Beancount.io LogoBeancount.io

9 tagged with "Tax Optimization"

Optimize your tax strategy for maximum savings legally

View all tags

Section 1256 Contracts and the 60/40 Tax Rule: A Trader's Guide to Form 6781
·mike

Section 1256 Contracts and the 60/40 Tax Rule: A Trader's Guide to Form 6781

Section 1256 splits gains on futures, broad-based index options, and qualifying forex 60% long-term and 40% short-term, capping the top federal rate near 26.8% versus 37% on equity options. A 2026 guide to Form 6781, the mark-to-market rule, and the three-year loss carryback.

tax
tax-planning
capital-gains
tax-optimization
+2
Qualified Charitable Distributions in 2026: A $111,000 Tax-Free Path From IRA to Charity
·mike

Qualified Charitable Distributions in 2026: A $111,000 Tax-Free Path From IRA to Charity

A complete 2026 guide to Qualified Charitable Distributions — the IRS-sanctioned strategy that lets retirees age 70½ and older route up to $111,000 from an IRA directly to a qualified charity without recognizing the distribution as taxable income.

charitable-giving
ira
tax-planning
retirement-savings
+3
Grantor Retained Annuity Trust (GRAT): The Wealth Transfer Strategy Founders Use to Move Appreciating Stock Tax-Free
·mike

Grantor Retained Annuity Trust (GRAT): The Wealth Transfer Strategy Founders Use to Move Appreciating Stock Tax-Free

How founders use zeroed-out GRATs to transfer pre-IPO stock appreciation to heirs tax-free, leveraging the IRS Section 7520 hurdle rate while preserving the lifetime estate exemption.

estate-planning
tax-planning
wealth-building
trust
+4
Net Unrealized Appreciation: The 401(k) Tax Strategy That Saves Six Figures
·mike

Net Unrealized Appreciation: The 401(k) Tax Strategy That Saves Six Figures

The Net Unrealized Appreciation election lets retirees pay long-term capital gains rates on employer stock distributed from a 401(k) instead of ordinary income, often saving more than $144,000 on a $1 million position. Covers eligibility under IRC 402(e)(4), the lump-sum distribution rule, and the most common mistakes that destroy the strategy.

tax-planning
retirement-savings
capital-gains
tax-optimization
+3
Roth Conversion Ladder: How FIRE Investors Tap Retirement Accounts Penalty-Free Before Age 59½
·mike

Roth Conversion Ladder: How FIRE Investors Tap Retirement Accounts Penalty-Free Before Age 59½

A Roth conversion ladder converts traditional IRA dollars to Roth in annual tranches, each unlocking penalty-free five tax years later — the core mechanism FIRE retirees use to tap pre-tax accounts before age 59½ while filling low tax brackets.

retirement-savings
tax-planning
ira
personal-finance
+3
Tax Loss Harvesting: The Year-Round Strategy That Can Save You Thousands in Capital Gains Taxes
·mike

Tax Loss Harvesting: The Year-Round Strategy That Can Save You Thousands in Capital Gains Taxes

Year-round tax loss harvesting can add 0.5%–1.5% in annual after-tax returns to a taxable portfolio. This guide explains the IRS netting order, the wash sale rule across taxable and IRA accounts, and a practical framework for harvesting short-term losses without losing the deduction.

tax-loss-harvesting
capital-gains
tax-planning
tax-optimization
+4
The Backdoor Roth IRA: A Step-by-Step Guide for High Earners in 2026
·mike

The Backdoor Roth IRA: A Step-by-Step Guide for High Earners in 2026

The Backdoor Roth IRA lets high earners contribute up to $7,500 a year to tax-free retirement growth by pairing a nondeductible traditional IRA contribution with a Roth conversion. Covers the five-step process, the pro-rata rule that derails most attempts, Form 8606 filing, and the recordkeeping that prevents being taxed twice.

ira
retirement-savings
tax-planning
personal-finance
+3
Mega Backdoor Roth: How High Earners Stash $47,500+ Per Year in Tax-Free Retirement Accounts
·mike

Mega Backdoor Roth: How High Earners Stash $47,500+ Per Year in Tax-Free Retirement Accounts

In 2026, the Mega Backdoor Roth can move up to $47,500 of after-tax 401(k) money into Roth above the $24,500 elective deferral limit. This guide covers how the strategy works, the three plan features it requires, how the 401(k) pro-rata rule differs from the IRA version, and the mistakes that quietly erode its value.

401k
retirement-plans
retirement-savings
tax-planning
+4
Cryptocurrency Tax Compliance Guide: Mastering IRS Requirements with Beancount.io
·mike

Cryptocurrency Tax Compliance Guide: Mastering IRS Requirements with Beancount.io

Complete guide to cryptocurrency tax compliance using Beancount.io. Master IRS requirements, automate tax reporting, optimize capital gains, and ensure accurate crypto tax filing.

cryptocurrency-taxes
crypto-tax-compliance
irs-reporting
form-8949
+11