Aaron Portnoy learned to hack from anonymous strangers on IRC — not in a classroom. Now he's a Hacker Fellow at Dartmouth and one of the world's leading offensive security researchers.

In this episode of WakeUpX, Aaron breaks down the free, practical roadmap he'd give anyone trying to break into cybersecurity today:

- Why Capture the Flag contests are the single best starting point

- How to build real skills without a home lab or college tuition

- The role of conference talks (published free on YouTube) in self-education

- Why curiosity beats credentials every time

Whether you're a student, a career switcher, or just security-curious — this episode is your entry point.

Full episodes: www.wakeupxpodcast.com

Aaron's site: aaronportnoy.com

Mindgard: mindgard.ai

Topics: cybersecurity career, CTF, capture the flag, offensive security, free learning, hacking, infosec, Aaron Portnoy, Mindgard, Wake Up X podcast

What if the AI powering your company is about as hackable as a 1999 web server?

That's the uncomfortable reality Aaron Portnoy — offensive security legend, co-founder of Exodus Intelligence, and Head of Research & Innovation at Mindgard — lays out in this episode of WakeUpX.

We cover:

- Why AI security mirrors the early internet era

- The "hamster wheel" of repeating security trends

- The state of AI guardrails (and why they're not enough yet)

- How to break into cybersecurity with no degree or certifications

- Why curiosity is the most dangerous skill in offensive security

Aaron has spent 20+ years at the frontier of vulnerability research — from running the Zero Day Initiative to architecting the Pwn2Own competition, building Randori's R&D (acquired by IBM), and serving as the inaugural Hacker Fellow at Dartmouth College. He's now applying that offensive lens to AI systems at Mindgard.

Full episodes: www.wakeupxpodcast.com

Connect with Aaron: aaronportnoy.com | mindgard.ai/authors/aaron-portnoy

Topics: AI security, cybersecurity career, offensive security, zero day research, AI red team, hacking, prompt injection, Pwn2Own, Mindgard, WakeUpX

Efren L. Salazar introduces “Decode: The Wake Up X Career Blueprint,” a free educational map for going from zero experience to executive-level thinking without needing a degree or connections, built from Wake Up X Podcast guest stories and public research with clear disclaimers. The blueprint outlines a six-level path (entry, fit, breadth, differentiation, ownership, executive), a career value stack (curiosity, technology, communication, business/sales, leadership), and practical frameworks including the Curiosity Compass, TRACK applications, STAR storytelling, VALUE negotiation, the reputation loop, documentation wheel, decision filter, connection flywheel, executive dashboard, and quarterly career health score. It covers networking and GRC foundations (OSI model, major standards like NIST CSF, ISO 27001, PCI DSS, HIPAA, GDPR, SOC 2, CIS Controls), home lab and automation projects, certification roadmaps, cross-training (including AI literacy), business ownership lessons, networking via chapters and events, and ways to connect with the community and podcast.00:00 Decode Blueprint Intro00:45 Disclaimer and Sharing02:05 Wake Up X Movement03:13 Why This Exists04:18 Networking and GRC Basics08:29 Start Here Levels09:57 Opportunity by Numbers13:00 Mission and Remix15:42 Career Value Stack17:03 Six Level Map19:24 Four Beliefs Mindset22:23 Efren Origin Story31:18 Level One Breaking In35:13 Home Lab Projects40:52 Cert Roadmap43:22 Creators and Mentors46:12 Level Two Find Lane47:27 Curiosity Compass Quiz50:38 Pivot Panel and Guests51:38 Guest Links Directory56:36 Rising Cohort Profiles59:52 Cross Training Advantage01:01:00 AI Literacy Playbook01:02:53 TRACK Job Search System01:04:42 STAR VALUE Negotiation01:08:05 Multiplier Skills Proof01:10:38 Reputation Loop Portfolio01:13:07 Think Like An Owner01:17:18 Independent Consultant Math01:20:34 Staying Valuable After Layoffs01:24:34 Executive Thinking Tools01:28:11 Quarterly Career Review01:29:59 Real Rooms Networking Flywheel01:33:02 Next Steps And Resources01:34:11 Glossary Quick Reference01:41:09 Blueprint Library Wrap Up

In this episode of the Wake UP X Podcast, host Efren Salazar sits down with Devin Prasad for one of the most honest and thought provoking conversations about focus, identity and what it really means to grow on your own terms.

