From Black Hat to Bug Bounties [Pt. 1] with Tommy DeVoss

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 blach hat hacker-turned-bug bounty hunter, representing 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  [08:26] Encountering unfriendly visits with the government and the FBI after his hacking skills progressed  [14:20] Seeking his first computer job after prison and leveraging his hacking skills [25:21] Discussing with Yahoo the possibility of working with them due to his successful bug boundaries [30:56] Giving honest advice to hackers looking to break into the bug bounty scene  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 is pleased to offer an exclusive Red Team Content Bundle for Hacker Valley listeners. This bundle contains both our "Writing a Killer Penetration Test Report" and "Effective Purple Teaming" white papers in ONE awesome package. Head to PlexTrac.com/HackerValley to learn more about the platform and get your copy today! 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 programs had him earning $20,000 or $30,000 for hours of work, a huge increase from the salary he was currently making. Encountering success after success