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When I struggle with writing, it's a signal to stop writing.
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It's worth finding a flow because then you can ride that.
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Sometimes I write and I get a little bit contrived and it's because I made the bar so high.
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What is it about writing it down that makes it have to be more perfect than saying it out loud? Right. Right. Right.
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Why do you think that there's so much bad business writing?
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Everyone's pumping out content.
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I don't like the word content at all. It's communication.
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Every team lead it has to write what's called a heartbeat summarizing all the work their team did over the last 6 weeks.
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It's searchable, transferable, easy to access.
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I don't think enough companies do it. Can I stop there even? Go for it. Let's break this down.
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When I think of entrepreneurs who can also write, Jason Fried, today's guest, is the very first person who comes to mind.
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He's written four books, more than a thousand blog posts, done a bunch of interviews, and he is a master in the art of communication.
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Most of the episode is focused on prose, his long-form writing, how he's written his books and his articles, but we also got into the mechanics of how he thinks about titles and copywriting.
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But his single favorite thing to do, and my favorite part of this interview, was when we went into the founder letters.
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Where what he does whenever he launches a product is he writes a letter.
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And what we did was we broke down two of them.
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How does he think about writing?
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How does he think about storytelling?
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How does he think about poetry and word choice? So let's get into it.
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Here's my conversation with Jason Fried.
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Jason, I want to start with uh a really quick quote that you have, which is don't write, communicate.
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And the thing that I like about this is I think it speaks to the essence of how you think about writing, which is actually don't think about writing.
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Think about taking an idea from your head, clarifying it, putting it onto the page, and get the idea from your head into the other person's brain. Yeah.
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You know, it's funny, I was reflecting on this quote actually recently and with with with my son, not with him, but about him.
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He's nine and he likes to make stuff.
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Well, at least I would describe him as someone who likes to make stuff.
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So he'll he'll have some cardboard and a a copper pipe and some glue a glue gun and some tape and some stuff.
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And he'll have this thing he wants to make.
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Like he wanted to make recently like a ring holder for my wife to put her rings on.
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And we weren't going to buy him one of those things and he didn't have any money.
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So he's like, I'm going to make one of these things.
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And he makes it and I would describe him as a maker, but really I was thinking about like what he really wants in the end is the thing.
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The making is just sort of the the step to get the thing.
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He just want he wants the thing in the end.
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He doesn't I don't know if he likes the making process so much.
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That's how I kind of think about writing.
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I do like writing, but I like the end product so much that the process is not really that exciting to me actually.
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Which is why I'm kind of a fast writer.
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I don't spend a lot of time on my pieces.
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I kind of want to get to something good and if I'm not there quick, I throw it away Yep. and start over.
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Because I don't I don't want to get I don't want to struggle through the thing.
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Uh I want to just communicate the thing in the end.
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And if there's too much work to communicate, I'll stop and start over.
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Well, one thing that stood out is you have this YouTube video where you walk through your process of writing a piece Yeah. for Inc. Magazine.
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And what really stuck out that doesn't happen to me is sometimes I write and I get a little bit contrived and a little bit like, okay, now I'm writing, I really need to focus.
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And I just watched your temperament through the video and it never changed.
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And there was a real sense of calmness that you maintained when things weren't working well. Yeah. Try to.
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Like what's the point of struggling?
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There's some point in struggling in other things.
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I think like certain things are worth struggling through.
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For me, writing is not worth struggling through.
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It's worth finding a flow because then you can ride that.
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So I've found at least for me, when I struggle with writing, it's a signal to stop writing.
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Not to keep pushing through the writing, but to stop writing, do something else, and come back.
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And oftentimes don't come back to what I wrote, but come back to a blank page and start over.
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And try to get there quickly.
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So the struggle I mean, it is important to struggle through things in life.
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That's how you're going to get better and stuff, but I feel like it's also a sign sometimes to say this isn't working and you're probably not going to make it work and you're going to get more frustrated and the frustration's going to show up in the writing.
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So kind of back off a little bit and then come back to it later.
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But again with the clean sheet.
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I'm not a big fan of like starting with something and working it to death until I get there. It's just time to go. Time to move on.
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And do you feel like that's general advice or do you feel like that that's Jason advice?
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I think it's only fair for anyone's advice to be about them, honestly.
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Now, whether or not you can use that advice or someone else can use that advice is up to them.
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But for me, my experience is my experience.
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I do what works for me and maybe that works for somebody else.
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So these are just ideas that's out in the world that someone might go, yeah, that's how I write.
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Or like, I didn't think I was justified in writing that way or I didn't think I could do it that way.
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But he's doing it that way, it gives me confidence that I can do it that way and that's kind of how I look at it.
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So I wouldn't tell you how to do it. Right.
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Who who might I say how you should write? Just how I write.
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Well, this really stands out as a as something that shows up in the way that you think about business and the way that you think about writing is just this sense of like feeling that flow.
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And it's just sort of step by step.
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It's like, is this the right flow?
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And there's just this sense presumably that you have in your body and your mind of like when you found that right idea that sort of slipstream.
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And then you can follow it. That's how it feels.
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I want to get into this effortless place where in in effect I don't really understand why things are coming out so well in a sense. Yeah.
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You know, like I'm I'm proud of the work at the end, but I don't really understand how I got there.
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Sometimes I read a sentence and I'll be really proud of it.
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And I'm like, that's a good sentence.
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I don't know where that came from.
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But it's really good and I'm proud of that sentence and that kind of propels me through to the next one and the next one.
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And then there's also an aesthetic though to when I look at what I'm writing.
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I can't exactly explain it, but I'll look at a sentence and I'll say, does that sentence look right?
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Like the letter forms, does it look right?
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Is it too jaggedy or does it feel right or are the other words too long and then too short and too like there's a there's something I try to get to where but it has to happen naturally is the point.
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Like I'm not going to replace a couple words because the shape of the word doesn't work for me as well.
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I want to write something out and I'll look at it and go, that feels good. That feels nice.
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Just like you you you you come upon something you're on a hike or something and you find a branch.
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Like every once in a while I'll find a branch with like lichen on it.
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I'm like, that just looks good.
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That's how I want my sentences to look. That just looks good.
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That there was no effort in that. It just is.
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And when I find those lines that really kind of propels me through the piece.
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And if I don't find one early, I know it's not going to be good.
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So I stop again, throw it away, come back to it later.
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I've heard people equate it to skiing.
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I'm not a skier, so Me neither.
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So I've like totally dropped the metaphor, but I guess that Shooting free throws maybe.
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Shooting free throws, who knows?
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But I guess you're ski and then you kind of find this line, you just sort of follow it.
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When you're in a really good flow, the line just sort of opens up and emerges.
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Actually, okay, we'll do a football analogy.
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Like I'm not a big football fan, but I know I know football.
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Okay, so basically like when you're running back, you're sort of following what the line is is is doing.
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They're trying to create a hole for you.
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And sometimes it just sort of emerges, but then you just got to run.
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And I have found that when I'm writing, there's there's certain times where I have to say I got to put the plans away.
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I'm not coming to dinner.
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Like I found a hole and I need to run because that hole will close in 12 hours. Yeah.
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You don't control the hole. Yep.
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It's just like someone makes it for you or something makes it for you and you go.
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And there's there's this song when I wrote this thing called the um 37 Signals Guide to Internal Communication. Yeah. Yeah. Read that.
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And I wrote that in like an hour and it's long.
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And I just couldn't stop.
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Like the the hole was open and I just felt like I just was in a flow and just kept going.
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And I barely edited that piece at all and I felt really good about it at the end, but that only happens when there's the hole.
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Again, if I if I'm finding myself in the middle of it and I think it was like I don't know, 30 points or something like that.
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And then sometimes I'm like, well, I want to get to 37 because that's our 37 signals, 37.
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But then I'm like, then now it's contrived and I have to stop myself very quickly from going over the edge because once I go into that contrived place where I'm where I'm I'm efforting something too much, it's going to be bad.
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I really don't want it to feel like effort.
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When it does, then I feel like I'm in the wrong place. Let me say this too.
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When I when I read something, I can sort of intuit that that's how the off I'm guessing here, but that's how the author was feeling when they were writing it too.
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Like I'll read something.
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I just read this book, The Overstory. You know this book? Yeah, Richard Powers. Yeah.
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Oh my god, it was incredible.
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I mean, it's a Pulitzer Prize winning book, so like I'm not the first person to say it, but his writing style, I just kept reading it and I'm like, man, he must have been smiling when he wrote this. That's how it felt.
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There's some super clever lines and clever paragraphs and clever passages.
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I'm like, he must be so proud of himself at the end of that.
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It's like, that that nugget, those six sentences together, that just nailed it.
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And I can just imagine a smile or imagine a pride in that in the author.
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That's what I want to get to.
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I want to have that feeling when I write something.
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What came to mind was Ah.
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Like this sense of just Oh my goodness. Yeah.
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It's just this awe, this majesty. Yeah.
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And I've had many moments throughout the years where I've seen that and I've had that wow moment and I've said, I didn't even know that that was possible.
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Like a sense of elegance that I want to recreate.
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That book is full of that.
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And I that's how I felt actually in that book. I was kind of shocked.
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I don't read a lot of fiction.
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And I started reading that was the first fiction book I've read in a long time and now I'm like hooked on fiction, so I want to get into more more fiction, but that's how I felt when I read that book.
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I go, wow, what a beautiful way to describe the unfortunate clear-cutting of a huge forest.
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He described it as sort of coming upon this huge clear-cut space, this big arcing hill that was clear-cut of old trees.
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And he described it like the stubble on a bald man's head.
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Which was just like my what a great way to describe like clear cut trunks are left, short trunks are left and just like desolate emptiness.
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Nothing that's bald people.
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Man, the the the thing that really stands out in that is sometimes you read that and you'll see something like that you feel like oh I need to try so hard when I write and you're using this word contrived.
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Like contrived needs like a big red danger sign like do not go there. Yes.
10:25
Because the way that that sort of elegance often comes out is exactly what you're saying earlier.
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I don't know where that came from.
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It comes out of the intuitive world, not the conscious world. I I believe so.
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I think most things that are good come off of the intuitive world, the gut basically. It's all gut.
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You were talking about the 37 signals guide to internal communications earlier. Yeah.
10:48
When you have a piece like that where does the genesis moment, how does that happen?
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What inspires a piece like that?
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Is this a a question that you keep getting, a sense of frustration? What is anger? Yeah.
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Yeah, anger, frustration, yeah.
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It's usually I'll read something or I'll hear something and someone will say like this is how we make decisions or this is how we communicate.
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I'm like I need to share how we do it because this is like I just feel like this is wrong or you know it's wrong for us at least but like this should not be the only version of whatever this message is out in the world. We have our own message.
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So we usually develop software and I write from a place of frustration or anger is too strong but it's like a fun anger.