Devin opens up about one of the boldest and most underrated decisions of his career. Leaving Facebook at 20 years old and never going back.

His generation grew up with MySpace at 13 and 14. They navigated some of the most formative years of their lives with social media woven into their daily experience. And most people never stopped to ask the most important question.

Who am I without this thing?

Devin asked it. And the answer changed everything.

🔹 He got more done.🔹 He removed the distraction.🔹 He created the space to figure out who he actually was and what he actually wanted.

And in the 10 years that followed he earned 9 promotions.

But this episode goes deeper than social media. Devin and Efren get into something that touches every area of life. The idea that life is not linear. That the template society hands us, go to school, get a job, get married, follow the steps, was never designed for multidimensional people living multidimensional lives.

The answer is never just this or that. Sometimes it is both. Sometimes it is neither. Sometimes it is a third option nobody gave you permission to consider. The real work is finding yourself in the process and not losing yourself to the noise along the way.

🔹 Think of it like driving. You cannot floor it everywhere. Sometimes you have to slow down, make a turn, do some maintenance and then keep going. Progress is not always full speed. Sometimes the smartest move is knowing when to pause.

Devin is back on Instagram and LinkedIn now. But he uses them intentionally as tools for business and marketing. The difference is he owns the tool. The tool does not own him.

This episode is for anyone who feels like they are running someone else's race and is ready to get back to themselves.

🎙️ Host: Efren Salazar👤 Guest: Devin Prasad | Network Engineer & Cybersecurity Professional🎙️ Show: Wake UP X Podcast

🔗 Full Episode: https://www.wakeupxpodcast.com/the-full-career-story-nobody-tells-you-about-getting-into-itcyber-devin-prasad/

Episode Length: ~30 minutes

In this episode of the Wake UP X Podcast, host Efren Salazar sits down with cybersecurity professional Devin Prasad for a conversation about generational perspective, strategic thinking and what it really takes to pursue one of the hardest certifications in the industry.

Efren and Devin open up about what it means to be part of the generation that witnessed the full transformation of technology in real time. Not the generation before them that only knew the old way. Not the generation after them that inherited a world where everything just works. But the generation in between that saw every single step of the transition. Carburetor to fuel injection to Tesla. On-prem to cloud. Analog to fully digital.

That perspective is rare. And it shaped every career decision Devin has ever made.

Including his next certification move.

After earning his SSCP Devin planned to go straight for the CISSP. Then he visited the ISC2 website and saw something that stopped him cold.

The CISSP had hundreds of thousands of holders. It had been around for decades.

The CCSP, Certified Cloud Security Professional, had only been available for two years. And at the time fewer than 2000 people in the entire world had earned it.

Devin registered for the CCSP immediately.

🔹 Cloud was clearly the future of the industry.🔹 Almost no one had this certification yet.🔹 Getting in early meant positioning himself ahead of the curve before the crowd arrived.

But the CCSP was not going to be easy. It is not a technical practitioner exam. It is managerial and situational requiring strategic decision making at an executive level. And because cloud was still relatively new at the time the content was a hybrid of both worlds. Devin calls it the hardest test he ever took.

So he locked in.

🔹 1500 practice questions completed before exam day.🔹 YouTube videos and LinkedIn Learning resources studied thoroughly.🔹 Luke Ahmed's Think Like a Manager used as a core study resource.🔹 12 full weeks of aggressive focused preparation.🔹 ISC2 Peace of Mind voucher purchased giving him two attempts for an extra $200.

He went in prepared. He went in strategic. And he went in with a mindset built from years of watching the industry evolve from the very beginning.

🎙️ Host: Efren Salazar👤 Guest: Devin Prasad | Network Engineer & Cybersecurity Professional🎙️ Show: Wake UP X Podcast

🔗 Full Episode: https://www.wakeupxpodcast.com/the-full-career-story-nobody-tells-you-about-getting-into-itcyber-devin-prasad/

Episode Length: ~32 minutes

In this episode of the Wake UP X Podcast, host Efren Salazar sits down with network engineer Devin Prasad for a conversation about one of the most important mindset shifts in any tech career.

