In this episode of Bourbon & Bytes, host Terry McGraw sits down with Jason Kaplan, CEO of SixMap, for a spirited conversation that cuts across startup life, cybersecurity mandates, and the rapidly evolving threat landscape.

Kaplan shares his unconventional journey from finance to fitness tech to cybersecurity, offering a founder’s-eye view of how SixMap is redefining External Attack Surface Management (EASM). The two dive deep into the cost-benefit debate around CMMC 2.0, the importance of secure-by-design infrastructure, and why "waiting" is the most expensive strategy of all. They also explore how SixMap uses AI to provide high-fidelity scans of enterprise exposure—mapping vulnerabilities across IPv4/IPv6, ports, and corporate hierarchies.

From ransomware fallout to deepfake dangers, and from bourbon reviews to rapid-fire startup advice, this episode blends strategic insight with real-world urgency.