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A Fee-only, Independent financial advisor

Let Us Be Your Trusted Advisor So You Can Focus On Life's Other Priorities

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Our goal is to be your one-stop source for all matters that concern your financial life. We know you would rather be spending time with family and friends than worrying about your finances.


Who you work with matters. We work with you in a fiduciary capacity at all times and with every type of account. That isn’t the case with most other advisors.


How your advisor gets paid matters. We only get paid by you. We do not accept commissions or fees from any third parties.

Long-Term Focus

How you invest matters. We don’t believe that markets can be timed. We focus on low-cost, tax-efficient, well diversified investments.

Experienced Advisors

Providing Personalized Experiences

Who We Are

Woodside Wealth Management is made up of dedicated, experienced and credentialed financial advisors who provide top-notch client services and expert advice to individuals, families, and businesses. We have decades of experience in the Financial Planning and Wealth Management industry, and our lead advisors are all CERTIFIED FINANCIAL PLANNER TM professionals.

Our Team

Cheryl A. Costa, MBA, CFP® Photo

Cheryl A. Costa, MBA, CFP®

Founder & Principal
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Cheryl A. Costa, MBA, CFP®

Founder & Principal

Cheryl is the Founder & Principal of Woodside Wealth Management LLC.  She began her career in financial planning and investment management in the late ‘90s after graduating from Worcester Polytechnic Institute and working as an information security engineer for the MITRE Corporation.  She holds a Master’s degree in Business Administration from Boston University and is a CERTIFIED FINANCIAL PLANNER™. 

Cheryl has over two decades of experience advising clients in all areas of wealth management and her specialty is helping retirees and almost-retirees develop a financial plan that assures that income is available for a retirement that may span multiple decades.  As a proud WPI grad, Cheryl also enjoys working with clients in the tech and pharmaceutical industries and she has a niche working with women in those industries.

Cheryl is committed to the fee-only comprehensive planning model and she has been a member of the National Association of Personal Financial Advisors (NAPFA) since 2002.  She served on NAPFA’s Northeast Region Board from 2005 through 2010 and she served on NAPFA’s National Board from 2012 through 2015.

Cheryl is also very active with the CFP® Board and served as a CFP® Board Ambassador from 2015-2023.  In addition, she served as a member of the CFP® Board’s Disciplinary and Ethics Commission (DEC) from 2014-2018, and again from 2020-2022.

Cheryl wrote the “Managing Your Money” blog for the Boston Globe for several years and has been quoted multiple times in the Wall Street Journal and the New York Times.

Away from work Cheryl enjoys her rowing machine, yoga, beach walking and reading a ridiculous number of finance books.

Matthew Costa, CFP® Photo

Matthew Costa, CFP®

Co-Founder & Senior Financial Advisor
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Matthew Costa, MBA, CFP®

Co-Founder and senior Financial Advisor

Matt is a Founder and Senior Financial Advisor with Woodside Wealth Management. He has over 8 years of experience working with his clients to craft tailored financial strategies to help them meet their needs and aspirations. Matt has a passion for demystifying complex financial topics for his clients to help them gain the confidence and clarity to make decisions that will set them up for future success. Whether you are just starting your financial journey, planning for a major life event, or looking ahead to retirement, Matt offers comprehensive guidance tailored to your individual needs, and he values building long-lasting relationships with his clients.

In addition to his hands-on experience, Matt has an extensive educational background in the areas of Finance and Business. He received his Master of Business Administration degree from New York University's Stern School of Business, with a specialization in Financial Instruments and Markets. He is also a Cum Laude graduate of Boston University's Questrom School of Business, where he had a concentration in Finance and a minor in Economics. He has been a Certified Financial PlannerTM certificant since 2018 and also has a Certificate in Financial Planning from Bryant University.

Miriam Miller Photo

Miriam Miller

Client Services Administrator
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Miriam Miller

Client Services Administrator

Miriam graduated from Bentley University with a Bachelors Degree in Economics and Finance and an Associates degree in Management. Previously, she was employed by Berkshire Mortgage Finance in Boston for 13 years where she worked as the firm's Mortgage Loan Closing Manager and as a Commercial Mortgage Underwriter for Multifamily Projects. Miriam has great attention to detail and a keen interest in the field of personal financial management.

See what we can do for you

Wealth Management You Can Trust

What We Do

Woodside is different from most wealth management firms. When we work with clients, we devote a lot of time and energy to getting to know them personally and to identifying their specific financial goals. We do this because we feel that this information is crucial to designing portfolios that will “work” for them– portfolios that they will have confidence in and will stay with when times are good and when times are not so good. Here is how that process works:


First, we will gather data in order to identify where you are now and where you want to be in the future. We then analyze your financial situation and develop a baseline plan and asset allocation plan using goals and assumptions we mutually agree upon and then determine what steps need to be taken.


