How to Write a High-Value Newsletter for Silicon Valley’s Finest | Byrne Hobart | How I Write

0:00

Writing a newsletter does  give you another cheat code.

0:03

So what's going on there?

0:03

You can choose a narrow enough topic that you will be the person who has  worked the hardest on explaining this one thing. You were up at what?

0:10

5:00 AM  every single day to write?

0:12

If there's a big story, you are not going to be  the first person to cover that story, but there's always demand for the last important piece on it.

0:17

Should companies be way weirder? In general, yes.

0:22

If I'm reading about a company  or an industry and I start mentally designing an elaborate German board game about it, then  I know I'm totally embedded in a topic.

0:31

I could write for a thousand years and  I would never have that happen to me.

0:37

My first question for you is how do  you actually track and begin to build ideas?

0:41

Is there a place where you are storing  ideas or how does that process actually work? Sure.

0:46

I've gone through a lot of different  systems over time, but usually the thing I default to is some form of, there is a big  file somewhere that has a long list of ideas.

0:57

Some of those ideas are literally one sentence  like look into company X, Y, Z.

0:57

Sometimes it's a question I want to answer.

1:02

Sometimes it starts  as that and slowly evolves into actual paragraphs and thoughts.

1:08

Points I want to make, things I  want to link to, things I should read later, things I have read and want to talk about.

1:12

And  some of those, they will just evolve into a post on their own.

1:17

And so the writing process  is go to the notes file, copy, paste, done.

1:25

In other cases, it's something where the  notes I have are just a starting point for a lot more research, and then I'm accumulating  research.

1:30

And so sometimes the research process can be that I start a post and I have a topic in  mind and just start accumulating little things I want to say and points I want to make and  notes and quotes from things I've read.

1:42

And then eventually you can hammer that into a  coherent final product.

1:47

That gets annoying sometimes because sometimes my viewpoint  changes halfway through, but that's also fun. Right. That's a good thing.

1:58

Now, when  I read your links email on Saturday, you link to articles, books.

2:02

Should I be looking  at that as Byrne is just interested in this or should I be looking at that as a leading  indicator of what you're going to be writing?

2:11

It is sometimes a leading indicator.

2:11

Especially on  the book side because there are some posts where I want to write it, but I realize I need a lot  more background information. And so I'll read a book.

2:22

If I'm writing about a company, if there's  a book about that company, I'll often read it.

2:26

Or if there's an industry I need to understand  better, I'll read some things in that industry.

2:31

So those can be a leading indicator.

2:31

But the  long reads that are just, here's a link to a long form article, that's just I like reading  long form articles.

2:35

It's just one of life's great pleasures is to settle down on the weekend  with your coffee and just linger over something.

2:46

And since I work from home, I guess I get that  pseudo weekend time fairly often.

2:46

And yeah, I can read some interesting articles hopefully.

2:53

You always have these fun ways of interpreting things.

2:58

And so when I read that, is that something  that comes to mind immediately or do you read a piece and instantly write the recommendation?

3:02

Because I see the recommendation as almost like this is my unique take on what's happened.

3:06

I try to make the newsletter value added.

3:06

If you want a list of interesting links, you can  go to Hacker News or you can go to the right subreddit and you find that.

3:16

I do want to build in  some commentary and sometimes there's a meta point to make about why did this get written versus  a point about the content itself.

3:23

So it's an important way to look at media is to always ask  why did this get written?

3:30

And if it is a deeply reported story, who was talking to the writer? Why were they talking?

3:36

I wrote a piece about this a while ago about business books and that  there are better business books about scandals than about successes for two reasons.

3:45

One is that  a scandal has an actual plot and it's basically Greek tragedy.

3:53

So you have hubris and then you  have this downfall and there's this aftermath and this person gets punished for thinking they  could do more than they could actually do or for their various mistakes, et cetera.

4:03

So it is more  of a narrative.

4:03

Whereas a success story is like this company used to be young and scrappy and now  they're a very large corporation with lots of vice presidents of whatever and their shareholders  are happy.

4:15

That's a good story for the world, not a super interesting story to  read relative to the alternative. So that's one piece.

4:23

But the other thing is when  a company fails, nobody at that company is busy making money. They're all unemployed.

4:29

So they  all have a lot of free time and they all want to say that whatever happened, it wasn't  their fault.

4:34

So if you read Enron books, you can basically read books like Smartest Guys  in the Room as every ex Enron employee trying to explain why it was some other part of Enron's  fault that Enron collapsed.

4:44

And some of them will probably be right.

4:49

I don't think every  single person at every fraudulent company was doing all fraud all the time, but you have to  consider who's talking to whom and who would have an incentive to talk and who wouldn't.

5:00

If  there's a boardroom coup, well, who on the board is talking to the media? What are they saying?

5:05

And sometimes when there's a scene in a business book or a news story, and you know there  were just not that many people in the room, then you can actually start to narrow down your  list of whose narrative is this based on who would be talking about this?

5:21

And sometimes it's like if  the story's really embarrassing ...

5:21

If there are two people who were involved in a conversation  and one of them comes off looking really badly at the end of that conversation, yeah, it's the  other person talking to the media.

5:31

Which again, doesn't mean they're lying, but it does  mean that you are getting the version of the story that is most flattering to them. Yeah.

5:39

I once heard somebody say something to the effect of when you first start reading an article  about something that you don't know much about, you retain 30 to 40% of whatever's being said.

5:49

The numbers here don't matter.

5:49

It's the meta point that does matter.

5:54

And then you begin to understand  an industry or a space better and you understand 100%.

6:00

What I thought was really interesting  is that if you're an expert on industry, you understand 150%.

6:04

And the meaning there is that  every single sentence, every single paragraph, you can then layer onto a tapestry of other  knowledge that you've built and then you can see through things.

6:16

You can see what's going  on at a much more deep and fundamental level. Sure.

6:20

I think that's a very accurate assessment.

6:20

I think the other way to get to over 100% understanding is that if you understand better  than the person who wrote the article why they were in a position to write it.

6:30

Why did someone  leak to them and not somebody else?

6:30

Why are they leaking now and not at some other time?

6:34

Then yeah,  you can get to slightly better understanding than them.

6:39

And of course, good journalists know that  everyone who's talking to them has a reason to talk to them, so they can make some adjustments  for that.

6:43

But depending on your context, you can sometimes make the adjustment a little better.

6:49

You mentioned something earlier about effort and how much is the correlation  for you between how hard you work on a piece and how much of a banger it becomes? I wish it were higher.

6:56

And this is something I've noticed with a lot of newsletter writers.

7:03

It's  a perennial complaint that our favorite pieces, the ones we work really hard on just don't do  that well. It's not always true.

7:06

There seems to be a correlation slight between the  length of a piece and how well it does. So longer better? Yes. Interesting. Wait.

7:17

That doesn't match up with  how people think about how society's changing right now so what's going on there?

7:22

The more you write about something, the more likely it is that you have actually  done the definitive take and that when people want to explain the topic to someone else  thoroughly, that's what they cite.

7:30

I think there is this game that people play  that you can play to an extent on, say when you're trying to get rankings on Reddit  or Hacker News or even get trending on Twitter, where if there's a big story, you are not going  to be the first person to cover that story.

7:44

It's going to be whoever broke the story or if  the story is a company announces something, a bunch of people will just immediately retweet  that or they'll tweet it with commentary.

7:52

It's very hard to be first, and it's very competitive  to be first.

7:56

It's random at this point over, whether it's someone at Insider or someone  at Bloomberg or someone at the Verge, someone will get it really, really early.

8:03

But when something big happens, there's always demand for the last important piece on it.

8:08

What  did this actually mean?

8:08

And that is a lot harder to define because it's not this one dimensional  competition of can you tweet it first?

8:16

And you see this with ...

8:22

There's a great profile of  Joe Weisenthal who was at Business Insider, now at Bloomberg, where it's talking about how  on jobs day, I think he has two tweets lined up in TweetDeck.

