The State of Startup Media

A Newfound Republic of Letters

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Startup Storytelling

When I started thinking about startups in 2013 there was one resource that everyone pointed me to: TechCrunch. The people really in the know also knew to check HackerNews.

When I started working in venture in 2014, there was one resource that got added to the list: Fortune Term Sheet.

If you checked in on those 2-3 resources, you'd have a pretty good lay of the land in tech. But around that same time, two things happened.

In 2011, a16z made the claim that "software is eating the world." Increasingly, if software and technology are becoming "everything," then media about technology transitions from being niche to being universal.

In 2013, Snowden let everyone know that companies like Google, Facebook, and Microsoft were letting the NSA access user data. Then, Cambridge Analytica happened in 2018. During the dotcom, the internet had been new, exciting, and hyped up. People were excited by the prospects. But things like Cambridge Analytica went on to sully the reputation of tech.

Granted, journalism had always had a bent of skepticism. The overarching curve of distrust in institutions has been happening for decades, it isn't new to tech. Nobody trusts the government and only 16% of people have “great trust” in newspapers. But a new generation of tech companies continued to grow so large that the narrative shifted and the public's view of tech turned to one of default skepticism.

The "mainstream media" turned on tech, constantly looking for the next bad thing. Even as new platforms launched, like Axios or The Information, they oscillated between larger-than-life coverage of big tech and politics to appeal to the most people, or dabbled in startup "skepticism." Journalistic integrity made them feel inclined to rain on the hustle of the people building technology.

To the average observer, tech was exposed as a boys club determined to do the least good for the most money, regardless of the consequences.

But the people dedicating their lives to building technology weren't content to let other people write the story. First, it started as a grassroots attempt to communicate in the blogosphere. Eventually it grew to become a decentralized spin machine intent on seizing the narrative and enabling stories told for builders by builders.

Birth of The Blogosphere

The blogosphere is nothing new. It was born in either 1999 or 2002 depending on who you ask. But not too long after that it became a primary vehicle for unpacking technology. The ancient texts of tech were born in individual blogs. Scattered around the internet.

Paul Graham. Fred Wilson. Mark Suster. Bill Gurley. Pmarca. Brad Feld. Hunter Walk. Sam Altman. Tom Tunguz. Most of them started in the early 2000s (though shoutout to Bill Gurley who started writing Above The Crowd in 1996).

Great librarians, like Kevin Gee, have chronicled these and other great writings by great investors in The Archives. Study your heritage my friends.

While these greats set out to build the blogosphere in tech, the idea of individual chronicling was nothing new.

Howard Marks and Warren Buffett have been building trust through writing for decades. Marks started in, I think, 2000. Buffett is the Godfather of Investment Blogging. He's been writing since 1959, at least, first with his partnership and then through the annual letters of Berkshire Hathaway. Sixty years and counting.

A lot of people in tech are disciples of Warren Buffett's letters, though rarely in practice. I think people in tech often resonate more with the clarity of thought and ownership of narrative, despite pursuing a very different path towards generating wealth.

From personal, informal blogs there emerged another approach to narrative control: specialization. Ben Thompson started writing Stratechery in 2013. Matt Levine started writing Money Stuff in 2011. Benedict Evans started his analyst blog in 2010. Azeem Azar started writing The Exponential View in 2015. These kinds of people built reputations for being the go-to source to understand particular aspects of technology or markets. But candidly, for almost 10 years they were relatively rare.

There were also some attention grabbers like This Week in Startups and Professor Galloway that I hesitate to put in the same paragraph as the likes of Thompson, Levine, Evans, and Azar because TWIS and Galloway are nowhere near the same caliber. But they were all part of a developing ecosystem that filled in the gaps around technology.

For almost the first decade of my career, that was the state of startup media. You had some great blog posts that got passed around, some expert analysis here and there, and a mishmash of tech journalism across TechCrunch, The Information, and some of the bigger publications when they decided to dabble.

Then, things started to change.

