Brandon Smith

Founder and principal advisor of Waypoint Wealth Services. Brandon has planned for families in Central Virginia since 2015, and he leads every plan the firm writes. He means to be the advisor who still takes your call in year eleven.

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Brandon Smith, ChFC, CLU, MBA, Founder and principal advisor at Waypoint Wealth Services
Brandon Smith, ChFC, CLU, MBAFounder and principal advisor

Where he comes from

Brandon grew up in a family of immigrants and entrepreneurs, where starting over and building something from nothing was not a special story. It was what people did. His father was a Treasury Special Agent, so he learned early how money actually moves and what happens when systems fail.

He was fifteen during the 2008 crisis. He watched people he loved lose homes, retirement accounts and years of their lives to what basic planning could have prevented. What stayed with him was not the size of the crisis. It was that nobody in his family, and almost nobody he knew, had a financial advisor. They did not know the job existed.

He started in the industry at twenty-two and has spent the years since working out what actually helps people and what does not. He founded Waypoint to close the gap he saw at fifteen. Before any of it he was an Eagle Scout, which explains more about how he plans than any credential does.

Committed to our clients

One of Brandon's clients had built the family's house with his own hands in his thirties. He laid the floors, put in the trim and planted the trees. He died in his seventies, and about a year and a half later Brandon drove out to see his widow for a review. He knew from the driveway that something was wrong. The yard was overgrown and the roof was carpeted with leaves. She met him at the door with a towel around her neck and said the air conditioning had been out for a few days. It was August in Central Virginia. It had been out all summer, and she had not told anyone.

He called an electrician he trusts, who came within the hour. Then, over the next year, he worked with her, her family, a realtor and a facility nearby until she made the call to move herself, clear-eyed about it.

That is the job. The plan, the investments, the tax and estate work are the essentials, the part every client should take for granted. What sets Waypoint apart is the care above them: being genuinely in a client's corner, with the steadiness to carry a family through something they were not prepared for. It is the standard Brandon holds his whole team to. Not warmth as decoration. Warmth because it's true.

Five seedlings in rich soil, each a little taller than the one before

Meet with Brandon

20 minute consultation

Every relationship starts the same way: a twenty-minute conversation by phone or video, with no paperwork and no obligation. Brandon is checking fit in both directions, whether your situation matches what the firm does well and whether you want to work this way. Half the value of that conversation is an honest no. When it is no, he says so and points you toward someone who fits.

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Common questions

Who will I actually work with?

Brandon leads every plan, with the Waypoint team alongside him, and every client knows who to call.

What happens if Brandon is not available when something comes up?

Brandon Vaughan works alongside him on every plan, and the plan itself is written down where the team, your CPA and your attorney can read it. Anything time-sensitive, a death claim, a distribution deadline, an emergency, is handled the same day, whoever picks up. That line does not move.

Is Brandon taking on new clients?

A few at a time, and mostly by referral. The firm's first job in 2026 is the families already here, so Brandon takes on a new relationship when the fit is clear and there is room to do the work properly.

What happens in the first conversation?

Twenty minutes, no paperwork. We ask what is going on and tell you honestly whether we are a fit. Sometimes the answer is no, and we will say so.

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.

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.

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