8:33

One for if jobs are better than  expected and one for if jobs are worse than expected, so all he has to do is alt tab and hit  enter. Yeah.

8:37

That's tough to compete on because it's one dimension.

8:42

But if you have two dimensions  of timing and quality, then you actually have a reasonable shot.

8:48

So that's something that I  aim to do.

8:48

And the success rate is probably higher than it would be for just being first to  tweet it, but is not even going to approach 50%.

9:01

So then when you have a post like the economics of  gas stations, which are like, how did that do so well?

9:05

Do you do retrospectives on that or do you  think what's going on there?

9:05

Or is it just like, oh, that's surprising, and you move on?

9:10

Honestly, a lot of it is the huh reaction because I think it's very hard to predict what it is that  people don't know but will find interesting.

9:16

And trying to fill those gaps in people's knowledge,  it's hard and it's also filling gaps in my own knowledge.

9:27

And since if I don't know something  ...

9:27

So the gas station one is another one where I'd been thinking about it and just thinking  about, well, how do they actually make money? Yeah. How do they make money?

9:36

Well, they make a lot of money from lotto tickets, cigarettes, snacks, stuff like that.

9:40

The  actual business of selling gas is just not where they make money.

9:46

They make money really on the  foot traffic.

9:46

And there are a lot of companies like this where their whole model is build this  bundle, and if you can do one thing well enough that people actually buy it and you can break even  on that thing, then you add one more thing and suddenly you have a really profitable business.

10:02

Is this a little bit like how you think about Diff Jobs? I see something similar.

10:07

It's like  a gas station come for the gas stay for the food and the lottery tickets.

10:11

Diff Jobs  is come for the ideas, get a better job. Yeah.

10:15

That is definitely how I think about it.

10:15

When I started the newsletter, it was just, I'm writing for fun and I'm going to email  people because not everyone uses RSS.

10:20

And then it became well writing the newsletter  in order to stay in the loop and find my next job.

10:31

And I started getting worried about  COVID in early 2020 and realized, well, I'm probably not going on very many job interviews  this year.

10:36

We probably just won't have a lot of human contact.

10:41

So I decided to make it a paid  newsletter instead just to get through.

10:41

And then it turned out that spring of 2020 was just  a phenomenal time to be selling content online.

10:51

I think a lot of it was just white collar workers  who previously had a commute.

10:51

So their time at home ends when the commute starts and then their  time at home begins again when the commute ends.

11:01

So if they start working when they would start  commuting instead of when they would get to the office, then they have this extra time and they're  probably going to fill it with something that is work adjacent, but not necessarily more work.

11:10

And newsletters that talk about the industry they're in really fit that niche well.

11:17

That's  the initial evolution.

11:17

Then I just started to notice after a while there're lots of really  interesting people reading this newsletter.

11:20

I was getting lots of really incisive comments from  people and noticed that some of these comments were from startup founders who were saying, "You  wrote this about the industry and you should also know this other thing," or, "That thesis makes  some sense, but we have this totally variant view and here's what it is."

11:38

And other comments  were from people who were not starting their own company but you could tell were just really smart,  thoughtful people who were very intellectually curious.

11:48

And so I did start connecting them.

11:48

That was a year and a half ago that I started doing that, and that's been going well and  is growing faster than the subscription part of the newsletter.

11:57

It has a different network  effect so if the number of subscribers in the newsletter roughly doubles, then probably  the value of that writing roughly doubles.

12:07

I'm writing for twice as big an audience, and if  they like it, then yeah, that's doubled.

12:07

But if the size of a network doubles, then the number of  connections in that network more than doubles.

12:12

It doesn't actually square, but it does more than  double.

12:19

And so you do have more opportunities to connect people as that network gets bigger.

12:25

How do you think about quality of people there?

12:30

Because I think one of the big things with the  The Diff is you have a smart median reader, so you want to grow your audience, but you  actually have almost diminishing returns, right?

12:40

Because if you don't have great readers in  the sense that these aren't the kinds of people who would want to work for the companies  that would pay The Diff to recruit them, then actually more people would take more of  your time, be more noise and stuff like that.

12:55

I think that kind of thing is very much an  emergent property of other stuff that I do.

12:55

Part of what keeps me motivated is it's a newsletter  that I would want to read and I want it to be the newsletter that if I were a reader rather than the  writer, it would be the first thing that I read when I was checking my email.

13:11

So it's going to end  up attracting people who share that curiosity and want to go deep on weird business and tech topics.

13:21

So in that sense, I don't really have to think that much directly about, okay, how do we make  sure that we're getting the best readers and not the worst readers?

13:33

There are going to be limits  to that.

13:33

If someone is smarter and works harder and writes a newsletter that is more focused  on a particular domain, then they're going to have smarter people within that domain.

13:45

But for  getting a smart general audience or audience of specialists with general interests, I think this  approach really works.

13:50

You can always worry about things having finite quantities when they don't  actually have a finite quantity.

13:56

You're probably not going to run out of smart potential readers.

14:02

Readers who I would like to hear back from when I write something that they have thoughts on.

14:08

It's  just I don't think it's actually going to happen.

14:12

One of the things I want to dive into is your  work ethic before COVID.

14:12

Because I think that this is one of the things I admire about your  story is you were working a full-time job and you were up at what?

14:23

5:00 AM every single  day to write.

14:23

And so tell me about that.

14:27

I go back and forth on what to say about schedule  because my schedule drifts a lot.

14:27

And one of the things is just when it's the new year, people tend  to take some time off and then reset.

14:34

So right now I'm getting up at five in the morning every  morning.

14:40

But usually my wake-up time drifts like half an hour later every season and then I reset  again.

14:45

But yeah, there have definitely been times when I was working full-time and writing on the  side when, yeah, I'd have to either get up super early or stay up pretty late.

14:58

The other thing  I found actually worked nicely was take notes on what I want to write on a physical piece of  paper and then at lunch go somewhere for lunch, set a half hour timer and let myself write  and eat and just do not use the internet.

15:18

And I found that I could actually write a decent  chunk of something worth writing and then going back and editing it and adding the links where  I just didn't have the links because I didn't have internet. That could work.

15:28

But now I use a  more sane strategy because writing inclusive of research is the main thing that I spend time  on.

15:35

So right now it's like get up at five-ish and check email, catch up on email, read news.

15:42

So I write most of the newsletter during the day and then send it the next morning.

15:50

And  there are two reasons for that.

15:50

One is way easier to edit something if you have slept.

15:54

The other reason is occasionally something will change about the world and you'll want to  make sure that you don't say the wrong thing or that you include some new note on an emerging  story.

16:04

One example of that is there was one time a couple of years ago where I was talking about  the economics of COVID and said something like, this will matter a whole lot less if there's  ever a vaccine.

16:17

And then the next morning first headline was vaccine tests successful.

16:21

And so  yeah, I had to quickly go in and change that.

16:28

How do you think about ...

16:28

You were talking to  me about how early on your retention wasn't that good, and so you felt like you were reading all  these things, but you didn't feel like you were actually retaining a lot of it, and that was  a lot of your motivation to start writing. Yeah.

16:43

If you read a lot of books, you can  have this depressing feeling of you look at a bookshelf point to a book you've read at  random, how many things can you actually say from that book?

16:52

At what length can you talk  about the contents of that book and what were the real takeaways?

16:57

And sometimes you'll point to  a book and it happens to be a life-changing book, and so you can talk about it for a very long time.

17:01

And then in other cases it's like I remember three specific things that happened in that book that  I didn't already know.

17:06

One of the things I found was just if I write about things as I'm reading  them, it's a lot easier to remember what was really salient.

17:14

And the other thing is it can  just drive me crazy to remember some fact that I know I read somewhere and be unable to track it  down.

17:19

It can be really gratifying to finally find one of these things.

17:26

And so as search engines  get better, a little more of that has happened.

