Oak Street Investments

Oak Street Investments provides financial planning, ongoing investment management, and basic tax‑preparation services to individuals, small businesses, foundations, donor‑advised funds and retirement plans. Through an affiliated entity (Oak Street Capital), the firm also sponsors and advises privately offered pooled investment vehicles available to accredited investors and manages roughly $125 million in discretionary assets.

The firm’s investment approach is evidence‑based and centered on low‑cost passive core exposures (chiefly ETFs and mutual funds) with strategic tilts toward smaller‑cap, value, higher‑profitability and international equities and periodic rebalancing. Oak Street also uses select derivative strategies in separately managed accounts—such as covered calls, cash‑secured puts and protective puts—and acts as the discretionary manager for pooled vehicles whose offering documents may include performance‑based compensation.

Oak Street is notable among comparable independent advisers for combining retail advisory services with private fund sponsorship and pooled‑vehicle management through an affiliate, a structure that creates potential conflicts disclosed in its offering materials. The firm also integrates basic tax preparation into its core service offering and documents policies addressing custody, personal trading and proxy voting to manage the additional compliance considerations that arise from serving both individual clients and private funds.