Cheapskate Millionaires: Why Are Most Rich People So Damn Cheap? (2024)

Cheapskate Millionaires: Why Are Most Rich People So Damn Cheap?

(I have so much to say on this topic and i'm going to do a lot more updates to this article, sharing real life funny experiences that i've encountered with this breed of individual through out my life so keep checking back in on this one)

Is it wrong to find it pathetic that this is an age-old question that has plagued us mere mortals for eons: Why are most rich people so damn cheap?

As someone who has had the pleasure (or perhaps the dis-pleasure depending where, when and with who) of rubbing elbows with the worlds uber-wealthy, I can attest to the fact that many of them are indeed the cheapest of the cheap. And I'm not just talking about the ones who made their fortunes through penny-pinching and frugality. No, even the ones who inherited their wealth for doing nothing except being part of the lucky sperm club and have more money than they know what to do with are still the cheapest bastardos when it comes to spending their cash on anyone but themselves.

(The trust fund Daddys boys from Italy are some of the worst of their kind)

It's a paradox, really. They'll drop millions on a private jet, a Basquait or a luxury yacht without blinking an eye, but when it comes to tipping the valet or treating their friends to dinner, suddenly their wallets are vacuum sealed shut.

But why? Why would someone who has more money than they could ever spend be so unwilling to part with it? Why would they be so CHEAP?

The answer, my friends, is simple: GREED.

You see, the ultra-wealthy didn't amass their fortunes by being generous and selfless. They did it by ruthlessly pursuing their own interests, even if it meant trampling over others in the process. And once they've got their money, they're not about to give it away to anyone, no matter how deserving or in need.

But it's not just about greed. There's also a sense of entitlement that comes with extreme wealth. When you're used to getting whatever you want, whenever you want it, it's easy to develop a mentality that you deserve everything and owe nothing to anyone else.

And let's not forget about the fear of losing it all. Many wealthy individuals grew up with little or nothing, and the thought of returning to that state is a powerful motivator. So they hold onto their wealth with a death grip, even if it means being cheap in other areas of their lives.

But here's the thing: being cheap doesn't make you happy. Sure, it might feel good to see your bank account grow and your net worth rise, but at the end of the day, money can't buy you happiness or fulfillment. And if you're not using your wealth to make a positive impact on the world, what's the point?

So to all the ultra-wealthy out there: loosen your grip on your wallets. Be generous with your money, not just with your family and friends, but with those in need. Use your wealth to make a difference in the world and leave a positive legacy behind.

And to the rest of us: don't envy the wealthy for their material possessions. Pity them for their inability to find true happiness and fulfillment.

Cheapskate Millionaires come in all shapes and sizes from all over the globe, here i will cover some of the most common of their breed:

1. The "Impress the Girls" Cheapskate: This type of cheapskate millionaire is ONLY generous when it comes to showing off for women. They'll splurge on expensive dinners, gifts, take women on extravagant trips, all in the name of looking good and trying to get laid, they're so tight that their ass squeaks when they walk. But don't be fooled by their flashy displays of generosity - when it comes to actually helping out friends or contributing to charitable causes, these guys are about as generous as a leech at a blood bank.
2. The "I'll Buy My Way to Heaven" Cheapskate: This type of cheapskate millionaire will only be generous when it comes to high profile charity auctions or other public displays of wealth. They'll bid sky-high amounts for items they don't even want, just to SHOW OFF as the highest bidder. But when it comes to quietly supporting charities or causes that don't offer any public recognition, they're nowhere to be found. They almost never know anything about the charity other then who is going to attend and who is going to be sitting at their Amfar or Unicef tables.
3. The "My Money is My Money" Cheapskate: This type of cheapskate millionaire is the most common. They're incredibly protective of their wealth and will only part with it when absolutely necessary. They'll haggle over every penny and never tip generously. They might even refuse to pay their fair share of a bill or expense, leaving others to pick up the slack. They're the ones who love to conveniently get up and go to the bathroom right after someone asks the waiter for the check or pull the infamous dine and dash technique (cause they suddenly don't feel well and don't leave any money for their share of the bill)
4. The "I'll Only Give to My Own Kind" Cheapskate: This type of cheapskate millionaire is only generous when it comes to their own community or circle of friends. They'll donate large sums to charities that benefit people like themselves, but won't support causes that help those less fortunate. They might even be dismissive of people from different backgrounds or socioeconomic levels. Anyone interested in donating to some self serving religious causes?
5. The "I'll Only Give to Get Ahead" Cheapskate: This type of cheapskate millionaire is only generous when it comes to their own self-interest. They'll donate to causes or organizations that they think will benefit them in some way, like buying their way into exclusive clubs or social circles. They might even try to use their wealth as leverage to get ahead in business or other areas of life. Anyone interested in the Robinhood Foundation or some self serving social causes? NYC,LA and Miami are littered with these types and can usually be identified by their bad breath veneer smiles, Rolex watches and some other trinkets they use as a pretend low key flex.

