Become a Writer Today

The Principles of a Good Story with Daniel Joshua Rubin

June 30, 2021 Bryan Collins Season 2
Become a Writer Today
The Principles of a Good Story with Daniel Joshua Rubin
Show Notes Transcript

Chicago-based scriptwriter Daniel Joshua Rubin is the author of 27 Essential Principles of Story.

This book stands out because Daniel uses modern examples like South Park and Breaking Bad to describe how storytelling principles work. Then, he explains how writers can apply the principles to writing screenplays, novels, etc.

Daniel describes what it means to live a writing life and how sometimes you need to separate your identity from being a successful writer.

Towards the end of our conversation, we went off-topic and talked about how investing, and the stock market has something in common with a good plot.

 
In this episode we discuss:

  • Deciding on the number of principles
  • Using popular media to convey the principles
  • Should you outline a story first
  • Daniel's writing process
  • How long it takes to write a script

Resources:

Support the show (https://www.patreon.com/becomeawritertoday)

Daniel: If you write a scene, make sure that scene A directly causes scene B, and when you do that from start to finish, it’s just amazing the bang for the buck you get off that one simple principle.

Introduction:Welcome to the Become a Writer Today podcast with Bryan Collins. Here, you’ll find practical advice and interviews for all kinds of writers.

Bryan: What are the principles of a good story?

Hi, there. My name is Bryan Collins and welcome to the Become a Writer Today podcast. If you’re any kind of writer, whether you’re writing fiction or non-fiction, understanding the principles of a good story will help you write something that captivates the attention of readers.

There are a couple of great books that are worth checking out. First is the book Story by Robert McKee. I attended his workshop a few years ago in County Kerry. He’s known around the world. He’s even consulted with Pixar and I definitely recommend checking out his book. Another book is The Art of Dramatic Writing by Lajos Egri.

He’s a Hungarian playwright and that was a book written in the mid part of the 20th century and, although it’s about screenwriting, I think it’s informed a lot of Robert McKee’s work and a lot of the principles in storytelling today.

There’s another great book that I’ve recently come across called the 27 Essential Principles of Story by Daniel Joshua Rubin, who lives in Chicago, and his book stands out because he’s used modern examples like South Park and Breaking Bad to describe how storytelling principles work and how writers can apply them for screenplays, for novels, and so on. It’s always good to talk to somebody about story and I really enjoyed this interview with Daniel.

Towards the end of the interview, we went a little bit off-topic and we talked about how investing and the stock market has something in common with a good plot, like something you’d see in Breaking Bad. One of my key takeaways from this interview with Daniel is what it takes to, you know, live a writing life and how sometimes you need to separate your identity from what it means to be a successful writer versus, you know, just being an ordinary person out and about in the world and that’s something Daniel did and he describes that process at the start of the interview.

If you enjoy the show, please consider leaving a short review on iTunes or wherever you’re listening or you can share the show on Overcast or Stitcher. And you can also support the show for just a couple of dollars a month by becoming a Patreon. I’ll give you discounts on my writing software, books, and courses.

Now, let’s go over to this week’s interview with Daniel and I started by asking him to describe how he got into teaching the principles of story in the first place.

Bryan: So I read your book and I was fascinated by story principles and I can’t wait to figure out how you managed to refine it to 27 but before we do that, would you be able to give listeners a flavor for who you are and how you got into teaching story?

Daniel: Sure. Actually, I started out as a playwright. I was in Chicago writing plays and I was a playwright-in-residence in Steppenwolf Theatre and I did a play then I had a play produced in New York and then one in London and then I took time and went to LA. I was in LA for 11 years. 

I was kind of a journeyman TV writer. I wrote for some shows. I spent a lot of time not writing for shows. Then, I came home from LA and I got back to Chicago and I realized I was really burnt out. I went to grad school at a very young age, I was like 22, and I’ve been writing my whole adult life and I think I was in my mid-40s then and I just took some time off to be a regular guy and one of the big things I definitely love talking about, I won’t drag us into this too quickly, was, but I needed to separate my identity as a human being from being a writer who’s successful and I just wanted to be not a writer for a while. 

