undefined - Founder Mode: Chris Best, Founder & CEO, Substack

Founder Mode: Chris Best, Founder & CEO, Substack

In this episode, taped in front of a live audience, Chris Best tells us the story of Substack. He reminisces about his adventures with Elon Musk, and explains how he persisted in bringing to market a component of Substack that he knew was critical to their vision, even though any non-founder CEO would have killed it after years without any growth.

September 4, 202527:53

Table of Contents

0:00-8:01
8:03-15:18
15:19-23:43
23:43-27:50

🎙️ What Makes Substack Different from Other Publishing Platforms?

The Platform Revolutionizing Independent Media

The Definition Challenge:

  • Media Network & Publishing Platform - Built specifically for independent creators to monetize their work
  • Discovery Destination - Increasingly becoming the place to find "all the smartest and best independent voices in the world"
  • Simple Yet Powerful - Started as a tool to make paid email newsletters dead easy

Why Chris Struggled to Answer:

When Jessica asked Chris to explain Substack, he literally said "Oh god, this is my this is the one question so hard to answer" - showing how even founders struggle to simply define their evolving platforms.

The Reading Philosophy:

Chris's Core Belief: What you read isn't just time spent - it's your training data that:

  • Shapes how you think
  • Changes how you see the world
  • Determines who you become

This philosophy became the foundation for everything Substack would build.

Timestamp: [0:00-1:50]Youtube Icon

💡 How Did Substack Transform from a Failed Essay into a Billion-Dollar Company?

From Failed Essay to Billion Dollar Company

The Sabbatical Phase:

After leaving his first startup, Chris was:

  • Taking time off to see friends and family
  • Reading books
  • Learning to fly airplanes
  • Doing "all the things you don't have time to do if you're running a startup"

The Writing Attempt:

Chris's Thought Process: "I should write. How hard could it be? I know how to type. I have thoughts that I'm very impressed with."

What He Wrote: A screed about how:

  • The internet smashed all business models for culture
  • Massive internet-scale networks replaced traditional media
  • These platforms are phenomenal businesses but "they're driving us fucking crazy"

The Reality Check:

Hamish's Gentle Feedback:

  • "It's 2017, Chris"
  • "Your thesis is maybe newspapers are in trouble and maybe Facebook is not an unalloyed good"
  • "This is known. This is not going to come as a shock to anyone"

The Pivotal Suggestion:

"So what do you do about it?" - The question that transformed a mediocre essay into a company

Timestamp: [1:51-3:40]Youtube Icon

📝 Why Did Substack's Founders Choose a Manifesto Over an MVP?

The Unconventional First Step

What They Actually Did:

  1. Hamish - Started writing the manifesto
  2. Chris - Built blogging software to host it
  3. The Principle - "We're not going to post our founding manifesto on somebody else's software. That would be ridiculous."

Chris's Disclaimer:

"This is our story of what we did, not what I would necessarily recommend that anybody do"

The Two-Layer Vision:

The Grandiose Layer:

  • A new economic engine for culture
  • Creating better incentive structures
  • Producing superior emergent outcomes for media
  • All the "blah blah blah blah blah" (Chris's actual words)

The Practical Layer:

  • Service that makes it dead easy to create paid email newsletters
  • The smallest possible instantiation of the grand scheme
  • Focus on creators wanting subscribers to "fall in love with their work"

The Grace They Had:

They called it a manifesto among themselves but had "the grace not to put manifesto in the title"

Timestamp: [3:41-6:07]Youtube Icon

💰 How Did Substack's First Customer Generate $100,000 in One Day?

The $100,000 First Day Story

The First Real User:

  • Name: Bill Bishop
  • Newsletter: Sinocism ("a terrible pun" according to Chris)
  • Topic: China analysis for international business and government audiences
  • Status: Already widely respected, wanting to go paid

How It Happened:

Someone from Hamish's journalism network read their manifesto and said:

  • "Hey, I think I need this"
  • "I've been wanting to go paid like Ben Thompson does"
  • "But I can't be bothered to figure out how to connect all the pieces"

The Launch Results:

Day One: Bill made approximately $100,000

Chris's Real-Time Reaction:

  • Watching his "hacked together Stripe wrapper" process payments
  • Thinking: "Is this good? I think this might be good"

