Renowned Advisor Emphasizes The Unifying Value of Client Relationships

Charlie Clapp, co-chair of Howland Capital Management — ranked No. 1 on CNBC’s Financial Advisor 100 for 2026 — knows precisely how to exceed expectations in the finance sector. Within his private workspace sits a silver medal earned in the men’s eight rowing squad at the 1984 Summer Olympics in Los Angeles; over the decades, the commemorative item has lost its luster, standing as testimony to years dedicated to managing clients and personal friendships. He credits that vintage achievement to relentless effort, disciplined practice, and the capacity to rebound from setbacks. In a corporate context, “those same attributes carry over,” Clapp states. Crucially, however, “having a consistent cadre of individuals with whom you train, compete, forms the bedrock of success. There is genuine value inherent in all of those relationships.”

‘There is always going to be something that trips the world up’

Established in 1967 as a family office based in Boston, Howland Capital Management has retained its tight-knit family-office ethos while scaling to serve more than 400 families, foundations, and small institutions after nearly six decades of operation.

“Almost everything that drew me attention initially—the same sentiment holds true today” — Clapp reflects on his father, Weston “Tony” Howland III, co-chair and chief executive. “We safeguard families, host ceremonies, participate in memorials, and build an extraordinary rapport with our clients.” The firm currently oversees $4 billion in assets managed across more than 500 accounts.

Accompanying the discussion is another image of Clapp, referencing his 1984 Olympic silver medal and accompanying patch.

Clapp outlines the strategic emphasis placed on long‑term planning within the family-office model. With multi‑generational objectives central to the firm’s mission, asset structuring through irrevocable trusts becomes paramount to meet future goals. Approximately 65 percent of client holdings reside in trusts to ensure legacy protection. Because navigating evolving legislation requires constant vigilance, the firm prioritizes working within established codes. “You may hypothesize regarding tax reforms, yet predictions seldom prove accurate,” Clapp comments on attempting to anticipate congressional moves, stressing the importance of adhering to the framework currently available. “This strategy enables the firm to support clients effectively through turbulent periods.”

‘It’s important that you are not reacting’

Recent Wall Street developments—including persistently high Texas Federal Reserve interest rates, treasury yields climbing toward multiyear peaks as investors anticipate further tightening—have added volatility to the recent stretch. Despite the climate, Clapp remains largely indifferent to fluctuating Federal Reserve policy, noting the primary tool of Fed leadership, the fed funds rate. The firm’s investment methodology focuses on sidestepping highly indebted entities reliant on floating‑rate liabilities, opting instead for allocations weighted toward companies generating predictable cash flows to sustain wealth over extended horizons.

Notably, TJX Companies, Inc. is presented as a premier example of a low‑maintenance, high‑quality holding.

Howland Capital has sustained strong, reliable profitability, allowing the discount retailer to expand its annual dividend and furnish sizable returns to early investors. One illustrative case involved a client transferring 700 shares—a former investment costing under $1,800—to generate charitable gifts exceeding $100,000 earlier this year via appreciation transfers, thereby mitigating capital gains liabilities while securing substantial tax deductions for donors.

The investment framework championed by the leaders is characterized by steadiness rather than opportunistic reaction. Whether markets experience prolonged corrections—as evidenced by the S&P 500 swinging 33 percent between yearly highs and lows—or recover swiftly, proactive positioning mitigates adverse outcomes.

According to CNBC analysis, the broader S&P 500 achieved three consecutive double‑digit annual advances in late 2025 but slipped to a summer low of 6,344 by mid‑March 2026 before rallying over twenty‑three percent to reach a record high on August 13th. As of October 7 closing, the index reported a net gain of nearly fourteen percent year‑to‑date.

— Gabriel Cortes contributed to this report.

CNBC receives no compensation from placing financial advisory firms on our Financial Advisor 100 list. Furthermore, a firm’s appearance or an advisor’s placement in this ranking constitutes no endorsement by CNBC of any individual or organization.

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