"Business Is The New Sports"

During COVID, everyone was at home with more disposable income and nothing to do. So we looked for distractions. For some people, that was reading about tech. But for other people? That was writing about tech.

The title of this section comes from a piece by Packy McCormick who not only articulated this phenomenon, but rode it to great success.

Not necessarily entirely driven by COVID, but seemingly all around the same time, the state of startup media exploded. Packy started Not Boring in April 2020. Lenny Rachitsky started his newsletter in April 2019. Mario Gabriele started The Generalist in August 2020. Molly O'Shea started Sourcery in September 2019. Gergely Orosz started The Pragmatic Engineer in 2021.

In the background, the podcast networks had been building and building. Invest Like The Best had started in September 2016 before becoming Colossus in July 2020. Acquired started in 2015. They took longer to compound, but then they popped off arguably even harder than many of the blogs.

The memes of production were humming.

Couple this newfound capability around startup storytelling with an increasing hunger for optimism, humor, American dynamism, and stories about building as told by people in the trenches vs. in the journalist's bullpen, and what do you get? An explosion of company storytelling like we'd never seen before.

The Newfound Republic of Letters

I wasn't around for most of these, so I can't be sure. But from what I have studied, I don't think you saw this same explosion of hunger for storytelling and story-hearing in the Doctom, the heyday of Bell Labs, or the height of the industrial revolution.

The only analogue that feels appropriate is a newfound Republic of Letters — but rather than ink-dripped quills and parchment, our letters are blogs, podcasts, deep dives, Twitter threads, TikToks, YouTube videos, and more.

In the 17th and 18th century, the Republic of Letters was a "long-distance intellectual community" driven by handwritten letters across nations or even continents, with many pointing to the Republic of Letters as a key influence on the Age of Enlightenment.

From building academies to hosting salons, establishing journals and printing operations; the memes of production in a pre-internet era were handwritten ideas shared to drive inspiration. To tell stories.

One of my Quake Books is called Reinventing Knowledge: From Alexandria To The Internet. If you're interested, I'll include a summary and quotes in an appendix* at the end of the piece because I love this book. But the TLDR is that its an exceptional explanation of different periods of time that have experienced similar "Republics of Letters." From the Library to the Monastery, University, Laboratory, and beyond.

Each time, the Republic of Letters has been driven by responding to a crisis with reinvention, often by reshaping institutions and emphasizing disciplined sharing of ideas through curation, debate, validation, and transmission across generations. Consider the characteristics of these periods of time:

• Focus on status through insight over credentials

• Decentralized approach to power, emphasizing "thought leaders" over "ordained leaders"

• Distrust of legacy institutions and a thirst for meritocratic ideas-based revolution that lead to the creation of new institutions

• Commitment to producing new knowledge

The analogue to today is shocking. We have, in tech, a beautiful commitment to our own Republic of Letters . Like... isn't that crazy? That list of things has been present at every major ideological revolution and they are exactly what is happening right now.

Death of credentialism? Everywhere from the downfall of Harvard to the rise of vibe coding.

Decentralized approach to power? People on Twitter can, sometimes, have more power than a head of state.

Distrust of legacy institutions? From election denial and COVID cover-ups to the founding of The University of Austin.

Commitment to producing knowledge? Voluminous blogs, podcasts, Twitter threads, YouTube videos, open-source code, and on and on.

Consider a few examples.

Dwarkesh Patel is a 24-year old who, with no credentials or expertise, simply started interviewing smart people. Fast forward a couple years, and he's interviewing the CEOs of Stripe, Anthropic, and Microsoft. Death of credentialism? Check. Decentralized approach to power? Check. Commitment to producing new knowledge? Check, check, check.

We trust The Free Press more than a 173-year old publication like The New York Times.

Joe Rogan may have helped Donald Trump become The President of The United States.

