He later co-founded two information security startups, one of which developed innovative anti-spam technology that is still in use today (both firms were sold to NASDAQ listed companies).

After authoring more than a dozen textbooks during the 1980s on how to use software applications like spreadsheets, databases, and word processors, mostly through McGraw Hill Cobb's first book on PC and LAN Security was published in 1991.

After a brief hiatus from privacy and security research, during which he produced an independent documentary on racial inequality in America (Dare Not Walk Alone, 2006), Cobb co-authored a peer-reviewed paper on the dangers of malicious code use by governments, which he termed "righteous malware".

[13] Cobb's dissertation for his Master of Science degree in security and risk management at the University of Leicester addressed aspects of the cybersecurity skills gap.

[17] In an effort to spread awareness of emerging threats Cobb has coined words for two related digital security problems: jackware and siegeware.

[20] The Tech Champion Awards are presented to "leaders focused on driving innovation, job growth and advancements for the information technology (IT) industry.