Showing up hungry before anyone is paying you to be.

Devin breaks down why bootcamps and certifications only get you so far. The real growth comes from volunteering, connecting with the right people and doing the work before the title and the pay catch up. Because if you are hungry people will feed you. And if you are not hungry you will never eat at all.

That mindset started changing how he approached everything.

🔹 Not just being technically sound but understanding how to implement things cleanly.🔹 How to transition systems with zero downtime.🔹 How to prepare for what could go wrong before it does.

His leads noticed. And one day they came to him with an offer most journey engineers never get.

We are going to give you projects that senior engineers should be doing. If you flourish you will get promoted.

Devin said yes without hesitation. Because he had already been living by a simple rule.

Always work for the position you want to be in. Not the one you are already in. You are already getting paid for where you are. If you only do that job you will stay exactly there.

His first senior level project was a complete wireless re-architecture. Taking a basic setup and building it into a full enterprise environment with a corporate network, a guest network, an executive network and a lab. For the first time he was not just executing tasks. He was thinking like an architect. Looking at how the senior engineers designed things. Understanding that someone has to write the recipe before the chef can cook.

That project was the beginning of a whole new level.

🎙️ Host: Efren Salazar👤 Guest: Devin Prasad | Network Engineer & Cybersecurity Professional🎙️ Show: Wake UP X Podcast

🔗 Full Episode: https://www.wakeupxpodcast.com/the-full-career-story-nobody-tells-you-about-getting-into-itcyber-devin-prasad/

Episode Length: ~30 minutes

In this episode of the Wake UP X Podcast, host Efren Salazar sits down with network engineer and cybersecurity professional Devin Prasad for a conversation about what it truly means to never stop growing.

Devin has watched it happen to too many people in tech. They get skilled. They get comfortable. They develop an ego. And the moment they walk into a room with someone sharper they get intimidated and the growth stops completely.

Devin made a decision a long time ago that he would never be that person.

His mindset has stayed the same since he was 14 years old. There are no ceilings in this game. True wisdom is accepting that you know nothing. And if you can genuinely hold onto that you can keep ascending no matter how experienced you get.

So after years of technical mastery, deep project work and building his reputation Devin looked around and realized he was no longer being challenged. The projects were familiar. The work was repeatable. And without challenge there is no growth.

So he made the move.

🔹 Into consulting.🔹 Into mentoring.🔹 Back into cybersecurity. Full circle.

And then he went on one of the most impressive certification runs you will hear about.

🔹 All three ISC2 certifications earned in less than one year.🔹 Started with the SSCP, Systems Security Certified Practitioner, focused on infrastructure security, firewalls, endpoints and servers. The work he had been doing for over a decade.🔹 But he did not go straight for the top. He used the SSCP strategically as a warmup because he had not sat a formal exam in nearly 10 years and he wanted to walk into the CISSP completely sharp.🔹 The target was always the CISSP, Certified Information Systems Security Professional. One of the most respected and sought after certifications in all of cybersecurity.

That is not just ambition. That is strategy. And that is what separates people who keep ascending from people who plateau.

This episode is for every tech professional who knows deep down they are ready for the next level but has not made the move yet.

🎙️ Host: Efren Salazar👤 Guest: Devin Prasad | Network Engineer & Cybersecurity Professional🎙️ Show: Wake UP X Podcast

🔗 Full Episode: https://www.wakeupxpodcast.com/the-full-career-story-nobody-tells-you-about-getting-into-itcyber-devin-prasad/

Episode Length: ~30 minutes

In this episode of the Wake UP X Podcast, host Efren Salazar sits down with network engineer Devin Prasad for one of the most honest and relatable conversations about breaking into tech.

Devin thought hacking was going to be simple. One path. One button. Easy mode. He even took an ethical hacking course thinking he would be doing advanced cyber operations within a year.

He was humbled fast.

The truth is that hacking is not linear. There is no single method. No cheat code. Hacking simply means using something for a purpose it was never intended for. And once Devin understood that he realized he had a much deeper problem.

