Our Team

Different backgrounds.
One investment lens.

The opportunities we pursue rarely fit neatly into one discipline — so we built a team that doesn't either. Two Island brings together experience across real estate, operating companies, capital formation, transaction execution, and active ownership.

50+
Years of Family Experience
3
Generations
Mariah Monks
Mariah Monks
Real Estate · Capital Markets

Leads the firm's real estate platform — from sourcing and underwriting to execution across debt and equity — with a focus on acquisitions, asset management, and capital formation. Previously at North River Company and Guggenheim Partners.

B.A., Hamilton College
Max Monks
Max Monks
Operations · Investments

Sources, executes, and manages investments across new opportunities and the portfolio. Co-founded Keeper Bay's veterinary real estate platform, sourcing $125M+ in senior debt and $75M in equity.

B.A., Vassar; MBA, IE Business School
Brian Waterman
Brian Waterman
Legal · Partnerships

Works across investments, partnerships, and transaction execution, with a focus on deal structuring. Co-founded Keeper Bay; previously in corporate law (M&A, venture capital) and family office investing.

J.D., Columbia Law School; B.A., Vassar
Haley Israelson
Haley Israelson
Analytics · Investing

Focuses on building long-term value through disciplined selection, thoughtful structuring, and active ownership. Former CEO of ElleVet Sciences. Previously at Alliance Consumer Growth and North Atlantic Capital, investing in high-growth consumer and B2B companies.

CPA; MBA, Husson University
Sheryl Burns
Sheryl Burns
Controller · Finance

Supports financial reporting, controls, accounting, and operational discipline across the platform.

Bobby Monks
Bobby Monks
Strategic Advisor

Provides strategic guidance and mentorship, drawing on decades of experience across entrepreneurship, real estate, financing, and operating businesses.