Winthrop, who hailed from a wealthy family, obtained his Bachelor of Arts degree from the University of Vermont in 1991. He then took up a career in corporate finance at Donaldson, Lufkin & Jenrette (DLJ) . He left the field of finance to take up management positions in small startups in the areas of manufacturing and commercial products. He went on to earn a reputation as one who built companies fast, overcame problems with scalability, and then sold them profitably. His first stint at a startup was at a sporting gear company, Atlas Snowshoe Co. (Atlas) , where after two years he became the Chief Operating Officer (COO).
When Atlas was sold off, Winthrop went on to become the Chief Executive Officer (CEO) of communications startup WebChat Communications (WebChat) . WebChat was later sold to Disney .
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