So, I took a job running the marketing for an agricultural risk management company and I kinda found my voice again, you know? I realized, wow, I don’t need to ever write again. I have a good job, I’m making money, I work nine to five, I can go home and not think about it. And, one day, I decided, you know, I actually do like writing and I wanna write again and I started keeping a journal of principles for my writing to guide all of my future writing. That book of principles that I started, which had like 150, that evolved into my book.

Bryan: So, yeah, I used to be a journalist years ago and it’s kind of a similar arc to what you described, but I’d figured I wouldn’t write for a while and just do something else and then I —

Daniel: Yeah.

Bryan: — then I discovered that I liked to write and I found my way back to a different type of writing that’s not journalism, you know, writing online and content marketing and so on. So, was that when you decided to write this particular book, or did you start working, the principles drew with students or with people that you collaborate with?

Daniel: Well, it’s funny, I started writing this journal and I was gonna — I have a little writing studio in Evanston, Illinois, which is a suburb just north of Chicago, because I had no intention of being a big shot with a book, like it was just my journal. And then I started thinking, you know, this is probably the stuff that’s good, you know? 

So, on a whim, I called an agent and, sure enough, this agent signed me right away, one of my favorite people in the world, Lisa DiMona, and she sold the book for me, but the idea was always that this would just be my guide to help me write — I always wanted to be a writer, not someone who wrote about writing. I found that I had a lot of passion for it and I don’t think — this is gonna sound so horrible and arrogant because there’s so many amazing, great books on writing, but I think the method that I developed to teach it is pretty effective. Should I jump into that or —

Bryan: Did you — yeah, of course, did you teach it first and then write a book —

Daniel: I was —

Bryan: You were teaching first? Yeah.

Daniel: It kinda happened in — I was using different books that I loved —

Bryan: Yeah.

Daniel: — but I didn’t think they were organized easily for rookie writers because it’s such a hard subject and I was very, very influenced, I had spent some time taking martial arts and that was the greatest experience I ever had with education. 

What I love so much about martial arts is you walk into a dojo and they give you a white belt and you openly get to say to everybody, “I suck at this. I don’t know what I’m doing. I barely know how to tie my belt or do anything,” and you learn a couple of basic moves and then have a ceremony and you get to invite your family and they give you a new belt and you just slowly work your way up and I thought that would be a great way to bring that kind of energy to teaching writing, just slowly develop the craft over time by adding basic principles.

Bryan: So, the book is broken into three acts and each chapter in each act relates to a modern reference and I think this is what stands out about your book is the references are ones that people will immediately recognize, like there’s a South Park reference, there’s a Hamlet reference, and then there’s also a reference to Breaking Bad. So, there’s lots of things that people would have seen recently, not just stuff they might remember from school or from years ago. So, were you journaling about this type of media when you were reading it or watching it?

Daniel: Yeah, I wanted as much as possible, you know, Elon Musk always talks about first principles and how he built Tesla from the most essential principles to creating a car, not, you know, designing by what you need, like you need a steering wheel, you need wheels — I mean, you need a way to move the car, you don’t necessarily need a steering wheel. 

So I wanted to build up from the most essential principles you need to be the best writer you possibly can and I really wanted to make it appropriate for all story, whether you’re talking at a conference and you wanna tell a story, whether you’re telling a joke, whether you’re writing a video game, a graphic novel. I wanted the principles to apply to everything because, nowadays, I think most people, I don’t know that kids coming up are just gonna be one thing so —

Bryan: Yeah.

Daniel: — I wanted the most essential things and, originally, I was telling you I had 150 principles and I got it — I really kept whittling it down and whittling it down and 27 just seemed like a super cool number because that’s — and this is kinda — I’m a little bit of a dark kind of character, but like rock stars always die at age 27 and I found the number — that’s not really a great reason to pick it but —

Bryan: Yeah.

Daniel: — 27 seems to be a really uniquely powerful number. You see it all the time —

Bryan: Well, it fits nicely into three acts, 9, 18, 27.

Daniel: Yeah, yeah. But, really, it was broken up by the classic Aristotle poetics, plot, character, dialogue, theme, and setting. You know, those are gonna carry 95 percent of probably everything you’re ever gonna face if you have a problem as a writer.

