How to Build a $3.5B Enterprise (And Survive Every Tech Crash) | Dejan Nenov

6 Oct 2026 · 39 min
39:09

In this episode of the Big Hitters podcast, host Larry Weidel interviews serial entrepreneur and technologist Dejan Nenov. Nenov recounts his journey from a Bulgarian immigrant to a Rose‑Hulman graduate, his early break‑through building a GIS‑driven algorithm that turned a mini‑storage business into a publicly traded REIT, and the series of seven companies he has helped launch across chips, cyber, energy and healthcare, collectively returning about $3.5 billion to investors. He shares core mentorship lessons – never invent technology before finding a problem, and always try to sell before you build – and reflects on surviving the dot‑com crash, the current AI hype cycle, and the importance of disciplined milestones, budgeting, and having liquid cash reserves. Nenov emphasizes the role of a trusted peer network for rapid feedback, the heightened stress of public‑company compliance, and a personal philosophy that success requires continual “micro‑wins,” a relentless adrenaline for winning, and treating technology work as a lifelong hobby. He concludes by describing his current focus: using AI to optimize administrative and clinical processes in American healthcare.

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