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Anna's Deep Dives

_{Just facts, you think for yourself}

Most people treat tax season like an autopsy.

You hand your CPA a shoebox of receipts in April. Then you hope the damage isn't fatal.

And that’s the problem. That approach relies entirely on history. A receipt shows what you spent. It doesn't show what you can keep.

You need to stop viewing your financial data as an archive. It’s a predictive dataset.

And with the "One Big Beautiful Bill Act" (OBBBA) passing in July 2025, the difference between looking backward and looking forward just got very expensive.

We’re talking about losing control of your MAGI before you even realize you’ve hit the cliff.

We’ve built the checklist to turn that "tax prep" meeting into a "counter-offensive" strategy session.

Ready to take control?

The CEO's Briefing Packet: Stop Paying for Data Entry If you send a disorganized mess, you pay your CPA to organize it. If you send a structured briefing, you pay them to think. We explain why the "Effective Tax Rate" is a vanity metric you should ignore, and how to use the 15-20-15-10 framework to force a high-level strategic conversation. Stop being a historian. Start being a strategist. [Click here for Chapter 1: The 'CEO's Briefing Packet' (Premium)]

The Income Tax Bomb: The QBI Trap For business owners, the QBI deduction is a 20% discount on your tax rate. But it has a kill switch. Earn one dollar over the phase-out range ($400k-$550k for joint filers in 2026), and that deduction evaporates. We show you how to calculate your "Run-Rate" exposure and spot the exact moment your deductions stop working. [Read Chapter 2: The 'Income Tax Bomb' Dossier (Premium)]

The Estate Tax Bomb: Your "Dead" Net Worth Most people track their "living" net worth. The IRS tracks your "Gross Estate." And it’s almost always higher than you think (hello, life insurance death benefits). We break down the "Catastrophe Number," the liquidity gap that forces fire sales, and why your state’s estate tax exemption (often just $1M-$5M) might be the real ambush waiting for your heirs. [See Chapter 3: The 'Estate Tax Bomb' Dossier (Premium)]

The Action Packet: Send This Email Amateurs send attachments in dribs and drabs. Professionals send a dossier. We give you the exact security protocols to use (don't email your social security number) and a fill-in-the-blank email template to send your CPA two weeks before the meeting. It sets the agenda, demands specific answers on the OBBBA, and proves you are a high-value client. [Get Chapter 4: The 'CPA-Ready' Action Packet (Premium)]

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Table of Contents

^{(Click on any section to start reading it)}

Chapter 1: The 'CEO's Briefing Packet' (The 'Why')

1.1: Shifting from Reactive 'Tax Prep' to Proactive 'Tax Strategy'

• Why this is NOT a 'tax document' checklist; it's a 'strategic arsenal' checklist.

• The goal: Force a high-level strategic conversation with your CPA, not just a 'what happened last year' review.

• Using this packet to establish control and set the agenda for your '2026 Counter-Offensive' planning session.

• The deliverable: A single, organized 'briefing packet' you can send to your CPA to prove you are a serious, high-level client.

Chapter 2: The 'Income Tax Bomb' Dossier (Quantifying Your 'Run-Rate' Exposure)

2.1: Core Income & Tax Rate Analysis

• Gathering your last 3-5 years of Federal and State Tax Returns (Forms 1040, 1040-SR, and state equivalents).

• Pinpointing your 'Marginal Tax Bracket' vs. 'Effective Tax Rate' (This is key for 'Tax Bracket Harvesting' in Week 8).

• Consolidating all income sources: W-2s, K-1s (from S-Corps/Partnerships), 1099-DIV, 1099-INT, 1099-NEC.

2.2: The 'QBI Apocalypse' Audit (For Business Owners & Specialists)

• Locating your Form 8995 or 8995-A (Your QBI Deduction).

• Calculating the exact dollar value of the 20% Qualified Business Income (QBI) deduction you are set to lose.

• Identifying if you are a 'Specified Service Trade or Business' (SSTB) and how that impacts your current vs. future planning.

2.3: Retirement Account Vulnerability (The 'Tax-Deferred' Time Bomb)

• Consolidating balances for all Traditional IRAs, 401(k)s, 403(b)s, and Roth accounts (for you and your spouse).

• Reviewing current contribution & conversion strategy (Are you doing Backdoor Roths? Are you contributing to Traditional?).

• Assessing your RMD (Required Minimum Distribution) 'tax bomb' – This is critical for the 'Roth Conversion' model in Week 2.

Chapter 3: The 'Estate Tax Bomb' Dossier (Quantifying Your 'Legacy' Exposure)

3.1: Establishing Your 'Total Estate' Net Worth (The 'Catastrophe Number')

• Creating a consolidated balance sheet: All brokerage accounts, real estate (primary, secondary, rental), business equity, life insurance death benefits, and other high-value assets.

• Differentiating 'liquid' vs. 'illiquid' assets (Crucial for planning how to pay an estate tax).

• Understanding 'probate' vs. 'non-probate' assets and how both are counted for federal estate tax.

3.2: Auditing Your Current 'Shields' (Trusts, Gifting, & Insurance)

• Gathering all current trust documents (Revocable Living Trusts, ILITs, SLATs, GRATs, etc.).

• Compiling your lifetime 'gifting' history (Locating all prior Form 709 Gift Tax Returns).

• Quantifying your (and your spouse's) remaining 'Lifetime Gift Tax Exemption' (This is the 'use it or lose it' asset).

• Auditing all life insurance policies (owner, beneficiary, death benefit) – especially those inside an ILIT.

3.3: The 'State-Level' Tax Ambush

• Identifying if you live in (or own property in) a state with its own estate or inheritance tax.

• Understanding your state's exemption limit (often $1M - $5M, far lower than the current federal $13M+).

• The 'portability' trap: Most states do not have portability for their state estate tax exemption, creating a massive threat for married couples.

Chapter 4: The 'CPA-Ready' Action Packet

4.1: Final Collation & The 'Executive Summary' Memo

• How to 'package' this information: Creating a secure digital folder (e.g., encrypted zip, secure client portal) for your CPA.

• A 'fill-in-the-blank' email template to send to your CPA with the subject line: 'ACTION: Strategic Planning for 2026 Tax Sunset'.

• The 5 'Key Questions' this packet prepares you to ask.

Baked with love,

Anna Eisenberg ❤️