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Substack Cofounder on AI Slop Content & the Decline of Social Media

What if the future of media isn’t controlled by algorithms or legacy institutions—but by independent voices building directly with their audiences? In this episode, Erik Torenberg is joined by Chris Best, cofounder and CEO of Substack, along with a16z general partners Katherine Boyle and Andrew Chen. We trace the origin story of Substack and its cultural impact, including how it reinvented the business model for independent media. We also explore the evolution of blogging, the rebundling of media, and what the future holds as attention becomes the scarcest resource. Timecodes: 0:00 The Future of Media & Substack’s Role 0:48 The 2020 Media Landscape and Free Speech 3:19 Substack’s Founding Philosophy 6:10 The Evolution of Blogging and Business Models 8:27 Building Direct Connections with Audiences 11:41 The Vision and Growth of Substack 17:57 Algorithms, Networks, and Creator Incentives 22:00 High Value Audiences and Advertising 23:48 AI, Content Creation, and the Value of Attention 29:17 Unbundling, Rebundling, and the New Media Economy 33:01 The Future of Media 38:10 Academia, and Long-Form Writing 43:53 Substack’s Ambitions and Recent Fundraising Resources: Find Chris on Substack: https://cb.substack.com/ Find Chris on X: https://x.com/cjgbest Find Andrew Chen on Substack: https://andrewchen.substack.com/ Find Andrew on X: https://x.com/andrewchen Find Katherine on X: https://x.com/KTmBoyle Find Katherine on Substack: https://boyle.substack.com/ Stay Updated: Let us know what you think: https://ratethispodcast.com/a16z Find a16z on Twitter: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Subscribe on your favorite podcast app: https://a16z.simplecast.com/ Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details, please see a16z.com/disclosures.

Erik TorenberghostChris BestguestKatherine BoyleguestAndrew Chenguest
Sep 2, 202547mWatch on YouTube ↗

CHAPTERS

  1. 0:00 – 1:02

    Why attention—not content—is the real scarce resource

    The conversation opens with a framing question about whether people will read less, quickly shifting to the idea that attention has become the limiting factor. Substack is positioned as a place for “great writing” and culture that’s intrinsically valuable in a world optimized for distraction.

    • Attention is scarcer than content in today’s media environment
    • Great writing and culture have inherent value beyond metrics
    • Substack’s north star is making time spent feel worthwhile and enriching
  2. 1:02 – 3:36

    2020’s media rupture: institutional distrust and Substack’s free-speech moment

    Katherine Boyle revisits the 2020–2021 media landscape—editor resignations, deplatforming, and widespread fear of saying “heretical” things. She argues Substack played an underappreciated role by providing infrastructure for writers to publish independently when institutions and platforms were constricting discourse.

    • 2020 featured high-profile editorial controversies and mass firings
    • Social platforms’ deplatforming created a chilling effect on speech
    • Substack gained cultural significance by protecting writer autonomy
    • The Overton window later shifted (e.g., post-2022 Twitter changes), but Substack’s stance predated it
  3. 3:36 – 6:10

    Substack’s founding philosophy: an economic engine for independent culture

    Chris Best explains that free speech is important but secondary to Substack’s core goal: building an economic model that funds independent voices. The platform is framed as an answer to the internet’s destruction of legacy media business models and the incentive distortions created by ad-driven networks.

    • Substack’s main pillar: independence backed by direct audience support
    • Internet-scale networks brought benefits but warped incentives and culture
    • Editorial freedom plus sustainable income enables healthier media ecosystems
    • Free speech is a necessary precondition for independent cultural work
  4. 6:10 – 8:27

    Saving blogging: from dying ecosystems to paid newsletters as a new model

    Andrew Chen traces the rise and decline of earlier blogging platforms and the lack of sustainable monetization, which led to spam and fragile sites. Substack’s early promise is simplified into a punchline: “blogging with a business model,” enabling more creators to earn without kludgy payment setups.

    • Blogging’s earlier eras (LiveJournal, Blogger, Google Reader) lacked durable economics
    • AdSense/affiliate spam became default monetization and degraded quality
    • Substack streamlined publishing + payments into an easy workflow
    • The ‘blogging with a business model’ critique became a feature, not a bug
  5. 8:27 – 9:49

    Owning the audience: email portability, the “right to exit,” and boomerang creators

    The group digs into why audience ownership matters: Substack lets writers export emails and leave, which forces Substack to earn loyalty through value. Chris argues this “right to exit” creates healthier incentives and even produces “boomerangs” who return after trying other platforms.

    • Email lists create a durable creator-audience relationship beyond platforms
    • Portability is a trust signal and a forcing function for Substack’s product quality
    • Creators can leave—and some return—validating the network’s retained value
    • Subscriptions function as permission to reliably ‘tap the reader on the shoulder’
  6. 9:49 – 15:46

    Direct connection vs algorithms: enabling creative risk and bypassing platform rules

    Chris describes how algorithm-first platforms discourage creative experimentation, even for top creators, because off-format work gets suppressed. Substack’s direct channel lets creators take risks and ask audiences to follow them intentionally rather than appeasing a feed-ranking system.