The YC Interview Moment:

Before Launch: Application showed "$0 in revenue"

At Interview:

  • YC: "It says here you make zero dollars"
  • Chris: "Ah, I have an update on that"
  • Jared's Response: "If you just get like two or three more like that, you're going to be golden"

Timestamp: [6:08-8:01]Youtube Icon

💎 Summary from [0:00-8:01]

Essential Insights:

  1. Media as Training Data - Chris believes what you read fundamentally shapes who you become, not just how you spend time
  2. Criticism Into Creation - When pointing out problems (broken media economy), always ask "so what do you do about it?"
  3. Start Simple, Dream Big - Launch with the smallest viable version (paid newsletters) while maintaining the grand vision

Actionable Takeaways:

  • One Customer Can Change Everything - Bill Bishop's $100k first day proved the concept better than any pitch deck
  • Leverage Your Network - Hamish's journalism connections provided the first critical user
  • Perfect Timing Beats Perfect Product - A "hacked together Stripe wrapper" at the right moment beats elaborate features

The Partnership Dynamic:

  • Complementary Skills - Technical founder (Chris) + experienced writer (Hamish)
  • Honest Feedback - A co-founder who can say "your idea isn't as brilliant as you think"
  • Shared Frustration - Both wanted to fix the broken media incentive structure

The YC Lesson:

Going from $0 to $100k between application and interview - sometimes the best pitch is showing real traction.

Timestamp: [0:00-8:01]Youtube Icon

📚 References from [0:00-8:01]

People Mentioned:

  • Hamish McKenzie - Chris's co-founder, former journalist at Pando Daily, lead writer at Tesla, published author
  • Bill Bishop - First Substack customer, creator of Sinocism newsletter about China
  • Ben Thompson - Referenced as successful paid newsletter model that inspired early Substack users
  • Jared Friedman (Y Combinator) - Partner who provided encouragement during YC interview

Companies & Organizations:

  • Y Combinator - Accelerator program Substack joined in Winter 2018
  • Tesla - Where Hamish worked as lead writer before Substack
  • Pando Daily - Publication where Hamish previously worked as journalist
  • Stripe - Payment processor Chris used for initial platform
  • Facebook - Referenced as platform that's "not an unalloyed good"

Publications & Newsletters:

  • Sinocism - Bill Bishop's China-focused newsletter, Substack's first customer
  • The Substack Manifesto - Founding document outlining vision for new media economy

Concepts & Frameworks:

  • Economic Engine for Culture - Substack's vision for creating sustainable creator economy
  • Media as Training Data - Chris's philosophy that reading shapes who you become
  • Incentive Structure Design - Focus on subscriber love over attention-grabbing

Timestamp: [0:00-8:01]Youtube Icon

🎰 Why Did Substack's First Customer Success Create False Expectations?

The Reality Check After the $100K Launch

The Perfect Storm Customer:

  • Bill Bishop's Unique Position - One of only "five people on Earth" who were perfect early customers
  • Years of Built-Up Demand - Had users wanting to pay him for years
  • Simple Monetization - Just sent an email saying "this costs money now" and subscribers immediately paid

The Gambling Analogy:

Chris's self-aware observation about their journey:

  • "Professional gamblers often start their career with a winning streak"
  • Selection Bias Reality - Those who start with losing streaks don't become professional gamblers
  • Substack's Pattern - Early win created false confidence: "Oh, this is going to be so easy"

The Years-Long Reality:

  • Biggest Customer for Years - Bill Bishop remained their largest customer for multiple years
  • No Similar Success - "We did not taste success like that again for many years"
  • The Silver Lining - That initial push gave them courage to persist through difficult times

Timestamp: [8:03-9:24]Youtube Icon

🚀 What Critical Advice Did Y Combinator Give Substack During Their Program?

The Launch Lesson That Changed Everything

The Weekly Jared Question:

Every single week during YC, the same exchange:

  • Jared: "Have you launched it yet?"
  • Chris & Team: "Well, no, we have good reasons..."

