Breaking Into Cybersecurity

Dreaming of a high-demand, secure career that protects the digital world, but unsure where to start?
This is your definitive guide to breaking into the thrilling field of cybersecurity, even with no prior experience! Industry expert Steve Regester reveals the exact roadmap you need to land your first cybersecurity job and build a resilient, rewarding future.In today's rapidly evolving digital landscape, the demand for skilled cybersecurity professionals is soaring. Cyber threats are more sophisticated than ever, making robust information security a critical concern for businesses worldwide. But how do you navigate this complex world and secure a lucrative role without an existing network or years of experience? Join us as Steve Regester, a seasoned veteran and renowned expert in the cybersecurity space, demystifies the entire process.
He breaks down common barriers, offering actionable advice on everything from mastering foundational IT security skills to advanced strategies for career progression and how to get a cyber security job.This comprehensive guide is an invaluable resource for anyone aspiring to build a successful career in IT security. Whether you're a recent graduate looking for a clear career path, considering a significant career change into tech, or simply curious about the world of ethical hacking and digital defense, this video is your ultimate blueprint.
Steve shares his invaluable insights on the diverse roles within cybersecurity, the most sought-after industry certifications like CompTIA Security+ or the highly respected CISSP, and crucial strategies for effective networking that will open doors.Discover how to craft a compelling cybersecurity resume, ace those challenging technical interviews, and position yourself as an indispensable asset in the global fight against cybercrime.
Steve emphasizes practical tips and real-world scenarios, ensuring you understand not just 'what' to learn, but 'how' to apply it. We'll explore entry-level cybersecurity jobs, discuss potential cyber security salary expectations, and provide a clear framework for continuous learning in a field that constantly evolves.
This isn't just about landing a job; it's about building a robust, future-proof cybersecurity career that truly matters. Empower yourself with the knowledge and confidence to make your cybersecurity career aspirations a reality. Don't miss out on these expert strategies from Steve Regester for breaking into cyber and securing your future in tech.
Ready to embark on your cybersecurity journey?
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🚀 ARE YOU PREPARED FOR THE SILENT FAILURE OF AGENTIC AI? Agentic AI introduces a critical new risk for enterprise security: silent failures. Unlike traditional breaches, these occur when AI agents operate within their given permissions but subtly deviate from their intended purpose, creating stealthy, hard-to-detect vulnerabilities. _________________________________________________ 🛡️ MITIGATING ADVANCED AI RISKS To safeguard your digital future, you must move beyond traditional risk management. This discussion covers: • Defining Silent Failures: Understanding how AI agents deviate without triggering standard alarms. • The Power of Diverse Perspectives: Why non-traditional backgrounds in psychology and politics are essential for AI governance. • Real-Time Mitigation: An inside look at how Geordie AI's "Beam" system is engineered to detect and neutralize these advanced threats. _________________________________________________ 🎙️ EPISODE HIGHLIGHTS & INSIGHTS Join hosts Renee Small and Christophe Foulon for a deep dive with Hanah-Marie Darley, co-founder of Geordie AI. Hanah-Marie leverages her background as a former US Government intelligence analyst to expose the unseen risks demanding immediate attention from CISOs. _________________________________________________ ⏳ TIMESTAMPS 0:00 AI's Silent Threat: Are CISOs Prepared for Agentic AI? 0:45 Meet Hanah-Marie Darley: From US Intelligence to AI Security Visionary 2:15 Uncovering 'Silent Failures' in Agentic AI: What Every CISO Needs to Know 14:15 Geordie AI's Beam System: Real-time AI Risk Mitigation Explained 26:15 Navigating Your Cybersecurity Career Path in the Age of AI _________________________________________________ 🔗 CONNECT & SUBSCRIBE • Newsletter: https://newsletter.breakingintocybersecurity.org • Listen On Spotify: https://open.spotify.com/show/16hs6zYtLa4iS4RTcyNF71 • Listen On Apple: https://podcasts.apple.com/us/podcast/breaking-into-cybersecurity/id1463136698 • Learn More: http://cpf-coaching.com _________________________________________________ 📚 FEATURED RESOURCES • Magnetic Hiring (Free Book): http://magnetichiring.com/book • The Cybersecurity Advantage: https://leanpub.com/the-cybersecurity-advantage • Hacker Inc. Mindset: https://www.amazon.com/Hacker-Inc-Mindset-Your-Career/dp/B0DKTK1R93/ #Cybersecurity #CISO #AgenticAI #GenerativeAI #InfoSec #aistatus Sponsored by CPF Coaching LLC - http://cpf-coaching.comThe Breaking into Cybersecurity: It’s a conversation about what they did before, why they pivoted into cyber, what the process was they went through, how they keep up, and advice/tips/tricks along the way.The Breaking into Cybersecurity Leadership Series is an additional series focused on cybersecurity leadership and hearing directly from different leaders in cybersecurity (high and low) on what it takes to be a successful leader. We focus on the skills and competencies associated with cybersecurity leadership, as well as tips/tricks/advice from cybersecurity leaders.Check out our books:The Cybersecurity Advantage - https://leanpub.com/the-cybersecurity-advantageDevelop Your Cybersecurity Career Path: How to Break into Cybersecurity at Any Level https://amzn.to/3443AUIHack the Cybersecurity Interview: Navigate Cybersecurity Interviews with Confidence, from Entry-level to Expert roleshttps://www.amazon.com/Hack-Cybersecurity-Interview-Interviews-Entry-level/dp/1835461298/

