May 12, 2025 · 1h 18m · how-i-built-this
Substack: Chris Best and Hamish McKenzie
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
Guy Raz interviews Substack co-founders Chris Best and Hamish McKenzie on How I Built This, exploring how their prior startup trials and journalism backgrounds inspired them to create a direct-subscription platform that disrupted legacy media and empowered independent writers.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Guy holds 39% of the talking time here. How this is scored →
Guy as informed peer 4.4 Guest teaching 2.4 Guest disagreement 0.8 Guy pushing back 0.7
speaking balance: gold is Guy, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 1:00:26 McKenzie rejects political skew framing
McKenzie directly counters Raz's suggestion that Substack's top writers lean libertarian center-right, telling Raz to check the US politics leaderboard to see hard-left and hard-right balanced equally.
Hardest push from Guy ▶ 59:46 Raz presses on Atlantic Nazi controversyRaz confronts Best with the specific Atlantic investigation regarding Nazi imagery and newsletters, forcing Best to justify Substack's content moderation enforcement.
Biggest teaching moment ▶ 1:09:44 McKenzie corrects metric terminologyMcKenzie explicitly interrupts to educate Raz on the vital industry distinction between active readers having paid subscriptions versus unique paying subscribers.
Guy holds their own ▶ 45:43 Raz drills down on Substack's unit economicsRaz breaks down the payment processing cut and 10% take-rate to challenge whether Substack's margins are too thin to sustain the business without higher platform fees.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Guy as informed peer | Guest teaching | Guest disagreement | Guy pushing back | Why |
|---|---|---|---|---|---|---|
| Chris Best's Early Tech Career and the Origins of Kik | 4 | 2 | 0 | 0 | Raz guides the narrative smoothly through Best's early engineering background and the transition from building a BlackBerry music player to Kik Messenger. | |
| The Rollercoaster Growth and BlackBerry Battles of Kik | 5 | 3 | 1 | 0 | Raz contributes context on Kik's user milestones and legal battles with BlackBerry, while Best recounts the intense operational pressure of being kicked off BlackBerry's app store. | |
| Leaving Kik and Seeking a New Direction | 4 | 2 | 0 | 0 | Raz inquires about Best's decision to exit Kik and his financial situation, before smoothly transitioning to Hamish McKenzie's background in New Zealand and Hong Kong. | |
| Hamish's Move to the US and Turbulent Stint at Tesla | 5 | 3 | 1 | 0 | Raz brings up his own past reporting on early Tesla roadsters, while McKenzie describes his whirlwind hiring and eventual falling out with Elon Musk. | |
| Hamish and Chris Meet at Kik | 3 | 1 | 0 | 0 | A relaxed, collegiate exchange where Best and McKenzie share the humorous story of sharing an 8 a.m. Corona before Best's CNBC Squawk Box appearance. | |
| The Media Manifesto and the Ben Thompson Epiphany | 4 | 3 | 1 | 0 | The co-founders debate their differing recollections of Best's initial media manifesto, then walk Raz through Ben Thompson's Stratechery model that inspired Substack. | |
| Mid-Roll Break 1 | 3 | 1 | 0 | 0 | Following the mid-roll, Raz probes how Best convinced McKenzie to abandon freelancing and partner up to build Substack despite initial reluctance. | |
| Designing Substack's Audience Ownership and Economics | 5 | 2 | 0 | 1 | Raz and the founders discuss platform lock-in and the structural failure of social platforms like Facebook and YouTube that control audience relationships. | |
| Bootstrapping and Launching with Bill Bishop | 4 | 3 | 1 | 0 | The guests explain the pivotal beta test with Bill Bishop's Sinocism, which generated six figures overnight and energized their Y Combinator pitch. | |
| Y Combinator, Early Seed Funding, and Pricing Mechanics | 5 | 3 | 1 | 2 | Raz questions the sustainability of Substack's 10% cut given the operational overhead, prompting Best to defend their pricing structure and top-of-funnel strategy. | |