The Embarrassing Technical State:

Manual Everything:

  • If someone wanted to create a new Substack, Chris had to manually input it into the database
  • Chris's response: "Yeah, talk to me and I'll launch for you"
  • The excuse cycle continued week after week

The Turning Point:

Jared's Approach:

  1. Started gentle - letting them explain their "good reasons"
  2. Escalated to shaming - "You guys are being complete idiots here"
  3. Final push - "Launch your goddamn service"

The Critical Realization:

  • Chris's Admission: "He did the gentle thing where he causes you to realize yourself how much of an idiot you're being"
  • The Stakes: "If we hadn't launched it, it wouldn't have worked. I'll tell you that much"
  • The Result: They launched during the three-month program

Timestamp: [9:25-10:24]Youtube Icon

📈 How Did Substack Perform at Demo Day and What Happened Next?

From Middle-of-the-Pack to Series A

Demo Day Reality Check:

  • Self-Assessment: "Somewhere in like the third quartile. Maybe we're the median company"
  • Not a Hot Company - Had believers but weren't one of the standout successes
  • Competitive Batch - Other companies from Winter '18 are "still crushing it"

The Manual Growth Hack:

Group Subscription Hustle:

  • No group subscription feature existed
  • One customer was selling lots of group subscriptions
  • Solution: Manually sold subscriptions to bankruptcy firms to boost Demo Day numbers

The Unexpected Series A:

The Andrew Chen Story:

  1. Recruitment Attempt - Tried to get Andrew Chen (ex-Uber, great blogger) to write on Substack
  2. The Plot Twist - He joined Andreessen Horowitz instead
  3. The Call - "I'm not bringing my blog over, but do you want to come talk to us?"
  4. Initial Response - "No, leave us alone. We're busy. We don't talk to investors"
  5. The Persistence - "Come have dinner with Marc"
  6. The Result - Got preempted into their Series A unexpectedly

Timestamp: [10:25-12:14]Youtube Icon

🎯 What Does Founder Mode Mean for Building a Platform Like Substack?

The Long-Term Vision That Only Founders Can Sustain

Chris's Definition of Founder Mode:

Core Capability: "Have a long-term principled vision for why we're making the thing we're doing"

Key elements:

  • Understanding the actual center of the idea
  • Knowing why it ought to win
  • Being "very long-term greedy" about that vision
  • Taking seriously the consequences of what that theory actually means

The Grandiose Vision (Since Day One):

  • The Mission: Building a new economic engine for culture
  • The Goal: Create a platform that could "spark a renaissance"
  • The Philosophy: Writers and creators are the heroes, not Substack
  • The System: A better social contract that pulls people in through superior incentives

Why This Matters:

Unlike Many Startups:

  • Not everyone operates this way - many pivot and discover
  • Substack started with manifesto and grandiose idea
  • Every stage had different product positioning, but core vision remained constant

The Practical Application:

At every stage, they needed:

  1. Product people could understand (the handle)
  2. System that actually works and competes
  3. Platform people willingly adopt because it's great

Timestamp: [12:15-14:29]Youtube Icon

🔍 What Was Substack's Biggest Discovery Problem and Why Did It Matter?

The Fundamental Flaw in the Beautiful City

The Missing Piece:

What Worked:

  • Host a blog ✓
  • Run an email newsletter ✓
  • Charge subscriptions ✓
  • People could fall in love and pay ✓

The Critical Question: "But where did they find you?"

The Uncomfortable Answer:

Readers found writers on:

  • Twitter
  • Facebook
  • LinkedIn
  • "Increasingly now all these places"

The Toxic Dependency Problem:

Two Major Issues:

  1. Downstream Pollution:
  • Substack's "beautiful city" was downstream of the "toxic sludge incentive factory"
  • To be great on Substack, you first had to be good at Twitter
  • Success required mastering other platforms' attention-grabbing tactics
  1. Misaligned Incentives:
  • Other platforms optimized for engagement and outrage
  • Substack wanted quality and subscriber love
  • Writers had to play by different rules on different platforms

This discovery problem would eventually lead to Substack's controversial decision to build their own social features - setting up the coming Elon Musk drama.

