How Sports Card and Collectibles Reselling Is Taxed: The 28% Rate, Cost Basis, and the IRS's Three Buckets
Sports cards are taxed as collectibles at up to 28% long-term capital gains, higher than stocks.
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Capital Gains
Track and report capital gains from investments
The Deferred Sales Trust: How Business Owners Defer Capital Gains on an Exit Without a 1031 Exchange
A deferred sales trust lets a business owner spread capital gains tax from a sale over 10-20 years under IRC Section 453 with no like-kind reinvestment requirement, but setup and management fees commonly total $100,000-$300,000+ over a decade and the IRS has never issued formal guidance approving the structure.
Ireland's Budget 2026: What the VAT Cut and New Reliefs Actually Mean for Small Business Owners
Ireland cut VAT on food, catering, and hairdressing from 13.5% to 9% on July 1, 2026, raised the entrepreneur relief cap to €1.5M, and boosted the R&D credit to 35% — but the minimum wage hike to €14.15 and pension auto-enrolment landed six months earlier. Here's what each change means for small business books.
Billboard Ground Leases: A Landowner's Guide to Rent, Escalators, and Taxes
US billboard ground leases pay landowners 15–20% of ad revenue or flat rent — tax treatment and escalators over 10–20 years.
Opportunity Zones 2.0: A 2026 Planning Guide for Real Estate Sponsors and Family Offices
The One Big Beautiful Bill Act made Qualified Opportunity Zones permanent and introduced rolling 5-year deferrals, decennial map redesignations starting July 1, 2026, a new rural fund class (QROF) with a 30% basis step-up at year 5, and $10,000-per-return reporting penalties. Here is the planning sequence for sponsors and family offices through the 2026–2027 window.
Section 1202 QSBS After the One Big Beautiful Bill Act: Tiered Holding Periods, the $15 Million Cap, and Trust Stacking
How the One Big Beautiful Bill Act rewrote Section 1202 QSBS — a tiered 50/75/100% gain exclusion at three, four, and five years; a $15 million per-issuer cap; a $75 million gross asset threshold at issuance; and non-grantor trust stacking that can lift a founder's combined exclusion well past the single-taxpayer limit.
Section 1202 QSBS Exclusion: A Founder's Guide to $15 Million in Tax-Free Gains
Section 1202 lets founders, early employees, and angel investors exclude up to $15 million of capital gains from federal tax. This guide covers the OBBBA changes, the five eligibility gates, the new 3/4/5-year tiered holding period, Section 1045 rollovers, and stacking strategies that multiply the per-issuer cap across family members and non-grantor trusts.
Section 736 Payments to Retiring or Deceased Partners: 736(a) vs. 736(b), Hot Assets, and the Goodwill Lever
Section 736 splits liquidating payments to a retiring partner into 736(b) property payments (capital gain, no firm deduction) and 736(a) income or guaranteed payments (ordinary income with self-employment tax, deductible by the firm). The service-partnership carve-out, Section 751 hot assets, and Section 754 election together determine whether six- or seven-figure tax dollars land on the retiree or the firm.
Form 1099-DIV Box 3: The Return-of-Capital Basis Trap for REIT, BDC, and MLP Investors
A practical walkthrough of Form 1099-DIV Box 3 nondividend distributions — how return-of-capital payments from REITs, BDCs, MLPs, and managed-distribution funds reduce your cost basis under IRC Section 301(c)(2), convert into immediate capital gain under 301(c)(3) once basis hits zero, and what records you need to keep so the IRS matching program never catches you short.
Section 1059 Extraordinary Dividend Basis Reduction: The Corporate Shareholder Trap That Turns Tax-Free Dividends Into Immediate Capital Gain
Section 1059 reduces a corporate shareholder's stock basis by the nontaxed portion of an extraordinary dividend — 5% threshold for preferred, 10% for common — when received within two years of acquisition, with excess immediately taxed as capital gain. This guide covers the thresholds, the 85-day and 365-day aggregation rules, the FMV election, the non-pro-rata redemption exceptions, and the lot-level bookkeeping that keeps corporate finance teams out of audit trouble.
When Capital Gain Becomes Ordinary Income: Section 1239 and the Family Business Trap
Section 1239 converts capital gain to ordinary income on sales of depreciable property between related parties — including a controlling owner and their own corporation, partnership, or trust. The constructive ownership rules under Section 267(c) make the more-than-50% threshold easier to cross than family business owners expect.
California Proposition 19 and the End of the Old Parent-Child Property Tax Bargain: A 2026 Guide for Heirs of California Real Estate
How California's Proposition 19 replaced Section 63.1 for parent-child transfers after February 16, 2021 — the family home and farm rules, the one-year occupancy requirement, the BOE-19-P and BOE-266 filings, the $1,044,586 value cap floor, and the step-up-basis trade-off that determines whether to gift during life or transfer at death.