In a Republic of Letters, we don't care who someone is, we care what they think.** We aggregate and inspire those thoughts through everything from blogs, like Mostly Metrics and Digital Native to podcasts like Age of Miracles and AI & I, to YouTube channels like Cleo Abram and MKBHD, to media platforms like TBPN, Sourcery, Newcomer, and The Free Press, to organizations like Institute For Progress, Arc Institute, the Long Now Foundation, and Astera Institute, to publishers like Stripe Press and Scribe Media, to printed publications like Arena Magazine, Asimov Press, Works in Progress Magazine, Palladium Magazine, The New Atlantis, and Colossus Review, to feature films like Story Co. and Coinbase. And on and on and on.

We are in a newfound Republic of Letters.

But as the memes of production spin, we find ourselves facing the age old conundrum of being able to separate "signal from noise." From the early days of tech illuminatis blogging deliberately in the quiet corners of the internet to today, where blogs are exploding to 1M+ subscribers and podcasts are being hosted live in sports arenas, the volume of new content can feel overwhelming.

What's more, the loudness of existing voices can drown out would-be new voices. We have created a movement of information. The question now is where do each of us exist in that movement?

I Need To Speak

Stop me if you've heard this one before. You're having a lot of interesting conversations, or you want an excuse to talk to some really smart people, or you and your friends always surprise yourselves with the depths of your insight. But you're not much of a writer and you don't have time to edit YouTube videos. So what do you do? You start a podcast.

In tech, it feels like the volume of podcasts has exploded. A few years ago folks listened to Invest Like The Best and 20VC, maybe even dabbled in Stratechery's podcast.

Fast forward to today.

Podcasts, Podcasts Everywhere

You have the hits that have gotten built up over time, from Pirate Wires to Sourcery, No Priors, the MAD Podcast, or How I Write.

You've also seen the big successful blogs launch podcasts from Lenny's Podcast to Not Boring Radio and The Generalist Podcast

And it feels like you've got new ones launched every day. Chris Paik at Pace Capital launched one, Imran Khan at Proem Asset Management launched one, ZFellows launched one, Bill Gurley and Brad Gerstner started the BG2 Pod, Jack Altman launched Uncapped, Michael Mignano launched Generative Now at Lightspeed, even yours truly, at Contrary, has both Research Radio and Tech Today.

You also have the podcast networks, like Colossus expanding from Invest Like The Best to include Business Breakdowns, Making Media, and a bunch of others, or the launch of Turpentine that provided podcasts-as-a-service. Even Lenny got into the podcast network game with the recent launch of another podcast in his umbrella, How I AI.

Then you have big venture firms that are trying their hand at building podcast networks. Redpoint started out with The Logan Bartlett Show before expanding into Unsupervised Learning, Termsheet Teardown, Vital Signs, and more. Sequoia got into the game with Crucible Moments and Training Data. a16z took the build AND buy approach. Not only has the a16z podcast been popular for years, they added to that by acquiring Turpentine as their podcast network.

Turpentine is far from a16z's first foray into the world of media. Beyond Marc Andreessen's famous Pmarca blog, a16z launched Future.com back in 2021. But just over a year later, a16z turned it off. It isn’t media for the sake of media that resonated. It’s about media with something worth saying.

Despite the feeling that the tech world is drowning in podcasts, the counterintuitive reality is that the volume of new podcasts being launched has actually been decreasing since a massive COVID-boom.

Source: Twitter

So its not that, universally, the volume of podcasts is continuing to increase. It's that people in tech, in particular, have something to say.

Writing, Too

You also have Substack as a driving force behind so many people building their own blogs — Tanay Jaipuria, Janelle Teng, Nnamdi Iregbulem, Brett Bivens, Shomik Ghosh, Jamin Ball; even I fit in this bucket with Investing 101. And then pre-Substack you've got a lot of people that have built effective blogs for communicating their perspective, from Amjad Masad to Kevin Kelly, Tyler Cowen, Noah Smith, or Matthew Ball.

If you feel overwhelmed by the volume of the content, or even feel the itch that I've forgotten the name of a great media recommendation, then you're starting to get my point. What happens when the Republic of Letters is so supercharged by the internet that it becomes overwhelming? That isn't automatically a bad thing. It fosters an even greater competition of ideas.

In my perspective, the volume of content being created in tech is an amalgamation of forces.

