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 performance underwhelms. He also explores the role of courage, both on the investor side, when family offices must make unpopular allocation decisions, and on the operator side, when firms must disclose bad news early and transparently.

The session closes with a broader look at empathy and alignment in long-term capital relationships, including how Driftwood has handled investor liquidity needs during personal crises and market dislocations, even when it came at a direct cost to the firm.

This episode offers a practical, research-backed view into how high-net-worth investors think, what they listen for in advisory relationships, and why behavior, not credentials, ultimately determines who is trusted with significant capital