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, 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

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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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