Hastings was born in Boston, Massachusetts. 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 before joining the Marine Corps. He later pursued service as part of the Peace Corps. Hastings' first job was at Adaptive Technology, where he created a tool for debugging software. He left the company in 1991 to lay the foundation to his first company, Pure Software, which produced products to troubleshoot software. He faced difficulties while leading the company, eventually leaving in 1997 and seeking to avoid similar issues with his next startup. This led to the creation of Netflix, a streaming service that has amassed a collection of 100,000 titles and more than 100 million subscribers.