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Tax Planning & Compliance — High Earners & Business Owners

The right tax strategy
is worth more than
a good accountant.

We provide strategic tax planning and full compliance services for high-income business owners, serial entrepreneurs, physicians, real estate investors, and high-net-worth families. Not reactive. Not one-size-fits-all. Built around your specific situation and updated every year as your situation changes.

There is a significant difference between filing your taxes and planning your taxes. Filing is compliance — it documents what already happened. Planning is strategy — it changes what will happen before the year closes, before the transaction executes, before the structure is set.

For high-income earners with complex situations, the gap between what you pay in taxes with a reactive CPA and what you would pay with proactive planning can be $50,000, $150,000, or several hundred thousand dollars per year. That gap compounds every year you do not address it.

Our tax services are built for clients whose situations require genuine expertise: multiple entities, S corporations and partnerships, real estate portfolios with depreciation positions, retirement plans, equity compensation, estate planning integration, and the kind of income that makes every planning decision consequential.

$200K+
Annual deduction from a properly designed cash balance plan for a business owner earning $750K — that is $74,000+ in federal tax reduction, every year
$300K
Approximate first-year federal tax savings from a cost segregation study on a $3M commercial building — an analysis we conduct in-house
$72K/yr
Annual tax reduction for a physician household ($680K income) when the spouse qualifies for the real estate professional election on their rental portfolio
$2.975M
Federal capital gains tax eliminated on a $12.5M company exit via the QSBS Section 1202 exclusion — available to qualifying C corporation founders
Individual Tax Planning & Compliance
Your personal return is where every strategy either works or does not.
For high-income earners, the individual Form 1040 is not a simple document — it is where your S corporation income, your rental property losses, your retirement plan deductions, your grantor trust income, your charitable deductions, and your capital gains all converge. Getting this return right requires understanding every piece of the puzzle simultaneously.

Form 1040 — Individual Income Tax

Comprehensive preparation integrating all income sources — W-2, partnership and S corp K-1s, Schedule C, Schedule E rental income, Schedule D capital gains, qualified dividends, and all applicable deductions. We prepare the return as the downstream output of a planning process, not the starting point.

Passive Activity and REP Election

Proper treatment of passive versus non-passive activity under §469, management of suspended passive loss carryforwards, and — for qualifying households — the real estate professional election that converts passive losses into direct offsets against all ordinary income. We maintain the time log protocol and documentation for every REP election client.

How the REP Election Works →

Qualified Business Income Deduction §199A

The permanent 20% deduction on qualifying pass-through income requires careful analysis of SSTB classification, W-2 wage limitations, and the interaction between multiple entities. We model the optimal structure for maximum QBI benefit — entity by entity, year by year.

Capital Gains Planning

Timing and structuring of capital gains to minimize rate exposure — coordinating installment sales, QSBS exclusions, charitable remainder trusts, and opportunity zone reinvestment. We model every significant asset sale before it happens to ensure it is structured optimally.

QSBS Section 1202 Explained →

Grantor Trust Income Reporting

Every irrevocable grantor trust — SLATs, IDGTs, GRATs — requires a grantor trust statement attached to your Form 1040. We prepare these statements and integrate all trust income correctly into your personal return. Clients with multiple trust structures rely on us to ensure each one is properly reported.

Alternative Minimum Tax (AMT) Management

For high-income taxpayers, AMT exposure requires year-round monitoring. We model AMT liability alongside regular tax, identify preference items, and plan around the interaction of ISO exercises, depreciation, and other AMT-sensitive items.

Business Tax Planning & Compliance
The structure of your business determines how much of your income you actually keep.
Entity selection, compensation structure, retirement plan design, depreciation strategy, and inter-entity planning decisions collectively determine whether you pay 22% or 37% on each dollar of business income. These are not accounting questions — they are planning questions that must be answered before the year begins.

