Hacker Valley Red Hacker Valley Media

This season of Hacker Valley Red wraps up with another interview of an incredible offensive cybersecurity legend. Known first and foremost for his work founding Metasploit and his recent work co-founding Rumble, HD Moore joins the show this week to talk about his journey from spiteful hacker to successful founder. HD walks through the history of Metasploit, the motivation behind their coding decisions, his opinions on open source software, and the excitement of exploration and discovery.
Timecoded Guide:
[04:57] Catching up on HD’s career from his hacking exploits in the ‘90s through his founding of Metasploit to his recent activities with Rumble
[11:41] Getting personal with the feelings and takeaways from a project as successful and impactful on the cyber industry as Metasploit
[18:52] Explaining HD’s personal philosophies around accessible education and the risk of sharing vulnerable information publicly 
[25:39] Diving deep into the technical stories of HD’s path of discovery and exploration during his time at Metasploit
[31:14] Giving advice for future founders and hackers looking to make a legendary impact on the cybersecurity community
 
Sponsor Links:
Thank you to our sponsors Axonius and PlexTrac for bringing this season of HVR to life!
Life is complex. But it’s not about avoiding challenges or fearing failure. Just ask Simone Biles — the greatest gymnast of all time. Want to learn more about how Simone controls complexity? Watch her video at axonius.com/simone
PlexTrac, the Proactive Cybersecurity Management Platform, brings red and blue teams together for better collaboration and communication. Check them out at plextrac.com/hackervalley
 
What were some of the trials, tribulations, and successes of Metasploit? 
Although Metasploit has had a lasting impact on the cyber world, HD Moore is not afraid to admit that part of Metasploit existed out of spite for critics, employers, and gatekeepers in the cybersecurity industry. In terms of trials and tribulations, HD saw a great deal of criticism come from his peers and from professionals ahead of him in the industry, often displaying rudeness towards the quality of the exploits and Metasploit’s audience of young hackers. Later, HD says that a surprising and amusing side effect of his success with the project was watching employers and peers go from criticizing to lifting up his work with Metasploit and attributing success of many hacking professionals to its creation.
“When we started the Metasploit project, we really wanted to open up to everybody. We wanted to make sure that, even if you barely knew how to program, you can still contribute something to Metasploit. So, we did our best to make it really easy for folks to get in touch with us, to submit code.”
 
Where does your philosophy land today on giving information freely?
HD has heard the same opinions many professionals that teach and give information freely have heard: “You’re making it easier for people to use this information the wrong way.” Instead of considering the worst possible outcomes of making hacking accessible, HD chooses to acknowledge the importance of accessible education and publicly provided information. According to HD, if someone is creating and teaching content to the next generation of red teamers, that content is theirs to use. Whether they’re a physical pen tester teaching lock picking or a hacker disclosing a vulnerability, what they choose to share with others has to be based on personal moral code and what others do with that information is up to them. 
“It comes down to: You do the work, you own the result. If you're teaching people how to do stuff, great, they can do what they want. You can decide to do that, you can decide not to do that, but it's your decision to spend your time training people or not training them.”
 
Is it possible to be a CEO, or a co-founder, and stay technical?
The downside of success in the cybersecurity industry is often

We’re joined again by the hacker’s hacker, Tommy DeVoss, aka dawgyg. Bug bounty hunter and reformed black hat, Tommy dives back into a great conversation with us about his journey in hacking and his advice to future red team offensive hackers. We cover everything we couldn’t get to from part 1 of our interview, including his struggles with burnout, his past hacking foreign countries on a bold quest to stop terrorism, and his future in Twitch streaming to teach you how to be a better bug bounty hunter.
 
Timecoded Guide:
[02:57] Fixating on hacking because of the endless possibilities and iterations to learn, but understanding that burnout does happen, especially when hacking gets frustrating
[09:54] Giving advice to the next generation of hackers, including patience for success, getting back up after a failure, and dedicating yourself to a hands-on learning experience
[17:17] Contacting Tommy and keeping up with him on Twitter, and asking questions publicly so that others can learn from the answers he gives you
[21:43] Planning a Twitch course to teach hackers about bug bounties using real bugs and real-world examples of how they work
[24:57] Hacking in the early 2000s and understanding the freedom Tommy has to talk about any and all illegal hacking he’s done now that he’s gone to prison 
 
Sponsor Links:
Thank you to our sponsors Axonius and PlexTrac for bringing this season of HVR to life!
Life is complex. But it’s not about avoiding challenges or fearing failure. Just ask Simone Biles — the greatest gymnast of all time. Want to learn more about how Simone controls complexity? Watch her video at axonius.com/simone
PlexTrac, the Proactive Cybersecurity Management Platform, brings red and blue teams together for better collaboration and communication. Check them out at plextrac.com/hackervalley
 
Do you ever struggle with burnout when it comes to hacking?
Hacking has maintained Tommy’s interest longer than anything else because of the constant changes in technology and the ever-evolving issues in the online world. However, just because hacking is his passion, doesn’t mean that burnout or frustration never happens. Currently, Tommy is taking more of a break with hacking, letting his current day job and his passion for gaming have a front seat. However, he’s still firmly in the industry, passionately developing learning opportunities for future hackers and answering questions from cyber professionals of all backgrounds.
“I do get burned out sometimes…When it comes to bug bounty hunting, I try and make it so it averages out to where I make at least $1,000 an hour for my effort. It doesn't always work. Sometimes I'm more, sometimes I'm less, but I try and get it so it averages out to about that.”
 
