Questions, answered.

High-net-worth tax planning is the practice of designing entity structures, timing decisions, and investment vehicles to minimize lifetime tax — not just this year's return. It typically combines federal, state, estate, and gift planning into one coordinated framework. For most $2M+ income clients, the median 5-year reduction we deliver is in the seven figures.

At least 36 months before any liquidity event, ideally at company formation. Many of the most powerful tools — Section 1202 QSBS, GRATs, intentionally defective grantor trusts, charitable structures — require holding periods, valuation timing, or pre-transaction implementation. Showing up six months before a sale leaves most of the planning on the table.

Qualified Small Business Stock (Section 1202) allows eligible founders, employees, and early investors to exclude up to 100% of capital gain on the sale of qualified C-corp stock. The per-issuer exclusion cap is generally the greater of $10M (per taxpayer) or 10x the taxpayer's adjusted basis in the stock. To qualify, the stock must be held more than 5 years, the company must have been a domestic C-corp with under $50M in gross assets when the stock was issued, and the company must operate in a qualified trade or business. Properly structured non-grantor trusts and family planning can sometimes multiply the per-taxpayer cap; this requires careful pre-issuance planning.

An 83(b) election lets you elect to pay ordinary income tax on the value of restricted equity at grant rather than at vesting. For founders receiving low-FMV stock at formation, this typically means paying tax on a tiny number now to lock in capital gain treatment later. The election must be filed with the IRS within 30 days of grant — there are no extensions, and missing the window cannot be undone.

Yes. As of the 2026 tax year, the backdoor Roth (non-deductible traditional IRA contribution converted to Roth) and the mega backdoor Roth (after-tax 401(k) contributions converted in-plan) both remain available. The pro-rata rule still applies to traditional IRA balances, so coordination matters before any conversion.

The right strategy depends on what you hold. For ISOs, we model AMT exposure and stagger exercises to use the AMT credit. For NSOs and RSUs, we coordinate exercise and vesting timing with charitable giving, deferred comp, and state of residency. For founder shares, we layer QSBS planning, gifting strategies, and trust structures before any liquidity event.

A cash balance plan is a defined-benefit retirement plan that allows much higher annual contributions than a 401(k) — often $150,000–$300,000+ deductible per year for an owner over 50. They are ideal for high-income professionals (partners, doctors, specialists) and small profitable businesses where the owner can disproportionately benefit. We design and run the actuarial structure end-to-end.

Yes, with caveats. The original deferral benefit ended in 2026, but the 10-year basis step-up on appreciation in the QOF investment is still the headline benefit. They make sense when the underlying real estate or business deal is independently sound — never as a tax-only play.

Domicile changes can save 5%–13.3% on income depending on which state you leave. They make the most sense when paired with a liquidity event (large stock sale, business sale, RSU vest) and a real lifestyle move. The mistake we see most often is treating it as paperwork — successful domicile changes require facts and circumstances that survive a multi-year residency audit.

A CRT is an irrevocable trust that pays you (or another beneficiary) an income stream for life or a term of years, with the remainder going to charity. You contribute appreciated assets (often pre-IPO stock or concentrated positions), get an immediate charitable deduction for the present value of the remainder, and the trust sells the asset tax-free. It is often the right tool for diversifying a concentrated position with no taxable event.

AMT is most often triggered by exercising ISOs and holding the shares past year-end (the spread becomes a preference item), and to a lesser extent by large itemized deductions, certain private-activity bond interest, and depreciation timing differences. Our approach: model AMT exposure annually, exercise ISOs in tranches that fill — but do not exceed — your AMT corridor for the year, and recover the timing difference through the AMT credit carryforward in subsequent regular-tax years.

Often yes. We routinely amend returns within the 3-year statute when prior preparers missed elections, deductions, or credits. Common recoveries include unclaimed R&D credits, missed cost segregation studies, foreign tax credit re-sourcing, and entity-level state tax workarounds. The recovery typically pays for itself many times over.

