Episode 15

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

Published on: 20th January, 2022

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

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About the Podcast

The CISO Diaries
The path to cybersecurity leadership is not a direct route and it's those divergent routes that create the amazing stories and histories of leaders who are driving security to keep businesses and people safe.

We’re Leah McLean and Syya Yasotornrat and we intend to give CISOs and cybersecurity professionals a place to be their authentic selves. These are the unedited stories told of how they got into cybersecurity, the real struggles they’ve persevered through, personal anecdotes that make them tick, and leadership advice based on experiences.

We aren't the kind of cybersecurity podcasts that focuses on the technologies, or recent incidents. We are the podcast that focuses on the people behind the headlines and the incredible diversity of experiences and backgrounds. (And it's not lost on us that we're two awesome female hosts)!

Let's face it: we are a cybersecurity tribe and we need all hands on deck!

We hope you enjoy our CISO diary entries.

After all, we're only human, right?

Special thanks to our sponsor, Cyber Future Foundation, a non-profit global cybersecurity executive leadership community, where leaders, thinkers, and futurists discuss and develop actionable guidance and frameworks for a trusted and safer world.

About your hosts

Syya Yasotornrat

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Syya is a tenured tech sales professional with her time at SonicWALL and Hewlett Packard (HPE) with some hospitality at the Walt Disney Company and IT recruitment experience in the mix. She is currently a podcast strategist and consultant, helping others to bring out their voice and legacy through podcasting. She loves to learn and talk about anything, so feel free to reach out!

Leah McLean

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Leah is Vice President, Cybersecurity Specialist at Mastercard. She is focused on implementing strategy and programs to evolve cybersecurity risk management approaches and cybersecurity awareness and training. She actively contributes in community working groups to advance cybersecurity risk management and third-party risk. Leah is also a mentor to candidates breaking into cybersecurity careers, and collaborates with employers to rethink their workforce and hiring strategies.
Leah is a co-founder at Whole Cyber Human Initiative, a non-profit focused on redefining how we identify, train, equip, advance knowledge, and build workforce development within IT and Cybersecurity. She also volunteers for Cyber Future Foundation, a non-profit driving workforce development initiatives and private and public sector collaboration.
Previously Leah held senior level roles as a cybersecurity practitioner at Armor, a cloud security company protecting data for SMB and mid-market customers, Apstra (acquired by Juniper Networks), A10 Networks and Cisco Systems. Leah serves on the Board of Advisors for Cloud Defense, Inc., a breach visibility cloud security startup and is on the board for the Cloud Security Alliance North Texas Chapter.
Leah holds a bachelor’s degree in Political Science, with an emphasis in International Relations from the University of California, Santa Barbara. She is an active outdoor junkie always chasing adventure.