34 min

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

    • Technology

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 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

34 min

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