S Corporation Strategy & Compliance

Reasonable compensation analysis, distribution structuring to maximize QBI deduction and minimize FICA, fiscal year planning, and coordination with retirement plan contributions. We prepare Forms 1120-S, K-1s for all shareholders, and the owner's personal return as one coordinated package — not three separate engagements.

Partnership & LLC Tax Returns

Form 1065 preparation for partnerships, multi-member LLCs, and family limited partnerships. We handle complex allocations, guaranteed payments, §704(b) capital account maintenance, partnership basis tracking, and the annual K-1 issuance to all partners. For FLPs, we coordinate with the annual gifting program and appraisal cycle.

C Corporation & QSBS Planning

For founders considering or maintaining C corporation status for QSBS eligibility, we advise on the tax trade-offs — double taxation at the entity level vs. Section 1202 capital gains exclusion at exit. We track the QSBS holding period and coordinate pre-sale analysis with M&A counsel years before an exit materializes.

QSBS Strategy Guide →

Multi-Entity Architecture

Serial entrepreneurs and business owners with multiple entities — operating companies, holding companies, real estate entities, management companies — benefit from coordinated inter-entity planning. We map every entity, every income flow, and every deduction to ensure the overall structure is optimized rather than assembled by accident.

R&D Tax Credits §41

Dollar-for-dollar credits against tax liability for qualifying research activities. We conduct the qualifying activity analysis, maintain documentation protocols throughout the year, and prepare Form 6765 in-house — avoiding the contingency fee model of third-party R&D firms that draws IRS scrutiny. Manufacturers, technology companies, medical practices, and construction firms routinely qualify.

Cost Segregation Studies

Conducted entirely in-house — no outsourcing to third-party engineering firms. We analyze commercial properties and identify components qualifying for accelerated 5-, 7-, and 15-year depreciation, all eligible for 100% bonus depreciation in Year 1 under permanent law. Study findings integrate directly with Form 4562 on your return — zero handoff risk.

Cost Segregation Guide →

Retirement Plan Design & Compliance

Defined benefit and cash balance plan design for business owners — $200,000 to $300,000+ in annual deductions, far exceeding 401(k) limits. We coordinate with enrolled actuaries, prepare Form 5500 annually, and ensure the plan operates within IRS requirements. For business owners in their 50s with high income, this is typically the highest-value single strategy available.

Defined Benefit Plan Guide →

Business Sale & Exit Tax Planning

Pre-sale estate planning (60-to-90-day lead time minimum), deal structure optimization (asset vs. stock sale analysis), personal goodwill allocation, installment sale structuring, and QSBS exclusion coordination. We work with M&A counsel to ensure every decision in the sale process has been analyzed for tax impact before it is made — not after.

Estate, Gift & Trust Tax Compliance
Every trust you create. Every gift you make. Every filing it requires — handled by one team.
The complexity of estate planning is not in creating the structures — it is in operating them correctly, year after year, with every filing coordinated and every deadline met. We prepare every trust, gift, and estate return as part of a unified compliance practice, not as isolated transactions.

Form 709 — Gift Tax Returns

Required for every transfer that uses lifetime exemption, every split gift, every Crummey trust contribution, and every gift of FLP or other discounted interests. We prepare every Form 709 with adequate disclosure — the specific documentation that starts the IRS statute of limitations. Without adequate disclosure, the IRS can challenge a gift's value indefinitely.

Form 1041 — Trust Income Tax Returns

Annual income tax returns for non-grantor trusts — SLATs after the grantor's death, dynasty trusts, charitable remainder trusts (Form 5227), and any other irrevocable trust holding income-producing assets. We advise the trustee annually on the distribution vs. retention decision — compressed trust tax brackets vs. beneficiary individual rates.

Form 5227 — CRT Annual Returns

Charitable Remainder Trusts require Form 5227 annually by April 15 with no automatic extension. This is the most strictly deadline-managed return in our practice. We begin CRT return preparation in March for every client and have never missed this deadline. Late filing is $20 per day.