17:32

There are other things where I know I've  read it, so I know I read somewhere that in the 1930s there were stocks that traded with  a negative price because when the IPO happened, they didn't sell everything upfront.

17:45

Instead of you buy the stock for $50, it's you buy it for $10 down and then $10 a year  for the next four years.

17:49

So if investors thought that this company would net destroy capital, and  if cash is very scarce, you'd actually have to pay someone to take the stock off your hands.

18:00

So I read that somewhere in high school.

18:00

I've never been able to track it down.

18:06

And every six  months I will Google and try to figure out some way to find this factoid and see if it was true.

18:12

And this happened with a couple of other things.

18:18

But writing it down helps with the retention.

18:18

It  also helps to make connections.

18:18

And so my version of spaced repetition is to think about what I'm  reading in the context of something else I've read.

18:31

So are there patterns that hold true?

18:31

Are  there patterns that break?

18:31

The more parallels you can draw and the more contrast you can find, then  the more you get out of the things you read.

18:37

So it does improve retention, improves comprehension. Yeah.

18:43

I always think of you as this implicit argument for the benefits of memorization.

18:48

I  think that there's a whole idea out there that memorization isn't really that important.

18:53

Everything's a Google search away.

18:53

You can always look something up.

18:56

But actually when you  have things that are really easy to grasp, your intellectual mobility is so much higher and so  you can connect things so much faster.

19:02

And sure, in theory you could go find what you need, but  when something's just right there versus I'm going to spend three days to find this, the  compounding delta in productivity is huge. Yeah.

19:19

There's a good blog post  about this from someone who had- The Pearl Leff one? Yes. Yeah.

19:23

I'm pretty sure the employees came from the IDF information warfare  type unit.

19:24

The piece talks about how they were used to working in secure environments where  they did not have access to Stack Overflow, so they memorized everything and that it turned out  to make them a lot more fluent in those concepts. So I do buy that.

19:39

I don't memorize things that  systematically.

19:39

So to the extent that I do memorize, it's probably just volume of information  ingested rather than doing an unusually good job.

19:53

So you have ingested more units of  information, you think you don't retain a higher percentage of those units.

19:57

I don't think I have a natural ability to retain that much more information.

20:02

And some  of it is reading a lot in the same domains and doing that repeatedly and trying to find  analogies between domains.

20:09

All of those things improve retention without requiring some  special skill or some special technique. Yeah.

20:20

Tell me about the story of one of your  first viral pieces, the one about 30 year mortgages.

20:24

Now that I'm saying it, I'm reminded of  a story.

20:24

Very first Rite of Passage session ever I mentioned this piece.

20:31

And I think that there  were like 36 people on the Zoom, and your wife was one of them and said, "No way.

20:37

Byrne Hobart  is my husband."

20:37

And it was just one of those, how is the world so small moments.

20:41

The world is a very small place. It really is.

20:46

I actually think that it's good to  ...

20:46

And this is something I've noticed.

20:46

I think it's just good to basically assume, especially  in matters of work, that you're basically in a high school cafeteria and everybody will hear  about everything because the world rewards people who are in niches so much, and at the  end of the day, the people who are talented in any given niche is basically small enough to be  in a group chat are slightly bigger than that. Yeah.

21:13

I think that's absolutely true, and that  if you're reading in a given topic and you're writing in that topic that after a while you are  very likely to either know a lot of the people or have mutual friends with a lot of these  people.

21:23

And then thinking about how to A, traverse that network, and B, how to make  sure that you're not actually missing some other talent cluster that you haven't heard  about is an interesting and difficult problem.

21:38

Sitting here as I listen, you see David  Foster Wallace right here.

21:38

How much do you think about cultivating your voice?

21:42

Because  when I think of DFW, I'm like, oh my goodness, singular voice.

21:47

Is that something that you  think a lot about in terms of the style, or are you just so focused on substance?

21:50

I only think about that if someone else is editing me and they take out a sentence that I like.

21:56

But  half the time I think, okay, this is probably a self-indulgent thing to say, so fine, let's cut  it.

21:59

And then half the time I think, no, this is just how I want it to sound.

22:03

But I haven't tried  to consciously cultivate a voice. I've written a lot.

22:12

And I think if you write, you do start  to develop some tricks and some little things that make it a little bit better than it otherwise  would be.

22:20

If everyone has a different collection of tricks and the tricks are not obvious ...

22:26

It's hard for me to read a great writer and look at a well-crafted sentence and just dissect  it and say, okay, I bet this sentence started out sounding clunky and maybe this part got split  up and this part got moved away and maybe this whole paragraph was restructured so this last  line could be really punchy.

22:44

If you don't see where it started.

22:48

It's hard to see how it got to  where it is.

22:48

But you can tell it's good, but you can also tell it's distinctive to that writer.

22:54

And I think everyone's going to vary in how much of a voice they actually have, and it's just hard  to force yourself to develop.

23:01

I think if you try to develop a voice that's really distinctive,  it will be very try hard and embarrassing at first.

23:14

And it may or may not become good.

23:14

But  I haven't read any David Foster Wallace novels.

23:24

I've read some of his essays.

23:24

If you go back to  the beginning, does it feel like he's really, really trying to be what he became or does  it feel like he was just being himself and if you read something from when he was 20,  he sounds like a 20-year-old who is good at this but is not what he would become? I do know this.

23:41

He was obsessed with the specificity of his writing.

23:47

He won't just mention  a tennis racket.

23:47

He'll mentioned a tennis racket from 1974 where the strings had this quality  about them.

23:57

This was the brand, this was the make, this was the year, this was the color.

24:03

And  at the University of Texas Library in town, they have all of his notes.

24:10

And I've actually  looked at the digital archives.

24:10

But you can see him writing on eBay listings and looking at the  descriptions and then pulling the description of the eBay listings into his actual writing.

24:21

And so  there's a lot of work that I know went into that that is certainly some kind of voice.

24:27

And I think  that Ben Cutatralle has my favorite line about David Foster Wallace.

24:32

Most writers, they look at  what's happening and they have an iPhone picture.

24:39

David Foster Wallace has a 13K resolution.

24:39

You can  zoom in all over the place. Three-dimensional.

24:39

And that is something that I'm sure he has cultivated.

24:46

And this why I can't read David Foster Wallace for a long time.

24:52

It hurts my brain because he's  interpreting too much.

24:52

It's also why I love him.

25:00

It can be fun to read very challenging people.

25:00

And especially authors who are willing to be overwhelming.

25:08

It's a useful exercise to read that.

25:08

It's also interesting to think about whether the writing process is actually a process of just  trying to get everything possible out onto the page, or if there's actually some conscious  cultivation of which details do we highlight and which do we omit?

25:25

So if he's living in  this world where tennis is the salient thing, then you obsess over tennis and you don't  necessarily notice if a particular person is tall or short or wears glasses or not.

25:37

It's  all just background.

25:37

So I think that's one way is that it can be done deliberately.

25:43

And then the  other way is it can just be this more instinctive thing where he is just deeply aligned with how his  character thinks about the world and his character happens to think that way.

25:55

And so it just doesn't  occur to him not to make those fine distinctions.

26:01

Have you ever seen his  interview with Charlie Rose? I haven't. Okay.

26:03

So David Foster Wallace is sitting there and it goes something to the effect  of this.

26:06

So he's sitting there and he's sweating.

26:11

And Charlie Rose realizes that something's going  on.

26:11

And the back and forth is something like, "Hey, calm down, it's going to be good."

26:18

And David  Foster Wallace just goes, "Do you realize how many people are going to see this?

26:24

There's going to be  millions of people who are watching me right now.

26:27

If I go like this on my face, all these people  are going to see this."

26:27

And so my read on David Foster Wallace is he was so self-conscious and  then also had this way of understanding how many people were seeing him and judging him and looking  at him, and he was running that loop in his head so intensely that he's like, what am I doing?

26:45

How  is this going to be interpreted by this person?