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It's like oh that's okay, okay.
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Yeah, let me show you what we can do or how we do it.
11:29
So there there's this competitive spirit.
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I think that that drives some of that for me.
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But it's usually like one spark and then um again is is there a fire or is it just go out pretty quickly?
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It that it I really want to follow my gut on that.
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So if if it keeps burning I'll keep going until it peters out.
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And that's kind of how that one was.
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I wrote it kind of fast but there was a lot there and I felt like it was pretty tight and concise.
11:51
It was probably repetitive in a few spots and I probably edited out some of that but there was a point where I felt like I could only make this worse.
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And that comes pretty fast I think in my writing at least.
12:03
I will tend to get too wordy if I keep working it. Right.
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Things tend to get longer as I keep working them versus getting shorter.
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I usually start with a shorter version and that's usually the better version.
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And it's the same way in software.
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When I come up with an idea for a product or a screen and I sketch it the sketch is like the best version of the thing.
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All from there on out it only gets worse in a sense.
12:25
Just because the sketch of course doesn't take into consideration all the things that it has to actually do and we don't have to build the sketch. It's just a picture. No.
12:31
But um when I overwork a sentence or a paragraph or a piece it's going to come out worse. So I got to stop myself. Yeah.
12:42
How is that different from articles to books?
12:43
Because I know that I think with Rework you did a bunch of compression towards the end of the book.
12:50
So what is different about the nature of a book there?
12:53
Part of there's a couple things.
12:55
Um it's a very good question because there it is different but that book is made up of short essays.
13:01
Um what we did was we took a collection of short essays and cut the short collection of short essays down by half basically.
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Our contract was like you have to produce 40,000 words or something like that.
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Cuz the book has to be this thick, you know in the book world it's like it's thickness.
13:13
It's not even it's just thickness which is the weirdest So they're going to put in drawings, yeah.
13:18
Yeah, yeah so that's what we ended up doing but we we had we had these essays we're like you know what there's a really damn good half book here but this book as it is is too repetitive, it's not right.
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So we went and shaved it down by half and we handed it in and our editor was kind of horrified.
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Our editor was wonderful, he was incredible but he was like we said 40,000 words, this is going to be too thin.
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We said just will you please read the book?
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You know and and he read it and he said this is really good.
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I'm really proud of this. It's too short though.
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And we said okay, so is this just about length or is it about subject matter?
13:54
It was just about length.
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Okay, so we're going to add pictures.
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We're going to tighten the margins.
14:00
We're going to increase the font size ever so slightly.
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Like let's work within the system.
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Let's satisfy the demands and the requirements that you have but let's kind of add other things to the book and it turned out I think it really made the book better to have a picture with you with each book with each essay.
14:13
Especially in business books you never ever see that.
14:17
So it was kind of a happy accident to have all that in there but we were not happy with the 40,000 words.
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Even though I think the essays individually were good but the collection of them was the problem.
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If they were all spread out on the table or they were all published over 10 years individually I think we'd be happy with all the 40,000 words.
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But when you look at a book it's a collection.
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It's not a single essay, it's a collection of things and the collection didn't feel right.
14:38
I often think of writers they sort of have their zone.
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It's sort of like sprinters where you know or like runners.
14:45
There's some people who sprint, there's some people who run marathons, some people do 800 meters and I think that one thing that you've always done is you've never at least that I've caught tried to depart from the length that you do well.
14:58
So even going back to Getting Real it's like 90 short pieces and that's the same thing in Rework and Remote and It Doesn't Have to Be Crazy at Work.
15:07
It's all that same sort of format and that format you've then developed with all these blog posts that you've written and you haven't tried to say hey I'm going to write you know 10,000 words cuz that's what they do in the book publishing industry.
15:21
Well I listened to your interview with Derek Sivers who's like one of my favorite people and writers and all that.
15:26
And uh he said it the same way I would say which is write a bunch of essays first essentially then you can sort of compile a book.
15:30
So I didn't set out to we never set out to write a book necessarily.
15:34
We never really set out to write a book except Remote. Remote we kind of did.
15:38
But but It Doesn't Have to Be Crazy at Work Rework and Getting Real.
15:41
Getting Real was actually a book.
15:45
But some of those things were posted as blog posts first.
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So it's sort of a collection and then we then we modified and cleaned them up and made it like a singular voice cuz my writing style is different than David's writing style, my business partner and so we kind of wanted to unify the things.
15:57
But typically we put out a bunch of essays first to sort of establish it without thinking about a book in the future.
16:02
But eventually it's like we have a books worth of material here.
16:04
Can we turn this into a book?
16:06
It's not enough just to collect the essays but it's enough to have them first, write them one at a time over many years and then put them together.
16:14
But your sprinter analogy, I was a sprinter. Okay.
16:19
And uh Finally I a sports analogy I capped out at 400.
16:23
The 400 meter for me was like it. I could not run the 800.
16:27
I mean I could run it but I would I was bad. Yeah.
16:29
So I like it's great the indoor 50, 100, 200, 4 by 1 relay, 4 by 2 relay, all those relays and I could run the 400.
16:36
But if I tried to run the 800 no matter how hard I tried I would run it poorly.
16:40
I just am not built that way.
16:43
And it's a good way to think about writing cuz like if I can write a 400 or less essentially, 400 meter or less essay I'll do that well.
16:49
But if I push myself further than that, I mean you could say like maybe you should push yourself.
16:55
What's wrong with pushing yourself?
16:56
There's nothing wrong with that except to the point like I don't actually enjoy writing long things.
17:01
I don't really like that.
17:01
So I think there's more of a it's more fun to be even though I'm a bit wordy in this moment here but it's more fun to be actually more creatively challenging and intellectually stimulating for me to try to be concise with words in a way where I don't need to add anything more.
17:19
This is the thing, it's short, you get it and then you fill in the gaps.
17:24
So I really believe in a lot in asking the reader to to think.
17:28
I don't want to lay it all out and give them no room to think.
17:33
Like Rework and our books they typically are suggestions but they're not really there's no calls to action.
17:38
It's not like do these seven things and you will become whatever.
17:42
It's like here's a point of view and we're just going to leave it out there and then you can think about it.
17:46
I I like writing that way. Yeah.
17:50
How much of your rejection of precedent is something that you consciously cultivate and think about or how much of that is just temperamental in your personality?
18:01
Well I think it starts with the personality then what ends up happening is you start to you start to like double down on your own stuff.
18:08
Like for us to write a long book right now, like not an essay based book but like a literally like a you know 30 page chapters or something would be it'd be hard for us to do that.
18:17
I don't think we're very good at it but also I don't think we would feel like it would be us. Right.
18:21
So uh it starts with with with what's natural.
18:26
And then I just want to stay within the natural realm.
18:27
I really think that the the thing I'm trying to get across here is that it's okay to know your limits and work within them and not feel like to become a writer you must write like someone else or you must emulate this style or if you're writing short essays you're not really a writer.
18:45
Like a real writer would write a long essay or short means you don't have anything to say or what no it's like this is how you communicate, get really good at that and be yourself.
18:53
Just be yourself with your writing.
18:56
The thing I've always hated about writing um there go the eyebrows go up. Interesting.
19:01
Um tell me tell me tell me more. was was was before.
19:03
Was was when I had to write things I didn't care about in school.
19:08
Um I had to write it was all about length.
19:09
It was like long basically and subjects I didn't care about. And uh it was miserable.
19:15
It was it wasn't even writing.
19:15
It was like um it actually I would just call it pointless. Mm. That's what it was. It was pointless.
19:24
It's like you write about this topic and make it 10 pages or whatever and then it's like that that I mean you kind of have to do that growing up to some degree but then you can not do that anymore and find your own way.
19:37
That's what's important I think.
19:40
Yeah, the thing that I just did not realize existed was the feeling of getting excited about an idea and skipping to the keyboard for the same reason that you're talking about earlier is I can't wait to see the end product which is the synthesis and clarity Yes.
19:57
of the idea in my head now on the page. Yeah, it's exciting.
20:01
And sometimes it's frustrating I mean often times it's frustrating not even sometimes often times it's frustrating to like to to to have this idea and not be able to communicate it.
20:10
And this is why I'm going to come back to something I said earlier.
20:15
I don't find that trying to struggle through it is the way through.
20:18
I really think you just got to stop and throw it away and start over.
20:21
And the other thing I will often do is I'll just I'll talk.
20:23
I'll just like I try to write the way I speak versus having a a writing style that is separate from that.
20:29
And that makes it easier cuz then I can just go for a walk often go for a walk.
20:32
I don't like actually like to sit still and think.
20:34
I like to move and think.
20:36
So I'll go for a walk and and and and just sort of like talk it out and go oh, that's the line.
20:41
Like there's there's usually like a line that gets me or there's a combination of words or a title for the essay.
20:47
So I need some hook that I have to find that brings me back to the um confidence that I need to pull it off and I'll try again.
20:59
Confidence that I need to pull it off.
21:01
That's not what I was expecting you to say. Tell me more about that.
21:03
What were you expecting me to say? A sense of direction. Okay.
21:09
I I kind of see them almost as the same thing perhaps.
21:11
I guess I guess that confidence almost implies a lack of confidence in in in what you were doing.
21:18
So I don't think you meant it like that.
21:20
I the the confidence for me in that moment is usually it's not the initial stab.
21:24
It's the coming back to something that I couldn't pull off the first time.
21:28
So if I'm working on an idea and I can't quite get it there I do need confidence to return to it because like the prevailing feeling at that point is like couldn't do it. Couldn't pull it off.
21:35
So you need to overcome that I think.
21:37
So when I go for a walk I'm kind of like in a way I'm spooling myself up to and I'm looking for the hook.
21:46
I'm looking to find something that's going to work.
21:49
And then I'll go you know what this is yeah yeah I think I got this again and then I'll sit down and I'll start writing again and it's got to flow and then then it does feel feels like confidence.
21:59
It feels like confidence to keep going and finish the piece.
22:00
So I don't know if it is or not but that's how it feels to me.
22:05
How does editing show up?
22:05
The the best editor I've ever worked with was on Rework. Okay.
22:10
Um Rick Hogan was our editor-in-chief and he was awesome old school printed out red ink you know like symbols and like I got to look these up.
22:19
Right right Three dumb three lines under the thing.
22:21
What is that again or whatever?
22:22
Um and for as the first time I've ever worked with someone who really read the piece really really understood the piece really spent time thinking about it and worked hard to make it better and the edits did make it better.
22:35
I was skeptical I will tell you ahead of time maybe that's my overconfidence in my own skills or something but I was like what is an editor going to do?
22:43
That's how I felt and this like small little me thinking like what is an editor going to do?
22:48
And um he really woke me up to being like oh this editor can really make this piece way way better.
22:53
And my Ink editors were the same.
22:55
They didn't edit the piece in the same way but we talked through the things.
