I keep thinking about a silver medal that has gone dull at the edges. Not because the race was forgettable, but because people kept picking it up. Friends. Clients. Kids who wanted to feel the weight. That is a strange object to leave on a desk in a wealth firm, and yet it explains more about good advice than most pitch decks I have sat through. If a prize only looks perfect in a case, it has not been used. The same is true of a plan that never leaves the binder.
Howland Capital Management, a Boston firm that began in 1967 as a private family office, recently landed at the top of a widely watched national ranking of advisory practices. A year earlier it sat further down the same list. Charlie Clapp, co-chair, does not talk like a man who won a spreadsheet contest. He talks like a rower. In 1984 he took silver in the men’s eight at the Los Angeles Games. The medal has tarnished. He treats that as proof, not a flaw.
What A Family Office Still Gets Right
Hard work and discipline travel well from a boat to a balance sheet. Clapp is clear about the part that matters more. A consistent group, training together and racing together, is what lets a crew finish. In his words, there is real value in all of those relationships. I have found that line more useful than any slogan about “holistic wealth.” Most families do not fail because they picked the wrong fund ticker. They fail because nobody stayed close enough to notice the quiet change: a divorce brewing, a child who will not run the business, a parent who started giving money away without telling the trustee.
The firm still behaves like a family office even after nearly sixty years. Client count has grown past 400 families, foundations, and small institutions. Assets sit around $4 billion, across more than 500 accounts. Those are not tiny numbers. They are also not the scale of a national wirehouse. The promise is that the room still feels knowable.
We take care of families, we go to weddings, we go to funerals, we get to know our clients extraordinarily well.
Charlie Clapp, on the culture he saw in Weston “Tony” Howland III
Tony Howland, co-chair and chief executive, is the son of the founder. Clapp says what appealed to him at the first meeting still holds. That is a high bar. Plenty of firms recite it. Fewer show up when the event is not a portfolio review.
Rankings Measure Scale, Clients Feel Continuity
A proprietary ranking that screens roughly a thousand firms will weigh assets, years in the business, and a stack of other metrics. Useful as a filter. Incomplete as a verdict. Appearance on a list is not a personal endorsement, and no firm should be hired because a scoreboard moved. Still, a jump from the middle of the top ten into the first seat tells you something survived scrutiny. Experience counted. So did the book of business.
Perhaps the most interesting aspect is what the medal story adds. Clapp credits the Olympic result to work, discipline, and the ability to get back up after a setback. Then he undercuts the hero narrative. The crew did it. Solo brilliance does not move an eight-man shell. Advice works the same way. The analyst, the planner, the client, the estate lawyer, the adult child who finally reads the trust document. Leave one of them out and the boat yaws.
Multigenerational Goals Need A Container
About 65 percent of client assets at the firm sit in trusts. That figure is the quiet center of the practice. A trust is not a magic tax eraser. It is a container with rules: who benefits, when, under what conditions, and who watches the trustee. Clapp’s team looks ten, twenty, sometimes thirty years out when they structure those containers. Estate transfer is slower than a trade ticket. It should be.
I have sat in meetings where a family treated the trust as paperwork for “later.” Later arrived as a hospital hallway. The document they had signed a decade earlier did not match the people in the room. A sibling had been added. A charity had been dropped. Nobody had updated the successor trustee. The long view only works if someone keeps walking it.
- Name the people, not just the percentages, before the lawyer drafts.
- Decide what “benefit” means: income, principal, education, a house, a business stake.
- Pick a trustee who can say no without blowing up Thanksgiving.
- Review the document after marriages, deaths, moves, and large liquidity events.
- Keep a plain-language summary the heirs will actually read.
None of that is glamorous. It is also where fortunes leak. A beautiful allocation cannot fix a trust that pays the wrong person.
Play The Cards On The Table
Clapp refuses the guessing game on future tax law. You can guess where lawmakers will go, he says, and it never works. The firm deals with the cards on the table. I like that restraint more than I like bold tax forecasts. Congress is a weather system. Building a plan that only works if a rate expires on a specific Tuesday is how families get surprised in April.
Current rules still leave real choices. Step-up questions. Gift timing. Charitable deductions. The difference between selling a winner and giving it away. Those choices live inside the code you can read today. If the code changes, you adjust. You do not pretend you already know the amendment.
That stance also steadies people when headlines get loud. There is always going to be something that trips the world up. The first nine months of 2026 offered a full tray: sticky inflation, war, tariffs, and the first policy-rate increase since 2023. A plan that needs calm markets is not a plan. It is a hope.