Timestamp: [14:30-15:18]Youtube Icon

💎 Summary from [8:03-15:18]

Essential Insights:

  1. Early Success Can Be Dangerous - Their first customer's $100K day created false expectations that took years to replicate
  2. Launch Before You're Ready - Jared's persistent "Have you launched yet?" saved them from perfectionism paralysis
  3. Founder Mode is Long-Term Vision - The ability to maintain a principled, grandiose vision through years of grinding that a hired CEO wouldn't sustain

Actionable Takeaways:

  • Manual Before Automated - They sold group subscriptions manually to bankruptcy firms before building the feature
  • Recruitment Can Lead to Investment - Failed attempt to recruit Andrew Chen led to unexpected Series A
  • Discovery is Everything - A perfect product means nothing if users can't find creators without relying on toxic platforms

The Platform Paradox:

  • The Beautiful City Problem - Building something better while dependent on worse systems for growth
  • Incentive Misalignment - Creators had to master attention-grabbing on social media to succeed with quality on Substack
  • The Coming Solution - This discovery problem would drive their controversial social features decision

Key Growth Phases:

  1. YC Period - Learning to launch imperfectly
  2. Post-Demo Day - Manual hustling for growth
  3. Series A - Unexpected preemption from failed recruiting
  4. Discovery Challenge - Recognizing the fundamental platform dependency issue

Timestamp: [8:03-15:18]Youtube Icon

📚 References from [8:03-15:18]

People Mentioned:

Companies & Organizations:

  • Y Combinator - Accelerator program, Winter 2018 batch
  • Andreessen Horowitz - VC firm that preempted Substack's Series A
  • Uber - Where Andrew Chen worked before joining a16z
  • Twitter - Platform where Substack writers had to build audience
  • Facebook - Another discovery platform creating dependency issues
  • LinkedIn - Additional platform for writer discovery

Concepts & Frameworks:

  • Founder Mode - Ability to maintain long-term principled vision that hired managers wouldn't sustain
  • Selection Bias in Success - Professional gamblers start with winning streaks
  • The Discovery Problem - Fundamental challenge of platform dependency
  • Long-term Greedy - Chris's term for maintaining vision despite short-term challenges
  • Economic Engine for Culture - Substack's core mission to spark a renaissance

Timestamp: [8:03-15:18]Youtube Icon

🚨 Why Did Substack Need to Build Its Own Social Network Despite the Risks?

The Platform Dependency Crisis

The Fundamental Problem:

Two Critical Vulnerabilities:

  1. Algorithm Dependency
  • Mark Zuckerberg declares "no more politics for a while"
  • Political writers on Substack who got traffic from Facebook suddenly lose their audience
  • Writers' livelihoods dependent on platform mood swings
  1. Acquisition Threats
  • Platform owners could try to buy or destroy competitors
  • As Chris notes: "If Elon buys Twitter and decides maybe I want to buy Substack and maybe if I can't I'm going to kill those guys"

The Founder Mode Decision:

Why Only a Founder Would Do This:

  • Not Short-Term Optimal - Wouldn't maximize next couple years' value
  • Hard to Believe In - Many people thought it was a bad idea
  • PG's Skepticism - Paul Graham "might still think it was a bad idea" and told Chris multiple times
  • Long-Term Essential - Without it, Substack couldn't become "the real thing"

What They Built:

  • Mobile app (obviously very hard to do)
  • Short-form feed (Twitter-like functionality)
  • Discovery features within Substack
  • Fun, engaging experience that doesn't require being "a monk to use Substack"

Timestamp: [15:19-17:13]Youtube Icon

🤝 What Happened When Elon Musk Tried to Buy Substack?

The Midnight Meeting That Changed Everything

The Setup:

  • Context: Elon had bought Twitter and was "getting sick of running it"
  • Shared Values: Both believed in free speech and freedom of the press
  • The Call: "Hey, you want to come meet?"
  • The Meeting: Old Twitter HQ at midnight ("very dramatic hour")

The Offer:

Elon's Proposition:

  • Buy Substack
  • Have Chris come run Twitter
  • "Join forces" and "that'll be cool"

Chris's Response:

  • "Okay, let me think about it"
  • No numbers discussed, just conceptual

The Timing Disaster:

  • Meeting happened days before Substack's planned launch
  • They were about to launch "a thing that looks a lot like a Twitter competitor"
  • Had been planning this for a while as part of long-term strategy

The Heads-Up:

Chris informed Elon before launch:

  • "We're launching this thing"
  • "We've been planning it for a while"
  • "We're not trying to be a competitor"
  • "We're very aligned in principles"

Elon's Response: "Don't launch it"

Chris's Decision: "I'm not going to not launch it"

Timestamp: [17:14-19:23]Youtube Icon

😤 How Did Elon Musk Retaliate Against Substack on Twitter?

