How the World’s Wealthiest Built Their Fortunes from the Ground Up

Before they owned private islands, billion-dollar brands, and Gulfstream jets, some of the world’s most powerful business leaders held ordinary jobs—shoveling snow, flipping burgers, and selling chewing gum door-to-door. These stories go beyond rags-to-riches narratives; they reveal the unteachable traits of resilience, discipline, and long-term vision that helped shape their extraordinary destinies.

At Resident, where legacy and aspiration converge, we revisit the humble beginnings of five self-made billionaires whose early jobs helped forge the mindset behind their monumental success.

Before building a media and financial data empire, Michael Bloomberg paid his way through Johns Hopkins University by mowing lawns, selling Christmas wreaths, and shoveling snow in his Boston neighborhood. He later worked as a parking lot attendant and earned an MBA from Harvard Business School—long before Wall Street would take his calls.

His break came at Salomon Brothers, where he rose through the ranks before being let go in a merger. That setback became his launchpad: he used his severance to start Bloomberg LP, the company that revolutionized how financial data is delivered.

Michael Bloomberg’s Net Worth (2025): $94 billion

According to Forbes, Bloomberg’s wealth stems from his majority ownership in Bloomberg LP, a global media and tech powerhouse.

Legacy Insight: Bloomberg Terminals became a status symbol among elite traders—an early sign that influence often begins with utility.

Bill Gates was still in high school when he landed his first programming gig with TRW, a defense contractor—a job few teenagers could dream of in the 1970s. This early access to computers sharpened his natural aptitude for software.

After dropping out of Harvard, Gates co-founded Microsoft and spearheaded the personal computing revolution. Though he’s no longer at the helm of Microsoft, his name remains synonymous with innovation—and large-scale philanthropy.

Bill Gates’ Net Worth (2025): $125 billion

Gates’ fortune continues through Microsoft shares, Cascade Investments, and his philanthropic focus through Gates Foundation.

Legacy Insight: Gates now runs Gates Ventures and the Gates Foundation independently of Melinda French Gates, with separate missions.

Oprah Winfrey’s journey from rural poverty in Mississippi to media royalty is one of resilience and reinvention. Her first job was as a grocery clerk in Nashville, working next to her father’s barbershop. By 16, she was reading the news on local radio; by 19, she was anchoring the evening news.

Her on-screen authenticity transformed daytime television. With Harpo Productions and OWN Network, she redefined the business of influence and became one of the most trusted public figures in America.

Oprah Winfrey’s Net Worth (2025): $2.8 billion

With ownership stakes in Weight Watchers, Apple TV+, and a vast real estate portfolio, Winfrey’s empire is as diverse as it is powerful.

Legacy Insight: Winfrey’s properties span Montecito, Telluride, and Hawaii—each a reflection of intentional luxury and privacy.

At just six years old, Warren Buffett sold packs of Wrigley’s gum door-to-door. By 11, he made his first stock purchase: Cities Service Preferred. His early paper route in Omaha—where he deducted his bicycle as a business expense—cemented his love for numbers and enterprise.

Decades later, Buffett built Berkshire Hathaway into a conglomerate with holdings in everything from insurance and railroads to Apple stock. Today, he remains a symbol of disciplined investing and understated affluence.

Warren Buffett’s Net Worth (2025): $160 billion

Forbes ranks Buffett among the top five wealthiest individuals globally, with a fortune built on long-term value investing.

Legacy Insight: Despite his fortune, Buffett still lives in the same Omaha home he bought in 1958—proof that value doesn’t always scream for attention.

Before founding Amazon in 1994, Jeff Bezos flipped burgers at a Miami McDonald’s as a teenager. He credits the experience with teaching him about systems, responsibility, and speed—skills he would later channel into building the world’s largest e-commerce company.

As Bezos once recalled about his time working at McDonalds:

That moment of accountability never left him. Today, Bezos is reshaping the future through Blue Origin, his aerospace company, and remains a dominant force in cloud computing through Amazon Web Services.

Jeff Bezos’ Net Worth (2025): $216 billion

As of 2025, Bezos holds the second-highest net worth globally, driven by Amazon stock and investments in space tech, AI, and media.

Legacy Insight: His luxury real estate portfolio spans Manhattan, Beverly Hills, Maui and recently Miami—anchoring him in both business and leisure capitals of the world.

At Resident, we celebrate opulence, but we also revere the effort behind it. These aren’t just stories of wealth—they’re reminders that even the world’s most powerful empires can begin with a minimum-wage job or a snow shovel.

For our readers, who understand that wealth is more than acquisition—it’s intention—these journeys are proof that vision, grit, and consistency remain the true luxuries of success.

Every mogul starts somewhere. Whether it’s Jeff Bezos mopping floors or Oprah announcing the weather, greatness often begins in obscurity. For those crafting their own legacies, these stories offer more than inspiration—they offer a blueprint.