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Getting Paid to Break Stuff with Ty Bross, SRT episode artwork

May 26, 2026 23 min

Getting Paid to Break Stuff with Ty Bross, SRT

from WE'RE IN! Hosted by Josh Mason, Ty Bross

On this episode of WE'RE IN, Josh Mason sits down with Ty Bross, Offensive Security Lead for Sidekick Security and Researcher for the Synack Red Team. Ty discusses his teenage hacking origins, how he broke into the cybersecurity profession, his favorite hacks, and advice to aspiring penetration testers. Chapters: 00:00 Introduction 01:50 Understanding Business Logic Vulnerabilities 03:44 Hacker Origin Story 08:18 Joining the Synack Red Team 09:32 Staying Sharp by Hunting for Bugs 11:00 Supplemental Income with The Synack Red Team 11:43 Collaboration with the Synack Red Team 16:37 Chaining Small Exploits Together 17:50 Advice to Aspiring Synack Red Team Researchers 20:54 What Customers Don't Know About Pentesters

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On this episode of WE'RE IN, Josh Mason sits down with Ty Bross, Offensive Security Lead for Sidekick Security and Researcher for the Synack Red Team. Ty discusses his teenage hacking origins, how he broke into the cybersecurity profession, his favorite hacks, and advice to aspiring penetration testers.

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Getting Paid to Break Stuff with Ty Bross, SRT

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This episode was published on May 26, 2026.

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