Who we serve

Most of our clients came to us through someone they trust, at one of five points in life. Each one calls for a different kind of attention, and this page describes what that looks like. Start with the one that sounds like you.

Business owners

Owning a business ties your family's wealth to the company: succession, buy-sell funding, and an exit taxed on its structure and timing. We help by planning the business and the family together, with your CPA and attorney, well before a buyer appears.

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A shop owner in a denim apron, arms folded, smiling toward the door of his store

Key things we keep an eye on

  • The buy-sell agreementWhether it is current, and whether it is funded.
  • Key-person coverageWho the company could not run without, and what would replace them.
  • The company retirement planIts design, its costs, and the duties that come with sponsoring it.
  • The exitIt goes best when the planning starts years before a buyer shows up.

Relevant services: business succession, insurance and risk, tax planning, estate and legacy.

What our clients have in common.

It's less about a number or a title than a way of thinking. The people we work with have come to see a financial advisor as more than someone who manages investments, and they'd rather have that kind of help than go it alone.

  • They like having a clear plan.Something in writing that gets kept up to date, rather than a new opinion every few months.
  • Their situation has grown past rules of thumb.For many of our clients that's somewhere around a million in investable assets, which tends to be where the details start to matter.
  • They value having an advisor.Not only for the investments, which are one piece of it, but for the tax return, the estate documents, the dates on the calendar, keeping their CPA and attorney in the loop, and having someone to call when life happens.

If that's not quite you yet, what we publish is free to read and use.

What every client can expect.

Whichever of the five brought you here, this part is the same.

  • A written plan, kept current.

    One document that says what we're doing and why. It changes when your life does, and it's never rebuilt from scratch.

  • Someone you know to call.

    Brandon leads every plan, and you'll know who on the team picks up. If something can't wait, it doesn't wait.

  • Reviews on a schedule.

    Set at the start and kept, so a review is never something you have to ask for. In between, you hear from us when something touches your plan.

  • The dates watched for you.

    Required distributions, Roth windows, Medicare enrollment, estate document reviews, changes in the tax law. We keep the calendar and reach out ahead of each one.

  • Your CPA and attorney in the loop.

    We send them what they need, helping ensure your advisors stay aligned and informed.

  • A letter every quarter, and a cookout every summer.

    The letter says what we're watching and why. The cookout is because we like seeing our clients somewhere other than across a desk.

Why coordinated planning matters more than ever

A short guide to what goes wrong when your CPA, attorney and advisor never talk. It applies to all five situations above. Free, no obligation.

Common waypoints.

Situations we see often, and how we'd approach them.

Business owner

Selling the business

The situation

Twenty years building the company, and a buyer at the table. The sale could set the family up for good, or hand a third of it to taxes and leave the rest sitting in cash.

How we'd approach it

We'd work with your CPA and attorney before the deal closes, not after, so the structure, the tax bill, and what happens to the proceeds are settled while there is still time to shape them.

Corporate executive

Equity compensation, piling up

The situation

Years of stock grants, options, and deferred comp have done well. Much of your future now rides on one company, and every vesting date brings a tax decision you make alone.

How we'd approach it

We'd bring the concentration down on a deliberate schedule, time the tax around your brackets, and fold the company benefits into one plan with the rest of your life.

Retired couple

Retired, and unsure how much to spend

The situation

You saved carefully for forty years and you have enough. The hard part is knowing how much you can actually spend, which account to draw from, and when to take Social Security.

How we'd approach it

We'd map the income, the withdrawal order, and the Social Security and Medicare timing into one plan, then keep the reviews on a fixed calendar so nothing is missed.

Hypothetical scenarios shown for illustration only. They do not describe actual clients or results, and are not a guarantee of future outcomes.

Common questions

What if more than one of these sounds like me?

Most people are in two at once: a business owner whose parents are getting older, an executive with young kids. It is still one plan. The situations are only where we look first.

Is it too soon to bring my parents into this?

No. The earlier we see their documents, the more choices the family has. This conversation goes better before anything is urgent, and we have had it at a lot of kitchen tables.

How much can we actually spend?

We'll work with you to project a sustainable spending level based on your personal situation and assumptions, and we'll revisit it every year. Some people find they have more room than they expected. Others need to hear the opposite, and we'll say so.

Do I have to change my CPA or attorney?

No. If they're good, we work with them. We coordinate, we don't replace. When you need one, we have people we've worked with for years.

I have about an hour a month for this. Is that enough?

Yes, if it's the right hour. We prepare, you decide, we carry it out. The meetings are on a schedule we set at the start, and you hear from us when a date matters.

Is there a minimum to get started?

Our full planning relationships tend to begin around a million in investable assets. Younger families start smaller, with one of our younger advisors, and grow into it. If it isn't the right fit yet, we'll say so, and everything we publish is free to use.

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 need to be near Chesterfield?

No. Most meetings are by video. We meet in person by appointment across Virginia.

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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.

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