22:59
I find that it's easier to talk through improving writing than it is to look at another draft.
23:06
So when when I would submit a piece for Ink they wouldn't come back with a revised version.
23:11
We'd hop on the phone and talk. Oh wow.
23:14
And that helped me I I like the conversation about writing more than like looking at another version of it.
23:20
It just doesn't really do it for me.
23:23
So I like I like the all of the depth that comes with language verbal language and the conversation and the follow-ups and that what do you mean by that?
23:28
Why do you think that's better?
23:29
You can never get to that in like a draft that someone presents to you.
23:32
You just get the final result.
23:33
Then you have to ask like why this why that?
23:35
I prefer just to talk it out all the way.
23:39
So working with an editor was great.
23:41
I will say when I write my articles I don't share them with anybody ahead of time.
23:44
I don't ask for feedback on them.
23:46
I just put them out there and I'll edit usually as I go.
23:49
Sometimes I'll do a final read and you know even if there's a spelling error I just sometimes publish it and then like I fix it later.
23:55
I don't I'm okay with that.
24:00
Cuz it's not printed so I kind of feel like it's sort of okay even though probably isn't in a sense.
24:03
Since I write like I speak if I make a mistake in a sentence like when I'm speaking I don't go back.
24:12
I mean sometimes I will like oh I meant to say that but usually you just kind of keep going.
24:17
And I'm sort of okay with that.
24:17
Like what is it about writing it down that makes it have to be more perfect than saying it out loud?
24:26
Uh it's basically like saying it out loud but I can't be there.
24:27
So hopefully other people read it and say it out loud to themselves and if there's a mistake like you it's not that big of a deal.
24:33
I mean I want to make it right but also to what extent?
24:38
There's this this is a weird story.
24:40
I actually wrote about this once um I was in this Navajo rug um gallery.
24:48
And I was looking at these Navajo rugs and they're really geometric and and beautiful but they all were kind of like off in a way.
24:54
Like the triangle wasn't quite like the the angles weren't right and there were some mistakes what I thought were mistakes and I asked the guy I said why like why are there mistakes in these rugs?
25:08
And he said like you know this is this is his interpretation.
25:09
Uh the Navajo didn't see that as a mistake.
25:11
He basically said like just like if you're a walking on a path and you stumbled or you tripped or you took a slightly different direction.
25:22
You wouldn't back up and redo that section. You just keep going.
25:28
It's just like yeah there was a thing that happened but you just keep going.
25:31
And he goes that's what they do with their stitches.
25:33
If they kind of were off a bit it didn't matter.
25:34
They just keep going just as they would if they were walking or doing something.
25:39
And I wonder if that in some ways can gave me some latitude did not take like every not to take precision quite as seriously.
25:50
And as long as the message gets through that's enough. Yeah.
25:53
I it's so funny that you say that. So I Oh good for you.
25:57
And uh and I have two sets of basically bowls at my apartment.
26:03
I have the cheap bowls that I bought on Amazon that are Amazon Basics and they're black. They're perfectly round.
26:08
There's they're spotless.
26:10
And then I have this one bowl that's blue um and it's got sort of some Oaxacan patterns and I bought it down there and it's got all these little nicks at this point and it's like very imperfect.
26:20
The bowl isn't even perfectly round.
26:22
The texture of it is sort of feels a little messy and stuff but I always pick up that bowl first.
26:29
I never eat from the bland Amazon bowls before the Oaxacan bowl because it has so much more character.
26:35
It has so much more life.
26:35
It is so much more human. Yeah. Same thing.
26:40
It's yeah it's the wabi-sabi thing in Japan.
26:41
It's there's something about that.
26:42
Now I should correct the spelling error.
26:44
Like it does it doesn't make the piece better.
26:47
Your in your point the nicks and the chips make the bowl feel different to you in a way that feels better.
26:54
I don't think a spelling error makes the piece feel better but I also don't care that 340 people saw it wrong and then the rest 10,000 more saw it right when I fixed it online.
27:04
It doesn't really matter that much.
27:06
Yeah this is a a strange parallel that but it's somehow top of mind.
27:11
But there's that John Legend song where he says all your perfect imperfections.
27:15
It's like he's pouring out his love and his praise.
27:17
And I think that we're talking about editing earlier.
27:21
I think this is the problem where a lot of editors destroy writing is they try to make it perfect and they don't honor the perfect imperfections.
27:29
So no shade on my Ink editors but I had a few run-ins like that where there was like a sentence I wrote which I was really felt really good about and they kind of rewrote something and it was very it just felt like they were sterilizing it. Yes it's a great word. Yeah.
27:44
And I'm like no no it's okay if there's some bacteria on this or whatever right?
27:47
In my head I'm like that's yeah that might be better technically.
27:50
Like there's words sometimes they would use.
27:52
I I can't remember any examples but there was like the more it was the correct word but I don't want that word.
27:59
I would like the way the other word sounded and felt and it was a little awkward and I kind of liked that.
28:06
And so that's one of the tricks with editors is to help help them or help you know I guess help them understand what you're going for in your writing.
28:15
It's for me it's not precision.
28:15
It's not like it it's it's a feeling I'm trying to get across.
28:20
And this to sterilize something in some ways is to remove all the feeling.
28:24
Like you walk into a space that's sterile.
28:26
Maybe it's a beautiful museum or something or it's a beautiful modern piece of architecture.
28:29
I love modern architecture. I love old architecture.
28:33
But you walk into some modern architecture and it's too sterile. It's cold.
28:38
Everything's too perfect.
28:38
There's like three materials.
28:40
There's no dust anywhere. There's nothing.
28:42
And you're like I don't really feel good in this space or I don't really want to touch anything and leave a fingerprint.
28:49
Versus you walk into an old space that's patinaed. It's worn. It's been lived in.
28:54
Uh maybe the ceilings are lower.
28:54
It's more human scale and you're like this is messy.
28:58
This is sort of whatever but I love this space.
29:01
And that's how I want my writing to feel is like kind of like a lived in and I want our design to feel this way.
29:07
Like our products are designed differently.
29:08
They don't look like the industries where the industry work is all kind of everyone's like driving their style from Apple.
29:15
It's just like everything's like trying to be Apple.
29:18
We're trying to be like the cozy living room that's comfortable and it's precise enough but there's some attitude there.
29:26
There's some personality.
29:26
There's some humanity I'd like to think at least and I'd like to have that in my writing as well. Yeah.
29:34
Well I think that this is part of the problem with the keyboard itself is you have the delete key.
29:40
Whereas if you have a typewriter or you're handwriting you end up with all of these weird errors and these weird imperfections and you sort of go on these tangents and stuff like that and you're like, "Ah, I messed up, but I kind of got to go with it."
29:52
Sort of like the path that you were talking about earlier.
29:54
Whereas with the delete key, you can just look at the screen and go, "Delete, delete, delete, delete."
29:57
And I just wonder if the delete key has contributed to a kind of polish in contemporary writing. Good question.
30:03
I think you're probably right.
30:05
I mean, also like grammar checkers and spell checkers and these things like look, they can be useful, I'm sure.
30:14
Like in some cases, but I think when they become a crutch and you lean on them and you're aiming for again, like technical precision.
30:21
There are some writers who are wonderful at that, but I think it goes too far for most people and it removes themselves from the piece.
30:30
Got to be careful of that.
30:30
So, when you were working with the ink editors, with the rework editors and you were having those conversations, would you go back and rewrite the piece from scratch or would you go in and make line edits? Um both. It depends on the piece.
30:45
So, some of the pieces like some of the edits were so substantial, they wanted us to really rework the piece and there's a point where I don't know where the point is.
30:54
It's not like 50%, but there's a point where you just feel like this is moving around so much, it's not the same thing anymore.
31:00
So, let's not work from the same thing. Let's start over. And they were right.
31:04
Like this idea would have been better presented this way.
31:08
So, I'm not going to try to take this ball of clay and turn it into something else.
31:12
It's just not going to be that anymore.
31:13
There's not enough material there anymore. So, we'll start over.
31:16
Other times it was just like nailing a few sentences or like whatever. So, it's it's both.
31:19
It's not a I'm not rigid in those in those ways.
31:21
Um but I'm definitely not afraid of throwing out work. Right?
31:28
I don't think because I put it on the page, it needs to stay there in spirit and you move it around. It like it can go.
31:34
And I'm not just talking about like a line.
31:35
I can talk I can talk about like writing this much.
31:37
It's like close the file, don't save, new, right?
31:43
Not even the delete key cuz you can undo that.
31:46
And I found myself undoing deletes.
31:46
Like I want to like close the document, open a new document, so it's really fresh and start again.
31:53
Yeah, I also find that memory is an amazing tool for compression and focusing on what's important.
31:59
Like your brain doesn't remember things that aren't important.
32:03
So, if you need to rewrite the thing and you have a thousand words, the 250 that you actually remember is highly correlated with the best stuff.
32:09
100% and then I'm the same way with like to-do.
32:11
I don't keep to-do lists. Is that right?
32:14
Yeah, I don't keep I don't I have like a few things I need to do every day that I want to focus on and maybe I'll forget to do one.
32:19
Someone will probably remind me or whatever, but I don't like to have this list that I'm staring at of the things I have to do.
32:26
I want to remember the things I'm supposed to do so I can think about I want to think about these things.
32:32
How do you structure your days running a company so that you still have time to write?
32:39
Because it's obvious that it's paid off, but it's one of those things like sort of like going to the gym.
32:43
Like on a day-by-day, it might not be the best thing that you can prioritize, but on a year-by-year, decade-by-decade basis, obviously you should be going to the gym, you know? For sure.
32:51
Um I'm pretty unstructured.
32:57
I write when I have something to say.
33:00
I don't write when I feel like I need to write.
33:03
I only write when I have something to say.
33:05
So, it could be something comes up earlier in the day at work.
33:07
There's like some thing we went through.
33:10
I'm like, "I should write about that."
33:11
Or I have some other idea.
33:13
I should write or I read something I should write about that.
33:15
But I don't I don't set aside time every day to do this um or every week to do this. I don't have a cadence.
33:20
It's not like I need to write one thing a week.
33:23
There's times when I write a good thing every day for a few days, you know?
33:25
It just it it I have to it's a feel thing for me. The gym's different.
33:29
Like I have to go to the gym.
33:31
I have to work out with a trainer cuz if I don't, I won't do it.
33:34
So, I need an appointment for that.
33:35
I don't like appointments for writing or any creative things um except for when I'm learning something.
33:41
So, like I'm learning drums right now.
33:42
I'm trying to learn ceramics on a wheel, you know?
33:45
I need to go to an appointment to do that cuz there's someone waiting for me to teach, you know?
33:49
But at some point, I want to then not have the appointment and I want to do it because I want to do it. But I have to get there.
