Why Most Tax Resolutions Fall Short
The standard approach to an IRS problem is to resolve it and move on. Pay what you owe, enter an installment agreement, accept an offer in compromise, and hope it doesn't happen again. That approach solves the symptom. It almost never solves the underlying problem.
The MacPherson Group has observed a consistent pattern across decades of client work: the majority of clients with significant IRS problems had never been shown how to legally reduce their tax burden. They had no pension plan, no entity structure that separated their personal and business exposure, no plan for passing their assets to the next generation. They overpaid taxes for years — then got into trouble when they tried to stop.
An IRS investigation or tax debt is, in a strange way, an opportunity. It forces a comprehensive financial review that most people never voluntarily undertake. That review almost always reveals legal strategies that, properly implemented, produce more in tax savings than the cost of defense. The goal of this practice area is not merely to resolve your IRS matter — it is to ensure you emerge from it in better financial health than you entered.
- IRS debt, audit, or investigation underway
- Business structure not optimized for tax efficiency
- No formal pension or retirement vehicle
- Unsecured debt (credit cards, personal loans)
- No plan for generational wealth transfer
- Paying full marginal tax rate on business income
- IRS matter resolved — for as little as possible
- Business restructured for tax efficiency
- Pension plan sheltering Varies by plan, age & income
- Unsecured debt negotiated — often at significant reductions
- Succession plan protecting family wealth
- Legally paying a fraction of prior tax liability
From Defense to Offense — The Strategies
These are not aggressive tax positions. They are legal, well-established strategies that the tax code was designed to allow. Most of our clients simply never had an advisor who knew to recommend them.
Business Restructuring
The wrong entity structure costs real money. A sole proprietor subject to 15.3% self-employment tax on every dollar of profit is a common and expensive mistake. Proper entity selection — S-Corp, C-Corp, LLC with appropriate elections — combined with a defensible compensation structure can eliminate tens of thousands of dollars in annual tax liability, legally, while simultaneously making the business more resistant to IRS examination.
Pension Plan Strategy
A properly structured defined-benefit pension plan can legally shelter $100,000 to $300,000 or more per year from federal income tax for a self-employed individual or small business owner. Contributions are tax-deductible. Growth is tax-deferred. Done correctly, a pension plan simultaneously reduces the taxable income the IRS can reach, assists in resolving a current IRS dispute by demonstrating good-faith compliance, and creates a generational inheritance. The MacPherson Group works with industry-leading pension plan administrators and financial advisors to structure compliant, custom-tailored plans.
Captive Insurance
A captive insurance company is a licensed insurance subsidiary that underwrites risks specific to the parent business. Premiums paid to the captive are deductible to the operating company — reducing taxable income — while reserves accumulate and can be distributed over time. Under IRC § 831(b), smaller captives (premiums under $2.65 million annually) receive favorable tax treatment. The IRS has aggressively pursued abusive captive arrangements, but properly structured captives remain legitimate and powerful. The MacPherson Group evaluates whether a captive is appropriate and legally sound for each client's specific situation.
Credit Card & Unsecured Debt Settlement
Most tax clients also carry significant unsecured debt. The MacPherson Group regularly negotiates directly with creditors to settle credit card debt, personal loans, and other unsecured obligations outside of bankruptcy — often achieving significant reductions — sometimes 40 to 60 cents on the dollar, depending on the creditor, the balance, and the client's financial situation. Resolving unsecured debt alongside the IRS matter produces a genuine financial reset, not merely a tax resolution. We also work with strategic partners to assist clients in rebuilding credit and obtaining liquidity once the resolution is complete.
Intergenerational Business Transfer
Federal estate, gift, and income tax intersect in complex and costly ways during any business succession. Without planning, the business may need to be sold — often at a distressed price — simply to pay an estate tax bill. The MacPherson Group has assisted numerous families in structuring transfers that minimize tax exposure, preserve the business as a going concern, and create a lasting inheritance. As a multigenerational family firm, this work reflects our own values. We have seen what it costs when succession planning is absent — and what it looks like when it is done right.