26:49

All these other people, that that just drove  him crazy.

26:49

And something about that cognitive awareness in him was far beyond most people.

26:54

I think that sounds like a reasonable assessment.

27:01

And I think the world a bounds in  trade-offs, and one of those trade-offs is if you are extremely aware of emotional states and  very aware of your own emotional state and very aware of other people's emotional states, you  can write some really interesting fiction.

27:12

But you still have that problem and- And you might go insane. Yeah.

27:21

And if the result of writing that fiction is  suddenly a whole lot more people are aware of you and they're thinking about you and talking about  you and you know it, then yeah, it can end up self-limiting to various degrees of drastic. Yeah.

27:30

One of my favorite ideas from you ever is smart people read.

27:37

And what I've added to  this is smart people read, your point, and smart and successful people read the most.

27:42

And  this is in contrast to video, which has become so common.

27:50

And we can talk about the benefits of  video later, but why did you write that piece?

27:55

I feel like there can be amazing documentaries  out there, there can be amazing video tutorials, but in general, it is just very hard to match the  written word for information density.

28:02

And it's very hard to match it for these affordances  like being able to backtrack a paragraph, backtrack a page, being able to control F, if you  have a digital document.

28:14

Being able to highlight and things like ...

28:18

All of this is so much easier  to do with the written word.

28:18

There's a different zoning out with reading rather than with video  where if you zone out with reading, you are fully immersed.

28:30

You will sometimes lose track of things.

28:30

And I think this happens to anyone who just reads for extended periods is you realize, I flipped  through three pages, I don't have any retention of this.

28:39

I just went off on some tangent based on  something the writer was saying, but my eyes were still moving, so I didn't notice. All the time. Yeah.

28:45

I'm glad I'm not the only one. Yeah.

28:48

It's a hazard of reading.

28:48

But when I read  about very successful people, a lot of their time is spent reading and a lot of their communication  ends up in the written word.

28:57

So Amazon has that famous setup of the six-page memo where it's six  pages with an asterisk because you can have many, many more pages of appendices and of data  tables and things like that, supporting charts, whatever.

29:16

A lot of their ideas are built  around we're going to write a concise, well-edited memo that has just been brutally  beaten into perfect shape such that it is extremely clear and direct what we are doing, why  we're doing it, what metric we're trying to fix, what is the metric of success, who is responsible  for what, such that there's no ambiguity, and it's just easier to do that with a page of text.

29:41

And so the standard story with Amazon when Bezos was there was everyone sits down at the table,  everyone reads the memo and they make their notes, decide what questions to ask.

29:53

And the meeting  doesn't start until everyone's done.

29:53

And Bezos is always the last one to finish, which I don't  think is because he's a slow reader naturally.

29:57

I think that he's some combination of one, being a  careful reader, two, just signaling to people like it's not a race.

30:08

Please don't skip what turns out  to be a crucial paragraph, and that if the memos are written very concisely and directly, there  isn't going to be anything you want to skip over.

30:18

And then if you go back to Microsoft, they had  lots of smart people.

30:18

There's actually a New Yorker article from years ago where the journalist  ...

30:22

I think it's written probably early '90s, where the journalist has started emailing Bill  Gates.

30:27

And he says that Bill Gates would send him these multi-page emails like a day after  getting the initial email.

30:32

And you realize that that is how Bill Gates was running Microsoft was  get questions and think through them thoroughly and then answer at length and be sure to have  lots of supporting information.

30:43

The nice thing about writing versus talking is you can go back  and you can change the order of things.

30:49

You can eliminate the extraneous things or put them in  footnotes. That's what I do.

30:55

You can figure out if there is something that needs to be emphasized  more or something that just needs to be cut out.

31:06

And I think especially if you are a tech CEO  emailing a journalist, think about what things you don't actually want to say, not because they  reflect poorly on you now, but because they will be damaging 10 years from now when your company  is bigger and more powerful and more threatening.

31:20

This is actually how a lot of companies get in  trouble, is that they start out super ambitious and they say the kinds of things that very  ambitious people say about world domination and crushing the competition and whatever.

31:29

And then  they stop saying that because you can't say we're going to crush the competition.

31:34

And in fact, a lot  of these companies will train people internally, don't use the term market share, don't talk about  competing in competition, focus on the customer.

31:43

Just don't put it in email, which of course  looks bad because now you have a PowerPoint saying don't say all these things- And you've literally said it. Yeah.

31:49

But they still have said those  things in older communications.

31:49

So that's often what comes back to bite them.

31:55

I want to give you a chance to give you a quick point on the tacit knowledge point with  reading, and then I want to get into what some of the other ways that companies do internal  writing are.

32:05

So I know you've worked with Stripe, and I want to hear what that landscape looks like  for business writing, comparing it to Amazon. Sure. Yeah.

32:16

The tacit knowledge point is ...

32:16

I'm a big champion of reading over video for just general information.

32:23

There are categories  of information where video is clearly obviously superior, and a lot of those are tacit  knowledge.

32:28

So in my case, the very common use case is building something for the kids that  I have purchased in a disassembled state and I need to actually build.

32:40

My shape rotation skills  are not quite up to par for some of this stuff.

32:46

And so it's a lot easier to just look at the  YouTube video, see what people do and rewatch, whatever the tricky weird part is where you hold  on this while stretching this, and then you push that button and then it just pops into existence. So it's good for that.

32:56

And I think that means that YouTube is really good for a lot of very practical  either home maintenance type skills or blue collar skills in general, where- The classic how to blank. Yes. Yes.

33:12

You would learn it from someone who  does it, either has had to do it ...

33:12

Has had to unclog a drain, or from someone who does it  for a living.

33:18

Now you can learn a fair amount of it from YouTube.

33:25

So I guess what that  amounts to is if you think that the US and the world will continue to get richer and that  will consume more services, we'll have more of these products that are produced by a small  group of people and then consume globally, you want to be a reader.

33:41

If you think the  future is actually a future where a lot of globalization unwinds and a lot of this stuff that  we implicitly outsource to the rest of the world, like buying ...

33:52

We buy cheap, fairly disposable  appliances and stuff because we could just replace them.

33:58

But if we were buying stuff that had to last  for 20 years, we'd have to learn how to fix it.

33:58

So if you're more pessimistic, then definitely be a  video person.

34:02

But yeah, if you're more optimistic about economic growth and about the current kind  of economic growth continuing, be a text person.

34:14

Let's talk about the different companies  and the landscape of memo writing. Yeah, sure.

34:19

I think a lot of it's hard to get  the flavor without being inside the company.

34:24

And some really interesting companies have not  quite gotten big enough that they've gotten sued and had all this stuff spill out or had some of  it leaked.

34:30

But what I think you can see is that there are some companies that are building  a references culture and then some that are building more of a live communications written  culture.

34:40

So someone like GitLab, they've been full remote since the beginning, and they have  this really cool wiki where it's basically all of their internal processes.

34:51

You can read all of  them.

34:51

And that stuff is pretty static.

34:51

And so it does make sense to have it as a reference.

34:58

It does  mean that the people who are doing those roles can be swapped in and out more efficiently.

35:04

So if  you need to add a customer support team in a new language that you didn't previously support, like  a new human spoken language you didn't support, you know roughly what the procedures are, you know  what some of the problems that can arise are, you know what the right team structure is, et cetera.

35:19

Or if your head of X leaves, hopefully there is extensive documentation on what the head of  X needs to do, and then the people who report to that person also have corresponding  documentation on what they should do.

35:30

So the new person can spend awhile getting  up speed, but they know roughly what to do and there are hopefully no loose ends.

35:39

So I think that's one version, and that can work well, especially in a company that has  to do asynchronous communication and that is remote and that expects some employee turnover.

35:49

And then the Microsoft-y and Amazonian model, that seems more about communication around  discrete decisions.

35:58

So it's actually less about, we're going to create reference  documentation that we will then look at, and that will be where the knowledge lives.

