Tim O’Reilly, Founder & CEO of O’Reilly Media
Today, my guest is Tim O’Reilly, the Founder and CEO of O’Reilly Media, Inc. which delivers online learning, publishes books, runs conferences, and tries to change the world by spreading and amplifying the knowledge of innovators.
In 1998, he organized the meeting where the term “open source software” was agreed on and in 2004, with the Web 2.0 Summit, he defined how “Web 2.0” represented not only the resurgence of the web after the "dot com" bust, but a new model for the computer industry, based on big data, collective intelligence, and the Internet as a platform. In 2009, with his “Gov 2.0 Summit,” he framed a conversation about the modernization of government technology.
His latest book, WTF: What’s the Future and Why It’s Up to Us focuses on implications of AI, the on-demand economy, and other technologies that are transforming the nature of work and the future shape of the business world.
Tim is also a partner at early stage venture firm O’Reilly AlphaTech Ventures (OATV) and on the boards of Maker Media (which was spun out from O’Reilly Media in 2012), Code for America, PeerJ, Civis Analytics, and PopVox.
In this candid conversation, Tim shared the real stories behind his accidental entry into tech writing, his role in defining open source, and his unique philosophy on building healthy platform ecosystems.
1. The Classics of Tech Writing. Tim revealed that despite not being an engineer, he got into the tech world by teaming up with a programmer friend to write a computer manual. He surprisingly found that his academic background in parsing Greek and Latin classics perfectly prepared him to read and translate technical specifications into plain English. By approaching software with a "beginner's mind," he realized that sometimes the most valuable thing to write in a manual was simply confirming for the user that a feature was indeed broken.
2. A Customer-Funded Community. Unlike the typical Silicon Valley path, Tim completely avoided taking venture capital, growing O'Reilly Media starting with just $500 and relying entirely on customer funding and business revenue. Rather than chasing hot trends, he grew his company by simply identifying and serving gaps in the community, whether it was writing the first manuals for undocumented Unix tools, launching the first Perl programming conference, or creating the Safari online learning platform.
3. Defining Open Source and Web 2.0. Although he didn't actually coin the terms "open-source software" or "Web 2.0," Tim played the crucial role in defining what they truly meant and mapping out their impact. He organized the original freeware summit to shift the narrative away from free software being an anti-commerce rebel movement, successfully explaining to the press that free software—like TCP/IP, DNS, and Apache—was actually the critical underlying infrastructure powering the entire internet.
4. The Economics of Ecosystems. Looking toward the future, Tim is highly focused on the concept of platform economics and how algorithms dictate "who gets what and why". He argues strongly against the traditional Silicon Valley "winner takes all" mentality, stressing that massive tech platforms must actively look after their suppliers to survive. He demonstrated this at his own company: when O'Reilly's new live online courses accidentally took too much revenue away from their largest content partner, they deliberately lowered their own course prices to ensure their partner's revenue could catch up, proving that an ecosystem only works if content creators remain financially incentivized.