What hacking advice would you give the younger version of yourself? 
Although his black hat ways resulted in prison time for Tommy, he doesn’t regret his past and instead seeks to teach others the lessons he’s learned. When we asked Tommy for advice for new hackers, he was clear that success is a longer journey than people assume it is. Tommy’s success was not a fluke, it took years of hands-on learning and patience with failures in order to develop his bug bounty skills. Nothing is actually automatic or easy with hacking, especially as the technology continues to change and evolve. Tommy wants hackers to take every opportunity to try out their skills, even if it's a complete failure.
“Don't expect success overnight. Also, don't let failure discourage you. When it comes to hacking, you're going to fail significantly more than you're going to succeed. And the people that are successful in bug bounties are the ones that don't let those failures discourage them.”
 
What do you think about the “media obsessed” stereotype many people have about black hat hackers?
Wrapping up today, Tommy tells us that he’d be happy to be back in the Hacker Valley Studio again some time. Although the stereot

We’re joined by million-dollar hacker and bug bounty hunter, Thomas DeVoss, this week as we continue our season-long discussion of offensive cybersecurity legends. A legend in the making with a success story in bug bounty hunting that has to be heard to be believed, Tommy is an incredibly successful black hat hacker-turned-bug bounty hunter. He represents how misunderstood the hacking community can be and how positively impactful bug bounties can be. Who hacks the hackers? Look no further than Tommy DeVoss.
 
Timecoded Guide:
[02:59] Becoming interested in hacking for the first time at a young age through internet chat rooms and finding a mentor through those rooms
[08:26] Encountering unfriendly visits with the government and the FBI after his hacking skills progressed and being arrested in the 2000s
[14:20] Seeking his first computer job after a couple visits to prison and finding a new position with someone that knew of his hacking skills 
[25:21] Discussing with Yahoo the possibility of working with them due to his successful bug boundaries and understanding the limitation he would be under if he did that
[30:56] Giving honest advice to hackers looking to break into the bug bounty scene and make the amount of money that he’s making
 
Sponsor Links:
Thank you to our sponsors Axonius and PlexTrac for bringing this season of HVR to life!
Life is complex. But it’s not about avoiding challenges or fearing failure. Just ask Simone Biles — the greatest gymnast of all time. Want to learn more about how Simone controls complexity? Watch her video at axonius.com/simone
PlexTrac, the Proactive Cybersecurity Management Platform, brings red and blue teams together for better collaboration and communication. Check them out at plextrac.com/hackervalley
 
When did you get into hacking for the first time?
At an early age, Thomas found his passion for hacking in an IRC chat room. Mentored by a man named Lewis and encouraged by fellow friends in the hacking world, popping shells and breaking into US systems using foreign IP addresses. Although Tommy became incredible at his craft from a young age, his early habits became serious black hat issues that ended up getting him in trouble with the US government. Just like the hacker in a big Hollywood blockbuster, the government caught up with Tommy and he faced 2 years in prison in his first sentence.
“Instead of coming back to him and saying, "Hey, I'm done," I came back and I was actually asking him questions like, "Can you explain this?” And he saw that I was like, actually interested in this and I wasn't one of the people that was just expecting it to be handed to me and everything like that.” 
 
After spending time in prison, were there barriers to getting involved in hacking again? 
After being in and out of prison a couple times, Tommy found the worst part of coming home to be his ban from touching any sort of device with internet access. Despite it being a part of his probation, his passion for tech continued to bring him back to computers and gaming. After his final stint in prison after being falsely suspected of returning to his black hat ways, the FBI lifted Tommy’s indefinite ban on computer usage and immediately renewed his passion for working in tech. 
“They had banned me indefinitely from touching a computer. So, when I came home on probation the first time, they upheld that and I still wasn't allowed to touch computers as part of my probation. For the first month or so, I didn't get on a computer when I came home from prison, but then it didn't take long before I got bored.”
 