Bryan: So, to give listeners a flavor for the principles, perhaps we could talk through one of them.

Daniel: That’d be great.

Bryan: The one that I think stood out to me was the South Park principle so would you be able to describe that one and how it works and how people can apply it?

Daniel: Absolutely. Without a doubt, one of the biggest challenges I see when I get scripts from rookie writers is they kind of meander and they don’t drive — they don’t move forward with purpose. They get boring. So, the South Park guys have talked a lot about this, Matt Stone and Trey Parker. It’s called “Connect with ‘therefore,’ not ‘and.’”

So, if you tell a story, and if you ever hear a little kid tell a story, they’ll say, you know, “Dad, this happened and that happened and this happened and that happened,” and it’s very cute but it just rambles on and on and on and it doesn’t really go anywhere. But if you connect with this happens, and then you say, “Therefore, this happens.” So, the episode I use in the book, an episode from South Park called “Breast Cancer Show Ever” and it’s such a great episode. 

It’s a really deep-seated exploration of human evil and it works because one thing happens which causes another thing to happen which causes another thing to happen, and when you do that, you force your characters to go deeper into who they are and you force yourself to go deeper into your themes and that’s where that came from. If you write a scene, make sure that scene A directly causes scene B and when you do that from start to finish, it’s just amazing the bang for the buck you get off that one simple principle. I’d say that principle gives you more than most grad schools.

Bryan: So, it’s kinda like having the consequences for your actions for the character or for the story event —

Daniel: Absolutely, big time. Yep.

Bryan: Okay. And do you recommend people outline in advance?

Daniel: You know, it’s funny, I do think about that a lot. I’m actually in an argument with one of my best friends who’s a writer who passionately believes that he just writes and he — there’s definitely two strong schools of thought, like I come from theater so I have a lot of playwrights in my brain, but Arthur Miller was fanatic about you need to know your ending and you need to work through an outline before you start writing. Sometimes, he’d worked for a year on an outline. But like August Wilson, Neil Simon, they just wrote. They just let it rip and they shaped it as they went and Neil Simon famously said he finds out what his scripts are about when he reads the reviews. 

But, in my experience, I’m heavily influenced by the great story coach, Robert McKee, and his method I really like a lot, which is have a little pitch, develop a beat outline, develop a treatment, and then write your script. And I find — like I’m working with a writer right now who I love and he’s a great guy, really, he has an edgy script, but he has a couple of scenes in there that simply don’t fit because he writes from the gut and it’s very hard when you write from the gut to, you know what they say, kill your darlings, you know? 

You have those great scenes but they don’t fit in the story and they gotta come out so, for me, if my school was a dojo, we would definitely be “write the outline and then write the script,” but you gotta — the key is, the tradeoffs are, if you write an outline, you can be so mathematical and logical, you squeeze the life out of the story, but the tradeoff of writing without an outline is you make a mess, even though you have a lot of primal gut in it. So, I’m always navigating those two things, but I’m pro outline, I’d say.

Bryan: Give and take. And do these principles work for novels or other forms of story?

Daniel: 100 percent. Absolutely. Whenever I read a great novel — novels give you a little more room to be experimental because you can put the book down so like if Melville wants to spend 50 pages talking about the boat and how the boat was made and the sails and all that stuff, you do have a little more room to be experimental and to go into people’s minds, I think, but, generally speaking, it works for absolutely everything but different mediums have different requirements as far as these things go, I think with a screenplay, unless it’s a super experimental screenplay. 

I always try to avoid absolutes with these things. I would never tell David Lynch or experimental filmmakers not to do what they’re doing —

Bryan: Yeah.

Daniel: — but it definitely works for everything. I see these principles all the time in the greatest novels. You read Thomas Har— I was reading Tess of the d’Urbervilles, I don’t think — I’m not sure I have — that it ultimately made it into my book but like it’s so beautifully structured and all the classic things are in there.

Bryan: So, let’s do another one. Another one is “Clash Expectation with Reality.” I picked this one —

Daniel: Absolutely.

