Portfolio Holding

McCaulley.Org

Portfolio of Companies

Companies

Two distinct ventures under active development and operation — systematic trading and AI-first security.

OR

Options Roamer

Algorithmic Trading · Fintech

AI-driven investment clearinghouse. Real-time signal processing, ML regime detection, and conviction scoring — combined to generate and execute high-quality options trades autonomously. Built for precision at the speed of markets.

TS

Trailhead Security

Cybersecurity · AI Pentesting

AI-first penetration testing platform. Autonomous assessments powered by Cairn — web, cloud, Active Directory, and API attack surface coverage with CISSP-backed reporting. Professional-grade security made accessible.

Principal

Operator and builder. Two companies, one direction.

Brendon McCaulley

Brendon McCaulley

CISSP MBA Fintech Security

Seasoned operator and builder with an MBA and a career spanning financial technology and cybersecurity. Building AI-native companies at the intersection of finance and security — applying institutional-grade rigor to markets and professional-grade security to organizations that can't afford to be wrong.

Founded Options Roamer to bring systematic, ML-driven options trading to a private scale. Founded Trailhead Security to democratize professional penetration testing through AI-augmented autonomous assessments. Both companies share the same operating philosophy: if it's not measured, it doesn't exist.

Active in the North Texas security community. Approach: systematic, data-driven, AI-augmented — across both domains.

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