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How He Started the Paid Newsletter Trend — Ben Thompson

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David Perell1:33:02Open on YouTube
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The bottom line

A solo writer can build a paid business by publishing every day from one evolving framework of how the world works. The internet's zero marginal costs let a loyal niche pay well, but only if the writer keeps producing.

Key takeaways

One framework turns daily news into daily writing
Most news passes straight through to a conclusion; the big articles come from the places where the model breaks.
  • The internet rewards a few huge platforms and countless small niche players. 1:10:04
    • Platforms that control discovery attract users, then supply, then more users. That virtuous cycle leaves very few, very large winners.
    • Traditional media has cost structures built for printing presses and delivery trucks, so it can't shrink to serve a niche. Thompson has subscribers in over 100 countries.
  • One evolving framework of the world lets him write every day. 13:55
    • He feeds each piece of news into the "machine" and a conclusion comes out: if A happened, then B, then C.
    • Full articles come from a void in the machine, where something doesn't make sense. He also quotes his own older pieces, because Stratechery is a journal of his understanding.
  • Readers pay for regular delivery, so volume matters more than any single piece. 52:11
    • He charges $15 a month for a steady flow of updates and an interview. Dylan Patel charges $500 a year because he sells a rare, high-value scoop.
    • About 170 to 200 public pieces a year add up to the equivalent of 50 or 60 books in a decade.
  • Free stories and a consistent look win the second visit that turns a reader into a subscriber. 1:07:52
    • His best articles tell a story. The Disney Charter standoff piece opened with the first commercial satellite launch.
    • The custom font, orange color and hand-drawn sketches were chosen so a returning visitor recognizes the site.
  • Writing about a niche you care about keeps the daily grind sustainable. 52:31
    • His one near burnout came in 2019 and 2020 from writing about antitrust and Congressional hearings. Hard work was not the cause. The topic was soul-sucking to him.
    • Neil Cybart writes only about Apple and owns that pond. Thompson's advice is to make your own pond rather than fight the other fish.

The most important article you write is the second article someone reads.

Ben Thompson

Chapter summaries

0:00 Introduction

Thompson's results come from daily grinding inside a clear model of how the internet works.

  • The conversation is a 101 on writing online. 0:45
    • It covers how often to write, what the business model is and how the internet works.
    • Thompson's frameworks explain where the world is going, not only where it is now.
    • Thompson says his success would have been hard without the day in, day out grind.
    • He calls himself a big believer in hacks, which sets up the deadline talk later.

1:20 Day in the life of Ben Thompson

Free articles are harder than paid updates
Free articlesPaid updates
WhereFront page, freeBehind the paywall
ReaderUnknown, maybe first-timeKnown subscribers
ReachCan go viral, ~1MSubscriber base
Must doExplain more, open with a hookDeliver steady analysis
DifficultyHarderEasier
Articles have to win over strangers who may be reading Stratechery for the first time, while updates serve readers who already pay.

Free articles and paid updates are two different jobs with different readers, and articles are harder.

  • Articles face unknown readers, while updates face known subscribers. 1:36
    • Articles sit free on the front page. Updates sit behind the paywall.
    • An article can go viral and reach a million people who may never have read Stratechery.
    • So an article must explain more and still open with a hook.
    • Many imitators he followed on Twitter had equally good insights and mostly flamed out.
    • His edge over them was volume and storytelling, not sharper insight.

3:00 The Importance of Storytelling in Writing

A story-shaped article costs hours, and most of that goes into finding the opening.

  • Once the first few paragraphs work, the rest follows. 4:04
    • Good pieces are analysis with a beginning, a path and a resolution.
    • Some articles take hours, mostly to work out how to get in.
    • Some pieces with strong analysis have a weak opening and still ship, because they had to be published.
    • The ideal reader is led in by a story they have never heard, then lands in arcane business details such as carriage disputes.
    • The less interesting articles are usually the ones where the opening never came.

4:30 The Role of Flow State

Writing works like programming, so it needs an uninterrupted flow state.

  • Thompson holds the whole structure in his head while he types. 4:50
    • A programmer keeps the whole application in mind, and writing is turning that into text.
    • Looking things up and typing must not break the structure he is holding.
    • When locked in late, he arrived at dinner catatonic and shoved food in his mouth before going back.
    • His wife's verdict was that he needed an office.

5:30 Balancing Work and Family Life

Protecting flow meant working away from the family while the kids were young.

  • A separate workplace matched his separate mental state. 5:57
    • He rented another place because the kids saw dad home and wanted to talk.
    • Work is his job, not their responsibility.
    • He works at home again now that the kids are older.
    • Getting started is hard every day. After that it moves quickly.
    • It is a million times harder for articles without a hook up front, since they are broadly visible.

6:40 Finding hooks, audiences, and common threads

Updates are easier because the opening and the audience are known, and the best ones tie back to a thread.

  • Updates start from a news excerpt and a paying audience. 7:12
    • He opens with the "nut" of a Wall Street Journal or Bloomberg story and launches from it.
    • Subscribers chose to be there, so he assumes knowledge and skips introductions.
    • Earnings season is a clear example, since he knows exactly what he will write about.
  • A common thread gives the reader a payoff. 7:55
    • Strong updates plant something in part one and tie it up in parts two and three.
    • A Google capex point he had held back fit neatly into the Microsoft earnings piece.
    • Readers should finish feeling the 10 minutes were well spent.
    • Without that aha, boredom builds up, though readers don't consciously notice it.

9:45 Daily Deadlines and Productivity Hacks

Thompson is productive because a deadline every day forces him to be.

  • He sees himself as a procrastinator and uses deadlines as the hack. 10:04
    • He sets alarms for everything, which drives his daughter up the wall.
    • As a serial thinker, he does no side conversations while working.
    • His college thesis was written in one 36-hour run on caffeine and a few beers. He handed it to his adviser at a graduation party.
    • He has never written a book and fears open-ended time. A blog that covers events in real time suits him.
    • After a weak piece he sleeps badly, and he says the day that stops is the day to quit.
    • There is no option to check out early on a bad day.

13:55 Developing a Framework for Writing

Hyperscalers span AI for themselves to AI for others
Thompson's next article starts by asking how capex risk changes as you move along this line.

Because he thinks about his topics all the time, writing is mostly writing down conclusions he already holds.

  • The sit-down-and-research method could not produce thousands of pieces. 13:21
    • When the news is straightforward, he only writes down the steps.
    • When it is surprising, it signals a missing piece, such as another announcement that must follow.
    • A piece needs a news trigger. Pure theory usually doesn't resonate.
    • An article on the risk of the hyperscalers is forming. Meta uses AI for its own product and AWS serves third parties, with Microsoft and Google in the middle.
    • He asks how risk lines up along that spectrum.

16:30 The Impact of Regular Writing Everyday

Each article adds a small custom block to standard parts
Like a chip built from TSMC's cell library, most of each piece reuses earlier work, so only the new part needs writing.

Daily writing makes Stratechery a living journal, and the writing itself forces Thompson to find out what he thinks.

  • The daily format rewards regular readers. 17:03
    • Insights are anchored in the time and place they came from, so an anthology would be hard.
    • A book would lock in views he may no longer hold.
    • A book on aggregation theory would have to be timeless. His format is not.
  • Writing forces his thinking into final form. 17:52
    • Most essays form in his head. Others only become clear by writing.
    • Like Bezos on bullet slides, the gaps between ideas have to be filled in.
    • Writing makes him a better podcaster, because every claim must be correct and structured.
    • He wants to equip readers, not always be right. A CEO with more information can use his structure and reach a different conclusion.
  • Each article adds a small piece to a standing set of concepts. 21:15
    • TSMC offers a library of standard chip blocks, and a customer adds the last 5% of special sauce. His writing works the same way.
    • The one-line concept summaries on the site are written at the last second.
    • He re-quoted an old piece on Facebook's TikTok shift because he could not say it better.
    • He is not writing a thousand new short stories a day, but evolving one understanding.

24:55 Editing and Finalizing Articles

Tight thinking up front replaces heavy editing, and a last-minute deadline does the rest.

  • Little editing is needed because the thinking behind each piece is already tight. 25:27
    • Some pieces, around 5,000 words, could be trimmed. He accepts that as the trade-off of his model.
    • He rarely rewrites because he has thought about the subject for about 10 years.
    • His edits are mostly typos and repeated words, which "drive me up the wall".
    • He compares his memory to a large L1 cache: the whole structure is in his head and he retrieves it fast.
  • Reading each article aloud before publishing almost removed his typos. 26:34
    • He started because every article is also a podcast.
    • Stumbling over a sentence shows where it reads badly.
    • His typo rate fell to about one a month, from many more.
    • He writes about how he talks: long answers that still tie back to one thread.
  • Deadline panic, not calm routine, drives his writing. 28:56
    • He squeezed his week into three writing days plus one interview day.
    • Mornings go to admin, interviews and US sports. He procrastinates after lunch, and the writing happens in the late afternoon.
    • He says he is not proud of it and wishes he were more disciplined.
    • His student paper editorials at the Daily Herald ran on the same last-minute rhythm, and he loved it.
  • Writers should aim at topics where they have earned authority. 29:59
    • As a student editor he refused national issues. Nobody cares what a student paper says about them.
    • Student government does care, so the paper wrote daily editorials on campus issues.
    • The paper judged that it met four of its five objectives.
    • He avoids partisan picks today because he wants influence on technology, where he is credible.

32:25 The Impact of Reading on Writing

Targeted reading and fast, public corrections make a direct writing style credible.

  • He reads on purpose, when a piece needs it, and not for leisure. 32:44
    • On some mornings he reads a whole book and then leans on it heavily in that day's article.
    • Many of his best pieces are historical, since a company's culture traces back to its founding.
    • One day of intense research on how GPUs work paid off years later when AI and Nvidia took over.
    • His best compliment is a reader outside the field saying you really got that.
  • He states his view directly and corrects mistakes at once. 35:28
    • John Gruber's rule: the best way to always be right is to correct yourself immediately when you are wrong.
    • He also walks readers through which link in his chain was mistaken.
    • His style is "because of B, because of C". Hedging makes writing dull.
    • An analyst is not a stenographer. Companies supply the PowerPoints, and his value is what sits in the middle.
  • The first five minutes of a keynote reveal how a company wants to be seen. 38:11
    • The frame a company picks says more than its products.
    • He guards against confirmation bias, since he is always plugging news into a worldview he already holds.
    • He accepts overcorrecting and getting things wrong as the price of that guard.
    • He still checks whether the real numbers and specifications match the narrative.

39:45 "What Clay Christensen Got Wrong"

Stratechery began where a respected framework failed to explain technology and Apple.