Form 706 — Estate Tax Returns

Federal estate tax returns for decedents' estates, including portability elections preserving the deceased spouse's unused exemption. We prepare the 706 in coordination with the estate attorney, ensuring all assets are properly valued, all deductions claimed, and the step-up in basis is fully documented for every asset in the estate.

Grantor Trust Statements

Every grantor trust — SLAT, IDGT, GRAT — requires an annual statement attached to the grantor's Form 1040 identifying all income items flowing from the trust. We prepare these statements as standard practice for every client with irrevocable grantor trusts in their plan.

Annual Crummey Notice Management

For clients with ILITs and other trusts requiring Crummey powers, we draft, send, and maintain documentation of every Crummey withdrawal notice — for every beneficiary, every contribution, every year. The notice file is maintained in your permanent record and is available immediately if the annual exclusion is ever examined.

Who This Is Built For
Six client profiles we serve exceptionally well.
Profile 01
The Physician or Medical Practice Owner
High W-2 or K-1 income with passive real estate losses that are not being used. A spouse who manages properties. A medical practice that could benefit from a defined benefit plan. Real estate purchases that need cost segregation.
Common strategies: REP election, cost seg, DB plan, SLAT, FLP
Profile 02
The Serial Entrepreneur
Multiple entities — operating companies, holding companies, real estate LLCs, investment vehicles. Each entity was formed for a reason but the tax architecture was never planned holistically. Significant income from various sources.
Common strategies: Entity architecture, S corp optimization, DB plan, cost seg, QSBS analysis
Profile 03
The Real Estate Investor
Active portfolio of commercial or residential properties. Cost segregation not yet conducted on most of the portfolio. Passive losses sitting as carryforwards. Estate transfer plan for a growing asset base not yet in place.
Common strategies: Cost seg, REP election, FLP, IDGT installment sale, 1031 coordination
Profile 04
The Pre-Exit Founder
Company is growing, an exit is 2 to 5 years away, and the tax planning has not started. QSBS eligibility may exist but has never been formally analyzed. No pre-sale estate planning in place. Deal structure never modeled.
Common strategies: QSBS analysis, 83(b) election, pre-sale SLAT/IDGT, deal structure optimization
Profile 05
The Attorney or Law Firm Partner
High partnership income with significant self-employment tax exposure. Real estate holdings with a qualifying spouse. Estate plan started but not maintained. No coordinated annual planning between tax and estate advisors.
Common strategies: S corp election analysis, DB plan, REP election, SLAT, annual gifting
Profile 06
The High-Net-Worth Family
Estate growing beyond the exemption. Estate plan either nonexistent, outdated, or designed without coordinating the ongoing compliance. Significant gifting opportunity that is not being maximized. No one coordinating strategy with execution.
Common strategies: SLAT/IDGT, dynasty trust, FLP, annual gifting, CRT/DAF, ILIT

What standard tax firms provide

  • Annual return preparation after the year is closed
  • Reactive advice — you call with a question, they answer it
  • Separate advisors for tax, estate, and investments who never talk to each other
  • Generic strategies applied without modeling your specific numbers
  • No proactive Q4 planning before year-end deadlines
  • Outsourced cost segregation, adding fees and translation risk
  • No documentation system for examination-sensitive strategies
  • No one tracking every deadline across your complete plan