    • Algorithmic distribution can punish experimentation and narrow creativity
    • Direct connection enables creators to ‘override the algorithm’
    • Trust relationships support non-consensus or novel formats
    • Unsubscribes become a feedback mechanism tied to genuine audience preference
  7. 15:46 – 19:37

    From newsletter tool to full network: why Substack built its own social layer

    Chris explains the strategic evolution: early Substack success still depended on Twitter/Facebook/Google for top-of-funnel growth. To escape being downstream of other platforms’ changing priorities, Substack set out to become a destination network with different ‘laws of physics.’

    • Creators remained vulnerable to external platforms for discovery and traffic
    • Platform shifts (e.g., changing politics policies) can become existential for creators
    • Substack aimed to build a first-class destination aligned with creator success
    • Network-building is difficult and took years, but is core to the long-term plan
  8. 19:37 – 22:00

    Rethinking recommendation: building an algorithm that serves users’ true interests

    Andrew notes the industry’s shift toward “For You” feeds that weaken the follower graph. Chris argues the problem isn’t algorithms per se, but their objective functions; Substack’s goal is recommendation that optimizes for user value and depth rather than ad impressions.

    • ‘For You’ feeds reduce the importance of follower relationships
    • Algorithms are tools; outcomes depend on what they’re optimized to maximize
    • Substack’s aim: objective functions aligned with readers’ deeper preferences
    • Differentiation from ad-driven engagement-maximization models
  9. 22:00 – 24:21

    High-value audiences and the advertising question: aligned sponsorships vs ad incentives

    Erik raises whether Substack will build an ad network, given its sophisticated readership and expansion into video. Chris responds that advertising can be additive if designed from first principles; copying legacy ad models would import misaligned incentives and degrade the platform.

    • Potential upside: sponsorships can expand creator monetization options
    • Risk: traditional ad models can push platforms toward clickbait and misalignment
    • Substack wants an ‘aligned’ version of advertising, not feed-stuffing
    • High-trust niches may support sponsorship models without degrading quality
  10. 24:21 – 29:09

    AI’s fork in the road: slop vs creative leverage and multi-format creation

    The discussion shifts to AI, with Chris describing tools that turn conversations into polished podcasts, videos, clips, transcripts, and translations. Everyone contrasts AI-generated “slop” filling feeds with a more optimistic future where AI increases creative output quality for serious creators.

    • AI can mass-produce low-quality engagement bait (‘AI slop’)
    • AI can also provide creative leverage: repackaging into multiple formats quickly
    • Tools can reduce friction for creators (writer’s block, production overhead)
    • The key is choosing ends/values and applying technology toward them
  11. 29:09 – 33:35

    Unbundling and rebundling media: price discovery and ambitious creator-led companies

    Erik highlights how Substack enables price discovery—writers can capture value directly rather than being underpaid at institutions. Chris draws an analogy to venture capital’s impact on software: freeing builders from hierarchies increases variance and can trigger a cultural renaissance, including new “media founders” who rebundle into larger organizations.

    • Independent publishing reveals true market value of individual writers
    • Analogy: VC unbundled software talent from corporations; Substack can do similar for culture
    • Creator-led models increase experimentation and positive variance
    • Substack aims to support ambitious media founders building beyond a single voice
  12. 33:35 – 38:08

    The ‘two futures of media’: wireheading entertainment vs culture that makes you better

    Chris outlines two diverging futures: hyper-addictive, AI-supercharged entertainment that can erode long-term well-being, and a culture-driven future that helps people become more capable and engaged citizens. Substack’s ambition is to make the second future compelling—so it competes without requiring users to ‘be monks.’

    • Media can function like a drug: pleasurable now but harmful over time
    • AI may intensify addictive entertainment dynamics (‘wireheading’ trajectory)
    • A second future emphasizes culture, meaning, and civic participation
    • Substack’s product goal: time spent should feel enriching and worthwhile
    • History is contingent—technology pushes change, but choices steer outcomes
  13. 38:08 – 45:14

    Beyond media: academia, books, and the long-form ‘intellectual supply chain’

    The conversation expands into adjacent institutions. Chris critiques academic publishing and peer review, entertaining internet-native alternatives for science, while Andrew and Katherine discuss how books and print prestige lag behind where real-time discourse and reading have moved—often powered by long-form writing that later gets remixed into other formats.

    • Academic publishing incentives may be broken; peer review questioned
    • Internet-native publishing could create alternative scientific dissemination
    • Books require high effort and face shrinking distribution economics
    • Medium-based moral panics recur as legacy industries adapt to the internet
    • Long-form writing shapes elite discourse that later spreads through other media
  14. 45:14 – 47:18

    Why raise $100M: scaling Substack’s network into a major destination

    Chris closes by explaining the fundraising rationale: Substack’s core ‘handshake’ is independence plus an internet-scale network. With the network now “alive and growing,” the next phase is to invest in product and organizational scale to compound creator economic value and broader cultural value.

    • Substack’s thesis: combine independent monetization with network discovery
    • The network is described as fledgling but real—ready for a growth phase
    • Capital supports rebuilding the company and product for larger ambition
    • Goal: compound economic upside for creators and cultural upside for users

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