33:57
And with writing, I don't feel like if I said like I'm going to write from 11:00 to 1:00 every day or whatever. These are just times.
34:05
Like what if I'm not there mentally?
34:07
What if I'm not ready for it?
34:09
What if I had a bad call at 10:45?
34:11
Now I have to sit down and write?
34:13
Like I'm not in the mood. So, I don't do that.
34:16
I don't I don't schedule this.
34:17
The other thing is because I write quickly, I can fit it in.
34:21
In fact, I'll often try to write things.
34:23
I wrote something a few days ago called separation um which I which I really liked um and I I I had an appointment at 10:30 in the morning and it's like 10:10.
34:34
I'm like, "I'm going to write I have the I've had this idea for I'm like I want to write this now.
34:37
So, I've only got 20 minutes and I'm going to publish it before this call."
34:40
So, I like the compressed time frame.
34:42
Like I'm just going to get this out and be done.
34:45
So, sometimes I'll do something right before I'll write write before I have something else to do so I don't go on too long with it. Yeah. Yeah.
34:53
The other implicit answer there was was just space and buffer. Yeah.
34:58
Just having the space for that when you get inspired that you can actually sit down to write. a very open calendar.
35:04
Everyone in our company does.
35:06
We don't share calendars so we're not I no one can take my time.
35:09
I can't take anyone else's time.
35:09
If you want to talk to me or I want to talk to you, not talk, but like if I want to schedule something, ask you.
35:15
Hey, do you have an hour?
35:15
Do you have Are you free from 3:00 to 5:00 or 3:00 to 4:00 whatever it is and we'll have a conversation about it.
35:20
And that because of that, our calendars are open.
35:25
So, I don't have to try to squeeze I like I just told you that I tried to squeeze in a piece of writing in 20 minutes because I I kind of didn't want to let to go on too long, but I don't have these short periods of time throughout my day. I have buffers. I've got lots of time.
35:37
So, if it if if there's a calling, if I'm called to write something cuz I have something to say, then I'll just find the time in the day to do it.
35:44
There always will be time to do that.
35:46
I want to It's important for me in general, I found that one of my biggest regrets on a daily basis is having things scheduled that I don't want to do in advance. Ain't that right? Right?
36:00
So, if I want to write and I'm like, "I have no time this week to write." I would be so upset.
36:05
It's like why I don't want to do that to myself. So, Mhm.
36:10
Why do you think that there's so much bad business writing out in the world?
36:14
Is it people trying to posture? They're scared? What's going on there?
36:16
All the above and probably a thousand more things.
36:19
Um I'd say part of it stems probably from like MBA programs and business writing in in school, which is like fake.
36:31
It's just like it's fake right like business plans like fake like business plan competitions where you're like making up a fake business you're not going to start.
36:38
I don't think it's worth going through that exercise and I think it trains you to BS your your way through things because the whole exercise is BS.
36:47
So, God, you're getting really good at BSing and then it just sort of like you BS for three or four years and it just kind of becomes uh what you do, what you practice, what you get good at and that's kind of unfortunately what people get good at.
36:57
I think there's also um companies don't have a point of view.
37:01
They're sort of don't have anything to say uh and they then make up the things they think other people want to hear.
37:08
So, business is about selling in a lot of ways.
37:12
So, like what does What do I need to say to convince this customer versus like what do I really want to say because we have something to say.
37:19
I don't think a lot of companies have anything to say. They have a lot to sell.
37:24
And so they then write in that way.
37:26
And it's just like this is just flat and bad and jargony and empty and there's all the platitudes and I feel like you can replace this logo with that logo and it'll be the same thing.
37:37
The same different companies saying the same thing.
37:40
Then there's group think and there's all these things that happen in the business world.
37:43
Um and it's a very conservative place and I think the writing becomes very conservative and people are afraid to say anything.
37:49
So, uh and then also the other thing is like um a lot of companies don't invest in in writing in in terms of like they don't have a because like in they need to write content.
38:00
I mean, frankly like I don't like the word content at all.
38:02
It actually really bugs me because when you start thinking of things as content, it's like it's like no, there it's communication.
38:14
Like what do you want to communicate?
38:15
Not what do you want to put out there for SEO and whatever.
38:16
It's like content is just such a pejorative in my mind when it comes to writing.
38:22
So, anyway, but companies make content.
38:24
Everyone's pumping out content and I think you get content when you do that and that's the kind of writing that you don't like and I don't like.
38:29
Yeah, I think that what it's revealing is a deep truth that many people are in business and building things and they have no idea why they're doing it. Yes.
38:41
And then in order to cover that up, they're doing all this adding all this sort of fake and manufactured stuff to basically cover up the fact that there's no there there behind behind why they show up to work every day.
38:54
And the problem yes, and the problem is that in business, it's mostly following.
38:58
There's a few innovative companies. Most companies follow.
39:00
And so, they're following each other.
39:02
And like, "Well, they wrote this and they're popular, so that must work."
39:05
And so, I'm going to write in this style.
39:07
I'm going to write like that. I'm going to copy them.
39:10
And uh and then it's all SEO driven and search engine driven and you know, all all the things where you have to pump it out.
39:17
And if you have to pump it out, it's not going to be good probably, you know? Um I'm not going to lie.
39:23
I think I've fallen into that.
39:24
So, like I don't think the past.
39:26
So, so so I don't think I'm above this and I I don't either, by the way. I've been there.
39:30
This is a really good transition into your founder letter because you love writing these and you've written them for Hey and you've written them written it for Once um and I think that they're a really good example of how to show why you're building something. Yeah.
39:49
And basically if you're watching on YouTube, we'll put it on the screen right now.
39:52
If you're listening tune in on YouTube for this section because we're just going to break down what it is that you're doing here.
39:59
I want to start off with how you start both of these, which is you jump right into the problem.
40:05
So, for the once, you say something happened to business software. Can I stop there even? Go for it. Let's break this down. Yes.
40:13
So, I wrote that line and I go, "I know this is going to be good now."
40:16
I know the whole piece is going to be good.
40:19
So, for me, it had to start with a good line.
40:22
And I like this format of a line.
40:24
So, something happened to business software is um the kind of line that injects a question into someone else's mind without me having to ask a question.
40:34
This is not a question, it's a statement. Yeah.
40:37
Something happened to business So, so the reader's going to go "Wait, what happened to business software?"
40:39
And so, now they're bought in because now they ask themselves a question and they want to get the answer.
40:44
Um now, this is not a trap. It sounds like a trap.
40:46
It's not like manipulative, it's just like I love those kinds of lines that lead with a little bit of mystery and make someone want to find out what the hell I'm talking about.
40:55
So, I think that helps lead things in. Okay.
40:57
So, you go right there and you wrote that first.
41:00
You didn't come back and write that later No, I wrote that first.
41:02
It's kind of I'm kind of pissed at this point. You know what I mean? Yeah.
41:07
There's an attitude here that Yes.
41:07
I feel and is real and I have something to say about this.
41:11
And so, this kind of leads me into that.
41:12
You used to pay for it once, install it and run it.
41:17
Whether on someone's computer or a server for everyone.
41:19
It felt like you owned it and you did. Yes.
41:23
And so, now you're saying this what it used to be like Yeah.
41:26
and it's coming out hard.
41:28
Today most software is a service, not owned but rented.
41:32
And we got to talk about owned and rented and landlords and all that jazz.
41:36
We'll get into that in a second.
41:36
Buying it enters you into a perpetual landlord-tenant agreement.
41:40
Every month you pay for essentially the same thing that you had last month.
41:44
And if you stop paying, the software stops working. Boom, you're evicted. Is that cheesy?
41:50
I don't know, it felt good.
41:52
I like ending paragraphs with a punch usually and the punch is usually has to be short.
41:57
And it's sort of a summary and it's an answer and it's like a this happened.
42:03
So, in that's other one, it's like you owned it and you did.
42:04
It's like that sums up everything.
42:06
The next one is like boom, you're evicted and it sort of sums up the the the dark side of rental basically. Yes.
42:13
Um so, I I that's a formula that I tend to like.
42:15
It's not something I do because I it's a formula.
42:19
It's like it turns out to be a formula. It's it's emergent.
42:23
That's kind of how I like to write, but I don't go there I don't say like, "I need to do one of those paragraphs with the thing at the end."
42:28
It's just how it comes out for me.
42:30
But, when I can sum it up like that, I know it's a good paragraph.
42:34
The end of the paragraph to me is what makes it good.
42:38
Tell me about the genesis of landlord-tenant.
42:41
Where did that come from?
42:41
That was by accident um actually.
42:43
As I was writing this um I'm like, you know, used to own it.
42:50
And so, I I go like, "Well, now you don't."
42:52
So, I in my mind I go, "What's the opposite of owning?" It's renting.
42:56
Now, software as a service is never really talked about as rental.
43:00
That word is not does not come up.
43:00
It's almost like it's it's buried, it's hidden.
43:04
People don't want to talk about the fact that it's rental software.
43:07
Think about like, what do you think of when you think of a rental things?
43:09
Well, they're kind of beat up, it's kind of, you know, used, whatever.
43:11
You don't use that term in software, but really it is rental in a sense.
43:15
Um and I'm like, "I'm going to use that because while renting is great in a lot of ways and periods of your life or all the time, whatever it is there is a dark side to rental that people have probably run into in their lives.
43:28
So, now if I can frame this in a way that someone can can relate to an experience they had renting like their refrigerator doesn't work, the landlord never fixed it, there's a hole in the wall, there's a leak, you know, all the landlord stuff, all the the bad landlord stories.
43:41
Everyone has one somewhere, right?
43:44
In college or or wherever they're living now, whatever it is.
43:47
So now I can I can sort of personify SaaS as a landlord.
43:51
And it kind of is uh and uh it's just a way to establish a little bit of a of a of a personification um here.
43:58
And then I I kind of let that live and let that sink in and then we moved on here. Yeah.
44:08
For nearly two decades, the SaaS model benefited landlords handsomely.
44:10
With routine payers and prayers Yeah. Got to talk about that. Yep.
44:16
to the church of recurring revenue. Yes.
44:18
Oh, we got to talk about all that. We'll just stop there. Yeah.
44:20
So, the payers and prayers thing was something that I struggle I like it, but I struggle with it because as you just bounced over it and kind of stumbled, I stumbled writing it.
44:29
Payers, prayers, it's too close.
44:34
But, I still went with it cuz I still like it a lot and it helps of course when you talk about church and whatever.
44:39
So but but I was a little bit worried that people would stumble over that because it is kind of hard to say.
44:45
Um this this actually this sentence actually kind of happened and I don't remember anymore.
44:50
Happened in reverse where I knew I wanted to use church of recurring revenue cuz I like that line.
44:54
And then um the payer the prayers and payers thing, the alliterations, it's not quite an alliteration, but like that feel bubbled up from the other statement.