The Only Lever Is Not The Whole Machine
Wall Street spent recent weeks flinching at Treasury yields pressing multiyear highs. Traders priced more hikes because inflation refused to lie down. Clapp stays largely unbothered by the theater around the policy rate. If the central-bank chair is the Wizard of Oz, he says, the only lever in that hand is the funds rate. One dial. A large economy. Plenty of other forces moving prices, wages, and credit.
The practical response at the firm is narrower than a macro essay. Avoid highly leveraged companies. Avoid floating-rate debt that reprices against the client. Favor investments with dependable cash flow. That is not a claim that rates do not matter. It is a claim that a family should not need the Wizard to be kind in order to pay the bills.
The key is making sure you have a good, disciplined plan in place. That is what really lets you ride out the uncertainty.
Short sentence, long implication. Discipline here is not a mood. It is a rule set you can describe to a spouse without a chart.
A Retailer, A Dividend, And A Gift
Clapp points to TJX, the off-price retailer behind familiar store banners, as a long-term holding that fits the brief. Strong, repeatable cash generation has supported a rising dividend. He calls that an annual raise for clients. An investor who held the shares for roughly twenty-five years now receives dividend income that is large relative to the original outlay. Cash flow, compounding, time. The unfashionable trio.
Then the story gets specific, which is where advice stops being a slogan. Earlier this year a client gave more than $100,000 to charity by transferring 700 shares. Those shares had originally cost less than $1,800. Donating appreciated stock can sidestep a hefty capital-gains bill and still support a charitable deduction. Clapp calls the economics of philanthropy an important part of the work.
Run the contrast in your head. Sell first, pay tax, give cash. Or give the shares, let the charity sell, keep more of the economic gift in the recipient’s hands. The second path is not a loophole hack. It is ordinary, legal, and easy to miss if nobody mentions it before the sale ticket goes in. In my experience, families hear about it after they have already sold. That is the expensive order of operations.
| Path | What leaves the portfolio | Tax friction | What the gift can do |
| Sell, then donate cash | Shares converted to cash | Gain often realized first | Smaller net gift after tax |
| Donate appreciated shares | Shares transferred directly | Gain often avoided by the donor | Larger gift, deduction may apply |
| Hold and take dividends | Nothing, income arrives yearly | Dividend tax rules apply | Funds lifestyle or later gifts |
The table is a sketch, not tax advice. Basis, holding period, the charity’s status, and the client’s bracket all change the math. The point is the sequence. Decide the purpose before you create the taxable event.
Steady As It Goes Is A Strategy
Clapp describes the firm’s stance as steady as it goes. Same for the investment approach. It is important, he says, that you are not reacting to all of these different things. You are staying ahead of them. Reaction feels like work. It is often just noise with a login.
He notes a pattern that humbles forecasters. At some point in every year, the market has been down double digits and has ended up double digits. Not a promise. A reminder that the path and the destination disagree often enough to punish anyone who treats a bad month as a verdict.
A broad look at the main U.S. large-cap index puts a number on the sway. On average, the gap between the highest and lowest closes in a given year runs about 33 percent. That is not a crash statistic. It is a normal-year statistic. If your stomach requires a straight line, public markets will keep disappointing you.
A Year That Already Proved The Point
The index closed 2025 with a third straight double-digit annual gain. By March 30, 2026, it had fallen about 7 percent and finished that session at 6,344, the low of the year so far. By mid-August it had climbed almost 23 percent off that bottom and set a fresh high on August 13. As of the close on October 7, it was up nearly 14 percent for the year.
Read that again without the drama. A modest drawdown. A sharp recovery. A year that still looked fine if you only checked in October. Anyone who sold the March low to “wait for clarity” paid for the clarity with the rebound. Clarity usually arrives after the price has moved.
A simple stress check: What fell this year, and when? What did the plan require you to sell? What income still arrived? Who needed cash, and was it already set aside?
If the answers are “the market,” “nothing core,” “the dividends,” and “nobody, because the reserve was funded,” you were already ahead of the headlines. That is staying ahead, in Clapp’s sense. Not predicting the low. Not needing to.
Relationships Are An Operating System
Go back to the boat. An eight does not succeed because everyone is friends. It succeeds because roles are clear, timing is shared, and a bad stroke gets corrected without a speech. Family wealth has the same requirement, with more ego in the boat.
Weddings and funerals are not marketing lines. They are where the real balance sheet shows up. Who is in the will. Who is angry about the business. Who just inherited a house they cannot afford to keep. An advisor who only appears for the quarterly PDF will meet those facts late, when the options have narrowed.
