Q&A: Larry Whiteside Jr.

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Larry Whiteside Jr. has two passions: Cybersecurity and basketball. At 6’6” tall, his dream job as a basketball coach isn’t all that crazy. He has two jobs, six children, over 60 pairs of (size 16) shoes and one piece of advice to industry n00bies: “Know your worth, don’t devalue yourself because someone else does and don’t ever let someone offer you less than you deserve” 

What’s the most important lesson you’ve learned?

Transparent conversations are a part of business, and we shouldn’t shy away from them, regardless of how hard they may be. This point applies to life as well. You just have to be tactful and look at things through a different lens in order to understand the other person’s perspective.

When I was a CISO, I decided to go against my boss’s decision in a public meeting because it fundamentally went against my morals as a security executive. I didn’t do it tactfully, which created a rift with him that took a while to repair.

What’s the most misunderstood thing about information security?

That the field doesn’t want to allow IT people or the business to do things. We are not ‘the office of no.’ We just want the business to do things securely and think of those things at the idea stage of a business initiative.

Larry Whiteside Jr.
Larry Whiteside Jr.

Tell me in one sentence what your job is about

Technically, I have a couple of jobs. The job that feeds my family is holding responsibility for all aspects of technology strategy for internal and external customer-facing technologies.

The job that feeds my soul is the responsibility for driving the message of a need for diversity in the cybersecurity community while creating a strategy to achieve the diversity goal.

 What’s your biggest professional regret?

I regret that I did not know my value earlier in my career. As a black man in the industry of cybersecurity, coming from an underserved community, knowing my value was not something I knew.

What’s the best thing about your job?

Every day I have an opportunity to face a new challenge that did not exist the day before.

What’s the worst thing about your job?

There is no start or stop time. I am never off.

What’s your proudest achievement?

I am an extremely proud father. I have six children, but eventually, it will be eight once I marry my soulmate. 

If you could change one thing about the information security sector, what would it be?

To provide an easier pathway for more diverse people to enter the field.

What’s your dream client project?


Bio: Larry Whiteside Jr. is a veteran CISO, former USAF officer and thought leader in the cybersecurity field. Larry currently serves as the chief trust officer and chief technology officer at CyberClan and is the co-founder, president and member of the board of directors at the non-profit association International Consortium of Minority Cybersecurity Professionals (ICMCP). In 2009, Larry founded Whiteside Security. Larry received his bachelor of science degree in computer science at Huston-Tillotson University.

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