Bryan: — because of the Breaking Bad reference, which a lot of people’s, including mine, favorite TV show of the last few years. Would you be able to explain how this principle works?

Daniel: Absolutely. You know, what I tried so hard to do with my book is get rid of all the jargon, all the academic like speak so like even down to words like “plot twist,” like, well, okay, and my chapter is called “Clash Expectation with Reality” and what that essentially means is you pull the reader into, or viewer, into your character’s world, you get them fully empathizing with the character, and you set up a clean expectation and then that cannot be what happens. So, when a character finds himself in a reality he wasn’t expecting to be in, the character’s in a very heightened state and it’s in that heightened state that you discover who someone is, whether it’s in real life or a character.

So, Breaking Bad, you know, was six years of unbelievably magnificent messing with expectation. So, for example, we all — anyone who’s seen the show probably remembers there’s a scene where Bryan Cranston, I mean, Walter White, goes to see his friend to get some drugs —

Bryan: Yeah.

Daniel: — and he sees, I won’t ruin it but he sees something happening with his friend’s girlfriend and now he is in this heightened state where the action he takes will tell us who he really is as a person and he does something that significantly breaks bad in that moment, as I’m sure you remember what it is.

Bryan: I do, yeah.

Daniel: So, yeah, so it’s always — the most important thing about these principles is they are about helping you better express who you are and drive deeper into the truth of your characters and your themes. They’re never principles just to like check a box or — we’re not baking cakes. We don’t care about formulas. We care about truth and the principles force you to dig in a deeper truth and that both — the two you picked are definitely two of my favorites, like if I had to pick five for this book, I think those would, without a doubt, be two of them.

Bryan: So if I pick up your book, how would I go about using it? Do I pick a problem I’m having with my script or is there some other approach I should take?

Daniel: You know, it’s funny, I was just thinking of pitching a guide book to go with this book about that to help develop the process, but I’m very sensitive to, having gone through grad school and having gone through an undergrad degree in writing, I’m very sensitive to writers being forced into boxes.

So, the principles are given with — I take a lot of pride in the book having, if you need a guide to follow, I think you could work through the first section on plot and pretty much craft a narrative just kind of doing each of those exercises, you know? Ask a dramatic question, think about the different possible endings, resolve your dramatic question, you know? For me, the simplest way to think about story is ask a dramatic question, answer it. So, will Hamlet kill the king? Yes. Keeping it super simple. But if you’re more of a character-driven writer, I think you could pop open the whole section on character and build one that way by, you know, just crafting — a chapter called “Earn Transformations” where I think some people are just driven by watching how someone goes through a change. The example in that chapter, I think, is Alison Bechdel’s graphic novel, Fun Home, which is really not so much plot driven as just her journey toward dealing with her father. 

So, it’s super flexible is my answer, like I think it’s meant to be able to pick it up, use common sense, and story doesn’t come out neatly usually for people, you know? You have an idea in the shower about a theme, you have a memory of a defining experience from your life and you build from there so it’s meant to have both enough guide to help you get from A to Z if you need a helping hand but a lot of flexibility built into that. Sorry, that was a long-winded answer but…

Bryan: No, it makes sense. Do you spend — like you mentioned you were a screenwriter and then you left that and then you worked on this particular book. Do you spend your time these days working with other writers or do you write scripts still?

Daniel: It’s funny, I’m hardcore now back into my own writing. I have three scripts that were eating my guts with some fava beans and a nice chianti, as Hannibal Lecter would say, so they — and I really, really am trying to use my own book. I mean, like my dream is to be — they must exist out there but I really do want to prove that this — to be honest, I don’t think this book is ever gonna get the respect it deserves. 

Fair or not, people think, “Oh, this guy writes about writing because he can’t write,” and I get it and I understand that. I happen to think that’s total crap but it’s the way it is. So, I’m working on one screenplay and two plays that are — all three are inspired by a significant defining experience in my life and I didn’t set out to develop the stories that way and I’m seriously using the book to guide my choices so —

Bryan: Yeah, yeah.

Daniel: — and then I teach when I’m not writing. So, it’s kind of a dream situation to write in the morning, think about, you know, all the challenges I’ve had —

Bryan: Yeah.

