Tax savings: $1,404,200

The $10 Million per Taxpayer Rule:

Each taxpayer can exclude up to $10 million per qualifying corporation:

• Married couple: $20 million exclusion (each spouse can exclude $10 million)
• Multiple qualified businesses: $10 million exclusion for each

Example: Multiple Companies

Entrepreneur starts three companies over years, each qualifies as QSBS:

• Company A sold: $8 million gain → $8 million excluded
• Company B sold: $10 million gain → $10 million excluded
• Company C sold: $15 million gain → $10 million excluded, $5 million taxable

Total exclusion: $28 millionTax savings: ~$6 million

Strategic QSBS Planning:

For Entrepreneurs Starting Companies:

• Structure as C-Corporation (not LLC or S-Corp)
• Ensure company stays under $50 million gross assets
• Hold shares at least 5 years
• Maintain 80% active business test
• Plan exit timing (must hold 5+ years)

For Investors in Startups:

• Invest in qualified C-Corporations
• Original issuance only (not secondary shares)
• Document qualification at time of investment
• Hold 5+ years minimum

For Existing Business Owners:

• Consider whether current business qualifies
• If LLC or S-Corp, evaluate conversion to C-Corp
• Analyze whether QSBS benefits exceed C-Corp double taxation costs
• Plan holding period before any sale

QSBS and Estate Planning:

QSBS benefits transfer to heirs:

• Gifts of QSBS to family members maintain qualification
• Recipients' holding period includes donor's period
• Allows wealthy families to multiply QSBS benefits across multiple taxpayers

Example:

Entrepreneur with $50 million QSBS-qualifying company:

• Gifts shares worth $20 million to spouse
• Gifts shares worth $10 million to two children
• Family now has 4× $10 million exclusions = $40 million
• Potential tax savings: ~$8 million vs. entrepreneur holding all shares

At Whittmarsh Tax & Accounting, we help entrepreneurs and investors evaluate QSBS opportunities, structure businesses to maintain qualification, plan holding periods, and coordinate with estate planning for maximum family benefit.

Strategy 3: Qualified Opportunity Zones (QOZs)

Deferring and Reducing Capital Gains Through Strategic Investments

Qualified Opportunity Zones provide powerful tax benefits for investors with capital gains seeking tax deferral and reduction.

How Opportunity Zones Work:

1. Realize capital gain from any source
2. Invest gain in Qualified Opportunity Fund within 180 days
3. Defer capital gains tax until December 31, 2026 (or earlier if investment sold)
4. Hold investment 5+ years: Reduce deferred gain by 10%
5. Hold investment 7+ years: Reduce deferred gain by additional 5% (total 15%)
6. Hold investment 10+ years: New investment gain is 100% tax-free

The Triple Tax Benefit:

1. Deferral: No tax on original gain until 2026 or sale
2. Reduction: 10-15% reduction in original gain if held long enough
3. Exclusion: 100% exclusion of new appreciation if held 10+ years

Example:

Miami investor sells stock in 2024:

• Capital gain: $1,000,000
• Tax due: $238,000 (23.8% with NIIT)

Traditional Approach:

• Pays $238,000 immediately
• Invests remaining $762,000

Opportunity Zone Strategy:

• Invests full $1,000,000 in QOZ fund within 180 days
• Defers $238,000 tax until 2026
• Holds investment 10 years

Benefits:

• Full $1,000,000 working (not $762,000)
• If held through 2031 (7+ years from 2024):
  • Original $1 million gain reduced by 15% = $850,000 taxable
  • Tax savings: ~$35,700
• QOZ investment appreciation:
  • Original $1 million grows to $2 million (example 7.2% annual return)
  • $1 million appreciation is 100% tax-free
  • Tax savings: ~$238,000

Total tax savings: ~$273,700

Qualified Opportunity Zones in South Florida:

Many Miami and South Florida areas designated as Opportunity Zones:

• Parts of Liberty City
• Overtown
• Little Havana
• Parts of Fort Lauderdale
• Parts of West Palm Beach

Investment Opportunities:

QOZ investments typically involve:

• Real estate development projects
• Business operations in zones
• Mixed-use developments
• Operating businesses (not just real estate)

QOZ Funds:

Investors access Opportunity Zones through Qualified Opportunity Funds:

Direct Investment:

• Form own QOF and invest directly in property or business
• Maximum control
• Requires expertise and significant capital

Fund Investment:

• Invest in professionally managed QOF
• Diversification across multiple projects
• Professional management
• Lower minimum investments ($100,000-$500,000 typically)

Critical Timing Requirement:

Must invest capital gain proceeds in QOF within 180 days of gain recognition. Missing this deadline eliminates deferral benefit.