The Week Substack Became Voldemort

The Digital Warfare:

Immediate Retaliation Tactics:

  1. Word Ban - "Substack" became unsayable on Twitter
  • Tweets containing "Substack" wouldn't be seen by anyone
  • Users called it "The platform that cannot be named"
  1. Search Blocking - Couldn't search for "Substack" on Twitter

  2. Link Punishment - The 5-second delay treatment

  • Only Substack and New York Times got this
  • Links would redirect but take 5 seconds
  • Chris: "5 seconds is an eternity"

The Personal Attacks:

  • Mean texts from Elon
  • Very angry response
  • Took the launch as a definitive "no" to acquisition

Chris's Fear:

The Tesla Concern:

  • "I drive a Tesla. I had moments where I was like, will he kill me?"
  • Audience laughs, but Chris notes: "That's a weird feeling"
  • Still drives the Tesla: "I'm not that concerned, I guess"

The Communication:

Elon expressed his unhappiness "in stronger terms" than just saying the deal was off

Timestamp: [19:24-21:00]Youtube Icon

📊 Did Elon Musk's Twitter Ban Actually Hurt Substack's Business?

The Surprising Reality of Platform Independence

The Timeline That Matters:

  • If it happened in 2019-2020: Would have killed the company
  • When it actually happened (2022): Minimal business impact

Why Substack Survived:

  1. Declining Twitter Dependency
  • Twitter's share of traffic had already been declining
  • Multi-year process of reducing Twitter importance
  • Network and discovery features already being built
  1. The Numbers Tell the Story
  • Despite individual writer trauma
  • Overall company metrics barely moved
  • Chris: "I don't think you'd be able to see where it happened"

The Misconception:

  • Elon's Assumption: Twitter was still Substack's primary growth driver
  • The Reality: Substack had already diversified traffic sources
  • The Outcome: Stressful for writers but not existentially threatening

Individual vs. Company Impact:

  • Very traumatic for writers with Twitter audiences
  • Stressful for customers who depended on it
  • Not visible in overall business metrics

Timestamp: [21:01-22:12]Youtube Icon

🎯 Why Did Substack Keep Building Notes When It Failed for Two Years?

The Founder Mode Persistence Story

The Two-Year Struggle:

Notes Feed Reality:

  • Launched as Twitter-like short-form content
  • Could link to long-form articles
  • Well-integrated quotes and sharing
  • Result: Didn't work at all for two years

The Metrics of "Failure":

  • Only a few thousand users
  • Hidden on second page of app
  • Used by "hardcore set of most intense writers"
  • Described as "quiet little corner" and "weird little thing"
  • Chris to skeptics: "This is great!"
  • Everyone else: "What are you talking about?"

Why a Professional Manager Would Kill It:

  • Not working after two years
  • Minimal user engagement
  • Hidden in the app
  • Team skepticism
  • Resource drain

Why Chris Kept It Alive:

The Miracle Perspective:

  • "Having built a messaging app before, it's a miracle it didn't totally die"
  • Expectation: Complete death
  • Reality: Life support was actually promising

The Essential Belief:

  • Core part of what they were trying to create
  • Kept insisting "it had to work"
  • Continued investing and iterating
  • Eventually got it working

This is pure Founder Mode: maintaining conviction in a feature everyone else would kill.

Timestamp: [22:13-23:43]Youtube Icon

💎 Summary from [15:19-23:43]

Essential Insights:

  1. Platform Dependency is Existential - Being downstream of "toxic sludge incentive factories" meant Substack couldn't control its own destiny
  2. Founder Mode Means Long-Term Courage - Building features that won't pay off for years, despite universal skepticism
  3. Timing Your Independence Matters - By 2022, Substack survived Elon's attack because they'd already reduced Twitter dependency

The Elon Musk Saga:

  • Midnight meeting at Twitter HQ to discuss acquisition
  • Days before Substack's social features launch
  • Retaliation included word bans, search blocks, and 5-second link delays
  • Personal fear about driving a Tesla while opposing Elon

