Cybersecurity Mentors Podcast

On this episode of the Cybersecurity Mentors Podcast, we sit down with Jeffrey Wheatman to break down one of the most underrated skills in cybersecurity: storytelling. 
Jeffrey shares how he built a career helping CISOs communicate more effectively with boards, executives, and teams by shifting away from charts and data toward stories that resonate and drive action. 
We explore why storytelling is a skill anyone can learn, how it applies to leadership, presentations, and interviews, and why the best cybersecurity communicators think more like mentors than heroes. 
In this episode, you’ll learn:
Why data alone often fails to move executives and boards
How storytelling improves presentations, interviews, and leadership communication 
The “Yoda vs. Luke” mindset shift for cybersecurity professionals 
Practical tips to craft, structure, and deliver memorable stories 
If you want to influence decisions, lead effectively, and stand out in your career — this episode will change how you communicate. 
Come hang out with us in the Cybersecurity Mentors Skool community. It’s free to join.

Most cybersecurity candidates prepare the wrong way for interviews.
They focus only on technical questions… but hiring managers are evaluating something completely different.
In this episode, we break down exactly what cybersecurity hiring managers look for during interviews — based on real hiring experience building and managing security teams.
You’ll learn:
• What hiring managers evaluate in the first 10 minutes
 • The biggest mistakes candidates make during interviews
 • Why personality and soft skills matter more than you think
 • How to prepare using the job description the right way
 • What questions you should ask to stand out
 • How to position yourself even if you’re entry-level
If you’re trying to land your first cybersecurity job — or your next one — this episode will help you prepare with confidence.
This isn’t theory. This is real advice from cybersecurity hiring managers. 
Come hang out with us in the Cybersecurity Mentors Skool community. It’s free to join.

In this episode, we interview Matt Osegard, a retired FBI Supervisory Special Agent with over 21 years of experience in cybersecurity and counterintelligence investigations.
Matt shares his journey from Army officer and classroom teacher to leading cyber and counterintelligence operations inside the FBI. We discuss:
What training at Quantico is actually like
How agents get assigned to cyber and counterintelligence roles
The evolution of cybercrime and ransomware investigations
The investigative mindset required to solve complex cyber cases
What happens when an organization calls the FBI during a cyber incident
How the FBI works with international partners to pursue threat actors across borders
Advice for anyone considering a career as an FBI Special Agent
If you’re interested in cybersecurity careers, federal law enforcement, counterintelligence, or how cybercrime investigations really work, this episode gives you an inside look at the mission and the mindset behind the Bureau’s cyber operations.

Come hang out with us in the Cybersecurity Mentors Skool community. It’s free to join.

If you’ve been applying for cybersecurity jobs and hearing nothing back… this might be why.
In this episode of the Cybersecurity Mentors Podcast, two active cybersecurity hiring leaders break down what’s actually preventing candidates from getting interviews — based on real hiring experience and large-scale resume data analysis.
We cover:
How to write resume bullets that show impact (not just responsibilities)
Why measurable results massively increase callback chances
The biggest LinkedIn mistakes we see from entry-level candidates
How to tailor your resume for SOC, Cloud, or GRC roles
Why “spray and pray” job applying no longer works
How portfolios, GitHub, and even short videos can help you stand out
Competition in cybersecurity is rising — and small details now make the difference between getting ignored and getting interviews.
If you want honest hiring manager feedback, this episode is for you. 
Come hang out with us in the Cybersecurity Mentors Skool community. It’s free to join.

Cybersecurity doesn’t just have a talent gap — it has a leadership gap.
In this episode of The Cybersecurity Mentors Podcast, we sit down with Dave Berke, retired Marine Corps officer, former Top Gun instructor, and Chief Development Officer at Echelon Front, to talk about why leadership is missing across IT and cybersecurity — and why technical excellence alone is no longer enough.
Dave shares lessons learned from combat aviation, military leadership, and years of teaching leadership alongside Jocko Willink — and explains why leadership is a skill that must be learned, not a trait you’re born with.
In this episode, we cover:
Why the “best technician” often struggles as a leader
The leadership gap across cybersecurity and IT teams
Why leadership isn’t about titles or authority
How introverts and technical professionals can still become strong leaders
The role of humility, ownership, and teamwork in healthy security teams
How to lead from any position — even without a leadership title
Why developing leaders is the ultimate test of leadership
If you work in cybersecurity, IT, engineering, or any technical field — this conversation will change how you think about your career growth. 
Come hang out with us in the Cybersecurity Mentors Skool community. It’s free to join.