Inspirational Influencers: Tailor Tolliver

Meet the Cyber Sec Queen of the digital world in our interview series: Inspirational Influencers

Her name is Tailor Tolliver but online, she is known as the ‘Digital Empress’. Tailor was born and raised in Baton Rouge, LA for 18 years until she moved to the DMV. Currently, she is on a journey to becoming a full-time Entrepreneur doing what she love. Tailor is very passionate about her career in Cybersecurity, helping others get in the field, as well as helping others brand themselves on social media to gain a great audience.

What got you into InfoSec? Were you always interested or did your path lead you here?

I moved from Louisiana in 2014 and started attending Montgomery College in Germantown, MD. I was originally convinced by my family to pursue dental hygiene as a career. During my second semester, I realized I wanted a career in technology after working on campus in our Digital Learning Center. There, I helped students with their tech classes and maintained the systems in the lab. Right next door, MC built a Cybersecurity lab for students to come and get experience working with security tools, study, and attend club meetings. This is how I initially got involved in Cybersecurity and eventually switched my major to that career field. My life was instantly aligned towards my purpose after doing this. I got my first tech internship as a Sharepoint Permissions Administrator while attending school and eventually got my first job as a Network Operations Analyst. I graduated with my associate's degree in Cybersecurity August 2017. Two years after obtaining my degree, I obtained my first position in security as a Security Engineer.

What exactly is InfoSec? People have this misconception that it’s hacking Mr.Robot style. Can you give us an overview of what your day on the job really looks like?

Lol!! To be honest, Mr. Robot is one of the few shows that demonstrates how the career field is. The show is very realistic when it comes to hacking. As far as my position in the career field, I’m not yet doing Mr. Robot style hacking but I’m on my way there. When I get into the office, I check the Information Security inbox for any alerts we may have gotten while not on the clock. I handle anything related to phishing emails and performing malware scans on infected systems. I am also in charge of our security metrics. So every week, I am analyzing how many of each threat we got and how long it takes us to remediate it to speed up our response time and better secure our network.

You built this really amazing community called ‘Digital Empire’, which I’m a member of. It’s such an organized, tight-knit community. Can you tell us:

1.) Why you started DE?


I started Digital Empire because when I originally started Twitter, I didn’t see a centralized community for all the blacks in tech I was finding on the platform. I’m not sure if that’s because I just wasn’t searching enough or what but I realized many of us were chatting and talking about similar topics and I got the idea to start the slack channel. They all were aboard for the movement and next thing you know, Digital Empire was officially started.

2.) The ups and downs of being a leader and advice to those looking to lead their own communities?

Well for one managing, different people, personalities, opinions, and backgrounds was something new for me. I kind of see the perspective of why companies are so lazy when it comes to promoting diversity. Being able to manage different people who come from different backgrounds is a bit hard and can honestly get messy. Especially when you start and don’t have any rules or regulations in place. You would think people older than you would have common sense when it comes to this kind of thing and spread wisdom but like we all know. Common sense isn’t so common anymore.

If you do want to start your own community I would be very cautious of who you allow in. Especially if you want to target a certain group that has beneficial qualities. Even if they are entry level in that specific expertise. I’ve grown to know that people who genuinely notice what you’re contributing and can appreciate your hard work beforehand usually are great candidates because they understand and respect the mission.

You have to be able to also let people go when they don’t vibe with the mission. Set ground rules, regulations, and boundaries beforehand so that people know that this is a no bullshit zone for disrespect and close-mindedness. Also, if you’re putting a lot of work into your community, providing resources, helping them get places in their career, think about monetizing it somehow. I’m currently in the process of monetizing the slack channel to bring better experiences and value to the current and future members.

Also, don’t forget to network and have fun with the new friends you have obtained.

3.) How you go about making sure DE stays structured and of value?

I talked with a few of the OG members in the group. I call this my vision board group:

Ari Hale - @WhutTheHale

Sarah - @NerdyAndNatural

Deja - @Empathic_Dev

Shakor - @SmithManny

Cedrick - @Medjay009

Pariss - @ParissAthena

We discuss rules and regulations, how we can better maintain the slack channel, what benefits we can incorporate, and how to keep the members experience great and fulfilling of their needs.

I also like to ask the non-OG’s as well. What would they like, what do they need, what could we do to make their experience better because the opinions of the community matter just as much as the vision board’s. They keep the community thriving and great for potential members.

4.) Any goals you may have for the future of DE?

I will definitely be turning it into a paid subscription for future members to be able to get the full experience. Merch will be coming as well, future meetups, and daily online vlogs to showcase talks of what each of us is achieving.  

5.) What are you learning right now pertaining to InfoSec? Feel free to leave recommendations or links to podcasts/reads/courses, etc.

I am currently refreshing my knowledge on just basic security concepts related to the Security+ cert. I think I’m currently going through imposter syndrome and I’ve been putting it off and taking on programming projects. The new approach I’m taking is showcasing and talking about my studies on Youtube and Twitch with my audience. I will be showing them the process up until I take my exam.


-Security+ Book (Darril Gibson’s Get Certified Get Ahead):

Darril Gibson Labs I will be completing on Youtube and Twitch:


-Cybrary Insider Pro Soc Analyst Labs:

6.) Last question :) Any advice to those seeking to get into the technology industry?

If you’re looking to thrive in the tech field, start by writing out what you love to do every day and why. This helps define your purpose and what value you could potentially bring to your employers or even clients. This helps narrow down what steps you need to take to get to where you want to be. Next, start researching and taking notes. It’s best to read and watch people doing exactly what you want to do. I would also recommend reaching out to those people and seeing if they can offer mentorship and advice for your specific journey. I would then advise you to create a blueprint and plan to get to your final destination. I like to refer to this as “Goal Alchemy”. You start with an interest, passion, or goal and cultivate it into a reality by implementing the right actions. It works every time if you stay consistent.

If you are looking to get help or mentorship in the cybersecurity career field, I offer a service that allows you to pick my brain and get resume critiques to help you land your first job in tech or maneuver into security. You can schedule a consulting call with me by clicking the link below and I would be more than happy to help you:

Follow Tailor, A.K.A Digital Empress on Twitter @DigitalEmpress

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