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

Most professionals think high-net-worth clients choose advisors based on credentials, performance, or technical brilliance.

They are wrong.

In this episode, Dave Lorenzo sits down with two of the most trusted dealmakers in the family-enterprise and advisory world, Harry Cendrowski and John Alfonsi of Cendrowski Corporate Advisors, to expose what actually drives trust, loyalty, and long-term relationships with wealthy families.

This is not a fluffy conversation about “relationship building.”

It is a behind-the-scenes look at how elite advisors operate when real money, real families, and real legacy are on the line.

You will hear why high-net-worth relationships fail when professionals approach wealthy clients as “targets” instead of human beings with emotional, generational, and identity-level stakes involved.

John explains why even a perfectly executed financial plan can collapse if you ignore the emotional side of exits, litigation, or succession. Harry reveals how trust is built not through salesmanship, but through consistency, generosity, and genuine curiosity about a client’s life, not just their balance sheet.

They also break down the invisible mechanics of elite advisory relationships, including why asking better questions beats delivering smarter answers, how to communicate complex ideas without losing credibility, and why wealthy families judge you as a reflection of themselves.

The conversation moves into generational shifts, showing how millennial and next-generation wealth holders think differently about risk, exits, and advice, and why advisors who fail to adjust will quietly be replaced by those who do.

If you work with business owners, wealthy families, or aspirational high-net-worth clients, this episode will challenge many of your assumptions about what “expertise” really means and why most advisors never get invited into the inner circle.

This is a masterclass in how real trust is built at the highest levels of the market.

Most professionals say they want high-net-worth clients.

Then they spend their time arguing with strangers on LinkedIn and building businesses that make them poor.

In this episode, Dave Lorenzo breaks down a real-world case study sparked by a financial advisor who bristled when told that Dave works with advisors serving clients with $5 million or more in investable assets .

That simple statement triggered a public social media argument that revealed two brutal truths most professionals refuse to face:

First, fighting online kills trust.

Prospective clients are watching how you behave long before they ever reach out. When you argue in public, you broadcast insecurity, not authority.

Second, targeting small clients is a business model that caps your income.

A financial advisor managing $100,000 makes $1,000 a year.

That same advisor managing $5 million makes $50,000 for roughly the same amount of work .

Same trust.

Same acquisition effort.

Wildly different return.

Dave explains why working with affluent and high-net-worth clients is not greedy. It is rational.

If you want to volunteer, do it after hours.

If you want to run a business, maximize return on your time and expertise .

In this episode you will learn:

• Why arguing on social media silently destroys your credibility
• How affluent clients think about risk differently than mass-market clients
• Why high-net-worth prospects are often easier to acquire than smaller ones
• How fee-based advisors make more money by serving fewer, better clients
• The hidden cost of being “noble” in your business model

If you are a financial advisor, attorney, CPA, or insurance professional who wants to work fewer hours, earn more, and be taken seriously by people with real money, this episode will challenge the way you think about both marketing and growth.

Stop fighting online.

Start building a business that actually pays.

Listen now.