How did your cyber career pivot to bug bounty hunting?
With prison behind him and his ban on computers lifted, Tommy got a job working for a family friend in Richmond, Virginia for a modest salary of $30,000. Although this amount felt like a lot at the time, he quickly realized that there was money to be made in bug bounties. His first few experiments in attempting bug bounty

John Hammond, Senior Security Researcher at Huntress Labs and self-described cybersecurity education enthusiast, joins us as we continue our discussion of red team legends. With a focus on content creation this week, John discusses his success with his YouTube channel, his passion for showcasing authentic and accessible educational materials online, and his advice for creating content safely and spreading awareness with not only a red team or blue team mindset, but with a purple team perspective.
Timecode Guide: 
[01:37] Understanding the impact of content creators in the cybersecurity community, especially when it comes to YouTube educational content
[06:58] Becoming a successful YouTube creator through consistently posting hacking content and ignoring the stereotype of “overnight success”
[13:28] Combining his role as a cybersecurity educator with his security research at Huntress to explore exploits and have real life experience with what he teaches
[16:47] Focusing on the blue side of the house as someone with red team experience, and understanding how to use a tool like PlexTrac to create a collaborative purple team
[21:13] Being mindful of the impact he has through sharing this knowledge and understanding the risk of cybersecurity educational materials falling into “the wrong hands”
Sponsor Links: 
Thank you to our sponsors Axonius and PlexTrac for bringing this season of HVR to life!
Life is complex. But it’s not about avoiding challenges or fearing failure. Just ask Simone Biles — the greatest gymnast of all time. Want to learn more about how Simone controls complexity? Watch her video at axonius.com/simone
PlexTrac, the Proactive Cybersecurity Management Platform, brings red and blue teams together for better collaboration and communication. Check them out at plextrac.com/hackervalley
What is your origin story for wanting to educate other hackers?
Like many of us, John started his journey Googling how to become a hacker. As he gained more knowledge about the specific skills involved in hacking, John never left the internet behind, always seeking out videos and articles explaining new and emerging content. Inspired by those who created that content in the first place, he started his own YouTube channel, simply titled John Hammond, as has spent years cultivating a consistent hacker audience. 
“Along the way, creating content and helping educate others through YouTube is really my main stage platform and has been just a passion project, a labor of love, and something fun along the way.”
 
What feelings do you get looking back on the YouTube content you’ve created so far?
John prioritizes clarity, transparency, and honesty in what he does, and he’s not afraid to show some humbleness, too. Overall, John is thankful for his YouTube success and the impact it had on the cybersecurity community. No matter what he’s showing in his videos, he prefers to keep things honest, to show where he’s made mistakes, and to accept criticism and advice from other hackers and offensive cybersecurity professionals that see his work. 
“I'm showcasing just my computer screen, maybe you get a little face cam and a circle on the bottom right, but it's like you're looking over my shoulder. You're seeing me showcase something raw, live, genuine, and authentic…It’s not all sexy, there’s a lot of failure in hacking.”
 
Have you ever considered focusing on the blue team or the defensive side of cybersecurity?
The majority of John's YouTube content and the work he does in his role at Huntress Labs heavily involves the red team and offensive side of cyber. However, John is a huge advocate for the blue team and the red team collaborating and communicating better. Through making more concepts in cybersecurity accessible through educational content like John’s own videos, he hopes we can continue to bridge the gap and achieve that perfectly mixed purple team.
“We're all playing in concert. As one team sharpens

We’re joined by sponsor and guest Dan DeCloss, CEO and Founder of PlexTrac, on the podcast today to talk about communication and collaboration between the red and blue side of cybersecurity and why security success depends on those two sides working together. On their mission to build stronger, more productive, and well-rounded security teams, PlexTrac provides incredible and insightful metric and messaging tools that change the game for the cybersecurity industry.
Timecoded Guide:
[05:36] Understanding PlexTrac’s history and mission for cybersecurity teams
[09:58] Lack of empathy and understanding in red team and blue team communication
[18:48] Breaking through the resentment and confusion within a team
[24:45] Envisioning the future of PlexTrac’s community impact
[27:52] Caring about your cybersecurity mission beyond yourself
Sponsor:
Thank you to our sponsors Axonius and PlexTrac for bringing this season of HVR to life!Life is complex. But it’s not about avoiding challenges or fearing failure. Just ask Simone Biles — the greatest gymnast of all time. Want to learn more about how Simone controls complexity? Watch her video at axonius.com/simone
PlexTrac, the Proactive Cybersecurity Management Platform, brings red and blue teams together for better collaboration and communication. Check them out at plextrac.com/hackervalley
 
