#52 The Ultimate Hacking Wisdom Compilation

The Hacker's Cache

This episode marks one year of The Hacker’s Cache.
To celebrate, I’ve compiled the most powerful, insightful, and thought-provoking moments from every single episode of Season 1, all 52 of them, in one back-to-back highlight reel.

This isn’t just a recap. It’s a front-row seat to the best hot takes, bold opinions, unique insights, and raw truths from some of the most driven minds in cybersecurity. Whether you're a red teamer, aspiring hacker, or cybersecurity professional looking for real-world advice, this episode is packed with the type of wisdom you don’t usually get in one place.

You'll hear perspectives on:

• Breaking into cybersecurity without a degree
• Penetration testing vs. vulnerability assessments
• Active Directory labs and red teaming tips
• AI in cybersecurity (real hype or real threat?)
• The OSCP, burnout, bootcamps, and job hunting
• Soft skills, report writing, and real hacker mindsets
• And why the Nigerian prince still works in 2024

If you’re new to the show, this is the perfect place to start.
If you’ve been here since the beginning, this is the ultimate rewind.

Welcome to Season 2. Let's get to work.

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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.

Chapters

1. Introduction (00:00:00)

2. #0 Security Is Not Everybody’s Responsibility (00:00:42)

3. #1 Do Something Great in the World ft. Joshua Ragland (00:01:10)

4. #2 Transition From Pentester to Senior Pentester ft. Adolfo (Val) Vask (00:01:40)

5. #3 Best Way to Learn Active Directory Hacking Skills ft. Robert O’Connor (00:02:07)

6. #4 A Vulnerability Assessment Isn't a Pentest ft. Kristofer Johnson (00:02:35)

7. #5 Pay It Forward ft. George Raileanu (00:03:12)

8. #6 Is AI Going to Cause Bad Stuff? Of Course, Everything Does ft. Mike Finkel (00:03:40)

9. #7 Think Outside the Box to Land First Pentesting Job ft. Ryan Daub (00:04:10)

10. #8 Cybersecurity Is a Beautiful Field: There's People That Don't Like Me ft. Aaron Tra (00:04:40)

11. #9 Red Teaming & Malware Development ft. Nathan Rice (00:05:10)

12. #10 Breaking into Cybersecurity: Tips from a Pro ft. Jake Mayhew (00:05:40)

13. #11 Stay Creative Together: Insights from Nouha Ben Brahim (00:06:11)

14. #12 Why OSCP Might Not Be Worth It - A Surprising Take by Evan Isaac (00:06:43)

15. #13 Hacking Time: Real World Skills They Don't Teach You | Trent Darrow (00:07:13)

16. #14 Social Engineering Unleashed: DEF CON Insights from Jacob Villarreal (00:07:43)

17. #15 From Zero to Hero: How Anyone Can Succeed in Cybersecurity (00:08:14)

18. #16 Why Cybersecurity Is Stressful and How to Succeed with Opeyemi Kolawole (Hacking Insights) (00:08:43)

19. #17 Unpacking Bug Bounty Strategies with RootSploit: Zero Days, Recon, and Vulnerabilities (00:09:11)

20. #18 16 Years in IT, Now a Fortune 100 Pentester: 0xD1CE Shares His Journey (00:09:42)

21. #19 Beating the Odds in Cybersecurity: What It Really Takes ft. James Scott (00:10:10)

22. #20 What it REALLY Takes to Pass OSCP (and What They Don’t Tell You) ft. Trent Miller (00:10:44)

23. #21 Unpacking AppSec: Lessons and Insights with Jonathon Fuller (00:11:15)

24. #22 Q&A: Cybercrime, Certifications, and Sacrifice in Cybersecurity Careers (00:11:45)

25. #23 SOC Analyst Life: Challenges & Secrets from Trent Williams (00:12:07)

26. #24 Building a Career Together: Lessons from Clint & Si The Hackers (00:12:29)

27. #25 Beyond Compliance: How Hackers Think and What Companies Miss ft. Albert Corzo (00:12:54)

28. #26 Q&A: The Certification Everyone Asks For (Is It Overrated?) (00:13:18)

29. #27 Red Team Reality: Building the Hacker's Edge ft. Mike Ortiz (00:13:39)

30. #28 Outwork the Competition: Winning the Cybersecurity Career Game (00:14:07)

31. #29 InfoSec Pat’s Journey From Network Engineer to Cyber Mentor (00:14:46)

32. #30 Uncovering a $200M Fraud Ring with David Taxer (00:15:14)

33. #31 Q&A: Are Tech Giants Planning to Replace Us with AI? (00:15:41)

34. #32 From Physical Security to Penetration Testing: Paul Nieto III's Journey (00:16:16)

35. #33 Are Cybersecurity Bootcamps a Scam? ft. Keith Coleman (00:16:46)

36. #34 Why Top Pentesters Make More Money (Most Ignore This Skill) ft. Spencer Alessi (00:17:10)

37. #35 Q&A: The Harsh Truth: You NEED to Code for Cybersecurity Mastery (00:17:43)

38. #36 The OSCP Won’t Save You ft. Tyler Ramsbey (00:18:17)

39. #37 He Hacked for 1000 Days Straight: Here’s How It Landed Him a Cybersecurity Job ft. Constantinos Kaplanis (00:18:45)

40. #38 Fired or Freed? Turning a Cybersecurity Layoff into Your Next Big Break w Justin Mahon (00:19:01)

41. #39 Q&A: Struggling with Burnout? Here’s Why It Might Be a Good Thing (00:19:22)

42. #40 Proof You Don’t Need a Degree to Succeed in Cybersecurity ft. Zach Winchester (00:20:01)

43. #41 How to Actually Become a Great Pentester (00:20:34)

44. #42 Certifications, College, or Bootcamps — What’s Worth It in Cybersecurity? ft. Channa Rajaratne (00:21:18)

45. #43 Grind Now, Relax Later: The Harsh Reality of Breaking Into Cybersecurity ft. Matthew Younker (Zumi Yumi) (00:21:53)

46. #44 How to Hack What No One Teaches ft. Noah Pack (00:22:28)

47. #45 OSWA Grind: 24 Hours. No Sleep. One Last Flag ft. Pratham Shah (00:23:00)

48. #46 She Started Coding at 13 and Never Looked Back ft. Betta Lyon Delsordo (00:23:31)

49. #47 Q&A: Feel Lost Watching Hacking Videos? Listen to This (00:24:00)

50. #48 He Got Hired Without Knowing the Answer: Here’s Why ft. Michael Kim (00:24:27)

51. #49 He Found Vulnerabilities in His Own Code: Then Made a Career Out of It ft. John Kounelis (00:24:55)

52. #50 No OSCP. No Degree. Still Landed a Red Team Job ft. Richie Vinson (4NU81X7H3H4CK3r) (00:25:34)

53. #51 Q&A: Why YouTube Took Down My Wi-Fi Hacking Video (00:26:07)