First, organizations are seeking to, increasingly, "go direct" as Lulu Cheng Meservey would say. Control the narrative and be your own propaganda machine. As the world becomes louder, getting your message across is a skill, not a light switch. So you need to practice.

Second, we have an intrinsic belief in the message. Whether its technology, optimism, progress, or pointing out dangerous counter-narratives, we want to proselytize our beliefs, and media gives us the tools to do so.

But finally, on a personal level, I think those of us that are trying to communicate through content are often attempting to make ourselves not just legible, but hyperlegible.

Pursuing Hyperlegibility

Communicating With Your 'Ride or Die'

Apparently, I think in Packy Titles today because this section is named after another piece that he wrote. Packy explains hyperlegibility this way:

"Information that was once hard to find is now hard to avoid... Hyperlegibility emerges with game theoretical certainty from each of our desire to win whatever game it is you’re playing. In order for the right people and projects to find you, you must make yourself legible to them. To stand out in a sea of people making themselves legible, you must make yourself Hyperlegible: so easy to read and understand you rise to the top."

In other words, it isn't enough to speak so clearly that people understand, but rather to be so intensely shaped when it comes to your message that "no one can misunderstand."

Sometimes if you're TOO legible you can either smack of populism or become unappealingly watered down. If your message appeals to everyone then you haven't said anything worth saying.

In the words of Palmer Luckey, "you need to care about that 1% of the world that is going to be your ride or die.”

The best ideas, often, do not immediately succeed in the court of public opinion. But to people those ideas impact directly, they see the solution inside. Not everyone likes democracy, but it was probably a pretty good idea. Not everyone likes the internet, but it was probably a good idea.

At the end of the day, becoming hyperlegible is about targeted mass communication. We may not even know who we want to be listening, but we'll know them when we see them.

For The Vibes

There is a core truth about writing on the internet (or blogging or podcasting or whatever). The core first principle of the blogosphere is that it is an act of sending your vibes out into the universe and inviting serendipity. That's been true since people were relying on RSS feeds when Blogger launched in 1999.

But what changed during COVID was the realization that (1) technology ate everything, and (2) that feast included most of the ways that we interact. In a way that wasn't true even in 2019, I now have dramatically more online friends than I have IRL friends.

Everyone, from Fortune 500 CEOs to politicians to founders to VCs to academics have come to realize that a larger and larger bulk of how they live their lives, communicate their message, and do their work will happen online.

As a result, more people are coming to realize that we've stepped into our first meaningfully encompassing Metaverse. But it wasn't a VR headset. It was the Vibe-o-sphere.

And if you’re going to succeed in the modern age, you need to understand how to build in the vibe-o-sphere.

Building In The Vibe-o-Sphere

Too Much Noise

For most people the volume of interactions in the vibe-o-sphere is the biggest argument against participating. I was the same way. Before I started this blog, I was convinced that I would just be shouting into the void. I wasn't consuming all the content that was being created, why should I add to the noise?

But the first thing you realize about creating anything once you start doing it consistently, be it writing, art, poetry, music, videos, or music, is that what it does to you is much more important than what it does to anyone else. Paraphrasing a point that Dwarkesh Patel made about the benefit of doing his podcast:

The real flywheel of the podcast is not compounding audience growth. The real flywheel of any creative endeavor is compounding the creator.

So write, speak, create. Because even if no one is listening, you will evolve.

Somebody Is Already Speaking

The volume of people participating in the New Republic of Letters can feel intimidating. How could you possibly add something new to the conversation? One great Charlie Munger quote comes to mind that encompasses most of the successful new publications:

“Take a simple idea and take it seriously.”

When I launched Contrary Research, it was built off a simple premise: Build the best starting place to understand any private tech company. That has guided our work ever since, as we've grown to 100K+ subscribers and 500+ reports.

When my partner, Eric, launched Tech Today, it was with the belief that people wanted a short, 10 minute overview of an important topic each day to help them feel informed.

There are other people who I have massive respect for how they've carved out their niche in a broad universe.