Example Planning:

Miami high earner sells business in June 2024:

• Gain: $3 million
• Has until December (180 days) to invest in QOF
• Works with advisor to identify appropriate QOF investment
• Invests $3 million in diversified QOZ real estate fund
• Holds through 2034 (10+ years)

Benefits:

• Defers $714,000 tax until 2026
• Reduces original gain by 10% (missed 7-year mark for full 15%)
• New appreciation tax-free after 10 years

QOZ Due Diligence:

Critical factors in evaluating QOZ investments:

• Track record of sponsor/developer
• Specific project details and feasibility
• Market analysis for the zone
• Projected returns
• Liquidity provisions
• Fee structures

Warning: Some QOZ funds have been marketed aggressively with questionable projects. Require thorough due diligence.

At Whittmarsh Tax & Accounting, we help clients evaluate QOZ opportunities, coordinate timing of capital gains and QOF investments, and analyze whether deferral and potential appreciation exclusion justify the investment.

Strategy 4: Advanced Entity Structuring for Business Owners

Sophisticated Structures That Reduce Taxes and Protect Assets

High-earning business owners benefit from sophisticated entity structures beyond basic LLC or S-Corporation.

Beyond Basic Structures:

Strategy: S-Corp + Management Company + Real Estate Holding Entities

Structure:

1. Operating S-Corporation:
   • Primary business operations
   • Pays owner reasonable compensation
   • Distributes remaining profits
2. Management Company (LLC or S-Corp):
   • Provides management services to operating company
   • Owned by spouse or family
   • Employs family members
   • Pays reasonable compensation to family
3. Real Estate Holding LLC(s):
   • Own business real estate
   • Lease to operating company
   • Rental income not subject to self-employment tax
   • Separate liability protection

Example:

Miami medical practice earning $2 million annually:

Basic Structure (S-Corp only):

• Reasonable compensation: $400,000
• Distributions: $1,600,000
• Payroll taxes: $61,200 (on $400,000)

Advanced Structure:

Operating S-Corp:

• Revenue: $2,000,000
• Management fee to spouse's company: $250,000
• Rent to real estate LLC: $150,000
• Operating profit: $1,600,000
• Owner compensation: $350,000
• Distributions: $1,250,000

Management Company (owned by spouse):

• Management fee received: $250,000
• Employs owner's children (3 kids × $15,000): $45,000
• Spouse compensation: $100,000
• Company profit: $105,000

Real Estate LLC (owned by owner):

• Rental income: $150,000
• Expenses: $30,000
• Net rental income: $120,000
• No self-employment tax

Tax Analysis:

Total income to family: $2,000,000 (same as before)

Tax Savings:

• Shifted $250,000 to management company (some to children's lower brackets)
• $150,000 rental income not subject to SE tax: Saves $22,950
• Children employed: $45,000 in their low/zero brackets
• Total family tax savings: ~$45,000+ annually

Plus:

• Asset protection from entity separation
• Estate planning benefits from spreading wealth
• Retirement contributions across entities

Family Limited Partnerships (FLPs):

For very high net worth business owners and investors:

Structure:

• Parents create FLP
• Transfer assets (business interests, real estate, investments) to FLP
• Parents retain 1-2% as general partners (control)
• Gift limited partner interests to children/trusts (98-99%)

Benefits:

• Valuation discounts (30-40% for lack of control, lack of marketability)
• Centralized asset management
• Asset protection
• Estate tax reduction
• Income shifting to lower brackets

Example:

Miami business owner with $10 million business:

