#72 He Quit His Cybersecurity Job to Start a Pentesting Company ft. Tyler Ramsbey

#72 He Quit His Cybersecurity Job to Start a Pentesting Company ft. Tyler Ramsbey

In this episode of The Hacker’s Cache Podcast, I sit down with Tyler Ramsbey to discuss why he quit his cybersecurity job to build his own penetration testing company, Kairos Sec, and hacking education platform, HackSmarter. We dive into the reality of cybersecurity entrepreneurship, burnout, work-life balance, OSCP and PNPT certifications, AI in penetration testing, red teaming, OffSec’s “Try Harder” culture, and what it actually takes to succeed in offensive security. If you're interested in ethical hacking, penetration testing, cybersecurity careers, red teaming, or building your own business in tech, this episode is packed with honest insights and real-world experience from two professional pentesters.  Connect with Tyler Ramsbey on LinkedIn: https://www.linkedin.com/in/tyler-ramsbey-86221643/ Connect --------------------------------------------------- https://www.KyserClark.com [http://kyserclark.com/] https://www.KyserClark.com/Newsletter [https://www.KyserClark.com/Newsletter] https://youtube.com/KyserClark [https://youtube.com/KyserClark] https://www.linkedin.com/in/KyserClark [https://www.linkedin.com/in/KyserClark] https://www.twitter.com/KyserClark [https://www.twitter.com/KyserClark] https://www.instagram/KyserClark [https://www.instagram/KyserClark] https://facebook.com/CyberKyser [https://facebook.com/CyberKyser] https://twitch.tv/KyserClark_Cybersecurity [https://twitch.tv/KyserClark_Cybersecurity] https://www.tiktok.com/@kyserclark [https://www.tiktok.com/@kyserclark] https://discord.gg/ZPQYdBV9YY [https://discord.gg/ZPQYdBV9YY] Music by Karl Casey @ White Bat Audio Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information. Opinions are my own and may not represent the positions of my employer.

#71 Metasploit Creator: Why CVEs Won’t Save You in 2025 ft. HD Moore

In this episode of The Hacker’s Cache, Kyser Clark sits down with HD Moore, the legendary creator of Metasploit and CEO of RunZero, to discuss why relying on CVEs is putting organizations at risk in 2025. They unpack the truth about vulnerabilities that never get CVEs, the hidden dangers of SSH exposures, and why attackers are outpacing defenders through innovation. HD also shares bold takes on AI’s role in cybersecurity, the overreliance on tools and certifications, and why exposing version numbers might actually make systems safer. This episode is packed with insights every ethical hacker, pentester, and cybersecurity professional needs to hear. Connect with HD Moore: https://hdm.io/ [https://hdm.io/] Connect --------------------------------------------------- https://www.KyserClark.com [http://kyserclark.com/] https://www.KyserClark.com/Newsletter [https://www.KyserClark.com/Newsletter] https://youtube.com/KyserClark [https://youtube.com/KyserClark] https://www.linkedin.com/in/KyserClark [https://www.linkedin.com/in/KyserClark] https://www.twitter.com/KyserClark [https://www.twitter.com/KyserClark] https://www.instagram/KyserClark [https://www.instagram/KyserClark] https://facebook.com/CyberKyser [https://facebook.com/CyberKyser] https://twitch.tv/KyserClark_Cybersecurity [https://twitch.tv/KyserClark_Cybersecurity] https://www.tiktok.com/@kyserclark [https://www.tiktok.com/@kyserclark] https://discord.gg/ZPQYdBV9YY [https://discord.gg/ZPQYdBV9YY] Music by Karl Casey @ White Bat Audio Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information. Opinions are my own and may not represent the positions of my employer.