International Tax Strategy & FBAR Compliance
Nathan MacPherson has worked across 25 countries, lived and worked in four, speaks four languages, and is licensed on two continents — including as a Solicitor of the Senior Courts of England and Wales, with experience at Freshfields Bruckhaus Deringer in Frankfurt and London. Foreign accounts, offshore trusts, international business structures, FBAR, FATCA, and treaty-based planning are not exotic edge cases for The MacPherson Group — they are the work Nathan has done throughout his career. International clients receive counsel from someone who has been inside these structures at the highest level, not someone reading about them for the first time.
Cryptocurrency Tax Planning & Defense
The IRS treats cryptocurrency as property. Every transaction — purchase, sale, exchange, payment, or mining reward — is a taxable event. The MacPherson Group has represented cryptocurrency exchanges, miners, and individual investors in IRS audits, voluntary disclosure situations, and matters triggered by IRS Letters 6173, 6174, and 6174-A. Beyond defense, we help clients structure their cryptocurrency activity to minimize taxable events, utilize available loss harvesting, and document their basis in a way that holds up to IRS scrutiny. If you hold cryptocurrency and have not been fully compliant, contact us before the IRS contacts you.
The Network — Legal, Financial & Planning Advisors
The MacPherson Group is a law firm, not a financial planning firm. We are not licensed to provide investment advice. But we have spent decades building a network of world-class advisors — pension plan administrators, financial planners, business coaches, credit specialists, and others — who integrate with the legal work. When a client's situation calls for expertise beyond tax law, we coordinate the full team. One of our close advisors is recognized as the world's leading priority strategist, whose counsel has helped businesses of every size better carry out their mission. Our legal fees, properly understood, are not an expense — they are an investment with measurable return.
What This Approach Produces
Prior results do not guarantee similar outcomes. Each case depends on its specific facts.
2.5¢"I really did not believe we would have a good outcome. We settled for 2.5% of what the IRS was claiming. I kept 100% of my home equity."
— Church Deacon, resolved through negotiated settlement with comprehensive restructuring
IRS debt settled for pennies on the dollar — and unsecured debt negotiated simultaneously
Pension plan established during resolution — reducing ongoing tax liability before the ink dried
Business restructured so the conditions that created the IRS problem cannot recur
Legal fees structured so that the tax savings in year one exceed the cost of defense
Complex Matters We Handle
The following is a representative list of the specialized areas in which The MacPherson Group has substantial experience. Nathan MacPherson's background — international legal practice, Oxford-level academic training, work at one of the world's largest law firms — means these are not peripheral capabilities added for marketing purposes. They are the work.
International & Offshore
- FBAR — FinCEN Form 114 compliance and penalties
- FATCA — Form 8938 and foreign financial asset reporting
- Offshore Voluntary Disclosure (OVDP and Streamlined)
- Foreign trusts — Forms 3520 and 3520-A
- Foreign corporations — Form 5471
- Foreign partnerships — Form 8865
- PFIC / Form 8621 (passive foreign investment companies)
- Transfer pricing issues
- Tax and information sharing treaties
- International business companies (IBC)
- Letters rogatory and issues of comity
- Jurisdiction of U.S. courts over foreign entities
Business & Planning Structures
- Captive insurance companies — IRC § 831(b)
- Defined-benefit pension plans
- Deferred compensation structures
- Employee leasing arrangements
- Bahamian and foreign insurance companies
- "Offshore triple trust" structures
- VEBA (Voluntary Employees' Beneficiary Association)
- Tax shelters — Son of BOSS and similar
- Intergenerational business transfer planning
- Business succession and estate coordination
- Entity restructuring for tax efficiency
- Strategic alliances and joint venture tax issues
Emerging & Complex
- Cryptocurrency — Bitcoin, Ethereum, altcoins
- Cryptocurrency mining income
- NFT tax treatment
- IRS Letters 6173, 6174, 6174-A response
- Credit card and unsecured debt settlement
- Credit rebuilding and liquidity planning
- Abusive tax shelter defense
- Infinite banking / hobby loss challenges
- Embezzlement income issues
- Jeopardy assessment defense
- Alter ego / nominee / fraudulent conveyance
- Multi-jurisdictional state tax issues
Nathan MacPherson: Turning Your IRS Problem Into an Opportunity
Watch Nathan explain how The MacPherson Group approaches comprehensive tax defense differently — not just resolving the IRS matter, but rebuilding the financial foundation so the crisis cannot recur and the client emerges in a stronger position than before.
Frequently Asked Questions
These are the questions we hear most from clients who arrive with a tax problem and leave with a financial strategy.