• Transfers business to FLP
• Gifts 49% LP interests to children (over several years using gift tax exemptions)
• With 35% valuation discount: $10M × 49% × 65% = $3,185,000 gift value
• Actual value transferred: $4,900,000
• Estate tax savings: ~$1,714,000 (difference × 40% estate tax)

Holding Company Structures:

For multiple businesses or investment properties:

Structure:

• Parent holding company (LLC or S-Corp)
• Subsidiary entities for each business/property
• Centralized management and cash management
• Consolidated financial reporting

Benefits:

• Asset protection (each subsidiary isolated)
• Tax flexibility
• Easier to sell individual businesses
• Professional presentation for investors/acquirers

At Whittmarsh Tax & Accounting, we design sophisticated entity structures for high-net-worth business owners, coordinating with business attorneys and wealth advisors to create structures that minimize taxes, protect assets, and facilitate wealth transfer.

Strategy 5: Installment Sales and Deferred Payment Strategies

Spreading Capital Gains Over Multiple Years

High earners selling businesses or appreciated assets can defer taxation through installment sales.

How Installment Sales Work:

Instead of receiving full payment at closing:

• Buyer pays portion at closing
• Remaining paid over time (installments)
• Seller recognizes gain proportionally as payments received
• Spreads tax burden over multiple years

Benefits:

1. Tax Deferral: Pay taxes as receive income, not all upfront
2. Rate Arbitrage: If tax rates increase in future, locked in sale but spread taxes
3. Cash Flow Management: Steady income stream rather than lump sum
4. Investment Flexibility: Time to reinvest proceeds strategically

Example:

Miami business owner sells business:

• Sale price: $5 million
• Basis: $500,000
• Capital gain: $4,500,000

Traditional Sale:

• Receives $5 million at closing (after deducting basis)
• Pays tax on $4.5 million gain: ~$1,071,000
• Net after-tax: $3,929,000

Installment Sale:

• Receives $1 million at closing
• Remaining $4 million paid over 4 years ($1M/year)

Year 1:

• Cash received: $1 million
• Gain recognized: $900,000 ($1M × 90% gain ratio)
• Tax: ~$214,200

Years 2-5:

• Each year: $900,000 gain recognized
• Each year tax: ~$214,200

Advantages:

• Spreads tax burden over 5 years
• Time to plan distributions to minimize tax impact
• Interest earned on unpaid balance (typically required by IRS)
• Cash flow management

Installment Sale Considerations:

Interest Requirements:

• IRS requires interest on installments
• Minimum rate: Applicable Federal Rate (AFR)
• Interest is ordinary income (not capital gain)

Security:

• Buyer's promise to pay is security
• Risk of buyer default
• Consider promissory note terms, guarantees, collateral

Depreciation Recapture:

• Cannot use installment method for depreciation recapture
• Depreciation recapture taxed in year of sale (not deferred)

Related Party Sales:

• Special rules for sales to related parties
• If related party sells within 2 years, can accelerate gain recognition

Self-Canceling Installment Notes (SCINs):

Variation allowing estate planning benefits:

Structure:

• Installment note includes provision: if seller dies before fully paid, remaining balance cancels
• Premium charged (higher interest or larger payment) for cancellation provision

Benefits:

• Asset transferred to buyer
• If seller dies, unpaid balance not in estate
• Estate tax savings on unpaid amount

Example:

$5 million business sale with SCIN:

• Normal installment: $1M/year for 5 years
• SCIN: $1.1M/year for 5 years (premium for death cancellation)
• Seller dies after year 3
• Remaining $2.2 million cancels (not in estate)
• Estate tax savings: ~$880,000

At Whittmarsh Tax & Accounting, we structure installment sales for high-net-worth clients selling businesses or appreciated assets, analyzing whether deferral benefits justify the risks and costs of extended payout structures.

The Stakes: What Million-Dollar Earners Lose Through Generic CPA Services

Real Numbers on Inadequate High-Net-Worth Tax Planning

Let's quantify what inadequate tax planning costs million-dollar earners.

