AI Is Already Breaking Into Your Business—Jacob O'Brien Is Building the Defense
Staff Writer • 2025-04-30
Hakware and XGRC Software are using AI to out-hack the hackers, while making compliance less painful for companies that can't afford to get it wrong. When AI Becomes the Threat—and the Shield For years, cybersecurity has been a high-stakes game of cat and mouse. But the mouse just got an upgrade—and it doesn't need sleep. With generative AI giving threat actors the power to spin up malware, phishing scripts, and server-side attacks faster than ever, the defensive line has never been thinner. And that’s exactly where Jacob O’Brien steps in. O'Brien is the founder and CEO of Hakware and XGRC Software, two South African startups at the bleeding edge of cybersecurity and compliance. His companies are proving that the only real way to fight AI-powered attacks… is with AI-powered defenses. On a recent episode of the Stonks Go Moon Podcast, hosted by Rocco Strydom, O’Brien laid out a stark vision of modern cyber warfare—and how his tools are reshaping it. A Cold Machine That Never Misses Traditional penetration tests—those simulated attacks meant to probe a company’s defenses—are manual, slow, and human. That’s the problem, O’Brien says. “You might get someone doing a pen test who’s had a bad day. Hakware doesn’t have moods. It runs every day. It doesn’t miss.” Hakware is an autonomous AI that mimics the behavior of a real hacker. It doesn’t just scan for known vulnerabilities—it adapts. “If the system blocks it one way, it’ll try another. Like a human attacker, but one that never gets tired.” The result is a relentless daily barrage of simulated attacks, constantly testing and refining a company’s security perimeter. Even more concerning, O'Brien demonstrated at Microsoft's Seasons of AI event just how easy it is to use ChatGPT to weaponize the OWASP Top 10—cybersecurity’s most notorious list of vulnerabilities. In less than 15 minutes, he built a bot that could crawl for exploitable infrastructure near any target. It wasn’t theory. It was working code. Compliance That Doesn’t Feel Like Punishment AI isn't just helping O'Brien make companies safer—it's also helping them get compliant faster. His second company, XGRC Software, is a compliance platform that uses AI to guide users through complex standards like ISO 27001 or GDPR. “Most compliance tools are mind-numbingly boring and difficult to use,” O'Brien says. “So we made one that feels more like a living system. You touch something, it reacts. It tells you what you still need to do and why it matters.” The value proposition is clear: if you’re collecting user data, you need to comply with modern data regulations—or face regulatory and reputational hell. But too many startups (and even long-running businesses) skip basic pen tests or ISO audits entirely. “We’ve seen companies that have been around for 30 years and never done one,” O’Brien reveals. “That’s terrifying.” A Founder in the Trenches—and in the Code What sets O’Brien apart in an industry full of suits and sales decks is that he still writes code. “I lead from the trenches,” he says. “I still meet with every partner, and I’m hands-on with every team.” That philosophy helped earn him Most Influential CEO in South Africa in 2024 from CEO Monthly. And it informs his skepticism about the rise of “vibe coding”—the trend of using AI tools to quickly prototype apps without truly understanding the underlying logic. “It’s great for tinkering,” O’Brien admits, “but terrifying for production. If you don’t know what the code does, how do you know it won’t break—or worse, create a security hole you’ll never see coming?” Why AI Makes Cybersecurity More Valuable Than Ever The more AI we embed into our workflows, the more we’ll need companies like Hakware to act as sentries at the gates. In a world where anyone can spin up an exploit with a prompt, the stakes aren’t just higher—they’re constant. O’Brien has seen it all: ransomware built by LLMs, phishing scams with perfect grammar, malicious bots crawling for access points. “The Nigerian prince is gone,” he jokes. “Now he’s using ChatGPT and coming for your production server.” But if he has his way, the defenders are getting smarter too. And unlike the old model, they never sleep.
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