Clapp’s Olympic crew trained as a unit. The firm tries to do a version of that with clients: one group of people who know the file, the family, and the weird exceptions. Scale fights that. Four hundred families is a lot of funerals. The discipline is deciding which relationships stay deep, and staffing so the deep ones are not a fiction on the website.
- One lead who actually knows the family story, not a rotating call center.
- A written investment policy the client can explain back.
- A cash reserve sized to spending, not to a feeling.
- Trust and estate documents reviewed on a calendar, not after a crisis.
- A giving plan that uses appreciated assets when that fits.
- A rule for what you will not own: heavy leverage, debt that floats against you.
That list is plain on purpose. Fancy language hides missing steps.
What “Family Office” Should Mean At Home
The phrase family office gets stretched until it means “we have a portal.” Originally it meant a staff that existed for one family: investments, taxes, bills, philanthropy, the odd property. Howland started that way in Boston and then opened the model to other families and small institutions. The useful remnant is intensity. Fewer clients per senior person. Longer memory. Less product push.
You do not need $4 billion to borrow the habits. A household can run a small version.
Keep one shared folder the adult children can find. Record account locations, advisors, and the password process without dumping secrets into a group text. Note why a holding exists. “Dad liked the store” is a reason. It is not a policy. Write the policy in a sentence: we own businesses that throw off cash we can spend or give, and we do not borrow against them to feel clever.
Meet once a year when nobody is sick. Cover spending, gifts, and who would step in. Twenty minutes of that meeting beats a perfect allocation you cannot explain after a bad quarter.
Cash Flow Beats A Story About Growth
The TJX example is really a lesson about dependable cash flow. A rising dividend is not exciting on a trading screen. Over twenty-five years it becomes a paycheck that did not require selling shares. Selling shares to live is fine when it is planned. It is painful when it coincides with the March low and a tuition bill.
I am not arguing that every family should own one retailer forever. Businesses change. Management changes. A moat can silt up. The filter Clapp describes is stricter than brand loyalty: can this holding keep producing cash without needing cheap debt, and can that cash support the people who actually own it?
Floating-rate exposure fails that filter when policy rates climb. The interest cost moves against you while the asset may not. Leverage fails it faster. A down year in the asset plus a fixed obligation is how “temporary” becomes a forced sale. Forced sales are where long-term investors accidentally become short-term sellers.
Philanthropy As Portfolio Design
Giving is often treated as the leftover. Whatever is left after the lifestyle and the heirs. The 700-share gift flips that. The appreciated position was the tool. The charity received a six-figure transfer. The original cost was under two thousand dollars. Time did the heavy lifting. Structure kept the tax from eating the lift.
Families who care about causes can design for that on purpose. A sleeve of long-held, low-basis shares becomes the giving inventory. New cash goes into retirement accounts or into positions you might need to sell. You do not have to love the idea of “tax alpha” to see the fit. You just have to decide the gift before the broker asks which lot to sell.
The economics of philanthropy are part of the plan, not a footnote after the markets close.
That is my wording, not a slogan from a brochure. It matches the example. A gift that large, from a cost basis that small, does not happen by accident in the week of a gala. Someone had to know the lots.
Inflation, War, Tariffs, And The Useless Urge To Narrate
2026 has been a year that invites narration. Inflation that will not fully quit. Conflict that moves energy and shipping. Tariff talk that rearranges margins. A rate hike after a long pause. Each item can support a confident essay. Together they support paralysis.
Clapp’s answer is almost rude in its simplicity. Something will always trip the world up. The defense is the plan you already funded. Spending covered. Debt limited. Cash flows you can name. Trusts that still match the family. If those are true, the narration can stay on the screen.
I have watched smart people break that rule in both directions. One camp sells everything because a headline used the word “crisis.” The other camp adds leverage because a headline used the word “soft.” Both are reactions. Neither is a policy. A policy sounds boring when you say it out loud. Good. Boring is what you want the money to be while your life stays interesting.
Questions Worth Asking Any Advisor
A ranking can start a search. It should not end one. If you are interviewing firms, including practices that sound like this Boston shop, the useful questions are specific.
- Who, by name, will know our file in three years?
- What share of client assets sits in trusts, and who coordinates the lawyers?
- How do you decide a holding is too leveraged to keep?
- Show a real charitable-lot example, with basis and holding period, not a hypothetical.
- What did you sell in the last drawdown, and why?
- How often do documents get reread when nothing is on fire?
- What will you refuse to buy even if a client asks?
Listen for answers that include names and numbers. “We are client-centric” is not an answer. “We will not own issuers that need floating-rate debt to fund ordinary operations” is an answer. You can agree or disagree. You cannot confuse it with a mood.
