This week, we're re-airing our conversation with Reddit CEO Steve Huffman about building one of the internet's most essential platforms over 20 years.

Steve Huffman is the co-founder and CEO of Reddit, one of the internet's most essential platforms with 100 million daily active users and a $20 billion public market valuation. Over 20 years, Steve has guided Reddit through multiple existential challenges, from early acquisition to content moderation crises to competing with AI-generated content.

What you'll learn:

- How Reddit achieved product-market fit in just 2 months and the early signs that indicated massive potential

- Why Steve sold Reddit for $10 million after 18 months and what he learned during his 9-year absence

- The existential crisis that brought him back as CEO in 2015 and how he rebuilt the platform

- Reddit's evolution through three distinct eras: link aggregator, intentionally not social media, and authentic human content in an AI world

- The strategic decision in 2008 to let users create subreddits and how it transformed the platform

- Building content moderation and safety infrastructure from scratch while preserving free speech values

- The challenges and benefits of taking Reddit public while maintaining community ownership

- How Reddit is addressing AI-generated content and the fight for human authenticity online

- The business model evolution from advertising to AI data licensing partnerships

- Steve's vision to make Reddit "universal" and expand from 100 million to billions of users

In this episode, we cover:

(00:00) Introduction and Reddit's 20-year milestone

(02:40) Early product-market fit signals and the $10M acquisition

(06:25) Steve's 9-year absence and return in 2015

(08:30) Content moderation challenges and building safety infrastructure

(14:10) Reddit's three evolutionary eras and strategic positioning

(16:40) The subreddit explosion and community self-organization

(18:08) Positioning as the human platform in an artificial world

(19:15) Human verification challenges and potential solutions

(25:22) AI partnerships, data licensing, and monetization strategy

(29:02) Search evolution and Reddit's role in the new ecosystem

(35:07) Leadership philosophy and staying true to company values

(37:43) The decision to go public and community ownership

(42:18) Managing public company pressures while maintaining long-term vision

(48:27) Steve's vision for Reddit's universal future

Episode 321 - Karl Chandler