Strategic Takeaways:

  • Diversify Before Crisis - Multi-year process of reducing Twitter dependency saved them
  • Build Despite Skepticism - Even Paul Graham thought their social features were a bad idea
  • Persistence Over Performance - Two years of "failure" eventually led to success
  • Professional Managers Would Fail - Only founders maintain conviction through years of poor metrics

The Notes Miracle:

  • Survived two years with minimal usage
  • Hidden on second tab of app
  • Only thousands of users in a "quiet corner"
  • Chris's messaging app experience taught him survival itself was promising
  • Eventually became successful through pure persistence

Timestamp: [15:19-23:43]Youtube Icon

📚 References from [15:19-23:43]

People Mentioned:

  • Elon Musk - Twitter owner who tried to buy Substack, then retaliated when they launched competing features
  • Mark Zuckerberg - Facebook CEO whose algorithm changes could destroy writer livelihoods
  • Paul Graham - Y Combinator founder who thought Substack's social features were a bad idea
  • Hamish McKenzie - Co-founder who confirmed the 2022 timeline

Companies & Products:

  • Twitter/X - Platform that banned "Substack" and delayed links after failed acquisition
  • Facebook/Meta - Example of platform dependency risk with algorithm changes
  • Tesla - Chris's car that made him wonder about Elon's potential retaliation
  • The New York Times - Only other site besides Substack to get 5-second delay treatment

Features & Products:

  • Substack Notes - Twitter-like short-form feed that took two years to gain traction
  • Substack Mobile App - Part of the independence strategy despite being "obviously very hard"
  • Group Subscriptions - Feature they eventually built after manual sales

Concepts & Frameworks:

  • Founder Mode - Ability to persist through years of failure that professional managers wouldn't tolerate
  • Platform Dependency - The existential risk of relying on other platforms for discovery
  • Long-term Greedy - Investing in features with multi-year payoff horizons
  • The Voldemort Effect - When platforms ban mentioning competitors

Timestamp: [15:19-23:43]Youtube Icon

🎯 How Do Founders Decide Which Features Must Exist No Matter What?

The Core Philosophy of Founder Mode

The Two Modes of Building:

Mode 1: Experimentation

  • Try lots of stuff
  • Hit a wall? Give it up
  • Move to something else
  • Very reasonable approach
  • Right thing to do in most cases

Mode 2: Must-Work Conviction

  • Decide certain things must work
  • Apply yourself over years to figure it out
  • Willing to persist despite poor metrics
  • Only accessible to founders with vision

Chris's Framework:

"You have to be able to know the difference between things that you're trying to figure out if they will work and things that you have decided that they must work"

The Founder Mode Advantages:

What a Non-Founder Wouldn't Do:

  1. Build social features in the first place
  2. Get in a "pissing match" with Elon (even if one-sided)
  3. Keep a failing feature alive for two years
  4. Write a manifesto as the first step

The Payoff:

"There are great things that you can build that are only accessible in that second mode"

This distinction between experimentation and conviction is what separates founder-led companies from professionally managed ones.

Timestamp: [23:43-24:50]Youtube Icon

✅ Is Substack Still Banned on Twitter/X?

The Current State of Platform Relations

The Resolution:

  • Word "Substack" - Can now be said on Twitter
  • Links - Work normally again (no more 5-second delays)
  • Search - Substack is searchable again

The Bigger Problem:

Links Are Dead Everywhere:

  • Not just Substack links
  • All external links deprioritized on social platforms
  • Chris: "Links are kind of dead across the board now"
  • "We're in the same boat as everyone else, unfortunately"

The Silver Lining:

Independence Achieved:

  • "You don't have to use Twitter anymore"
  • "You can open up the Substack app"
  • Justin Kan endorsement: Really likes and uses Notes
  • Substack now has its own discovery ecosystem

The platform war ended not with victory but with independence - exactly what Substack was building toward.

Timestamp: [24:51-25:16]Youtube Icon

👥 Who Is the Ideal Substack Creator and What Makes Them Successful?

