In 1886, a jeweler in Redwood Falls, Minn., received an unwanted shipment of gold-filled watches. Working as a railroad station agent at the time, 23-year-old Richard Sears decided to purchase the watches himself. Then he subsequently sold them at a tidy profit to other agents up and down the rail line.
Curiously enough, that was also the same year Roebuck called it quits, selling his 50% stake to Sears for just $25,000. Don't be too hard on him, though; adjusted for inflation, Roebuck's windfall would have been worth nearly $695,000 in today's dollars -- and all after a mere eight years with the company.