Example: $2 Million Annual Income High Earner

Profile:

• Business owner: $1.5 million business income
• Investment income: $500,000
• Total income: $2 million
• Works with generic CPA: competent returns, basic compliance, no advanced strategies

Costs of Inadequate Planning:

Missed S-Corp Optimization:

• Operating as LLC taxed as partnership
• Excess self-employment taxes: $25,000 annually

No Charitable Planning:

• Gives $50,000 annually to charity via cash
• Could have gifted appreciated stock (basis $10,000, FMV $50,000)
• Missed tax savings: ~$10,000 (avoided capital gains + deduction at higher value)

No Entity Restructuring:

• Single entity for all operations
• Could split operating/management/real estate
• Missed family income shifting: ~$15,000 annually

No Investment Tax Optimization:

• High turnover in taxable investment accounts
• Short-term gains instead of long-term
• Excess taxes: ~$20,000 annually

No Estate Planning Integration:

• No family limited partnership
• Missing valuation discounts
• Future estate tax excess: ~$200,000+ (over lifetime)

Not Utilizing Opportunity Zones:

• Had $800,000 capital gain, paid taxes immediately
• Could have deferred + excluded appreciation
• Missed savings: ~$100,000+ over 10 years

Annual Excess Taxes: $70,000+

Over 10 years: $700,000+ in unnecessary taxes

Plus: Estate tax inefficiencies worth hundreds of thousands more

Compare to Sophisticated Planning:

Whittmarsh Comprehensive Planning:

• Annual planning fee: $15,000
• Tax savings implemented: $70,000+ annually
• Net annual benefit: $55,000+
• ROI: 367%

Over 10 years:

• Planning fees: $150,000
• Tax savings: $700,000+
• Net benefit: $550,000+

The numbers are stark. Generic CPA services cost million-dollar earners enormous amounts through missed advanced strategies.

High-Net-Worth Tax Planning: Frequently Asked Questions

At what income level do I need specialized high-net-worth tax planning?

Generally, once you're earning $500,000-$1 million+, basic CPA services become inadequate. At this income level, you face top tax brackets, additional Medicare taxes, potential AMT, and the sophisticated strategies available at this income level justify the cost of specialized planning. At Whittmarsh Tax & Accounting, we work primarily with clients earning $1 million+ who need advanced strategies beyond what generic CPAs provide.

How much do advanced tax planning services cost?

Comprehensive high-net-worth tax planning typically costs $10,000-$30,000+ annually depending on complexity. This includes year-round planning, quarterly strategy meetings, advanced strategy implementation, coordination with other advisors, and comprehensive tax preparation. The ROI is typically 5-20× through tax savings implemented, making sophisticated planning an investment that pays for itself many times over.

Can these strategies get me audited?

All strategies we implement are completely legal and IRS-approved. Charitable remainder trusts, QSBS, opportunity zones, installment sales—these aren't "aggressive" strategies, they're legitimate provisions in the tax code. However, high-income returns naturally face higher audit rates regardless of strategies used. The key is proper implementation and documentation, which we ensure.

Do I need to be charitably inclined to use CRTs?

Yes, CRTs are appropriate only for individuals who genuinely want to support charitable causes. The charitable remainder goes to charity—this isn't a strategy to avoid that requirement. If you have zero charitable intent, CRTs aren't appropriate. However, if you're already charitably inclined and have highly appreciated assets, CRTs provide extraordinary tax benefits alongside your philanthropic goals.

What if I already sold my business and paid the taxes?

Unfortunately, most strategies require advance planning before transactions occur. Once you've sold and paid taxes, you cannot retroactively implement deferral strategies. This is why consulting with specialized advisors before major transactions is critical. However, we can still implement strategies going forward to minimize future taxes and maximize wealth preservation.

How do you coordinate with my other advisors?

High-net-worth planning requires coordination among CPAs, estate attorneys, wealth advisors, insurance specialists, and others. We regularly collaborate with our clients' existing advisors, participating in joint meetings and ensuring all professionals are aligned. If you don't have a complete advisory team, we can recommend specialists we trust who serve high-net-worth clients.

Are there strategies specific to business owners vs. W-2 high earners?

