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February 11.2026
3 Minutes Read

Why Billionaires Are Alarmed About Their Kids' Prospects in Today's Job Market

Worried student in library reflecting on job market.

Why Billionaires Are Rethinking Their Kids' Career Paths

In a rapidly changing job market, even billionaires are recognizing that their children face career obstacles unlike those they encountered in their youth. Wealth manager Patrick Dwyer highlights a growing concern among ultra-wealthy parents about their children's ability to secure stable employment in traditional fields. Many high-net-worth families are grappling with the harsh reality that recent college graduates are increasingly struggling to find jobs, with unemployment rates creeping up to 9.7% as of September 2025. This startling statistic raises questions about the future of work and the strategies parents can employ to ensure their children thrive.

The Changing Landscape of Job Opportunities

The state of the U.S. job market poses challenges not only for young grads entering the workforce but also for billionaires who are significantly rethinking how they prepare their children for the future. Economic uncertainties, rising living costs, and the pervasive influence of artificial intelligence have resulted in a hiring landscape that is drastically different from the past. Dwyer explains that while wealth can cushion living conditions, it does little to guarantee career success for the younger generation. These billionaires are becoming acutely aware that if they do not equip their kids with meaningful opportunities to develop their skills, the children may end up having less control over their destinies than they did.

The Attraction of Entrepreneurship: A New Path Forward?

In response to these challenges, many wealthy parents have pivoted to fostering entrepreneurial spirit among their children. Educated about traditionally stable career paths, these parents are now advocating for their kids to explore startups and launch their own ventures in emerging industries. The rationale is clear: a significant financial cushion allows these future leaders to take the risks necessary to succeed in business, despite the high failure rates associated with startups. Such encouragement signifies a shift from the classic path of corporate success to a model that prioritizes innovation and resilience.

The Role of AI in Job Preparation

Interestingly, billionaires like Mark Cuban are emphasizing the importance of focusing on small businesses over large corporations when it comes to job hunting. According to Cuban, positions in small to medium-sized companies often afford new graduates the opportunity to make their skills essential to the company's operations, particularly as AI transforms job responsibilities. With AI automating many tasks previously performed at entry-level, knowledge of how to implement AI solutions can set candidates apart in a competitive job market.

Developing New Skill Sets and Preparing for the Future

As a way to address the changing work landscape, both Dwyer and Cuban suggest that ensuring children have a diverse skill set is essential. Entrepreneurs educated in AI tools can harness their business acumen to create jobs or enhance efficiencies in smaller firms that lack the infrastructure of their larger counterparts. By encouraging children to immerse themselves in internships or entrepreneurial opportunities, these wealthy parents are actively shaping the next generation to not just adapt but thrive amidst uncertainty.

A Conclusion on the Urgency for Change

The realities of today's job market compel wealthy parents to reconsider their approaches in preparing their children for the workforce. The traditional ladders of success are being dismantled, making it imperative for billionaires to cultivate resilience and innovation among their offspring. Thus, the question becomes not merely how to protect wealth but how best to empower the next generation to navigate the complexities of a job market in flux.

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02.21.2026

How I Bought a $575K Duplex By Age 27: A Young Investor's Journey

Update How I Became a Young Real Estate Investor At just 27, I took the plunge into homeownership by purchasing a $575K duplex all on my own. This is not just a housing achievement; it’s a testament to careful planning and leveraging opportunities that many young people might overlook. While buying a first home—especially in today’s inflated market—can feel daunting, my story can serve as inspiration for those looking to follow a similar path. Attention to Financial Goals Pays Off A few years ago, I began focusing on my financial goals, working diligently to save and educate myself on the real estate market. Like Ryan Chaw, who bought his first rental property at age 23, I understood the hard work that would need to go into achieving my dream. Chaw lived at home with his parents to rent out his property and earn income, which served as a crucial step before he expanded his property portfolio. To achieve the same, I opted to cut down on discretionary expenses and boost my savings, a strategy that paid off when I finally secured my own place. Co-buying as a Creative Option While I opted to purchase the duplex solo, many young buyers are finding success through "co-buying" arrangements with friends. According to recent trends, co-buying homes is an increasingly popular route for millennials and Gen Z facing high housing prices. From shared living arrangements to splitting mortgage payments, this strategy allows buyers to pool resources and make homeownership attainable. This augments personal security and common goals, like the dynamic partnerships featured in New York City and Washington, D.C. While I didn’t choose this path, I explored the option back when I was deciding on purchasing my duplex, reflecting on the potential benefits. Learning from Mistakes: The Importance of Due Diligence As exciting as home buying can be, I quickly realized that with every opportunity comes responsibility. Homeownership isn’t just about the purchase; it also involves upkeep and unforeseen costs. I echo Ryan Chaw’s lessons learned about the importance of home inspections—a mistake he made was failing to detect hidden issues, resulting in pricey repairs. He recommends that new buyers prioritize full inspections before finalizing purchases. My proactive approach included thoroughly assessing potential issues that could arise, which ultimately aided my negotiations in the buying process. The Road Ahead: Future Real Estate Ventures Having successfully bought my duplex, my journey is just beginning. I plan to follow in the footsteps of investors like Chaw and others who have expanded their portfolios with multiple properties. With the knowledge gained through my first investment, I aim to consider other could-be properties for rental or personal use. Considering the rising demand for affordable housing and creative lease strategies, I feel confident navigating the real estate landscape. Whether you’re just contemplating your first property, evaluating an investment as a co-buyer, or aiming to secure a piece of the American dream, the real estate market holds numerous opportunities for those willing to pursue them. Creating a plan that fits your financial landscape—while being adaptive to challenges—can pave the way for future success. Don’t forget the lessons learned by investors like Chaw who utilized their youthful determination to create meaningful wealth. As you step into this realm, make sure to do your due diligence, create a solid strategy, and remain open to evolving your plans.

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Why Moving to Berlin Will Transform Your Life Abroad

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