Jun 12, 2020 · 31m · 20vc
20VC: Substack Founder Chris Best on The Future of Public Journalism, Why The Economics Of Attention Have Been Flipped & Why Micropayments For Content Will Not Work
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of The 20 Minute VC, host Harry Stebbings interviews Substack founder and CEO Chris Best about transforming media monetization, the mechanics of the attention economy, and lessons learned transitioning from CTO at Kik to building a creator-centric publishing platform.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 33.1% of the talking time here. How this is scored →
Harry as informed peer 3.1 Guest teaching 3.4 Guest disagreement 0.6 Harry pushing back 1.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 19:42 Rejection of the subscription ceiling premise
Chris lightheartedly counters Harry's claim that readers will not pay for many newsletters by pointing out that some power users already subscribe to 25 Substack authors.
Hardest push from Harry ▶ 10:11 Adding discovery to the trust problemHarry explicitly steps in to reframe Chris's thesis on content trust, asserting that discovery remains an equally major problem in the media ecosystem.
Biggest teaching moment ▶ 17:52 The evolution of attention economicsChris articulately educates the audience on the historical shift from pre-internet boredom to modern attention saturation where high-signal paid content wins.
Harry holds his own ▶ 19:19 Challenging subscription overloadHarry demonstrates keen market awareness by directly challenging the scalability of creator subscriptions against finite consumer budgets and attention.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Chris Best's Background and the Founding of Substack | 3 | 3 | 0 | 0 | Harry sets the stage and prompts Chris for Substack's founding story. Chris explains his transition from Kik CTO to writing a media essay that was critiqued by his friend Hamish, sparking Substack's core thesis. | |
| Lessons from Kik and Strategic Choices for Substack | 2 | 3 | 0 | 0 | Harry asks questions crowdsourced from investors like Ted Livingston and Seth Bannon. Chris details taking product thoughtfulness from Kik while establishing immediate monetization for Substack. | |
| Public Journalism, Trust, and the Substack Model | 4 | 4 | 1 | 4 | Chris explains how paid newsletters preserve free public posts, framing trust as journalism's main bottleneck. Harry intervenes to point out that content discovery is an equally severe problem. | |
| The Failure of Micropayments and Substack's Product Roadmap | 4 | 4 | 1 | 3 | Harry brings up previous conversations about micropayments to probe why the model fails. Chris explains how decision friction over small transactions destroys the user experience. | |
| Platform Incentives and the Flipped Attention Economy | 4 | 5 | 1 | 2 | Harry prompts Chris to elaborate on incentive design and the flipped attention economy. Chris gives a masterclass on how algorithm-driven engagement differs from direct consumer payment. | |
| Subscription Limits and Bundling Economics | 4 | 4 | 2 | 5 | Harry presses Chris on consumer capacity limits, arguing people cannot manage dozens of individual paid subscriptions. Chris acknowledges subscription caps while introducing bundle economics. | |
| Transitioning from CTO to CEO, Hiring, and Investor Value | 3 | 3 | 0 | 1 | Harry steers the talk toward executive growth, hiring, and venture advice. Chris discusses replacing himself with a better CTO and using high talent competition as a filter for mission-driven hires. | |
| Quickfire Round: Books, Superpowers, and First Checks | 2 | 2 | 0 | 0 | A fast-paced quickfire round covering favorite books, personal weaknesses, and angel investors. The tone is highly agreeable and collaborative. | |
| Substack's Five-Year Vision for Culture and Creation | 2 | 3 | 0 | 0 | Chris delivers a visionary closing monologue on fixing the financial model for human culture, linking his work at Substack to the world his newborn son will grow up in. |
Statements from this episode (13)
Best: Platforms dictate user behavior by controlling what actions get rewarded
“You can't really change human nature. You can't Change what people want, or how they think about the things that you're building for them, but despite not being able to change that, you can change the behavior that gets rewarded, the behavior that ends up flou…”
Best: The shift away from traditional media will not reverse post-pandemic
“COVID has just accelerated that pre-existing trend. And that's something that's not gonna, you're not gonna turn back time on that after that happens.”
Best: Substack advises writers to publish their best work for free
“Our emphatic advice to writers is take your best stuff, take your most impactful stuff, and publish that for free.”
Best: The core problem for modern media consumers is establishing trust
“Nobody has the problem in That I don't have enough stuff to read, or I can't find a piece that's written about a topic that I care about, or I can't find this information. The problem that people have is, can I trust this?”
Best: Digital media will bifurcate into global juggernauts and niche publications
“No, I think that's exactly right. I mean, I think this is the thing you get when the internet creates kind of a global marketplace for things is you want to be the best in the world at something. And that either means being the best in the world by being reall…”
Best: Micropayments fail because decision fatigue outweighs small transaction amounts
“I think that micropayments, as we sort of traditionally think of them as like, I'm going to quickly decide whether I want to spend 20 cents unlocking this thing, just don't work on sort of a fundamental product level. I think when you decide to pay for somethi…”
Best: Engagement algorithms cannot solve clickbait through additional moderation rules
“If your underlying algorithm is maximizing for engagement, you're not going to be able to, like, turn up the, like, don't make bad content dial in the algorithm and have, like, a permanent fix for that.”
Best: Direct subscriptions yield higher quality media than engagement algorithms
“A system where people are paying directly to writers they trust is going to create better, more trustworthy content, more trustworthy relationships, more valuable culture at the end of the day than a system where people are trying to like game the engagement a…”
Best: Consumers pay more for single Substack writers than Netflix subscriptions
“People are willing to pay more to subscribe to one writer on Substack than they'll pay for, like, Netflix, because this sort of relationship that they've built up over time reading somebody has so much value to them.”
Best: Some users subscribe to 25 individual Substack newsletters
“There are people who subscribe to 25 sub-stacks.”
Best: Bundle economics will become important for subscription newsletters
“I think, you know, bundle economics are very real. That's definitely a thing that will become interesting.”
Best: Imposed content bundles destroy direct reader-writer relationships
“The trick is that you have to do it intelligently. You can't come in and impose bundles on people, because then it kills that golden goose of the direct relationship between readers and writers.”
Best: Society is massively underinvesting in funding independent creators
“I believe that it's sort of massively too little and that the ecosystem we have for a Funding creators, and a lot of it is valuing and funding creators, but really the net thing is funding creators in such a way that it causes great work to be done, that it ca…”