What To Do When Your IPO Lockup Expires

The end of your IPO lockup period is a milestone you’ve likely anticipated for years. Whether you’re a software engineer, product manager, or sales executive, this moment brings both opportunity and uncertainty. 

You’ve seen your equity value increase. You may have exercised options or made partial sales. Now, you need to make smart decisions for the IPO lockup period expiration. 

This article provides a general approach that can help you with a post IPO lockup expiration strategy. 

Navigating volatility and opportunity

When lockups (blackout periods) expire, a wave of insider shares often begin flooding the market, causing volatility. It can be tempting to act quickly or give in to selling pressures, but a measured approach can pay off. 

Watch trading volumes and price trends in the days and weeks after expiration. If the stock price holds or rises despite increased selling, it signals market confidence. If it drops sharply, consider waiting for stabilization. 

Many professionals use a phased selling strategy. They divide selling their shares into parts over weeks or months. This strategy is designed to help manage market risks and timing risk. This approach can also help prevent making emotional decisions. 

Optimizing tax strategies

Equity compensation is complex, and tax consequences can be significant. The tax treatment of shares from RSUs (Restricted Stock Units), ISOs (Incentive Stock Options), NQSOs (Non-Qualified Stock Options), or ESPPs (Employee Stock Purchase Plans) differs. 

For example: 

• Selling ISO shares within one year of exercise or two years of grant triggers ordinary income tax rates and possibly the Alternative Minimum Tax (AMT). 

• NQSOs are taxed as ordinary income if sold within one year of exercise and taxed as capital gains if sold after one year of exercise. 

• RSUs are taxed as income when they vest, with further gains taxed as capital gains. Holding shares for more than a year can qualify you for a long-term capital gains rate, which tends to have lower tax impact. 

Modeling different scenarios is important to help optimize your tax outcome. Consider timing sales in lower-income years, using charitable vehicles like donor-advised funds, or employing a long-short strategy for tax efficiency.

Make sure you have a complete understanding of your financial situation before making any decisions. Transparency and thoroughness are essential. 

Protecting your wealth

You may feel comfortable with risk but concentrated equity positions can be dangerous. Your financial future shouldn’t hinge on one company, no matter how promising.

Diversification is a strategic move, not a lack of loyalty. Consider selling a portion of your IPO shares and reinvest in a mix of assets such as index funds, bonds, real estate, or even startups. Explore tech-forward solutions like direct indexing for personalized diversification. Consider using hedging strategies (protective puts, collars) to manage downside risk while retaining upside potential. 

The goal is to build resilience and reduce volatility, which can contribute to your wealth potential regardless of your company’s fate. 

Outsmarting your own biases

Even the most analytical minds are vulnerable to behavioral biases. The “endowment effect” is when people assign more value to things simply because they own them. This behavioral finance principle may influence your perception of your shares. Loss aversion may keep you from selling when you should. 

Focusing on IPO prices or exercise prices can change how you see value. You might feel pressured to follow what your colleagues do.

To counter these biases, set clear rules for selling. Use data to create fixed percentages at regular intervals or set price targets. Use automation where possible to remove emotion from the process.

If you’re skeptical of financial advice from banks or brokers, seek out advisors who understand your mindset and can offer transparent, personalized guidance. 

Building your strategy

You may have already made partial sales or exercised options, but a comprehensive strategy is essential.

Start by defining your goals. Do you need cash for a big purchase? Do you want to fund a startup? Or are you planning for early retirement? 

Map out your equity holdings, tax scenarios, and diversification plan. Document your decisions and revisit your strategy as your situation evolves. Use technology to track progress and stay informed. 

Remember, the lockup expiration is not just a financial event, it’s a chance to take control of your future. 

Turning opportunity into lasting value

When your post IPO lockup period ends, it’s a moment of both opportunity and responsibility. By approaching it with data-driven discipline, tax awareness, diversification, and behavioral insight, you can turn uncertainty into clarity. Post IPO, you may have the opportunity to convert your equity into wealth. You might also turn your post IPO equity into enduring wealth. 

Treat this milestone as a reflection of your hard work and strategic thinking. With the right approach, you’ll be well-positioned to build lasting value for yourself and your future. 

If you have upcoming IPO lockup expirations and haven’t yet notified your Mercer Advisors wealth advisor, be sure to connect soon. 

Not a Mercer Advisors client and want to know more about planning your financial future with confidence? We’ve been advising individuals and families for 40 years on IPOs and other equity opportunities and would be happy to help. Let’s talk.