  • Business school ignored what makes technology different. 42:07
    • At 27, after teaching English in Taiwan, he got an MBA. His wife had told him to work in tech.
    • The first-day case list had no technology companies. His professor said the principles apply to all industries.
    • He disagreed. Zero marginal cost means one more visitor to google.com costs nothing.
    • Zero transaction cost lets Google serve 7 billion people without a person involved. Putting a zero into an equation changes the whole result.
  • Thinking an expert is wrong can be the seed of a piece. 44:25
    • He says writing your own site takes some narcissism and delusions of grandeur.
    • He began with about 380 Twitter followers and no favors from anyone.
    • Social media then rewarded sharing interesting links. Today links are suppressed.
    • He calls it not obviously good career advice, but it worked for him.
  • Christensen's disruption thesis fails on Apple because of a historical error. 45:48
    • Apple broke the theory's rules, yet people predicted doom for the iPhone as for the Mac.
    • DOS and the PC market existed before the Mac shipped. The iPhone came first and Android later, the reverse of the popular story.
    • He calls Christensen the biggest influence on him, who still got that fact wrong.
    • He says to go back and check the myth against what happened, or whole swaths of analysis can fail.

47:30 The Importance of Knowing Your Stuff

Background knowledge comes first, and then a thick skin lets you trust your own view.

  • Once you know the facts, you have to trust your view and take the pushback. 47:35
    • He rates himself 0% agreeable and says successful people online are probably highly disagreeable.
    • He is not immune. One piece spread to an unfamiliar crowd, and the attacks cost him sleep.
    • People were not meant to receive this much feedback, and most just want to get along.
    • Perell's prompts: where does an expert's theory fail to explain something, and where does your worldview not line up? Posts that admit a mistake are the most instructive.

49:30 The Value of Regular Content Production

Showing up every day builds a better body of work, a more committed base of readers and the attention of powerful people.

  • Volume beats waiting for quality. 54:03
    • Readers say just write good stuff, but what they actually reward is the steady flow.
    • With no choice but to write, the process produces more compelling work, even if some pieces could use another round of editing.
    • He covers media because it is the canary in the coal mine. Tech, media and telecom are all zero marginal cost industries.
    • His media analysis is wrong more often than his tech analysis. Hollywood is a city of big personalities, and people do dumb things for prestige.
  • Annual subscribers who started monthly are the best cohort. 55:10
    • Most subscribers are now annual, which frees him. One bad update can be made up over a year.
    • The best group subscribed monthly, turned off auto renew, then switched to annual in the first month. Daily delivery had made it a habit.
    • Churn is very low, and lapsed readers still get the free articles.
    • He doesn't want to understand his business too much. As long as the number isn't going down, things are good.
  • CEOs read him because he has no reason to flatter them. 58:21
    • Everyone around a CEO has some incentive to say what they want to hear. He only reads their reports and listens to their earnings calls.
    • Pushback comes from marketing staff and senior VPs. He has never had it from a CEO.
    • A payment processor once told him about three double-charged subscribers. One was the CEO of a top-five Fortune 500 company. He tries not to know who subscribes.
    • He used to work at Microsoft. He likely has more impact on it now than he would have had after 10 years of promotions and internal fights.

1:00:45 Business Models and Media Companies

A one-person media company can compete with giants because the internet makes the back end free and leaves only the daily writing as cost.

  • A single writer competes with the largest media companies on an equal plane. 1:01:38
    • For readers, time is time. Every minute on his site is a minute not spent on the New York Times.
    • For four or five years he was one person, doing his own taxes, accounting and email. His only costs were credit card fees.
    • Media is scalable on the back end and not on the front end. Writing every day is the real cost, which makes media a poor investment and an opening for people who can keep producing.
    • Stripe started in 2009 and launched its product in 2011. He launched in 2013, when easy credit card subscriptions had just become possible.
  • A small audience that pays well is a good outcome, and a new writer needs volume to get one. 1:06:26
    • A thousand weekly listeners would have sounded remarkable in the 1990s. Social media shows only the biggest successes, so people misjudge their own.
    • A writer needs a way to win customers and a product to sell. A mix of free and paid writing does both, and one article a week can't.
    • At $100 a year, a thousand subscribers bring in $100,000, the classic "true fans" math.
    • Social links used to spread his work through word of mouth, and that is much harder now. A new podcast of his reached five-figure listeners overnight by borrowing the audience he had already built.

1:10:00 How the Internet Works (Google, Facebook)

Online media rewards giants and niches, squeezing the middle
The pattern started in print and is spreading to other industries where content costs nothing to copy.

Abundance makes curation the scarce thing, so a few giants and many niches thrive while the middle gets squeezed.

  • Winners sit at both ends of the market and the middle is squeezed. 1:10:14
    • In the analog world, scarcity meant distribution mattered. On the internet everything is free, so finding the good stuff matters.
    • His thesis that the big five were undervalued proved right. They outperformed venture capital, which he says is why he has so many loyal subscribers.
    • He calls this the barbell effect or the smile curve. It began with print and is spreading through other industries.
    • The choice is to serve a niche or to serve everyone at zero marginal cost. Everyone in the middle is screwed.
  • The niche market is far bigger than most people assume. 1:13:44
    • The addressable market is billions of people, so capturing a small share is enough.
    • Well-known VCs told him the paid version of Stratechery wouldn't work. People paid to judge the internet's scale misjudged it.
    • People feel subscription fatigue because they are too interested in too many things. They forget that others have different interests.
    • People will pay for the most arcane niche. Substack and YouTube creators show there is no cap.
  • Huge volume means the good stuff still adds up. 1:15:57
    • Most TikTok videos are trash. If even 0.001% are great, the absolute number of great ones is still large.
    • Curation used to happen before publication and now happens after it, through search and algorithms.
    • Platforms are helped by gargantuan amounts of junk. It means a lot is being created, so a lot of good work exists too.
    • Search is a poor way to judge the internet, because it can surface garbage. What gets shared tends to be good.
  • A strong conclusion ties back to the introduction. 1:18:07
    • The Christensen piece opens by saying he got something wrong and closes by saying what. The ending pulls that thread tight.
    • He copies the introduction to the bottom of the draft to keep it in view. If the two don't connect, he adds guideposts earlier in the essay.
    • Sometimes the piece goes elsewhere and he scraps the introduction.
    • A good conclusion can mean going further out on a branch than he would like.
    • One 6,500-word piece on European regulators ran long because of an aside about the European internet. He kept it at 3 a.m. because he loved it.
  • A writer's schedule problems are never the reader's problem. 1:23:05
    • He sells a product. Readers signed up for an email every day, and his own busyness is his problem.
    • A reason to pay is not charity or helping the writer be popular. It is that they want to read what he wrote.
    • Many writers are too hesitant and not disagreeable enough to tell customers they must pay to read.
    • In summer he wakes at 3 a.m. in Taiwan to write and his updates run long. He skips interviews in July and early August and publishes three days a week.

1:24:30 The Challenges and Rewards of Niche Content

Online, a writer wins by owning a small topic and by producing steadily, not by taking on the biggest one.

  • Writing about the big tech companies means competing with everyone online. 1:24:46
    • Geography used to protect local columnists. Now readers pick Bill Simmons over the local sports writer.
    • Thompson says he gets paid for what millions do free on Twitter.
    • Casey Newton covers social networks as a whole and has done well.
    • Thompson thinks someone should cover Amazon daily, and someone Google.
  • Ideas keep coming as long as you keep producing. 1:26:53
    • Starting is easy. A first album holds songs curated for years.
    • Great bands are the ones with a great second album.
    • Daily writing keeps his idea process always running.
    • Creativity is not a well you draw down. It replenishes.

1:28:27 Writing Example (Winston Churchill)

Repeat interchangeable build-ups, then lock the climax last
The 'fluff' builds suspense; cutting it to eight words would keep the meaning and lose the memory.

Churchill's 1940 speech works because repeated build-up phrases lead to one climax.

  • Repetition builds to a single closing line. 1:29:14
    • He says "fight" four times and names five places.
    • The order of the places is immaterial. Only we shall never surrender must come last.
    • He spent about an hour of prep for every minute he spoke.
    • Speech phrases are interchangeable, so you could move the first to the seventh spot.
  • The "fluff" is what makes the line memorable. 1:31:58
    • Build-up phrases raise suspense until interest would fade.
    • An engaged audience can take more of them.
    • Eight words could carry the same meaning, but nobody would remember them.
    • He used 31 words, and people still discuss them almost a century later.

In the growth library

Ben Thompson, founder and writer of Stratechery, the original paid tech newsletter. Ben Thompson explains how a daily deadline, huge volume and stories with a beginning and an ending built a paid newsletter that earns millions. The technique worth hearing is his habit of feeding each day's news into a standing model of how the world works, so he can write every day without starting from scratch.

Lessons that draw on this:

More from How I Write · The whole library, and ask it anything

Transcript2548 lines
Introduction 0:00
0:00

the most important article you write is the second article someone reads and I do think that volume or quantity is underrated so that's like 50 or 60 books worth of writing over the last decade that is an insane amount of volume it would be hard to have the degree of success that I've had if it weren't for the just day in day out sort of grinding should we do the day in the life Grand reveal now so I have a a framework an overall view of the world and how it works I'm a big believer in hacks and life in general so the most important thing for succe on the Internet is Ben Thompson is like the OG of subscription newsletters he makes millions of dollars a year from his writing if you're thinking about hey how often should I write what is my business model going to be what is online writing all about and how does the internet work well this podcast is like a 101 classic than that and I got to say Ben is a real

1:02

Visionary his ideas his way of thinking about the world as Frameworks they're going to give you a sense for not just how the world exists now but where the world is going and it's going to help you to think about how to thrive as a Creator over the coming decades you got to walk me through a day in the life

Day in the life of Ben Thompson 1:20
1:20

because presumably you're waking up you're thinking what am I going to say today and then by the end of your day you have an article shipped yeah I mean I think one of the interesting questions that I will get a lot is how long does it take you to write an article or write an update well first off that distinction is important so I write two kinds of pieces I write what I call an article which goes on the front page of cheery that's free for everyone to read and then I write updates which are behind the pay wall and they generally have different formats and they're written for different audiences I think the articles are more challenging for a couple of reasons number one I have no idea who's reading them and what base knowledge they have and those they can go viral they can be read by a million people and they might be reading strory for the first time or they might not know that much about technology and so

2:10

my Approach that shifted over time as you know the relative Bas my readers changes but like you have to explain more things on one hand and on the other hand uh it needs to have a hook it needs to be interesting but when I started there were you know a number of people that sort of like imitated you know or wanted to do same sort of thing and I thought they were all very smart they had good insights there people who i' been following them on Twitter I'd been reading their blogs or whatever and they had good insights about technology and the vast majority of them uh kind of flamed out and never really got popular and I'm like well they have good insights and the key thing that I sort of realized is the difference between my writing and their writing you know let's assume the insights were equal number one I had a lot more volume we should definitely get to volume because I think that's actually really important but also my

The Importance of Storytelling in Writing 3:00
3:03

best pieces told a story and people love stories and they were pieces that were analysis but they had a beginning they had a they had a path and they had sort of a resolution and conclusion of like what what it came to what's an example of that from one of your pieces I was talking about the Disney Charter thing last year where there's that big sort of standoff and I opened with the story of the first commercial satellite and the rocket launch and all that sort of thing to me that was a great example of what what is a Killer article for shery where it's like you're walked in like this is really interesting I've never heard this story before and then suddenly you're like into Arcane sort of business details about about about carage disputes and so that that was I think been a different shate for shary throughout is to the extent shary is really sort of killing it I am delivering articles that are not just

