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Corporate and advanced rules

The technical rules that catch closely held companies: accumulated earnings, built-in gains, related-party transactions, the economic substance doctrine, deferred compensation, and equity awards.

33 guides, each reviewed by a CPA licensed in the US and Canada.

Small Business & Bookkeeping

Accumulated Earnings Tax (IRC 531): When Retaining Too Much Profit in a C-Corp Costs You

The accumulated earnings tax under IRC 531 imposes a 20% penalty tax on C-Corporations that retain earnings beyond the reasonable needs of the business.

Sep 5, 2026
Small Business & Bookkeeping

Accumulated Earnings Tax: The C-Corp Penalty for Hoarding Profits (IRC 531)

C-Corporations that retain earnings beyond reasonable business needs face a 20% accumulated earnings tax on top of regular corporate tax.

Sep 5, 2026
Small Business & Bookkeeping

Accumulated Earnings Tax: The Penalty for Hoarding Profits in a C-Corporation (IRC 531)

The accumulated earnings tax under IRC 531 is a 20% penalty tax imposed on C-Corporations that accumulate earnings beyond the reasonable needs.

Sep 5, 2026
Small Business & Bookkeeping

Accumulated Earnings Tax: When Retaining Profits in a C-Corp Triggers a 20% Penalty

The accumulated earnings tax (AET) under IRC 531-537 is a 20% penalty tax on C-Corporations that accumulate earnings beyond the reasonable needs.

Sep 5, 2026
Small Business & Bookkeeping

Assignment of Income Doctrine: Why You Cannot Shift Business Income to a Lower-Bracket Family Member

The assignment of income doctrine prevents a taxpayer from avoiding taxes by directing income they have earned to another person or entity.

Sep 5, 2026
Small Business & Bookkeeping

Built-In Gains Tax (IRC 1374): Converting from C-Corp to S-Corp Without the Tax Trap

When a C-Corp converts to S-Corp status, any unrealized appreciation in the corporation's assets at the time of conversion is subject to the built-in.

Sep 5, 2026
Small Business & Bookkeeping

Built-In Gains Tax for S-Corps: How IRC 1374 Applies When Converting from C-Corp

When a C-Corporation elects S-Corporation status, the Built-In Gains (BIG) tax under IRC 1374 imposes a corporate-level tax on any appreciation.

Sep 5, 2026
Small Business & Bookkeeping

Economic Substance Doctrine: When the IRS Can Disallow a Legal Tax Strategy

The economic substance doctrine, codified under IRC 7701(o), allows the IRS to disallow tax benefits from a transaction that lacks economic substance.

Sep 5, 2026
Small Business & Bookkeeping

Economic Substance Doctrine: When the IRS Can Disregard Your Tax Strategy as a Sham

The economic substance doctrine, codified in IRC 7701(o) by the Health Care and Education Reconciliation Act of 2010. The two-prong test (IRC 7701(o)): |.

Sep 5, 2026
Small Business & Bookkeeping

Economic Substance Doctrine: When the IRS Disallows Legitimate-Looking Tax Strategies

The economic substance doctrine (codified in IRC 7701(o)) requires that a transaction have meaningful economic effects apart from tax benefits.

Sep 5, 2026
Small Business & Bookkeeping

Employee Stock Options: ISO vs. NSO Tax Treatment and Exercise Strategies

ISOs and NSOs have different tax timing and rates. NSOs are taxed as ordinary income at exercise; ISOs get capital gains treatment if holding periods.

Sep 5, 2026
Small Business & Bookkeeping

Foreign-Owned US Businesses: Tax Rules for ECI, FIRPTA, Branch Profits Tax, and Treaty Benefits

When a foreign person or entity owns a US business or invests in US real property, the US tax rules are significantly more complex than domestic taxation.

Sep 5, 2026
Small Business & Bookkeeping

Golden Parachute Rules (IRC 280G): Tax Penalties on Excess Change-in-Control Payments

Under IRC 280G, when a corporation undergoes a change in ownership or control and makes 'excess parachute payments' to certain officers, shareholders.

Sep 5, 2026
Small Business & Bookkeeping

International Tax for US Business Owners: GILTI, Subpart F, PFIC, and Foreign Tax Credits

US citizens and residents are taxed on worldwide income, and US business owners with foreign operations face additional layers of complexity.

Sep 5, 2026
Small Business & Bookkeeping

International Tax for US Business Owners: Subpart F Income, GILTI, FDII, and Controlled Foreign Corporation Rules

US persons who own or control foreign corporations face a complex set of anti-deferral rules designed to prevent the indefinite sheltering of income.

Sep 5, 2026
Small Business & Bookkeeping

IRC 1244 Small Business Stock: Convert Capital Losses to Ordinary Deductions Up to $100,000

IRC 1244 lets founders deduct losses on qualifying small business stock as ordinary losses, not capital losses. The annual limit is $50,000 ($100.

