Headsail Wealth Management

Headsail Wealth Management

Headsail Wealth Management was established in 2014 by Mark H. Miller in Oakville, Ontario. The firm operates as an independent registered portfolio manager and exempt market dealer, providing discretionary investment management for private clients, trusts, and holding companies across Canada. Miller structured the firm as a fee-only advisory, removing product commissions or trailer fees from the client relationship. The firm constructs concentrated equity and fixed-income portfolios, with a value-oriented philosophy that prioritizes capital preservation and long-term compounding. Headsail selects individual securities rather than packaged funds for client accounts, customizing allocations across Canadian and U.S. public equities, investment-grade and high-yield bonds, and cash equivalents. The firm also offers private market exposure through exempt-market offerings such as mortgage investment corporations and private real estate vehicles on a deal-by-deal basis. Client accounts are held at a third-party custodian, with Headsail retaining discretionary trading authority. Headsail remains a boutique operation serving a small number of families in the Greater Toronto Area and southern Ontario. The firm's licensed team includes registered advising and dealing representatives. In recent years, the practice has integrated tax-aware withdrawal sequencing and trust-structure planning into its investment mandates, reflecting the needs of retiring business owners who form the core of the client base. As a purely advisory firm without a corporate parent or banking affiliation, Headsail's structure removes the conflict between distribution economics and advice quality — a genuine differentiator in the Canadian wealth-management industry where most competitors still earn commission revenue. The firm's succession plan and any next-generation advisory team remain undisclosed publicly.