The Harder You Work, The Luckier You Get

The Harder You Work, The Luckier You Get

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By Eric O'Keefe

Photography By Stuart Monk / Shutterstock

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CHARGING BULL. Arturo Di Modica 96

Published August 15, 2026

1.6 min read
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Joe Ricketts is no ordinary entrepreneur. Take, for instance, the frequently recurring element on his résumé: his repeated employment as a janitor. Ricketts did his first janitorial stint in third grade; then another at college in exchange for a dorm room at Creighton University; a third as a newlywed in exchange for reduced rent at Duchesne College; and finally after he launched First Omaha Securities, where he kept costs down by cleaning the start-ups’ restrooms himself.

Or how about his innate marketing savvy? Shortly after it launched, First Omaha trumpeted a $25 flat fee for stock trades of 100 shares, which it advertised in the Midwest edition of the Wall Street Journal. The company accelerated the call to action with an easy-to-use 800 number. The result? A burgeoning market for the feisty upstart from Nebraska.

Last but not least, the guy has got a stubborn streak a mile long.

When he asked his brokerage customers if they would be interested in a touch-tone trading system, the overwhelming response was — to put it politely — “No.”

After taking a prototype of the system for a test drive, his son Todd declared, “It sucks.” So what did Ricketts do? He invested millions in a project that was continually plagued by cost overruns and countless missed deadlines.

Yet Ricketts persisted. He listed the two reasons in his must-read autobiography, The Harder You Work, The Luckier You Get: An Entrepreneur’s Memoir. The first was personal: “Maybe I’m just a stubborn, egotistical son of a bitch,” he admitted. The second was from a professional perspective: “As Henry Ford once observed about developing the Model T, if he had asked his customers what they wanted for personal transportation, they would have answered, ‘Faster horses.’ ”

The launch of Accutrade in 1988 not only fast-forwarded revenues and profitability at Ricketts’s brokerage, it transformed the brokerage industry and presaged digital trading.

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