He was standing one foot away from a hundred foot canvas. He could only see one tiny corner of the full picture. He needed to back up. Understand how everything connected. Learn the full tapestry of how systems communicate before he could ever think about breaking into them.

That led him to one conclusion. He had to learn networking first.

🔹 He started with Network Plus. It clicked immediately.🔹 His goal was always to get back to cybersecurity but he accepted it was going to take time.🔹 Networking opened doors to understanding databases, servers and cloud in ways a direct path never would have.

But just as things were building the agency he worked at sent all their full time employees to a Cisco CCNA bootcamp. Devin was a contractor. He was not on the list.

And then two agencies that had previously passed on him called back with better paying offers on the table.

More money. A familiar opportunity. An easy way out.

Devin went home and thought about it. And what he decided next is the kind of move that only makes sense when you are playing the long game.

🎙️ Host: Efren Salazar👤 Guest: Devin Prasad | Network Engineer & BGP Expert🎙️ Show: Wake UP X Podcast

🔗 Full Episode: https://www.wakeupxpodcast.com/the-full-career-story-nobody-tells-you-about-getting-into-itcyber-devin-prasad/

Episode Length: ~30 minutes

In this episode of the Wake UP X Podcast, host Efren Salazar sits down with network engineer Devin Prasad to talk about one of the most humbling and pivotal moments in his career journey.

Devin had the skills. He had the passion. He was going home every single night teaching himself. Installing software. Learning the command line. Figuring things out on his own because that is what hunger looks like.

So he started applying for jobs in the public sector. And he walked straight into one of the toughest interview formats in tech.

Back then you did not just sit down and answer questions. You physically took apart a PC and had to identify every component on the spot. CPU. RAM. Power supply. All of it. If you could not do that you never even made it to the second interview where you could actually have a real conversation.

Devin went through three of those interviews. Three times he made it past the hardware portion. Three times he came in second place.

Then one of the interviewers called him back. Not with a job offer. With something better. Real honest feedback.

🔹 Give clear examples.🔹 Add more details to your answers.🔹 Share the results of your work. Not just what you did but what it actually solved and what it meant.

That one phone call changed everything. Most people walk away from rejection feeling bitter. Devin walked away better. And that mindset is exactly what separates the people who eventually break through from the ones who stay stuck.

This episode is for anyone who has ever come in second place and wondered if it was worth keep going. It is.

🎙️ Host: Efren Salazar👤 Guest: Devin Prasad | Network Engineer & BGP Expert🎙️ Show: Wake UP X Podcast

🔗 Full Episode: https://www.wakeupxpodcast.com/the-full-career-story-nobody-tells-you-about-getting-into-itcyber-devin-prasad/

Episode Length: ~28 minutes

In this episode of the Wake UP X Podcast, host Efren Salazar sits down with network engineer Devin Prasad to unpack one of the boldest and most strategic career decisions he ever made.

Devin Prasad had two job offers on the table. One paid more. One had more room to grow. Every single person in his life told him to take the money. His leads. His peers. Not one person was on his side.

But Devin saw the bigger picture.

The higher paying job was at a small office with only 10 to 14 people. Great salary but a hard ceiling. Someone would have to leave before he could move up.

The lower paying job was inside a massive organization with thousands of employees and hundreds of people in his department. More people meant more visibility. More visibility meant more opportunity. More opportunity meant a much higher probability of moving up.

So he took the lower paying job. He showed up hungry. He took on projects. He worked overtime. He built real relationships with customers and teammates. He gave everything he had.

Six months later he got his first promotion to the exact same level the other job was offering from day one.

🔹 The money caught up. It always does when you play the long game.🔹 The relationships he built opened doors money alone never could.🔹 The visibility he gained inside a large organization created momentum that followed him for years.

This episode is for anyone standing at a crossroads between a bigger paycheck and a bigger opportunity. It is a reminder that the best career moves are not always the most obvious ones.

Bet on yourself. Put in the work. Let the results speak.

🎙️ Host: Efren Salazar👤 Guest: Devin Prasad | Network Engineer & BGP Expert🎙️ Show: Wake UP X Podcast

🔗 Full Episode: https://www.wakeupxpodcast.com/the-full-career-story-nobody-tells-you-about-getting-into-itcyber-devin-prasad/

Episode Length: ~28 minutes