By Chris Foulon & Sinan Eren
Introduction
In this episode of "Breaking into Cybersecurity," we sat down with Sinan Eren, a seasoned cybersecurity professional, entrepreneur, and founder. Sinan’s journey from a curious hobbyist in Istanbul to a serial founder in Silicon Valley offers a wealth of insights for anyone interested in cybersecurity, entrepreneurship, or both. Here are the highlights and lessons from our conversation.
From Hobbyist to Professional: The Early Days
Sinan’s entry into cybersecurity wasn’t a deliberate career choice. In the late 1990s, cybersecurity wasn’t even a defined field—just a function of IT. Resources were scarce, and much of the learning happened in underground communities like IRC and through publications like FRAC magazine. For Sinan, curiosity and a desire to experiment led him to discover vulnerabilities and share his findings on platforms like Bug Track, which eventually opened doors to job opportunities.
Key Takeaway: Sometimes, passion and curiosity can be more important than formal education in breaking into a new field.
Signature-Based vs. Heuristic Security: A Technical Evolution
Sinan explained the shift from signature-based antivirus solutions to heuristic and behavioral approaches. Early security tools relied on known patterns to detect threats, but as malware evolved—like the infamous Code Red worm—this reactive approach proved insufficient. The industry began to focus on detecting abnormal behaviors, setting the stage for modern endpoint security.
Key Takeaway: The cybersecurity landscape is always evolving. Staying ahead means understanding both the history and the latest trends in threat detection.
Entrepreneurship in Cybersecurity: Two Playbooks
Sinan’s entrepreneurial journey followed two main playbooks:
The Hype Playbook: Attach security to the latest technology trend (e.g., AI + Security).
The Next-Gen Playbook: Take an existing solution and make it better, faster, or more secure (e.g., reinventing VPNs with Zero Trust Network Access).
His first company focused on mobile security, capitalizing on the rise of mobile apps and their security flaws. Later ventures addressed remote access and automation, always driven by real-world needs and feedback from users.
Key Takeaway: Successful startups often solve existing problems in new ways or improve on what’s already out there. Listen to the market and adapt.
Lessons Learned: Growth, Pivots, and Exits
Sinan shared candid stories about the challenges of scaling a startup, including the risks of over-reliance on a single partner and the importance of diversifying your customer base. He emphasized the value of learning from mistakes and knowing when to pivot or sell.
Key Takeaway: Flexibility and self-awareness are crucial in entrepreneurship. Sometimes, the best move is to exit and apply your lessons to the next venture.
Automation and the Future: Beyond Cybersecurity
Sinan’s latest venture emerged from listening to managed service providers who struggled with operating and automating a growing stack of security tools. By leveraging process mining, UI automation, and AI, his team built solutions that automate repetitive tasks—not just in cybersecurity, but also in finance and other fields.
Key Takeaway: The skills and solutions developed in cybersecurity can often be applied to other industries. Don’t limit your vision to a single domain.
Advice for Aspiring Professionals and Leaders
For Beginners: The field is more exciting than ever, especially with the rise of AI and LLMs (Large Language Models). Red teaming and offensive security remain fertile ground for creative minds, regardless of background.
For Experienced Pros: Embrace the challenge of integrating AI responsibly. Focus on building guardrails and understanding business processes, not just deploying tools.
For Entrepreneurs: Understand your customers’ workflows and pain points. Document processes, model workflows, and always be ready to adapt your product or business model.
Conclusion
Sinan Eren’s story is a testament to the power of curiosity, adaptability, and listening—both to technology and to people. Whether you’re just starting out or leading a team, the lessons from his journey can help guide your own path in cybersecurity and beyond.
To hear the full conversation, listen to the episode of Breaking Into Cybersecurity (and uploaded as the video in this post ;-) The YouTube channel has years of previous conversations)
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