Daniel: — bring those lessons to my students and — so as soon as COVID, God willing, we get past this thing, I plan on opening up my school.

Bryan: Okay, okay. So, you probably collaborate online or work online with your students at the moment.

Daniel: Yes, I do a lot of phone consulting. I don’t have a ton right now. I like doing workshops better because it’s — one-on-one coaching is really hard.

Bryan: Yeah.

Daniel: It’s really tough. You gotta be a nasty, nasty bastard to get people to — it’s just the marketplace is so competitive that if people want to have a prayer of selling a script, it just has to be world-class or it’s just not gonna make it.

Bryan: Yeah, okay. And what about your actual process for writing? Because you mentioned, and this is something that I do, you use journaling to come up with these principles. I use journaling as a way of finding an entry into non-fiction books and I used it recently to write kind of a story-driven parenting book. How does journaling inform your writing for scripts?

Daniel: I think it’s infinitely vital. I mean, I’m a big fan of — I think one of the biggest mistake rookie writers make is I don’t think they go deep enough from the start and, again, this is a controversial opinion. I know Toni Morrison, when she used to teach writing, just said start from anywhere and you’ll get where you need to go.

For me, I’m a little more — the process I encourage my students with is a little more, “Let’s get to the deep stuff like right away.” I recently worked with a young woman who had a sexual assault and she wrote a script that I think is fantastic that’s based on — and it was very healing for her to confront that but, for me, when someone’s writing from their gut and from a conscious knowledge of some of the issues they’re dealing with, I think they tap into deeper stuff. You feel it, like if you look at — one of the books I talk about in my book is Junot Díaz’s The Brief Wondrous Life of Oscar Wao, which we found out later is very much inspired by his encounter with being abused as a child and there’s just a greatness to that, in my opinion. So, journaling is huge. I think it’s just — not having a journal if you’re a writer is, to me, just insane.

Bryan: What does your journaling process look like these days?

Daniel: It’s funny, not to sound like a Mr. Punk Rock Rebel, but I’m so naturally rebellious that I don’t even like me to tell me things to do. So I have index cards and I have journals all over the place and I don’t have any rigid method, I just can’t, but I always have tools to — I finally figured out how to do voice dictation on my phone. I’m kind of becoming a geezer. So I have my notes but I have an index card collection, notebooks, and audio files and I keep them pretty — I know you do something with Evernote, I actually wanna look into that. I think you’re an Evernote fan, if I’m —

Bryan: I use Evernote but, for journaling, I use Day One. It’s kind of a dedicated journaling app for — I think it’s for Windows and Mac but I find it’s quite good. I also use a method called the zettelkasten or a slip box which involves writing a single idea on an index card or as a journal entry and then you write your reaction to that idea and then you interlink them in some way.

Daniel: Yeah, I like that. I gotta up — to be honest, I gotta up my journaling game.

Bryan: Yeah.

Daniel: So, I wanna dig into your stuff. I see —

Bryan: Well, check out Day One app for journaling. But, to be honest, I mean, as you know yourself, the tool doesn’t matter that much. It’s more about just turning up and writing for a couple hundred words in the morning before you go on with the day. 

Yeah, so I find that works quite well. Like you strike me as someone who’s very creative, I can see musical instruments in the background and we were talking about how you’ve written quotes on your wall. How do you organize and arrange all — Yeah, it’s pretty impressive. I know listeners can’t see it but there are like dozens of quotes written in, it looks like black felt pen, like there’s a quote from Conor McGregor.

Daniel: Yes.

Bryan: So, how do you go about like arranging all of your ideas if they’re in audio and index cards and on the wall and everywhere else?

Daniel: That’s a good question. I love all the stuff about being a writer. I love notebooks, pens. I love going to the store. I just have a — I have a ton of notebooks, I have a place to file, a card file for my index cards, I have loose-leaf paper, and I have my notepad on my iPhone, but I do religiously catalog everything too —

Bryan: Yeah.

Daniel: — because I just find it’s just — you have an amazing idea and now forget about it in the chaos of life. And I return to them again and again but I organize them by idea and by — I’d say by idea for a script and by theme.