45:05
And I go, "Ah, I like I like this now. I like this play."
45:10
This is where writing becomes playful for me.
45:14
And then I know it's going to be good as well. Has to be playful. I think.
45:18
I don't like to get too serious about this stuff.
45:19
And so, I'm here I'm like, "Payers and players and church This is fun."
45:22
And I'm ripping on landlords to a certain degree.
45:24
Like this is getting fun.
45:28
Then let me just stop you there real quick. Okay.
45:29
One thing that I love about play that I just realized is when you're playing, you can't not be who you really are.
45:36
There's no such thing as play without personality.
45:39
And so, I think that what play does is it brings out the personality that so many people are seeking. Yeah.
45:45
Valuations shot to the moon on the backs of businesses subscribed at luxury prices for commodity services that they had little control over.
45:55
Add up your SaaS subscriptions last year.
45:57
You should own that [ __ ] by now. Right.
46:00
I like that sentence, right?
46:00
Well, I well, I think that that kind of hits them.
46:03
Boom, you should own that [ __ ] by now.
46:05
And that's sort of the third big hit. And you did.
46:08
That's the revelation for me. So, it's a revelation.
46:11
It's like "You're right, I should own that [ __ ] by now."
46:14
That's what I wanted to put in someone's head.
46:17
Like, "Yeah, I've been paying for these subscriptions for years.
46:18
It's kind of the same thing.
46:20
Yeah, I'm getting new features, but it's essentially the same thing.
46:23
These companies have been making tons and tons and tons and tons of money, valuations through the moon.
46:29
I should own this [ __ ] by now.
46:29
You're damn right I should."
46:30
Like that's how I wanted I wanted to transfer this feeling into the person at that moment and go, "You're damn right I should.
46:36
I hadn't thought about that, but yeah, I should."
46:39
You know, that kind of feeling.
46:39
So, that's what that was about.
46:42
So, now what you do is you have one more line here about SaaS and then what you do is you begin to introduce Once, which is this line of products.
46:53
So, tell me about that transition and then why you thought about the structure in this way of talk about the problem, do a transition and then talk about Once.
47:02
I want to get someone to to nod their head first.
47:04
So, if I'm going to get um someone to agree with me later in a sense I kind of want them to agree with me first.
47:15
So it's kind of like you read the first half of this and you're probably going to go, "Yeah. Yeah. Uh-huh. Yeah." You're nodding.
47:23
I want to find this resonance.
47:24
Like I'm nodding, you're nodding and now you're open to hearing what I have to say.
47:31
I've described what I feel like is the reality and now here's what I want to bring to what I what I want to happen next, what I what I think is that could be the new reality.
47:43
So, that's why that that generally that format works well for me.
47:49
Um I mean, I've seen and you when you look at great product demos, it's the same way.
47:52
They kind of show a product and they go, "This is what's wrong with the product or the the category and like here's our solution."
47:57
It's just kind of a nice way to I think establish a reality, get someone to go, "Yeah." And then they're open.
48:04
And then you have some fun with Once. Once. Once. Once. Once.
48:09
But what stands out is the way that you begin that is you say, "Once.
48:15
Once upon a time you owned what you paid for.
48:18
You controlled what you depended on and your privacy and security were your own business." Can I stop you there?
48:25
The name Once, which is this brand, once.
48:28
com that the name came from um writing that once upon a time thinking actually, I didn't write thinking once upon a time used to pay for software. Huh.
48:39
I'm like Once is actually once upon a time. That's good. I like that word.
48:44
It also since we're paying once, once and once upon a time, like there's this double meaning there, which I really liked. course.
48:52
And um so, it actually the name of the thing actually came from writing and thinking about how to talk about the thing.
48:58
And then how do you think about Now, you have the basically five bullet points that you talk about with Once.
49:04
So why five bullet points?
49:07
Why do you focus on those?
49:09
You say, "Pay one time, own forever."
49:11
You say, "We write the code, you get to see it."
49:12
You say "We give you the software, you get to host it."
49:16
You say, "Simple and straightforward, not enterprisey and bloated."
49:19
And then finally, for one fixed price. Once.
49:25
So, those bullets sort of follow a similar structure where the first half of the sentence is like the previous existence or reality and the second half is like the new the new things. I like that pattern. I like the bounce. I like the rhythm. I like the bounce.
49:42
To me like if something's bouncing it's it's moving.
49:43
I like the movement in the words and the sentence and I think it pulls people through. They're short. They're punchy. Yep.
49:49
But hey, let's go on to the Hey letter.
49:54
So this one you open a little differently.
49:55
You say, "Hey everyone, I'm Jason, CEO here at 37signals."
50:00
So what are you going for there?
50:02
Yeah, that that's a good question.
50:02
Um when we launched Hey which is an email service.
50:07
I launched it initially with a with just this letter.
50:12
This letter is currently on the existing site if you go down to the bottom of it. But initially at hey. com it was just this.
50:19
And um it it was just this for a few months.
50:22
So we didn't want to say exactly what we were doing, but we kind of want to say something about what we were doing.
50:26
And in this case, I felt like it was more of a personal letter.
50:31
The what the the once one is more of a statement.
50:35
This one felt more like a letter.
50:35
Like I'm writing it to you and to say hi, here's my name.
50:40
It kind of opens it up in a more personal way.
50:41
Um I don't know strategically why I went that route, but it just felt like the right thing to do if there's only going to be this. It's less aggressive.
50:52
It's more like a love letter to email.
50:55
And so I wanted to open up in a in a in a happier thing than like a sharp statement.
51:00
One of the things though that does show up in both is that has the same structure of things used to be this way. We loved how they were.
51:10
Then they became broken and now we're trying to redeem the way that things are for how they should be. Structurally the same.
51:16
And I think that what's important maybe about this if you're going to drive anything is like again, there's a there is a formula here.
51:23
But they don't need to be the exact same formulas.
51:25
This they're similar formulas.
51:27
Like this one's more of a personal letter.
51:28
Um but you'll see at the bottom of this one my my avatar is in the bottom of this one.
51:32
The other one is not on the left hand side.
51:36
Um my email address is on the left hand side.
51:38
It's not on the right hand side.
51:40
Like there's some some differences, but strategically or not even that, structurally it is the same approach to getting a message out there which is to establish how it was or what's wrong with the current and what we're going to do about the the present.
51:55
It then says, "Email gets a bad rap, but it shouldn't. Email's a treasure.
52:01
It feels great to get an email from someone you care about or a newsletter you enjoy or an update from a service you like.
52:06
That's how email used to feel all the time."
52:09
And this is a feeling that is I want to get across early because most people don't like email.
52:17
But you're like, "Actually, it's not that I don't like email.
52:18
Like if I get an email from my wife, like I like that.
52:22
If I get an email from an old friend, I like that.
52:24
My uncle who's 100, he sends me an email, like I'm look when I see my my mom's uncle, my great uncle.
52:29
I'm like "This is amazing. I want to read this." So email is not bad.
52:34
What's become of email is bad, but at its core it's still a wonderful thing. It's a treasure. So yeah.
52:42
I want to people to go back go, "Yeah, I don't hate all email. I hate the spam.
52:46
I hate like the the too many things that you know, emails from people I don't know.
52:49
That's the stuff I don't like, but email itself is actually wonderful.
52:54
Just like getting a letter in the mail is wonderful, but you also get junk mail. Do you hate letters?
52:56
No, you kind of like letters.
53:00
Wedding invitations are great. right? Yeah. But things changed. Uh-huh.
53:04
You started getting stuff you didn't want from people you didn't know.
53:08
You lost control over who could reach you.
53:10
An avalanche of automated emails cluttered everything up.
53:15
And Gmail, Outlook, Yahoo, and Apple just let it happen. Right.
53:19
There's sort of the alliteration, the AA. I like this thing.
53:23
Uh I like using the same letter to start start words when I'm trying to be really have an impact.
53:28
I feel like it bounces well again.
53:30
So this avalanche of automated emails avalanche automated.
53:35
Like multiple syllable words together.
53:38
That's what creates the bounce.
53:38
I'm thinking about this red ball.
53:39
If I'm doing red balls on the syllables, is there's a lot of bouncing here.
53:42
And I like that I like that effect occasionally.
53:46
You'll see most of my words are short.
53:51
I don't like a lot of syllables in my stuff, but occasionally I want to go for that.
53:54
And then because it's rare you feel it differently.
53:59
Um and so that's where that that goes.
54:00
When you say because it's rare, avalanche of automated, like those rare more rare words. Like a lot of syllables. Avalanche automated.
54:08
That is like a it's like coming across it's like going on a walk and coming across like a lizard.
54:14
Uh and you're like, "That's a beautiful I don't see that very often.
54:18
Like that I'm going to look at that now."
54:19
That's how it feels here.
54:19
It's kind of a weird super weird analogy, but but but but but it's like coming across something you don't see very often.
54:25
So we're in the rest of the words it's pretty tight and short and but then there's these occasional things that stand out.
54:31
And I wanted the avalanche of automated cuz that's how it feels.
54:36
It feels like an avalanche.
54:37
Like you're out of control of an avalanche. You're caught in it.
54:41
You can't do anything about it.
54:41
Of course it can be tragic.
54:42
This is not that, but it's this barrage. It's this force Yep.
54:48
that feels like it never stops when it comes to email.
54:50
So I wanted that's what I wanted to get after. Ain't that right? Yep.
54:53
Also, this is something that I think every writer can implement is whatever your predominant style is, if you do the opposite when you want to emphasize something, it'll stand out because it is distinct and different. 100%. That's great. I agree with that.
55:08
Now email feels like a chore rather than a joy.
55:11
Something you fall behind on.
55:14
Something you clear out, not cherish.
55:16
Rather than delight in it, you deal with it. Right. Agree?
55:23
So more than I would like.
55:24
Yeah, so this is this is where I'm taking email away from the things that are pleasant.
55:29
Like the you know, getting an email from a friend, hearing from a family member, whatever.
55:33
Like that's you can envision that. These are now hassles.
55:39
And that's how most people think about email.
55:41
It's like, "Yeah, that this this is avalanche of automated stuff, all these hassles.
55:44
Like yeah, this I'm not into email."
55:47
So I'm setting the stage to turn the stage Right. And flip it around.
55:52
So I want people to go, "Yeah, yep." Again, nod their head. "Yeah, this sucks. I yeah, this sucks."
55:58
Sean Perry has a line that he shared on this podcast that I really like where he says, "All stories are about the 5-second moment of change."
56:03
And what he's saying is that there's something that happens at the beginning and then at the end it will be the opposite of what's going on.
56:12
So take your classic rom-com, right?
56:13
You have somebody who's in state A and they have all these things going on and by the end of the rom-com it'll be the opposite.
56:21
They're going to go through a transformation.
56:22
And that's exactly what we're about to see in the next section. That's a great point.
56:25
And yet and yet email remains a wonder.
