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The Tax Playbook - Grampsaid
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The Tax Playbook

Volume II

The W-2 employee and the business owner who knows the code pay completely different effective rates on the same income. The strategies in this playbook are in the tax code. The deduction machine. The S-corp salary arbitrage. The real estate tax game. The retirement account arsenal. The international layer. This is what the code rewards when you structure for it.

77 Pages
10 Parts
S-Corp to PPLI
Full Structure Map
Augusta Rule
to Act 60
Audit Defense
Included
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The Tax Playbook - Grampsaid
Grampsaid
Tax Playbook
Volume II
Gramps Said
$47
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Who This Is For
This playbook is for you if
  • ✓Business owners and self-employed operators who want to understand what the tax code actually rewards
  • ✓Real estate investors who want to use depreciation, cost segregation and REPS status correctly
  • ✓High earners looking at retirement account structures beyond the standard 401k
  • ✓Anyone who wants to understand the full picture before paying a CPA $500 an hour to explain it
This is not for you if
  • ✗Anyone looking for help with basic tax filing
  • ✗People unwilling to restructure how their income is received
What's Inside

Not theory.
The actual mechanisms.

Part 1
The Game
How tax actually works. Why most people overpay. The taxpayer hierarchy -- W-2 employee, self-employed, business owner, investor -- and how each tier is taxed differently. The three levers: income type, timing, and structure.
Part 2
The Business Structure Playbook
Sole proprietorship as the worst structure. S-corporation salary arbitrage -- save $33,660/year from one decision. C-corporation retained earnings game at 21%. The LLC menu. Which structure wins at which income level.
Part 3
The Deduction Machine
The full business deduction stack. The Augusta Rule -- Section 280A(g), 14 days, $28,000 tax-free. Home office done right. Vehicle strategy and Section 179. The accountable plan. Hiring your kids at $14,600/year per child. Health insurance through the business.
Part 4
The Real Estate Tax Game
Why the tax code was written for real estate investors. Depreciation as the non-cash deduction. Cost segregation -- $44,400 in additional year-one deductions from a $7,000 study. Real estate professional status as the offset weapon. The 1031 exchange. Opportunity zones. Short-term rental loophole.
Part 5
The Investment Tax Playbook
Capital gains vs ordinary income and the 17-point rate difference. The holding period game. Tax loss harvesting. QSBS Section 1202 -- 0% capital gains on up to $10M per taxpayer. The borrow-don't-sell strategy. Stepped-up basis at death. Roth conversion ladder.
Part 6
The Retirement Account Arsenal
Why retirement accounts are the most underused tax weapon available. Traditional vs Roth -- the real decision. Solo 401k at $69,000/year for self-employed operators. The Mega Backdoor Roth. SEP-IRA vs SIMPLE vs Defined Benefit. Self-directed IRA. The 72(t) distribution strategy.
Part 7
The Compensation Architecture
How wealthy business owners actually pay themselves. Salary vs distribution. The S-corp reasonable salary sweet spot. Deferred compensation. The executive bonus plan. Structuring compensation to minimize the total tax bill at the entity and personal level simultaneously.
Part 8
Advanced Tax Structures
Charitable Remainder Trust -- sell $600K in appreciated stock, pay zero capital gains, receive income for 20 years. Donor Advised Fund. The conservation easement. Private Placement Life Insurance -- the billionaire's wrapper. Captive insurance company. The installment sale.
Part 9
The International Layer
Foreign Earned Income Exclusion. Foreign Tax Credit. Puerto Rico Act 60 -- the only US escape route without renunciation. The CFC trap and how to navigate it. Transfer pricing -- what Fortune 500 uses, scaled down for operators.
Part 10
The Tax Operator's Toolkit
Software and systems. Who you actually need -- the difference between a CPA who files and a CPA who plans. How to find the right one and the exact interview questions to use. Red flags in tax advisors. Audit defense basics -- what triggers them, how to document, how to survive one.

I'm a CPA. I knew most of these strategies existed. What I didn't have was a guide on how to combine them into an actual operating structure. Written at a level I've rarely seen in public content.

Reader, Grampsaid Community
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Questions

Before You Decide

Tax evasion is hiding income. Everything in this playbook is structuring income so it qualifies for the rates the code assigns to it. The S-corp salary arbitrage is in the code. The Augusta Rule is Section 280A(g). QSBS is Section 1202. The code rewards specific behavior. This documents what that behavior is.
Most of the playbook has nothing to do with location. The S-corp arbitrage, the deduction machine, the retirement account arsenal, the real estate tax game -- all domestic, no relocation required. Part 9 covers the international layer for those who want it. The playbook specifies what each strategy requires.
Part 1 starts with the basics of how the system works. The S-corp play saves real money at $80K. The defined benefit plan and PPLI make more sense at $300K and above. The playbook specifies the threshold for each strategy.
Instant PDF the moment payment confirms. No waiting. Any device.

What was never supposed
to be written down.
Written down.

Some of what's in here is aggressive. Some of it is used by people you've heard of. All of it is real. What you do with this knowledge is entirely on you.

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