3:55

sort of good analysis but are good stories and that are interesting and compelling to read now that takes a lot of work so the answer of how long do you spend well some these articles it's hours and a lot of it is literally just figuring out the opening like once I can get through the first few paragraphs I know what I want to say but like how do you actually get into it and sort of make it interesting and some of the less interesting articles which I think have very good analysis they have sort of a weak opening whatever I see you know just because I I couldn't I couldn't get it but I needed to publish it so tell me this is the open about you for the

The Role of Flow State 4:30
4:30

writer like you need to find your flow and it's almost like going down a ski slope it's like once you find it you're good or is it for the reader that you need to actually hook the reader in or well so there there's a few aspects to that so number one when I'm writing it is absolutely about Flow State for sure so you know the I actually think about the way I write as being very similar to a way a programmer is coding you have the entire structure of the application what you're working on in your head so you know all the pieces and how they work together and the act of programming is is substantiating what is in your head right realizing it that's right and so the reason why flow state is really important in sort of getting locked in is because you need to be holding that in your head while you're actually typing stuff sort of on you know on your computer and looking stuff up and doing whatever and so you know it it took a

5:25

few years of communication and understanding and frankly realizing I need to work in a different place from

Balancing Work and Family Life 5:30
5:31

my family for for to really internalize with my wife which is like look no when I'm locked in I like and she would get annoying I come like you know be find me working late I'd come to dinner and I'd just be like catatonic and I'm just like shoving food in my mouth and then going back and you're like I need an office she's like you need an office get out of here um so I do work back at home now in part because my kids are older and they're doing their own thing and stuff like that but for a while especially my kids were young uh definitely reached a point where I no I need to actually rent a different place and I need to be somewhere else just because it's at the end of the day it's my job it's not necessarily their responsibility they feel like dad's around they can talk to him and so that was sort of an imposition of of even though technically I can work from anywhere you know there is an aspect of I need to I am in a

6:19

different place I'm in a different place mentally but it's still sort of a different place and that needed to be match with being in a different place sort of physically getting in that state is for sure hard and that's for every day that's hard so a huge part of once I actually get started with the writing then it happens pretty quickly but actually getting started is hard and it's a million times harder with the Articles because if I don't have that

Finding hooks, audiences, and common threads 6:40
6:41

hook up front then I feel very challenged start and I think you know just knowing that for me there's still a weight that comes with this is on the front page this is going to be sort of broadly available it's almost like a a psychological barrier of like I need a good hook but the the the distinction between the Articles and the updates is I don't do that for the updates the updates are I are they're very timely they're usually about something that's happened very recently so this now it's earning season now so I'm writing about earnings I know exactly what I'm going to write about and the opening is I'm going to pull an excerpt from usually the Wall Street Journal or Bloomberg uh to uh Publications that write in a very predictable way they have the you know it's the traditional journalistic you have the nut up front and then you have sort of the additional thing at the bottom I just want the nut up front like

7:29

and that's my launching off point to talk about that and so that just makes it way easier because I know what I'm I know how to get started number two I know who my audience is they're people who are interested in what I have to write because they're paying to get it and so that is just very psychologically freeing in a way I assume way more knowledge on the audience I'll just like talk about things without having to feel like I have to introduce it to to other folks that said the best updates that I write are the ones that do have a common threat that that that there is like I tile something in part one and then part two and three sort of brings it around and ties some stuff together like you know I had something in mind this just this past week about you know uh I had already written about Google's earnings but they had a lot of interesting stuff this quarter so I didn't get into some of their comments about infastructure

8:15

spend which I want or capex which I wanted to get into but then Microsoft was all about the cack stuff so I was able to bring in the Google piece and then retie together how the Microsoft one started and that was you know both satisfying and I also you want to leave the reader with a you know when they finish they're like ah yes and it's like sort of brings it together and that that finishing moment when they when they finish reading it they feel that was a productive use of 10 minutes like and they feel sort of satisfied I don't think and I don't think it's a conscious thing that they're saying but if they're leaving saying like well whatever and they go to the next thing you I think you build up sort of a a well of not disappointment but boredom or whatever whereas if you get that little bit of aha bit at the end then it's like that was great and then and it just sort of leaves a a positive you know sort of affinity for

9:04

for for the product and so well I don't obsess to the same degree with the updates as I do the articles about having that thread you don't want to not have that thread too frequently so I did some of the back of the napkin math today something like 2,480 articles over the last 10 years for you daily updates public ones I said you're probably writing 250 a year I think it's not quite that many I think it's around 170 or 200 but whatever it's it's a lot yeah I've written like multiple books at this right well even then you do five or six books a year worth of content so that's like 50 or 60 books worth of writing over the last

Daily Deadlines and Productivity Hacks 9:45
9:46

decade we just need to get that out that is an insane amount of volume so people think I'm very productive and this probably gets to your you know to Circle back to the the day in the life thing uh on an objective basis yes I am extremely productive I tend to think on a personal self-reflective basis I'm a mass a procrastinator who wants to just you know lay around and and not do anything and like read Twitter and so there's a bit of a hack I'm a big believer in hacks and life in general it drives my daughter up the wall I'm constantly like setting alarms for everything there's anything I need to do i s an alarm oh that sounds so annoying yeah I know cuz my my my phone just always going off uh but the reality is is that you know to go back to this Flow State idea I am very much a Serial thinker like I'm thinking about like I'm walked in I'm Not Having side conversations I'm not doing sort of other things and so my

10:43

hack in terms of productivity is I have a daily deadline every single day and you know I go back to I remember being in college and writing a a college thesis and so I done a lot of work for it but the actual thought of like sitting down and writing this was uh very overwhelming and it was due you know you know the in May when we were sort of set to graduate and so basically you know I'm not I don't Advocate this as far as being a good writer I basically sat down like 36 hours straight some sort of combination of tons of caffeine and then a few beers take the the buzz off when I was like getting shaky and then back to caffeine I just wrote the whole thing and um and then I I took the whole thing and then me and some other folks we were having sort of a graduation party which we had invited my senior thesis adviser too and I walked up to him in the middle of the party with like my thesis gave it to him

11:34

and then like took like like slammed a beer like right there um but uh but the the all this to say is that uh for me the hack is deadlines make me very productive and so I've never written an actual book and I'm fairly terrified to do so because the idea of it being fairly open-ended as far as time you just need to do a little bit every day uh I I actually I question whether I could actually do that huh and so what I do with shery on one hand I think the blog style and I still call Sher blog is is very conducive to my thought process and also you know and the fact I'm covering stuff that's in real time like the idea of a book being frozen in time is is something that that I'm not sure I would like very much but there's also a bit where it just sort of suits me personally and and helps me get stuff done you've been doing this for what 12 years now uh 11 years 11 years do you dream and sleep differently in terms of

12:37

thinking about your articles now if I feel I wrote something that wasn't very good I don't sleep very well um and that's the downside of the daily deadline is there's days at work where you're just like I don't have it today not feeling good might check out early and that's just not an option uh I'm going to publish every day and the day that I write something that I don't think is great and I sleep well at night is the day I shouldn't be doing this anymore um so anyhow when it comes to to so the question of how often it takes right update the actual physical action updates are easier than articles happen more quickly but the reason it's hard to answer is the reality is is I'm thinking about what I write about all the time and the reason I'm able to be so productive to your point is people have a perception of my writing is that I sit down what I'm going to write about okay I'm going to write about this going to

13:39

do a bunch of research I'm going to think about what I want to say and then I'm going to sort of come up with something and I'm going to write it and that's not sustainable you wouldn't be able to write however many thousand uh pieces it is the way I think about it is

Developing a Framework for Writing 13:55
13:55

I have a a framework an overall view of the world and how it works and it's like it's almost like a like a machine and so when a piece of news happens I feed it in the machine and out pops sort of like a conclusion like if a if a happened then B then C then D then e and sometimes it's very straightforward like some some news happens I understand exactly why it happened all I need to do is sit down and write down the steps in the machine that's sort of the framework in my head sometimes it's a little surprising that's often where you can make like small scale prediction like clearly something else is going to happen CU there's a missing piece here that those are the ones I think those you have pretty good track record on those sorts of things what's an example of that there's going to be another announcement uh about you know X support for for feature y or something like that like this doesn't make sense in the

14:46

context of their business model whatever it might be so the third one is I'm wrong or there's something there's a void in the machine like I this doesn't make this sort of doesn't make sense that's usually I think where articles do come from where okay there's a lot of different pieces here that are being sort of pulled together and sort of make sense and now I can write a larger like articles are ideally a an articulation augmentation or correction of sort of the machine sort of sort of sort of what I've gotten wrong so you know everyone's thinking about like you know Ai and capex and I just mentioned that so I WR I wrote that piece about Microsoft Google last week and it's in my head there is some sort of article in the formulation stage about the various risks the relative risk factors of the hyperscalers um you know you have meta that AI all for their own product you have AWS which is all by and

15:49

large for third parties Microsoft and Google in the middle how does risk sort of align to that spectrum and what are you doing there you're looking at the different pieces and then are you trying to think is there like a unifying framework that Bridges this together like how are you beginning now to piece that article together yeah I mean I think at this point I definitely have the outline for an article so then there's a bit about is there some sort of piece of news that is worth being a trigger to write about this so one of the things I have found is I will I've written stuff that's just a pure like theoretical articulation of something it it usually doesn't resonate that much I think that this ties to the story bit

The Impact of Regular Writing Everyday 16:30
16:30

people are interested again this goes back to Che being a Blog but they're interested in it being tied to something sort of in real life sure so if I were to write a book about aggregation Theory or or something along those lines that would be a here I'm laying out this whole thing it's meant to be more sort of Timeless given the format that I work in a lot of my insights and this is why it almost be hard if I were to publish like an anthology or something like that they are anchored in the time and place of which they came even if the Insight is relatively Timeless um and so I think there is a bit where I think sh rewards the regular reader cuz you see the you see the development of this machine the evolution yeah then stry is sort of like a journal of my understanding of the world and so in this is a case where the format regular writing every day uh and being able to go back and say I got this

17:24

wrong or change sort of XYZ and now I think this in a way sort of writing a book would scare me cuz it's sort of locked in there it's like well no I don't actually think that anymore but it's in the book is something I enjoy well you're talking about developing ideas and you have your Doodles and then also you've mentioned logic three or four times are you somebody who is working things out with sketches and a whiteboard or does this happen in your head and you kind of get the outline just in the Ben brain yeah it mostly happens in my head I think the more interesting balance is how many essays are sort of in my head fully formed I'm just writing it out versus the ones where I vaguely have a sense where I'm going and by virtue of writing it forces me it forces it into a final form sure I certainly agree with the sentiment you know I think Jeff basos is famous for particularly in this but other folks

