[12] After a period of time and world travel, Adelson moved to San Francisco, California in 1993, pursuing instead a career in Internet infrastructure and entrepreneurism.

[13] Adelson commuted from New York to San Francisco to found and operate Revision3 and Digg, eventually moving back to Mill Valley, California in the summer of 2009.

[13][16] While at Netcom, In February 1995, Adelson was present and managing network operations during the pursuit and capture of former computer hacker Kevin Mitnick by Tsutomu Shimomura.

[17] In late 1996, Adelson worked for Digital Equipment Corporation's Network System Laboratory, specifically Albert M. Avery IV, to build and operate the Palo Alto Internet Exchange (PAIX).

Adelson worked alongside Stephen Stuart and Paul Vixie to build a datacenter and services suited for scaling the core of Internet traffic.

[23][24][25] Adelson also assisted in the raising of capital including private equity rounds, a high-yield new entrant bond deal, and an initial public offering in August 2000.

[26] Adelson and Kevin Rose, along with co-founding team that included Ron Gorodetsky, Dan Huard, Keith Harrison and David Prager, founded Revision3 in April 2005.

Adelson remains Chairman of the Board of Revision3 presently and hosted his own show called Ask Jay which demystifies the start-up process by providing advice, tips, and answering questions.

Adelson had been advising the business, largely stemming from a relationship with the company's founder, Joseph Carl Stump, who served as Lead Architect at Digg, Inc.

[3] Opsmatic launched to the public in 2014 and Adelson stepped back his active role in order to focus on a new pursuit of a venture capital firm, Center Electric.

[43] He also advises companies, including Bonusly, Circa, DAV foundation, Founders Den, Ginkgotree, NewsBasis, Katchall, Nuzzel, Ouya, Permanent, Kiip, SOAK, SiiTV, Urban Airship, August, LoveBook, Graphic.ly,[44] Fflick (sold to Google/YouTube in 2011),[45] RoqBot, Plex, and Attachments.me.