36:06

It's  more like we're going to think this through, and the place where the knowledge ultimately lives is  in the heads of people who are making decisions.

36:16

So we're actually loading a bunch of useful  data into RAM and then sending people forth to make decisions that partly reference that data  or reference those mental models.

36:21

So I think those are different ways.

36:26

The long-term storage versus  working memory models of writing.

36:26

Though the working memory model of writing does feel wasteful  because you spend a lot of time getting a draft into shape and then people read it and the better  it is, the more people just don't ever have to read it again.

36:45

They got the point and you were  right and so the thing gets done.

36:45

And then once the thing is actually in the process of getting  done, you have to go back and reference, okay, what are the performance indicators?

36:55

What are  the metrics we care about?

36:55

And are we actually hitting those or do we need to rethink those?

36:58

But you don't have to go through the arguments.

37:02

You're basically living out the argument  from a religious conversion experience.

37:06

So it feels wasteful in the sense that the  actual artifact that's left is just this husk that no longer matters once if it works.

37:11

But it's also the process of doing the writing is probably one of the more useful parts.

37:18

And  then you're transmitting a lot of that utility, a lot of the work that someone did to actually  figure out what point they're making and to think about all the possible counter arguments and  what the counter argument of that is, or if that counter argument actually needs to be addressed  and incorporated into the plan.

37:33

A lot of that work, it takes a lot of time, but it has to get  done to make good decisions, and so they did it. Yeah.

37:43

One of the things I love about having  a written culture and why I'm more and more excited about it, especially as the team grows, is  if we're in a meeting, conversational meeting and what ends up happening is quite political.

37:54

That  the boss says whatever, and then everybody just literally subconsciously goes around whatever the  boss is saying.

37:59

And so there's a huge hierarchy.

38:06

If you write a memo, that doesn't happen nearly as  much.

38:06

And what I love is at least people can know, if I look at a paragraph, I look at a section, I  have no idea who's written it.

38:12

And so I do think that in that sense, there is a more meritocratic  way that ideas bubble up and decisions get made. Yeah.

38:25

I think two companies that have tried to  enforce that ...

38:25

And it's always a question of if a company has a reputation for a particular  corporate culture, is it that they have that corporate culture?

38:34

Is it that's actually an  understatement, they're even weirder than you realize, or is it that they're a little bit- Should companies be way weirder?

38:42

In general, yes, if they're small and then they  just have to get more normal as they scale, unfortunately.

38:50

There's nothing wrong with running  the company you'd love to work for and keeping headcount capped at whatever is a reasonable way  to cap it such that you actually get the culture you like.

39:01

Because when you have a job or have a  company, you are determining how you spend a big chunk of your waking hours. No kidding. Yeah.

39:08

Why sacrifice a lot of your lifestyle gains  to make more money that you just don't have time to enjoy?

39:12

But go back to the memo culture and the  question of jumping through the org chart to make points.

39:24

PRE-IPO, PayPal had this reputation, and  Bridgewater had, and to an extent still has this reputation of being very flat and very open  to criticism from low level employees to top level employees.

39:38

So I think both companies have  a story of an entry level-ish employee getting a company-wide memo from the CEO and replying  to the effect of, this is stupid, here's why.

39:51

And in both cases, the moral of the story is  this was actually rewarded and encouraged.

39:57

I think in one of those cases, it was like  the person accidentally hit reply all instead of just reply and thought they were going to get  fired, but actually were praised.

40:02

And one of the things to navigate there is actually a pretty  good chance that the CEO has a better idea of how to run the company than a new employee.

40:14

So there's actually probably not a great hit rate on those kinds of criticisms.

40:19

On the  other hand, you really don't want to be in a position where the CEO is insulated from all  of the useful information on what they're doing wrong because everyone's too intimidated to speak  up.

40:29

And different companies and organizations and even societies have different ways of trying to  transmit information from the people on the ground who actually know what's going on to people  who have broader but shallower knowledge and have the legitimacy to make important decisions. Yeah.

40:45

I always think of writing as a technology that climbs organizational ladders probably  better than other mediums because it's so well compressed.

40:56

And also the people at the top,  they need highly compressed information because they're so void of time, and so writing's a good  way to do that.

41:01

Tell me about this idea of how many different newsletter writers have actually  gone on to be fairly economically successful.

41:14

We can talk about Shelby Davis, Jim Cramer, Bill  Gurley, Warren Buffett. Who else comes to mind? Yeah.

41:19

So I think part of the way this works is  you stretch the definition of newsletter writer a lot.

41:24

But I think Bridgewater is actually  a good example where Ray Dalio did start out by sending his thoughts and he would send out his  thoughts on interest rates or commodities or what the market is doing, and subscribers paid for  that.

41:34

And then eventually people just told him, please, instead of sending us this memo that the  head of our pension fund immediately reads and just trades based on, why don't you just manage  some money for us instead?

41:43

And so in that case, Bridgewater went from selling just access  to ideas, to charging a fee on assets under management.

41:54

Bill Gurley has an interesting  career background where he started as an equity researcher and then had a separate newsletter,  which I think was originally distributed by fax.

42:04

But it was just his thoughts on the industry,  a little bit more informal than your standard 40-page research paper with lots of charts  and graphs, but also just a lot more direct. And that helped him out.

42:15

There was also Sevin  Rosen was an early VC fund, 80s VC fund.

42:15

They were also newsletter turned venture fund.

42:22

Charles  Schwab wrote a newsletter briefly before starting Charles Schwab. So yeah.

42:29

People have done that  transition.

42:29

I think part of it is that newsletters have very ...

42:35

They have broad reach, they have  high surface area relative to other businesses.

42:39

You can get some attention and build some branding  in front of a lot of people without having a huge business behind it.

42:47

So you can almost look at a  newsletter as a brand name and a customer list in search of another business.

42:52

And in a lot of  cases, if it's a newsletter, the subscribers are this potential network of people.

42:59

And if you think  about a network of people who are interested in, say, finance as a lot of these newsletters are  about finance, some of them have money and are looking for places to invest it.

43:09

Some of them  need money in order to invest it productively in their own business.

43:13

So connecting those  two is the really natural thing to do.

43:17

So I think that over time there will be an  increasing number of newsletters that started out on Substack and they end up running a  fund that obviously has happened and will continue to happen.

43:27

I think some of them will  end up doing slightly more esoteric stuff, but also basically connecting different sides of  the network that they've built.

43:32

I think another part of it is that if you are running some kind  of investment business, you are allocating capital and going back to the memo writing culture,  you have to think clearly about what it is, what your decision is, why it works.

43:47

And writing  investment memos without being able to write checks can get you to a position where you can  write the memo and then write the check too.

43:58

If we walked into a university, you got 40 kids  right now, I give you an hour to teach a class, what do you teach it on? It's a writing class. It's a writing class.

44:04

Teaching a class on how to identify a topic that is at the intersection  of some Venn diagram of things that you would actually be reasonable for you to care about  or reasonable for you to write about.

44:18

How to dive really deep in research and then  how to edit it into practical shape.

44:22

It's probably a lot for a one-hour class,  it might be more of a semester thing.

44:32

So how do you structure it?

44:32

How do you think about this?

44:34

So I think one thing to do is to start listing  out separate unusual interests that you have and then start listing out parallels between  them or places where they actually intersect in the real world.

44:46

So if you are interested  in software and you're interested in business, then obviously software companies are a pretty  direct place to look at.

44:52

Maybe you're interested in ... I don't know.

44:59

You're interested in  probability and you're interested in poetry.

45:04

Maybe there's something interesting to say about  just ... I don't know.

45:04

What are the things that determine whether an undiscovered poet will  become a well-known and well-respected poet?

45:14

I don't know very much about poetry and know  a little bit about probability so I'm not the right person to figure out those intersections.

45:20

But I think someone who has this set of seemingly disparate interests, often those interests are a  reflection of a smaller set of their core traits.

