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Hastings attended Buckingham Browne & Nichols School in Cambridge, Massachusetts, and sold vacuum cleaners door-to-door in a gap year before entering college. He graduated from Bowdoin College with a Bachelor of Arts degree in Mathematics, which he found "beautiful and engaging" He joined the Marine Corps officer training through their Platoon Leader Class, and spent college summers in the Marines, including a stint at the Officer Candidate School boot camp at Marine Corps Base Quantico, Virginia in the summer of 1981.
Hastings was born in the early 1960s and grew up in Washington, D.C., and the Boston area. His father was an attorney for the U.S. Department of Health, Education, and Welfare. After graduating from a private school in Cambridge, Massachusetts, Hastings went on to Bowdoin College in Maine, where he studied mathematics.
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Hastings attended Buckingham Browne & Nichols School in Cambridge, Massachusetts, and sold vacuum cleaners door-to-door in a gap year before entering college
Hastings studied mathematics at Bowdoin College in Brunswick, Maine, graduating with a bachelor’s degree in 1983. After serving in the U.S. Marine Corps, he spent two years with the Peace Corps, most of the time teaching math in Swaziland (now Eswatini). He returned to the United States and went to Stanford University, where he received (1988) a master’s degree in computer science. Subsequently Hastings became a software developer, and in 1991 he founded Pure Software (later Pure Atria Corporation), which he sold in 1997 for a substantial profit.
He embarked on a career as a software developer and accepted a job at Adaptive Technology. There he worked under Audrey MacLean, the CEO at that time, from whom he learned the value of focus. He quit this job in 1991.