56:28
So I think that what you've done here is you've said this is what's happened with email.
56:32
You sort of set up this pain, this annoyance, this sort of agony of having to check your email.
56:38
And now what you're about to do is you have that change into sort of delightness and the sense of possibility. Yes.
56:45
And the word wonder and earlier the word treasure.
56:47
So whenever I'm talking about the positive aspects of of email, it's like really special positive thing. They're enchanted words. Yes.
56:54
So I I I you know, I didn't like go through thesaurus to find these. They just came out.
56:57
But but but they come out in a way where um um they are the right words for that statement.
57:06
And I I couldn't come up with better ones.
57:08
I really wanted to think of them that way.
57:11
Thanks to email, people across cultures, continents, countries, cities, and communities seas, all seas. Oh I I I caught that. Here's another one. Right. Communicate every day. It's reliable. It's simple. Boom boom.
57:25
It makes it easy for two humans to share their love and for millions of people to earn a living. There you go. There's a lot of Yeah.
57:35
rhetoric that you're playing around with. paragraph.
57:38
I'm not surprised at all. It felt really good. It felt really good. It came together.
57:41
I love when I've got a couple C's going and then like I got to find some more.
57:46
And the ones I find aren't contrived. Another C. Yeah.
57:50
They aren't they they it's like I didn't reach too far. That was clever. Nice. Convincing. Yeah.
57:57
So I But but but the the thing is is like I didn't reach like sometimes you you you reach for a you know, alliteration or something and it's like that didn't fit.
58:06
You could tell someone is trying too hard.
58:08
I want to make sure I'm not trying too hard.
58:09
But um that paragraph to me is the is the um the the the the fill the fill someone up with with positivity and like um and and wonder following from the previous you know, it's just like it's it's making it's it's cashing in on what I said earlier.
58:28
And now it's filling that word wonder with these things.
58:33
So good news, the magic's still there.
58:36
It's just obscured, buried under a mess of bad habits and neglect.
58:42
Some from people, some from machines, a lot from email software.
58:48
Email deserves a dust off, a restoration, modernized for the way we email today.
58:53
So let me get into some of this.
58:55
So um neglect goes back to an earlier part in that piece where I said like Gmail I forget like Gmail, Apple, Yahoo, whatever. They let it happen. Right. So that's neglect.
59:03
That's that's closing the loop, closing the circuit on that.
59:07
Um and people aren't going to remember that, but I do believe it stays with them in a way where subconsciously there's a closing of the loop there.
59:18
Some from people, some from machines, a lot from email software.
59:20
That if if you look at comedy writers, a lot of the way that jokes are structured is they'll have the first two things in a list of three that'll be the same and then the third one breaks the pattern. Right. Well, I love comedy.
59:35
I'm not a comedy writer, but I do maybe it's just something that I absorbed perhaps.
59:41
But really we're about to make email software.
59:43
So up until this point I have not said what we're going to do.
59:48
I've just said like what it should be.
59:50
So this is the first time I introduce that like the problem is actually also with email software.
59:56
Now I still don't actually get deep into that we're going to make email software necessarily, but it's a hint as to what we're about to do with this hey. com thing. Yeah.
1:00:05
And with hey we've done just that.
1:00:08
It's a redo, a rethink, a simplified, potent reintroduction of email, a fresh start, the way it should be.
1:00:15
Hey is our love letter to email and calendars and we're sending it to you on the web, Mac, Windows, Linux, iOS, and Android. Yes.
1:00:27
I added calendar later because we added a calendar later. Right.
1:00:29
Um it's funny because that's the one I don't like that in there.
1:00:33
Like it's like it feels tacked on.
1:00:36
I almost stuttered there.
1:00:36
I was like wait, is that in there?
1:00:39
Yeah, I I'm like we added a calendar. So I I did add that.
1:00:41
Um But yeah, that's that's it.
1:00:43
I I barely talk The whole point of this even though I want to close the loops and I knew we had like months to go until we we released the thing.
1:00:53
Um I wanted first to establish that we had this domain hey. com.
1:00:57
I want to give people a reason to go there and go what the hell are these guys about to do?
1:01:02
That was really the idea.
1:01:02
So there's some clues but not really and and and then it just feels like it it wraps up and then I want to say like it's going to be everywhere.
1:01:11
That's what all the platforms basically suggest.
1:01:12
Like this is not like just a small thing. It's a big thing.
1:01:16
We're going all out on it. Yeah.
1:01:21
The thing that I learned in the last 20 minutes or so as we were doing this was how much you like playing around with the rhythm of words, right?
1:01:31
So you said a redo, a rethink, prayers and payers.
1:01:38
All the the these sort of playing around with words of sort of this repetition. The jabs. Right.
1:01:42
It's like a boxing match. Just jabs. But they're friendly. I like that.
1:01:46
I like the again, to me it's about it it's it's a it's a it's a bounce. It's this bounce.
1:01:54
I keep saying the word bounce so it's like getting repetitive, but that's how it feels and I I I like that piece.
1:01:57
I like the motion in a piece. Um yeah.
1:02:06
Let's talk about this post that you wrote.
1:02:09
My favorite post you've ever written is called the writing class I'd like to teach.
1:02:11
And basically what you say in it is that you would work with students to take a piece that's say five pages and then they distill down to one page and then one paragraph, one sentence, and then maybe even one phrase.
1:02:23
Why would you focus on that idea for for the class?
1:02:29
To me distilling and editing Actually, you know, I prefer the word distilling more than editing in a sense.
1:02:35
Distill it it's an exercise in distilling something down.
1:02:37
It's it's very easy to just for some people may not be easy in a sense, but you can always add more words to things.
1:02:44
Like got another hour, write more words.
1:02:45
You can write more words.
1:02:47
Even if you they're bad words, you can add more words.
1:02:50
It's harder then to take this thing and chop it down and not lose too much meaning.
1:02:55
You're going to lose some meaning along the way.
1:02:56
You might gain some for a while and then you're going to lose some.
1:03:00
So I kind of this I like this idea of five paragraphs whatever might be two paragraphs too long.
1:03:05
So we need to the three paragraph version or whatever or what pick a number. It doesn't matter.
1:03:10
It could be five to four to three to two, whatever it is.
1:03:13
There's a point it's like a kind of a bell curvy thing where it there's a point where like this is actually getting better and then there's also a point where you've gone too far.
1:03:20
And so I want people to experience all of that which is getting better and then going too far and realizing that it's still a good exercise.
1:03:28
Like can I boil this down to one sentence?
1:03:32
Can I boil it down to one word?
1:03:32
Um even though it's not practical, it's still a good thing to go through.
1:03:39
I just like in all the writing classes I ever took which was not that many.
1:03:41
It was just the required ones in high school and college or whatever.
1:03:46
It was always just write, write, write.
1:03:48
And then like do a second draft, do a third draft, whatever.
1:03:49
And whatever it was like the formal process.
1:03:53
It was never about make this tighter, briefer, shorter, more concise, more distilled. Um more pointed.
1:03:59
It was never about that and I always wondered why not?
1:04:03
Like isn't that really what we should be aiming to do?
1:04:09
Um so that's why I thought this course should exist and it's the one I want to write or one I'd want to teach if I ever taught one.
1:04:14
Um or I mean again, I like wrote this in a way like go ahead, you teach it.
1:04:18
I I don't this isn't my I mean it's I don't know if it's my idea wherever it was, but like go take it.
1:04:22
I hope someone else does this. Yeah.
1:04:23
Um cuz I think it's important.
1:04:25
And also another one I wrote another one about iteration um which is a similar idea.
1:04:31
Like if I was to teach just any class at all it would be about iteration.
1:04:36
It'd be take something, a project. Pick a project. I don't care. It could be about rocks. It could be about trees.
1:04:40
It could be about furniture. Turn it in.
1:04:46
The whole semester is just making it better.
1:04:49
Versus in school for the most part at least in my experience it's like turn the assignment in, onto the next assignment.
1:04:55
Turn the next assignment onto the next assignment.
1:04:56
Turn the assignment in onto the next assignment.
1:04:59
But if you're working on something in life, you're typically kind of working on the same thing for a while and you want to keep making it better and better and better.
1:05:05
So the idea of teaching iteration, giving people practice in iteration is kind of what the writing class is, but it's also a broader idea of working with this thing a little bit more.
1:05:15
I mean you've been doing Basecamp for what, 27 years? 25 years.
1:05:16
Basecamp itself's been 20 years.
1:05:18
The company's been 25 years. Yeah.
1:05:20
But yeah, 20 years of Basecamp.
1:05:22
Multiple versions along the way.
1:05:25
Um and we've made other products since, but yeah, Basecamp has been iterated on and iterated and It's a true joy and pleasure to really hone something like that.
1:05:33
To really get something right like that.
1:05:35
Um and to like take a piece I always think about it in terms of a piece of furniture.
1:05:41
Like you take a piece of wood, you got this piece of lumber and you sand it down and you sand it down and you feel it and how does it feel? How does it look?
1:05:47
And you hold it at different angles and you can can make this better. Can make this better.
1:05:50
And you just keep doing that until it's in that case it might be done.
1:05:54
Software doesn't really have the same end point perhaps as as a piece of wood.
1:05:57
Some point it's all gone if you sand it all the way.
1:06:00
But this idea that you can keep working this thing uh and and not just like put it aside move on to the next thing.
1:06:06
The other thing that I like about it, so there's two things actually.
1:06:09
The first thing is it forces you to understand the essence of what you're trying to say.
1:06:14
And then the other thing is when you do that, I think that you stumble on things that you wouldn't have found had you not been forced to compress.
1:06:22
And I think that you did this in your once letter.
1:06:26
You said once upon a time, once, once, once. Yeah.
1:06:29
That is in one word, that is the one word description of what I'm going for.
1:06:33
And you also could have said you could have titled that like against the church of recurring revenue and actually not even had those words in the piece, but against the church of recurring revenue would have been a one sentence summary of what's in the piece and I'm trying to make a point here which is that often the distillation is like an emergent property.
1:06:55
It it's it's not just taking the parts and making them smaller.
1:06:59
You could have the distillation words not even be in the piece. Yes.
1:07:03
That's often times what a what a headline is.
1:07:05
And this is actually one of the most interesting things through when I was writing for Inc. magazine.
1:07:08
I didn't realize this, but I didn't get to write the headlines.
1:07:11
I knew this eventually, but editors write the headlines.
1:07:14
And the headlines are often like not in the piece.
1:07:16
And it was kind of cool to see that which is someone else's distillation of this thing you wrote that's this long. Now it's this long.
1:07:24
And and this is what they think it is.
1:07:27
Now of course there's like link bait and there's all the other things that kind of poison that world and that well to some degree.
1:07:34
Um but I think it's a great point.
1:07:34
Um you you are sort of squeezing something out and and in some ways what's what what remains and what comes out are different things.
