long-form-interview· Chris Best, Hamish McKenzie

How Chris Best & Hamish McKenzie Built Substack — Make the Reader the Customer

Substack's structural bet was to reverse the platform economics of the internet — make the reader (not the advertiser) the paying customer, and give the creator ownership of the audience relationship; this business-model choice is what moderates content, protects founder independence from giants like Elon Musk, and allows Substack to stay in control of its financial destiny.

substackmediacreator-economynewslettersfounder-psychology90% confidence

Why this is in the corpus

Unusual 2-founder account of the founding mechanics behind a media platform now reportedly at 5M+ paid subscriptions, with specific named plays (Bill Bishop Guinea-Pig launch, Fire-Emoji writer scoring), a verbatim refusal of Elon Musk's offer to buy Substack and install Chris Best as X CEO, and Chris Best's explicit retrospective on what Kik got wrong (no business model, platform-dependence).

Summary for skimmers

Chris Best's Kik journey (BlackBerry Messenger-style app that hit 300M users, then Blackberry patent-sued them and expelled them from the app store, then crypto Hail-Mary monetization); Hamish McKenzie's path from NZ journalism → Hong Kong Timeout → Tesla in-house journalist (fired after relationship with Elon deteriorated) → Musk biography → Kik consulting; their meeting; the "so what, what's the solution?" essay edit that became Substack; Ben Thompson / Stratechery as template; Bill Bishop's launch day that hit six-figure ARR and got them into YC; Fire-Emoji writer-scoring methodology; the COVID-era 6x growth and the Andrew Sullivan / Taibbi / Weiss "getaway vehicle" defections; Elon's 2023 attempt to acquire Substack AND his simultaneous suppression of Substack links on X; the current 5M paid sub scale.

Briefing

What survives the editorial filter

This page should feel like a smart colleague already listened for you and left only the operating logic worth keeping. Not everything said in the episode makes it through.

Trust signal

direct_practitioner_account

Guest type: practitioner.

Best used for

Business-model design, creator-platform economics, first-customer play, Y Combinator arc, content-moderation stance, platform-risk lessons from Kik, Elon acquisition refusal.

Hold lightly

No explicit downgrade reason stored yet for this episode.

Principles

Durable claims that survive beyond the speaker's biography — each with explicit limits, transferability judgment, and evidence.

Principle

Have a business model from day one — "grow first, monetize later" is survivor-biased

Kik reached 300M users without a business model, then tried a crypto Hail-Mary and collapsed. Survivor-bias examples (WhatsApp) make growth-first look viable, but most ungenerated-revenue growth stories end at Kik, not at $22B acquisitions. A business model from day one is a discipline that shapes every product decision downstream.

“Just have a business model... that worked for some of the biggest companies in the world — that worked for WhatsApp, who sold for 22 billion. So I dont say that as a criticism to say we were stupid... but it did leave me determined to operate in a different way this time.”Chris Best

Principle

Keep the main thing the main thing

A company without a clear core is permanently in "what should we pivot to" mode, which consumes strategic attention that should be spent making the core actually work. Substack explicitly fights this by defining Substack AS the direct-subscription relationship, and treating every other feature as in-service to that core.

“Theres like a core of what Substack is and like thats the thing. At Kik... we were always kind of unmoored, we were always thinking about like what are we gonna turn this into? But there was a lot of kind of like trying to figure out the next thing instead of making the main thing actually work.”Chris Best

Principle

Build around the creator, not around the format

Platforms built around a format (Facebook = text, Instagram = photos, Snapchat = disappearing photos, Medium = articles) die with their format; Substack built around the creator relationship, so the platform absorbs format shifts (text → audio → video) without losing the audience asset.

“Other things are built around formats. Substack is built around you. Its built around the direct relationship. Its built around owning your audience, owning your work, having your own space on the internet.”Chris Best

Principle

Raise when you don't need to, so you stay in control of your financial destiny

Substack's position that "we don't need to raise money again" is the foundation of every other strategic choice — including refusing Elon Musk's acquisition offer and absorbing the Twitter link-suppression attack. Running the company so that fundraising is an accelerant but not a necessity preserves founder control against exactly these pressure moments.

