- The PWN
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- The PWN: Issue 018
Welcome to another edition of The PWN! I hope you are doing well. I am excited about Hack Space Con and BSides Tampa. I am speaking at both conferences. I am super excited to be hosting my first conference CYBR.HAK.CON. on May 27, 2026 in partnership with CYBR.SEC.Community. CYBR.SEC.Community founded HOU.SEC.CON., which rebranded as CYBR.SEC.CON. CYBR.HAK.CON. is taking place at the Plano Event Center in Plano, TX. Our speakers include keynotes Jason Haddix and Dustin "Wirefall” Dykes, and featured speakers Justin “Hutch” Hutchens and Tim Medin. The full agenda will be released soon, and you can get tickets here: https://www.xcdsystem.com/cybrseccommunity/attendee/index.cfm?ID=3ZiIV4j. Use the code HAK_26MRF for $75 off the orginal ticket price.
Upcoming Events
I always love connecting with people in my network and my podcast listeners. |
I am speaking at the upcoming events: |
May 8 - 9 - Hack Space Con https://www.hackspacecon.com/ - Kennedy Space Center, FL |
May 16 - BSides Tampa https://bsidestampa.net/ - Tampa, FL |
May 27 - CYBR.HAK.CON. https://cybrhakcon.com - Plano, TX |
July 10 - Boardwalk Bytes - https://boardwalkbytes.org/ - Atlantic City, NJ |
Season 4| Episode 16: From Listener to Pentester: How Zach Tackett Broke Into Cybersecurity
Breaking into cybersecurity is not about taking the perfect course or collecting certifications. It is about persistence, hands-on experience, and putting yourself out there.
In this episode of The Phillip Wylie Show, I sit down with Zach Tackett, someone who started as a listener of the podcast and is now working as a pentester at Secure Ideas.
Zach’s journey is one a lot of people will relate to. He grew up in a blue-collar household, didn’t have early access to technology, and only got his first real exposure to computers in high school. Like many of us, he started by fixing infected machines at home without fully understanding what he was doing. That curiosity turned into a passion.
He originally planned to go into game design, but after getting into computer science and taking a few security classes, everything changed. That led him down the cybersecurity path, eventually earning a role supporting NASA and later transitioning into offensive security.
One of the most interesting parts of his story is how he landed opportunities. Not through traditional applications, but through networking. Conversations on Twitter turned into real job leads. Meeting people at conferences opened doors. Even this podcast episode started because he was actively engaging with the content.
Zach also shares what actually helped him succeed:
Building hands-on labs instead of relying only on theory
Practicing on platforms like Hack The Box
Learning to think through problems instead of following walkthroughs
Being willing to adapt when tools fail
Reaching out to people in the industry without hesitation
He also makes an important point that a lot of people need to hear. You do not need a degree to succeed in cybersecurity. Some of the smartest people he has worked with do not have one. What matters is your ability to do the work.
Another standout moment is when Zach completed a pentesting challenge using only browser tools because his lab environment broke. That is the hacker mindset in action. Adapting, finding another way, and getting the job done.
If you are trying to break into pentesting or level up your skills, this episode is packed with practical advice you can actually use.
👉 Watch or listen to the full episode here:
Subscribe on YouTube or your favorite podcast platform (https://phillipwylieshow.com/subscribe).
Cheers!
Phillip Wylie