What we provide

  • Proactive planning before the year closes — modeling, not reporting
  • Direct access to our team throughout the year for real-time decisions
  • One team coordinating tax, estate, retirement plan, and compliance
  • Every strategy modeled with your actual numbers before implementation
  • Q4 tax projection and year-end action plan — every year
  • In-house cost segregation — no outsourcing, no third-party fees
  • Complete documentation systems for every examination-sensitive position
  • Every deadline tracked across your complete plan, every year
Common questions about our tax services
Answers to what high-income clients typically ask when they are evaluating whether a more strategic tax relationship makes sense for their situation.
How much can proactive tax planning actually save me compared to a standard CPA? +
It depends entirely on your situation, but for a business owner earning $700,000 to $1 million per year, proactive planning typically identifies $50,000 to $200,000 of annual tax reduction that a reactive firm is not capturing. This comes from coordinating the real estate professional election ($72,000–$100,000 per year for qualifying physician households), properly designing a defined benefit plan ($75,000–$110,000 per year), conducting cost segregation on commercial property acquisitions ($100,000–$300,000 in year of purchase), and optimizing S corporation compensation and QBI deduction structure ($15,000–$40,000 per year). These are not exotic strategies — they are well-established, IRS-accepted tools that many high-income taxpayers are not using because no one has modeled them against their specific numbers.
I already have a CPA. Why would I switch? +
Most of our clients do not switch CPAs because their current CPA is incompetent — they switch because their situation has grown beyond what a generalist firm is designed to handle. A firm that handles hundreds of returns cannot spend the hours required to design a real estate professional election protocol, model a cost segregation study on a new acquisition, track every grantor trust statement across multiple irrevocable trusts, and manage the annual Crummey notice cycle for three ILITs — all while maintaining the documentation needed for examination defense. Complexity requires a firm designed for complexity.
What is the difference between tax avoidance and tax evasion, and where does your planning sit? +
Tax evasion is illegal — it involves hiding income, falsifying records, or making fraudulent claims. Tax avoidance is the legal use of provisions in the tax code to reduce your tax liability — it is specifically what Congress intended when it created deductions, exclusions, and special rules. Every strategy we use is grounded in the Internal Revenue Code with a specific statutory or regulatory basis. We are not creating schemes — we are reading the law and using it as it was written. The IRS's own guidance acknowledges that taxpayers are entitled to arrange their affairs to minimize taxes within the law.
Do you work with clients who have already been audited or are currently under examination? +
Yes. Examination defense is a service we provide for clients under IRS or state examination. Clients who come to us mid-examination often face the challenge that their prior advisor did not maintain adequate documentation for the positions being examined — particularly for real estate professional elections, cost segregation studies, FLP valuation discounts, and conservation easements. We assess the available documentation, identify what can be reconstructed, and work with the examining agent. We cannot guarantee outcomes, but we have successfully defended all of these positions for clients who had adequate documentation from the start.
How do you handle clients with very complex multi-entity structures — 5, 10, or more entities? +
Multi-entity architecture is where a coordinated approach creates the most value — and where the gaps between advisors who do not talk to each other create the most problems. We begin with a complete entity map: what each entity is, what it does, what it earns, how income flows, and how it integrates with the owner's personal return and estate plan. From that map, we identify the structural inefficiencies — entities that should be collapsed, income that should flow through a different structure, depreciation that should be captured at a different level — and model the impact of each change before any restructuring is done. Serial entrepreneurs often find that 20% of their entities are creating 80% of their complexity without commensurate tax benefit.
How does your monthly fee structure work, and what does it cover? +
Our engagement structure varies by package and complexity level, but all ongoing client relationships include a monthly advisory fee that covers the coordination work that cannot be done once a year at tax time. This includes quarterly check-ins, real-time availability for decisions that arise throughout the year (a property acquisition, an equity grant, a distribution decision), deadline tracking across all strategies in your plan, Q4 tax projection and year-end planning, and ongoing documentation maintenance for examination-sensitive positions. The compliance work — return preparation — is a separate engagement component. We structure it this way because the advisory work and the compliance work require different rhythms, and bundling them into one annual fee incentivizes exactly the reactive behavior we are trying to avoid.

Ready to see what your situation actually looks like?

Submit an application. Tell us about your income structure, your entities, and what is not working. We review every application personally and respond within 72 hours.

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