One exceptional example is David Senra with Founders Podcast. He took a simple idea; the wisdom of ages is locked in the pages of the biographies of founders. So, eight years ago, he set out to unpack them.

Another example. In 2022, I came across Arny Trezzi. He was purely focused on writing and researching about Palantir and becoming an expert on it. In his words, he explained why he focused exclusively on Palantir:

"I believe it will be a 'Big Tech.' There are already signs in the numbers, but it is still widely misunderstood by the financial industry. Being controversial makes many people just stop at the surface. [That] is where asymmetries lie."

Since I met Arny, Palantir has become a 10-bagger.

Other people, like Whole Mars Catalog, have done that with Tesla.

Lots of companies would LOVE a storyteller. You don't even have to wait until the company is public. Even if they don't hire you, become a journalist for a company you believe in. Or better yet, get hired and become an embedded journalist. This is happening more and more.

Source: Twitter

Whatever simple idea resonates with you, simply take it seriously. And remember the lesson from MrBeast that success in creating anything is often just in the act of creating. He published a YouTube video once every 11 days for 10 years. That's how compounding works.

Where Do I Start?

For a lot of people, writing in public can be too intimidating. The Republic of Letters doesn’t have to be played out exclusively in nailing your thesis to the church door. In bygone eras, it happened largely in private correspondence. The same can be true today. If you don't want to write in public, write in private. But it has to be for someone.

The best avenue for that? Group chats. As Katherine Boyle recently wrote:

"Group chats are a relic of another era where friends could spar without worry. Where you could debate and work through complex ideas in a way that allows every corner of the argument to emerge. The good faith debate is healthy, and it’s the 21st century model of this."

I have a group chat I'm a part of where one guy is 75% of the content, but having access to his aggregation of news, his thoughts and commentary, I would pay $20 a month for it. Be that guy.

[Creators] Don't Make Money

In October 2015, Benedict Evans described a16z as "a media company that monetizes through venture capital." Recently, Paul Smalera wrote a piece called "The Next Great VC Firm Will Be Built Like a Media Company From Day One."

TBPN has gleefully embraced ads and sponsors.

Media companies die on the vine because they can't sell ads or are addicted to subscribers paying for their whole service.

Find a way to make your storytelling viable for you. What are your north star KPIs? They can be different for everyone, but have them.

This Is Personal

I started writing this week as a few quick observations to accompany my conversation with Evan Armstrong, but it started to pour out of me. I realized that my journey into startups was born because I loved stories.

I remember one of the first ever "startup stories" I got hooked on was the podcast, StartUp in March 2014. It was literally a guy starting a podcasting company doing a podcast about the process of starting his podcasting company. Very meta. But I loved it. I heard him talking about pitching Chris Sacca and it resonated. I heard the story of struggling to negotiate with a co-founder and it resonated. The story hooked me.

Since then, everything I've loved about startups has revolved around storytelling. I started listening to Acquired in 2015 (before it was cool). I started writing as soon as I had the chance. When I got to Contrary, the first thing I wanted to do was build Contrary Research.

So this story of the evolution of media in startups isn't just a neat observation. For me, it's personal.

The New Republic of Letters is everything I've ever wanted to be a part of.

And now I am. And I'm grateful.

But the work has only just begun.

There are many stories left to be told, and many stories yet to be written.

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Appendix

*I promised a summary of Reinventing Knowledge because it's SO interesting to me. Here it is with the help of ChatGPT.

Reinventing Knowledge — Core Thesis

Reinventing Knowledge argues that Western civilization advances when it invents institutions that can both safeguard existing learning and channel new ideas into society.

Across 2,500 years, six such institutions arose in sequence, each forged during a period of upheaval that exposed the limits of the previous one:

Recurring Patterns

1. Crisis → Reinvention: Sweeping social shocks—not lone geniuses—drive each institutional shift. Dissatisfied scholars repurpose emerging technologies (papyrus, parchment, print, the web) into the next interface between ideas and society.

