July 1, 2025

Podcast

So, You Think You Can Dev?

Pillars Discussed

Binary Troubleshooting

Concierge Support for Edge Cases

Empathetic Communication

Relationship-Building as Risk Reduction

Introduction:

I had a great time discussing my unique approach to technology leadership, sharing insights from my 15+ years of experience across entertainment, sports (LA Clippers), and venture capital. The conversation centered on navigating AI disruption while maintaining humanity at the center of technological transformation. I emphasized my role as a "bridge-builder" between technical and business stakeholders, introducing my "Hurricane Method" for managing complex technology implementations.

Key Topics I Covered:

Unprecedented Nature of AI Disruption

I explained how current AI adoption differs from previous technology cycles. Unlike traditional top-down or bottom-up implementations, AI is being adopted simultaneously across all organizational levels - from interns to executives - with each finding unique use cases. I noted that non-technical C-suite executives are buying into AI more fervently than ever before, despite not fully understanding implementation.

Winning Strategies in AI for Tech Leaders

I differentiated between sustainable AI businesses and "micro-SaaS" point solutions. Successful companies focus on solving complex, interconnected problems rather than just adding AI features. I emphasized the importance of agility and the mindset that current solutions might become irrelevant in six months, requiring continuous evolution and adaptation.

Empathetic Innovation and the Human Element

I stressed the critical importance of involving people who might be displaced by AI in the implementation process. I advocated for "empathetic innovation" - focusing on eliminating tasks people hate doing rather than replacing what they enjoy. This approach builds trust and ensures better adoption while treating technological change as a human experience, not just a technical one.

Bridging Technical and Business Divides

I addressed the fundamental communication gap between technical and business teams, comparing it to a doctor-patient relationship. I emphasized the need for technical leaders to develop "bedside manner" and translation skills, helping both sides understand each other's languages and building trust for successful innovation.

Conclusion:

I presented technology leadership as fundamentally about human connection and empathetic communication rather than just technical expertise. My "Hurricane Method" represents a holistic approach to managing technological change that combines technical precision with human understanding. The key takeaway is that successful technology implementation requires curiosity, trust-building across organizational divides, and treating people as partners in transformation rather than obstacles to overcome. In the age of AI disruption, leaders who can bridge technical and human elements will be most successful in driving meaningful organizational change.