18:18

where the the value of writing is you have to fill in sort of the gaps between the bullets on the slide and you have to actually see what you actually think and sometimes when I'm stuck on an article cuz I don't have an opening whatever I know the answer is I just have to start writing because I the the issue is I don't actually fully know what I think um and for sure you know this is gets back to why I do still write even though I do a lot of podcasting these days and podcasting is definitely easier I can see you know I can see how like Bill Simmons you know sort of the granddaddy of I think internet writing even though he was Sports I would view him as a a forerunner of in to a certain extent you know now you just podcast all the time it's like yeah I could definitely see that that would be nice the reason why I do hesitate to ever do that is I for sure think that writing makes me a better podcaster because I've been

19:13

forced to examine make sure everything that I say is actually correct um I've been forced to actually structure my thoughts in a way that every semicolon is used to its maximum you know I'm not repeating myself but I am am sort of building sort of logical things and I think my goal is the way I always put it is I hope the value to my subscribers is not that I'm always right but rather that I've forced you to think about the issue and because I've laid out very clearly my thoughts my assumptions and the implications of that you are now equipped to come perhaps to a completely different conclusion like if I'm writing about a company and you're the CEO of that company you have way more information about the situation than I do but I've now given you a structured way to think about the issue in front of you you can bring to bear the additional information you have which may lead to a different outcome and in that case just

20:14

because you disagree with me or didn't follow my advice I would like to think I've done a large service for you so I'm going to throw something out there you tell me if I'm right or wrong so when I was scrolling through the on your site you have all the different concepts and then you can click on one of the concepts and then there's like three to five articles there and then you have like a oneline sentence where you've summarized like MKBHD for everything this is what it is or ESPN bundle this is what it is but it sounds like the way that you're talking about your articles is more in outline forms and logic trains rather than one sentence one liner that then you're kind of unbundling to see what's inside of that yeah I mean those sentence one letters honestly get written at the very last second before I publish cuz it something needs to go in that field uh so I I do sometimes feel I should give

21:03

more thought into those and making sure they're sort of a good articulation to the extent they're they're good and useful is is probably an accident to be you're not starting with those at all those happen right at the end at the end yeah I mean so I I have the the sort of a broader thought or sense of of and again this goes back to the the sort of machine idea I'm very rarely writing an article from scratch use like tsmc as an example so tsmc one of the values they provide as a Fab or as a Foundry is you go to them because you want to make a custom chip so they've enabled this entire world of anyone you know all these small companies can have their own sort of chips but you're you're not going to actually build an entire chip yourself what they provide and this is a big challenge for Intel and sort of competing in this space is they have like a huge collection of Lego bricks like all these different pieces of Ip

21:57

where you all the parts of the Chip And then you as a as a company you're adding your special sauce that's like the last sort of 5% or whatever but there's a ton of stuff about you know registers pipelines all these sort you know cash in out sort of stuff that's pretty standardized across chips and so what you're adding in is sort of the little bit that that makes that chip particularly unique and useful for you and this is perhaps a stretched analogy but the way I think about my writing is I have a lot of the concepts and overall things in place something new has happened and what how is that tie into what I understand or how does that explain how my understanding has changed the other thing people on Twitter like to make fun of me for um beyond the semicolons is I love to quote myself yes you do and it is worth mocking um I sort of feel silly when I'm mocking myself but there's a lot of times where um

22:58

sometimes it's very like pragmatic where I I remember I was writing something about uh I think it was like Facebook and their shift to the Tik Tock isation or whatever and my you know my thought was you know Facebook they were constrained by their Network actually that that's actually a fun of limitation how inter content could be and you know the more I write the more I forget stuff I've written I went back and I'd written exactly that like a couple years previously and the problem is that because that was when I had the idea and I worked really hard on that article and I go back and read it I'm like I can't say it any better than this like like what do I like what am I going to do I already I made this point a couple years ago so so number one it's just like look I already did a good job writing this why am I going to kill myself to write it again um but number two is again I think just the overall concept of what

23:46

Strater is as it being a journal of my attempt to understand technology and understand media and understand the internet the impact of the internet on all these sorts of areas is it's a it's not building something new every day it's evolving it's it's it's it's touching up the little bits and pieces of this is the way I thought the world worked it's kind of right but there was sort of a couple a couple things that I that I missed here and so let me remind you of where we're at and I'm going to sort of add on to that and I can get that it you know it it probably comes across at times as a little sistic and you know again it's just sort of like my signature at this point is that quote myself but there it is actually pretty integral to the way I think about what Strat is and how that fits into my process and how it is that I write thousands of Articles because I'm not writing a thousand new short stories a

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day and so there's an aspect of I've been developing this understanding there's an aspect of I've just been doing this every day for so long that the sort of process of how to do it is

Editing and Finalizing Articles 24:55
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is is um ties into that how in the world do you edit at the end of the day because something that happens to me something happens to a bunch of writers is you're in it and the challenge is when you're in the article you're reading it from your perspective and you're adding all of these intentions of hey this is what I meant to say and I like to sleep on things because of that I see it with fresh eyes you don't have that luxury like you're in it dare I say almost in a state of panic and now you got to do the edit so what does that what does that look like so I would say two things number one I will grant the caveat that not all everything I write but some stuff I write would could probably use more editing and there's sometimes I I it's and I feel this when I'm going like 5,000 words or something that's too long this really could be trimmed and that's just sort of the trade-offs of my of my model is that's

25:46

not sort of happening the reason I do generally get away with it is I rarely add of my pieces so and I think it's it's and this is a function of I it's not just I've been thinking about the article all day it's that I've been thinking about the article in a certain sense for 10 years and so the ideally the the tightness that I'm going for where I'm not repeating myself and it's a very logical thing is springing from a tightness in my own thinking and a structuredness in my in my own sort of understanding of the world and so it comes out in a fairly cogent sort of state and so I do of course edit but it's mostly about uh typos mostly about like repeating Words which drives me up the wall and then the one actually the one sort of hack that that I accidentally developed is now that all my articles I also are available sort of as podcast I read it and I always read it out loud before I published and that is actually

26:47

completely killed my typo rate like I I have like one a month now whereas I used to have many more than that cuz it's like just the reading out loud and you can feel that oh that's that's sort of stumbling I do think think I write by and large how I talk you can see I'm talking in long extended sort of answers and senses here but hopefully I'm talking in a way I'm not rambling too or you know I'm rambling to a certain extent but it's not like random rambling and I'm tying stuff together and ideally I'm linking it back to it's still in my head you ask me what my typical day is which I haven't yet answered but there's a bit where we're going to come back to that that's in my head and that's just generally how I write and uh you know I think about the human brain in terms of like computers to a certain extent like I just have a very large amount of sort of like L1 cash like uh you know where

27:40

the whole thing is sort of in my head and I can retrieve it quickly without having to go to like like like memory or whatever might be do you want to should we do the day in the life Grand reveal now well the the I think the the challenge actually in some this sort of gets to your editing point is like anyone else you're going to be more high energy more capable of doing stuff sort of in the morning um the the issue is that because I'm in Taiwan and if I'm doing interviews with people or I'm just talking to like my my assistant that I do all the writing and stuff myself but like all the like taxes and accounting and all that sort of stuff that's mostly all people in the US and so my mornings are usually occupied with just admin stuff or doing interviews with people or phone calls if I have calls and also Sports I'm a big sports fan and sports that are on at night in the US restaurant in the morning in Taiwan and

28:30

so I if there's a foot basketball game I'm probably to watch the basketball game um and so I will wake up very excited maybe you know I don't always know what I'm going to write but sometimes I know I'm going to write I'm like I this is great I'm going to finish the day early it's going to be awesome and then stuff happens during the day and then I get lunch and I'm kind of sleepy after lunch and it takes a while and I start procrastinating and then you get to like 3:00 or whatever like oh my God I have to read this update I tottally forgot about it so one thing I have done is uh I've sort of compressed my entire week into three days uh and so because the fourth day that I do now is an interview and so that's usually happens in the first few days of the week and basically I just uh somewhat physically destroy myself for those three days where there's a leg in the afternoon where I'm being lazy and procrastinating

29:17

and not wanting to do it I'm kind of low energy and then sort of the panic sets in and then you know the ear the the late afternoon early evening is is about sort of getting that written and getting that done um and then I sort of crashed out at night and and wake out I didn't quite imagine you with like a quill pen and you know some sort of very meditative office writing every single day but it is striking how much panic and I got to do this oh my goodness how big of a part of your writing process that is and frankly it's one of those things that uh I'm not particularly proud of it I wish it was better like I wish I was more disciplined was it like that when you were at the Daily Herald in college no same same sort of thing so yeah I mean the the in that case you know and that goes back to one of the things that when I took over the the editorial uh or opinion or the editorials uh when I was a senior

30:07

was student newspapers would do editorials and they would do it about um random National things like once a month or something no one cared uh what we what I wanted to do is like oh we're actually in a unique position for a very specific set of issues and so my idea was no we're never going to write about National issues cuz no one cares we're just some random s student newspaper we are going to write about these things and we're going to write an editorial every day or Monday through Thursday and then Friday will be like letters the editor and stuff like that and we did it um which mostly manifested into me doing it every single day and writing like all those editorials and of course they were all had to do it every day you had to come up with something you had to figure something out and then you and then you were doing it at the last minute and I loved it it was it was awesome and like

30:54

and it was successful like I think of our five objectives we at the end we sort of did an inventory and we felt we had succeeded on four of them and so there is a bit where that was sort of a foreshadowing of what I did shary was you know I now again I do an interview now but it's been four days a week for a very long time it used to be five days a week uh and I write about technology I write about media I don't I'm not partisan like to the extent I write about politics like I wrote a little bit about like some of the you know uh KL Harris or JD Vance or whatever and their views on this stuff and what impact that might have but I'm presenting it like this is just sort of my view on it I'm not saying who I prefer or XYZ cuz like I my goal is of course I have opinions my goal though is to have an impact on technology in the area that I am focused on and I think ultimately that can have more impact on the world and more

31:48

influence by sticking to what I'm good at just like the student newspaper hey if you're if you're hammer on something like Student Government Rel they care what the Su newspaper says if you write about like the Iraq war no one cares like it it it sort of doesn't matter and so gauging your what you're targeting what you're focused on to what you're capable and granted some degree of authority to talk and right about I think is is something that is useful and important

The Impact of Reading on Writing 32:25
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how do you think about your own read I mean I remember many years ago you wrote a piece called I think it was called the voters decide which was inspired by a book called The Party decides and so there's a book there and then there's a lot that you've built on Clayton Christensen and then you probably wake up in the morning and thinking through headlines like how do you think about your reading input and how intentional are you about that uh my reading is extremely intentional in that I I'm not sitting around in reading books but there are days where literally I know what I want to write about I know there's a specific thing I need to understand better I think some of the best Tre pieces are historical I age and that they pull into like I think a lot of things companies do go back to things that happen at their founding and that because that is still a part of the culture and it and to understand how a