2. Institution > Individual: Brilliant insights endure only when an institution turns them into common practice. A mediocre idea with strong institutional backing beats a great idea orphaned from support.

3. Costly Commitment Signals: From monastic vows to tenure, each institution demands discipline that filters noise, sustains focus, and signals credibility to outsiders.

4. Information ≠ Knowledge: Cheap, ubiquitous data alone never guarantees wisdom. What matters is organization: curation, debate, validation, and transmission across generations.

5. Today’s Tension: The internet—born in Cold-War labs yet fueled by counter-culture ideals—revives the ancient dream of a universal library and the collaborative spirit of the Republic of Letters. But by drowning experts in undifferentiated “content,” it also threatens the very gate-keeping mechanisms that make knowledge reliable.

Why This Matters for Startup Media

Modern tech newsletters, Substacks, Discords, and founder blogs echo the Republic of Letters more than the research university:

• Decentralized & borderless: Influence flows through networks, not campuses.

• Status earned by insight & civility: a persuasive post or thoughtful thread confers membership.

• Instrumental in periods of institutional mistrust: As legacy academia and traditional journalism struggle, technologists create parallel forums for debate and peer review.

• Focus on producing new knowledge: Playbooks, open-source code, demo videos—rather than merely curating the old.

Ten Quotes to Illustrate the “New Republic of Letters”

1. “The Republic of Letters can be defined as an international community of learning stitched together initially by handwritten letters in the mail and later by printed books and journals.”

2. “It was an institution perfectly adapted to disruptive change of unprecedented proportions… founding its legitimacy on the production of new knowledge.”

3. “The Republic of Letters, like any republic, was governed by its citizens… there were no certificates, no degrees, no formal credentials of any kind: anyone who obeyed the rules of civil conduct could join.”

4. “The republic transcended not only frontiers but generations. It was explicitly seen as a collaborative venture bringing scholars together… across time.”

5. “Communication in the Republic of Letters was indeed rarely face-to-face, and participants might correspond for decades without ever meeting each other.”

6. “Letter writing stressed a very different set of virtues… civility, friendship, generosity, benevolence, and especially tolerance.”

7. “Erasmus… became Europe’s first celebrity intellectual by crafting his public image in print, in particular by carefully editing and publishing his own letters.”

8. “As we have seen, the letter, the book, and the museum together reformed many practices of the university… The Republic of Letters acted as an umbrella institution for them all.”

9. “The ‘cyberculture’ of the early Internet pioneers bears remarkable similarities to the early modern Republic of Letters as it broke free from medieval universities politicized by religion.”

10. “Promoters of the vaunted ‘information age’ often forget that knowledge has always been about connecting people, not collecting information.”

11. These lines capture how a dispersed, self-selected network can out-innovate older hierarchies—a dynamic now re-emerging in the startup media ecosystem.

**A side note on when its not necessarily the quality of ideas that wins.

Sometimes there are movements than thrive even if they don't represent the best ideas. For example, I think Donald Trump's continued success is a symptom of the rebellion to the rot of the status quo. I wouldn't go as far as to say Trump wins on the merits of his ideas.

And maybe this is a tangent that is worth exploring some other time, but in some ways that could be a result of the general public's reduced ideological literacy. When Common Sense was published in January 1776, it had a viral impact. I'm not sure the same kind of idea that held the same impact for us today would achieve the same virality. But I digress.

***A side note on the volume and loudness of ideas.

The overwhelming volume of ideas could also be a symptom of "personal truth," where everyone thinks their ideas are true vs. the meritocratic Core Truth. But I prefer to believe that, in the end, the quality of ideas will win out. Despite the way we consume our media and the fact that we have become so programmable, ultimately the best ideas can win out.

Things like Communism were a bad ideas and, despite a LOT of support, even in the US, it eventually died out (sort of). The holocaust might have had a pretty solid PR team and propaganda machine but the light of history eventually put that idea in its place (sort of). From slavery to horse-drawn carriages, eventually almost every idea gives way to better ideas. That may not always be true, but its the optimistic view of the world I prefer to espouse.

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