Comprehensive service tailored for every step of the journey

We offer seven services and write them into one plan. Estate work runs into insurance and insurance runs into tax, so you never experience them as separate disciplines.

Financial planning

This is the base everything else sits on: one written plan that covers cash flow, retirement, the kids, insurance, taxes and the estate. It is built in four steps and kept current for as long as you work with us.

  • Cash flow, savings and debt, in the order that makes the most difference.
  • Retirement projections, the accounts that fund it, and their order of use.
  • Education funding for the kids, weighed against your own retirement.
  • One document, reviewed on a fixed schedule and rewritten when life changes.

Tax planning

We read the tax return for the decisions it points to and plan the year before it ends, with your CPA. We do not prepare returns; we plan with the person who does.

  • Bracket management: what to realize, convert or defer in a given year.
  • Roth conversion timing, especially in the years before distributions begin.
  • Capital gains sequencing: what to sell, from which account, and when.
  • Tax documents sent straight to your CPA once you have introduced us.

Insurance and risk

Coverage sized to what would actually go wrong, from carriers we would trust with our own family. We are independent, so nobody tells us what to sell.

  • An audit of what you already own: gaps first, then duplicates.
  • Life and disability coverage sized to the family's real exposure.
  • Long-term care: what it would cost, who would pay, and the options in time.
  • Key-person and buy-sell funding for business owners.

For insurance, we are paid by commission from the carrier, and we show you how before you sign. Brandon Smith holds Virginia Insurance License 977146.

Estate and legacy

Documents that say what you think they say, and account titles that agree with them. We work with your attorney, or introduce you to one we have worked with for years.

  • Wills, trusts and powers of attorney reviewed against the plan.
  • Beneficiary designations and account titling, checked against the documents.
  • Gifting and charitable giving, done with the tax picture in view.
  • Your parents' documents too, before anyone needs them.

Business succession

Most of an owner's net worth sits inside the company. We plan the exit years before a buyer shows up, and for what happens to the business if something happens to you. It is the work we have done more than any other.

  • Buy-sell agreements: whether they are current, and whether they are funded.
  • Key-person coverage and deferred compensation for the people you cannot lose.
  • The company retirement plan: design, costs, oversight and benchmarking.
  • The exit itself, coordinated with your CPA, your attorney and the valuation.

Investment management

Portfolios are built from the plan, not the other way around, and run with specialist partners so planning stays our focus. Accounts are held at Fidelity and Charles Schwab.

  • Allocation set by the plan: the dates to fund, and the risk they can bear.
  • Employer stock and other concentrations, brought down deliberately.
  • Costs and holdings reviewed in the open, on the fixed schedule.
  • Third-party managers for advanced strategies, through our affiliation.

Advisory services are offered through TLG Advisors, Inc., a registered investment advisor. Advanced strategies run through that affiliation and third-party managers.

Retirement income

Once the saving is done, the questions change: which account to draw from first, when to take Social Security, what an income line does to the Medicare premium two years later. We answer them in one plan and check it every year.

  • The withdrawal order across taxable, IRA and Roth accounts.
  • Social Security timing, for each of you.
  • Medicare enrollment dates, and the income lines that raise the premium.
  • Required minimum distributions, and the Roth windows before them.

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.

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

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.

Do you prepare tax returns?

No. We plan with your CPA and send them what they need directly. If you need one, we have people we have worked with for years.

See all questions

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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