33:14

company thinks you have to understand their culture to understand their culture you have to understand their founding and so there's days where I will be writing about something and I will in the morning I'm an extremely fast reader fortunately I will sit down and I'll read through an entire book really and then I then I that book will be a heavy reference for you know that that I'm that I'm writing and reading about now there's certainly foundational books like you mentioned sort of the Clayton Christenson and things on those lines and once I've read a book it's sort of in the you know it's in the repository that I might sort of pull on it and things on those lines I mean certainly Clayton christon is is the biggest influence in that regard for sure but yeah I so I read a decent number of books but not when I'm just like sitting on the chair relaxing it's like that's part of my workflow is I'm

34:00

I'm just going to plow through this and um you know at this point you know I know which Sexes I'm going for and which things I'm sort of really seeking to understand um and those are very satisfying ones I think or there's other ones where I remember there's an article I wrote ages ago when Apple was changing you know it's part of that update sort of explained this and what the implications were and sort of XYZ and the good thing about that is it's directional but obviously that that's in there sort of in the long run you know by the time you know the AI stuff came along and Nvidia and all that sort of thing like I knew at a very pretty deep level how how gpus worked and that was arguably born of a you know an intense day of research because I you know I think the the biggest compliment I can get is when someone will comment on Twitter or they email me and say you know I I have to say like

34:58

you know for someone that's not in my field you really got got that and and and and that's what it that's great cuz you want to we all know like the G Man Amnesia thing or whatever right you read something you're like oh that's really good and it's about something you write about like they don't know what they're talking about and it's like I I don't want to ever do that and sometimes I do and then I value greatly readers that will will will write in and say you got that wrong and and the next day you know it's not fun but John grber who writes staring Fireball has a saying that I have wholeheartedly adopted which is he says I love to be right and the best way to always be right is to immediately correct yourself when you're wrong and I think that is certainly something I try to live by you know with I'm going to get stuff wrong especially when you're writing every single day but to I try to

35:49

not just issue correction but also I Walk The Reader through my thought process how did I get to the wrong thing and you know what was that bit in my chain that was that was mistaken and I think that's it's not just good hygiene in general I write pretty authoritatively just That's My Style it's like it's pretty direct it's be a because of B because of C I'm not going to you know like dilly dally around it which I think is an important just general writing tip like you got to go for it you can't be like making excuses or hedging your bets you know too much in your writing if you you say what you think but that's also risky because when you're wrong then you kind of look like an idiot tell me more about that going for it I want to hear more about that I state things this happened because of this as opposed to well one could you know um and again I'm not saying I'm perfect in this I do hedge my

36:45

bets you know and you could probably tell days things where I do leave a sort of an out for myself so I'm not sure but bu and large I think you want to if you think something is the case your whole value is as an analyst is not being a you know not being a stenographer like you can just say oh yeah company said this therefore it's this your whole point is to find you know we talked about the the PowerPoint to the essay bit before there's a bit where what companies say are Powerpoints and the role that I can bring is to fill in the space between the Powerpoints of what companies say and you you don't do that effectively by just listing every possible thing or on the other hand just repeating the Powerpoints you have to actually the value you provide has to be something that's this is what's in the middle and so you say what's in the middle right and ideally you're right uh and sometimes you're wrong you have to own

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that but there I think that's the best approach because if you're sort of mey mouthed around it then it's not interesting writing like no one finds it sort of compelling yeah one of the things you do a lot is you'll look at a keynote and you'll say this thing happened they framed it like this and you'll say that's my wedge and now I'm going to analyze that and then this is what it means for the cultural grain of Google or Apple yeah I mean I love Keynotes um the I I love the first five minutes of a keynote cuz to me it's like they're they're trying to set a frame for what's to follow and to me the frame they're they're trying to set is more inting than the products like why is this the frame that they're sort of looking for um you know like s Adella does a lot of like he tries to tie stuff back in historically which obviously I try to do as well so I find that appealing generally but you know does that make

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sense is that actually a relevant sort of historical comparison like you know and what why are they doing this what does it say about the products they're they're introducing I think the risk that I have to be careful of is first off there's just a general confirmation bias my whole bit is I think I already know how the world works and I'm plugging this news into it so I have to be very very careful that I'm not looking for stuff that fits my pre-existing world view the funny thing is is that sometimes that makes me get stuff wrong so I overcompensate actually know I had it figured out but I'm like so eager to look but that's okay that's that those are mistakes I'll accept because it's a function of my process of making sure I don't give in confirmation bias too much the other thing is because I do actually think the narratives these companies say are important because they speak to the underlying focus of the

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company and its culture and things on those lines at the end of the day the actual like results do matter and the actual like specifications do matter and so I need to make sure I'm still digging into does the actual like numbers match this sort of narrative that's being put

"What Clay Christensen Got Wrong" 39:45
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forward so I want to talk about I want to talk about introductions and how you think about them and you're talking about stories mattering so I'm going to read this to you and I want to hear I want to hear your thoughts on it so this from what Clayton Christensen got wrong there's no question this the very beginning there's no question Clayton Christensen who developed the theory of disruption is silicon Valley's favorite business school Professor for me diving deep into his thinking in a corporate Innovation class was a breath of fresh air for management theory that explained all of corporate America but for its most successful company Apple what's going on there that's probably like the the origin article for cheer even though it was four to five months after I actually started you know the the bit was true I you know quite you're you're in you're in sort of business school and they have all these sort of

40:36

theories about how things work I mean I have I have a few business school bits that are you know somewhat relevant I mean number one is the fact I was at business school in the first place I sort of grew up on the Internet uh you know interested in technology in interested in the business side of things and by growing up the internet in the you know the the '90s 2000s NB were terrible right they were they were worthless um but I sort of grew up in a blue blue collar sort of area no one really went to work for Tech never even occurred to me to do that sort of thing even though I was super into it in sort of the Doom era and and so I was in sort of the 2000s I was in in Taiwan teaching English and my my wife's like you know why don't you all you do is read about and talk about tech why don't you go work in Tech I'm like that's a good idea I should work in Tech and I'm like oh what I'm like what 27 years old with and

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my no career relevant career experience like the only option to me was like to get an NBA H that was like the way sort of like Get legitimacy in the US job market and so I did that turned out it was a great fit like just cuz I had a lot of implicit understanding of things like uh leverage and margin and and Game Theory and all this sort of stuff that suddenly I now had was given a language to sort of articulate things like that with and so the NBA was great in that regard but still like a lot of technologist people in technology uh was fascinated by Apple very interested in it and uh well there's actually a step up there's one more thing so I go back to to business school first day first class you know management 101 or whatever it's called and I'm flipping through all the case studies we're going to do for the semester and there was Zero technology companies and so I go to the professor afterwards you know you

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know I'm an annoying student like that I'm like why are there no technology companies and the answer is like well there's broad principles that you learn from these cases that are applicable to sort of you know companies in all Industries and I'm like I don't think that's true and this is actually one of the core things about shery which is technically it is true but what I think makes technology unique is the nature of zero marginal costs and zero transactional costs by zero marginal cost you know one more person visiting google.com doesn't cost them anything do there do they have substantial server costs of course but like one extra person doesn't cost anything and this applies to basically everything on the internet zero transaction costs is Google can serve 7 billion people without a swept because they their actual interaction is complete mediated by computers and the implications of

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this on business models and strategy I think are very profound and it was very and and to me it was a major hole in the curriculum that this wasn't the case yes you had all these equations that you could use to analyze businesses but if you're putting a zero into an equation the equation comes out looking totally different because zeros cancel so many things out so number one a from business school is there's an entire Arena of strategic analysis that at I'm you know at a top five business school is not even aware that's needing to be addressed let me just pause you one thing that I think is a really good prompt or thing that you find yourself saying when it's like I should write is when you're in the midst of an expert like you were in business school and what did you say I don't think I agree with that that I think for a lot of people they say I think I'm missing something but somehow when you

44:13

find that can you start asking yourself maybe I'm right let me go explore that because if you find yourself saying that and you are right you have the seeds of a really compelling piece well well I mean there's a certain bit I think to be writer or to be a writer particularly of what I do which is my own site on the internet that entails some combination of narcissism and delusions of grandeur um where I think I'm right and I think I'm right enough and compelling enough that I can just put something up there and you're going to read it you're it's going to be spread around and it's going to be interesting um I'm Fort I'm not sure this is good career advice I'm fortunate that turned out to by and large be the case you know I started stery with 380 or something followers on Twitter no one knew who I was and there was no hand up or favor given or whatever is just I went up there and wrote what I hope was compelling stuff

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there was a social media was different then there was a lot of currency to be gained from sharing interesting links you know and different than today when links are suppressed and there's so much stuff out there in by and large and so I certainly benefited in that regard but yeah there's a bit like that's just my personality and thought process is I'm an English teacher from Taiwan and I'm going to go tell the strategy Professor that I think you're curriculum on day one is BS cuz you're completely missing you know sort of a that's awesome yeah sort of it love that so so that was that was sort of uh the first sort of business school bit but the other thing was Apple as I mentioned and apple did everything wrong right they didn't have a division they had a functional organization a divisional organization the way they sort of did marketing the way they did did product development all this stuff was supposed to be

46:00

commoditized and like why why were they able and at that time there was a real fever around the idea that Apple was Doom was imminent because just like the mac and PC uh the iPhone is going to fade away all developers go to Android cuz it was open and then the iPhone would would become a fractional part of the marketplace and that that that whole argument around that broadly speaking really really ties a lot of Chey threads together number one everyone gets the historical context of Mac versus Windows wrong it was not Mac was there and then Windows came along and knocked it off Doss was there before Mac and that was Downstream from sort of IBM and the Dos Market was massive and large before the Mac ever even shipped so it's actually the inverse where the iPhone was first and Android sort of came later and that it's amazing that is just a basic historical fact that basically everyone in the world does not understand I

47:03

greatly respect professor christon as I mentioned he's had more influence on me than basically anyone else he got that fact totally wrong and it meant his entire thesis fell apart but that there's a bit where that's why it's really important to go back and read those books go back and make sure I get the bits right cuz if you just go along with the popular sort of thing you actually don't go back and assure that make sure that what the myth is is what actually happened you you can actually get huge swads of analysis wrong because

The Importance of Knowing Your Stuff 47:30
47:30

your one of your core assumtions is sort of mistaken well let me let me talk through a few things that I've taken so one of the big ones like I said is you got to know stuff another one is to once you have that background knowledge to just trust your point of view and to not be hesitant like there's something that you're doing where you're taking that point of view you're like okay I'm going to go for it and I think part of that is probably tempermental where you're saying okay this is how I am for sure I mean like the um you know if you do like personality test whatever I'm like high and disagree disagreeable 0% I'm 100% sure that's the case and I think by the way and this does I think color internet discourse generally anyone who's successful in the internet is probably very highly disagreeable like because the amount of abuse and disagreement and people coming at you that you you know

48:18

PE people weren't meant to see the get the level of feedback that they do right and most people just sort of want to get along and and want to be along and so and you can see them Wilt and and it's a very difficult thing to deal with and it's not and I'm not to say I'm impervious to it like there's you mentioned not sleeping there's because I haven't slept because like something got like spun up into a completely different Arena of people that I wasn't aware with you I wasn't focused on and I'm getting all these sort of attacks and it's it's very difficult and challenging to sort of to sort of deal with uh but at the end of the day um I am temperamentally sort of don't care well the other Ben Thompson prompts so to speak are what are some places where there's an expert and you understand their Theory but it doesn't explain something and then where's a time in your worldview where you're saying okay something isn't