How can an IRS problem actually become a financial opportunity?
Most clients who come to The MacPherson Group with an IRS problem have a larger systemic issue underneath it: a business structure that leaks money, no formal retirement planning, excessive unsecured debt, or years of missed deductions. Resolving the IRS matter forces a comprehensive financial review — and that review almost always reveals legal tax-saving strategies that more than offset the cost of defense. The MacPherson Group does not just resolve the crisis; it rebuilds the financial foundation so the crisis cannot recur.
What is a pension plan strategy in the context of tax defense?
A properly structured defined-benefit or defined-contribution pension plan can legally remove significant income from taxable exposure — sometimes $100,000 to $300,000 or more per year for qualifying self-employed individuals and small business owners, depending on age, income, and plan design. The MacPherson Group works with industry-leading pension plan administrators to structure compliant plans that simultaneously reduce current-year tax liability and assist in resolving IRS disputes by demonstrating ability to pay. These plans create generational wealth while reducing the tax base the IRS can reach.
Can The MacPherson Group help restructure my business while resolving my IRS matter?
Yes. Most IRS civil problems originate in a business structure that was never designed for tax efficiency — a sole proprietor who should be an S-Corp, a business with informal bookkeeping that cannot substantiate deductions, or a growing company that outgrew its original entity structure. The MacPherson Group reviews the entire business system, not just the tax dispute, and recommends restructuring that reduces future tax liability, improves compliance, and makes the overall financial operation more defensible.
What is a captive insurance company and how does it reduce taxes?
A captive insurance company is a legitimate tax planning structure in which a business owner creates a licensed insurance subsidiary to underwrite risks specific to their business. Premiums paid to the captive are deductible to the operating company, reducing taxable income. The captive accumulates reserves that can be invested and eventually distributed. The IRS has scrutinized abusive captive arrangements, but properly structured captives under IRC § 831(b) remain a legitimate and powerful tax strategy. The MacPherson Group evaluates whether a captive is appropriate and legal for your specific situation.
Can The MacPherson Group help settle my credit card debt alongside my IRS matter?
Yes. Many tax clients also carry significant unsecured debt — credit cards, lines of credit, personal loans — that compounds their financial distress. The MacPherson Group regularly negotiates with creditors to settle unsecured debt outside of bankruptcy, often achieving significant reductions — results vary by creditor, balance, and individual circumstances. Resolving both the tax matter and the unsecured debt simultaneously produces a genuine fresh start rather than just a tax resolution. We also work with strategic partners to assist clients in rebuilding credit once the resolution is complete.
What is an intergenerational business transfer and how does tax law affect it?
An intergenerational business transfer involves the planned transition of a business — and its wealth — from one generation to the next. Federal estate tax, gift tax, and income tax all intersect in complex ways during a business succession. Improper planning can result in the business being sold to pay an estate tax bill. The MacPherson Group has assisted numerous families in structuring transfers that minimize tax exposure, preserve the business as a going concern, and create a lasting inheritance. As a multigenerational family firm ourselves, this work is personal.
Does The MacPherson Group handle cryptocurrency tax matters?
Yes. The IRS treats cryptocurrency as property, meaning every transaction is a taxable event. Mining income is reportable as ordinary income. The MacPherson Group has represented cryptocurrency exchanges, miners, and individual investors in IRS compliance matters, voluntary disclosure situations, and audits. If you received IRS Letter 6173, 6174, or 6174-A regarding cryptocurrency, contact us immediately. Beyond defense, we help clients structure their activity to minimize taxable events going forward.
What is FBAR and what are the penalties for non-filing?
FBAR (FinCEN Form 114) is required of any U.S. person with financial interest in, or signature authority over, foreign financial accounts with an aggregate value exceeding $10,000. Civil penalties for non-willful failure are up to $16,536 per violation (2025–2026 inflation-adjusted; statutory cap $10,000, adjusted annually for inflation). Willful failure can result in civil penalties up to the greater of $165,353 or 50% of account value per violation — per year (2025–2026 inflation-adjusted). Criminal penalties include imprisonment. The MacPherson Group has extensive experience with FBAR compliance, offshore voluntary disclosure, and the IRS Streamlined Filing Compliance Procedures, with Nathan's firsthand international legal background giving him insight no purely domestic attorney can match.