The Waypoint Way
We build one written plan in four steps and keep it current for as long as you work with us. It starts with a twenty-minute conversation: no paperwork, no obligation, and an honest answer about whether we are the right fit.
Why the same four steps, every time
Most of what goes wrong in a financial life is not a bad decision. It is a good decision made out of order: a Roth conversion before anyone checked the Medicare premium, a policy bought before the estate documents were read.
The four steps keep the order straight: where you stand, where you are going, then the plan, then the plan kept current. One fixed point the rest of your financial life is plotted from.
Step 1. Get our bearings
- The full picture: accounts, income, the last tax return, insurance policies, estate documents, and what you are actually worried about.
- It is a conversation, not an intake form. We ask the questions and take the notes.
- This is when you send one email introducing us to your CPA and your attorney. We take it from there.
Step 2. Set your waypoints
- The points we plan toward: retirement, the sale of the business, the kids' education, a parent who will need care.
- Some are dates and some are decisions. We put them in order, so the plan knows which comes first.
- Each one is written down with a year beside it, so when the plan is done you can see which waypoint every recommendation serves.
Step 3. Chart the route
- We review the portfolio, audit the insurance, read the tax return and the estate documents, and check the timing on Social Security.
- Then we write one plan that covers all of it: investments, taxes, insurance and the estate in one document.
- You will understand every recommendation before anything is signed. If you could not explain it to your spouse, we are not done.
Step 4. Proceed and adjust
- We put the plan to work with everyone involved: the custodians, the insurance carriers, and the CPA and attorney you introduced us to.
- Reviews on a fixed schedule we agree to at the start, and a call from us when something changes that touches your plan.
- Between reviews we watch the calendar: required distributions, Roth windows, Medicare enrollment, tax law changes, estate document reviews and beneficiary titling.
Work with Brandon and his team
During the 2008 financial crisis, Brandon watched people he loved lose homes and years of their lives to what basic planning could have prevented. He was fifteen, and nobody he knew had a financial advisor. He has spent his career closing that gap, and founded Waypoint after eleven years in the industry. Before any of it he was an Eagle Scout, which explains more about how he plans than any credential does.

Common questions
Do you have a minimum?
Our planning relationships tend to start around one million in investable assets, because that is about where complexity becomes the real risk. If you are not there yet, read what we publish, use it freely, and talk to one of our younger advisors if you would like a head start.
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 need to be near Chesterfield?
No. Most meetings are by video. We meet in person by appointment across Virginia.
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.
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.
Who will I actually work with?
Brandon leads every plan, with the Waypoint team alongside him, and every client knows who to call.
What do I walk away with?
One written plan that covers investments, taxes, insurance and the estate, with every recommendation explained before anything is signed. After that, reviews on a fixed schedule and the deadlines tracked for you.
How often do we meet?
On a fixed schedule we agree to at the start, and whenever a deadline we track for you comes up. You also hear from us when something changes that touches your plan.
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.