My wife had this wonderful letter she wrote to each of our sons as they finished school and headed off into the real world. The letter was full of admiration for their accomplishments, encouragement, and hope for their future success. But also buried in the letter was a nice kick in the butt as they headed out the door. She explained that they would be guests in our home whenever they returned. Since actions speak louder than words, she followed that up by immediately painting their rooms pink and replacing the curtains on the windows with lacy ones.
Her letter contained a key sentence that they and I remember.
“We have the utmost confidence in your eventual success, but we would not want to deprive you of the valuable lessons you can learn from success and failure.”
This was a heartfelt but firm message and a way to explain that from now on, they were accountable for their success or failure. We will be here for advice, encouragement, and emotional support, but the flow of cash stops now, and they have become responsible for their lifestyle. Neither of them has ever asked for anything other than advice and encouragement from time to time. They are both successful in the professions they chose to pursue.
Starting with little to nothing and building a successful career or business is as American as it gets. It is how our economy and society works. We still reward hard work, innovation, and risk taking.
American Millionaires and Billionaires
A myth about wealth, particularly generational wealth, persists in America. Some individuals are born into wealth and privilege, but on a percentage basis, they are always a tiny fraction of our population. These citizens often have derogatory labels such as “Trust Fund Babies” or “Born with a silver spoon in their mouth,” signaling that our society disdains those who avoid work. Often, these individuals are vilified or glorified by the media and garner a disproportionate amount of news coverage, distorting their importance and actual wealth. In some perverse distortion of reality, Washington and the media seem to have no problem with great wealth in sports or entertainment but significant problems with wealth accumulated through hard work in business. From my perspective, this is the creeping Marxism working its way into our society like a parasitic worm working its way to your brain.
There also seems to be a cycle to this wealth accumulation by a small number of individuals, as we saw in the late 1800s in the “Gilded Age.” The names of the ultra-successful come to mind easily when we mention John D. Rockefeller, Andrew Carnegie, Henry Ford, Harvey Firestone, Andrew Mellon, and J. P. Morgan. They shared great success and a willingness to take significant risks and work extremely hard to pursue their interests. They operated at a point in time when technological changes like the steam engine, internal combustion engine, electricity, air travel, and other inventions we now take for granted were emerging. Embracing risk and moving forward no matter the odds distinguished them from others.
In America, even if you are the master of the absurd and ridiculous, you can achieve great wealth. There is no better example than the Kardashians, who are famous for being famous and have made it big financially. The Kardashians are famous for all the wrong reasons, but they represent a perverse form of success, in my opinion. Then there is Jimmy Donaldson, aka “Mr. Beast,” who achieved wealth and fame through 300 million YouTube followers. You only need to find your niche and dedicate yourself to success in America.
Our Second Gilded Age
I believe we are in the midst of a “Second Gilded Age” brought on by rapid advancements in technology and the unusual ability of a small group of individuals to adapt to these changes. The key to this renewal is the voter’s role in keeping governmental interference to a minimum. Our Federal Government can sometimes be the friction that impedes progress.
When we discuss technological advances, the names of Bill Gates, Elon Musk, Jensen Huang, Sam Altman, Steve Jobs, Mark Zuckerberg, and Tim Cook come to mind. Then there are captains of industry outside of technology, such as Warren Buffett, Sam Walton, Jamie Diamon, Jeff Bezos, Michael Jordan, Tiger Woods, Steven Spielberg, J. K. Rowling, and even Taylor Swift.
The Fallacy of Monopoly Busting
Many will argue that the breakup of many companies at the end of the first Gilded Age was necessary, but I now believe it was a mistake. Companies have a life like their founders and never live forever in our system. Obsolescence, changing consumer demand, advancing technologies, and different skills from generation to generation keep wealth accumulation from staying concentrated like it did in European monarchies.
With globalization, we now compete internationally, not nationally, to produce the largest and smallest goods and services. To compete effectively with China and other economic powers, our corporations need scale. Manufacturing companies need the efficiency that comes from large-scale operations, and only our largest companies offer these advantages. The threat of anti-trust actions can stifle innovation and investment. We need oversight, not interference.
Any technology company is just one day away from obsolescence, as we see with the introduction of artificial intelligence. Many, if not most, technology companies around today will be gone in a decade if they cannot adapt. These have been the source of vast wealth creation but will fade with or without government interference. With government interference, a disproportionate number of companies will fail and we will be less competitive on the world economic stage..
“Shirtsleeves to shirtsleeves in three generations.”
Often cited by Andrew Carnegie, the exact attribution is unknown.
A more detailed explanation of this proverb is explained as:
“The First Generation, having faced a life of hardship, is driven by the determination to secure a better future. Their willingness to work diligently and make significant sacrifices pays off, often resulting in accumulated assets they can pass on to the next generation.
The Second Generation, having witnessed their parents’ struggles, understands the value of hard work. Although they enjoy a more comfortable lifestyle, they remain mindful of their frugal upbringing. This awareness helps them make wise financial and educational choices, further building upon the foundation laid by their parents. As a result, the Second Generation often achieves even greater wealth in their later years.
