Episode #7 gets deep into building, transforming, and growing software-centric businesses. Dan Van Tran is the CTO of Collectors, a technology company that helps people authenticate, grade, vault, and sell collectibles.

Dan is a technology executive, engineering leader, and CTO advisor who has spent his career building and evolving complex software organizations and production systems.

At Collectors, Dan has led engineering through a period of significant growth and modernization, balancing the realities of legacy technology with the need to move quickly, improve reliability, and build for the future. He also advises CTOs and technology leaders on architecture, organizational design, engineering effectiveness, and navigating large-scale change.

I’ve had the good fortune to work with Dan twice as a customer and I’ve always appreciated his combination of deep technical judgment, pragmatism, curiosity, and willingness to get into the deep details of how software systems—and the teams behind them—actually work.

This is an episode packed full of pragmatic wisdom for the realities of building and operating software systems here in late 2026. Yet, even if you're not a technologist, you'll enjoy Dan's stories of his family's migration from Vietnam, his approach to leadership, and how he finds resilience in the face of AI-fueled change.