Josh Mason - CEO & Founder of Cyber Supply Drop; Red Team Instructor at INE; Retired Air Force Pilot

The CISO Diaries

Josh Mason is the CEO and Founder of Cyber Supply Drop. He runs giveaways that provide participants with free vouchers for training and certification exams. He’s also a Red Team instructor at INE, a huge advocate and mentor to veterans breaking into cyber, and a very active contributor in the community.

He’s also an instructor for WithYouWithMe, an Australian company which helps people without a tech background get jobs in tech, and on the Board of Advisors for non-profit, Whole Cyber Human Initiative.

Josh sheds light on the best, most cost and time efficient ways to break through the barriers in the industry.

Josh has 10 years of military experience, as an Air Force pilot and cyber warfare officer.

His work at the 1 Special Operations Communications Squadron ensured mission continuity on the busiest Air Force Special Operations Command base and at deployed locations across the globe.

As a cybersecurity instructor for Jacobs at the Department of Defense Cyber Crime Center, Josh trained hundreds of US DoD cybersecurity operators and special agents in Cyber Threat Emulation, Digital Forensics and Incident Response, and Threat Hunting.

As a cybersecurity evangelist, Josh points prospective and active cyber professionals at valuable training and resources, with a focus on free and highly-accessible content.

He’s a Cyber Warrior, husband and father of two little ones.

Diary Highlights:

0:00 - Intro & Background

· Training background, Military

· Mentor

· WithYouWithMe - Mentor, training up veterans and mil spouses to get into jobs

· Cyber Supply Drop, Red Team Instructor for INE

· Transitioning from Military to Civilian Life and job

· Leader suggested that cybersecurity wasn't for him

· Went into teaching on operations with some cybersecurity, loved instructing

· Once leaving the military, didn't have an idea on what to do, signed with DOD SkillBridge Internship.

· Learned Project Management

· Looked at LinkedIn connections - Reached out to a connection from Navy and had commonality of going through program.

10:00 - Speaking and Engaging

· Special forces training helping to interview

· Shout out to military veterans

· Taught critical thinking skills, instructions vs giving goal to solve

· Similar to business, give the team to solve their own problem and empower

· Veterans are used to being empowered and to think. If there is a failure, it's ok to ask for help. Failure is part of the experience to learn.

· Failure is acceptable

· Josh's story: In Afghanistan, plane wasn't starting, looked at the challenges with engine problems. In the end, worked through the process.

22:00 - Teams & CISO roles

· Talks about the ideal teams

· The newness of CISO role and role of cybersecurity

· There is an older school

24:50 - Being Told No

· When the Commander told him to reconsider cybersecurity, was no longer a pilot

· Josh realized he wasn't doing his "dream job"

· Looked at the limitations of being effective and limitations of empowerment in military hierarchy

· SkillBridge was effectively a Leadership Laboratory

· Helpful to look at building the next generation leadership

29:00 - Applying to Parenthood

· Primary goal is to be father and husband first

· All activities is to drive family harmony

· Met his wife there and she's accomplished in her own right

Final Thoughts:

Give your people a chance to grow and fail. Accept the responsibility and don’t just give them the crown jewel and let them fail so it is easier to learn. Know that you are going to fail.

LinkedIn: https://www.linkedin.com/in/joshuacmason/

Twitter: https://twitter.com/joshua17sc