In this episode, the host interviews Jed, CEO of Grepper and a former Stanford grad school peer, to dive deep into systems thinking, engineering, and how artificial intelligence is transforming software development and operations.
The conversation begins with a lighthearted look back at their time in grad school under advisor Nick McKeown. Jed shares his extensive background, from his early work on SHA-3 in hardware to his time at Nysera, a postdoc at MIT with Nikolai Zeldovich, his stint at AppDynamics before its Cisco acquisition, and his leadership role at Imply. Motivated by observing engineering teams heavily spending on observability as a proxy for reliability, Jed started Grepper to help companies massively reduce telemetry costs and feed those signals into AI-driven troubleshooting systems.
Shifting to the broader impact of AI on software development, Jed notes that while early AI tools were limited to basic autocomplete, they have evolved significantly. For top-tier engineers who understand how to structure complex tasks, AI has drastically accelerated output. Jed describes his personal workflow using Windows Subsystem for Linux (WSL), Claude Code, and models like Opus 5.5, enabling him to ship massive, production-grade projects—such as auto-promotion data lake architectures—in about 10 days instead of the previous six months. However, he emphasizes that the fundamental disparity between good and bad engineers has only widened; bad engineers have not become good ones, but good engineers have become vastly more productive.
The discussion then pivots to the complexities of applying AI to distributed systems and infrastructure operations. While coding is primarily a syntax-driven domain that maps well to a massive training dataset, operations involve heavy-tailed exceptions, unpredictable runtime semantics, and the natural world's messy complexities. Although some skeptics, like the host, view operations as too chaotic and state-space-heavy for AI, Jed is more optimistic. He explains that Grepper approaches operational AI not by lagging backtracking from spiked metrics, but by utilizing predictive models to flag anomalies and newly emerged log patterns. An AI agent can then run through structured workflows, hypotheses, and verification steps to isolate changes and resolve issues.
Despite these advancements, Jed acknowledges that running a large distributed cluster end-to-end via AI is still on the horizon. Code generation enjoys immediate economic adoption because it directly targets engineering productivity, whereas AI-driven SRE and security tooling are still maturing, facing hurdles in value perception and the sheer unpredictability of adversarial or rare production states.
Finally, the two explore the broader trajectory of AI, comparing the digital domain—where the solution space aligns closely with the training distribution—with the real world, where economic equilibrium, system constraints, and simulation limits dictate feasibility. Jed suggests that as AI tools expand, humanity may increasingly shape physical and digital environments to better fit what AI systems require to operate efficiently.