What does a 25-year cybersecurity career actually look like — and what does the CISO role require today when AI, regulatory pressure, and economic uncertainty all collide at once?Daniel Ayala is the Founder and Managing Partner of Secratic, a fractional CISO and Chief Privacy Officer consultancy. He's served as CISO at ProQuest, Interim CISO at Michigan State University, and today advises multiple SMBs simultaneously on security strategy, AI risk, and data privacy.In this episode, we talk about what it really takes to step into a CISO role, how the fractional CISO model works as a career path, why insider threat programs need a serious update in the AI era, and what practitioners pivoting into security leadership actually need to know.---**⏱ TIMESTAMPS**- 00:00 — Intro- 02:00 — Daniel's background and the 25-year journey- 08:00 — How Secratic was born: the fractional CISO model- 14:00 — Serving multiple organizations simultaneously- 19:00 — AI risk: what CISOs actually need to be doing right now- 25:00 — Insider threat in the age of workforce disruption- 30:00 — Privacy engineering vs. compliance thinking- 35:00 — CMMC, SEC disclosure, and what they mean for practitioners- 40:00 — How to position yourself for a CISO or vCISO role- 44:00 — Mentorcore: formalizing mentorship in cybersecurity- 47:00 — Advice for career changers breaking into cyber---**🔗 CONNECT WITH DANIEL**- LinkedIn: https://www.linkedin.com/in/danielaayala/- Secratic: https://secratic.com- The Great Security Podcast: https://greatsecuritydebate.net- Mentorcore: https://mentorcore.biz- Blog: https://danielayala.com**📚 BOOKS FROM OUR HOSTS**- Develop Your Cybersecurity Career Path: https://amzn.to/3443AUI- Hack the Cybersecurity Interview: https://www.amazon.com/Hack-Cybersecurity-Interview-Interviews-Entry-level/dp/1835461298/- Hacker Inc.: https://www.amazon.com/Hacker-Inc-Mindset-Your-Career/dp/B0DKTK1R93/- Magnetic Hiring (Renee): https://magnetichiring.com/book**🎤 BREAKING INTO CYBERSECURITY**Real conversations about pivoting into cyber — what you did before, how you got in, and how to keep growing.- 🌐 Website: https://breakingintocybersecurity.org- 📬 Newsletter: https://newsletter.breakingintocybersecurity.org- 🎧 Spotify: https://open.spotify.com/show/16hs6zYtLa4iS4RTcyNF71- 🍎 Apple Podcasts: https://podcasts.apple.com/us/podcast/breaking-into-cybersecurity/id1463136698- 💼 LinkedIn: https://www.linkedin.com/company/breaking-into-cybersecurity/#CyberSecurity #CISO #AIRisk #FractionalCISO #CareerChange #BreakingIntoCybersecurity #CyberLeadership #Privacy #InfoSec #CyberCareer

Peter Swimm started at a library computer desk. He ended up as a product owner at Microsoft and founder of his own AI security consultancy.

In this episode, Peter shares the real path — not the polished LinkedIn version. He talks about why working at startups changed how he thinks about learning, what it actually takes to balance security with user experience, and why conversational AI is opening a security attack surface most teams aren't prepared for.

If you're trying to break into cybersecurity from a non-traditional background, or you're already in tech and wondering what's next — this conversation is for you.

🔑 Key Takeaways:
→ Why baking security in from day one beats retrofitting it later
→ The "promiscuous learning" mindset that opens more doors than any cert
→ How conversational AI is changing the threat landscape right now
→ Career moves that come from taking on work outside your job description
→ What organizational culture really signals about your growth ceiling

📌 Chapters:
0:00 Intro — Peter's Cybersecurity Origin Story
0:58 First tech job and what the internet taught him
2:41 Transition into product ownership
5:03 Balancing security vs. user experience
9:19 Career advice: what actually works
16:00 The evolution of conversational AI
21:23 AI security: the challenges nobody talks about
26:42 Final thoughts and advice

🔗 Connect with Peter Swimm:
LinkedIn: https://www.linkedin.com/in/peterswimm/

🎙️ Breaking Into Cybersecurity:
Newsletter: https://newsletter.breakingintocybersecurity.org
Spotify: https://open.spotify.com/show/16hs6zYtLa4iS4RTcyNF71
Apple Podcasts: https://podcasts.apple.com/us/podcast/breaking-into-cybersecurity/id1463136698

