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#capital-gains

Capital Gains

Track and report capital gains from investments

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8 min read

Depreciation Recapture Explained: The Tax Bill Waiting When You Sell Depreciated Equipment or Real Estate

Depreciation recapture taxes the deductions you already took when you sell a business asset at a gain — Section 1245 equipment gains are recaptured as ordinary income at rates up to 37%, while Section 1250 real estate depreciation is capped at 25%. With 100% bonus depreciation restored and the Section 179 limit at $2,560,000 for 2026, a fully expensed asset has a $0 basis from day one, so nearly the entire sale price becomes taxable. Here's how the rules split, a worked example, and five strategies owners use to manage the bill.

Mike Thrift

depreciationfixed-assetstax-planning
12 min read

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.

Mike Thrift

real-estatetax-planningcapital-gains
12 min read

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.

Mike Thrift

tax-planningcapital-gainsstartup
12 min read

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.

Mike Thrift

partnershipstax-planningtax
11 min read

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.

Mike Thrift

taxtax-complianceform-8949
12 min read

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.

Mike Thrift

tax-planningtax-compliancec-corporation
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