From observing ultra-wealthy clients snap fingers at waitstaff, weaponize inheritances against family, and introduce themselves by their net worth rather than their names, I learned that money amplifies who you already are—and for many, that revelation was uglier than any market crash I witnessed.
I'll never forget the morning I sat across from a client worth $50 million who spent our entire meeting berating the restaurant server who brought us coffee.
Seven years in private wealth management taught me many things, but perhaps the most valuable lesson was this: having money and having class are two completely different things. During my time managing portfolios for ultra-high-net-worth individuals, I witnessed behaviors that ranged from inspiring to absolutely cringe-worthy.
After nearly two decades in finance, I thought I'd seen it all. But working closely with the wealthy gave me a front-row seat to habits and mindsets that left lasting impressions, mostly negative ones. While some clients demonstrated genuine wisdom about wealth, others showed me exactly what not to do, no matter how much money I might accumulate.
Looking back now, years after leaving that world behind for writing, I realize these observations shaped my entire philosophy about money, success, and what really matters. Here are seven things my richest clients did that I'll never forget, and more importantly, never repeat.
1. They constantly reminded everyone how much things cost
You know that person who can't mention their watch without adding "It's a $30,000 Rolex"? I had dozens of clients like this. Every conversation somehow circled back to price tags.
One client couldn't introduce his wife without mentioning her engagement ring cost more than most people's houses. Another would literally pull out receipts to show people how much he'd spent on dinner the night before. The constant need to attach dollar signs to everything screamed insecurity, not success.
Here's what I learned: truly confident people don't need to announce their wealth. It speaks for itself through quiet quality, not loud proclamations. When you feel compelled to tell everyone what you paid for something, you're not sharing joy about the item itself. You're desperately seeking validation through your spending power.
The most respected wealthy individuals I met? They never mentioned prices unless directly asked, and even then, they'd often deflect or downplay the cost.
2. They treated service workers like they were invisible
Nothing revealed character faster than watching how my clients treated waitstaff, drivers, cleaners, and assistants. Some of the wealthiest people I worked with acted like service workers didn't exist as human beings.
I watched clients snap their fingers at servers, refuse to make eye contact with their drivers, and talk about personal financial details on the phone while housekeepers cleaned around them, as if these workers couldn't hear or didn't matter. One particularly memorable client would actually put his hand up in a "stop" gesture if any service person tried to speak to him directly.
This behavior horrified me because I'd grown up in a working-class family. My mother cleaned houses. My father worked in a factory. Watching wealthy clients dismiss people doing honest work felt like they were dismissing my own family.
Warren Buffett once said, "Someone is sitting in the shade today because someone planted a tree a long time ago." Every successful person got there with help from others, including those in service roles. Forgetting this basic humanity just because your bank account grows? That's a poverty of spirit money can't fix.
3. They let money destroy their closest relationships
During my years in wealth management, I witnessed more family destructions than I can count. Siblings who hadn't spoken in decades over inheritance disputes. Parents who used money to control adult children. Spouses who stayed in miserable marriages purely for financial security.
One client hadn't seen his grandchildren in five years because of a business dispute with his son. Another changed her will monthly based on which family member had pleased or annoyed her most recently. I sat through meeting after meeting where money was weaponized against loved ones.
The 2008 financial crisis showed me how quickly fortunes can disappear, but family disputes over money? Those wounds last generations. I watched portfolios recover much faster than relationships ever did.
What good is having millions if you're eating dinner alone every night because money has poisoned every meaningful relationship in your life?
4. They never had "enough"
Here's something that might surprise you: some of my wealthiest clients were the most anxious about money. Clients with $10 million worried they'd run out. Those with $50 million envied those with $100 million. The goalpost constantly moved.
I had one client who tracked his net worth daily, sometimes hourly. Market fluctuations that wouldn't impact his lifestyle at all would send him into genuine panic. Another client, despite having generational wealth, shopped exclusively with coupons and complained about the cost of everything from groceries to his country club dues.
This scarcity mindset despite abundance taught me that if you can't feel secure with millions, you have an internal problem that money will never solve. The question isn't really "How much is enough?" but rather "Why do I never feel secure?" That's inner work, not portfolio management.
5. They confused net worth with self-worth
Too many clients introduced themselves by their financial achievements before anything else. "I sold my company for eight figures." "I made my first million by 30." Their entire identity wrapped around their bank balance.
When the 2008 crash hit, I watched some of these people completely unravel. Not just financially, but psychologically. Without their wealth as a defining feature, they didn't know who they were. One client told me he felt "worthless" after losing 40% of his portfolio, even though he still had more money than most people see in ten lifetimes.
This hit close to home for me. For years, I'd also measured my value by my salary. Making six figures in finance felt like proof I mattered. Leaving that salary behind at 37 forced me to rebuild my entire self-concept from scratch. Now I know that confusing money with identity is a trap that keeps you perpetually insecure, no matter how much you earn.
6. They bought their way out of every discomfort
Slight inconvenience? Throw money at it. Emotional problem? Buy something expensive. Relationship issue? Book a luxury vacation instead of having a hard conversation.
I watched clients use wealth as armor against any form of discomfort, growth, or genuine human experience. They'd pay others to have difficult conversations for them. They'd purchase experiences instead of creating them. They'd buy their children's affection instead of earning it through presence and attention.
One client paid a service to write personal letters to his kids because he couldn't find the words himself. Another hired someone to plan "spontaneous" romantic gestures for his wife. They'd outsourced the very experiences that make us human.
Growth comes from discomfort. Character builds through challenges. When you buy your way around every obstacle, you rob yourself of the very experiences that create wisdom, resilience, and genuine connection.
7. They believed their wealth made them experts on everything
Success in making money somehow convinced many clients they were authorities on all subjects. I sat through countless meetings where wealthy individuals lectured actual experts on medicine, education, art, science, and politics, simply because their bank accounts gave them false confidence.
One client regularly argued with his doctors about medical treatment because "I didn't become successful by listening to others." Another insisted on redesigning his architect's plans despite having zero design experience, resulting in a disaster of a mansion that needed massive reconstruction.
This arrogance extended beyond professional services. These clients would dominate conversations at social events, dismissing others' expertise and experiences because they assumed financial success equals universal wisdom.
Real intelligence involves knowing what you don't know. Wealth might give you access to experiences and education, but it doesn't automatically grant expertise.
Final thoughts
Working in private wealth management gave me an invaluable education, just not the one I expected. Instead of learning what to do with wealth, I learned what not to do with it.
Today, years removed from that world, I measure richness differently. A garden that produces food I can share with neighbors. Trail runs that cost nothing but give me everything. Volunteer shifts at the farmers market where I connect with my community. These things fill my life in ways that managing millions never did.
Money is a tool, nothing more. It can build or destroy, connect or isolate, elevate or diminish. The behaviors I witnessed taught me that true wealth has nothing to do with your portfolio balance and everything to do with how you treat others, how you value yourself beyond material success, and whether you can find enough in whatever you have.
The richest life is one where money serves your values, not the other way around.