49:12

lining up here and I resonated with what you said earlier and just think about to all the daily updates that I've read some of the times when You' started you said yesterday day before I got something wrong here's what I got wrong this was the hole in my thinking those are almost more instructive and I felt that as a reader those moments are when

The Value of Regular Content Production 49:30
49:32

I feel you as the writer more intimately than when you're talking about aggregation Theory or something sort of coming from on high you're much more professorial right well yeah you're you're getting inside my thinking which I think is is intrinsically sort of more intimate in that regard sure sure you told me earlier come back to volume let's talk about volume well so you know this this ties into the sort of daily schedule it ties into the the fact that I still think of myself as writing a Blog um and it ties into the business model which is you know as a contrast uh I'll there's a guy named Dylan Patel writes s called semi analysis uh and he he and he will get these incredible Scoops or details about the next Invidia processor or what the production pipelines are or in in like components and things along those lines incredibly valuable stuff like like Market changing stuff potentially or strategy changing

50:30

stuff and you know we've talked about sort of business models and what he has it's a substack and this is a guy it's an amazing internet success story he grew up posting on forums and like he was like a Reddit moderator at some point and now he's like like the authority about stuff like this and he charges something like $500 a year and he only sells annual subscriptions and the reason is he might only write one article a year that actually matters to you but you really have to read that article and and for him to charge what I charge $15 a month you know uh that would be weaving so much value on the table because you just sign up for a month read the article and then cancel and you like because it's you know that what he's selling is these occasional super incredible powerful and useful sort of insights and so he's doing a good job of maximizing his return on that what I do is I charge $15 a month

51:22

it used to be 10 it's sort of made its way I've done two price ra raises I just just did another one part of what I am selling frankly is the ongoing production of content and it's almost like it's like monetizing my hack which is my hack is I have a daily deadline set have to publish every day what I'm delivering to you is any one piece I write is hopefully insightful oftentimes my most insightful things are in the free articles which you could just read sort of anyway but what you get when you sign up for shery is you're going to get three a piece on Monday Tuesday Wednesday and hopefully a very compelling interview on Thursday uh obviously have a podcast you get all this you know it's a big bundle hopefully something's going to be interesting to you but it's that regularity of delivery and you're paying not for the archives you're paying for the confidence and and even if you don't realize what you're paying for just

52:18

knowing that you're going to get this in s of your inbox every day and one thing that I think is is is is kind of interesting is the reason I can do this for so long is I'm wri all stuff that I'm interested in if I'm like trying to cater to my customers I think that's a recipe for Burnout the one time I did almost burnout is like 2019 2020 I was WR about like regulation and antitrust and Congressional hearings and I'm like oh this is actually horrible um like it's burning me out I like I work a lot that's not what's burning me out it's ring about stuff that I don't that is kind of soul sucking at least from my perspective but the and you also over index on Sports cuz that's what you love talking about I do write well Med I mean number one that I'm in the media so that's interesting number two I do think the media is uh it's it is indicative of everything that's going to happen what's going to happen to everyone the canary

53:07

and the co mine right because it is digital inherently and the media you the reason why there's like on Wall Street TMT Tech media Telecom or maybe it's Telecom Media Tech remember is those are all zero marginal cost industries that is the connective sort of tissue and so it's interesting I do get the media I would say my analysis of the media is wrong more often than is about tech I think a lot of that is I don't fully understand all the incentives like I think a lot of my stuff about Hollywood has been directionally correct but I've gotten details wrong in part because Hollywood's a city of big personalities and like people do dumb stuff because there's prestige in it or sort of XYZ whereas Tech you're you have people doing dumb stuff for those reasons but much less so it's like Tech is pretty Hues pretty closely to its broad broader Inc incentives um but yeah it's also fun to write about

53:59

all which is to say I mean so some of it is self-serving it ties into my hack all this sort of bit but I do think that volume or quantity is underrated and this is a massive revealed versus state of preference thing everyone will say oh I just want you to write good stuff like don't worry when you write it I'll read it and again maybe I'm just telling myself this but my sense is it would be hard to have the degree of success that I've had if it weren't for the just day in day out sort of grinding and you know you're going to get something from me and yes that occasionally leads to stuff that is maybe not as high quality as it should be maybe you could use another round of editing but I suspect that the actual process leads to far more interesting and compelling stuff because there's no choice you're going to have to write regardless and I do think it's something people find valuable and it sort of ties into their

54:58

their their daily life I haven't done a lot of like deep analytics about my readers uh I think it's important to focus on what just focus on what you're interested in that's the key thing to doing this for a long time but I have monthly subscriptions and I have annual subscriptions and at this point the vast majority of my subscribers are annual subscribers which is great because that means they're committed they know they want to get this and for me it's freeing like if I have one bad update okay fine I have I have a year to make it up to them before they have to sort of renew but one thing I did notice that was interesting I was trying to understand like the lifetime value of the different groups is I had to cut out people who would subscribe in the first month and immediately turn off auto renew and those are people it makes sense they wanted to try it or S they want to get one article and so I just separate those

55:45

from people that that that sucked through but I when did deeper analysis it turned out my best cohort was people who subscribed and and turned off auto renew and then sometime in that first month they subscribed annually and they were people that like they wanted to try it out and I always deliver them every day and they're in the habit and at some point they're like yeah I want to keep getting this and like why don't me why even bother with monthly it's a discount to go sort of annually and sort of walk in and I think you know I have a lot of subscribers that have you know they've been they've been there for years and years and they're awesome you know I still have my initial set of subscribers that you know you they got me off the ground and I'm incredibly grateful to them and I've had lot of people that have ched and you know my turn rate is very low but it still obviously sort of exists I you know I bounce them to the

56:38

they still get the free articles sort of bit and it's funny like a ro company should understand their business I don't want to understand my business too much to a certain extent because as long as the number is is not going down then then things are good so we don't need to name names but I I got to ask what is it like when you're seeing someone come in it's like Jeff Bezos or Mark Zuckerberg like that's a big name yeah I I I've never sort of tried to read them um and know who's coming in actually there is a funny story about this which is you know currently shy runs on my own sort of system um that will be available broadly sort of hopefully soon but for now it's sort of like a custom sort of thing but for a while before that I was I was working with the service club memberful and I was like when they first customers they they actually watch my first version cheery cuz this business model

57:24

didn't really exist so it's sort of all glued together by myself and then they started this like and they they did a great job but they emailed me one time saying hey just let you know you have three subscribers that we accidentally double charged we've already refunded them and then they gave me the names it was random person a random person b top five Fortune 5 CEO was number three and I'm like wow I didn't know he was a subscriber it was like he was like totally random but I I I don't like knowing to it's weird actually it's a real Paradox on one hand I don't like knowing and I usually forget pretty quickly because I don't ever I want to write what I think I don't want to ever write because I know someone else is sort of reading whatever might be and frankly they don't want that either like I do you know most relevant well-known sort of Executives do reach cheery and I've had a chance to talk to several of

58:21

them the reason they find it valuable is when you're a CEO everyone you talk to to inherently has an incentive to tell you what you want to hear right cuz just it's inescapable even if you have the most disagreeable straight talking person ever there's always going to be some sort of constraint there and so they like reading me or talking to me because even though I'm lacking a lot of knowledge that they have because I'm not internal of the company I'm just reading their financial reports or watching their presentations or listening to their earnings calls uh I have no incentive to Li to them or no incentive to sort of I just say what I think they they can sort of and to it's interesting the extent I will get pushed back from companies about stuff I write I never get pushed back from CEOs it's always people lower down the CH people marketing people or even senior VPS or stuff like that uh which disagree and

59:11

say you don't get this this is wrong did it I've never had a CEO push back at that level what's going on there because they they appreciate getting a different point of view of course they want the public record to be in a certain regard and and perhaps they will email their head of PR say email Ben and tell but um they NE I've never gotten push back from Co personally and my perception and I you know again just to the extent I've talked to them sort of in person is they're so hungry from a distinct point of view that doesn't care about them that like I don't care what what what they think like I saying what I think I might business models not dependent on them they're paying $15 a month like everybody else and I don't even know if they're subscribers by and large and I try not to know and so the flip side of the Paradox is of course I'm thrilled their reading right like the you know shery at the end

1:00:05

of the day I want to have an impact and you know I used to work at Microsoft and you know the you know I care I had opinions and like what the company should do and one should be and the great irony is I almost certainly have way more impact on them than I ever would have had I stayed for 10 years and sort of been promoted the chain and been in the internal sort of political fights and that's amazing like there's a bit where my core audience is a very small collection of like CEOs and everyone else is helping pay pay the bills you know sort of go along with it well one of the things that I want to make really clear is this is a

Business Models and Media Companies 1:00:45
1:00:44

compliment that's going to sound like an insult so bear with me there is something now sitting here that is very unremarkable about you and Strater and it's because the business model that you founded and that you pioneered has now become a big part of the world and I think of that in two ways first of all you the the founders of substack have explicitly said that you inspired their model that's the first thing and then the other thing is Onan media companies have really become a thing both in writing where you know I guess you had before you you had bloggers like Andrew Sullivan and Ezra Klein but now we have people like MKBHD we have people like Joe Rogan it is a big thing now that single-person media companies can have all this reach but you go back 10 15 years ago that would have been insane they're going to disrupt ESPN they're going to disrupt MTV what are you talking about well I mean the at the end

1:01:37

of the day from the user perspective time is time so every minute spent Rory is a minute not spent reading the New York Times or not spent reading so from that perspective uh I am competing on an equal plane with the largest media companies in the world and so and that that's all that matters and then for it to pay off from my perspective the advantage you have as a single person Media company is your cost structure can be totally different like like my my cost structure for your the first four or five years I was literally one person I did everything I did my taxes I did my accounting I answered emails I did sort of all those sorts of pieces and while that was busy and stressful particularly since I wrote more back then than than I sort of I do now um then you know it was pretty insane the amount of stuff I was doing that meant my my only costs were basic credit card processing fees right

1:02:27

and and like you know cuz my time was obviously you know valuable but it wasn't I wasn't paying paying a salary is just sort of like whatever came out of it and I'm working in a zero marginal cost business for me to send an email to 100 people yes email costs money but on the order of sense is the exact same is to send it to a th people or to send it to 10,000 people or to send it to 100,000 people the the beauty of media is uh it is on the Internet is is perfectly scalable on the back end I can write an article that reaches a million people or reach or theoretically can reach billions of people now do billions of people read it no but sometimes a million people do um which is amazing it's media is not scalable on the front end because you have to keep writing stuff every day like like the the and so that turns people off from it it makes media I think maybe often a poor investment and that's a real challenge

