Stock Option and Pre-IPO Planning
Stock Option and Pre-IPO Planning
Darrow Wealth Management specializes in helping individuals at public and private companies with their stock options and equity compensation. If you’re an employee (or former employee) at a pre-IPO company going public, merging, or getting bought out, work with an advisor experienced with strategic stock option planning, tax implications, and strategies to best manage sudden wealth.
Clients include executives and founders who have a variety of equity compensation, including:
- Incentive stock options (ISOs)
- Nonqualified stock options (NQSOs)
- Restricted stock awards (RSAs)
- Restricted stock units (RSUs)
- Founders shares
- Profits interests
- Employee stock purchase plans (ESPPs)
Many clients have a combination of common shares, exercisable options, and equity subject to vesting. Through our ongoing advisory relationship, we’re able to help clients with the entire equity compensation lifecycle from even before a grant to long after the sale.
Nationally Recognized Wealth Advisor in Stock Compensation
Selection of media appearances by Kristin McKenna CFP®, President of Darrow Wealth Management and a nationally recognized specialist in employee stock options and equity compensation.
Publications above reflect media organizations that have quoted and/or published articles authored by Kristin McKenna and should not be misconstrued as a current or past endorsement of Kristin McKenna, Darrow Wealth Management, or any of its advisors. Please refer to the media page for more information and links to published works.
Financial Advisor for Employee Stock Options
Especially for founders and 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 shares.
Our team of stock option advisors can work to help current and former employees and shareholders of public or pre-IPO companies:
- Plan for an IPO (or SPAC and direct listing) or acquisition (pre-IPO tax planning and exercise strategies, public or private acquisition planning)
- Develop an exercise strategy to balance potential tax benefits with risks of holding a concentrated stock position
- Assist with identifying and tracking shares likely to qualify for the tax-free sale of qualified small business stock
- Plan a tax-conscious liquidation strategy, considering different grants, holding periods, and outside cash needs
- Plan and execute a trading strategy including price targets, market vs limit orders, using options for long shares, considering liquidity constraints due to trading volume, liquidation order, and so on
- Assess ways to hedge the risks of a concentrated holding in publicly-traded stock, such as the use of call options on long shares, if permitted
- Assist in the drafting of 10b5-1 plan provisions
- Decide on a strategy to best use the proceeds, including funding multiple goals and investment management services to help you diversify sudden wealth
- Understand how vested and unvested stock options may be treated if you leave the company or retire
- Explore cashless or sell-to-cover exercises of stock options
- Approach employment negotiations around stock options and equity compensation
- Implement a multi-year diversification strategy through an ongoing wealth management advisory relationship
- Consider ways to further your charitable or legacy goals through different investment or trust vehicles
- Coordinate the approach with your tax advisor and estate planning attorney
Wealth Management Services
Darrow Wealth Management is a fee-only financial advisory firm and full-time fiduciary.
The Darrow Private Wealth Management Program offers clients a complete solution to their asset management and comprehensive financial planning needs.
Stock Option and Pre-IPO Planning Related Articles
Incentive Stock Options: Navigating AMT and AMT Credits
Updated for 2025 and 2026. If you have incentive stock options, you’ve probably heard of the alternative minimum tax (AMT). Essentially, the alternative minimum tax is a prepayment of taxes. In years when not subject to the AMT, you can receive an AMT credit. The credit reduces your tax liability
10b5-1 Trading Plans: Sales Strategies for Insiders
Rule 10b5-1 allows insiders to create pre-arranged trading plans as a way to remain compliant when managing their stock compensation. When structured properly, a 10b5-1 trading plan can provide corporate insiders an affirmative defense against insider trading allegations. This serves to balance the executives’ need to diversify with adequate measures
7 Ways to Manage Concentrated Stock Positions
What is a concentrated stock position? If one stock makes up more than 10% of your overall asset allocation, it’s probably too much. A diversified portfolio is the cornerstone of a risk-adjusted investment strategy. Since single stocks don’t move like the broader market, you’re exposed to much greater risk. Whether
Should I Accept a Tender Offer For My Stock Options?
As a startup or private company employee, you may have the option to participate in a tender offer from your employer. Accepting a tender offer means the company buys back some of your stock or options. While it won’t always make sense to participate, any opportunity for liquidity as a