Yes. We work with our clients' estate counsel on lifetime gifting, dynasty trusts, GRATs, IDGTs, valuation discounts, and the use of the lifetime exemption before scheduled sunsets. For most high-net-worth clients, the estate strategy and the income-tax strategy must be designed together — we coordinate both.

First, do not ignore it and do not respond on your own. Send us the notice — we triage every inbound within 24 hours and tell you exactly what it is, what the deadline is, and what's at stake. Most notices have hard response windows (typically 30, 60, or 90 days) where missing the date forfeits rights.

An audit (examination) is the IRS reviewing your return — it ends in either no change, an agreed change, or a proposed deficiency. If you disagree, you can take it to the IRS Office of Appeals, which is an independent review division. If you still disagree after Appeals, you can litigate in U.S. Tax Court (without paying first), or pay and sue in federal district court or the Court of Federal Claims.

Our median resolution is 11 months from notice to closure. Simple correspondence audits can resolve in 60–90 days. Complex examinations involving partnerships, equity events, or international issues can run 18–24+ months. We resolve 92% of our cases before tax court.

Often yes. The IRS allows penalty abatement under three primary doctrines: First-Time Abate (a clean compliance history typically removes one year of failure-to-file or failure-to-pay penalties), reasonable cause (documented circumstances outside your control), and statutory exceptions. We routinely secure full abatement on penalties that prior representatives accepted as final.

The Office of Appeals is the independent dispute resolution arm of the IRS. Appeals officers are not part of the examination team and are required to consider the hazards of litigation when settling — meaning they can compromise on amounts where examiners cannot. A well-built Appeals package often resolves in our client's favor without ever needing court.

CPAs, enrolled agents, and attorneys all have practice rights before the IRS. The right choice depends on the matter. For most examinations and appeals, a senior CPA with controversy experience is the most efficient representative. When the case involves potential criminal exposure or complex litigation, we coordinate directly with tax counsel.

Voluntary disclosure programs allow taxpayers with unreported income or unfiled returns to come into compliance with reduced penalties and significantly reduced criminal exposure. The two main programs are the IRS Voluntary Disclosure Practice (for willful conduct) and the Streamlined Filing Compliance Procedures (for non-willful conduct, primarily foreign accounts). Eligibility windows close once the IRS makes contact.

A levy can usually be released within days if you act quickly. The IRS must release a levy if it is causing economic hardship, if there is a pending installment agreement or offer in compromise, or if a procedural step (like Collection Due Process notice) was missed. We routinely secure same-week levy releases for new clients in active collection.

Yes. Multi-state controversy is a core part of our practice. We handle income tax, sales tax, residency / domicile audits, and nexus disputes in every state. State examinations often have shorter response windows and more aggressive collection posture than the IRS, so timing matters even more.

Reasonable cause is fact-specific, but recognized examples include serious illness, death in the family, natural disaster, reliance on incorrect professional advice, records destroyed in a casualty, and ignorance of the law in narrow circumstances. The standard is whether the taxpayer exercised ordinary business care and prudence and was nevertheless unable to comply.

Three primary paths. An installment agreement spreads the balance over up to 72 months (or longer for higher balances). An Offer in Compromise settles the debt for less than owed, typically based on collection potential. Currently Not Collectible status pauses collection if you have no current ability to pay. The right path depends on your financial picture — we model all three before recommending one.

Our controversy work is engagement-based, not hourly. Fees depend on the scope (single-issue correspondence vs. multi-year examination of complex returns), but most engagements are quoted up front so you know the cost before we start. For matters where penalties or back-tax exposure are large, the fee is typically a small fraction of the amount we save.

Embedded senior leadership without the cost of a full-time hire. Typical scope includes operating model design, KPI architecture, monthly close and dashboard cadence, rolling forecast, capital strategy, lender and investor relations, and transaction readiness. We work as part of your leadership team, not as an outside consultant.

