The First Jobs of 10 Wealthy Entrepreneurs

Investing Advice

There’s a stereotype in America that successful CEOs and entrepreneurs were born with silver spoons in their mouths. Their eye-popping fortunes were little more than a gift from luck, genetics or privilege. Given this stereotype, it’s tough to imagine people like Warren Buffett ever working “regular jobs” like the rest of us. However, you may be surprised to learn that many titans of industry got their start in very pedestrian positions that you wouldn’t suspect. Today, we look back on the first jobs of 10 wealthy CEOs and entrepreneurs.

Ross Perot


Respected worldwide as one of the most effective business leaders of the 20th century, Ross Perot got his working start earlier than anyone on this list. As CNN tells it, Perot’s father was “…a cotton broker and a part time horse trader who put his young son to work at the age of six breaking horses for a dollar or two apiece.” (The elder Perot also notes that “”Perot’s nose still shows the results of the falls he took.)” Once he was older, Perot enlisted in the US Navy in 1949 and helped to establish its honor system, and by 1953, he was president of his battalion. So began a life of leadership that would see him create and sell-off two very successful, independent companies (Electronic Data Systems and Perot Systems) for billions each.

Wayne Huizenga


Before becoming a waste management magnate, owning the NFL’s Miami Dolphins or MLB’s Florida Marlins, Wayne Huizenga got early work experience as a gas station attendant during high school, according to Forbes. Reportedly, Huizenga also took a truck driving position at 17 to help his mother with household bills following her traumatic divorce from his father. Huizenga later enlisted in the Army reserve in 1959. By 1960, Huizenga was already buying his own truck and recruiting clients for the fledgling waste management company that would build most of his $300+ million net worth.

Warren Buffett

(Ethan Bloch)

Investing mogul Warren Buffett’s first job reads like something out of a novel. Long before he made history with his shrewd and old-fashioned-style investment decisions, the Nebraska native earned his first “working capital” as a newspaper delivery boy. According to, Buffett was already, at age 13, “…savvy enough to deduct the cost of his bicycle on his first tax return.” So began a path of frugality for Buffett that saw him amass over $140,000 by age 26 (in 1956), who would eventually became one of the richest men in the world at present.

Donald Trump

(Michele Eve)

Commercial real estate tycoon Donald Trump got his hands dirty (literally) for his first working capital. According Forbes, Trump accompanied his father to job sites and collected empty cans and bottles with his brother for the redemption value. It didn’t add up to much (Trump recalls it equaling a “below-average allowance”) but it no doubt taught him the value of a dollar. Humorously, Trump also notes that he later accompanied dad on rent collection jobs to scoop up bottles and cans that way, but quickly learned to, “…stand out of the doorway to avoid the possibility of being shot”.

Sam Walton


If ever an entrepreneur rose up from humble beginnings, it was Sam Walton. The Walmart founder began helping his family make ends meet at an early age, and held many odd jobs. Among these were milking the family cows, bottling the milk and hand-delivering it to paying customers. Later, Walton would take to his bike to complete a daily paper delivery route. He also sold magazine subscriptions on the side, perhaps building some early sales skills that proved crucial later on. Upon graduating high school, Walton was voted “most versatile boy” in his class. Walton continued working odd jobs early in college, including “…waiting tables in exchange for meals”, according to Wikipedia.

Jim Clark

(Marcin Wichary)

Netscape founder and maverick entrepreneur Jim Clark was anything but a “silver-spoon” case. Growing up in a poor single-parent household, Clark’s first job (after dropping out of high school) was his four years as a member of the US Navy. Michael Lewis’ book The New New Thing chronicles how disastrous this was for the young Clark, who constantly found himself at odds with authority. Like so many entrepreneurs, Clark simply could not defer to superiors for any serious length of time, and went on to found Silicon Graphics, Netscape, and Healtheon.

Larry Ellison

(Oracle OpenWorld San Francisco 2009)

Much of Larry Ellison’s early life was marked by the perception that he would never amount to anything. refers to the future Oracle co-founder as a “…seemingly aimless young man” who dropped out of high school after his mother passed away. However, unbeknownst to Ellison’s father, the young boy had developed a stunning aptitude for math and science, which paved the way for his first job as a technician at Wells Fargo. His programming duties at Ampex even saw Ellison participating in “building the first IBM-compatible mainframe system”. From these beginnings, Ellison has risen to the point where, as Guy Kawasaki writes in Reality Check, “…Larry Ellison can keep the San Jose Airport open after-hours to accommodate the landing of his own personal jet”.

Michael Dell


Dell founder Michael Dell was hardly an instant business success. According to CareerBuilder, Dell got his working start as a dishwasher in a Chinese restaurant. His starting wage? A whopping total of $2.30 per hour. Dell also displayed some early sales prowess during his high school years, when, despite not excelling academically, he raked in $18,000 in Houston Post sales – enough to buy a car and three computer systems. Once in college Dell wasted little time starting his first business (PCs Limited) in a single room of a 27 story residence hall. Before long the young company showed enough promise to inspire Dell to drop out at 19, taking a loan from his grandmother and re-naming the business to Dell Computer.

Ray Kroc


Ray Kroc’s first job epitomizes humble beginnings. His first ever job, according to, was helping out at his uncle’s soda fountain the year before he began high school. Inc’s Great Leaders series also reports that Kroc “…lied about his age to land a job as a Red Cross ambulance driver during the First World War”, but the fighting ended before he could serve. Following the war, Kroc served in a veritable revolving door of temporary capacities, including “…a pianist, a grocery store bagger, and a paper cup salesman” before buying out the McDonald brothers for their rights to the iconic hamburger chain.

Herb Kelleher


Hailed by some as the greatest American CEO of all time, Southwest Airlines’ Herb Kelleher (middle) was hardly born into executive greatness. Rather, the humble New Jersey native got his first working experience from his six summers at Campbell Soup, working under his father (also the general manager) according to Charles Blackwell’s article “Flying High with Herb Kelleher: A Profile in Charismatic Leadership.” It was here that Kelleher learned and perfected his people-focused, contrarian (and often eccentric, as this video demonstrates) management style that has remained a fixture in business school curriculums for decades.

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