1:03:19

but that's that's an opportunity for the people that are capable of that have that generative function so is appropriate for you to start with what your day-to-day look like cuz that is the part that that is marginal costs like I have to literally sit down and write that update every day once that update is written then I get the internet advantages I get to send that send that to Haring people are subscribers or people are on my mailing list or whatever it might be so that is and you know and I wrote a lot about that when I was getting started and like why this is an opportunity and the different frames of reference and so I'm very proud of the model I'm proud of substack I'm proud of everyone that is sort of doing this and I hope to some extent it gives even though I've never been the CEO of a Microsoft or a meta or or or an apple hopefully get some sort of credence that I'm not I know to some

1:04:13

extent what I'm talking about because like the fact that yeah I was the first to sort of really do this again newsletters existed on Wall Street in particular those are more of the uh you have like 100 subscribers and you start charge $10,000 or $100,000 or sort of whatever it might be this idea of like you know stripe was really the the a core piece they started in 2009 the product came out 2011 I launched in 2013 and this ability just take credit cards easily do a subscription not have to muck around with PayPal or whatever and basically make it up in scale like that the internet lets everything be made up in scale and that is a challenge like it's funny people will bemoan the fact I only have a thousand listeners in my podcast or I only have a 500 people read my blog it's like well let's step back here let's go back to the '90s and tell someone you sit down and a thousand people listen to

1:05:05

what you have to say every single week like it's it's pretty remarkable I think the reason why people don't fully appreciate is number one it's everywhere number two through social media you see all the success stories you're not gauging yourself sort of appropriately and that's a problem with all sorts of stuff and then also the monetization is obviously hard because you're dealing zero Mar cost content advertising operates at scale and so the key thing with stry is I mentioned I'm will pric compared to Dylan Patel but I'm very high pric compared to most content in the internet and it's really about maximizing the average revenue per user which is if you're selling something you have to you have to be confident to charge for it and you know if you have if you charge $100 a year you have a th000 subscribers that's you know thousand true fans you know the the sort of classic sort of essay you have

1:05:57

$100,000 a year and that's a pretty good outcome so when you see people launching a substack trying to charge for content and it doesn't work what went wrong what is the mistake the Strate the strategy mistake that people repeatedly make when I started I was the only one doing this sure so that certainly make I want to be humble about that fact that makes it that that makes a big difference one of the real big challenges is and this is where the volume thing frankly comes in is you need a way to acquire customers but you also need something to sell H I solve that by just writing a massive amount some of which was free and some of which was paid if you're only generating One content a week one article a week which is frankly is a is a lot how are you going to balance customer acquisition with actually having a product that people feel compelled to pay for because they want to get access to it I think that's

1:06:52

really hard it's it's and it's harder today just grow part of the internet Advantage was social media is B my best marketing is my customers telling other people and that was when links were being pushed on social media in the way that now they're just that's right that's right which makes and so that that makes it astronomically more difficult today um you know I I'm now able to launch new things like I start a new podcast and I can overnight have five figure sort of listeners because but that's because I'm lending the sort of audience that I gain before sort of into getting that off the ground so what do I say to someone who's trying to start a new podcast that has no audience and no whatever it's I just want to be humble about that sure but also there's something fundamental to strer that businesses can pay for it provides value WR right write consistently really good stuff I mean the the the thesis that I have is the

1:07:52

most important article you write is the second article someone reads so they go on your site and they're like wow that was a good article and then maybe they leave and they come back later because they follow another link or they click somewhere on your site and they read a different article and they're like wow that was a really good article and suddenly there is a level of consistency and expectation that you've established with that with that reader and so some of the things I did with Sher is funny I mean I joke about it's a word of mouth blog with a name no one can pronounce um but it's also memorable that's why I can't remember the name of that box how do you say that again uh shash had a custom font when custom fonts were a completely new thing in the internet uh shary had the hand drawings uh sh was orange the reason for all that is is I wanted to capitalize on that second visit where people would show up and

1:08:46

they'd say I've been on this site before because they were just following links on Twitter and then and then oh I see that drawing oh that a guy that does hand the hand drawings and what I want is that user to start to develop an expectation that this site has good stuff and and I did that I started shery with the goal of the it monetizing it but the way I always thought about it is when I monetized it I wasn't going to drop a pay wall I was going to do more stuff because I wouldn't have to have another job I could write more I was probably insanely turned out okay but probably insane at the time confident I could generate more stuff I'm like have so many ideas and so when I add the daily updates like yeah I still have the free stuff but now if you want more you can sort of get more stuff and and I wanted to build a desire and linkage in people that like this is a place to go to to get good stuff when something happens in the

1:09:41

world and Ben doesn't write about it I'm disappointed like I wish Ben would comment on this sort of thing and then I you know day upate comes along oh you want me to comment about news of the day as it happens $10 a month and uh and you can get that so I want to do a little segment here called how the internet works so I'm going to give you framework sentences that you've written and I want

How the Internet Works (Google, Facebook) 1:10:00
1:09:59

you to basically unpack them and I think what we can do is we can get the Ben Thompson model of how media Works online first thing is this is exponent my favorite episode of exponent episode 12 it's called the internet rainforest and the thesis is this that the internet enables Big Winners and small focused Niche players yeah well there's lots of names for this it's the barbell effect I've done the thing called the smile curve and this is basically the idea that the internet the implication of zero marginal cost and zero transaction cost and this is sort of aggregation theory is everyone had a vision of the internet of being a a million sort of winners because it's you can go anywhere you can do anything the reality is when you can go anywhere and do anything you're overwhelmed with abundance you have too much stuff and so the pro whereas in the analog world the controlling factor is scarcity and so in

1:10:51

the analog world it's who can get you stuff so it's distribution that matters on the internet anyone can get you stuff cuz it's all free uh and so you have too much so what matters is Discovery who can help you find the stuff that is sort of interesting what this means is the platforms that control Discovery they get more users they get more users they get more Supply because that's where the users are which makes their platform better so they get more users you get a virtuous cycle that the implication of the internet is not you have a lot of winners is that you have very few very large winners and so this is the Googles and the Facebooks of the world this is all very obvious now but I think you know shrei would in the early days was really explaining why are the expectations around these companies wrong like the great shame is I had no money when I started sh uh I would have been much better off had I had the money

1:11:36

at now and then just investing in my uh thesis back then of like basically CU like the big the big five completely outperformed VC completely outperformed anyone over sort of the running shery and was explaining why that was the case why are they why are all these companies despite the fact they're the largest companies ever still completely undervalued um and that you know was obviously sort of turned out to be the case that's probably why have a lot of loyal subscribers is I help them make a lot of money so um uh so good for them um so you have those large players but at the same time all these bits about the cheapness makes all these small creators completely possible and the key thing is is traditional media can't shrink down enough their cost structures were built for a different world they're built for a world that's predicated on having white manufacturing operations which is printing presses and delivery

1:12:26

trucks and things along those lines they which which entailed a certain sort of lock in in their Market that they had if you're online if you can get just a few subscribers that are really or a few people that are really loyal to you and really like your stuff and there's a gazillion niches in the world and now you can address the entire internet so you can pull I have subscribers from over 100 countries like you you can find the people that like what you want and then you can charge them again a high average revenue per user and you can have a have a very good life um and so that is the case in Industry after industry like like like cost internet cost structures and Niche and find your tribe versus zero marginal costs serve everyone sort of get these aggregation effects everyone in the middle is screwed and um and that started with print and then it happened with with is happening with the rest of media and

1:13:19

you're seeing it happen in all sorts of Industries right let's do a string of sentences now that truly changed my life I remember reading these in my college dorm room and I was like I think uh that might actually influence what I do for a career here we go people underestimate the scale of the Internet it's not going to appeal your content it's not going to appeal to the whole world but if you're going to like it you're really going to like it yeah this this gets in the bit about the whole world's your addressable Market people you know you real like every sory post the addressable Market is literally on the order of billions of people no there's the there's the classic phrase everyone makes fun of if we can only capture x% of the market that's actually true in this case like and you know is funny there's a lot of like well-known VCS and folks in that area when I la the the the pay version of

1:14:11

cheer he's like you know love your stuff but no sh that's not going to work not um and it's interesting people whose job is to understand the scale of the internet did not sh scale the internet in that particular case like it turns out uh there is a good number of people that are willing to pay because they really like the content and and we see it it's not just me there's all the success stories on substack there's all the YouTube success stories to your point these individual creators and there's no there's no cap on that people have like subscription fatigue and they're like they I think they underestimate the number of niches and they're they're always focused on themselves there's a lot of stuff and actually their problem is they're too interested there's too many stuff they want to subscribe to and so they're frustrated how much they're spending on subscriptions without and they forget

1:15:03

about the fact that most people everyone is different everyone is not like them and people will subscribe to you know the most Arcane sort of Niche Focus sort of things and uh and it pays off let's do one more most of what I read is the best there is to read on any given subject the trash is few and far between and the average equally rare well I mean I think this is just an internet effect which is and this is a function this is why Discovery matters what bubbles up what gets traction the links that get shared are shared because they're they're good and you know this is a reason why you to about things like misinformation or whatever one of the worst things that exists in terms of intelligent conversation about the internet is search because you can go on and search and you can find absolute garbage because this is like the whole Tik Tock isation of things the vast majority of videos created on Tik Tok

1:15:59

are trash what the magic is is that if you if say 0.001% are great if you can ramp up the volume than the the the absolute on the internet the absolute number matters most and and so you just like if you have a huge amount of volume even if a tiny percentage of that is good the number of good things is quite large and it can be so large that it starts to overwhelm sort of other sorts of things one of my favorite lines on this is from a little book by Aubrey mishenko called human is media and it says that before the internet curation happened before the publication of something and now curation happens after something gets publicized and that's what you're saying you just let everything go everything can be shared and then you have search or algorithms that then say this is the best stuff now that's what we're going to show that's right so what the curation is another word for discovery which is which is the these platforms

1:16:57

that help you discover the best stuff and they are heavily motivated to engender massive amounts of creation and actually it is a positive for these large platforms if there is gargantuan levels of junk out there because the implication is there's lots of stuff being created which mean you know there's going to be lots of good stuff too I want to talk about writing conclusions so let's go back to what Clayton Christensen got wrong here's how you ended it apple is and for the last 15 years has been focused exactly on the blind spot in the theory of low-end disruption differentiation based on design which while it can't be measured can certainly be felt by consumers who are both buyers and users it's time for the theory to change so as you're thinking about ending a piece what is really important to you well I think that was a good example of how I could be very wordy and use a lot of punctuation so thank you for that uh

1:17:50

number two you are calling back to an article I wrote in 2013 which feeds my worst fear is that I peaked early and it's been downhill ever since um well it is the staple Ben Thompson peace uh but number three conclusions are hard for sure I think the best conclusions they T this is kind of cliche writing device but they tie back into the the introduction and they they they they not the threat as it were and so I started that piece as you quoted before saying everyone admires Klay Christensen um he's very smart but he's got something wrong and so at the end I say what he got wrong so that was it was fairly yeah I and I do think when you talk about you asked about editing before to the extent I do edit again I think I write with a pretty high degree of clarity but what if I do rework something sometimes because it's too long I just got to take something out um but the other big thing is I'm not

