#business-structure
Business Structure
Choose and optimize your business entity for tax and legal advantages
Personal Guarantees: How They Override Your LLC—and How to Negotiate Them
59% of small businesses with debt sign a personal guarantee, and it overrides your LLC's limited liability. This guide explains unlimited vs. limited guarantees, bad-boy carve-outs, burn-off provisions, SBA's 20% rule, and how to negotiate or get released.
The Self-Rental Rule Under Section 469: How the Grouping Election Defuses the Passive Loss Trap
Section 469's self-rental rule recharacterizes rent from your own building as active income while losses stay passive — a one-way street that traps small business owners. A timely grouping election under Reg. 1.469-4 defuses it; missing the first-return filing window usually means living with the asymmetry for good.
The Self-Rental Rule: Why Your Building Rents Are Nonpassive but Your Losses Stay Passive
Reg. 1.469-2(f)(6) recharacterizes net rental income from property you rent to your own active business as nonpassive while leaving rental losses passive. This guide explains the asymmetry, walks through a dentist example with a $200,000 cost segregation deduction, and shows how the Reg. 1.469-4 grouping election can collapse the rule.
The F Reorganization: How S Corporations Restructure Tax-Free Before a Sale
An F reorganization under IRC Section 368(a)(1)(F) lets an S corporation restructure tax-free into a holding-company/QSub form so a buyer gets an asset basis step-up at any ownership percentage and sellers can defer tax on rollover equity.
Setting Up Owner's Equity Accounts: Tracking Contributions, Draws, and Retained Earnings the Right Way
Owner's equity is Assets minus Liabilities — the running total of contributions, draws, profit, and losses. This guide structures equity accounts for sole proprietors, partnerships, and LLCs, explains why draws are not expenses, and shows the year-end closing entries that keep a balance sheet in balance.
The Section 1375 Sting Tax: How Former C Corps Pay 21% on Passive Income and Lose Their S Election After Three Years
Section 1375 imposes a flat 21% sting tax on S corporations that carry C-corp earnings and profits when passive investment income exceeds 25% of gross receipts, and three consecutive years over that threshold terminates the S election automatically. This guide walks through the excess net passive income formula, the three-year cliff under Section 1362(d)(3), and three planning moves to defuse exposure before year-end.
The Section 1375 Sting Tax: How S Corporations Trigger the 21% Passive Income Tax and a Three-Year Termination Cliff
The Section 1375 sting tax hits an S corporation with a 21% corporate-level tax when it has C-corporation E&P and passive investment income above 25% of gross receipts; three consecutive years of that combination terminates the S election. This guide shows who is exposed, how excess net passive income is calculated, and how to defuse the trap.
Section 414 Controlled Group and Affiliated Service Group Rules: How Multiple Businesses Can Sabotage Your 401(k)
Section 414(b), (c), and (m) treat related businesses as one employer for retirement-plan testing. This guide explains controlled-group and affiliated-service-group rules, the spousal and minor-child attribution traps, and the steps multi-business owners should take before opening a 401(k).
Section 707 Disguised Sale Rules: When a Partnership Contribution Becomes a Taxable Sale
A disguised sale under Section 707(a)(2)(B) collapses a partnership contribution and a related cash distribution into a taxable sale. Transfers within two years are presumed a sale; the deemed-sale fraction equals consideration received divided by property FMV.
Section 7874 Anti-Inversion Rules: 60%/80% Ownership Tests and the Substantial Business Activities Safe Harbor
Section 7874 imposes a 10-year inversion-gain floor when former U.S. shareholders own 60-80% of a new foreign parent and reclassifies the parent as a domestic corporation at 80%. The only escape is the substantial business activities safe harbor, which requires clearing a 25% bright-line threshold on employees, tangible assets, and gross income in the foreign country.
Section 7874 Anti-Inversion Rules: Why a Foreign Parent Does Not Always Mean a Foreign Tax Bill
Section 7874 treats a foreign parent as a U.S. corporation when former U.S. owners hold 80% or more, and penalizes inversion gain for 10 years at 60-80%. The substantial business activities safe harbor requires 25% of employees, assets, and income in the foreign country.
Subchapter T Patronage Dividends Explained: How Co-ops Avoid Double Tax, Issue Qualified and Nonqualified Written Notices of Allocation, and Report Member Distributions on Form 1099-PATR
How Subchapter T lets U.S. cooperatives deduct patronage dividends and avoid corporate double tax — covering the 20% cash floor for qualified written notices of allocation, the post-2017 shift toward nonqualified treatment, per-unit retains, Form 1099-PATR box-by-box reporting, Section 199A(g) for specified ag co-ops, and the recordkeeping that turns a deduction into a defensible one.