The Medal Test
Here is a test I now use, borrowed from that tarnished silver. Has the plan been handled? Have clients and heirs actually touched it, asked dumb questions, dropped it once, put it back? A plan that stays pristine has not been in the room. The Olympic medal looks worse than the day it was awarded. It has also done more work.
Clapp keeps it where people can pick it up. The firm he helps lead grew from one family’s office into a practice serving hundreds, without pretending the original job changed. Take care of families. Know them well enough to attend the wedding and the funeral. Structure assets so the next generation is not guessing. Ignore the urge to forecast Congress. Ignore the urge to trade every yield spike. Own cash flows. Use the appreciated shares when generosity and taxes can share a form.
You can steal that operating system without moving to Boston and without needing an Olympic story on the shelf. Write the rules. Pick the crew. Review the trusts. Leave a cash reserve that makes March irrelevant to your grocery bill. Then let the year be noisy. It will be. The index already proved it once this year, from 6,344 in late March to a high in August and a double-digit gain by early October.
Relationships are the part that does not show up cleanly in an asset-weighted ranking. They are also the part that decides whether the ranking mattered. A firm can sit at number one and still lose a family that felt unknown. A smaller practice can keep a family for three generations because someone remembered the funeral. Clapp’s crew metaphor is not soft. In a boat, a missed relationship is a missed catch. The shell slows. Everyone feels it. Wealth is less honest about the miss, until the reading of the will.
A Practical Year For A Household
If you want this to leave the page, give the next twelve months a shape. Not a new personality. A calendar.
In the first month, list every account, the owner, and the beneficiary. Beneficiaries override wills more often than people think. A stale form is a decision you already made and forgot. In the second month, pull cost basis on anything you might give away. Low-basis shares are a resource. Treat them like one. In the third month, size a spending reserve in cash or short instruments so a 7 percent dip does not force a sale. That dip already happened this year. The next one will not send a warning labeled as such.
Midyear, reread the trust summary with the person who would serve as successor. Ask them if they would actually serve. Polite yeses are not trustees. In the fall, decide gifts before you harvest gains for other reasons. December is a bad time to invent a philosophy. Early winter, write one page on what you will not own. Leverage you cannot service from cash flow belongs on that page. So does debt that resets higher while your income does not.
None of this requires a medal or a national rank. It requires the same trait Clapp credits for the silver: getting back in the boat after a bad piece. Markets will hand you a bad piece. Families will too. The plan is the crew you trained with before the race got loud.
Household rule of thumb: reserve covers spending, trusts match people, gifts use low basis, leverage stays rare.Stick that somewhere unglamorous. A notes app is fine. The point is retrieval, not design.
Why The Long Horizon Changes The Trade
Ten to thirty years is an awkward horizon for a market that reprices every afternoon. It is the right horizon for a trust that names grandchildren who are not born. Clapp’s team uses that span to guide estate and wealth-transfer choices. The investment book has to survive the span, not win the quarter.
Survival is a different optimization. You care about permanent loss more than relative rank. You care about income that can be paid without selling at a mark you hate. You care about documents that still function if the person who signed them is not in the room. A hot theme can clear the first test for a season and fail the other two. That is why “steady” is not laziness. It is a refusal to spend the family’s future on a narrative that expires.
The average 33 percent high-to-low swing inside a single year is the tax you pay for liquidity. You can refuse the tax by leaving public markets. You then take on business risk, property risk, or lockup risk instead. There is no corridor with no weather. Family-office thinking, at its best, picks the weather it can live with and builds the house accordingly.
A Note On Rank And Fit
Howland’s move to the top of that advisory list will draw calls. Some of those calls should happen. A firm with decades in one city, a trust-heavy book, and a public preference for cash-flow holdings is a coherent offer. Coherent is rare. It is not universal. A founder still building a company may need a different desk. A household with no estate complexity and a simple index habit may not need this intensity at all.
Fit is the unranked metric. If you want someone who will attend the hard days and still talk about lots and basis on the ordinary days, say so in the first meeting. If you want tactical calls on the next hike, say that too, and expect a mismatch with a practice that thinks the policy rate is one lever among many. Honesty at the start saves a messy exit later. Crews that disagree on the stroke rate do not quietly improve. They argue at the wrong moment.
I will leave the medal where Clapp left it, in the story rather than the vault. Tarnish means use. Use means the relationships were real enough to leave marks. In wealth, that is the result worth ranking, whether or not a national list agrees in a given year. Build the crew. Write the rules. Let the year swing. The families who can still explain their plan in October are the ones who were never really late.
