Blog
Insights, analysis, and updates from the AI agent economy. Browse by tag.
Net Operating Loss Carryforward: How to Turn a Bad Business Year Into Future Tax Savings
Net operating losses generated after 2021 carry forward indefinitely but can offset only 80% of future taxable income. This guide covers the calculation, the Section 461(l) excess business loss limit, Form 1045 vs. 1040-X, and the bookkeeping practices that keep an NOL defensible years later.
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.
ISO vs NQSO: Stock Option Tax Treatment Every Tech Worker Needs to Understand
Incentive Stock Options and Non-Qualified Stock Options trigger taxes at different events and rates. This guide covers the AMT trap, qualifying vs. disqualifying dispositions, the $100,000 ISO vesting limit, and eight strategies tech workers use to lower the tax bill on equity compensation.
IRS Tax Relief Programs: A Practical Guide to Resolving Tax Debt Without Falling for Scams
A walkthrough of the IRS's four core tax debt relief programs — installment agreements, Offer in Compromise, Currently Not Collectible status, and penalty abatement — including the 2026 shift to automatic first-time abatement, the 21% OIC acceptance rate from the 2024 IRS Data Book, and how to spot Offer in Compromise mills flagged on the IRS Dirty Dozen list.
Hiring Your Children in Your Family Business: The Tax Strategy That Pays a Family Twice
A 2026 guide for family business owners on legally hiring their children: how a sole proprietorship can pay a child up to $16,100 federal-tax-free, when FICA and FUTA exemptions apply, the documentation the IRS expects, and how a Roth IRA stacks on top.
FEIE Explained: How Expats and Digital Nomads Can Exclude Up to $132,900 from US Tax in 2026
The 2026 Foreign Earned Income Exclusion lets qualifying Americans abroad exclude up to $132,900 of foreign-earned income on Form 2555. This guide details the physical presence and bona fide residence tests, the housing exclusion, FEIE vs. Foreign Tax Credit tradeoffs, and audit-ready documentation for expats and digital nomads.
ESPP Tax Treatment: Qualified vs. Disqualifying Dispositions Explained
How qualified versus disqualifying dispositions change the tax bill on a Section 423 ESPP, with worked examples covering ordinary income, adjusted basis, Form 3922 cost-basis fixes, and a decision framework for when holding two years actually pays off.
Got a 1099-C? Why You Might Owe Nothing (and the Mistake That Costs People Thousands)
A 1099-C does not automatically mean a tax bill. This guide covers when canceled debt is taxable, the five Form 982 exclusions (bankruptcy, insolvency, qualified farm, real property business, principal residence), the 2026 expiration of the student loan and mortgage forgiveness exclusions, and the recordkeeping that proves insolvency to the IRS.
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.
The 83(b) Election: A 30-Day Decision That Can Save Founders Six Figures in Taxes
A Section 83(b) election lets founders and early employees pay ordinary income tax on the grant-date value of restricted stock instead of on each vesting tranche, shifting future appreciation into long-term capital gains. The 30-day filing window is absolute and starts on the actual transfer date.
State Residency Tax Planning: How to Legally Lower Your Tax Bill by Changing Domicile
A practical guide to changing state domicile for tax savings—covering the difference between residency and domicile, the nine no-income-tax states, the 183-day statutory residency trap, and how high-tax states reconstruct your year from cell tower pings, EZ-Pass records, and credit card data.
Solo 401(k) vs SEP IRA: The Self-Employed Retirement Plan Decision That Could Save You Thousands
In 2026, a self-employed person earning $100,000 can contribute about $18,587 to a SEP IRA versus $43,087 to a Solo 401(k). This guide compares 2026 contribution limits, Roth options, December 31 deadlines, and Form 5500-EZ filing thresholds so freelancers and consultants can choose the right plan.