May 27, 2016 · 26m · 20vc
20VC: The Information's Jessica Lessin on The Future For Online Journalism & The Benefits Of A Subscription Based Business Model
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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, Jessica Lessin, founder and editor-in-chief of The Information, discusses the state of digital journalism and the strategic power of a subscription business model. She outlines how focusing on deep, original reporting for key industry decision-makers creates a sustainable alternative to ad-driven media platforms.
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 29% of the talking time here. How this is scored →
Harry as informed peer 2.7 Guest teaching 2.7 Guest disagreement 0.7 Harry pushing back 0.7
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 5:35 Reframing Andreessen's quality premise
Jessica directly challenges the premise of Marc Andreessen's comparison between print and blogs, arguing that evaluating quality abstractly without considering target audience utility is flawed.
Hardest push from Harry ▶ 5:22 Harry citing Andreessen's critique of journalismHarry brings up Marc Andreessen's provocative statement that print journalism is converging with Wikipedia and blogs to challenge Jessica's stance on publishing quality.
Biggest teaching moment ▶ 7:32 Dismantling reader demographic assumptionsJessica corrects Harry's assumption that her target reader is a young San Francisco tech bro, explaining that her subscriber base actually consists of top-tier enterprise executives and tech founders.
Harry holds his own ▶ 8:25 Citing niche media competitorsHarry demonstrates strong domain knowledge of independent tech media by naming specific prominent analysts like Ben Thompson and Ben Evans when framing the market landscape.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Founding The Information & Mission | 2 | 1 | 0 | 0 | Harry asks standard background questions about founding The Information and takeaways from Jessica's time at the Wall Street Journal. Jessica provides detailed, collaborative answers on her mission and subscription approach. | |
| The Shift Toward Shallow Media Coverage | 4 | 5 | 2 | 2 | Harry cites Marc Andreessen's statement comparing print journalism quality to blogs and Wikipedia. Jessica gently reframes the premise, educating Harry that quality should be measured by audience utility rather than media format. | |
| Profile of The Information's Target Subscriber | 4 | 4 | 1 | 1 | Harry proposes a narrow reader demographic trope (20 to 35 male San Franciscan) which Jessica gently corrects by detailing their high-level executive subscriber base. Harry shows good industry context by citing Ben Thompson and Ben Evans. | |
| Content Creation Strategy & Investigative Reporting | 2 | 2 | 0 | 0 | Harry asks about investigative reporting strategies versus press release regurgitation. Jessica outlines her team's deep sourcing and subscriber-focused editorial approach. | |
| Defining Great Reporting & Journalistic Styles | 2 | 2 | 0 | 0 | Harry asks what defines a great reporter and why subscriptions are superior to ad models. Jessica details three distinct journalist personas and explains why subscription models align best with editorial integrity. | |
| Overcoming Friction in Subscription Onboarding | 3 | 4 | 2 | 2 | Harry probes whether paywall friction deters onboarding subscribers. Jessica reframes paywall friction as an intentional quality filter for a targeted decision-maker community. | |
| Leveraging Email Marketing for Growth | 2 | 1 | 0 | 0 | Harry moves through email growth strategies and a quickfire round covering books, objectivity, and Snapchat. The tone is highly collaborative and brisk. |
Statements from this episode (15)
The Wall Street Journal Has Shifted Away From Exclusive Reporting
“And I think the journal and other publications have broadened their focus away from that kind of journalism, but it's something that I've certainly taken from the journal”
Half of The Information's Early Reporters Came From The WSJ
“Half our reporting team you know, spent decades collectively at the journal as well at the information.”
The Digital Media Industry Is Becoming Increasingly Broad and Shallow
“I think most of it comes down to the fact the industry is getting very broad and shallow. And what I mean by that is there are more publications by the day, but they're all essentially covering the same kind of news for mass audiences.”
Media Quality Is Defined by Audience Value, Not the Medium
“Quality isn't something that is abstract. It's based on the value of that information to a particular audience.”
All Top 10 U.S. Tech Unicorn Founders Subscribe to The Information
“Our subscribers range from Entrepreneurs who are just starting out on their first Y Combinator company, to executives in the management teams at the most highly valued public tech companies, to 10 out of 10 of the founders of the most highly valued U.S. Privat…”
Media Outlets Compete With All Time-Occupying Content, Including Instagram
“Anything that takes our subscribers time that they find valuable from Instagram to The Economist is in some ways competitive, right? I mean, I think that is actually the bar for anyone in the media business.”
Original Tech Journalism Is Not a Zero-Sum Market
“If you're writing stories that have new information about business and technology, it's not like our audience will only read one of those. They literally have a thirst for as much that's valuable to them as humanly possible. It's not like there are only X hour…”
Digital Publications Waste Great Reporters on Trending Twitter Stories
“So many other publications are having their great reporters spend their time on less than great stories. Again, on these stories that are real-time, regurgitation, written because, you know, they're trending on Twitter, and God forbid a publication doesn't hav…”
Media Companies Lacking Must-Read Content Will Fail Long Term
“And if you're not writing stories that people feel like they have to read, you know, you may get blips and traffic here and there. You may even grow your audience for a couple of years. But you're not going to be around years and years and years from now.”
Subscriptions Are the Only Media Model Aligned Purely With Readers
“And I think if you're in a world where you're dependent on advertising, you're going to serve multiple masters. You're going to serve the traffic master, the advertising master. You know, if you're dependent on events, you're going to serve the sponsorship mas…”
Subscription Media Scales on Product Value, Not Sales Capacity
“It's also insanely scalable, right? That doesn't tap out at how, you know, many business development deals you can cut or how many ad packages you can sell, right? It taps out based on the inherent value of the product.”
The Information Will Not Build Products for a Billion-User Audience
“I think if you're writing a publication or building a tech product for a billion people, you know, that's going to look a certain way, and we don't want to build that product.”
The Information's Early Growth Was Organic and Eerily Linear
“So actually to date, our growth has been The organic word of mouth side and incredibly linear, sort of eerily linear.”