In this episode, Sam, Asad, and AJ sit down with Ben Kus, Chief Technology Officer at Box, to unpack how AI is reshaping enterprise tech—from the seismic shift to cloud-native infrastructure to the rise of AI agents that collaborate across platforms. We dive into the realities of leading through volatility, why AI adoption is moving faster than past platform shifts, and how enterprises can navigate the “FOMO” of generative AI without sacrificing trust. Plus, Ben’s take on the future of software engineering, the myth of “non-technical founders,” and the books that keep him thinking ahead.

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Key Moments:

[01:14] – Meet Ben Kus: Box’s AI Visionary

[05:26] – Leading Through Volatility: COVID, ZIRP, and AI’s Sudden Rise

[11:57] – Why AI Adoption Is Moving Faster Than Cloud or Mobile

[17:05] – Data Security in the Age of AI: Box’s Guardrails

[24:17] – AI Agents: The Next Frontier (or Hype)?

[31:41] – Open vs. Walled Gardens: The Future of Enterprise Platforms

[38:45] – Is Software Engineering Still a Valuable Skill?

[46:33] – Stagnation, Patience, and the Long Game