Do you know the saying "you get what you pay for," but what about the effects of being a downright cheap person? As it turns out, being cheap has some serious energetic and spiritual consequences that go far beyond someones your wallet.

First and foremost, being cheap can have a negative impact on your relationships. Whether it's refusing to split the check evenly or insisting on a measly tip for a hardworking waiter/waitress, being stingy can also make you come off as selfish and unappreciative. And let's be brutually honest, absolutely no one wants to hang out with someone who has money and is constantly crying poverty with every purchase.

On a much deeper level, being cheap can also affect your energy and sense of abundance. According to spiritual theories like the Law of Attraction, what you put out into the universe is what you receive back. So if you're constantly focused on scarcity and lack, you're likely to attract more of the same into your life. On the flip side, a mindset of abundance and generosity can bring more prosperity and positivity your way. One of my favorite lessons from Victoria Song's book "Bending Reality" is the topic of contraction and expansion. Whenever I'm driving along the oceanside on South Ocean Boulevard in Palm Beach on my Vespa,

I can't help but scream out for as long as i can at the top of my lungs in full Jamison vibrato.

Expansioooooooooonnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnnn

It sometimes freaks out the older residents of the island but it's just so freeing. It's such an easily relatable concept that speaks volumes to my current state of mind, it's definitely worth listening to repeatedly for its great messages, i'm NOT just saying this because she is my friend. Check it out here on Audible: https://www.audible.com/pd/Bending-Reality-Audiobook/B08QVMZCCJ

But what about the physical effects of being cheap? Well, scrimping and saving can lead to a lack of self-care and quality of life. Cutting corners on things like healthcare or home repairs can lead to bigger issues down the line, both financially and emotionally. And constantly denying yourself pleasures and experiences due to a fear of spending money can lead to a life that's lacking in joy and fulfillment.

So what's the solution for the cheapskate among us? It's all about finding a balance between frugality and generosity. Yes it's important to save money and plan for the future, but also to allow yourself to enjoy the present moment and give back to others. Whether it's through volunteering or donating to a cause you believe in, generosity can bring a sense of purpose and positivity to your life.

In the end, being cheap may seem like a way to save money in the short term, but the energetic and spiritual effects can be far-reaching. So take a deep breath, loosen your grip on your wallet, and remember that sometimes the best things in life are worth a little investment.

Here are 5 top NY Times best-selling books to help you stop being cheap or to help you be more generous:

1. "The Generosity Factor: Discover the Joy of Giving Your Time, Talent, and Treasure" by Ken Blanchard and S. Truett Cathy - This book offers practical tips and inspiring stories to help readers cultivate a spirit of generosity. You can find it on Amazon at: https://www.amazon.com/Generosity-Factor-Discover-Giving-Treasure/dp/031026945X
2. "The Art of Giving: Where the Soul Meets a Business Plan" by Charles Bronfman and Jeffrey Solomon - This book offers a unique perspective on philanthropy, exploring how giving can be both a deeply personal and a highly strategic act. You can find it on Amazon at: https://www.amazon.com/Art-Giving-Soul-Business-Plan/dp/0471196324
3. "The Soul of Money: Transforming Your Relationship with Money and Life" by Lynne Twist - This book offers a powerful exploration of the spiritual dimensions of money and how we can use our resources to create a more just and compassionate world. You can find it on Amazon at: https://www.amazon.com/Soul-Money-Transforming-Relationship-Life/dp/0393353973
4. "The Gift: Creativity and the Artist in the Modern World" by Lewis Hyde - While not specifically focused on generosity or giving, this book offers a powerful exploration of the nature of creativity and the importance of sharing our gifts with the world. You can find it on Amazon at: https://www.amazon.com/Gift-Creativity-Artist-Modern-World/dp/0307279502
5. "The Power of Giving: How Giving Back Enriches Us All" by Azim Jamal and Harvey McKinnon - This book offers practical tips and inspiring stories to help readers cultivate a more generous spirit, including strategies for giving in the workplace, in our personal relationships, and in the world at large. You can find it on Amazon at: https://www.amazon.com/Power-Giving-Back-Enriches-All/dp/1577318076

Don't be a Cheapskate Millionaire or a CHEAPSKATE of any kind...Jamison