In this episode of the Skin in the Game podcast, we sit down with Stu Sjouwerman, founder and CEO of KnowBe4, to discuss how he built one of the world’s most successful cybersecurity startups from the ground up.
KnowBe4, headquartered in Clearwater, Florida, is a cybersecurity training company focused on mitigating human risk through simulated phishing, user training, and real-time alerts. Today, it generates over $500 million in annual recurring revenue (ARR)—but it started in a 10x10 office, with no external funding.
Stu explains how he identified a massive market gap: most cyberattacks aren’t due to software vulnerabilities—they’re the result of social engineering and human error.
He shares how ransomware attacks in 2013 created a turning point for KnowBe4, propelling the startup into hypergrowth. His strategy? Move fast, market smart, and keep the product simple and sticky.
Stu also dives into:
The future of SaaS in the age of AI
How KnowBe4 is evolving into a platform company
Why AI and quantum computing will trigger “company extinction events”
His belief that LLMs are already a commodity, and the future lies in vertical AI agents
For founders and VCs alike, the episode offers a wealth of insights on startup scaling, product-market fit, and what investors should look for in repeat entrepreneurs.
Whether you're a founder, cybersecurity professional, or angel investor, this conversation with Stu Sjouwerman is a must-listen.