The two most common moments are at $5M–$10M revenue when bookkeeping is no longer enough and you need real financial leadership, and at the inflection where you are preparing for a capital event (raise, recap, sale, ESOP). Bringing one in early is usually cheaper than untangling problems later.

A QoE is a financial diligence report that normalizes earnings to show a true, recurring picture of profitability — adjusting for one-time items, owner perks, accounting policy choices, and pro-forma changes. On a sale, the buyer's QoE drives the final purchase price. We prep clients pre-sale by building a sell-side QoE that anticipates and pre-resolves what buyers will challenge.

We start 18–36 months before the intended transaction. The sequence: clean financials and a defensible QoE, fix entity and tax structure for an efficient sale, model after-tax outcomes under multiple deal structures, coordinate with transaction counsel and investment bankers, and prep the data room. Founders who plan early routinely net 20–40% more after-tax than those who don't.

A bookkeeper records transactions. A controller closes the books and produces accurate financial statements. A CFO makes financial strategy decisions — capital, forecasting, transactions, investor relations. A tax advisor designs the tax architecture across the personal and entity stack. Most growing companies need all four functions; we cover the CFO and tax advisor roles and integrate with your bookkeeper / controller team.

Our advisory engagements typically run with founder-led businesses generating $5M–$250M in revenue. Below $5M, the engagement model is usually overkill. Above $250M, our role often becomes coordinator and tax architect alongside an in-house CFO and big-four diligence teams.

An ESOP is a qualified retirement plan that owns stock of the sponsoring company. Founders use ESOPs to transition ownership tax-efficiently. A sale of qualifying C-corp stock to the ESOP can defer capital gains under Section 1042 if the proceeds are reinvested in qualified replacement property (QRP) within the statutory window — the deferred gain remains in the QRP basis until disposition (and can be permanently avoided only via the step-up at death). The sponsoring company also receives deductions for ESOP contributions. Done well, an ESOP is one of the most tax-advantaged exit paths for a profitable, mid-market business.

It is the practice of taking money off the table in a tax-efficient, diversified, and strategically-timed way — without giving up control of the business. Tools include dividend recapitalizations, partial secondary sales, ESOP transactions, dividend policy changes, and structured loans against equity. We design and execute these alongside investment bankers and lenders.

Yes. We build operating models, capital structure models, and after-tax outcome models for both fundraising and exit scenarios. Our models are designed to survive third-party diligence and to drive negotiating leverage — not to be marketing decks.

Multi-year, retainer-based engagements with a defined monthly scope. We do not bill hourly because hourly billing rewards inefficiency and discourages clients from picking up the phone. The retainer is sized to your stage and scope, with as-needed project work (transaction advisory support, capital raises) priced separately and quoted up front.

All engagements are fee-based and quoted in writing before work begins — typically as a fixed engagement fee for project scopes, or a monthly retainer for ongoing planning and advisory. We do not bill hourly. You always know the cost before we start.

Yes. We offer a complimentary 30-minute introductory call with a senior practitioner. The goal of the call is to identify whether we are the right fit and where the most material opportunities are — not to sell you on an engagement.

Most new engagements begin within two weeks of an executed engagement letter. Active controversy matters with notice deadlines are triaged immediately and prioritized over the standard onboarding queue.

Yes — we sign client and counterparty NDAs as a matter of course. For engagements involving material non-public information (transactions, equity events, founder personal data), we have a standard mutual NDA we can provide, or we will execute yours.

Yes — and we prefer it. Many clients keep an existing relationship for compliance or wealth management while engaging us specifically for planning, controversy, or advisory. We coordinate directly with your team so nothing falls between seats.

A senior practitioner reviews the inbound, typically within one business day. If there is a clear fit, we schedule a 30-minute call. If we are not the right firm, we will tell you that — and where possible, point you toward someone who is.