In this episode of Inside the Network, we sit down with Dug Song, the legendary co-founder and former CEO of Duo Security. Dug's journey is nothing short of iconic—he turned a side project into a cybersecurity powerhouse with over 50,000 customers and a $2.35 billion exit to Cisco. In a world obsessed with unicorn status and funding hype, Dug stands out as a founder who stayed grounded in values, culture, and customer empathy.

We explore Dug’s early years—from doing data entry in his father’s liquor store in West Baltimore to cutting his teeth at Arbor Networks, leaving security, and coming back to change how security is delivered. Dug was also part of the hacker collective w00w00, alongside future tech luminaries like Jan Koum (WhatsApp) and Shawn Fanning (Napster), where he honed the ethos of solving hard problems and building in community. These experiences laid the foundation for Duo, which Dug and co-founder Jon Oberheide started not with a grand business plan but a desire to democratize security and make strong authentication simple and usable for all organizations—not just the Fortune 500.

This conversation is packed with actionable lessons for founders: how to build a billion-dollar business with capital efficiency and discipline; how to prioritize user experience in security, not just infrastructure; and how to lead with integrity and build a “learning organization” that continuously improves across every function—engineering, sales, marketing, and customer success. Dug also gives an inside look at the decision to sell Duo to Cisco versus going public and what that choice meant for the company, team, and customers.

We then dive into Dug’s post-Duo chapter, where he and his wife Linh are reshaping philanthropy and backing the next generation of founders in Michigan, Detroit, and beyond. From punk rock to planetary-scale startups, Dug brings a rare mix of grit, humility, and wisdom, making this episode a must-listen for any entrepreneur.

158. Why Did Rome Fall — and Are We Next?

People I (Mostly) Admire

Intro

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