45:32

And if they figure out why it is that they find  these multiple things appealing and what connects those things, then they can start to find ...

45:36

They  can start to either one, work on the canonical, here's why this is just that piece.

45:42

So  this is like Paul Graham's heres why people who write software are just painters.

45:47

And he says in that piece that it's not like that's the perfect analogy.

45:52

He says that people  who write software are a lot more similar to architects than they're to painters, but he's  done painting and hasn't done architecture, so he's going to write what he knows.

46:02

So I think  finding those deeper connections and then finding just the more obvious connections of where in the  real world does this topic bump into this other topic or what is the mediating layer between  those two topics can be just interesting way to explore ideas and explore why you find these  ideas compelling too.

46:21

It's very hard to be the best writer on one topic.

46:30

But if you take all  the sets of topics where that's too competitive and then just start randomly saying best on  X and Y, then you will eventually run into something where there is no competition.

46:42

90% of  the time it's because there are no good analogies, and it's stupid because you're just choosing it  random.

46:47

But at some point you may actually find something where you think there are commonalities,  nobody's explored them yet, and you could probably say something new and insightful. Yeah.

46:54

One of the things that I noticed when I talk to Write of Passage students is how few of  them know how to look at their own experiences.

47:05

And first of all, even recognize the wisdom  in them in the first place and second of all, basically make a value judgment of what things are  going to be interesting to other people and what things are going to be less interesting to other  people.

47:18

And this is something I struggled a lot with when I started to write.

47:23

I just couldn't  write about myself.

47:23

It was this weird thing and I had to work through that.

47:28

But I think that  what helps me a lot is if I'm out with a friend, we're at the bar, we're hanging out, going on a  walk, they'll say, oh, that's really interesting.

47:40

And they'll help me validate whatever that  experience is.

47:40

And then often I can take some experience and I can use that as the basis for  my piece, and I can say, what's the punchline? What's the takeaway?

47:52

What can I connect that  to?

47:52

And over time, that's become a better and better way to find writing ideas.

47:58

And basically  anybody over 40 who's halfway successful is going to have a bunch of personal experience that they  can draw from, but they just aren't seeing it. Yeah.

48:11

I think one of the other takeaways is find  friends like that friend who can tell you, wow, this is actually really interesting.

48:15

That is  a trait that it's useful to cultivate among friends.

48:19

Because everyone, I think overestimates  ...

48:19

We overestimate how similar we are to people in some ways and how different we are in  other ways.

48:26

And part of that similarity, overestimation is just you've actually lived  your life.

48:29

It's a thing that's happened to you.

48:36

It could look really improbable to someone else,  but of course it happened with probability one.

48:40

So to you, a lot of stuff that actually would  look surprising or like, wow, you had a lucky break and it's amazing you were able to take  advantage of it that way or You must've worked really hard on X.

48:51

To you it's just stuff you did.

48:51

And it can be a little bit too easy to miss how someone else's life would've gone.

49:00

And I think  turning to the wisdom point, I guess one of the ways to think about wisdom, one of the intuition  pumps there is just asking someone of the big decisions they made in their life, which of them  would they make exactly the same way today?

49:09

Which of them would they make differently?

49:13

How much of  that is new information you got and how much of that is just knowing what you knew then you would  actually do something totally different?

49:18

Because I think for a lot of people, either the answer is, I  would have gone to a different school, moved to a different city, married someone, or not married  them, or whatever it may be, some of them will have answers like that.

49:34

And then for other people,  if the answer is no, I like my life.

49:34

I wouldn't touch anything because it's actually great.

49:40

That  is its own wisdom because at the time that you're making those decisions, you don't actually feel  like I'm making the decisions that's going to make me a life so good that I would do anything to  prevent a change to this status quo.

49:48

So in a sense that that's its own wisdom.

49:55

Not world transforming  wisdom.

49:55

A very mellow sort, but it's there. Yeah. I like this line.

50:03

Probably 10% of my  topic in conclusion sentences are things I type up wearing only a towel because I wrote  them in the shower. Talk to me about that. Yeah.

50:13

I think it's a common thing that you can  work an idea, actively work on it, and you can work on a piece of writing or a piece of software  or an investment thesis or whatever.

50:20

But if you're working hard enough on it such that a lot of  the ideas are floating around in your head, you haven't had time, your brain hasn't had  time to defragment and put them back in storage, so they're still there, but if you leave them  alone for a while and go do something else, you can't help but have more stuff occur to  you.

50:41

So I do have that sensation a lot. Yeah.

50:48

Taking a break in the shower or working out  or walking or getting the kids ready in the morning where I'll realize that I'm still  working on something in the background, and then when I get back to writing, I know what  I'm starting with, what I'm concluding with, or at least know something new and important to add.

51:07

And I think a lot of people try to engineer that into their life, but you need to get the right  level of distraction.

51:13

So I don't think it really works to go from, I'm writing for a while to, I'm  going to take a break to answer emails and then I'm going to go back to writing.

51:24

The email thing  is just too close and I think it's just taking one set of text-based information out of your head  and replacing with another set of text-based information so you just don't have the space for  these idea collisions.

51:33

But I do think that if you don't know how to start a piece or don't know how  to end a piece, probably taking a walk is better than trying to write 10 increasingly frustrated  topic sentences and rejecting all of them.

51:49

This is one of the things that is really  surprising to me about writing is how when you're in a piece ...

51:55

What in a piece, there's  something that happens where you're just inside the piece.

52:00

The piece, it's like a surround sound  effect that you are existing inside of.

52:00

And I was speaking to a friend's mom ...

52:06

This was four  or five years ago.

52:06

And she was really depressed and to work through that depression, she started  writing a poem every single day.

52:14

And she looked at me straight in the eye and she said, yeah,  I wake up every single morning and I have the whole poem written at this point.

52:23

And it's like  this background process that happens in her head.

52:27

She doesn't even think about it.

52:27

And that's just  like you in the shower.

52:27

It's like somehow these things click into place.

52:31

I remember Ben Thompson  saying something to the effect of, I have literal sentences that are actually written and I just sit  down on my computer, I write them, they're there, and then other things morph around that. Yeah.

52:43

I've definitely had that sensation.

52:49

I think on the idea of being totally embedded in  a topic, for me, the two indicators of that are one dreams about it that is very good sign that  you're spending probably about the limit of your attention that day on that one thing.

53:00

And the  other one is if I'm reading about a company or an industry and I start mentally designing  an elaborate German board game about it, then I know I'm getting to the point that  I know what the moving pieces are and you can abstract it out and think about what  strategy looks like in that environment.

53:20

Why do you think you're so good at that?

53:20

I could write for a thousand years and I would never have that happen to me.

53:24

I don't know how good I am at that per se versus just spending a lot of time on it.

53:32

I think that's the cheat code at this point is I've been doing this full time for three  years and it's what I do with my time.

53:37

And so over time it's gotten a little bit easier to  do things like figure out if this company's worth writing at length about or if it's probably  not worth the spending many hours of research. What does worth mean?

53:53

How do you quantify that?

53:53

Is will I write a newsletter issue that I'm proud of?

53:58

And if you can go from you have a 50 50 shot  of writing something you're proud of to a 90% shot of writing something you're proud of, then  your output goes way up relative to the amount of research you do.

54:08

And since in my experience, idea  count is partly a function of output, that means the next round of ideas is a lot easier to get.

54:16

So a lot of this stuff just compounds over time. And I think the more ...

54:21

If you write about some  really, really object level stuff, like here's a profile of this one company, like the bowling  company you mentioned, or gas stations, then you'll often start to see some more generalized  mental models that you can then write about on their own.

54:38

And then you write about the model and  then you look at the next time you see an object level company that seems like it should be an  instance of the model and it's not, then you have an interesting company to write about.

54:47

You write  about why does this company not follow this rule?

54:52

So if I read about a gas station that just didn't  sell candy and didn't sell cigarettes and didn't sell anything, that would be a really interesting  company to figure out because I have no idea how that business would work.

