Chris Best of Substack on the Future of Media
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
In this episode, Chris Best, co-founder of Substack, joins a16z partners Katherine Boyle and Andrew Chen to explore how independent media transformed from a scattered blogging ecosystem into a powerful economic engine for creators. Best reveals the cultural significance of Substack's unwavering stance on free speech during the turbulent 2020-2021 period (02:17), when traditional media institutions were firing writers for publishing dissenting voices, while also discussing the evolution from "just blogging with a business model" (07:43) into a comprehensive network that gives creators algorithmic independence and direct audience relationships. The conversation dives deep into Substack's $100 million funding round and ambitious vision to build what Best calls "a new economic engine for culture" (04:03)—reimagining how independent voices can thrive without being downstream from platforms that don't prioritize creator success.
Speakers
Chris Best
Co-founder and CEO of Substack, the independent publishing platform that has revolutionized media economics. Under his leadership, Substack has raised $100M and created a new economic engine for culture, enabling writers to earn millions directly from their audiences while defending free speech during turbulent times.
Katherine Boyle
General Partner at Andreessen Horowitz and board member at The Free Press. Former Washington Post reporter who became an early Substack advocate in 2021, she focuses on the cultural impact of technology and has been a vocal defender of free speech in media.
Andrew Chen
General Partner at Andreessen Horowitz and author of The Cold Start Problem. Former Uber executive who led growth initiatives, he specializes in consumer technology and network effects, bringing deep expertise in building Internet-scale platforms.
Key Takeaways
Build Economic Independence Before Making Waves
Create sustainable revenue streams before taking controversial stands. Chris Best emphasizes that Substack's freedom of speech stance wasn't the primary vision—it was building "a new economic engine for culture" that lets independent voices make money from their work. (04:03) The economic foundation gave writers the security to express authentic viewpoints without fearing financial ruin, proving that financial independence often precedes intellectual courage.
Choose Your Algorithm Master Wisely
Algorithms aren't inherently evil—they're tools that serve whoever programs them. Rather than avoiding algorithmic feeds entirely, professionals should seek platforms where the "secret hidden master" serves their interests, not advertisers. (20:27) The key insight: you want algorithmic assistance that helps you find deeply valuable content rather than content designed purely to capture your attention for ad revenue.
Own Your Distribution, Control Your Destiny
Even the most successful creators remain "downstream" of platforms they don't control. The smartest professionals build direct relationships with their audiences through email lists and owned media, recognizing that social media followers are worthless if algorithms don't surface your content. (15:55) Mark Zuckerberg's whims shouldn't determine your career trajectory—build infrastructure you control.
Embrace Creative Risk Through Subscription Models
Subscriptions give creators the ultimate superpower: the ability to bypass algorithmic gatekeepers and take creative risks. When your audience has explicitly opted to receive your content, you can experiment with ideas that might not please the algorithm but could produce breakthrough work. (09:35) This "trust relationship" allows creators to call in favors and pursue ambitious projects that would never surface in algorithmic feeds.
Compete on Culture, Not Convenience
In a world where AI can generate infinite content, the scarce resource isn't entertainment—it's meaningful culture that helps people become who they want to be. The winning strategy is creating content where people "look back at the time you spend on it and think, damn, I'm glad I did that. That made me a better person." (35:24) Focus on building works that elevate rather than merely occupy attention.
Statistics & Facts
- James Bennett, editor of the op-ed page at the New York Times, was forced to resign for publishing an op-ed by a sitting senator who was still in office during the turbulent 2020 period. (02:01)
- Twitter deplatformed a sitting president and Facebook followed suit during the same period, highlighting the extraordinary censorship environment of 2020. (02:25)
- If you want to be successful and make a successful paid Substack, you have to have a successful Twitter, Facebook, or LinkedIn presence as your top-of-funnel source, demonstrating platform dependency. (15:55)
