Oak Stone Capital LLC

Asset types: Fund · Geographic focus: United States · Assets under management: 7500000 · Years in business: 2 · Average hold period: 1 years · Employees: 5

Brian Bailey is the CEO and Co-Chief Investment Officer of Oak Stone Capital, where he leads the firm’s investment strategy across real estate and insurance-linked assets. With more than 20 years of experience in private equity, structured finance, and capital markets, Brian has built a career focused on identifying high-conviction opportunities and designing institutional-quality vehicles for accredited investors. Prior to founding Oak Stone, he served as Chief Investment Officer of a publicly traded platform specializing in insurance-related credit strategies, overseeing the deployment of capital across complex asset classes with a focus on risk-adjusted performance and capital preservation. At Oak Stone, Brian applies a disciplined, execution-oriented approach to real estate investment, leading the firm’s vertically integrated development strategy. He is instrumental in structuring offerings like the Oak Stone Development Fund I LP, which targets short-duration residential redevelopment in high-barrier Texas submarkets. Brian is known for combining strategic insight with operational rigor, ensuring that each investment opportunity aligns closely with the firm’s core philosophy: protect principal, align incentives, and outperform conventional benchmarks.