Keith Underwood

We start with you. I take the time to understand your priorities, goals, and comfort with risk so we can build a strategy that reflects your life—not just market assumptions.

Using what we learn together, I design a tailored investment approach that supports your long-term objectives, whether it's retirement, education funding, or tax-efficient growth—all with a clear, diversified plan.

Once your plan feels right, I bring it to action. I help you select the investment solutions that best fit your strategy, making the process straightforward and aligned with your preferences.

Your financial life evolves, and your strategy should too. I stay connected with you regularly to review progress, adjust when needed, and ensure your plan always reflects your current goals and circumstances.

While business leaders are busy driving change for their companies, I help them navigate the complexities that come with executive-level equity compensation. I provide concierge-level support — from 10b5-1 trading plans to Form 144 filings, access to specialized wealth-management strategies, and personalized tax-optimization approaches. My goal is to help clients move with clarity and confidence as their financial needs evolve.
Some of my services include:

• Equity Compensation Services
• Equity Award Analysis
• Specialized Solutions

Equity awards show up in different forms, each with its own opportunities and tax considerations. I help clients clearly understand how these awards fit into their bigger financial picture — from Restricted Stock Units (RSUs) that vest over time, to Stock Options that offer potential upside, to Employee Stock Purchase Plans (ESPPs) that allow employees to buy shares at a discount. By breaking down the mechanics behind each award, I help clients make informed decisions about when to hold, sell, or diversify so their equity works in alignment with their long-term goals.

As equity awards begin to vest, taxes and timing suddenly matter a lot more than people expect. I help clients stay ahead of those moments by breaking down what happens when shares vest, how different award types are taxed, and what strategies help them keep more of what they've earned. From planning around vesting schedules to managing capital gains exposure, my goal is to turn complex tax rules into confident, actionable decisions.

When too much of someone's net worth is tied up in a single company's stock, balance becomes essential. I help clients turn concentrated equity into more diversified, resilient portfolios without losing sight of their goals.

Whether it's building a structured 10b5-1 selling plan, managing liquidity events, or aligning sales with appropriate tax considerations, I guide clients step-by-step, so they stay informed throughout the process.

Equity awards can significantly shape long-term wealth — but only if they're used strategically. I help clients explore ways to make the most of their awards today while preparing for the future, including charitable giving strategies and donor-advised funds.
My goal is to align equity decisions with the bigger financial picture, maximizing impact while mapping out what comes next.

Timing is critical — especially for executives and insiders. I help clients confidently navigate blackout periods, insider-trading policies, and pre-clearance requirements.
With structured trading plans and clear guidance, I make sure clients understand the rules, stay compliant, and keep their financial plans on track.

Equity compensation can play a meaningful role in estate and legacy planning. I help clients understand how proper planning can ensure a smooth transition of assets and protect the people they care about most. Whether it's incorporating equity into a broader wealth-transfer strategy or preparing for future generational needs, I support clients in making thoughtful, informed decisions for their loved ones.

Every client's tax situation is unique. I begin by reviewing how income, investments, and equity compensation fit together from a tax perspective. This first step helps you see where you stand - and where strategic planning can make a real difference.

Not all income is created equal. I help clients identify the best times to realize gains, exercise options, or sell shares - balancing opportunity and tax impact. With careful timing, you can stay aligned with your goals while managing exposure to higher brackets and short-term capital gains.

Equity awards can create sudden tax events that catch people off guard. I help clients anticipate these triggers - whether it's at vesting, exercise, or sale - and works alongside tax professionals to minimize surprises. My focus is on clarity, preparation, and turning complex tax rules into actionable steps.

A tax-smart investment strategy goes beyond picking the right stocks. I guide you structure your portfolio to manage gains, harvest losses when appropriate, and use tax-advantaged accounts to their full potential. The result: a portfolio that's efficient, diversified, and designed for long-term growth after taxes.

Retirement isn't just about reaching your goal - its' about knowing how to draw from it wisely. I guide clients design personalized withdrawal strategies that balance steady income, tax efficiency, and long-term sustainability. The focus is on transforming savings into a reliable income stream that supports your lifestyle and keeps your wealth working for you well into the future.

If charitable giving is part of your values, it can also be part of your tax strategy. I walk you through options like gifting appreciated stock or using donor-advised funds to maximize impact. It's about aligning generosity with efficiency, so your giving creates value in more ways than one.

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