Private Investment Office

Patient capital.
Operator's conviction.

Greyfield Holdings deploys long-term capital into exceptional private companies and high-quality commercial real estate—guided by the discipline of an operator and the perspective of a permanent owner.

Our Approach
2019
Founded
2
Asset Classes
Long-Term
Investment Horizon
Our Philosophy

Built to own,
not to trade

We invest in exceptional businesses and high-quality real estate with the mindset of a permanent owner. Lasting success comes from patience, discipline, and genuine partnership—not short-term financial engineering.

01

Operator's Lens

Every investment is evaluated through the eyes of someone who has built and scaled a business firsthand. We understand the realities behind the numbers.

02

Patient Capital

We are not constrained by fund timelines or exit pressures. Our permanent capital structure allows us to hold assets through full value-creation cycles.

03

Concentrated Conviction

We pursue a select number of high-quality opportunities rather than diversifying broadly. Deep knowledge of each investment drives better outcomes.

04

True Partnership

We align ourselves fully with the founders and management teams we back. Our capital comes with operational experience, not interference.

Investment Focus

Two strategies.
One standard.

We concentrate our capital in two areas where hands-on experience and long-term commitment create a durable edge.

Private Companies

We invest in established, profitable businesses operating in niche markets with sustainable competitive advantages. We seek companies where our operational perspective can accelerate growth and compound value over time.

  • Niche market leaders with defensible positions
  • Proven profitability and strong unit economics
  • Founder or management-led businesses
  • Flexible deal structures and hold periods

Commercial Real Estate

We acquire and manage durable, cash-yielding commercial real estate assets positioned for consistent income generation and long-term capital appreciation across market cycles.

  • Income-producing commercial properties
  • Markets with favorable supply-demand dynamics
  • Value-add and stabilized asset profiles
  • Emphasis on durable cash yield
Brad Osleger, Founder and Principal of Greyfield Holdings
Leadership
Brad Osleger
Founder & Principal

Brad founded Greyfield Holdings in 2019 to apply the principles he refined over a decade of building and scaling OnSight Industries. As CEO from 2013 to 2025, he led transformative growth—compounding revenue at an annual rate above 20% and increasing annual EBITDA by more than 35x. He successfully navigated multiple private equity transactions before transitioning to the Board of Directors in 2025.

That operating experience shapes every aspect of how Greyfield evaluates and supports its investments. Brad brings a builder's perspective to capital allocation—focused on the fundamentals that drive long-term enterprise value rather than short-term financial metrics.

Education
BBA, Finance — Emory University
MBA — Rollins College
Based In
Winter Park, Florida
Get In Touch

Let's start
a conversation

Whether you're a founder exploring a partnership, a broker with an off-market opportunity, or a professional seeking to connect—we welcome the conversation.

info@greyfieldholdings.com

Office

Winter Park, Florida

Inquiries

We review every inquiry personally.
Please allow a few business days for a response.

For Founders & Operators

If you're building something exceptional and seeking a long-term capital partner who understands the realities of operating a business, we'd like to hear from you.