About Waypoint
Waypoint Wealth Services is an independent, fee-based financial planning firm in Chesterfield, Virginia. Brandon Smith has planned for families across Central Virginia since 2015, and Waypoint is the firm built around that work: a team of four, one written plan for every client, and the CPA and attorney you already trust working from it.
Here for the long haul
Most of our clients came to us through someone they trust, and many have been with Brandon for years. Waypoint is built to keep it that way. We are independent, so nobody tells us what to sell. We are fee-based on purpose, so we can help people a fee-only model would turn away. And we are small enough that every client knows who to call.
We plan for families and business owners with roughly one to five million to look after, the point where the pieces of a financial life start to outnumber the people minding them. The plan covers investments, taxes, insurance and the estate. It is written down once and kept current for as long as you work with us.
The name describes the job. A waypoint is the fixed point a route is plotted from. For your CPA, your attorney, your custodians and your insurance carriers, that point is us.
- Chesterfield, VirginiaBased here, meeting clients across the state
- Since 2015Planning for families in Central Virginia
- Four peopleBrandon leads every plan
- Fidelity and Charles SchwabWhere client accounts are held
Core beliefs
Money isn't a math problem. It's a behavior problem.
Most financial mistakes aren't ignorance. They're emotional decisions wearing a suit. A good plan is one you'll actually stick to when you're scared.
Margin beats optimization.
An emergency fund doesn't need to be exactly six months of expenses. It needs to exist. We've seen families hurt by gaps in a plan, never by an allocation a point off.
Independent advice is key to client success.
Being a fully independent firm means no one tells us what to sell. We recommend what fits the person across the table, and we care whether the insurance carrier is still standing when the claim comes due.
Brandon Smith, Founder
Who you'll work with
Brandon leads every plan. Three people work alongside him, and every client knows who to call.
Brandon Smith, ChFC, CLU, MBA
Founder and principal advisor
Brandon founded Waypoint to hold the whole picture for the families he serves: the plan, the taxes, the insurance and the estate, coordinated with the CPA and attorney they already have. The firm's business-owner work, succession, buy-sell agreements and key-person coverage, runs through him.
Brandon VaughanFinancial Advisor and Planning Specialist Income and asset accumulation. Brandon has worked with the practice's clients since 2021, and is often the first call for our younger families.
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Rachael SurlesDirector of Marketing and Operations The quarterly letter, the client events, and most of what you hear from us between reviews.
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Madeleine SurlesAdministrative Coordinator Scheduling, account paperwork and the follow-through between meetings. Madeleine is usually the first voice you hear when you call the office.
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Chesterfield, and across Virginia
We're based in Chesterfield, just south of Richmond, and most of our clients are in Central Virginia. Most meetings are by video. We meet in person by appointment, in Chesterfield and at offices across the state, and a permanent office is planned for January 2027.
- (804) 799-0599
- 6933 Commons Plaza, Suite 544, Chesterfield, VA 23832. Mailing address only.
- Meetings by appointment, in person or by video.
The firms we work with
Waypoint is a small firm with a long bench. These are the firms that hold your accounts, supervise our work and handle the specialist work we don't do ourselves, so you know who is behind each part of the plan.
CustodianYour accounts are held here in your name, apart from the firm, and we act in them only on your instructions.Go to Fidelity
CustodianAccounts held at Schwab are in your name and independent of the firm.Go to Charles Schwab
Broker-dealerSecurities and investment advisory services are offered through Simplicity Investments, member FINRA and SIPC. Waypoint Wealth Services is not affiliated with Simplicity Investments.Go to Simplicity Investments
Registered investment advisorOur advisory work is registered and supervised under it.Go to TLG Advisors, Inc.
Investment managementWe work with them for outsourced portfolio management, so planning stays our focus.Go to Mariner Wealth Advisors
Investment managementWe work with them for specialized portfolio management.Go to Simplicity Wealth
Estate and philanthropic planningA specialist partner for advanced trust and charitable-giving work.Go to Sterling Foundation Management
Insurance and annuity brokerageA brokerage partner for the insurance and annuity side of the plan. We work with them to design coverage and place it with the right carrier.Go to The Pinnacle Group
Insurance and annuity brokerageAn independent insurance brokerage with access to a wide range of carriers, for life, long-term care, disability and annuity work.Go to Ash Brokerage
Planning technologyWhere your plan, the tax analysis and your documents live. You log in to see your own.Go to RightCapital
Planning technologyWhere your estate documents and beneficiaries are organized and kept current.Go to Wealth.com
Listing of these firms does not constitute an endorsement of Waypoint Wealth Services by them. Check the background of this investment professional on FINRA BrokerCheck.
Common questions
Is Waypoint a new firm?
The name is newer than the practice. Brandon has planned for families in Central Virginia since 2015, and most of our clients have been with him for years. Same people, same phone number, and a firm built to be here for the long haul.
Who is Waypoint affiliated with?
Securities and investment advisory services are offered through Simplicity Investments, a securities dealer and member FINRA and SIPC, and TLG Advisors, Inc., a registered investment advisor. Waypoint Wealth Services is not affiliated with Simplicity Investments.
Where are my accounts held?
At Fidelity or Charles Schwab, in accounts in your name. We can see them and act in them on your instructions. We never hold your money ourselves.
Do I have to change my CPA or attorney?
No. If they are good, we work with them. We coordinate, we don't replace. When you need one, we have people we have worked with for years.
Do I need to be near Chesterfield?
No. Most meetings are by video. We meet in person by appointment across Virginia.
How are you paid?
A mix of asset-based fees, flat planning fees, and, for insurance, commissions from the carrier. We will show you exactly how before you sign anything. We are fee-based rather than fee-only, on purpose: it lets us help people a fee-only model would turn away.
Let's talk about where you're headed
A twenty-minute conversation to see whether Waypoint is the right fit. No paperwork, no obligation.
- One written plan across investments, taxes, insurance, and estate.
- Your CPA, attorney, and carriers all working from that plan.
- Independent. Nobody tells us what to sell this quarter.
- Regular reviews, with the deadlines tracked for you.