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QSBS and Significant Redemptions

QSBS and Significant Redemptions

Qualified small business stock (“QSBS”) is a special type of stock that can result in 0% federal tax on the gain (up to a cap) from a sale if held more than 5 years. That is the good news. The bad news is that a company can accidentally disqualify otherwise eligible...
Using a Roth IRA to Fund Your Start-up

Using a Roth IRA to Fund Your Start-up

Updated. Originally posted May 13, 2022  Can I Use a Self-Directed Roth IRA to Fund My Start-Up? I was asked this question by three different clients yesterday. Ever since it was revealed that Peter Thiel reportedly accumulated billions of dollars inside his Roth IRA,...
QSBS Trust Stacking

QSBS Trust Stacking

May 2026 Update On May 20, 2026, Treasury Assistant Secretary for Tax Policy Kenneth Kies said during a conference in Washington, D.C., that the IRS is preparing guidance on the expanded exemption aimed at curbing what he described as stacking abuse. “Let me just warn...
Fixing Discount Stock Options

Fixing Discount Stock Options

So, you accidentally granted one or more discount stock options. Now what? As quick background, a discount stock option has an exercise price below the fair market value of the underlying stock on the date of grant.[1] For whatever reason, Congress doesn’t like this...
The Double Merger

The Double Merger

A “double merger” is exactly what it sounds like: two mergers completed back-to-back as part of a single, integrated transaction. In the first step, the buyer acquires the target through a reverse triangular merger, with the target surviving as a wholly owned...