Silverman grew up in Ann Arbor, Michigan, where he attended Community High School.

He earned a Bachelor of Arts in public policy from Brown University in 1991, after which he spent two years working for New Jersey Senator Bill Bradley.

In November 1998, Silverman quit his job at ADAC Laboratories[3] to work full time on building what would become Evite.

[6] He left Skype in 2010 to join Greylock Partners as an executive-in-residence, before moving on to an executive role at American Express.

After an activist investor took a stake in the company and called for it sale, Etsy's board ousted longtime CEO Chad Dickerson and installed Silverman as chief executive officer.