About Us

Our Approch

• At Windfall Hill Capital, we leverage 15 years of Capital Markets and Leveraged Finance Sales and Trading experience when forming our portfolios.  We listen to the goals and objectives of each investor to tailor each individual portfolio.

• Our Asset Allocation strategy considers what will happen in the next 1 year, 3 years and 5 years. Other Advisors use backward-looking models, which leads to lower returns for clients.

• Windfall Hill Capital seeks diversification through Stocks, Corporate and Municipal Bonds, Commodities, Private Equity, Private Credit and Hedge Funds.  Most Advisors only offer access to 1 or 2 of these Asset Classes.

• We leverage sophisticated software for Financial Planning, Tax Efficient Portfolio Management and Risk Management – and the client has access to all of these tools.

• We are forward thinking investors, because the market changes every day.  We complement market-based investing with thematic sector allocations, and always invite client ideas and input into portfolio composition.  And always with full transparency.

Josh Leary is the Founder and CIO of Windfall Hill Capital, a role he has held since March 2025. With a career spanning over two decades in finance, he has extensive experience in capital markets, portfolio management and risk underwriting.

Prior to founding Windfall Hill Capital, he served as a Partner at a local Hedge Fund in Charlotte, where he focused on client relationships, portfolio management and equity valuation. His background also includes 14 years of Fixed Income Sales & Trading, earning Managing Director title in 2022.  Earlier in his career, he worked as a Liability Underwriter for Lloyd’s of London in both London and Sydney.

He holds an MBA in Finance from UNC Kenan-Flagler Business School and a BS in Business Administration from Washington and Lee University. He is also certified with Series 7 & 66 licenses from FINRA.

Windfall Hill

Nestled some 2 miles outside of college town Lexington, VA is Windfall Hill. In the Shenandoah Valley – middle of nowhere Virginia – this place is known to many W&L students and grads as a place to unwind when off campus.

College life represents the end of one journey and beginning of another. And for me, time on Windfall Hill is where education, ambition and future potential converged.

As individual journeys in life evolve, doors open and close. Investing is a way to open new doors, as many have discovered in the pursuit of their own “American Dream.” At Windfall Hill Capital, we help our clients confidently pursue their own paths and open doors for the next journey in life.