In this episode, Casey Ellis, founder of Bugcrowd and a pioneer of the crowdsourced cyber security movement, shares the hard-earned lessons from building a category-defining company. Casey pulls back the curtain on the real startup grind: from bootstrapping Bugcrowd into a global force to navigating leadership pressures, health crises and building resilient teams.
He lays bare the hidden truths of entrepreneurship, scaling cyber security innovation, and why humanising hackers is essential to the future of digital defence.
Whether you're a CISO, a cyber founder, or a leader preparing for the next wave of cyber security threats, Casey's insights will resonate deeply and possibly change the way you think about trust, leadership, and resilience.
🛡️ Core Themes and Big Takeaways
Crowdsourcing Cyber Defense: Why tapping global ethical hackers outpaces traditional security models.
Entrepreneurial Resilience: 17+ years to "overnight success" — Casey's brutal honesty on what it really takes.
Leadership Evolution: From "doing everything" to mastering the art of delegation and trust.
Health and Hustle: Ignoring health nearly cost Casey his life and he’s not holding back on lessons learned.
Culture Over Everything: Building trust-first teams that scale cybersecurity innovation.
The Human Side of Hackers: Why reframing the hacker narrative is essential for modern security strategies.
🧠 Soundbites You Can’t Miss
🔥 "You don't get a pass on your health, no matter how 'busy' you are."
🔥 "Building a company is finding where your Venn diagrams overlap, not forcing them."
🔥 "Double down on your strengths. Delegate the rest without guilt."
🔥 "If you're working on your one weakest skill, you're ignoring your ten strongest."
🔥 "Founders should be irrationally passionate about the problem they're solving, it has to look crazy to others at first."
🔥 "Humanising hackers isn't optional. It’s critical if we want cybersecurity to evolve."
🔥 "There’s no such thing as 100% secure, the question is, how do you stay ahead?"
⏱️ Chapters
00:00 - Intro to Casey Ellis and Bugcrowd’s origins
02:08 - How the idea for crowdsourced security was born
06:04 - Entrepreneurial lessons from the GFC, COVID, and everything in between
10:01 - The CEO’s real job: doing less, leading more
14:00 - Ignoring health almost cost everything
18:05 - Timing your scale-up: when, not if
22:05 - How to build and trust a world-class cyber team
28:14 - Why delegation makes or breaks startups
32:45 - Strengths vs Weaknesses: play to your natural edge
34:50 - Capital raising and the "midpoint" you need to find
39:47 - Why culture beats strategy every time
43:39 - Changing perceptions: Hackers as allies
46:35 - The defender’s dilemma — and how to win
51:50 - What's next for cybersecurity in a chaotic world
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