Bryan: Okay, and does it take you long to write a script?

Daniel: Yeah, I’m realizing that one of the great inspirations for me during my book, I believe that my book took me like four long years, I’d say, like really full time, I had to quit my job and I found, for me, that when I was researching, that Stanley Kubrick, who’s one of my super idols, you know, he didn’t make a lot of films but I think everyone he made was pretty great and I’ve decided that works better for me. 

I gotta give myself time. I’m not trying to win awards for quantity and I don’t think I’m a natural genius, by any means. I gotta work my living ass off and I gotta stick to it. So, I’m giving myself at least 6 to 12 months for a script, but I’d like to speed that up, if I could, but also that deals a lot with whether or not you make your money as a writer and, for me, I don’t.

Bryan: Okay, okay.

Daniel: It’s not my main thing.

Bryan: Okay. What else do you do, if you don’t mind me asking?

Daniel: I don’t. I love yapping about this. I drive my wife nuts. But, to be honest, I’d say I’m an individual investor.

Bryan: Okay.

Daniel: I found — one of the most amazing things is I quit my job, best job I’ve ever had, and I quit my job to do this book and I started noticing tremendous similarities between a great stock and a great investment and a great story. There’s big differences but there’s tremendous similarities and it sounds kind of douchey to say this but I had a lot of success because of that. And maybe there were other factors, I might have just got lucky, to be honest, or maybe certain things happened with the COVID crash but my money now is more from investing, which is awesome because —

Bryan: Because it gives you free time then to write —

Daniel: And write whatever the hell I want.

Bryan: Yeah. Out of curiosity, what’s the — because they strike me as two things that have nothing in common so, I mean, I do invest in stocks as well but I don’t think about writing —

Daniel: Can we talk about this? Can we go there?

Bryan: I think I might need a different show for that.

Daniel: Okay.

Bryan: So what do you see is the similarities between the two?

Daniel: Okay. In all seriousness, if you look at one of the greatest stocks of the last 20 years, it’s Netflix —

Bryan: Yeah.

Daniel: — and Netflix had a CEO who had a simple vision to let you see films and TV shows online. So, you look at him as the hero of the story and it’s really like can Reed Hastings get Netflix to many millions of people? It’s a very simple, clean story where the hero has a clear objective and there’s a clear, dramatic question, you might say, can he get 10 million viewers, you know? 

Back then, it was like Blockbuster’s gonna kill them and Walmart’s gonna kill them and Amazon’s gonna kill them so you could look at the competition as the antagonist of the story. The main difference, though, between a work of fiction and a stock story is a great stock story is it’s very easy to imagine the hero to win but we wanna see our characters in fiction get tortured. I mean, we like to see, you know, Frodo Baggins get beat up by a spider, stabbed by a stone golem, get his finger bitten off, I mean, all kinds of things so we can find out about his character so that’s some of the ways I use —

Bryan: Okay, so you’re investing based on the qualitative investing and based on the story behind the stock rather than a fundamental or technical analysis or numbers?

Daniel: Well, there’s a lot of, there’s a million guys doing amazing quality, you know, numbers and math. I couldn’t do math to save my life. I can’t even do long division. 

Bryan: Yeah.

Daniel: But when I see a hero or a CEO of a company and I think this guy really has the qualities I like to see —

Bryan: Yeah.

Daniel: — I invest with that guy and it’s been very, very successful.

Bryan: So, you must be pretty fond of Elon Musk, so, I mean, he’s the ultimate hero of the stock market at the moment.

Daniel: It’s so funny that you say that. I love him. How could you not be in awe of what this man has achieved? But I actually sold all my Tesla when I felt the story went off the rails when he was getting involved in submarines in Thailand, he’s sending rockets to Mars, he’s dating, you know, musicians, and I went, “This is crazy,” but he’s a one-of-a-kind human being but he’s exactly not what I would invest in, personally. But, again, not because I don’t love him, he’s just too complicated —

Bryan: He is complicated —

Daniel: — and too much drama.

Bryan: There’s a lot of —

Daniel: There’ll never be another guy like him, in my opinion —

Bryan: He’s a master at getting attention for his companies.

