Stock Option Advisor for Equity Compensation, Pre-IPO Planning, and Sudden Wealth
Stock Option Advisory Services for Employees, Executives, and Founders
Darrow Wealth Management specializes in stock option advisory and planning for individuals at public and private companies who are navigating equity compensation. If you’re an employee (or former employee) at a pre-IPO company preparing for an IPO, acquisition, merger, or tender offer, it’s important to work with a stock option advisor who understands the planning opportunities, tax considerations, and risk management decisions that often need to happen before liquidity.
We work with clients who receive different types 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 mix of common shares, exercisable options, and equity subject to vesting. Through an ongoing advisory relationship, we help clients plan across the full equity compensation lifecycle from early-stage grants and exercise decisions to diversification planning after a liquidity event.
Who We Help With Stock Option Planning
Equity compensation can be one of the most valuable and complex parts of your financial life. Effective planning depends on understanding not just what you’ve been granted, but also how upcoming events, tax rules, and personal goals intersect.
We work with individuals navigating stock option and equity compensation decisions, including:
- Stock option tax planning considerations
- Employees at late-stage private companies approaching an IPO or acquisition
- Founders and executives with concentrated company stock exposure
- Individuals deciding when (and how) to exercise ISOs or NQSOs
- People evaluating tender offers, secondary sales, or post-IPO diversification
- Employees considering job changes who want to understand how equity may be treated
Nationally Recognized Specialist in Stock Options and Equity Compensation
Kristin McKenna, CFP®, President of Darrow Wealth Management, is a nationally recognized specialist in employee stock options and equity compensation planning. Our work and perspectives have been featured by a range of media outlets.
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.
Advising Employees & Founders Expecting a Stock Option Payout
Financial Advisor for Employee Stock Options and Stock Option Planning
For founders, early employees, and executives, stock options can create a life-changing liquidity event and the most important planning opportunities often happen before you make irreversible decisions. A strong plan helps you weigh tradeoffs across taxes, concentration risk, timing, and long-term goals.
Our team of stock option advisors can help current and former employees — including shareholders of public or pre-IPO companies — build a strategy around:
1) Pre-IPO and Liquidity Event Planning
Plan for an IPO (including SPAC or direct listing) or a public/private acquisition: pre-IPO exercise and tax planning considerations (such as qualified small business stock)
Plan for tender offers, including how participation may fit into a broader diversification plan
2) Tax Strategy and Exercise Planning
Develop an exercise strategy designed to balance potential tax benefits and planning opportunities (such as early exercises or avoiding unwanted AMT surprises) with the risks of holding a concentrated position
Plan a tax-conscious liquidation strategy across different grants, holding periods while balancing outside cash needs
Ongoing coordination with outside tax advisor
3) Concentration Risk and Diversification Strategy
Plan and execute trading strategy in consideration of various factors such as price targets, market vs limit orders, liquidity constraints like lockup periods
Assess ways to hedge concentrated single-stock risk in publicly traded shares, such as utilizing options strategies like covered calls, if permitted
Implement a multi-year diversification strategy through an ongoing advisory relationship
4) Equity Planning Across Career Decisions
Understand how vested and unvested stock options may be treated if you leave the company or retire
Approach employment negotiations involving stock options and equity compensation
5) Planning Beyond the Liquidity Event
Portfolio construction and allocation of proceeds across multiple goals, including advanced investment management customization like direct indexing and sector screens
Financial planning projections, goal tracking, and major purchase feasibility analysis
Coordinate with your tax advisor and estate planning attorney to align the overall approach
Ongoing Wealth Management Support (As Part of the Advisory Relationship)
Darrow Wealth Management is a fee-only financial advisory firm and full-time fiduciary. All of our clients need ongoing support, and the Darrow Private Wealth Management Program provides investment management and comprehensive financial planning designed to help you implement a long-term strategy after a liquidity event.
Stock Option Advisory Insights
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
83(b) Election for Stock Options and Restricted Stock
For individuals with stock-based compensation, an 83(b) election has the potential to greatly reduce taxes on stock options or restricted stock. When you purchase unvested stock compensation and make the election, you recognize the taxable gain now (if any), instead of when the shares vest. What is an 83(b) election?
What Happens to Your Stock Options When You Quit or Leave the Company?
What happens to employee stock options or equity compensation if you leave the company? Before giving notice, understand how vested and unvested stock options and restricted stock units are treated if you quit, retire, or leave the company for other reasons. In brief, here’s what usually happens to stock options
Frequently Asked Questions About Stock Option Advisory
What does a stock option advisor do?
A stock option advisor helps individuals evaluate equity compensation decisions such as when to exercise stock options, how taxes may apply, and how those decisions fit into a broader financial strategy. The goal is to help you understand tradeoffs before making choices that may be difficult or impossible to reverse.When should I talk to a stock option advisor?
It is often helpful to speak with a stock option advisor before an IPO, acquisition, tender offer, or major exercise decision. Many planning opportunities exist before a liquidity event or before stock options are exercised.Can you help if I have both ISOs and RSUs?
Yes. Many individuals receive multiple types of equity compensation over time. Planning typically considers how each grant works, how vesting schedules align, and how potential tax outcomes may differ across equity types.Do you help with diversification after an IPO?
Yes. After an IPO, many individuals face concentrated stock exposure. Ongoing planning can help evaluate diversification strategies, timing considerations, and how equity proceeds may support long term financial goals.
Do you coordinate with my CPA or estate planning attorney?
Yes. Coordination with the entire advisory team is often essential, particularly on the tax side. Working together helps ensure decisions around equity compensation align with your broader tax and estate plans.
Are stock option advisory services offered on an hourly or project basis or only as part of an ongoing wealth management relationship?
Stock option advisory services are only offered to wealth management clients as part of an ongoing relationship, which includes asset management and comprehensive financial planning.
We are currently accepting new clients, with an investment minimum of $2,000,000 (upcoming liquidity events may qualify). Please see this FAQ page for more common questions about working with us.