The Cult Following Formula

The Non-Answer Answer:

"There's no such thing as a normal Substack user"

Substack as an "Index Fund of Culture":

  • Staggering breadth of topics
  • Every conceivable subject matter
  • No single typical user profile

The Common Thread - Creators Who Can Build:

Cult Followings

  • Intensity matters more than size
  • How much people care > how many people
  • Deep value to specific audiences
  • Readers who truly love the work

The Ideal Creator Profile:

  • Someone who generates intense loyalty
  • Creates content people deeply value
  • Builds meaningful connections with readers
  • Produces work readers actively seek out

The Audience Profile:

People who want:

  • Deep and real content
  • Smart long-form material
  • Substantive over superficial
  • Quality over viral moments

The Paul Graham Paradox:

  • Jessica suggests Paul Graham epitomizes the ideal Substack creator
  • Chris confirms but notes: "He hates this idea. He still thinks it's not working"
  • PG remains on his Yahoo-hosted blog despite being the perfect Substack archetype

Timestamp: [25:17-26:35]Youtube Icon

🎙️ How Does Substack Work for Podcasters?

The Complete Podcast Platform Solution

Basic Podcast Hosting:

  • Publish like any other podcast host
  • Distribution everywhere: Spotify, Apple Podcasts, all platforms
  • Completely free to use
  • Full podcast hosting capabilities

The Unique Advantage:

Email List Building:

  • Listeners can subscribe like any other Substack
  • You get their email addresses (key differentiator)
  • Direct communication channel with audience
  • Not dependent on podcast platform algorithms

Additional Benefits:

  1. Direct Communication
  • Write notes to all podcast subscribers
  • Perfect for season announcements
  • Jessica's use case: "Hey, it's coming next month"
  1. Substack App Discovery
  • Users discover clips and episodes
  • Built-in sharing and discussion features
  • Native audience within Substack ecosystem
  1. Optional Monetization
  • Can add paid subscriptions if desired
  • Same infrastructure as written content
  • Flexible business model options

The Strategic Value:

Unlike traditional podcast platforms, Substack gives podcasters ownership of their audience relationship through email - solving the same discovery problem for audio that they solved for writing.

Timestamp: [26:36-27:27]Youtube Icon

💎 Summary from [23:43-27:50]

Essential Insights:

  1. Must-Work vs. Might-Work - Founders uniquely possess the ability to decide certain features must exist and persist for years to make them work
  2. Platform Independence Achieved - Substack no longer needs Twitter; they built their own discovery ecosystem
  3. Intensity Over Size - Success on Substack comes from cult followings where depth of engagement matters more than audience size

The Founder Mode Formula:

  • Know the difference between experiments and convictions
  • Apply yourself for years to make essential features work
  • Build things only accessible through long-term conviction
  • Ignore reasonable advice when it conflicts with core vision

Current Platform Status:

  • Twitter/X relations normalized - No longer banned or throttled
  • Links dead everywhere - Industry-wide problem, not Substack-specific
  • True independence - Users can discover content entirely within Substack

The Ideal Substack User:

  • Creators: Those who build cult followings with intense reader loyalty
  • Readers: People seeking deep, real, smart long-form content
  • Philosophy: "Index fund of culture" with incredible breadth

Podcast Platform Features:

  • Free hosting with universal distribution
  • Key differentiator: Get subscriber email addresses
  • Direct communication with audience between episodes
  • Discovery through Substack app ecosystem

Timestamp: [23:43-27:50]Youtube Icon

📚 References from [23:43-27:50]

People Mentioned:

  • Justin Kan - Twitch co-founder who endorses and actively uses Substack Notes
  • Paul Graham - Y Combinator founder who epitomizes ideal Substack creator but "still thinks it's not working"
  • Elon Musk - Referenced regarding the platform conflict resolution
  • Jessica Livingston - Co-host interested in podcast features for seasonal announcements
  • Carolynn Levy - Co-host of The Social Radars podcast

Platforms & Services:

Podcast Features:

  • Substack Podcast Hosting - Free hosting with email list building
  • Notes Feature - Social discovery within Substack
  • Subscription System - Optional monetization for podcasters

Concepts & Frameworks:

  • Must-Work vs. Might-Work - Core founder mode distinction
  • Index Fund of Culture - Chris's description of Substack's breadth
  • Cult Following Model - Intensity over size philosophy
  • Platform Independence - Achievement of self-sufficient discovery

Timestamp: [23:43-27:50]Youtube Icon