#70 From Teen Hacker to Professional Pentester: The Journey of Kyle Hoehn

In this episode of The Hacker’s Cache, Kyser Clark sits down with seasoned penetration tester Kyle Hoehn to unpack the journey from a curious teen experimenting online to a full time professional in offensive security. Kyle shares how early exposure to computer tinkering and real world troubleshooting shaped his path, why foundational IT knowledge still separates strong hackers from the rest, and what certifications actually helped him level up. We also explore the realities of learning cybersecurity today, navigating burnout, staying sharp while the AI wave reshapes the industry, and the role of passion and persistence in building a hacker career that lasts. If you want an honest look at how real pentesters grow, adapt, and thrive, this episode is for you. Subscribe to keep sharpening your edge in ethical hacking and cybersecurity. Connect with Kyle on Linkedin: https://www.linkedin.com/in/kylehoehn/ [https://www.linkedin.com/in/kylehoehn/] Connect --------------------------------------------------- https://www.KyserClark.com [http://kyserclark.com/] https://www.KyserClark.com/Newsletter [https://www.KyserClark.com/Newsletter] https://youtube.com/KyserClark [https://youtube.com/KyserClark] https://www.linkedin.com/in/KyserClark [https://www.linkedin.com/in/KyserClark] https://www.twitter.com/KyserClark [https://www.twitter.com/KyserClark] https://www.instagram/KyserClark [https://www.instagram/KyserClark] https://facebook.com/CyberKyser [https://facebook.com/CyberKyser] https://twitch.tv/KyserClark_Cybersecurity [https://twitch.tv/KyserClark_Cybersecurity] https://www.tiktok.com/@kyserclark [https://www.tiktok.com/@kyserclark] https://discord.gg/ZPQYdBV9YY [https://discord.gg/ZPQYdBV9YY] Music by Karl Casey @ White Bat Audio Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information. Opinions are my own and may not represent the positions of my employer.

#69 Why He Left a Safe Job to Hack Companies for a Living ft. Jim Schultz

In this episode of The Hacker’s Cache, Kyser Clark sits down with Jim Schultz, an OSCP-certified penetration tester, cybersecurity instructor, and consultant with over 15 years of experience. Jim shares his journey from taking apart his first family computer in the 90s to teaching hundreds of students and returning full-time to the world of ethical hacking and security consulting. They discuss how writing skills can make or break a pentester, what academia gets right (and wrong) about cybersecurity education, and why networking and mentorship are crucial for breaking into the field. If you’re pursuing the OSCP, CPTS, or a cybersecurity career, this episode is packed with practical advice and real-world insight.  Connect with Jim Schultz on Linkedin: https://www.linkedin.com/in/jamesrschultz/ Connect --------------------------------------------------- https://www.KyserClark.com [http://kyserclark.com/] https://www.KyserClark.com/Newsletter [https://www.KyserClark.com/Newsletter] https://youtube.com/KyserClark [https://youtube.com/KyserClark] https://www.linkedin.com/in/KyserClark [https://www.linkedin.com/in/KyserClark] https://www.twitter.com/KyserClark [https://www.twitter.com/KyserClark] https://www.instagram/KyserClark [https://www.instagram/KyserClark] https://facebook.com/CyberKyser [https://facebook.com/CyberKyser] https://twitch.tv/KyserClark_Cybersecurity [https://twitch.tv/KyserClark_Cybersecurity] https://www.tiktok.com/@kyserclark [https://www.tiktok.com/@kyserclark] https://discord.gg/ZPQYdBV9YY [https://discord.gg/ZPQYdBV9YY] Music by Karl Casey @ White Bat Audio Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information. Opinions are my own and may not represent the positions of my employer.

#68 Q&A: Why You’ll Fail in Cybersecurity if You Stop Learning

In this episode of The Hacker’s Cache Podcast, Kyser Clark answers real cybersecurity career questions from whether the OSCP or Hack The Box CPTS is better for breaking into pentesting, to how to renew your Security+ the smart way, and why cybersecurity isn’t for those who hate learning. He also exposes the truth behind bootcamps, entry-level job myths, and AI’s impact on the job market. If you’re trying to start or advance your cybersecurity career, this episode gives you the honest, experience-based advice you need to hear. Connect --------------------------------------------------- https://www.KyserClark.com [http://kyserclark.com/] https://www.KyserClark.com/Newsletter [https://www.KyserClark.com/Newsletter] https://youtube.com/KyserClark [https://youtube.com/KyserClark] https://www.linkedin.com/in/KyserClark [https://www.linkedin.com/in/KyserClark] https://www.twitter.com/KyserClark [https://www.twitter.com/KyserClark] https://www.instagram/KyserClark [https://www.instagram/KyserClark] https://facebook.com/CyberKyser [https://facebook.com/CyberKyser] https://twitch.tv/KyserClark_Cybersecurity [https://twitch.tv/KyserClark_Cybersecurity] https://www.tiktok.com/@kyserclark [https://www.tiktok.com/@kyserclark] https://discord.gg/ZPQYdBV9YY [https://discord.gg/ZPQYdBV9YY] Music by Karl Casey @ White Bat Audio Attention Listeners: This content is strictly for educational purposes, emphasizing ETHICAL and LEGAL hacking only. I do not, and will NEVER, condone the act of illegally hacking into computer systems and networks for any reason. My goal is to foster cybersecurity awareness and responsible digital behavior. Please behave responsibly and adhere to legal and ethical standards in your use of this information. Opinions are my own and may not represent the positions of my employer.