| Founder Lessons: Monetization and Keeping the Main Thing | 4 | 2 | 0 | 0 | Raz reminds listeners that most YC companies fail, prompting Best to outline core takeaways from Kik regarding having a clear business model from day one. | |
| Mid-Roll Break 2 | 3 | 1 | 0 | 0 | The founders detail their proprietary 'fire emoji' scoring system used to identify writers with intensely loyal audiences on Twitter. | |
| Pandemic Acceleration and Becoming Media's 'Getaway Vehicle' | 5 | 2 | 0 | 1 | Raz contextualizes the 2020 pandemic and media turmoil that positioned Substack as a 'getaway vehicle' for prominent journalists leaving legacy institutions. | |
| Navigating Content Moderation and Free Speech Debates | 6 | 4 | 3 | 5 | Raz directly challenges the founders on platform governance, citing Atlantic reporting on Nazi newsletters and pushing on whether their top writers lean right, which McKenzie and Best firmly push back on. | |
| The Clash with Elon Musk and Substack Notes Launch | 5 | 3 | 2 | 1 | The founders detail Elon Musk's sudden buyout offer before the Substack Notes rollout, and the subsequent retaliatory suppression of Substack links across X. | |
| Reaching 5 Million Subscriptions and the Future of Media | 5 | 3 | 2 | 1 | McKenzie clarifies the difference between subscribers and subscriptions, and both founders share their philosophies on media decentralization versus luck and hustle. |
Statements from this episode (30)
Best: Waterloo's mandatory co-op program is more valuable than its classes
“The most important thing about Waterloo, though, is not actually what you learn in the classes, it's the fact that they have this mandatory co-op program.”
Best: Kik Messenger was used by 40% of US teenagers
“I mean, at one point, there was, I think, 40% of U.S. Teenagers were using Keck for a few years.”
Best: Losing half a cross-platform messaging network destroys 95% of users
“And if you're a messaging app, and your big drive is your half on Blackberry and half on iPhone, if you lose half your users, you don't actually lose half your users, you lose like, 95% of your users.”
Best: Kik launched a cryptocurrency to solve free messenger monetization
“In part to raise money, and in part kind of like as a, in answer to the question, what do you do if you have a very popular messenger that lots of people use, but you don't know how to make money from it?”
McKenzie: Elon Musk offered him a Tesla job instead of a biography
“I was pitching him the idea of this book, but Elon said, I don't know about the book. Maybe, but would you be interested in a job at Tesla?”
McKenzie: Tesla had a messy, cut-throat, throw-under-the-bus culture
“It's totally different from Tesla, which was messy and cut-throat and had to, like, throw everyone under the bus kind of culture.”
McKenzie: Media succeeds when readers replace advertisers as paying customers
“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 enough subscription, then different things are possi…”
McKenzie: Ben Thompson was earning over $1M annually from Stratechery in 2017
“We figured out, you know, through napkin math and guessing, basically, that he was already making more than a million dollars a year from that.”
Best: Audiences refuse to pay for internet content, except for favorites
“I devised this like parlor trick where when somebody told me they would never pay for something on the internet, I would say, well, who's your favorite writer? And they'd say, oh, you know, Guy Raz, or whoever. And then I would say, would you pay five bucks a …”
Best: Facebook charged creators to build audiences then charged again for reach
“And this had happened with Facebook pages at this point. They created a thing where people spent all this money getting people to like their Facebook page on the assumption that that meant they'd built up an audience. And then they said, oh, just kidding. Actu…”
McKenzie: Patreon proved audiences will pay directly for creators they love
“Yeah, Patreon, I think, is a hugely important company because it changed the culture. It showed not only that people will be willing to pay for content online, they'll be willing to pay for the artist or creator who they most love or trust.”