“The advantage of having a business model is you can be in control of your financial destiny... we dont need to raise money again. Were not on this clock. We are in control of our financial destiny.”Chris Best

Principle

Make the end-user the customer, not the advertiser

In a media platform, whoever pays determines what the product optimizes for; Substack made readers the paying customer so the platform optimizes for reader-writer relationships rather than for advertiser-reach, which structurally moderates content and aligns incentives that advertising models cannot.

“The core insight he had was that you should make readers the customers instead of advertisers the customers. And if you change that core dynamic, especially if you monetize the relationship over time through a subscription, then different things are possible.”Hamish McKenzie

Principle

The creator should own the audience relationship, not the platform

A creator business dies when the hosting platform changes its algorithm or charges again for reach (Facebook pages). The right platform design gives the creator the direct subscription relationship — subscribers subscribe to the writer, not to Substack — so the creator can take the audience anywhere if the platform breaks.

“When you subscribe on Substack, you dont subscribe to Substack, you subscribe to Guy or whoever. They should own the connection, it should be their relationship.”Chris Best

Principle

Timing determines whether a competitive attack is fatal or forgettable

Elon Musk's 2023 attempt to kill Substack via Twitter link-suppression would have been existential in 2019-2020 when Twitter was Substack's primary traffic source. By 2023, Twitter-share of Substack traffic had been declining for years — the same attack barely registered. Competitive defense is measured in channel-diversification-years, not in features.

“There wouldve been a time in Substack history when that was true. Like if this had happened in 2019 or 2020, like yeah, I think that really wouldve set Substack back a lot. But by the time it went down, the share of Substack traffic coming from Twitter had been on a steady decline for years.”Chris Best

Frameworks

Reusable systems and operating models — including when they help and when they break.

Framework

Fire-Emoji Audience Intensity Scale

A 1-4 fire-emoji ranking tool for evaluating writers/creators to recruit — score them by audience devotion rather than audience size; 3-4 fires = "they'll work on Substack," 1 fire = audience doesn't really care. The framework inverts the default "bigger is better" heuristic for creator acquisition.

“We developed this tool that allowed us to put fire emojis beside the names of the ones who had these really devoted audiences... if you had three fire emoji, okay, we are pretty sure you're gonna work on Substack. If you had four fire emoji, we knew you had the kind of audience that would really respond well.”Hamish McKenzie

Framework

Getaway Vehicle Positioning

Position your product as the escape route for a visible class of people stuck inside an institution that is failing them — Substack's "getaway vehicle" pitch to institutional journalists in 2020 ("fuel it up, have the engine idling, claim your handle just in case") converted political/institutional pressure into creator-acquisition flywheel.

“Think of Substack as your getaway vehicle. You dont have to get in it right now, but fuel it up, have the engine idling, create your account, claim your handle, have this thing ready just in case something unexpected happens.”Hamish McKenzie

Signals

What appears to be shifting, for whom it matters, and what happens if you ignore it.

Signal

Media power has redistributed from institutions to individuals at a structural level

CNN evening newscast ~500K viewers; 140,000 YouTubers have audiences at least that large. Substack has 5M+ paid subscriptions — more than the Washington Post, Atlantic, and New Yorker combined. This is structural (driven by business-model shifts and creator-owned audience relationships), not cyclical — institutional media power is not coming back.

“Nowadays the average evening newscast on CNN gets around half a million viewers... yet there are 140,000 YouTubers with audiences at least as big. Once mighty newspapers, radio news magazines and TV broadcasts have largely lost their influence and power.”Guy Raz (host framing)

Opportunities

Only included where there is a buyer, a real wedge, and a plausible revenue path — not vague idea theater.

Opportunity

The "next Ben Thompson" — infrastructure arbitrage for sophisticated solo operators

Wherever a sophisticated solo operator is successfully running a profitable business by stitching together 15-20+ separate tools (Ben Thompson: 19 tools, $1M+/yr from Stratechery), there is a consumer platform opportunity. The operator is doing the product-manager work for you; the only question is whether you can package their stack into one button.