What is the function of PlexTrac that would help you the most as a pen tester?
With prior hands-on experience on the red side, Dan found his journey to creating PlexTrac to be full of moments where he wanted to fix the same problems he encountered over and over with reporting and communicating. One of these problems was solved easily with the addition of a video feature, a simple function that has existed since PlexTrac first began but is instrumental and is a huge time-saver for visual learners.
“As a pen tester, I hated finding that I had 20-odd screenshots if it's a pretty complex exploit. I think the adage for us is like, if a picture's worth 1,000 words, then a video is worth 1,000 pictures, right?”
What do you think are some of the gaps in skills that organizations face when hiring these professionals to perform offensive operations?
Communication is key— not just in life, but in this episode. While we’ve discussed skills gaps previously in cybersecurity, Dan is quick to point out that a consistent gap he sees in all areas of cybersecurity is effective communication. PlexTrac keeps this struggle to communicate in mind and creates easy, simple pathways and functions that encourage communication and facilitate collaborative problem solving.
“If there's one area that I really emphasize with anybody that I'm mentoring or have hired in the past is, as a security person, whether you're red or blue, you really do need to be a good communicator and be able to communicate risk effectively within the right context.”
What would you want to say to those folks that don't see eye-to-eye from the red or the blue side?
We’re fighting the same fight, no matter if we’re on the red side or the blue side of cybersecurity. Dan’s message for our warring red and blue teams throughout the industry is to understand the importance of your mission and to not let relationships between red and blue feel clouded with misunderstanding or resentment. No one’s job is harder than anyone else’s, and each role on offensive and defensive plays a part in our collective victory.
“I'm gonna just be point blank about it…Are you trying to just prove a point about your knowledge and your skills? Or, are you actually trying to make the world a safer place?”
What would you want to say to all those folks out there [in cybersecurity]?
As PlexTrac aims to make a huge impact on our community, Dan and his team acknowledge a need for a unified, focused, and collaborative cybersecurity industry, with hard workers on both the red and blue sides. With PlexTrac’s assistance in making reports, measurable resul

We’re breaking down the concept of difference makers this week and we couldn’t help but call upon Mari Galloway, CEO of the Women’s Society of Cyberjutsu, to be our guest during this conversation. As a black woman in cybersecurity who has dedicated a large portion of her career to helping women and girls become a part of the cyber community on both the technical and non-technical sides, Mari is a stunning example of making a difference and creating a path to expand cybersecurity beyond stereotypes. 
Timecoded Guide: 
- [01:29] Defining the difference makers and explaining the OODA loop
- [13:52] Introducing Mari and the Women’s Society of Cyberjutsu 
- [20:14] Finding her purpose in helping others find their purpose 
- [25:06] Explaining the roles and paths available outside of strictly technical 
- [30:31] Understanding imposter syndrome and forging a freedom-based career journey 
Sponsor: 
Thank you to our sponsors Axonius and PlexTrac for bringing this season of HVR to life! 
Life is complex. But it’s not about avoiding challenges or fearing failure. Just ask Simone Biles — the greatest gymnast of all time. Want to learn more about how Simone controls complexity? Watch her video at axonius.com/simone 
PlexTrac, the Proactive Cybersecurity Management Platform, brings red and blue teams together for better collaboration and communication. Check them out at plextrac.com/hackervalley 
 
What is that like to see people go from taking that original red pill all the way through starting their career in cybersecurity? 
When we talk about making a difference, many of us don’t get to see our impact as clearly as the Women’s Society of Cyberjutsu sometimes gets to see. Mari tells us numerous stories of women throughout this episode, including herself, who became a part of this industry because of the instrumental work they do in outreach and education. For Mari, seeing women change their minds and majors to become a part of the tech industry shows how vital this work is. 
“These are the moments we're waiting for, whether it's one person or 50 million people. We want you to feel confident enough to get the skills you need, get in the industry, continue to refine those skills, and be super successful.” 
 
What would you equate your purpose to, and how does everything you do fit into it?
Like many of us, Mari isn’t entirely sure what her purpose is, but she knows that she enjoys helping the next generation and making a difference in the landscape of cybersecurity. Working with a nonprofit is not an easy job, even if it is rewarding, and Mari still prioritizes her freedom alongside meeting her purpose. No matter what Mari’s future holds, she knows that this work and this purpose to help others will always find her. 
“I think as I get older, as I start to take steps back to just kind of look at what's happened and the impact that I'm having and others around me are having on the next generation of folks coming up, I think my purpose is to help people. It's to help other people see their potential.” 
 
How do you feel like creating that safe environment has affected others? 
Helping others find their footing in the cybersecurity industry can be extremely rewarding, especially when Mari found herself in a situation of uncertainty when she first joined the Cyberjutsu Tribe. The community of cybersecurity and the stereotypes around hackers can feel incredibly uninviting from the outside. Offering people, especially women and young girls, an opportunity to step into a safe space where they can ask anything has been huge for Mari. 
“We call it our Cyberjutsu Tribe, and we want to make sure that anybody that comes to us feels like they can reach out and touch us and ask us questions and get answers and just have a conversation with us.” 
 
How do we invite more people in and let them know that there are opportunities in cyber outside of technical roles? 
Whether you’re hacking, selling,