55:02

On the other hand, you  can look at ...

55:02

Like some companies have started doing gas specifically to get the foot traffic.

55:07

And then companies that are doing EV chargers, like the EV charging is really, really good for  any business where it takes 30 minutes to consume the product.

55:19

So Starbucks is going to be a big  part of the EV rollout because you can charge your car, drink coffee, and then when you're done  drinking coffee and maybe lingering over either a snack you bought at a markup or ... I don't know.

55:30

Even a physical newspaper, if you're that kind person that you bought on a markup.

55:34

They generate  revenue from that traffic so they'll do it.

55:39

But looking at the specific companies, figuring  out what the broad lessons are and then looking at whether or not those lessons fit somewhere else  is just another thing with compounding returns.

55:48

Titles choose and before, choose  them after do they matter? Titles often matter.

55:52

I feel like that is  an area that I could spend more time on, but I don't know how to do better titles.

55:57

I think  some of the titles, I luck into something good. Like Back That SAAS Up.

56:04

Well, that was a friend of mine. I love that story. I think that's so funny.

56:09

He managed to work into a research report on Microsoft's move to the cloud.

56:14

This was like  five years ago.

56:14

He wrote Back That -AAS Up.

56:14

Yeah, I was proud of him. He was proud of himself.

56:24

Lots of high-fives were exchanged.

56:24

You don't always get that lucky.

56:31

And part of the fun of  that is obviously getting it past the editors.

56:35

And I don't really have editors, so.

56:35

I work  with someone, he does edit the newsletter in the morning, but I don't have editors who are  limiting what I can do.

56:41

I have people who will suggest improvements and do improve the essays.

56:46

In terms of coming up with titles, I don't know.

56:53

Sometimes a title will just work.

56:53

Sometimes just  a very straightforward title.

56:53

If I'm writing about a company and I don't know what else to say,  the title will just be understanding X, Y, Z.

57:04

Understanding Jane Street, understanding Palantir,  whatever.

57:04

Sometimes there will be some theme in the article that I can pull out.

57:09

Sometimes I will  write the title in advance, think that I know what the theme is and then look at the title, look at  what I wrote and realize the title has nothing to do with the content.

57:16

It's something that made it  into a footnote and the footnote got deleted but doesn't actually fit with anything.

57:23

It feels like  in a more Twitter centric world, you actually want to optimize for either sentences people will copy  and then quote into their tweet or paragraphs they will screenshot and then link to.

57:37

So maybe the  headlines actually matter less than they used to.

57:43

They still matter for search, but they don't  matter that much.

57:43

They don't matter as much as they used to for newsletters, in my view.

57:47

Where's your writing The weakest?

57:51

It is very hard to figure out how much to do and  it's very, very hard to deal with the issue of, I've written a bit about this topic, I  realize there's a whole lot more to write, but I actually want to publish something today.

58:04

So one of the tricks on that is you just change the title to part one.

58:10

You just add part one at  the end of the title and then publish the rest the next day.

58:15

But it can be very hard to figure  out, am I giving this way more attention than it deserves or not nearly enough attention?

58:22

It still  gets to the point where it's satisfactory, but I feel like there's room to improve there.

58:27

I think  another thing is just I think there are limits to how much author voice is really appealing to  people, especially if the author is not an amazing writer.

58:39

So you want the really good people to  be maximally and let them do their thing.

58:39

But if someone is not just this amazing craftsperson of  prose, then making them be more straightforward.

58:55

So making me be more straightforward  in my writing is probably a good thing.

58:59

When I read your writing, what you trade is  probably a lack of super distilled compression for here is a bunch of different insights from  paragraph to paragraph.

59:05

Each individual paragraph is going to give you a different way of thinking  about things.

59:10

Whereas other writers will have, here's one phrase and then I'm going to  unpack that the entire time.

59:15

You're not like a memer as much as like a, hey, here's a  machine gun, a pop rocks of different ideas.

59:27

Part of what I benefit from in this case is  that there's just so much writing about tech and finance that I can skip a lot of the preliminaries  that would otherwise be necessary.

59:32

So I don't have to explain to people what AWS is.

59:39

I could just  go right into writing about cloud computing and people will know the context.

59:45

Whereas if  I were writing about some other industry, but also for a general audience and I've had  this happen.

59:50

I do have to walk through how does this actually work?

59:55

So I wrote about liquid  natural gas a while back and should revisit it at some point.

1:00:01

It's a complicated, amazing industry  with a surprisingly long history of people trying to compress natural gas and then ship it long  distances.

1:00:06

But it's also something where I had to balance between one, how much technical  explanation do people have to know?

1:00:12

Two, if I do explain it in great technical  depth, am I more likely to be informing people or more likely to get an angry email  from someone who's been in the LNG business for 30 years and reads my newsletter and  says, you have no idea how this stuff works.

1:00:29

So those trade-offs get a lot starker in  industries that get less media coverage and finance and tech just get a lot of media  coverage in broadly accessible media.

1:00:34

There's plenty of media coverage of niche industries  in trade publications for those industries, but people just don't have the same context.

1:00:45

And  that gets it to another thing that is always this question about audiences of how much stuff is  actually obvious to people, how much stuff is new and insightful.

1:00:55

And it's really hard to tell  because something can be almost to the point of a cliche within an industry and then have no one  outside the industry has any awareness of that.

1:01:07

And you don't want to be like, hey, I invented  this great insightful thing when it's actually a cliche that everyone in the industry says.

1:01:11

I  think my bias would be assume that there are some people for whom it's new information and that even  people for whom it's old information, if you can elaborate on it more and get them just more of  a sense of what's going on, then it's valuable. Yeah.

1:01:31

One of the things that ...

1:01:31

And I'm going  to turn this question back on you, is one of the things I think a lot about is my social group.

1:01:35

Where a lot of times I'll find if I consume a lot of information, it's like a river that is totally  still and it becomes murky.

1:01:41

I can't really see my own mind.

1:01:47

Whereas what I need is much more of a  river stream with a constant flow, and then now I can see the bottom of the river.

1:01:53

And what I  need to do is just talk about ideas.

1:01:53

I think of conversations as an algorithm for randomness.

1:01:58

I always look back at conversations and say, oh wow, I've never had that thought before.

1:02:04

And I get the randomness plus the feedback, which allows me to come up with ideas.

1:02:08

And  then there's something about the back and forth of conversation where you could build on  something.

1:02:12

And so I'm super conscious about my social group and how do you think about that?

1:02:17

How do you think about the people you surround yourself with?

1:02:22

Do you try to intentionally create  interesting conversations?

1:02:22

Surely you optimize for interestingness at some level, so what do you do? Yeah.

1:02:27

So writing a newsletter does give you another cheat code, which is people who know  the topic will get the newsletter forwarded to them or they're already readers. They will  respond.

1:02:40

They'll give you useful feedback.

1:02:40

And it's generally they will have a lot more context  than you about why a decision was made or why something works or why it doesn't work.

1:02:49

They  will also just have more broad context about the question you're trying to answer.

1:02:55

So I  find that really valuable.

1:02:55

I think that in talking to people and trying to test out ideas,  trying to get what is the case against this is really effective.

1:03:06

So finding people who are less  likely to tell you that all your ideas are great is good.

1:03:11

And other than that, I think going  for breadth is a really good idea here because you really don't know what other people know  that you don't know because you don't know it. So I do try to ...

1:03:21

I try to stretch the content of  the newsletter a little bit and talk about things I'm less certain about specifically so that I  can hear from people who will help me refine those ideas and get better at them.

1:03:32

Other than  that, I'm just personally not that extroverted, so I'm just not in the business of really  crafting and refining my social network.

1:03:47

People ping me more than I pinging them.

1:03:47

I  guess I've done it indirectly by writing, but that's part of why I write is that it is  good to talk to people.

