CyberWire Daily – “Eric Escobar: Collaboration is key.”

Date: December 21, 2025
Host: N2K Networks
Guest: Eric Escobar, Penetration Tester at SecureWorks

Episode Overview

This episode features Eric Escobar, a professional penetration tester, who shares his unconventional path into cybersecurity, the importance of curiosity, team collaboration, and practical advice for those aspiring to enter the industry. Eric draws engaging parallels between his early interests, civil engineering background, and current role “breaking into” companies to test their defenses. Listeners gain a candid look into pen testing, the diversity within cybersecurity teams, and actionable recommendations for career starters.

Key Discussion Points & Insights

From Lego Builder to Civil Engineer… to Penetration Tester

• Eric describes his lifelong curiosity and hands-on tinkering spirit, which shaped his professional journey.
  • “I grew up playing with Legos, building things, taking things apart.” (01:36)
• He initially chose civil engineering, earning both bachelor’s and master’s degrees and working professionally in the field.
• A serendipitous encounter—showing off “harmless” hacking to a friend’s family member, who was a cybersecurity director—led to his invitation into the field.
  • “Hold on a second, I can get paid to do what I just do for fun?” (01:49)
  • “How about I replace your engineering salary and you come work for me in the cybersecurity arena?” (03:02)

The Leap Into Cybersecurity

• Eric joined Barracuda Networks on the defensive (blue) team, then entered the “infosec” community—attending DEF CON and other conferences.
• Networked his way into the offensive (red) team at SecureWorks, which he calls his “dream job.”
• He likens pen testing to being “a bank robber for hire”—legally hacking a wide variety of targets to test their defenses.
  • “On any given day, I commit several thousand felonies… if I didn’t have permission.” (05:03)

The Value of Curiosity and Diverse Backgrounds

• Working in pen testing means frequent exposure to new environments and challenges; learning on the fly and asking, “What happens if…?”
  • “The best personality trait is curiosity.” (06:06)
• Eric stresses the diversity of paths into cybersecurity—his team includes RV salesmen, physicists, engineers, and more.
  • “There’s no one archetype of a hacker pen tester—completely across the board.” (06:52)

Why Collaboration is Key

• No one knows everything in this rapidly evolving field; diverse teams draw on their combined strengths.
  • “There’s nobody that knows everything… There’s no one that even knows 10% of everything.” (07:05)
• Effective problem-solving often involves reaching out to far-flung colleagues—for example, calling in the Japanese team for specific expertise.

Starting Out in Cybersecurity: Practical Advice

• Eric encourages newcomers to:
  • Listen to security podcasts to learn the lingo and industry topics.
  • Explore affordable online courses (e.g., ~$30 Udemy classes covering basics to pen testing labs).
  • Join bug bounty programs for hands-on learning.
  • Pursue certifications like the OSCP as a credential and gateway.
  • “Just start.” (07:58)
  • “If we can just teach people in a fun way, that’d be great.” (08:22)

Notable Quotes & Memorable Moments

• “I’m a bank robber for hire, and companies will come, hire SecureWorks to try and break in and steal everything that they hold dear.” (04:49)
• “On any given day, I commit several thousand felonies… if I didn’t have permission to do what I do.” (05:03)
• “The best personality trait is curiosity… There’s always that, like, huh, I wonder, if I did this, how would either the program, the hardware, the website, how would it respond?” (06:06)
• “Our team is filled with the most weird, ragtag, you know, group of people…[RV salesmen, physicists]…and I think the one that unifies all of us is we’re all curious about how things work.” (06:30)
• “There’s no one archetype of a hacker pen tester—it’s completely across the board.” (06:52)
• “Collaboration is absolutely key, especially when you don’t know everything.” (07:21)
• “Just start. Start listening to security podcasts just to learn the vernacular…then go after a certification, if you can.” (07:58)

Timestamps for Important Segments

• 01:31 — Eric’s intro, early interest in engineering, and start in civil engineering
• 03:02 — The chance encounter leading to cybersecurity
• 04:13 — Transition from blue team (defense) to red team (offense)
• 04:49 — Description of pen testing as “bank robber for hire”
• 06:06 — The importance of curiosity, diversity in backgrounds
• 07:05 — Collaboration and knowledge-sharing across global teams
• 07:58 — Career entry tips and learning resources

The Tone of the Conversation

Eric brings a conversational, approachable, and slightly humorous tone, making complex topics accessible. His analogies and personal anecdotes underscore a message of inclusivity and encouragement for anyone curious about cybersecurity.

Summary

Eric Escobar’s journey from civil engineer to pen tester is a testament to the value of curiosity, diverse backgrounds, and networking. He demystifies the pen testing role, emphasizes collaboration, and offers clear, actionable advice for breaking into cybersecurity. His story illustrates that there’s no singular path to success in this field—just a willingness to learn, experiment, and work alongside others.