How High-Net-Worth Investors Decide Who They Trust With Capital | 961

About this episode

The episode explores how high-net-worth investors evaluate trust and competence when deploying capital, featuring insights from Glenn Wasserman of Driftwood Capital.

In this session of the Inside BS Show, Dave Lorenzo and John Alfonsi sit down with Glenn Wasserman, CFO of Driftwood Capital, to examine how high-net-worth investors actually evaluate trust, competence, and alignment when deploying capital. Drawing on Driftwood’s experience managing billions in hospitality real estate assets, Glenn takes participants inside real investor conversations, not performance marketing. He explains why sophisticated investors focus less on headline returns and more on how numbers are constructed, how fees and incentives align, and where interests can diverge when performance falls short. The discussion moves through the behavioral hierarchy that separates advisors who attract institutional-level capital from those who remain transactional. Glenn details how high-net-worth clients challenge assumptions inside reports, request sensitivity analyses on key variables like cap rates, development costs, and hold periods, and test whether operators are proactive or reactive in volatile markets. Through real-world examples from COVID-era capital decisions, maturing debt, and market-specific risk exposure, Glenn outlines what accountability looks like when…

People in this episode

Host: Dave Lorenzo

Guest: Glenn Wasserman

Topics covered

• high-net-worth investors
• trust and competence
• capital deployment
• real estate
• investor behavior
• accountability
• market risk

Keywords

• high-net-worth investors
• trust
• capital deployment
• real estate
• investor behavior
• accountability
• market risk

Mentioned in this episode

Organizations: Driftwood Capital