1:07:45
And the drop that comes out could summarize the whole thing and maybe that's the one liner or the one word. You know, yeah.
1:07:51
And it could be a different word that does not represent it. I like that. Right. It's a good point. Sap to syrup. Right.
1:07:54
It takes a 40 gallons of sap to make syrup and syrup is just distinctly different from sap. It is. It is. Good point.
1:08:02
They're two S words, too.
1:08:05
Tell me about how writing is in your hiring process.
1:08:08
It's actually the first thing we look at. The first thing? First thing. Oh, how about that?
1:08:14
Because I don't look at resumes.
1:08:16
We look at cover letters. The first thing.
1:08:17
Now of course, if someone's going to apply and like for a programming role and they're not a programmer that's a problem.
1:08:24
But the first thing we look at is not the resume.
1:08:25
It's how have they responded to our call for applications.
1:08:30
And we say like write a cover letter.
1:08:33
And if the cover letter is written in a way where it's a generic cover letter they're gone immediately.
1:08:39
Um even if it's well written.
1:08:39
If we can tell that it was like written for anyone and they just replaced our name, I'm just not interested in that person.
1:08:46
And we we might lose good people because of that, but it's okay.
1:08:47
I'm not interested in that.
1:08:49
I want someone who said I'm going to write something to them.
1:08:54
Uh I'm going to say something to them.
1:08:57
And so that is the first filter.
1:09:00
It's their writing ability.
1:09:00
Their ability to communicate who they are, what they're about, why they're applying.
1:09:05
And if it's like dear hiring manager, like that's a problem.
1:09:07
And if it's like very generic and buzzwordy, that's a problem.
1:09:11
It's really the best filter we found to get to the kind of person that we want to hire.
1:09:17
Uh not every company is going to want to hire like we hire, but we know that the majority of our communication is written and we write a lot internally in a lot of different ways and we found that the best way not to waste time is to write something right the first time versus having someone write something
1:09:35
like what what does that mean and they have to rewrite it and like re-explain it or they say it they write it in a wrong way that freaks people out and then someone else has to explain I want to cut all that out from the beginning so it's a very important thing and in every position we hire the best writer. Wow I mean we
1:09:49
Wow I mean we They have if there's a tiebreaker the best writer gets gets an app. Yeah.
1:09:56
Is there a lot of long form writing that you're doing or is most of the writing multi paragraph sort of in Basecamp and Um there's like I mean long form for us is the I don't know 800 words 1200 words something like that like a pitch an idea. Yes.
1:10:10
Um every 6 weeks every team lead has to write what's called a heartbeat which is quite a long thing it can be quite long summarizing all the work their team did over the last 6 weeks and the way that's written is really important because this is how we disseminate information internally we don't have meetings there's no status meetings. It's all written up.
1:10:27
It's all published to Basecamp internally so people can read it on their own schedule on their own time but it has to be good.
1:10:36
This is really like the summary of our company's activities over the last 6 weeks.
1:10:42
And we would never have AI do this this is not a summary of tasks or a summary of output it's someone's own words this is very important to us so it's someone's own words and so there's a lot of that kind of writing and there's shorter writing too.
1:10:56
A lot of commentary and whatever but but it's the long for if you can't write long form you can't work at Basecamp. Yeah. Yeah.
1:11:02
What makes one of those heartbeats good?
1:11:09
Usually that's a that's a really good question cuz there's a few people who write really really good ones and I'm like why why are these so good?
1:11:14
First of all there's personality in them.
1:11:19
It's not just a summary like it's not like a computer summary of things it's like this person worked on this this was really hard we were trying to break through this idea we couldn't get there they really nailed it or they put in some extra effort to make this better
1:11:31
for someone else there's a lot of things that are about helping others whenever I read heartbeats and it's like this person helped this person solve a problem I'm just like it just inspires me it's great and it feels like the writing is better. Um
1:11:42
Um and usually they're short they're short summaries but they get to it in a way where like I'm like I know exactly what happened I wasn't paying attention this thing at all for 6 weeks and in this amount of writing with these people who are referenced in it I know what happened.
1:11:56
That's how it has to feel and there should be some personality like I should know who wrote this like I can tell Rosa Rosa writes these incredible heartbeats.
1:12:05
Her writing is so good and and like I go that's yep Rosa wrote that I don't even need to see who wrote it like I know Rosa wrote that or Brian wrote this like I can just tell so there needs that needs to come through.
1:12:17
Um we're very anti internally very anti like AI style writing like I don't I don't want convenience right I don't want convenience I want people's own words the people who I work with who I talk to every day I want their words.
1:12:32
In the in their choice of words there is more meaning because I know it came from them so there's there's something to that that's really important to us the other thing that's great about writing internally especially long form this is I think lost in so many people is that when you do things orally so if you're if you're having a meeting which is how most companies communicate it's only good for the people in the room
1:12:54
and someone say well you can have a transcript well okay maybe or you can record it like it to go back if you're a new employee joining the company 8 months from now and you want to go back and like understand how this company
1:13:05
runs to watch like to try to watch 40 hours of boring ass video from a meeting it's you're not going to do it but you might skim and read some things and see some things catch your eye. The institutional knowledge that's built
1:13:18
The institutional knowledge that's built up in long form writing is wonderful for the future.
1:13:23
It's good for now but it's so useful for new employees to get up to speed quickly on how the company communicates writes shares by looking at the evidence of past people doing that versus if you weren't there you missed it or hey watch this 45 minute video what with like you know 3 minutes of good stuff in
1:13:43
it who's going to do all that you know so I I think it's so valuable and it's searchable and it's just it's easy to access and it's easy to link to and point out and share with someone else it's just so transferable that that I think it's a wonderful thing to do and I don't think enough companies do it. Or
1:13:56
Or they do it in the boring business way we've been talking about where there's like no conveyance of real information there's just a lot of words.
1:14:06
And it's like I don't know what I just read I'm no wiser for it I'm I'm worse off for it I wasted time and I don't get it that's how most companies write and I think it's a shame real shame and a real probably like at the core of a ton of lost productivity in the economy.
1:14:21
So if I came to you and I said I wrote one of these heartbeats and the ideas were fine but I was writing like an AI I was writing with that sort of sterilized posturing business writing sense how would you coach me to get to a place where I'm writing the kind of heartbeat that is worthy of your attention.
1:14:44
Yeah well first of all I would just it's very simple I'd say just tell me.
1:14:51
Because I think that um most people don't have any problem communicating.
1:14:56
Like just talking it out like so what did you do last week tell or tell me about the project last 6 weeks or whatever it was like and they would just like loosen up and and say it they wouldn't struggle through it they'd recall some things they'd say some things I'd say just write that down instead.
1:15:11
Like it's it's such a cut through it's like so easy to get to what someone really wants to say by just saying well then just say it out loud. Talk it out.
1:15:21
Because it it takes the whole like I have to write something down pressure off of it and then it's just communicate it's pure communication at point and humans are very very good at just talking to each other so just talk it out that's what I'd say and like okay now like you can even just record that and like literally write it down word for word if you wanted to or just then I would say then I would say just say that then just write that.
1:15:44
I'll often do this for myself like when I'm writing some like marketing copy for Basecamp um and I want to talk about this actually in a second cuz I don't I don't like the current state of websites which is one of the reasons I write letters and we'll talk about this in a second.
1:15:58
I'm going to inject an idea here to talk about but but um writing like a headline or something and and I'll and I'll I'll write this like pithy clever headline or something I'm like and then I'm like would I ever say that out loud to anybody to describe Basecamp?
1:16:12
And I'm like no I wouldn't so why would I say it here?
1:16:16
And I find that like there's this there's this feeling of like writing clever copy and head and I love writing headlines I it's probably one of my second favorite things to do besides these letters I love it but it really has to be something I would say out loud otherwise it feels disingenuous. Yes.
1:16:30
And then it's like this mark then you're in this marketing mode exercise where you're almost trying to impress yourself with your cleverness but you're just like not communicating anything in a in in a real way so I'll often just say like would I ever say this to anybody?
1:16:44
Or or if I'm trying to describe Basecamp like how would I describe Basecamp and I would just say I'm like that's better than any I spent an hour trying to write out how to describe Basecamp versus I just said it in 12 seconds and like that was better than anything I've ever written basically.
1:16:55
But you know this happens all the time it's so easy to fall into this trap but it's telling that you do too after all these years.
1:17:03
The challenge is at work and you're kind of talking all your co-workers about about what's going on and then it's really musicians do this all the time where they start making music to impress each other or like think of your classic sort of film festival movie it's like made for other people who are interested in film and not just made for your average person who for you is just buying software.
1:17:23
And this is a real trap that when you're writing marketing copy or trying to communicate anything about your product it's so easy to fall into.
1:17:32
It's it's like it's the jargony side of it it's it's the it's the you're forgetting who you're writing this for.
1:17:41
There's this sort of feeling that you're writing it for your company but you're writing it for customers and these people know basically nothing about you.
1:17:49
And so you really have to keep saying would I say this to someone I met on the street right?
1:17:55
If I'm in an Uber and someone like what do you do or what do you like how would I say it?
1:18:00
And why is that inadequate like what why can't I just put that on on the page?
1:18:05
Because there's there's a sense of like well it's just like it's words like it's not professional that's the other thing it's like not professional to describe your product the way you describe it to an Uber driver but but what why not?
1:18:18
Like why not just get to the point? Right.
1:18:20
And part of the problem is and this is where I want to get to the website thing website design is part of the problem that websites have a there's many different ways to do them but they have this format where there's like blocks of text and a picture and another block of text and a block of color and there's like it's it's all it's all shattered.
1:18:42
You know you can't read you don't read a website usually these days there's not a cohesive story that's being told there's like these little pieces and people are scrolling through them and you browse the web you don't read it in a sense.
1:18:54
So I think people don't think about communicating which is why what's nice about writing a letter is if I have a letter format people are familiar with what a letter format looks like and and it's short enough that someone's going to read it or they're not.
1:19:09
But if they start they're almost certainly going to finish because it's not that long and hopefully I'm pulling them through and it's you're able to read a letter you're it's hard to read a website how should it be different?
1:19:22
I like long-form like more of a long-form old-school like direct mail style letter kind of style.
1:19:31
Uh which we've experimented with in the past and and I've tried to do that.
1:19:32
Our current site's not quite like that, but there's longer paragraphs.
1:19:36
People are used to reading things in a certain way.
1:19:40
Human race has been reading in a certain way.
1:19:43
It could be right to left, left to right, but it's top-down usually like in a way where there's a sentence and it makes a paragraph, there's a space, there's another We don't We know how to do that.
1:19:51
We know how to consume that. Right?
1:19:52
I think the more you write that way, the better off it's going to be.
