#183 Jacob O'Brien | Cyber Guardians and the Business of Staying Safe Online episode artwork

EPISODE · Apr 30, 2025 · 18 MIN

#183 Jacob O'Brien | Cyber Guardians and the Business of Staying Safe Online

from Stonks Go Moon · host Rocco Strydom

In this episode of The Stonks Go Moon Podcast, host Rocco Strydom sits down with Jacob O'Brien, Founder and CEO of Hackware and XGRC Software—two companies at the bleeding edge of AI-powered cybersecurity and compliance automation.They dive into:Why most cybersecurity software is broken (and boring)What an AI-driven penetration test actually looks likeWhat companies get wrong about compliance and ISOHow AI is being weaponized by cybercriminals—and what you can do about itWhy Jacob still codes alongside his engineers (and what “vibe coding” gets dangerously wrong)Plus: the shocking demo he gave at Microsoft’s Seasons of AI event, where a GPT-powered script was used to weaponize the OWASP Top 10 vulnerabilities in real-time.Whether you're a startup founder, enterprise CTO, or just want to sleep better at night knowing your data is secure—this episode is a must-listen.🔗 Learn more: https://hakware.com/Subscribe for more high-signal convos with the builders and founders shaping the future

In this episode of The Stonks Go Moon Podcast, host Rocco Strydom sits down with Jacob O'Brien, Founder and CEO of Hackware and XGRC Software—two companies at the bleeding edge of AI-powered cybersecurity and compliance automation.They dive into:Why most cybersecurity software is broken (and boring)What an AI-driven penetration test actually looks likeWhat companies get wrong about compliance and ISOHow AI is being weaponized by cybercriminals—and what you can do about itWhy Jacob still codes alongside his engineers (and what “vibe coding” gets dangerously wrong)Plus: the shocking demo he gave at Microsoft’s Seasons of AI event, where a GPT-powered script was used to weaponize the OWASP Top 10 vulnerabilities in real-time.Whether you're a startup founder, enterprise CTO, or just want to sleep better at night knowing your data is secure—this episode is a must-listen.🔗 Learn more: https://hakware.com/Subscribe for more high-signal convos with the builders and founders shaping the future

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#183 Jacob O'Brien | Cyber Guardians and the Business of Staying Safe Online

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This episode was published on April 30, 2025.

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In this episode of The Stonks Go Moon Podcast, host Rocco Strydom sits down with Jacob O'Brien, Founder and CEO of Hackware and XGRC Software—two companies at the bleeding edge of AI-powered cybersecurity and compliance automation.They dive into:Why...

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