1:03:53

It's good to talk to people you wouldn't otherwise encounter, and one  way to do that is for them to find the writing. Yeah.

1:04:03

Let's close on a conversation about  work ethic.

1:04:03

You at one point said to yourself, I'm going to make sure that if I am in a  domain, no one's going to beat me because they worked so much harder than I did.

1:04:16

And I  really admire that.

1:04:16

I think that you've written before that it's only at the extreme tales that  talent becomes the differentiator and basically everywhere towards where 0.

1:04:27

00 on the graph  actually it's effort that really pays off.

1:04:27

And so let's talk about effort.

1:04:33

We'll talk about the  Protestant ethic and we'll see where we end up. Yeah. So that is true.

1:04:38

One of the takeaways from  the whole, I don't want to be outworked by someone who I think is just not ...

1:04:45

I think I could do a  better job if I worked as hard.

1:04:45

There's a limited amount of time so the first takeaway from that  is there are not going to be 10 things you're really great at.

1:04:57

You should probably pick one.

1:04:57

I  think another caveat on that is family.

1:04:57

I don't want to be really, really successful because I  completely ignored my wife and kids and they don't know who I am or something.

1:05:10

You can take that  too far.

1:05:10

But I think within those domains, yes, picking something where you think that you can  plausibly work hard and be among the best at it, or if someone is better than you, it's because  they were going to be better than you pretty much no matter what I think is a good thing to do.

1:05:25

I think you can treat that on a macro scale, but on a micro scale, it's actually in some ways  more useful because you can say that for a given topic, you can choose a narrow enough topic that  you will be the person who has worked the hardest on explaining this one thing.

1:05:44

If you're  sufficiently narrow, you can just do that. Like Caro and Lyndon B. Johnson. Yeah. Yeah.

1:05:49

He chose a guy with a big personality.

1:05:55

I actually finished  Master of the Senate last night, literally. Oh, nice.

1:05:58

That's a funny coincidence. Yeah.

1:05:58

He definitely went all- What did he take from Caro's  writing? That's a good tangent.

1:06:06

There's this funny thing where Caro keeps  quoting LBJ's line from when he was coaching a debate team.

1:06:12

LBJ would always tell them, if  you do everything, you will win. And LBJ would do that.

1:06:18

He would do everything, go all out.

1:06:18

People would say things like, I didn't think it was possible for someone to work that hard  and just pulls at every stop and gets it done, whether it's winning an election or stealing an  election or getting a civil rights bill passed, or getting a guy who is unfriendly to the natural gas  industry, not nominated for a position that allows him to bring that natural gas.

1:06:36

He went all out and  really made things happen, and Caro obviously does that too.

1:06:42

He moved to different places just  to be close to people who were close to LPJ.

1:06:48

I think he lived in the hill  country in Texas for two years. Yeah.

1:06:51

So he got to know these people.

1:06:51

When he  goes into the first person or first person-ish and talks about ...

1:06:57

I guess he doesn't go first  person.

1:06:57

When he talks about his interviews with people in line in the text, which is an  interesting stylistic decision, he will sometimes make it clear that this person was talking to  him because they were developing dementia and that had they known better and been a little  bit sharper, he would not have been able to get certain information out of them.

1:07:18

In other cases,  he makes it clear that this person waited until LBJ was definitely dead and only then was willing  to talk to him about what Johnson was like.

1:07:29

But yeah, I think that series is a testament to  extreme work ethic.

1:07:29

I do try to work fairly hard.

1:07:36

I try to read pretty thoroughly about the topics  that I'm writing about.

1:07:36

But I think it's very hard to talk about work ethic and actually compare  your efforts to anybody else for two reasons.

1:07:51

I think one is to the Protestant ethic point,  you're either in this cultural norm of you always brag about how hard you worked or you have this  more renaissance courtier norm of you don't brag, but you indicate very strongly that you did  not have to work hard at all to achieve this amazing thing.

1:08:08

And you don't know if the person  you're talking to, you don't know which of those camps they're in.

1:08:12

And you can imagine two people  who put exactly the same amount of effort into something and one of them just always sounds  exhausted and is talking about how agonizing it is, and the other one says it was easy and  they're doing the same thing. So that's one piece.

1:08:26

I think the other piece is just subjectively, I  don't know whether working hard or putting effort into something feels like this mental struggle or  if it feels like this is a very easy next thing to do.

1:08:38

Because you'd have to assume that people ... I  don't know.

1:08:38

People who are ultra-marathon runners, they're obviously trying hard, but they are  probably wired such that they don't have to exert as much mental energy to keep going after the 20th  mile compared to the average person.

1:08:51

So there's this question of how much harder are they trying  versus how much harder do they have to try? And you will never know.

1:09:02

No one will ever know, and  you will never know if your internal struggles of whatever kind are more severe than somebody else's  or less severe than somebody else's.

1:09:07

You just know that everybody has some kind of struggle.

1:09:12

So that's how I frame the effort discussion.

1:09:20

And I think that especially for someone who's  a knowledge worker, a lot of the work is either reading things people have typed or typing things  into a computer.

1:09:24

There's this long ouroboros of keyboards and screens and it keeps feeding back  on itself.

1:09:33

The big thing with maximizing output is just avoiding distractions.

1:09:40

And one of the  ways I think about it is Twitter is not going to be any less addictive a year from now, and  social media won't be any less addictive and the games won't be any less fun.

1:09:51

That stuff is  always getting better.

1:09:51

It's somebody's job to make that distracting, such that you don't spend  an incremental 15 minutes on work when you could spend it on something else.

1:10:00

So finding ways  to resist that and ways to plan out your day. What do you do?

1:10:05

Part of what I try to do is just block out my day into times when I have calls and you  have to be fairly focused for those, or times when I'm definitely doing deep research.

1:10:13

But when I  look at the rest of my schedule, I realize I can't mess around because I will literally run out of  time.

1:10:18

It will be 4:00 PM and there's nothing else I will get done that day until eight that isn't  already spoken for on the calendar.

1:10:23

It's either I have other calls and meetings, or I have emails  that have to get sent by the end of the day, or kids are home and I want to spend time with them.

1:10:34

There is no other time until the end of the day, and if you get up early, the end of the day is  not like this endless expanse the way it was when I was 20 where it's like, wow, it's 8:00  PM, I have another six hours to do whatever I want.

1:10:49

It's like, no, it's eight.

1:10:49

I'm very tired  and I'm going to read a book and go to sleep.

1:10:56

At this point, that's my strategy but I've  noticed that the distractions keep evolving, they keep getting better.

1:11:00

And so the strategies  have to continue evolving too.

1:11:00

But being in a field where I get daily metrics on how many people  read it, I get direct feedback from people saying, this is brilliant or this is stupid.

1:11:14

Often the volume of that feedback is more predictable than the direction.

1:11:19

So if I get  five comments from people praising something, I will probably get five comments from people  hating on it.

1:11:24

And if I get no comments and no comments it's very rarely on sided.

1:11:28

I really  don't know why that is, but it's true.

1:11:35

So I get a lot of feedback and that's actually  very motivating.

1:11:35

Just knowing that the next piece is either going to go out to slightly  more paying subscribers or slightly fewer, and it's going to be read by either slightly more  people or slightly fewer.

1:11:45

And it's also building this big corpus of things I've written that I  can feel good about, that I will continue to reference and continue to think about.

1:11:55

I know that  over time it's very hard to predict what writing will influence who and in what way?

1:12:02

But if you  write enough and you have a big enough audience, at some point you will hear from people who will  say, I really liked that thing you said about X and what my mental response is I do not remember  saying that, it's probably somebody else.

1:12:15

And then I'll google it and realize, I did say it, I  just forgot about it.

1:12:19

That does happen, and that's extremely gratifying.

1:12:24

Writing something that  even very incrementally changed someone's life, but that you don't actually remember writing  is a really surreal feeling, but a good one.

1:12:34

Byrne, thank you very much. It's a pleasure.