Success After CISO: How to Become Your Own Boss” with guest Aaron Bailey from The Missing Link

The New CISO

In this episode of The New CISO, Steve is joined by Aaron Bailey, CISO and co-founder of The Missing Link, to discuss what it takes to start your own security business.

Getting his first computer at eleven years old, Steve has always loved working with technology. Through explaining his professional journey, Steve shares the benefits and difficulties of being a cyber security founder. Listen to the episode to learn more about Aaron’s first jobs, joining an established startup, and success after being a corporate CISO.

Listen to Steve and Aaron discuss being your own boss and the challenges of being a co-founder:

Meet Aaron (1:32)

Host Steve Moore introduces our guest today, Aaron Bailey. Always a tinkerer with technology, Aaron explains how he started in cyber security, working his way up from entry-level positions.

After high school, Aaron struggled to find a job. After memorizing a manual per his father’s advice with a proposition of being quizzed, Aaron finally got hired at a computer shop, launching his career.

Why This Job (9:23)

Steve asks Aaron what the pay was like at his first job.

Through hard work, Aaron’s salary doubled within a year, and he was paid far more than other people his age.

Aaron’s Advice (11:52)

Although Aaron does not believe you need to be a staunch techie like himself for every job, what he looks for in an interviewee is passion, intelligence, perseverance, and dedication to the field.

Essential Aid (19:42)

Steve presses Aaron on the guide Essential Aid and how to explain it to others. Aaron defines it as containing the top mitigation strategies for cyber intrusions. To use it properly, you have to embrace automation.

Becoming a Founder (25:53)

When Aaron’s colleague Sam resigned from their corporate job, Aaron learned he was starting his own business and wanted Aaron to come with him.

Sam prompted Aaron to meet with the other partners, beginning the next stage of his CISO career. Aaron then shares the early weeks of joining the Missing Link and the challenges along the way.

A Non-Startup Startup (33:05)

The Missing Link was already a successful startup before Aaron joined, but they did not have a cyber security department. Aaron and Sam then became the company’s security professionals, which came with tremendous planning and organizing.

The Entrepreneur CISO (38:48)

Host Steve presses Aaron on his advice for other CISOs wanting to start their own businesses.

Aaron shares what was difficult about being a corporate CISO where you’re not always listened to compared to his position at the Missing Link. As a founder, you have increased responsibilities, but it’s much easier to ask for what you need for your team.

More Advice (44:03)

Aaron is still learning the shareholding and equity aspects of being a founder. Success once does not always mean success every time, so Aaron’s main advice is to always ask for advice.

Starting your own cyber security department is the most incredible interview of your career, but this path is not always easy.

A New CISO Founder (50:59)

To Aaron, being a CISO and a boss means having a seat on the board. Training new CISOs and watching them leave to start their own companies gives him the most joy.

Ultimately, the new CISO strives for the top and is not afraid to bring others up in this increasingly necessary field.

Links mentioned:

The Missing Link