Insights from Kristin McKenna CFP®, a nationally recognized expert in employee stock options and equity compensation. Articles cover a range of topics about employer stock, such as exercising options, tax planning strategies, Section 1202, considerations during a lock-up, and what to do with the proceeds. The blog also discusses liquidity events such as IPOs, mergers, or acquisitions and what happens to stock if you’re laid off or leave the company. Key insights for founders and executives on strategic stock option planning and strategies to best manage sudden wealth.
Includes QSBS changes from the July 4, 2025 OBBB tax bill. If you invested in a startup or small business (founders, employee exercise of stock options, business owner), you need to know about qualified small business stock. If eligible, you may be able to exclude up to 100% of the gain
If your company (e.g. the target company) is getting acquired, you’ll want to understand what happens to your stock. When a company buys another company, what can happen to your stock depends on several factors, including if you own stock outright or vested/unvested stock options/RSUs. Here’s more on what happens
6 tax strategies for incentive stock options and AMT in 2025 and 2026 Triggering the alternative minimum tax isn’t the end of the world, but you don’t want to do it by accident. Here are six tax planning strategies to consider when exercising and selling ISOs in 2025: Exercise early
Is exercising stock options right before a company goes public a good idea? Employees with pre-IPO incentive or non-qualified stock options often wonder if they should exercise before the company goes public (perhaps during a final open window) or wait until after the IPO. Assuming you have the cash on
Working for a startup can pay off big financially, but a lot must go right along the way. If you are considering taking a job at a startup or private company with plans for an exit, there’s a lot to consider before accepting an offer. Depending on your life stage
The Instacart IPO is on hold…again. What should employees with stock options do when their employer’s IPO stalls? In truth, best practices around an IPO are sometimes skewed towards what not to do. If you have stock or options from a company that’s about to go public, there may be
Quite simply, a down round is when a company raises money at a lower valuation per share relative to earlier financing rounds. A simple example: a startup raises a Series B at a $30M post-money valuation and a Series C at a $20M post-money valuation. Working for a startup involves
More companies entered the public markets in 2021 than any other year on record. From traditional IPOs or SPACs, and even direct listings, it was a banner year for exits. Unfortunately, the sharp pullback in the equity market to start 2022 is leaving employees and shareholders subject to a lock-up agreement in
Although the most common way for a company to go public is through the traditional initial public offering (IPO) process, it’s not the only method. Although SPACs (special purpose acquisition companies) were first created in 1993, they’ve recently became a very popular way for a company to go public. This
What happens to stock options if a company goes public without an IPO? A Direct Public Offering (DPO) or direct listing is a way for a company to list itself on a public stock exchange without the traditional Initial Public Offering (IPO) process. If you have employer stock options and