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Anna's Deep Dives

_{Just facts, you think for yourself}

Most investors are obsessed with market returns.

They spend hours checking tickers and worrying about the next crash.

But there’s a much bigger leak in your bucket.

It’s called "Sequence of Taxation Risk."

In 2026, the rules change. New deduction phase-outs and "cliffs" are coming.

If you pull $50,000 from the wrong account in the wrong year, you could trigger a chain reaction that costs you thousands in extra Medicare premiums and lost deductions.

You can’t "average out" a tax penalty. Once it’s gone, it’s gone.

We’ve spent the last few weeks pulling back the curtain on how the government plans to monetize your retirement. Frankly, the math is a bit of a wake-up call.

Here is the blueprint to build a portfolio that’s hard to tax.

The Invisible Drag: Why your returns are lying to you
Two investors can have the exact same 7% return, but one ends up with $1 million less in after-tax wealth. We break down the "Tax Drag Coefficient"—the silent expense ratio you aren't tracking.
[Click here for Section 1: The Sequence of Taxation Risk]

The SALT Torpedo: The $500k minefield
There’s a specific income zone between $500,000 and $600,000 where every extra dollar you earn actually makes you poorer. We look at "SALT 2.0" and the new deduction haircuts that act like a stealth tax on high earners.
[Dive into Section 2: SALT 2.0 and the Itemized Cap]

The Dividend Trap: Why "safe" income is a bug, not a feature
Yield feels conservative, but it quietly raises your "tax floor" and forces you to pay the government when you don’t need to. We explain why the "Dividend Trap" is the quickest way to lose control of your AGI.
[Uncover Section 3: The Dividend Trap]

Basis Engineering: Turning your portfolio into a timing weapon
Most people treat capital gains as an annoyance. We treat them as a dial. Learn how to use "synthetic income" and specific lot selection to choose the least expensive year to be wealthy.
[See Section 4: Capital Gains Sequencing]

Loss Harvesting 2.0: Building your tax inventory
A loss isn’t a failure—it’s inventory. We show you how to build a "harvest ladder" so you always have a reserve of losses to deploy when the government tries to hike your rates.
[Read Section 5: Banking Losses as a Strategic Reserve]

The Withdrawal Architecture: Which dollar is cheapest?
Forget the "Taxable First" rule of thumb. It’s outdated. We’ve built a Withdrawal Matrix that tells you exactly which bucket to tap based on the specific "year-type" you're in.
[Explore Section 6: The Withdrawal Architecture Blueprint]

The goal isn't just to beat the market.

It's to make sure you actually keep what you win.

In a world full of noise and spin, we stay focused on facts. No hype, no hidden motives — just honest reporting.
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Table of Contents

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

Section 1: The Sequence of Taxation Risk

• The Invisible Drag: Defining the Tax Drag Coefficient

• The Return Illusion: Why After-Tax Wealth Decouples from Market Performance

• Systemic Collision: How Federal, State, and Medicare Systems Interact

Section 2: SALT 2.0 and the Itemized Cap

• The $500k Minefield: Navigating the Stealth Tax Zone

• The Deduction Haircut: How the New Phase-Outs Function

  • Phase-out Mechanics for High Earners

  • The "Clip" vs. The "Cliff": Identifying the Dangerous Thresholds

• Strategic Mitigation: Leveraging PTET and Timing Itemized Deductions

Section 3: The Dividend Trap

• The Tax Floor Problem: Why Forced Yield Erodes Control

• Qualified vs. Ordinary: The True Cost of "Conservative" Income

• Asset Location 2.0: Moving Yield Out of the Line of Fire

  • The Case for Growth-Oriented Taxable Accounts

  • Re-evaluating Bond Placement in a High-Rate Environment

Section 4: Capital Gains Sequencing

• Basis Engineering: Treating Your Cost Basis as a Timing Dial

• Specific Lot Selection: The Art of "Synthetic Income"

• The 0% Bracket Strategy: Leveraging Volatility to Reset Basis

Section 5: Banking Losses as a Strategic Reserve

• Loss Harvesting 2.0: Beyond the December 31st Chore

• The Harvest Ladder: Creating Long-Term Tax Optionality

• Wash Sale Navigation: Maintaining Market Exposure While Booking Losses

Section 6: The Withdrawal Architecture Blueprint

• The Withdrawal Matrix: Matching Buckets to "Year-Types"

• Solving the IRMAA Puzzle: Managing Medicare Surcharges

• The Fortress Portfolio: Final Protocols for a Tax-Resistant Future

Baked with love,

Anna Eisenberg ❤️