1:19:55
Imagine like reading a New York Times article that was just like Sometimes they do really beautiful visual articles, but if it wasn't an article format, it was like a web design page format of an article, you'd be like weird. I can't read this.
1:20:08
I don't I can't absorb this.
1:20:12
I don't know what's important.
1:20:12
I don't know what in what order I'm supposed to really go through this. It'd be weird.
1:20:15
So, I think that we do this on our websites because marketing.
1:20:19
And then we're just kind of making it harder on ourselves.
1:20:20
Yeah, what I'm taking away from you the past few minutes is like marketing professional and it's really just you are communicating to another human being and that human being is somebody like the Uber driver who maybe just started an LLC and they're trying to figure out some place where am I going to how is my team going to communicate as we're going to do this?
1:20:40
And ultimately this comes down to people talking to people and there's all this fluff about business, the ties in the corporate world, all the corporate speak, but fundamentally it's just you're communicating to another human being and do not forget that. That's it. That's it.
1:20:57
And I think business like the idea of wrapping it in business is what makes it hard and makes people stumble with it and it's funny like if business what what makes it hard actually is that there's money involved.
1:21:10
If there's no money involved in a and this is like a hypothetical.
1:21:11
If businesses didn't have money involved, they'd be more fun.
1:21:18
People wouldn't take it so seriously.
1:21:19
They wouldn't feel like they're so at risk all the time.
1:21:20
And I try to think of it that way.
1:21:23
I mean there's money of course, you got to like pay your bills and everything, but if this is more just like a fun thing to do and to make stuff, you wouldn't try so hard and over try to have this message that you want to get out and and and and lather it in bad formats and buzzwords and jargon.
1:21:41
You would just say the damn thing.
1:21:44
Like you're having a conversation with somebody.
1:21:47
We could not have written this conversation out.
1:21:49
I mean wouldn't It would have been worse. Right?
1:21:51
You know, this It's just talking it out is what makes it good.
1:21:54
It makes it clear and direct, I hope. Mhm. Yeah.
1:21:55
You've written four books. Yep.
1:21:58
Getting Real, Rework, Remote, It Doesn't Have to Be Crazy at Work.
1:22:02
Walk me through those four books and why you chose to write those books at those specific moments in time.
1:22:08
Okay, that's a big question.
1:22:10
Um and I don't I don't know if I have a real answer, but I'll work it out, okay?
1:22:15
So, Getting Real was in the early days.
1:22:17
I think we published that in 2006 maybe.
1:22:18
I don't remember exactly when that was, but it was pretty early on.
1:22:22
Um and it was it was like our back in the day um this was basically our method for building software and it was written to an audience of software makers.
1:22:35
Our future books are written to a more broad business audience.
1:22:36
Initially, we didn't have broad business.
1:22:39
We had a software maker audience.
1:22:40
And so, we wanted to basically put our cookbook out there.
1:22:44
This is how I think about it. Right.
1:22:45
So, I think about um I'm inspired by chefs basically.
1:22:49
Chefs, really good cooks.
1:22:53
Um they have recipes which they follow and you would think if they were business, they would keep them close to their chest cuz you don't share your business secrets.
1:23:03
But instead, they write cookbooks and they put their recipes out there for the whole world to see.
1:23:09
They're not afraid of somebody buying that cookbook and then opening a restaurant next to theirs and putting them out of business with the same food.
1:23:18
They're not afraid of that.
1:23:18
They They're afraid of not being known and no one knows who they are and whatever.
1:23:21
So, cookbooks are a way of sharing getting the message out there, getting people to try their stuff.
1:23:26
It's not saying be a cook like me, but here's some recipes you can make.
1:23:30
That's what Getting Real was.
1:23:32
It was a series of recipes for how we think about building software.
1:23:36
And all future books follow the same general thing, but that's where it really started for us was like this is our cookbook.
1:23:42
This is our our These are our recipes for building a business.
1:23:45
Real quick, it hasn't changed that much.
1:23:49
I mean I was You know, as I was reading it, it could have come out a few years ago and you know, there's a few things that would have changed, but not that much. Yeah.
1:23:55
And what's behind that you think that you really had the sort of sense of vision for the company that you wanted to build?
1:24:03
Um we had a way I don't know if it was a sense of vision for the kind of company we wanted to build, but it was a way of doing things that is still every time we've strayed away from it, we've we've gone down the wrong path. Huh.
1:24:14
Keep the company as small as you can. Be pretty scrappy.
1:24:19
Small teams can can move fast, do a lot of things really well that big teams can't do.
1:24:24
Um you know, a lot of these things, the way we launch products with little teasers first.
1:24:30
It was a It was a formula we were developing in real time that worked.
1:24:32
So, like we kept doing it, but also getting back to some of the earliest things we talked about, it just feels natural for us.
1:24:41
We do not try to be this way. We are this way.
1:24:45
And that is why I think we're good at it.
1:24:48
When you try to be a way that you are not, you're always struggling. You're always copying.
1:24:53
And they're I think there might be a an essay in Getting Real about this, but I can't quite remember about copying.
1:25:00
It might be in Getting Real or could be in Rework.
1:25:01
Um The problem with copying is that you might copy someone really well, but you don't know the ideas that went into the thing. So, now what?
1:25:09
That's the problem with copying is it now what?
1:25:11
You copied them until that present moment, but now what?
1:25:16
If you don't have the the the ideas behind what made the thing initially, you don't know where to take it next. And this is what hurts.
1:25:22
And so, I think a lot of people who try to copy a style, it's okay to copy by the way like to learn, but then you've got to find your own way.
1:25:28
And so, I think these books are the result of us have found we found a way early and we've been developing that way, but it's always like what's natural for us. Yeah.
1:25:39
So, yeah, to take I mean if we're going to continue on the road, I mean it's the same idea though.
1:25:41
It's just like as we got bigger, we had new ideas, we saw new things work or not work and we just continued to layer into these and eventually we felt like we had enough material to put a book together.
1:25:51
We didn't set out to write books.
1:25:57
Books are byproducts of us being who we are and being willing to share those things and not feeling like these things are private and proprietary.
1:26:03
I think the business world that we entered back when we started this was like a scared, paranoid, um uh proprietary, secret world of like everything's important, let's patent everything, it's ours, no one can know what we're doing and everything's stealth.
1:26:21
It's like I don't buy any of that for a minute.
1:26:24
I like let's just share it all, let's get it all out there, let's talk about these things and I think that's really ultimately um better for business and it's better for you and then you're honest with yourself and everyone knows you are so they can call BS on you if you're not being that way. It's just healthy. It's healthy. Yeah.
1:26:40
It's an interesting place that we found because like I really admire what you've achieved and accomplished both as a writer and in business and I don't feel like I've done that.
1:26:49
And I want to have achieved and do some of the things that you've done.
1:26:54
Like it's that's very aligned with the vision that I want for my life.
1:26:58
And when I think of that, my fingers clench, I get tight.
1:27:04
I'm like you need to do this. You know what I mean?
1:27:07
And this this inversion that we're talking about here, it it requires a kind of just like surrender, a release, a relaxation that I think a lot of people and I know myself struggle with.
1:27:18
Well, let me give you a little drum analogy because I'm learning.
1:27:22
When I first started, I gripped the sticks too hard.
1:27:26
And when you grip the sticks really hard, you don't play as well for a lot of reasons.
1:27:30
You can't get the same tone, um you don't have as much movements, there's no ghost note.
1:27:34
It's like there's a lot of things that become harder and your hand cramps up so you can't play as long.
1:27:40
And by by relaxing your grip, you get better.
1:27:44
I think that people have too tight a grip on business and think what they need to do is all these other things.
1:27:50
And if you just lighten up a little bit and part of that is not paying attention.
1:27:54
So, I don't read industry news.
1:27:54
I don't pay attention to the com I mean I know who the com competition is or whatever this, but I I don't pay attention.
1:28:00
I don't want to pay attention because then you begin to inhabit other people's thoughts too much and you feel like I got to do it this way.
1:28:10
And I I it's like if I've always like admired It's a weird like I've always like to visit islands where they just like evolved on their own in a sense. Yeah.
1:28:19
Cuz it's just more interesting. Yeah.
1:28:21
Everything's more interesting there.
1:28:22
Because it it just didn't It wasn't influenced by other things and it like had to find its own way and um I feel like if if you grew up that way, like we founded our business in Chicago outside of Silicon Valley.
1:28:33
Had we been in Silicon Valley, we would have been a very different business and I think we would have been out of business. Right.
1:28:39
Because we were all far away and weren't at the parties and weren't in the scene and didn't do all the VC stuff and we bootstrapped and did our own way and didn't pay much attention to that world, we benefited handsomely from it and greatly from it.
1:28:52
Because we just had to find what worked for us.
1:28:54
And if you pay too much attention, you end up doing what you think other people what you think you should do because other people are here's the seven ways to do this and the 10 ways to do this and everything's lists these days and all these success stories.
1:29:04
Most of these people including like everybody Every Everything's held together by duct tape. Right.
1:29:10
Every business is kind of a crazy place.
1:29:13
It nothing's very clear and clean and as it appears.
1:29:17
People are making everything up as they go.
1:29:18
Nobody knows really what they're doing and but there's this this air of like if you just follow this path it's going to be killer.
1:29:25
You're going to be great.
1:29:29
And like I'd pay less attention to that and just do your own thing.
1:29:32
Yeah, it's funny as a as somebody who teaches writing I really wanted there to be like a method, a way of doing things that I could find by doing this podcast and then I could basically like a guru from on high sort of say I have gone and spoken to all the people Yeah.
1:29:53
And I will tell you the exact method.
1:29:55
And I've learned that there just is no method whatsoever. Everybody's different.
1:29:59
Everyone's got their own way.
1:30:01
There's one thing that stands out.
1:30:02
There's just one sentence from how I write all these episodes is you can do whatever you want but whatever it is that you do choose you got to be really really really good at what you do and the only way to do that is to have it be aligned with your nature and who you really are. That's it.
1:30:18
You've got to find the nature of things.
1:30:20
That's probably the thing that in life I've found to be the most useful tool in anything is like understanding the true or trying to understand the true nature of an experience, of a place, of a thing and rolling with the nature.
1:30:33
Anytime you go against the true nature of something you're just battling unnecessarily. So yeah, figure it out.
1:30:40
Find out the true nature of you or it or whatever it is and and and you're going to find yourself there's a there's going to be more ease.
1:30:49
I think you want to get to the place where things do feel easy and we can push ourselves into places that feel hard because we think that it's going to be better if it's harder. Not all the time.
1:31:02
Some things you do have to push yourself through to learn something brand new but then again, let up on the grip a little bit and and relax a bit more.
1:31:08
I think you'll go further. Great script, man. Awesome. So fun. Awesome, dude.
1:31:15
That was really wonderful.
1:31:16
That was a great conversation.
1:31:17
I haven't talked about writing like this forever.