Lenny's PodcastBuilding Substack | Sachin Monga (Substack, Facebook)
CHAPTERS
- 0:00 – 1:07
Why Substack could usher in a “golden era” for writers
Sachin opens with the macro thesis behind Substack: the internet’s ad-driven economics have historically undervalued great writing. He shares how subscription models let creators earn a living (or more) from a smaller, highly engaged audience instead of chasing mass attention.
- •Ad-supported writing has been a weak economic model for most of the internet’s history
- •Early Substack wins came from established writers being “undervalued” elsewhere
- •Recent success stories include people who don’t even identify as writers
- •High-quality work can thrive with a small base that values it enough to pay
- 1:07 – 7:12
Sachin’s path: Facebook → Cocoon → Substack acquisition
Lenny introduces Sachin’s background and the arc that brought him to Substack via the acquisition of his startup, Cocoon. Sachin explains the common thread across his work: building healthier online sharing experiences that aren’t constrained by ad incentives.
- •Sachin joined Substack through the acquisition of Cocoon
- •Cocoon focused on close friends/family photo sharing—different surface, similar motivation
- •At Facebook, ad incentives shaped product constraints and trade-offs
- •Substack’s subscription-first approach felt like the model Cocoon aspired to
- 7:12 – 10:16
Substack’s product org: from no PMs to “full-stack” teams
Sachin describes Substack’s product function evolving from founder-driven coordination to a more structured product org. He details current staffing, team composition, and the core customer-oriented team split.
- •When Sachin joined, Substack had zero PMs and ~15 engineers
- •Now: 4 PMs plus Sachin, and multiple full-stack product teams
- •Teams: Writer, Reader, Growth; plus a Systems/Infra team without a PM
- •Structure is intentionally oriented around customers, not product surfaces
- 10:16 – 14:01
Working with a hands-on, product-strong founder (and scaling the vision)
Sachin explains how to operate effectively as a product leader alongside a highly opinionated founder-CEO. His approach emphasizes facilitation, tight feedback loops, and accelerating shared context so the teams can model the founder’s long-term vision.
- •Early on, Sachin focused on facilitation more than decision-making
- •Problem to solve: founder context no longer fits in one weekly meeting as teams scale
- •Weekly start/end check-ins with CEO to align on priorities and concerns
- •Catching up on years of founder vision helps teams execute coherently amid growth
- 14:01 – 16:37
The hardest part: rapid change and constantly obsolete processes
The conversation turns to startup velocity: any planning or process improvement becomes outdated quickly as headcount and scope change. Sachin argues the real goal is continuous improvement rather than “perfect process,” and notes not everyone thrives in this environment.
- •In high-growth phases, learning ‘the right way’ quickly becomes obsolete
- •Focus should be on getting better week-to-week, not perfecting a static process
- •The job requires comfort with ambiguity and being ‘humbled’ often
- •Rate of change is a major filter for fit in early-stage product leadership
- 16:37 – 20:02
Facebook vs. Substack prioritization: trade-offs vs. sequencing and unlocks
Sachin contrasts prioritization in a massive product like Facebook with a formative startup like Substack. At Facebook, choices can permanently harm other surfaces (true trade-offs), while at Substack time and sequencing dominate—and some bets unlock future capabilities.
- •Facebook PMing involves permanent trade-offs in a constrained UI ‘rectangle’
- •Some decisions at Facebook can make other goals harder ‘forever’
- •At Substack, the main scarcity is time; sequencing matters a lot
- •Substack is evolving from a single-player tool into a broader ecosystem/network
- 20:02 – 22:17
Substack’s principles as strategy: control for writers and readers
Sachin describes how Substack prioritizes from first principles rather than only metrics: maximize creator and consumer agency. The company’s worldview pushes toward designs where writers own the relationship and readers retain control over their experience.
- •Substack starts with a normative view of how the internet should work
- •Writers should control distribution, monetization, and ownership (exportability)
- •Readers should have more agency than in algorithmic feeds
- •Principles help choose between multiple workable implementations
- 22:17 – 27:13
How Recommendations was born: from organic behavior to curated discovery
They unpack the origin story of Substack Recommendations: discovery was already happening through writer-led pathways (guest posts, comments, reader profiles). Instead of algorithmic suggestions, Substack leaned into a writer-curated model aligned with its ‘control’ principle—despite skepticism about adoption complexity.
