Building Value with Patience and Purpose
We invest in exceptional businesses and high-quality real estate assets, guided by the discipline of an operator and the perspective of a long-term owner.
Our Investment Approach
Patient Capital for Enduring Growth
We believe lasting success comes from patience, discipline, and true partnership – not short-term gains. Greyfield brings an operator’s mindset to investing, combining hands-on experience with long-term capital to build businesses and assets that thrive across market cycles.
We invest in:
- Privately held lower middle market businesses that operate in niche markets with durable competitive advantages and strong leadership.
- Institutional-quality commercial real estate delivering consistent income and long-term appreciation.
About Greyfield
Greyfield Holdings is a private investment office founded in 2019 by Brad Osleger, a seasoned entrepreneur and investor based in Winter Park, Florida. Greyfield combines patient capital with real-world operating experience to build lasting value in private companies and commercial real estate.
Brad brings an operator’s mindset to every investment. As CEO of OnSight Industries (2013—2025), he led a decade of transformative growth – expanding revenue at a compound annual growth rate above 20% and increasing annual EBITDA by more than 35x. During his tenure, OnSight earned national recognition on the Inc. 5000 list five times, reflecting the company’s consistent growth and performance. He also led multiple private equity transactions before transitioning to the role of Board Director in 2025.
Earlier in his career, Brad served as an equity analyst, grounding his approach in financial analysis and capital markets. He holds a BBA in Finance from Emory University and an MBA from Rollins College.
Building Enduring Partnerships
We value long-term relationships built on trust, alignment, and shared vision. If you share our belief in patient growth and lasting value, we’d welcome the opportunity to connect.