“He had to be this triple unicorn of a great analyst and a great writer and a great entrepreneur and a great editor and a great technology wrangler. And we were just like, oh, thats why nobody does this. Thats way too hard.”Hamish McKenzie

Lessons still worth keeping

Useful takeaways that did not fully clear the bar for durable principle status.

Lesson

Tesla in-house — you can go from teacher's pet to persona non grata in weeks under a mercurial CEO

Hamish McKenzie was hired by Elon Musk directly after a phone call about a potential biography; within a year he went from "teacher's pet" to "persona non grata" over a battery-cleanliness report Elon didn't like and some social-channel tweets. Operating inside a founder-driven, mercurial-CEO environment is structurally high-variance — a single piece of work the CEO doesn't like can end your standing.

“I started off as teachers pet, but like is what happens with many people sort of quickly became persona non grata to Elon... the report didnt come out the way he wanted. I took over the social channels for Tesla and did some tweets that he didnt like. I got an angry email from him.”Hamish McKenzie

Lesson

Kik — 300M users without a business model died via Blackberry patent suit + crypto Hail Mary

Kik reached ~300M users by ~2015, valued over $1B. BlackBerry then patent-sued and expelled them from the app store — half their users, but functionally 95% of reach, gone overnight. With no monetization, the founders launched a crypto token as a last-resort monetization, which Chris Best did not believe in, so he left. Lesson: platform dependency + no business model is the worst possible combination, and regulatory/patent threats compound both.

“They kicked us out of the Blackberry app store... if youre a messaging app and your big drive is half on Blackberry and half on iPhone, if you lose half your users, you dont actually lose half your users. You lose like 95% of your users.”Chris Best

The Plays

Try these this week

Verb-first executable actions — each one tied to a stated outcome in the episode.

Guinea-Pig First-Customer Launch — Find the Operator Already Saying "I Want To"

Outcome: Find a sophisticated solo operator publicly telegraphing "I want to do X but I can't / haven't gotten around to it yet" (Substack found Bill Bishop repeatedly saying he'd paywall his free China newsletter). Slide into their inbox, offer to build the product AROUND their specific need, use THEIR launch as your product launch. Bill's launch day hit six-figure ARR in hours — that single data point got Substack into YC despite having applied at $0 revenue.

“Bill had been talking in his newsletter... about how hes gonna introduce a paywall soon... I jumped into his inbox and said my friend and I are starting this thing, which is kind of like well take care of everything for you. Would you be interested in being a Guinea pig for this? And he luckily said yes. And so we got to launch with kind of the ideal first customer.”
— Hamish McKenzie

2-4 weeks from cold email to live launch; Day-1 revenue signal is the event per

Scripts

Before you start

· A specific target-operator publicly telegraphing the exact demand your product addresses
· Day-1-shippable MVP (not a future roadmap)
· Willingness to aggressively customize the first launch around one operators needs

go-to-marketpre-seedseed

Fire-Emoji Writer Scouting — Score Creator Acquisition Targets on Audience Intensity

Outcome: Build an internal creator-acquisition scoring tool that ranks prospective recruits on audience DEVOTION (1-4 fire emojis) rather than audience size. Target only 3-4 fire creators. When pitching them, explicitly walk them through the math their audience size implies — most creators cannot do the multiplication themselves and won't act on intensity until you show them.

“We developed this tool that allowed us to put fire emojis beside the names... its surprising how much we had to make that obvious to writers actually. If you get 10,000 paying subscribers paying 50 bucks a year, thats enough to actually like really make serious money.”
— Hamish McKenzie

2-week initial scoring pass; ongoing rolling outreach per

Scripts

Before you start

· Internal scoring rubric defining what 1/2/3/4 fires mean for your vertical
· Conversion math specific to your platforms economics
· A creator-support team that can onboard 4-fire creators hands-on

go-to-marketseedseries-a

Decision Moments

Actual decisions, real outcomes

Specific decisions narrated in the episode with their outcomes and transferable lessons.

In early 2023 — days before Substack launched Notes — Chris gave Elon Musk a courtesy heads-up on the call. Elon responded by offering to acquire Substack and make Chris CEO of Twitter/X, saying he didnt want the CEO role and needed one.