Best: Facebook's core issue is working too well without serving its users
“The problem with Facebook is not that it doesn't work, right? The problem with Facebook is that it works too well. And doesn't serve the people who use it. Right. Yes, it kills all the newspapers, but it's a massively successful business that takes, takes adva…”
McKenzie: Tech sector believed a billion-dollar company for writers was impossible
“2017, writers were not the sexiest customer base in the world. No one thought they were going to build a billion dollar tech company by serving writers. In fact, people were forsaking writers, forsaking the media, turning their back on that, they'd given up on…”
McKenzie: Spent his grandmother's inheritance on living expenses while bootstrapping Substack
“I spent all of it to just cover my salary for a few months before we raised a proper round of money from like more friends and family that could help us start to pay ourselves a little bit of a salary.”
Best: First publisher Bill Bishop made six figures on day one
“Bill's launch happened. And we had no, I had no idea what to expect, but he made like six figures his first day through this like duct taped, like stripe setup that I had built in the preceding weeks.”
McKenzie: Twitch co-founder Emmett Shear became an early Substack investor
“I remember on the first demo day we did, which is the one that's for YC alumni, Emmett Scheer came up to me and he said, Emmett Scheer, founder of, co-founder of Twitch, who was on the show a couple years ago, yep. Yeah, he's like, I look at you guys, I'm real…”
McKenzie: Substack reached 7,000 paid subscriptions by the end of Y Combinator
“By the time we Finished YC at the end of March. We had, we, 7000 paid subscriptions across the network that we could point to and say, look, this thing is working.”
McKenzie: Substack recruited writers with devoted followings over large overall audiences
“We looked for people that we thought weren't being well served by the dominant media structure, but actually had interesting things to say and had a devoted audience. And so it wasn't necessarily the people with the largest audiences. Maybe they'd have a small…”
Best: Writers rarely realize subscription earning potential until shown the math
“It's surprising how much you have to do that multiplication for people. Like, it's not that they can't do it themselves, it's that they won't do it. And the number of times I've had a conversation that's like, you know, so-and-so has 10,000 subscribers paying,…”
Best: Substack grew roughly sixfold during the first year of the pandemic
“I mean, we grew something like six X in that first year of the pandemic.”
Best: Substack was pitched to journalists as a media 'getaway vehicle'
“I had this speech that I would give to people at the time. I was like, think of sub stack as your getaway vehicle. You don't have to get in it right now, but like, Fuel it up, have the engine idling, like create your account, like claim your handle, have this …”
Best: Substack's direct subscriber model insulated the platform from advertiser boycotts
“I mean, a big part of it is the business model, right? Like the fact that we was paying subscribers, we didn't have Advertisers who were getting spooked and boycotting us, bringing us under pressure.”
McKenzie: Billions spent on social media content moderation failed to fix trust
“They've invested billions of dollars on this. They come up with these policy documents that are hundreds of pages long. And it doesn't appear to us like it has actually helped misinformation problems, or it's helped Reduce the level of harassment, or it's help…”
Best: Platforms should not decide what is right or who to trust
“I don't think our role as a platform on the internet should be to tell you what's right and what's wrong or who to trust and who not to trust. And it's a seductive idea that it should be that role. And a lot of platforms took that stance and it just didn't wor…”
Best: Substack does not change content enforcement based on public pressure
“If something comes to our attention that is against the broadly applicable substack rules, we're going to take action. But we're not changing what we enforce based on pressure.”
McKenzie: Musk offered to buy Substack and make Chris Best Twitter CEO
“And he responded by getting Chris on a call and saying to him, well, how about Twitter acquire Substack, and you, I'm looking for a CEO to run the company.”
Best: Substack traffic from Twitter had steadily declined for years by 2023
“By the time it went down, the share of Substack traffic that was coming from Twitter had been on a steady decline for years.”
Best: Substack has surpassed 5 million paid subscriptions
“I think we can say there's over five million now.”
Chris Best: Substack does not need to raise outside capital again
“We're not running the company to, like, turn a profit, but the thing that is true, and we've kept true pretty much the whole time, is we don't need to raise money again. We're not on this clock. We have, like, we are in control of our financial destiny.”