Explainers, playbooks, and pillar articles.
Pieces written to actually inform a decision — not to rank for a keyword. Every article is by-lined and dated. Every position cites authority.
The 2026 Capital Gains Tax Checklist
Stocks, options, equity compensation, and digital assets on one checklist — holding period, basis and lot selection, wash sales, §1256, harvesting, and state treatment.
Crypto investor? Get the new 1099-DA Readiness Checklist — what to fix before cost-basis reporting arrives in early 2027 — or the 2026 Crypto Tax Preparation Checklist.
Start with these pillars.
Form 1099-DA Explained, Box by Box
Covered vs. noncovered crypto, why basis is blank, the new Form 8949 boxes G–L, and how mismatches turn into CP2000 notices.
Read article Capital marketsThe 2026 Capital Gains Guide for Stock & Options Investors
Holding period and character, basis and specific identification, what the 1099-B leaves out, wash sales across accounts, §1256 contracts, QSBS, harvesting, the 3.8% surtax, and state treatment.
Read article Founders & solopreneursThe AI Solopreneur Tax Stack: Entity, Retirement, §199A, §174, Nexus
The complete tax-strategy stack for AI-native founders, indie SaaS, and creator-economy operators. Five layers, in the order to install them.
Read article Global & cross-borderThe U.S. Expat Tax Playbook: FEIE, FTC, Treaty, FBAR & PFIC
The field guide for Americans abroad and inbound foreign nationals. The choices that move the bill, the traps that quietly create six-figure liabilities, and the path back if you're behind.
Read article Crypto & digital assetsThe 2026 Crypto Tax Guide for U.S. Investors
Cost basis selection, 1099-DA, DeFi classification, wash-sale positioning, and the thirteen line items most filers get wrong.
Read article Equity compensationRSUs, ISOs, and NSOs: A Tax Playbook for Tech Employees
Vesting mechanics, AMT, sell-to-cover, 83(b), and the timing decisions that make or break the math.
Read article Multi-stateLeaving New York or California: How Residency Actually Works
Domicile vs. statutory residency, the day-count trap, and the documentation file that survives a residency audit.
Read article IRS representationThe CP2000 Playbook: How to Respond Without Overpaying
What a CP2000 is, the reply-by date that controls, crypto and 1099-DA mismatches, and the step-by-step response.
Read articleBrowse by cluster.
Capital markets & capital gains
Founders & solopreneurs
- AI solopreneur tax stack
- S-corp election break-even (coming)
- Mega-backdoor Roth via Solo 401(k) (coming)
- §174 capitalization tracking (coming)
Global & cross-border
- U.S. expat tax playbook
- FBAR vs. FATCA reporting (coming)
- PFIC analysis & QEF election (coming)
- §877A exit-tax modeling (coming)
Digital assets
- The 2026 crypto tax guide
- HIFO vs. FIFO in practice (coming)
- 1099-DA: what changes in 2026 (coming)
- DeFi classification framework (coming)
Equity compensation
- RSU, ISO, NSO playbook
- ISO AMT modeling (coming)
- QSBS stacking (coming)
- 83(b) elections explained (coming)
Multi-state
- Leaving NY or CA
- Convenience-of-the-employer rule (coming)
- Part-year return mechanics (coming)
- PTET elections by state (coming)
IRS representation
- The CP2000 playbook
- Offer in Compromise reality (coming)
- Penalty abatement checklist (coming)
- Audit response framework (coming)
Business & entity
- When an S-corp actually works (coming)
- Reasonable comp studies (coming)
- QBI optimization (coming)
- Solo 401(k) playbook (coming)
High-net-worth
- Charitable vehicle selection (coming)
- Installment sale mechanics (coming)
- Trust coordination basics (coming)
- Pre-exit planning timeline (coming)
Reading only gets you so far.
These guides cover the general rules. Your facts decide the answer — that is a fifteen-minute conversation.