Bradley Gross, founder and president of the Law Office of Bradley Gross and an expert in technology and digital law, discusses his career arc from hacker to lawyer and the various layers of cybersecurity law.

In the podcast, Gross and host Chris Sienko discuss:

– Tell us about your unconventional journey from hacker to lawyer. What type of hacker were you, and when/where did you get interested in hacking and computers in general? (1:28)
– Do you have any hacking war stories? Any frightening or amazing accomplishments from those times? (2:20)
– Did you ever have the inclination to hack into something larger (e.g., government mainframes)? (4:40)
– Did you continue to learn and understand the concepts of hacking, maybe in a less invasive way, as the technology changed? (5:51)
– Was there a defining moment that made you realize that you wanted to be on the legal side of cybersecurity, or did you become disillusioned over time? Or was it as simple as needing a change of pace? (6:33)
– Was it frustrating to catch these online harassers, only to see them get minimal penalties? Were you involved in trying to acquire bigger penalties for these types of crimes? (9:43)
– When did you start the Law Office of Bradley Gross? Tell me about your mission statement and the types of cases you take on, especially those concerned with the cybersecurity sector. (12:00)
– What are some of the skills you learned as a hacker that help you most in your work as a lawyer? (15:21)
– What is one of the most usual cybersecurity-related cases you ever worked on? What are some of the most surprising things you’ve seen happen inside of a courtroom? (17:06)
– In the introduction, we mentioned that you are an international legal expert in the field of cloud computing transactions. What drew you to that area of expertise? (21:37)
– We’ve talked a lot this year about a skills gap in cybersecurity. Have you found a similar issue in security law? Are there enough security-focused lawyers out there, or is this an understaffed career path? (23:43)
– What are some of the biggest legal issues currently looming on the cybersecurity horizon that aren’t being addressed? (25:40)
– What is your take on the IT employee for the city of Lake City, FL who was fired after the city was forced to approve a half-million-dollar ransom payment? Do you feel this was justified, or did the city blame a systemic issue on a scapegoat? (27:30)
– What are the big issues in the area of Intellectual Property (IP) area at the moment? What are some things that security practitioners or enterprises don’t do properly to protect either IP? (31:45)
– Tell me about your own podcast, the Technology Bradcast. What is the focus of your podcast, and what have been your favorite episodes to record? (33:15)
– What piece of free legal advice would you like to give the cybersecurity industry as a whole or the people that work in it? (35:58)
– If our listeners want to know more about you or your law firm, where can they go? (35:58)

Additional Resources

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About the Cyber Work Podcast

Knowledge is your best defense against cybercrime. Each week on Cyber Work, host Chris Sienko sits down with a new industry thought leader to discuss the latest cybersecurity trends — and how those trends are affecting the work of infosec professionals. Together we’ll empower everyone with the knowledge to stay one step ahead of the bad guys.