📚 Books We Recommend:
Develop Your Cybersecurity Career Path: https://amzn.to/3443AUI
Hack the Cybersecurity Interview: https://www.amazon.com/Hack-Cybersecurity-Interview-Interviews-Entry-level/dp/1835461298/
Magnetic Hiring (Renee Small): https://magnetichiring.com/book

#CyberSecurity #CareerChange #BreakingIntoCybersecurity #AISecurity #CyberCareer

## Links Mentioned

- Peter's LinkedIn: https://www.linkedin.com/in/peterswimm/
- Toilville (Peter's Consultancy): [mentioned in episode]
- Breaking Into Cybersecurity Newsletter: https://newsletter.breakingintocybersecurity.org
- Christophe's CPF Coaching: https://www.cpf-coaching.com
- Renee's Book (Magnetic Hiring): https://magnetichiring.com/book

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## Listen & Watch

- YouTube: https://www.youtube.com/@BreakingIntoCybersecurity
- Spotify: https://open.spotify.com/show/16hs6zYtLa4iS4RTcyNF71
- Apple Podcasts: https://podcasts.apple.com/us/podcast/breaking-into-cybersecurity/id1463136698
- Newsletter: https://newsletter.breakingintocybersecurity.org

Breaking into Cybersecurity: Peter Swim's Journey from Libraries to Leading AI Conversations
https://www.linkedin.com/in/peterswimm/

In this episode of Breaking into Cybersecurity, we feature Peter Swim, the founder of the consultancy Toilville. Peter shares his unique journey into cybersecurity, starting from working at a library to becoming a product owner at Microsoft. He discusses the importance of security in tech and AI, the impact of working in startups, and how his experiences have shaped his career. Peter also provides valuable advice to juniors in the field, emphasizing the need to stay flexible, keep learning, and find the right organizational culture. This episode is a must-watch for anyone interested in tech, cybersecurity, and career development in the AI space.

00:00 Introduction to Peter Swim's Cybersecurity Journey
00:58 Early Career and Initial Interest in Tech
02:41 Transition to Product Ownership
05:03 Balancing Security and User Experience
09:19 Career Advice for Aspiring Professionals
16:00 The Evolution of Conversational AI
21:23 Challenges and Insights in AI and Security
26:42 Conclusion and Final Thoughts

Sponsored by CPF Coaching LLC - http://cpf-coaching.com
The Breaking into Cybersecurity: It’s a conversation about what they did before, why they pivoted into cyber, what the process was they went through, how they keep up, and advice/tips/tricks along the way.
The Breaking into Cybersecurity Leadership Series is an additional series focused on cybersecurity leadership and hearing directly from different leaders in cybersecurity (high and low) on what it takes to be a successful leader. We focus on the skills and competencies associated with cybersecurity leadership, as well as tips/tricks/advice from cybersecurity leaders.
Check out our books:
The Cybersecurity Advantage - https://leanpub.com/the-cybersecurity-advantage
Develop Your Cybersecurity Career Path: How to Break into Cybersecurity at Any Level https://amzn.to/3443AUIHack the Cybersecurity Interview: Navigate Cybersecurity Interviews with Confidence, from Entry-level to Expert roles
https://www.amazon.com/Hack-Cybersecurity-Interview-Interviews-Entry-level/dp/1835461298/
Hacker Inc.: Mindset For Your Career
https://www.amazon.com/Hacker-Inc-Mindset-Your-Career/dp/B0DKTK1R93/
About the hosts:
Renee Small is the CEO of Cyber Human Capital, one of the leading human resources business partners in the field of cybersecurity, and author of the Amazon #1 best-selling book, Magnetic Hiring: Your Company's Secret Weapon to Attracting Top Cyber Security Talent. She is committed to helping leaders close the cybersecurity talent gap by hiring from within and encouraging more people to enter the lucrative cybersecurity profession. https://www.linkedin.com/in/reneebrownsmall/Download a free copy of her book at magnetichiring.com/book
Christophe Foulon focuses on helping secure people and processes, drawing on a solid understanding of the technologies involved. He has over ten years of experience as an Information Security Manager and Cybersecurity Strategist. He is passionate about customer service, process improvement, and information security. He has significant expertise in optimizing technology use while balancing its implications for people, processes, and information security, through a consultative approach.
https://www.linkedin.com/in/christophefoulon/
Find out more about CPF-Coaching at https://www.cpf-coaching.com
Website: https://www.cyberhubpodcast.com/breakingintocybersecurity
Podcast: https://podcasters.spotify.com/pod/show/breaking-into-cybersecuri
YouTube: https://www.youtube.com/c/BreakingIntoCybersecurity
Linkedin: https://www.linkedin.com/company/breaking-into-cybersecurity/