From Black Hat to Bug Bounties [Pt. 2] with Thomas DeVoss

From Black Hat to Bug Bounties [Pt. 2] with Thomas DeVoss

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

[09:54] Giving advice to the next generation of hackers

[17:17] Contacting Tommy and keeping up with him on Twitter

[21:43] Planning a Twitch course to teach hackers about bug bounties using real bugs and real-world examples

[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

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Thank you to our sponsors Axonius and PlexTrac for bringing this season of HVR to life!

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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 stereotype of a black hat hacker wanting attention from the media is disproven, Tommy believes that he definitely has craved that media attention for a large majority of his hacking career. Starting in the early 2000s, after 9/11, Tommy had one of his first brushes with fame in an interview with CNN about hacking Middle Eastern companies. Although his hacking and his politics have changed since then, Tommy enjoys having in-depth conversations about hacking and explaining the intricacies of what he does.

“We loved the attention back then, and I still love the attention now, it's nice. The good thing about now is, because I already got in trouble for everything that I've done, I've done my prison time, I don't have anything that I did illegally on the computer anymore that I can't talk about, because I've already paid my debt to society.”

What are the best ways for people to keep up with what you’re doing?

Considering Tommy’s success, it’s understandable that a lot of cyber professionals and amateurs have tons of questions for him. When it comes to getting in contact with Tommy, he recommends tweeting him on Twitter publicly so that he can not only answer your question, but help others with the exact same questions. Education is key, and Tommy is so dedicated to teaching other hackers that he’s currently developing a recurring Twitch stream centered around helping others learn about bug bounty hunting.

“I don't know how successful we're going to be in finding the bugs, but I think it'll be fun to teach people [on Twitch] and do it that way, so that they can actually spend some time learning it. The best way to actually learn this stuff is to actually try and do the hacking.”

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Links:

Stay in touch with Thomas DeVoss on LinkedIn and Twitter.

Check out the Bug Bounty Hunter website.

Keep up with Hacker Valley on our website, LinkedIn, Instagram, and Twitter.

Follow Ron Eddings on Twitter and LinkedIn

Catch up with Chris Cochran on Twitter and LinkedIn

Purchase a HVS t-shirt at our shop

Continue the conversation by joining our Discord

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Learning How to Learn: Mastering the Cyber Fundamentals with Rich Greene

Learning How to Learn: Mastering the Cyber Fundamentals with Rich Greene

The real edge in cybersecurity isn’t found in new tools, it’s built through timeless fundamentals and a mindset that never stops learning. In this episode, Ron sits down with Rich Greene, Senior Solutions Engineer and Instructor at SANS Institute, to uncover how true cyber value starts with skills, curiosity, and mindset. Rich shares his remarkable story of surviving a battlefield injury, retraining his brain, and how that journey shaped his approach to mastering cybersecurity. Together, they connect real-world lessons like the recent Discord breach to the core truth that even advanced systems depend on people who master the basics. Impactful Moments 00:00 - Introduction 02:00 - Discord breach and third-party risk 05:00 - Meet Rich Greene from SANS 06:00 - The power of mastering fundamentals 07:00 - Learning how to learn 08:30 - Rich’s story of rebuilding his memory 11:00 - Forcing the brain to grow stronger 12:00 - Top skills that get you paid 14:00 - Skills that lead to fulfillment 16:00 - Fundamentals that fuel long-term success 17:00 - The OSI model decoded 20:00 - Why operating systems matter 21:00 - Security operations fundamentals 23:00 - Why cloud is the #1 must-learn skill 25:00 - Final advice: sharpen your fundamentals   Links Connect with our Rich on LinkedIn: https://www.linkedin.com/in/secgreene/ Check out our upcoming events: https://www.hackervalley.com/livestreams Join our creative mastermind and stand out as a cybersecurity professional: https://www.patreon.com/hackervalleystudio Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com Continue the conversation by joining our Discord: https://hackervalley.com/discord Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

16 Okt 25min

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10 Okt 21min

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2 Okt 34min

The End of Search and the Rise of AI Browsers and Voices with Ron Eddings

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25 Sep 18min

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18 Sep 33min

The Power of Showing Up: Daily Streams, Big Impact with Gerald Auger

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The Rise of the Autonomous Blue Team with Vineet Edupuganti

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4 Sep 37min

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28 Aug 22min

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