In this episode of the Cyber Security America Podcast, host Joshua R Nicholson sits down with Chris Freedman, CEO of Ondefend, and Ron Frechette, CEO of CyberSurv, for a deep dive into cybersecurity entrepreneurship.

Both guests share their journeys building companies in the cybersecurity space—from early startup challenges to scaling services, building strong company cultures, and navigating the rapidly evolving role of artificial intelligence in security.

Chris discusses how Ondefend identified an opportunity on the preventative side of cybersecurity, focusing on red teaming, vulnerability discovery, and proactive security testing rather than crowded monitoring and incident response markets.

Ron shares his path from executive search into cybersecurity during the early days of HIPAA compliance and how that experience eventually led him to focus on helping small and mid-sized businesses improve cyber hygiene and resilience.

Together, they explore what it really takes to move a cybersecurity company from zero to one—and eventually from one to scale.

In This Episode

Why cybersecurity remains one of the largest and fastest-growing markets
The realities of launching a bootstrapped cybersecurity startup
How partnerships and subcontracting helped scale early services
Why culture, mission, and hiring the right people matter most
How AI is transforming cybersecurity services and advisory work
The growing demand for fractional CIO and fractional CISO leadership
Lessons learned from scaling consulting and cybersecurity service firms

Key Takeaways

The hardest stage of building a company is going from zero to your first customers.
Strong partnerships can accelerate growth when building credibility in cybersecurity.
AI is rapidly changing how cybersecurity assessments and advisory services are delivered.
Many organizations are shifting toward fractional cybersecurity leadership models to gain specialized expertise without full-time executive hires.

Featured Guests

Chris Freedman CEO of Ondefend Entrepreneur and cybersecurity innovator focused on proactive defense, red teaming, and security testing technologies.

Ron Frechette CEO of CyberSurv Serial entrepreneur helping organizations improve cyber hygiene through AI-driven cybersecurity advisory services.

🎧 Listen now on Spotify, Apple Podcasts, or your favorite podcast platform.

#Cybersecurity #InfoSec #CyberThreats #CyberDefense #RedTeam #PenTesting #IncidentResponse #CyberHygiene #DataSecurity #MDR (Managed Detection & Response). Thanks to our show sponsor Darkstack7 Cyber Defense services www.darkstack7.com.