Next, we will make specific recommendations to help put your plan in motion. We will open accounts, and ensure you have a properly diversified portfolio. We will likely meet several times over the first year of our relationship to ensure everything goes according to plan.


Once your plan has been implemented we continually monitor your progress towards achieving your goals and we meet with you regularly to ensure that you are meeting all of your financial commitments. Our goal is to partner with you for decades, not just years.

A little more about us

Frequently Asked Questions

Woodside is a fee-only Registered Investment Advisory firm and, as such, we are compensated only by our clients. We do not accept commissions and we do not pay or receive referral fees of any kind. In fact, there are no third party payments at all that would color our investment or planning advice.

In addition, it is important to note that when we work with clients, we are acting in a fiduciary capacity and are held to a fiduciary standard. This means that we have a duty to put our client’s interests first. Many people think all advisors are held to a fiduciary standard but the majority of “financial advisors” are held only to a suitability standard, which means that their only obligation is only to suggest investments that are suitable, which is a much lower standard.

It is also important to note that when we work with clients, we are always working in a fiduciary capacity. Other firms may reference a fiduciary standard in their literature or on their website but may only be a fiduciary in certain instances or when working with certain types of accounts.  Ask any advisor you are thinking of retaining if they act as a fiduciary at all times and with all types of accounts.

Our goal as a firm is to create a deep and long-lasting relationship with each client. For that reason, we work with the vast majority of our clients on an ongoing, AUM-fee based relationship. We believe that this is the best way for us to create a bond with our clients and help them best reach their goals. As a Wealth Management client of our firm, you will receive comprehensive financial planning services and continuous management of your portfolio. We believe that comprehensive planning is critical to the investment management process, so we do not charge Wealth Management clients extra for our financial planning services.

Occasionally we have the capacity to take on a limited number of planning only client engagements. These engagements do not involve ongoing asset management. We can work with planning-only clients on a specific targeted area of concern or work with them to create a comprehensive plan covering investment strategies and allocation, college planning, retirement planning, tax planning, and a review of insurance policies and estate documents. These standalone planning services are quoted on a fixed price basis and the cost is determined by the complexity of the planning work. 

Our portfolios are specifically designed for each client. Just as no two clients are the same, no two portfolios are exactly the same either. Our goal when designing a portfolio for a client is not to maximize short term returns. Rather, our goal is to design a portfolio that will enable a client to meet their specific, long range goals. We never use portfolio models or try and fit our clients into a one-size-fits-all allocation. Our definition of the optimal portfolio is one that a client can stay with in good times and bad.

We have been an approved provider of Dimensional Fund Advisors’ fund lineup for over twenty years. These funds are only available to advisors and financial institutions because Dimensional aims to limit volatility and attract investors that share their investment philosophy. The core tenants of Dimensional’s fund lineup include: Markets are efficient and securities are fairly priced given all publicly available information, Small Cap stocks and Value stocks outperform the market as a whole over the long-term, and funds can capture value over indexes by implementing patient buying and selling strategies when prices are volatile.

Our investment strategy is closely aligned with Dimensional Fund Advisors. We do not believe that investment managers can pick and choose stocks which will outperform the market over the long-term, so we invest the vast majority of our AUM in index based, well-diversified mutual funds. These funds have the added benefits of being low cost, since we use advisor- or institutional-class funds which have no load fees and lower expense ratios than funds available to the general public. Once our clients’ portfolios are allocated, we rebalance them yearly to account for any price movements which may have occurred and, if appropriate, capture tax losses available to offset taxable gains.

In the first year that we work together, we will meet several times. Once our relationship is firmly established we meet with clients on whatever schedule works best for them. For clients who are busy raising families and juggling multiple commitments, annual meetings are often sufficient. For retirees, we often meet quarterly or semi-annually. The frequency of meetings is entirely dependent on your needs, if something changes in your financial life or you have a question of any kind, come on in and discuss it with us.

Ready to get started?

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Contact Us

Our website contains a lot of great information, but it is no substitute for a face to face meeting. If it seems like our firm is a good match for you, we encourage you to call our office and schedule a complimentary “get acquainted” meeting. This meeting typically lasts 45 minutes to an hour. During this meeting, we want to hear more about you and what you are looking for in a trusted advisor. We will also tell you more about our firm and the services that we provide.