conceptfinancetaxescompanystartuphackcatalogUpdated 2026-07-01

Company Tax Hacks

60 entity-level strategies — startup QSBS, R&D credits, payroll, depreciation, multi-state, and memed shams. Part of Tax Hacks Catalog. Relevant to Dedalus Labs-scale companies. Not tax advice.

Verdict key: Standard · Strategic · Aggressive · Folklore

Entity structure & startup (1–12)

  1. Delaware C-corp (VC path) — Standard startup entity for equity, QSBS, and institutional investment. Standard Source: compiled from startup formation practice, 2026-06-13

  2. QSBS §1202 exclusion — Exclude up to $10M+ gain (or 10× basis) on qualified small business stock held 5+ years if eligibility met at issuance. Strategic Source: IRC §1202, 2026-06-13

  3. Section 83(b) election — Tax on RSA/early exercise at grant FMV; upside grows as capital gain. 30-day deadline. Strategic Source: IRC §83(b), 2026-06-13

  4. R&D tax credit — Credit for qualified research expenses; startups can offset payroll tax (up to $500k/year election). Strategic Source: IRC §41, 2026-06-13

  5. Startup costs §195 — Expense first $5k immediately; amortize remainder over 180 months. Standard Source: IRC §195, 2026-06-13

  6. S-corp election (LLC) — Avoid double tax; pass-through to owners; W-2 reasonable salary required. Strategic Source: IRS, 2026-06-13

  7. Check-the-box election — LLC chooses corporate vs partnership tax treatment. Standard Source: IRS Reg §301.7701-3, 2026-06-13

  8. Qualified small business stock stacking — Multiple founders/investors each with separate §1202 cap on eligible stock. Strategic Source: IRC §1202, 2026-06-13

  9. 409A valuation compliance — Cheap or missing 409A on options → penalty tax on employees; not a hack, a guardrail. Standard Source: IRC §409A, 2026-06-13

  10. ISO vs NSO planning — ISOs: no ordinary income at exercise if holding periods met; AMT trap. NSOs: deductible to company at exercise. Strategic Source: IRC §422, 2026-06-13

  11. ESPP discount — Employee stock purchase plans; discount often not taxed until sale if qualifying disposition. Standard Source: IRC §423, 2026-06-13

  12. Phantom / profits interests (LLC) — Profits interest at zero FMV if structured correctly; capital gains on exit. Aggressive Source: Rev Proc 93-27, 2026-06-13

Payroll, benefits & compensation (13–22)

  1. Accountable plan — Reimburse documented T&E without treating payments as wages (no FICA). Standard Source: IRS Pub 463, 2026-06-13

  2. QSEHRA / ICHRA — Reimburse individual health premiums tax-efficiently vs group plan. Strategic Source: IRS, 2026-06-13

  3. Section 127 tuition assistance — Up to $5,250/year excludable from employee wages. Standard Source: IRC §127, 2026-06-13

  4. Group term life ($50k exclusion) — First $50k of employer-paid life insurance excludable. Standard Source: IRC §79, 2026-06-13

  5. Dependent care FSA — Pre-tax dependent care up to annual limit. Standard Source: IRS, 2026-06-13

  6. Augusta Rule (corp rents owner home) — Company pays owner fair rent for ≤14 days of meetings; rent tax-free to owner, deductible to corp if ordinary/necessary. Strategic Source: IRC §280A(g), 2026-06-13

  7. Hire family on payroll — Legitimate services at market wages; avoid kiddie tax / unreasonable comp issues. Strategic Source: IRS, 2026-06-13

  8. Contractor vs employee (1099) — Misclassification penalties dwarf tax savings; use ABC test / IRS factors honestly. Standard Source: IRS, 2026-06-13

  9. Stock option early exercise + 83(b) — Startup combo for long-term capital gains treatment. Strategic Source: compiled from startup equity practice, 2026-06-13

  10. Deferred compensation §409A plans — Non-qualified plans for execs; strict documentation. Aggressive Source: IRC §409A, 2026-06-13

Depreciation & capital (23–32)

  1. Bonus depreciation §168(k) — Immediate expensing percentage on qualified property (phase-down schedule). Strategic Source: IRC §168(k), 2026-06-13

  2. Section 179 expensing — Expense equipment/software up to annual cap in year placed in service. Standard Source: IRC §179, 2026-06-13

  3. Cost segregation (commercial RE) — Reclassify building components to shorter MACRS lives. Aggressive Source: IRS, 2026-06-13

  4. Heavy vehicle §179 — SUVs/trucks over 6,000 lbs GVWR subject to higher caps; personal use reduces deduction. Strategic Source: IRC §179, 2026-06-13

  5. Software capitalization vs expense — Internal-use software may capitalize; R&D software often expensed under §174 (rules in flux). Strategic Source: IRC §174, 2026-06-13

  6. LIFO inventory — Last-in-first-out matches rising costs; not available to all entities. Strategic Source: IRC §472, 2026-06-13

  7. §197 amortization — Amortize acquired goodwill and intangibles over 15 years. Standard Source: IRC §197, 2026-06-13

  8. Repairs vs capitalization — Expense routine maintenance; capitalize improvements (tangible property regs). Standard Source: IRS Reg §1.263(a), 2026-06-13

  9. Research & experimental §174 — US-based R&E amortization required post-TCJA (5-year domestic); planning around capitalization. Strategic Source: IRC §174, 2026-06-13

  10. Energy-efficient commercial building deduction §179D — Deduction for qualifying efficiency improvements. Strategic Source: IRC §179D, 2026-06-13