Daniel: Super genius, without a doubt.

Bryan: So, does an asset like — I know this is a bit different story now, but just curious, does an asset like —

Daniel: No, no, I love —

Bryan: Does an asset like Bitcoin have any correlation with storytelling? Because there’s no — technically, there’s no hero with something like Bitcoin.

Daniel: Yeah, to be honest, for me, I’m actually a big — it sounds so corny but I’m a big human guy and I feel like I understand people —

Bryan: Yeah.

Daniel: — and I look for a CEO who is doing the work he seems meant to do —

Bryan: Yeah.

Daniel: — so like there’s a guy who runs a company, Jeff Lawson runs a company called Twilio, which is a very popular stock and, long story short, he helped invent AWS, Amazon Web Services, so you know the guy’s a brilliant tech guy and then he thought, “I’m gonna move into extreme sports because that’s gonna be hot and popular,” and then he realized, “Oh, God, I hate extreme sports. I’m a nerd and this is not for me,” and then he just took some time off and built the company that he was meant to build, which is Twilio, which facilitates communication in apps. 

So, when I see that, when I see a brilliant guy who’s got a proven track record and he’s doing the work that he’s meant to do, that’s when I — and then when my math guy is telling me, “Oh, yeah, the numbers are great,” then I know I’ve got something really good.

Bryan: Okay, okay. So, how does that work in — I was thinking of turning it into a book one day that if you did something creative in the morning and then in the afternoon, you do something that helps you, you know, earn a living or make money, that’d be a nice balance to have because you can improve at your craft —

Daniel: Absolutely.

Bryan: — and then you’re also providing for yourself. Does your investing take up much of your time during the day or is it more something to keep an eye on in the background?

Daniel: It can be really, you know, I don’t know if you’re familiar with the book, The War of Art, by Steven Pressfield —

Bryan: I am, it’s a great book, yeah —

Daniel: Yeah, and he talks about resistance and it’s like this force that has all kinds of — it’s almost got a consciousness which stops you from writing. The stock market’s really dangerous. It’s got money, it’s got stakes, it’s got drama, it’s always changing, and I have lost many a good day of writing because I had to check a stock —

Bryan: Yeah.

Daniel: — so, to be honest, I’ve now got my portfolio where I’m happy with it and I’m just kinda gonna put it on autopilot —

Bryan: Okay.

Daniel: — and if something big happens, I’ll check on it but, to be honest, it’s a major issue where I’m trying to think, you know, now I wanna be fully invested in writing but it’s, man, it’s a hard life. Like it’s — I think the big thing I would love to say to your listeners is I do think living the writing life and feeling all the feelings you have to feel to be a great writer is really hard. It’s really hard and you’ll do anything not to do it. Like one day I wanna write a book called How to Not Write Your Way to Greatness because —

Bryan: That’s a good title.

Daniel: — I have a bench — I’m looking at my weights next to my desk, I’ll do — like any writer, I’ll do anything not to write. When you get a workout in, it’s like, “Wow, let me do some benching rather than deal with my deepest problems and fears and —”

Bryan: A thousand words, yeah.

Daniel: Yeah.

Bryan: Yeah, no, that makes sense. I think I’ve done the same myself. Where can people learn more information about you, Daniel, or where can they read your book?

Daniel: I have a website called story27.com —

Bryan: Yeah.

Daniel: — and I have a totally free, I made 27 short video intros to each chapter and I feel great about those. I think you can get, totally free, you don’t even have to buy my book, although I hope you will, but, really, it gets to the heart of each principle and I just do it in three minutes. You do one a day and — I’m a little negative toward grad school, to be honest. Charging people $200,000, $150,000 to do this stuff is madness to me. I actually have a daughter who’s a young filmmaker and I’m trying to steer her away from grad school unless it’s like a super top one. But I think you just need principles, guts, and time. That’s, by far, the biggest thing. Just —

Bryan: Good advice. Yeah, I don’t think you need an expensive postgraduate to do something like that. 

Daniel: Oh, God, no. Lord, no.

Bryan: Well, thanks for your time, Daniel.

Daniel: Thank you so much for having me. I really enjoyed it.

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