As markets wobble amid inflation, geopolitical tensions and fresh Federal Reserve action, one Boston-based wealth manager is leaning on long-term planning and close client relationships to steady the ride. Howland Capital Management, a firm rooted in family-office traditions, is using trusts, conservative holdings and disciplined advice to protect multigenerational wealth through 2026’s turbulence.
Charlie Clapp, co-chair of the firm and a former Olympic silver medalist, says the same traits that drove him in sport — persistence, teamwork and routine — shape how his team advises families and foundations today.
From an Olympic podium to multigenerational planning
Clapp keeps his 1984 Los Angeles silver medal in his home office as a reminder of endurance and teamwork. That mindset, he says, translates into the firm’s client work: staying steady through setbacks and building long-term relationships.
Howland Capital Management was founded in 1967 as a Boston family office and has kept a close-knit, service-oriented culture even as it grew. The firm now manages about $4 billion across more than 500 accounts, serving roughly 400 families, foundations and small institutions.
Co-chair and CEO Weston “Tony” Howland III — son of the founder — and his colleagues prioritize personal involvement: attending life events, understanding family dynamics and tailoring plans to carry wealth across generations.
Practical rules for uncertain markets
Rather than chasing tax-law predictions or reacting to every headline, Howland builds plans around current rules and conservative portfolio construction. About 65% of client assets sit inside trusts, reflecting a long view on estate and wealth transfer that often spans a decade or more.
“You can guess where Congress will go, and it rarely plays out,” Clapp says. The firm instead focuses on what it can control: asset structure, liquidity and predictable cash flows.
Clapp points out that the first nine months of 2026 brought renewed market shocks — higher inflation readings, conflicts abroad, tariff moves and the Fed’s first rate increase since 2023. His message to clients: a solid plan helps you weather disruption.
Investment habits: steady, conservative, cash-focused
Howland avoids highly leveraged businesses and floating-rate debt. The firm favors companies that consistently generate cash and can support dividends — traits that matter during rate cycles and heightened volatility.
One holding Clapp highlights is TJX Companies, a retail name that has produced steady cash and growing dividends over time. For long-term holders, that income becomes a meaningful part of total return.
- Asset structuring: heavy use of trusts to preserve wealth across generations
- Conservative selections: low leverage, emphasis on cash-generating firms
- Tax-aware giving: using appreciated stock donations to reduce capital gains and amplify charitable impact
- Behavioral discipline: avoid knee-jerk reactions to short-term market moves
Clapp shared a concrete outcome of that approach: a client donated 700 shares of a long-held stock this year, generating a charitable gift of more than $100,000 while largely avoiding capital gains tax because the shares had been acquired for under $1,800. That example underlines the practical benefits of combining patient ownership with thoughtful tax and estate planning.
Why this matters now
Market swings have been dramatic in 2026: the S&P 500 slipped roughly 7% through March 30, then climbed nearly 23% from that low by mid-August and reached a fresh high on Aug. 13. As of Oct. 7, the index was up about 14% year to date. Those swings illustrate a core point of Howland’s playbook — volatility is frequent, but long-term discipline can produce durable results.
“There is always going to be something that trips the world up,” Clapp says. The distinguishing factor, he argues, is preparation: a clear plan, sensible asset allocation and relationships that allow advisors to act calmly when markets surprise.
For families planning decades ahead, that combination of personal attention and conservative investing — anchored by trusts and steady cash-flow businesses — is how one established firm aims to keep clients on track through an unpredictable 2026 and beyond.
Gabriel Cortes contributed to this report.
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Jordan Keller specializes in analyzing the US financial markets. With concrete recommendations, he helps you secure and boost your investments by providing strategies that adapt to market fluctuations.