Sep 5, 2026
Small Business & Bookkeeping

IRC 409A Deferred Compensation: Rules, Penalties, and Compliance for Business Owners

IRC 409A governs nonqualified deferred compensation (NQDC) plans, imposing strict rules on when compensation can be deferred, when it must be paid.

Sep 5, 2026
Small Business & Bookkeeping

IRC 409A Deferred Compensation: Rules, Penalties, and Planning for Business Owners

IRC 409A governs all nonqualified deferred compensation arrangements and imposes severe penalties for noncompliance. Covers key rules, filing.

Sep 5, 2026
Small Business & Bookkeeping

IRC 83(b) Election for Restricted Stock: How Founders and Startup Employees Lock In Low Tax Rates

The IRC 83(b) election is one of the most valuable and most frequently missed tax elections available to startup founders, early employees.

Sep 5, 2026
Small Business & Bookkeeping

IRC 83(b) Elections: How to Save Thousands on Restricted Stock and LLC Interests

An IRC 83(b) election allows a service provider who receives restricted stock or LLC/partnership interests subject to vesting to pay income tax.

Sep 5, 2026
Small Business & Bookkeeping

Related Party Transactions: IRC 267 Loss Disallowance, Constructive Ownership, and Controlled Group Rules

Transactions between related parties receive special scrutiny under the tax code because the parties can manipulate prices, timing.

Sep 5, 2026
Small Business & Bookkeeping

Related-Party Transaction Rules: Tax Implications of Business Deals with Family and Partners

IRC 267 applies heightened scrutiny to transactions between related parties. Family members, controlled entities, and trusts face loss disallowance rules.

Sep 5, 2026
Small Business & Bookkeeping

S-Corp Accumulated Adjustments Account (AAA) Explained

The AAA tracks the S-Corp's cumulative net income minus distributions since the S election. Distributions are tax-free to the extent of AAA.

Sep 5, 2026
Small Business & Bookkeeping

Section 1244 Small Business Stock: Converting a Business Loss into an Ordinary Tax Deduction

IRC Section 1244 allows founders to deduct up to $50,000 ($100,000 MFJ) of losses on qualifying small business stock as ordinary losses instead of capital.

Sep 5, 2026
Small Business & Bookkeeping

Section 1244 Stock: Converting Capital Losses to Ordinary Losses on Small Business Stock

Section 1244 of the IRC allows individual shareholders of qualifying small business corporations to treat losses on the sale or worthlessness.

Sep 5, 2026
Small Business & Bookkeeping

Section 1244 Stock: How to Deduct Small Business Stock Losses as Ordinary (Not Capital) Losses

Section 1244 of the Internal Revenue Code allows founders and original investors in small businesses to deduct stock losses as ordinary losses (up.

Sep 5, 2026
Small Business & Bookkeeping

Section 1244 Stock: How to Turn a Business Failure Into an Ordinary Loss Deduction

Under IRC 1244, losses on the sale or worthlessness of qualifying small business stock receive ordinary loss treatment (up to $50,000 single.

Sep 5, 2026
Small Business & Bookkeeping

Section 409A Deferred Compensation: Rules, Penalties, and Compliance for Small Businesses

IRC 409A governs nonqualified deferred compensation arrangements. Violations trigger a 20% penalty tax plus interest on the deferred amount.

Sep 5, 2026
Small Business & Bookkeeping

Stock Options and Restricted Stock Awards: Tax Treatment of Equity Compensation for Business Owners and Employees

Equity compensation is one of the most complex areas of individual and business taxation because the tax consequences depend on the type of award.

Sep 5, 2026
Small Business & Bookkeeping

Tax Implications of Hiring International Workers: Foreign Contractors, EOR, and Permanent Establishment Risk

When a US business hires workers outside the United States, the tax and compliance obligations depend on the worker's classification (employee vs.

Sep 5, 2026
Small Business & Bookkeeping

Tax Implications of Joint Ventures and Strategic Alliances: Partnership vs. Contractual Arrangements, Tax Elections, and Profit Sharing

Joint ventures between two or more businesses create different tax consequences depending on whether the arrangement is structured as a partnership.

Sep 5, 2026
Small Business & Bookkeeping

Tax-Free Reorganizations Under IRC 368: How Businesses Restructure Without Triggering Gains

IRC 368 defines seven types of tax-free corporate reorganizations (A through G) that allow businesses to merge, consolidate, acquire.

Sep 5, 2026
Small Business & Bookkeeping

Tax-Free Reorganizations: IRC 368 Rules for Mergers, Acquisitions, and Corporate Restructurings

IRC 368 provides seven types of tax-free corporate reorganizations (Types A through G) that allow businesses to merge, consolidate, acquire.

Sep 5, 2026

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