Did: Declined. Chris went through an "accelerated process of thinking about that" and concluded Elon would still run the place, make all decisions, and not let Substack stay a neutral free-speech platform.Outcome: Elon took the Notes launch (and implicitly the refusal) as a "no." Within 24 hours Substack links were suppressed on Twitter; searching for "Substack" briefly broke. Musk said "we can bury you." But by 2023 Twitter-share of Substack traffic had been declining for years — the attack was absorbed. Linda Yaccarino was hired as X CEO weeks later.

The price and title of an acquisition are irrelevant if the acquirer removes your ability to execute the mission — acquirers with strong operator identities cannot give up decision authority even when they hire CEOs.

Part of an emerging decision pattern across multiple episodes

Bill Bishop had been running a free China newsletter (Sinocism) for 5 years, was talking publicly about paywalling it "soon" for months without actually doing it. Chris Best and Hamish McKenzie had a working MVP but no first customer.

Did: Hamish jumped into Bill Bishops inbox uninvited with a "be our Guinea pig" offer — Substack would handle all the paywall infrastructure so Bill could focus on writing. Bill agreed. Chris duct-taped Stripe to enable it in weeks.Outcome: Bills launch day hit six-figure ARR within hours. That single customers revenue number reframed Substacks YC application (originally at $0 revenue) — YC accepted, seed investors followed, and "you just need 4-5 more Bill Bishops" became the thesis (which turned out to be harder than YC predicted but the momentum carried them).

The ideal MVP launch is a bespoke product for one sophisticated operator who has already stated the demand — their launch moment becomes your launch moment, and one customers revenue day converts investor narrative from thesis to proof.

Part of an emerging decision pattern across multiple episodes

Kik had reached ~300M users globally by ~2015, valuation >$1B, but had no working business model. Pivots to monetization were failing.

Did: Launched a cryptocurrency/ICO as a monetization Hail Mary, partly to raise money and partly to answer "what do you do with a free messenger that lots of people use but makes no money."Outcome: Chris Best did not believe in the crypto direction and left in 2017. Kik subsequently continued to decline; WhatsApp (cross-platform from day one) won the messaging category and exited at $22B to Facebook. Kik is now a cautionary tale.

Missing business model + platform dependency is the worst combination a consumer company can have; when the rescue monetization diverges from founder conviction, founders leave, which accelerates the decline into terminal.

Part of an emerging decision pattern across multiple episodes

In 2020, with the pandemic in full swing and institutional journalism under pressure (de-platformings, forced departures, advertiser boycotts), Substack had 100-ish employees, $15M Series A from a16z, and rapidly growing usage.

Did: Repositioned Substack publicly as a "getaway vehicle" for institutional journalists — the pitch: fuel it up, have the engine idling, claim your handle, be ready in case something unexpected happens.Outcome: Andrew Sullivan, Matt Taibbi, Barry Weiss, and Jennifer Rubin all defected from major institutions to Substack within 18 months. Substack grew ~6x in 2020 alone. The getaway-vehicle framing converted external political pressure into zero-CAC creator acquisition.

Position your product as the escape route for a visible class of people stuck inside an institution that is failing them — pre-enrollment before the escape is needed is the critical step; by the time the crisis hits, the decision is already made.

Part of an emerging decision pattern across multiple episodes

Tensions surfaced

Contradictions and trade-offs the episode raises — judgment calls a thoughtful operator has to navigate.

Tension

Content-moderation minimalism vs. external pressure to suppress objectionable writers

Substack's position — the business model moderates content better than rules do — collides with periodic public pressure to de-platform specific objectionable voices (The Atlantic's "Nazi problem" article). The tension has no clean resolution: enforce applicable rules (no incitement, doxing, spam) but refuse to change enforcement based on public pressure; accept that this will cost you favorable coverage during every moderation cycle.

“Our stance on this is, look, we have a set of content policies. If something comes to our attention that is against the broadly applicable Substack rules, were gonna take action. But were not changing what we enforce based on pressure.”Chris Best

Corpus connection

Where this episode fits for retrieval

What kinds of decisions this briefing is best pulled into.

Primary decisions

• product-design
• go-to-market
• fundraising
• competitor-response

Temporal flag

timeless