HTB Stories #4 - John Hammond - The Making of a Pentester and Content Creator

·53 min·4 clips

John Hammond says you can hack without coding, but it's like walking when you could be running.

This Hack The Box AMA features host Soti (Red Runner) and guest John Hammond, a Senior Security Researcher at Huntress and a popular cybersecurity content creator. Hammond discusses his journey into cybersecurity and content creation, sharing practical advice for aspiring professionals. He explains his early alias "root of the null" and how he discovered Hack The Box around 2017 while on a university cyber team. Hammond details his current note-taking system using Obsidian and GitHub repositories for organizing information. He describes his basic video setup, which includes a Canon EOS R camera, an Audio-Technica AT2020 microphone, and OBS software. He admits to minimal editing, using Kdenlive for simple cuts, and expresses admiration for more produced styles like Network Chuck's. Hammond addresses the common feeling of missing prerequisite knowledge, advising learners to embrace not knowing everything and to study technologies by reviewing their official documentation. He compares Capture the Flag challenges to real-world penetration testing, noting similarities in problem-solving despite different environments. Hammond reveals the difficulty of balancing a full-time job with content creation, often sacrificing sleep and other priorities. For job interviews, he emphasizes communication, transparency, and understanding the interviewer's needs. His content creation process lacks a strict agenda, often involving exploratory "safari ride" videos where he learns in public. Hammond states that while programming is not strictly necessary for penetration testing, learning it allows you to "run" instead of "walk." To learn new topics, he recommends setting up the technology and reading its changelog or issue tracker. He discusses overcoming the initial challenge of having zero YouTube subscribers by consistently creating a backlog of content. Hammond collaborated with LiveOverflow early on to help grow his channel and mentions enjoying creators like Ash Fox, Optional, and CryptoCat. The tone is informal and conversational, with a friendly, fan-driven dynamic between the host and guest. This episode would appeal to aspiring penetration testers, cybersecurity students, and new content creators seeking honest, practical advice. Listeners looking for highly technical deep dives or structured tutorials might find it too broad or anecdotal.

As heard by us

Practical security thinking, with the rough edges of a live community session.

John Hammond's AMA keeps its focus on a plain but useful habit: start with the docs, learn how the software is built, and keep an eye out for the small version mismatch or misconfiguration that creates an opening.

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Why you'd press play

You want practical pentest advice from someone who talks through how to approach unfamiliar software.

Read the full recommendation in PlayNext →

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