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Annapolis, MD
8 years
CERTIFIED FINANCIAL PLANNER™
I believe financial planning should feel like a breath of fresh air. It’s about building trust, creating real connections, and working together to support what matters most to you. I love walking alongside people through life’s biggest moments, helping them feel supported and empowered as their lives and goals evolve.
I went to the University of Michigan on a Navy ROTC scholarship where I was preparing to commission as a naval officer. A medical separation in my senior year changed that direction, but not my desire to serve. That eventually led me to financial planning, where I’ve found deep purpose in being a steady partner through the transitions, decisions, and milestones that shape your life.
Your finances touch nearly every part of your life, but money itself isn’t the goal. It’s what you do with it that truly matters. That’s why I focus on building a plan that’s rooted in your values, gives you clarity, and can grow with you over time. Whether you’re preparing for retirement, exploring charitable strategies, or navigating legacy goals, my job is to make sure you feel seen, supported, and empowered to make thoughtful decisions aligned with your values.
I was born and raised in Michigan and have always felt most at home near the water. Thanks to my husband’s Navy career, we’ve lived all over the country and now call Annapolis, Maryland home. When I’m not working, you’ll likely find me with my dogs out by the water, on a yoga mat, or at a local coffee shop planning our next adventure.
You’ve worked hard to build a meaningful life. Let’s create a plan that protects it and honors what matters most to you. If that sounds like the kind of partnership you’re looking for, I’d love to connect.
Team Oak symbolizes strength, potential, and quiet confidence. With a structure built to endure and branches ready to grow, Oak brings thoughtful energy and balanced support to clients and colleagues alike.
At Root, teams are designed to deliver exceptional client care through structure, support, and collaboration. Each includes a team of Lead Advisors, Associates, and Client Service professionals—guided by a Senior Advisor to provide insight and mentorship. Clients get the benefit of a dedicated relationship, backed by a well-rounded team working together toward shared success.
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Once you start working with Root, you’ll have a kickoff meeting where we dive deep into your goals, values, and current financial picture. From there, we begin building a personalized plan through a series of focused meetings—covering income, investments, taxes, estate planning, and more—designed to help you live the life you want, not just the one you can get by on. Planning continues with ongoing support and regular check-ins to keep your strategy aligned as life evolves.
Watch (04:05)Your money is typically held at Charles Schwab, an independent custodian—think of it like a secure grocery cart where you own everything inside. The accounts stay in your name, and we act as your advisor with limited authority to manage them on your behalf. We don’t work for Schwab or earn commissions, so every recommendation we make is in your best interest.
Watch (00:50)Transferring your investment accounts is simple and secure thanks to the ACAT system, which moves assets “in-kind”—meaning nothing is sold or changed during the transfer. Whether you’re moving an IRA or brokerage account, your investments stay exactly the same; the only difference is where you log in. We don’t make any changes to your portfolio until you approve a personalized plan built around your goals and tax strategy.
Transferring your investment accounts is simple and secure thanks to the ACAT system, which moves assets “in-kind”—meaning nothing is sold or changed during the transfer. Whether you’re moving an IRA or brokerage account, your investments stay exactly the same; the only difference is where you log in. We don’t make any changes to your portfolio until you approve a personalized plan built around your goals and tax strategy.
Watch (02:02)We charge a transparent, tiered percentage based on the assets we actively manage—starting at 1% for the first $1 million and decreasing as your assets grow. There are no commissions, hidden fees, or extra charges for tax or estate planning, and billing is done monthly for flexibility. If we’re not delivering value that exceeds the cost, you’re free to walk away—no long-term commitments.
Watch (02:55)Our fee reflects the value of having a trusted partner focused on your entire financial life—so you don’t have to become your own advisor. We provide both quantifiable benefits (like tax strategies and withdrawal planning) and priceless peace of mind, helping you make confident, intentional decisions about retirement, lifestyle, and legacy. Ultimately, you’re investing in your time, clarity, and confidence—not just spreadsheets and returns.
Watch (03:18)No—James and Ari don’t personally oversee every client, but every plan follows the same high standards they’ve set through our structured team approach. Each client is supported by a dedicated team including a lead advisor, senior advisor, associate advisor, and client service associate—all trained through Root’s internal program to deliver a consistent, personalized experience rooted in our philosophy.
Watch (02:24)At Root, we focus on proactive tax planning, not tax preparation. We help clients identify opportunities like Roth conversions, tax gain/loss harvesting, charitable strategies, and optimizing income to manage healthcare costs or subsidies—all in coordination with your broader financial goals. While we don’t file your taxes, we collaborate closely with your CPA to ensure everything is implemented smoothly and strategically.
Watch (03:05)We work with people from all walks of life. Most of the people we serve have built portfolios of at least $1 million (excluding current 401(k)s if under age 59.5, real estate, and 529 plans) and are ready to delegate. We ask to manage all assets that are available for direct management so we can deliver advice that’s fully integrated across your financial life.
All advisory relationships are subject to a $10,000 minimum annual fee. If your fees under our standard asset-based schedule fall below that amount, the minimum will be applied. This structure is designed for standard advisory relationships where assets are limited but planning needs fall within our typical scope.
If your situation involves more complexity, such as business ownership, multiple entities, or advanced planning needs, and asset-based billing isn’t available, we may instead recommend working together under a flat-fee planning arrangement that reflects the scope of work involved. In those cases, a separate agreement would outline the services and cost.
If we’re not the right fit, we’ll do our best to answer your questions and connect you with someone who might be.
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Naomi Roy, CFP®
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Harry Sommers, CFP®, MBA, FBS®, CEPA®
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Katie Villegas, CFP®
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Steven Murphy, CFP®
Lead Financial Advisor
JJ Lester, CFP®, MSM
Lead Financial Advisor
JT Trimble, CEPA®, CFP®️
Lead Financial Advisor
Brett Grau MBA, CFP®, CPWA®, Charter SRI Counselor™
Lead Financial Advisor
Kerri Allen, CFP®, EA, MBA
Lead Financial Advisor
Brennen Ramos, CFP®
Lead Financial Advisor
Roch Monnig, CFP®
Lead Financial Advisor