1:18:48

pulling the thread tight on the conclusion and so I I want to I want to you know go back sometimes when I'm writing the conclusion I will I'll copy the introduction at the top and I'll paste it down at the bottom so it's right there in my my line of sight and so I'm thinking about like how am I tying this together and sometimes like I can't really tie this together and then I need to go back into the essay and put in a couple of guide posts so that I'm I might driving sort of to pull it back in how does that work usually when I came up with the introduction I had a sense of where I was going sometimes the piece goes in a different direction and I have to like sometimes scrap the introduction which is very sad uh but sometimes it's like okay no it's there I just there were a couple guide posts I needed to add so that when I get to the end I can sort of link it back to to where I started um so I think those are

1:19:36

the best conclusions um conclusions are hard though like the the but I do think they're important like you know you you you want to and they can be risky cuz sometimes you to get a good conclusion you have to like maybe go a little bit more on a branch than you want to say sort of sort of whatever it might be but I would say the challenges of the conclusion are tied to the challenges of the introduction and again I think that's sort of runting 101 in a certain regard when you're editing and you're in a story how do you think about the pacing of that story and what the right kind of tempo is for a reader it's definitely a a challenge between saying everything I want to say and having it be short enough compelling you know again I think that's where when I could use more editing that's often the case or it's l at night or I'm just like you know like I wrote a piece about it was getting related to

1:20:29

European Regulators or whatever and I had a whole section in there about uh you know using the European internet and this annoyance that everyone wants like I kind of can understand why they're so obsessed with data because everyone's trying to collect data that's totally unnecessary and I thought it was actually like like you go you sign up for like to go visit a museum and they're like you know what was your income last year or something like that I I'm over it slightly with as your passport information like all the sort of stuff it's like I just want to buy a ticket right and the US is so much better at this you go in like they're like look we're we're just going to do a transaction we don't care who you are we don't want to know who you are I was in Barcelona a few weeks ago and I was trying to rent a bike and they started ask me for my passport information yeah it's out of control everyone has their

1:21:13

own bespoke system and the US like everyone just uses like a standardized platform right and and and actually and so my take there was this is actually an area where uh the lack we've actually ended up with a much better system the like the European internet feels Frozen in time in the 2000s when every site was trying to collect data cuz the data is valuable or whatever and I think it was a good aside and a good anecdote it was also like a 6000w article that it wasn't directly pertinent to it and so I was going through I'm like I really should cut this this is not necessary but I was really in love with it and it was also like 3:00 in the morning and I'm like now whatever it's it's going in there um and so I got I got a bunch of tweets about the I need to keep it I need to keep like Ben must have had a good vacation cuz his first post back is like a 6500w bromade against the uh the the European Union um but uh so yeah in

1:22:05

there's probably a bit to be totally honest where I've gotten worse about this over time because like people are going to read it and so like you're going to you're going to hear everything that I have to say I should be I should be more disciplined about there's a bit also the the classic saying if I would have had more time I would have made it shorter where if I'm going through like summers are super hard uh because actually being in Taiwan is a big benefit CU I work during the day and I published in the evening it's morning here here I wake up at 3:00 a.m.

1:22:35

usually and and I write and there's a bit where here you wake up at 3:00 a.m. yeah uh on days that I'm writing jeez so so did you get your writing done today uh I didn't publish today so yeah in July in the first part of August I don't do interviews so that's that's sort of like my break for the years I only I only publish three days a week but um and so there's a where and I I still finish later than I want to and I'm under the gun and I feel like my summer updates get a little long uh in part of that is is honestly just a function of and I almost hesitate to talk about it it's not my reader problem like that I'm busy or I'm waking up early I think it's important for writers to adopt the sense of at least from my perspective I'm selling a product it's if you want access to this you have to pay for it I think I I I'm very this happens less but early in the days people there's a lot like personal appeals like oh please

1:23:29

support me and a lot of writers you wrote something you want everyone to read it so they want stuff to be free and I'm to a lot of writers like no you're running a business you need to make like you you have to give someone a reason to pay and a reason to pay is not charity and a reason to pay is not that they want you to be popular the reason to pay is because they want to read what you wrote and you're not letting them read it and there's a bit where a lot of writers are too hesitant and they're not disagreeable enough to basically tell their their potential customers no you're not going to get a read what I write unless you pay for it and you need to have a clearly articulated Val you know what are you selling and um and so to that end I don't like talking about myself I don't like talk about I'm super busy or I'm dealing with XYZ and so this is you know late or whatever that's why I don't take

1:24:17

personal days like if I'm busy or stuff's going on that is not my reader's problem my reader signed up to get an email every day and I'm and my job is to give them that Emil every day and my problems are my problems that said my

The Challenges and Rewards of Niche Content 1:24:30
1:24:29

updates get a long in the summer cuz I'm busy and waking up early so so if I'm the chancellor at Northwestern at the business school and I were invite you back and I'd say hey Ben you're going to teach a semester and we're going to train people how to do what you do what would be on that curriculum how would you structure it I mean I think the most important thing is what you're going to write about like the everyone thinks I have the best job in the world cuz I get to you know quote unquote sit in my pajamas and WR about the big five tech companies but if you wanted to do that you are literally competing directly with me and directly with with with with Twitter everyone has comments about like I'm getting paid to do what millions of people do for free on Twitter every day which provide their their opinions on the big five tech companies uh so you're jumping into a very big pond in a world

1:25:18

where you have no inherent advantages of like geography like you could have a bunch of sports colonist in the US before cuz they were limit lied to their geographic area of where they're published once you're online you're competing with every sports colist in the world now we're just going to read Bill Simmons they're not going to read your local colist or whatever it might be the Dynamics of competition completely change what you can do and this goes back to the niche bit is you can find your own Pond what you need to so the most important thing for succeeding on the Internet is defining who your target audience is so for example there's a guy Neil cybert he writes about apple right he writes about Apple every single day and I write about Apple so we're nominally competitive but if you really care about Apple like he's the guy youed should sign up for he's gonna write about Apple every single day

1:26:02

and that is a he's choosing in some extense a smaller pond because he's only read about one company I'm rri about a bunch of companies and media and stuff along those lines but he is owning that pond and and I think there should be someone that writes about Amazon every day there should be someone that writes about Google every day um Casey Newton writes about like social media networks generally and he's been very successful sort of doing that I think you what it it again it's a cliche but I think it applies very much is if you want to be the successful fish in the pond the key is making your own Pond uh not trying to sort of defeat the other fish have you ever heard of a publication somebody fail because they chose a niche that was just too small probably there's a lot of failures out there I mean it's the the old playing on the internet right with bullet holes in it like you you see what

1:26:51

succeeds and what doesn't I do think that grind is underrated like it's very it's it's very easy to get started you've probably been thinking about it for a long time you're like a band putting out its first album with songs you've been curating for years and years the great bands are the ones with the great second album and where there there's a there's a ability to generate consistently new and interesting sort of insights and points of you and it's interesting because I do think there's a bit where doing something like because I do it daily I think about it all the time and so my process of coming up with ideas is always running to a certain extent there's a bit where the way to not run out of stuff is to make more stuff which is sort of counterintuitive like creativity isn't a well that you just borrow from it's it's kind of constantly replenishing that's right I I I do think there is something to that um certainly

1:27:52

that gets back to the concepts we talked about earlier about having a view of the world and a system and you're sort of augmenting and building on that as opposed to trying to build a perfect edifice of like this is my castle of of Technology um no this is my sort of much more organic always changing always evolving always being different um sort of views of how things work lovely stuff well I got to thank you because I don't think this podcast would exist without without your work and some of the things we were talking about with the laws of the internet and it's because of your writing and your ideas that that this exists and thank you very much well thank you for having me yeah Winston

Writing Example (Winston Churchill) 1:28:27
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Church Hill wasn't just the prime minister of the United Kingdom that's what people know him for but he was also a prolific writer he wrote a novel two biographies Memoirs and of course as prime minister speeches he'd spent roughly an hour working on them for every minute that he spoke so if he spoke for eight minutes he'd spent eight hours in prep and yes I know he's controversial but man there's a lot to learn from his writing so what I'm going to do is I'm going to play you a short clip from a speech that he gave in in 1940 and then we're going to break it down together we shall fight on beaches we shall fight on the landing grounds we shall fight in the fields and in the streets we shall fight in the Hills we shall Never Surrender so let's break this down like a good battle plan the structure of church Hills writing here is simple and strategic a commander-in-chief can get their Squadron their unit on the same

1:29:22

page with repetition and that's what church is doing here there's no mistaking the core themes here what is he doing he's using the word fight four different times and then he talks about how the British military will fight in five different places they're going to fight on the beaches they're going to fight on the landing grounds in the fields in the streets in the Hills so you see all the buildup there but the entire paragraph is building up to these words right here we shall never surrender that is the main point at the end that's the climax that everything builds up to church show also uses style to get his point across too writers these days you sit in your fifth grade English class and you'll be told to only keep what's necessary cut the fluff get rid of the excess but Church Hill does the opposite here you'll notice that rhetorically the volume and the diversity of places mentioned it's

1:30:18

actually more important for him than the literal meaning of each place and Church Hill he could have just added emphasis by add living a bunch more places with the word fight so you'll see here he's got fight fight fight fight he's got all this fight but you know what he could do he could just add a whole row worth of stuff we shall fight in the cities we shall fight in the skies we shall fight in the forest we shall fight in the little Italian sandwich shops I'm just kidding right but he could have just added stuff and look at this the order of the locations is immaterial so he could take fight the skies and he could make beaches down here we'll move it up here then we'll take this and we'll go over here we're sort of like shuffling things around and this all works here's what matters all you need is right at the end you just need we shall Never Surrender this just needs to come at the end and if it does the

1:31:11

whole thing works now why is this it's because speech writing is different from the kind of writing that you usually get on paper it's this series of phrases these little phrases that are serving up to the pun punch line at the end right they're just building building building into we shall Never Surrender and you could arrange any of those little phrases you could take the first one make it the seventh you know rearrange them however you wanted in the paragraph it would still accomplish its purpose a sense of timing is important though adding all these little buildup phrases right here what are they doing they're increasing suspense right up until the point that you start losing people's interest and the more engage your audiences like when you're speech writing the more engage your audience is the more of these little buildup phrases you can add so yeah you could say the majority of what Church Hill is saying

1:32:00

here is fluff he could have taken all this and compressed it into one thing it looked like this we shall fight everywhere and we shall Never Surrender eight words could have had the same meaning but that wouldn't have been memorable we wouldn't be talking about it almost a century later instead Church Hill took 31 words and all of these words right here they raised the Stak of what he's saying they're giving his speech an element of suspense right when he wants it the most in this drum beat of repetition we shall fight we shall fight we shall fight we shall fight it's Paving the way for his eventual climax all of this is Paving way for what comes at the end we shall Never Surrender well that was fun who knew that arts and crafts class would come in so clutch huh well look I publish one of these writing examples every single week on writing examples.com and if you go to the site you enter email right at the

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top of the page I'll email you the latest one whenever it goes live