Losses, timing & accounting (33–42)

  1. NOL carryforward — Net operating losses offset future income (80% taxable income limit post-TCJA). Standard Source: IRC §172, 2026-06-13

  2. Cash vs accrual method — Small business may use cash method under gross receipts test. Standard Source: IRC §448, 2026-06-13

  3. Fiscal year election — Non-calendar year-end for seasonality (S-corp restrictions). Strategic Source: IRS, 2026-06-13

  4. Accelerate deductions / defer income — Prepay expenses, delay billing in high-tax years (accrual rules apply). Strategic Source: compiled from tax timing practice, 2026-06-13

  5. Related-party AFR loans — Loan to/from owner at IRS Applicable Federal Rate to avoid imputed income. Strategic Source: IRC §7872, 2026-06-13

  6. Management fee between entities — Parent charges subsidiary for services; transfer pricing must be arm's length. Aggressive Source: IRC §482, 2026-06-13

  7. Accumulated earnings tax planning — Retain earnings with documented business reasons vs penalty on excess accumulation (C-corp). Strategic Source: IRC §531, 2026-06-13

  8. Buyback vs dividend — Return cash via §302 redemption (capital gain treatment possible) vs taxable dividend. Strategic Source: IRC §302, 2026-06-13

  9. Pass-through entity tax (PTE) — State-level entity tax on S-corp/partnership with owner credit — SALT workaround. Strategic Source: state law + IRS, 2026-06-13

  10. QBI at entity level — W-2 wages and UBIA property affect §199A deduction for pass-through owners. Strategic Source: IRC §199A, 2026-06-13

Multi-state & international (43–50)

  1. State nexus minimization — Remote employees and sales create nexus; don't "hack" your way out of economic nexus post-Wayfair. Standard Source: South Dakota v Wayfair, 2018

  2. Delaware incorporation (not a tax haven) — Franchise tax due; no magical income shift for operating company. Folklore Source: Delaware Division of Corporations, 2026-06-13

  3. Wyoming LLC privacy meme — Asset protection ≠ tax elimination; operating income still taxed where earned. Folklore Source: compiled from entity-formation memes, 2026-06-13

  4. FDII deduction — Domestic corps deduct portion of foreign-derived intangible income (37.5% effective rate target). Aggressive Source: IRC §250, 2026-06-13

  5. GILTI planning — US shareholders of controlled foreign corps pay GILTI; complex international structure territory. Aggressive Source: IRC §951A, 2026-06-13

  6. Transfer pricing documentation — Intercompany prices must match arm's length; penalties for failure. Standard Source: IRC §482, 2026-06-13

  7. IP holding company (state) — License IP from operating co; must have substance and arm's-length royalty. Aggressive Source: state tax authority challenges, 2026-06-13

  8. Estonia e-Residency / Dubai free zone meme — Residency and PE rules follow where work and control actually happen. Folklore Source: compiled from nomad tax discourse, 2026-06-13

Credits, M&A & enforcement traps (51–60)

  1. Work Opportunity Tax Credit — Credit for hiring from targeted groups; certification required. Standard Source: IRC §51, 2026-06-13

  2. Employee Retention Credit (ERC) — COVID-era credit; widespread fraud mills; strict eligibility windows closed. Folklore Source: IRS ERC enforcement, 2026-06-13

  3. Captive insurance §831(b) — Micro-captive premiums deducted; IRS listed abusive transaction. Aggressive Source: IRS Notice 2016-66, 2026-06-13

  4. Conservation easement syndication (corp sponsor) — Same IRS enforcement priority as individual syndicated easements. Aggressive Source: IRS, 2026-06-13

  5. §338(h)(10) election — Treat stock purchase as asset purchase for tax purposes in S-corp acquisitions. Strategic Source: IRC §338(h)(10), 2026-06-13

  6. Tax-free reorganization (A/B/C) — M&A structure to defer gain in qualifying corporate reorganizations. Strategic Source: IRC §368, 2026-06-13

  7. R&D credit mills — Third parties inflate QREs; company liable for bad claims. Folklore Source: IRS R&D audit guidance, 2026-06-13

  8. Shell company income shifting — Invoice through zero-substance entity in no-tax state; sham transaction risk. Folklore Source: IRS economic substance doctrine, 2026-06-13

  9. Deduct entire team dinner as "marketing" — Meals generally 50% limited; entertainment nondeductible. Folklore Source: IRC §274, 2026-06-13

  10. Stripe Atlas / Mercury as tax strategy — Formation and banking tools, not deductions. Real stack: C-corp + QSBS + R&D credit + accountable plan + 83(b). Standard Source: compiled from Personal Finance founder stack + User, 2026-06-13

Concept Position

Field Value
Concept family Product, business, distribution, and positioning
Concept owned 60 entity-level strategies — startup QSBS, R&D credits, payroll, depreciation, multi-state, and memed shams. Part of tax-hacks. Relevant to...
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Timeline

  • 2026-07-01 | Concepts category refresh added this page to the Product, business, distribution, and positioning family, linked it to Concept System Map, and kept it standalone because it owns this reusable mental model: 60 entity-level strategies — startup QSBS, R&D credits, payroll, depreciation, multi-state, and memed shams. Part of tax-hacks. Relevant to... Source: User request, 2026-07-01
  • 2026-06-13 | Kevin requested 60 company tax hacks. Catalog created as part of Tax Hacks Catalog; cross-linked to Dedalus Labs for startup context. Source: User, 2026-06-13

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