- •Discovery was already occurring through writer-centric mechanisms
- •The obvious alternative was algorithmic ‘you might like’ recommendations (à la PYMK)
- •Algorithmic insertion risks taking control away from writers/readers
- •Writer-chosen recommendations required opt-in and multiple adoption steps, but worked fast
- 27:13 – 32:52
Impact and next phase: network-driven discovery beyond a single flow
Sachin shares measurable outcomes and where the feature is headed. The team sees recommendations not just as a subscribe-flow step, but as a growing graph of goodwill and influence—opening the door to higher-intent discovery surfaces over time.
- •Recommendations have driven millions of subscriptions across tens of thousands of writers
- •More than 1 in 3 new subscriptions come from the Substack network
- •~1 in 10 paid subscriptions now come via network effects (and growing)
- •Future work: use the recommendation graph beyond the initial subscribe moment for higher-intent matches
- 32:52 – 35:02
Build-with-writers: pilots, feedback loops, and the Product Lab
Sachin explains Substack’s approach to shipping responsibly: involve writers/readers early and often. He describes the pilot mindset behind Recommendations and introduces the invite-only Product Lab used to test and shape features before broad rollout.
- •Operating principle: ‘build with writers, build with readers’
- •Start with mocks, then small pilots rather than big-bang launches
- •Product Lab: ~100 invite-only writers for rapid iteration and feedback
- •Early feedback often changes what ships on day one—or kills features entirely
- 35:02 – 36:37
Dealing with negative press: focusing on signal over noise
Substack often appears in contentious media narratives; Sachin discusses how the product org stays grounded. The key is distinguishing real strategic signal from distractions and maintaining a culture of execution.
- •Most media chatter is distraction; a small portion may be strategic signal
- •Facebook experience helped build resilience to negative press cycles
- •Internal culture emphasizes staying focused and shipping
- •Avoid letting external narratives steer day-to-day product work
- 36:37 – 40:28
Product direction: empowering writers and building a better reader home base
Sachin outlines Substack’s long-term trajectory from two angles: writer tools and reader experience. For writers, it’s about making it easier to start, create across formats, and cultivate community; for readers, it’s about a high-control alternative to addictive feeds, powered by strong apps.
- •Writer side: make it dramatically simpler to start and sustain publishing
- •Substack as ‘home base’ for a creator’s most valuable audience (ownership + export)
- •Expanding beyond newsletters: podcasts, video, and community behaviors (meetups, contributors)
- •Reader side: a controlled, high-quality alternative destination; iOS app launched, Android coming; reader experience will improve rapidly
- 40:28 – 43:17
Advice for writers: start now, lower the stakes, and trust your audience
Sachin and Lenny give practical guidance for creators considering Substack: begin with experimentation, then iterate toward consistency and optionality. They address common anxieties (charging money, frequency, vacations) and argue subscribers are more forgiving—and supportive—than creators expect.
- •Best first step: start publishing and see what resonates (including audio/video)
- •Avoid over-worrying about audience judgment on pricing, cadence, or breaks
- •Subscription is a ‘costly signal’—subscribers grant attention intentionally
- •Lenny’s journey: it’s not too late; 1,000 paid subscribers can be life-changing; expect slow early growth
- 43:17 – 53:00
Sustaining creation: guest posts, community spaces, and careful use of AI
They discuss how Substack can make it easier to keep going without cheapening the experience. Sachin highlights investments in guest posting and community ‘hangout’ spaces, while Lenny raises AI-assisted writing; Sachin notes both the promise and the “can of worms.”
- •Goal: reduce creator burden without undermining quality or control principles
- •Guest posts work well today; Substack is exploring richer contributor workflows
- •Community pilots: a writer-led ‘pub in the back’ for subscribers to chat
- •AI ideas emerge (e.g., assisted writing, generated logos), but require careful consideration
- 53:00 – 1:00:59
Lightning round: books, favorite Substacks, shout-outs, and hiring
The episode closes with rapid-fire questions on influential books and favorite Substacks, plus a shout-out to the team behind Recommendations. Sachin shares where to find him and mentions Substack is hiring for a senior data/product analytics role.
- •Book recommendation: ‘The Timeless Way of Building’ and lessons from architecture/urban planning
- •Substack recs: Martyr Made Podcast, Colin Meloy, House of Strauss
- •Recommendations feature credits: PM Dane Rathbone, designer Gabriel, and broader team
- •Contact + hiring: Sachin on Twitter; Substack seeking senior data/product-growth analytics talent
