[2] Born and raised in Rhode Island, Josephson graduated from Skidmore College in 1994.
[3] Josephson began his career at Cone Communications in 1994 as an intern, becoming an account manager at the firm.
[4] In 1999, he worked in many roles with About.com, ending as the General Manager and EVP before it was sold to Primedia in 2000.
[8][9] In 2020, he co-founded Castiron, a software-as-a-service (SaaS) platform and consumer marketplace, and was the CEO until it was sold to The Good Soil Movement in 2024.
[10] Since 2020, Josephson has been an executive coach, dedicated to helping startup CEOs and leadership teams.