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.
Financial Advisor for ISOs, NSOs, RSUs, and Equity Compensation
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
Specialists in Managing Stock Options and Planning After an IPO or Liquidity Event
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 financial advisors can help current and former employees — including shareholders of public or pre-IPO companies — build a strategy around five key components:
Pre-IPO and Sudden Wealth Event Planning
Comprehensive pre-IPO (SPAC or direct listing) wealth planning for stock compensation
Planning after an acquisition, sale, tender offer, or other stock-based windfall
- Long-term partner in navigating the transition to diversified wealth—from the strategic unwinding of concentrated equity to mapping the possibilities of your post-IPO life
Tax Strategy and Exercise Planning
Tax strategies for exercising ISOs and NSOs; managing RSUs; early exercises and AMT considerations
Tax-efficient sales strategies after an IPO lockup or tender offer; qualified small business stock planning
Tax-efficient wealth planning across the equity compensation lifecycle
Learn more about tax planning for stock options
Post-IPO Sales Strategy
-
Customized sales and trading strategies to manage post-IPO lockup liquidity and other windfalls
-
Advanced risk management to hedge concentrated single-stock holdings and diversify employer equity
-
Implement a multi-year diversification strategy through our ongoing advisory relationship
-
Full-time fiduciary and SEC-registered fee-only investment advisor
Equity Planning for Job Changes or Early Retirement
- Treatment of vested and unvested stock options and RSUs if you quit or retire
Navigating an acquisition or sale of a business and what it means for your equity
- Employment negotiations involving stock options and equity
Planning Beyond an IPO Windfall or Liquidity Event
Ongoing advisory support and asset management; integrating new wealth with your lifestyle and goals
Financial planning and retirement projections, major purchase feasibility analysis
Coordinate strategy with your tax advisor and estate planning attorney
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
Selling Shares When the Lockup Ends: Managing Equity and Liquidity Post-IPO
Selling Stock When Your IPO Lockup Expires If you have stock or options at a private company that’s going public, it’s important to get a plan in place for selling shares when the lockup expires. Current and former employees can’t sell immediately after an IPO due to lockup periods. Exactly
What Does an IPO Mean for Stock Options? What Happens to Employees When a Company Goes Public
Whether you work for a private company about to IPO or one that’s recently gone public, you may wonder what that means for employees and their stock options. An IPO provides liquidity for the company and serves as an exit strategy for founders and investors, while also creating a way
ISO Taxes: How AMT and AMT Credits Work + Avoiding AMT on ISO Exercises
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, which reduces your tax bill to reflect prepaid tax. The alternative
Frequently Asked Questions About Stock Option Advisory
Can a financial advisor help with my equity?
A financial advisor who specializes in stock options and equity compensation (a stock option advisor) can help manage stock compensation in a number of ways.
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.
Do I need a professional to help me manage my stock options and diversify?
If you are expecting a substantial windfall from company stock, strongly consider working with a financial advisor who specializes in equity compensation.
During an IPO or major sudden wealth event, it’s crucial to take control where you can to help ensure the best outcome. This typically involves a long-term partnership with a financial and tax advisor to manage your equity strategy, optimize for taxes, diversify proceeds, and map post-liquidity possibilities through planning and projections.
For example, we’ve flagged shares as eligible for tax-free QSBS sales, preventing major tax-saving opportunities from slipping through the cracks.
When should I speak with a professional about my equity?
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. Through our ongoing investment management relationship, we’ll discuss specialized diversification strategies and help you build a diversified portfolio to support your 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.
My company is doing a stock split or reverse stock split before going public. What does it mean for my shares?
It is not uncommon for a company to do a stock split or reverse split ahead of an IPO. A stock split reduces the price per share while a reverse stock split increases it. Neither will change the economic value of your shares, but there may be tax basis tracking implications.