The Third Generation grows up with no memory of want or struggle. They experience a life of plenty and often lack an understanding or appreciation for the hard work and sacrifices their parents and grandparents made. This lack of perspective frequently leads them to squander the wealth that was meticulously built by the previous generations.”
Source Unknown but attributed to many individuals and cultures in slightly different forms.
Fall Seven Times, Get Up Eight
As a nation, we have not done a good job of stressing the importance of resilience and determination for many of our youth. Even if you become ultra-successful, life is hard. What makes the difference is how you view failure and how much determination you have to use your failures as steppingstones for success.
“Fall seven times, get up eight.”
Japanese Proverb
You only need to be in the workforce in America for a short time to realize there are no participation trophies. You either succeed or fail based on your own will and determination. There is no reason for not having your own “Personal Gilded Age” if wealth is a goal or priority. In America, will and determination are the only things standing in the way of success.
Today, no one illustrates this more than Elon Musk and his endeavors with SpaceX. According to Musk, several times while building SpaceX, one more failed rocket launch would have bankrupted the company. However, he and his team viewed each failure as a lesson learned and moved forward. Their perseverance is a repeat of Thomas Edison’s failed lightbulb experiments, where he kept moving forward, trying filament after filament until he found the right one. The difference is scale, where a failed rocket launch can cost hundreds of millions.
Often overlooked in the spotlight placed on the ultra-successful is the real engine behind our economy. American capitalism has always been driven not by those who have achieved success but by the collective effort and determination of those working to become successful. For each Steve Jobs, millions are striving to become the next Steve Jobs. Millions of people with ideas or products are willing to work hard to be the next Apple.
Immigrants, both legal and illegal, know this and still flock to our borders. They recognize the enormous economic opportunity afforded to Americans and want a piece of the pie. For sure, there are millions of freeloaders and tens of thousands of criminals, but most come seeking a better life and a chance to compete on our terms in our capitalist system. Immigrants often have a perspective, a point of comparison, that we lack. The key to immigration is control in both numbers and skills. We are a nation of immigrants, and with an aging population, we need new people with fresh ideas. But we are not a nation unless we have the will and capacity to distinguish the desirable versus undesirable who arrive at our borders and shores.
MAGA Era of Renewal
With President Trump’s reelection, we have a chance to unleash our economy’s full potential once again and to push back against those who work to tear us down and create dissension. This time, there are catalysts at work that will boost our odds of reclaiming our entrepreneurial DNA.
The Boomer Generation has been successful and will unfortunately be aging out over the next decade. They will pass along great wealth to their children. Unlike the First Gilded Age, this wealth will pass through millions of families and give Generation X a “leg up” that no other generation has enjoyed. Some estimate this wealth transfer to be as high as $84 trillion.
President Trump and the MAGA Republicans will do their best to keep this money away from Washington, where it would just be wasted. They know this wealth transfer will propel our economy to new heights and give future generations the best chance of preserving capitalism and our envied way of life. Generation X might have the most incredible helping hand in history to improve the world.
For one, I hope there is a Third Gilded Age because it will come from the wealth transfer of the Baby Boomers and the hard work, dedication, and innovation of Generation X and Millennials. Still, even with this helping hand, only a tiny percentage will accept the risk needed to build significant wealth. It is how capitalism works, and we must embrace it and keep Washington in Washington.
It is not wealth that is the challenge; it is the acceptance of risk and getting up every time we fall, especially in newer generations that have been taught risk avoidance. There are no participation trophies in life or in business.
Resources and Further Reading
All the Generation Names and Years (1845 – 2039)!, By Editorial Staff, Fun Group Names, fungroupnames.com, Last accessed January 10, 2025.
Great Wealth Transfer: How Boomers Are Passing on Fortunes to Their Heirs, By Andrew Lisa, GOBankingRates, gobankingrates.com, June 5, 2024.
How Most Billionaires Made Their Money, By Grace Chung, Forbes, forbes.com, April 13, 2024.
How Robber Barons Flaunted Their Money During the Gilded Age, By Patrick J. Kiger, History Channel, history.com, September 26, 2023.
Incredible Millionaire Statistics & Facts for 2025, By Hristina Nikolovska, Moneyzine, moneyzine.com, January 31, 2024.
Is The ‘Shirtsleeves To Shirtsleeves’ Analogy Really Relevant Today?, By Paul Andrews, Family Business United, familiybusinessunited.com, October 8, 2024.
List of richest Americans in history, Wikipedia, wikipedia.org, Last accessed February 26, 2024.
Super rich’s wealth concentration surpasses Gilded Age levels, By Ethan Wolff-Mann, yahoo!finance, finance.yahoo.com, July 7, 2021.
Tax-Free Inheritances Fuel America’s New $73 Trillion Gilded Age, By Ben Steverman, Bloomberg, bloomberg.com, February 2, 2022.
Total wealth of the wealthiest men in the United States during the period of the Gilded Age from 1870 to 1914 (in billions of 2006 U.S. dollars), By Statista Research Department, statista.com, September 14, 2027.
What Percent of Millionaires are Self Made?, Sharon Nyoike, NovaRiche, novariche.com, February 20, 2024.
Who were the tycoons of the Gilded Age? Meet the ruthless ‘robber barons’ who made millions, By dam IP Smith, History Extra, historyextra.com, January 25, 2022.