Yes, business owners have additional opportunities like entity restructuring, family employment, captive insurance, and others not available to W-2 employees. However, W-2 high earners still benefit from charitable strategies, investment optimization, opportunity zones, and estate planning strategies. We customize recommendations based on your income sources.

What about cryptocurrency and digital asset tax strategies?

Digital assets create unique opportunities and challenges for high-net-worth individuals. Strategies include timing of gains/losses, charitable giving of crypto, opportunity zone investments from crypto gains, and estate planning considerations. We've developed expertise in cryptocurrency taxation serving Miami's significant crypto investor community.

Can these strategies help reduce estate taxes too?

Absolutely. Many strategies provide both income tax and estate tax benefits. CRTs reduce estate size. Family limited partnerships provide valuation discounts. QSBS can benefit heirs. Installment sales can utilize SCINs for estate tax planning. Comprehensive planning addresses both income and estate tax optimization simultaneously.

What if I'm planning to leave Florida?

Florida's zero state income tax is a major advantage for high earners. Moving to high-tax states like California or New York could cost you hundreds of thousands annually in state taxes. We help clients evaluate the true after-tax cost of relocations and, if moves are necessary, implement strategies to minimize state tax exposure (establishing proper residency, timing of move around income recognition, etc.).

Take the Next Step: Schedule Your High-Net-Worth Tax Planning Consultation

You now understand the sophisticated strategies available to million-dollar earners and how generic CPA services leave enormous amounts on the table. The question is: what will you do with this knowledge?

You have two clear options:

Option 1: Continue with your current generic CPA, writing checks for $300,000-$500,000+ annually to the IRS, assuming that's just what high earners pay, never exploring the advanced strategies that could save you $50,000-$200,000+ annually, and leaving hundreds of thousands on the table over your high-earning years.

Option 2: Schedule a consultation with Whittmarsh Tax & Accounting and discover exactly which advanced strategies apply to your situation. Get comprehensive analysis from specialists who work exclusively with high-net-worth clients. Implement strategies that keep substantially more wealth in your family rather than surrendering it to taxation.

The consultation is straightforward. We'll review your current income sources and tax situation, identify which advanced strategies apply to you, quantify potential savings, explain implementation requirements, and provide honest assessment of ROI.

For million-dollar earners, sophisticated tax planning isn't a luxury—it's the difference between building generational wealth and surrendering massive amounts unnecessarily to taxation.

Book your high-net-worth tax planning consultation: https://www.whittmarsh.com/pricing-how-it-works

Our Aventura office specializes in serving high-net-worth individuals earning $1 million+ annually. We've saved our clients millions cumulatively through advanced planning strategies that generic CPAs never implement.

Whittmarsh Tax & Accounting: South Florida's High-Net-Worth Tax Specialists

We specifically target million-dollar earners who need sophisticated tax planning beyond what generic CPAs provide. Our ideal clients include:

• Individuals earning $1 million+ annually
• High-net-worth business owners and entrepreneurs
• Successful professionals in top tax brackets
• Investors with substantial capital gains
• Anyone paying $300,000+ in federal taxes annually
• High earners frustrated with generic tax advice

We provide comprehensive high-net-worth tax services including:

• Charitable remainder trust planning and implementation
• QSBS qualification analysis and optimization
• Opportunity zone investment coordination
• Advanced entity structuring for business owners
• Family limited partnership establishment
• Installment sale structuring
• Investment tax optimization
• Estate tax integration
• Year-round strategic planning
• Coordination with estate attorneys and wealth advisors

Our mission is helping South Florida's high-net-worth individuals keep more of what they earn through sophisticated, legitimate tax strategies that generic CPAs either don't know about or don't have expertise to implement.

If you're earning $1 million+ annually, you owe it to yourself to explore whether you're implementing all available strategies or leaving six figures on the table through inadequate planning.

Visit us online at www.whittmarsh.com

Whittmarsh Tax & Accounting serves high-net-worth individuals throughout Miami, Aventura, Fort Lauderdale, and all of South Florida. We specialize in advanced tax strategies for million-dollar earners including charitable planning, QSBS optimization, opportunity zones, sophisticated entity structures, and comprehensive strategies that preserve wealth rather than surrendering it unnecessarily to taxation.