Strategic Planning for the Exercise and Sale of Stock Options

Darrow Wealth Management regularly works with individuals who have incentive stock options (ISOs) or non-qualified stock options (NQSOs) to develop a plan to exercise and diversify shares. If your employer is going public or getting bought out, it’s important to work with a financial advisor experienced with strategic stock option planning and the tax implications.

Financial Advisor for Stock Options

Especially for early employees, stock options can create a major liquidity event that transforms your financial life. To maximize the opportunity, it’s critical to get the right team of advisors in place before making irreversible decisions with your stock options.

Our team of CERTIFIED FINANCIAL PLANNER™ professionals can work to help you:

  • Discuss your goals to identify how to best utilize stock options in your financial plan or retirement plan
  • Develop an exercise strategy considering possible tax implications like triggering the alternative minimum tax (AMT) alongside the risk of holding a concentrated stock position
  • Analyze different holding periods when developing a liquidation strategy, factoring in risk, cash needs, and taxes
  • Coordinate the approach with your CPA and tax advisor
  • Decide on a strategy to best use the proceeds, including funding multiple goals and investment management services to help you diversify after sale
  • Understand how vested and unvested stock options may be treated if you leave the company or retire
  • Explore cashless exercises of stock options
  • Implement a multi-year diversification strategy through an ongoing wealth management advisory relationship


Schedule Phone Consultation



Wealth Management Services

Darrow Wealth Management is a fee-only financial advisory firm and full-time fiduciary. We regularly work with employees and executives with stock options, particularly after an IPO, acquisition, or direct listing. By integrating financial planning with investment management, our goal is to help busy professionals build and grow their wealth.

Investment Advisor · Financial Planning

Tax-Efficient Planning · Retirement Projections

Financial Modeling & Analysis

Fee-Only Fiduciary Wealth Management Services Boston Financial Advisor

Stock Option Insights: From Acquisitions to IPOs

Stock options after IPO
Building Wealth

Managing Stock Options in a Direct Listing – Going Public Without an IPO

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…
Stock options IPO financial advisor
Building Wealth

What Does an IPO Mean for Employees? What to Do When Your Company Goes Public.

There were nearly 500 IPOs in 2020. According to data from FactSet, that's just 67 shy of the combined total between 2015 and 2017. And the race to go public isn't slowing down. As of the end of February 2021, more than 230 companies have gone public this year alone.…
Stock options after IPO
Stock options

What Happens to Stock Options When a Public Company Goes Private?

With so much emphasis on IPOs, investors are sometimes surprised when publicly traded companies decide to go private. There are many reasons a company may choose to go private. Dry powder flowing into private equity funds only fuel the trend. For employees of a public company going private via buyout,…
Own too much company stock

If You Own Too Much Stock In One Company, It’s a Good Time To Consider Diversifying

Can you own too much of your employer's stock? Undoubtedly, yes. Does holding a lot of company stock create the potential for a large windfall? Also, yes. For employees, it can be difficult to know how much company stock is too much. But identifying a concentrated position is often just…