Chessie Advisors, LLC

Chessie Advisors is a fee-only, independent advisory firm that works primarily with individuals and families — including high-net-worth clients, trusts, pension plans, charitable organizations and small businesses — to provide financial planning and discretionary portfolio management. Its service offerings include ongoing wealth management, consultative financial planning memberships, and project- or hourly-based engagements.

The firm’s investment approach uses Modern Portfolio Theory principles with a Core + Satellite structure, combining low-cost passive/index holdings as the portfolio core with non-traditional indexing and active satellite positions to pursue incremental value; portfolios are reviewed periodically and rebalanced as needed. Chessie Advisors may engage third‑party outside managers for trade execution while retaining responsibility for investment decisions, and it bundles ongoing financial planning into its managed-account service for clients who meet its internal asset threshold.

Compared with many solo independent advisors, the firm periodically offers no-charge educational workshops on topics such as retirement strategies, college funding, estate planning and employee benefits; these sessions are presented as general education rather than sales events. The firm also maintains an affiliated tax-preparation business, operates legacy planning memberships targeted to educators, and makes available technology-based estate and self-directed planning tools — features that may appeal to clients seeking coordinated tax and educator-specific planning or do-it-yourself document support.