Pathfinding Consultants

When you sell an investment, a property, or another capital asset for more than you paid for it, the profit is called a capital gain. The IRS taxes capital gains differently depending on how long you held the asset before selling. Understanding whether your gain is short-term or long-term and which rate applies can make a significant difference in what you owe. These figures apply to assets sold during calendar year 2026. Returns are filed in early 2027. Source: IRS Topic No.

The IRS released its annual inflation adjustments for tax year 2026 in October 2025. These changes reflect amendments from the One Big Beautiful Bill Act (OBBBA), signed into law on July 4, 2025, which made most Tax Cuts and Jobs Act provisions permanent and introduced several new benefits for taxpayers. The same seven tax rates apply as in 2025 — 10%, 12%, 22%, 24%, 32%, 35%, and 37% but income thresholds have been adjusted upward by an average of 2.7% to prevent bracket cre

When a startup approaches a liquidity event or sale, the excitement can quickly turn into confusion once taxes enter the picture. Many founders celebrate the deal size without realizing that poor tax planning can quietly erode 20-40% of their gains. In my 10+ years advising startup founders, I’ve seen how a few early tax moves, like exercising ISOs before valuation spikes or qualifying for the QSBS exclusion, can save millions in taxes. Proper planning doesn’t just protect yo