#139 Nicolas Cole, Co-Founder of Category Pirates and Ship 30 for 30 | Favorite Books and Writing Tools, Enduring Boring Things, and Why Great Writing Changes the Reader

Listen as we decode favorite books, writing tools, and the advice he’d give his younger self with Nicolas Cole, Co-Founder of Ship 30 for 30 and Category Pirates. We also cover why all great writing changes the reader and how to endure the boring things that are required for success in anything.
Last updated
August 13, 2023
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#139 Nicolas Cole, Co-Founder of Category Pirates and Ship 30 for 30 | Favorite Books and Writing Tools, Enduring Boring Things, and Why Great Writing Changes the Reader


About the Guest

Nicolas Cole is one of the most-read writers on the Internet. Over the past decade, he’s written over 5,000 articles online and ghostwritten for over 300 Founders, C-level executives, NYT best-selling authors, and Grammy-winning musicians. He’s also the Co-Founder of Ship 30 for 30, which is one of the largest cohort-based writing courses online, as well as Typeshare and Category Pirates.

Nicolas is also the author of numerous books, including The Art and Business of Online Writing: How to Beat the Game of Capturing and Keeping Attention, and his latest, Snow Leopard: How Legendary Writers Create A Category of One.

Nicolascole.com | Twitter | Ship 30 for 30 | Typeshare


Episode Guide

Nicolas Cole shares the lessons he’s learned as one of the internet’s most-read writers, including why he’s fascinated with reverse engineering written work—from James Patterson novels to Twitter threads—into templates writers can use, why all great writing changes the reader, why his superpower is his ability to endure boring things for longer than others, and so much more.

“It takes you a really long time to realize that great writing has very little to do with you. It will change you in the process. It can be about you, yourself, your heart, and your story. Everything can be in it, but has to ultimately be about the reader.” — Nicolas Cole

Nicolas Cole’s Favorite Books

Nicolas shared his all-time favorite books including:

The Boron Letters by Gary C. Halbert

  • The Boron Letters is a series of letters by history’s greatest copywriter Gary C. Halbert, explaining insider tactics and sage wisdom to his youngest son Bond. Once only available as part of a paid monthly premium, The Boron Letters are unique in the marketing universe and now they are a bona fide cult classic among direct response marketers and copywriters around the world. The letters inside are written from a father to a son, in a loving way that goes far beyond a mere sales book or fancy "boardroom" advertising advice... It's more than a Master's Degree in selling & persuasion…it's hands-down the best SPECIFIC and ACTIONABLE training on how to convince people to buy your products or services that I have ever read. Nicolas Cole loves this book because it’s a study of “one of the most legendary sales copywriters ever.”
  • Buy it now: Print | eBook

The Gary Halbert Letter by Gary C. Halbert

  • While the easiest to purchase book by legendary sales copywriter Gary C. Halbert is The Boron Letters, you can also purchase the full archive of Gary’s paid direct response newsletter—which he used to literally mail to subscribers. Nicolas keeps a copy of both Volume I and II of The Gary Halbert Letter in his house and goes through it regularly for sales copywriting inspiration.
  • Buy it now: Special Binder Edition 

Portnoy’s Complaint by Philip Roth

  • Portnoy's Complaint is a 1969 American novel by Philip Roth. The novel tells the humorous monologue of "a lust-ridden, mother-addicted young Jewish bachelor," who confesses to his psychoanalyst in "intimate, shameful detail, and coarse, abusive language." Many of its characteristics such as comedic prose, themes of sexual desire and sexual frustration, and a self-conscious literariness went on to become Roth trademarks. In 1998, the Modern Library ranked Portnoy's Complaint 52nd on its list of the 100 best English-language novels of the 20th century. Time included this novel in its TIME 100 Best English Language Novels from 1923 to 2005. Nicolas considers Portnoy’s Complaint one of the most transformative books he’s ever read.
  • Buy it now: Print | eBook | Audiobook

Related Episodes

If you enjoyed this episode with Nicolas Cole, don’t miss our other interviews with writing and category creation experts:

Go Deeper on Writing & Category Creation


Daniel Scrivner (00:00):

Hello, and welcome to another episode of 20 Minute Playbook by Outlier Academy, where we decode what the top 1% of people, we're talking iconic founders, renowned investors, bestselling authors, and outlier thinkers have mastered, and what they've learned along the way.

Daniel Scrivner (00:14):

In each episode, we dive deep to uncover the tools, habits, ideas, and hacks that we can all apply in our own work and lives, all in about 20 minutes. I'm Daniel Scrivner, and on the show today I'm joined by Nicholas Cole, who is one of the most reed writers on the internet.

Daniel Scrivner (00:29):

Over the past decade, he's written over 5,000 articles online and ghost written for over 300 founders, C-level executives, New York Times bestselling authors, Grammy winning musicians, and more. He's also the co-founder of Ship 30 for 30, which is one of the largest cohort-based writing courses online, as well as the author of numerous books, including his latest, Snow Leopard, How Legendary Writers Create a Category of One.

Daniel Scrivner (00:54):

You can find a searchable transcript of this episode as well as our episode guide with ways to dive deeper into the books and ideas we cover at outlieracademy.com/139. That's outlieracademy.com/139.

Daniel Scrivner (01:08):

Please enjoy my conversation with one of the most read writers on the internet, Nicholas Cole.

Daniel Scrivner (01:13):

Nicholas, I am thrilled to have you on 20 Minute Playbook. Thank you so much for joining me today.

Nicolas Cole (01:18):

Thanks for having me, always a fun time.

Daniel Scrivner (01:20):

That's right, always a fun time. Second time on. Second time on. Hope to make it three at some point next year.

Daniel Scrivner (01:25):

Let's jump right into the questions. I'd love to start by asking about a recent fascination. What have you been obsessed with, fascinated by recently? What can't you stop thinking about?

Nicolas Cole (01:35):

I'm going to do a quick shameless plug, but it's the honest answer, which is I co-started a software company about a year ago called Typeshare, which is all focused on giving writers templates to use to start writing online.

Nicolas Cole (01:54):

And it was a really basic idea. At first, we were like, Okay, I think we can help reduce some friction by creating these templates for people. And basically what's happened is over the past 12 months now, I cannot stop seeing templates everywhere.

Nicolas Cole (02:08):

I now firmly believe that every single piece of writing ever created can be reverse engineered into a template. And in order to do that, you have to really understand all the little pieces.

Nicolas Cole (02:21):

Obviously I've writing for a long time. In order to understand how templates get assembled, there's a lot of working knowledge that goes into it, but now I just can't stop. And everything I read and everything I pick up and everything I look at, every headline, every Twitter thread, everything, all my brain's doing is just reverse engineering what would that look like in the form of a template? So that's my current obsession and fascination.

Daniel Scrivner (02:43):

That's fascinating, is the idea there you're thinking about that because you're thinking about adding more templates to Typeshare, or is it just a new way that you're seeing the world and it's changing how you think about creativity?

Nicolas Cole (02:54):

Well, it's both. I really want to provide more writers with templates so that more people feel comfortable starting to write.

Nicolas Cole (03:03):

Looking at a blank page is probably one of the most terrifying things for most people. But more importantly, what it's changing about my own writing process is instead of sitting down and taking the, I'm just going to let the creativity magically come out of my fingertips approach, it makes me realize how much faster you can produce quality when you understand which quote unquote template you're using.

Nicolas Cole (03:30):

Recently, I went through and took a James Patterson mystery novel and reverse engineered the whole thing into a template, and I did it in an hour. And it made me realize, Oh, wow, if you really understand what you're looking at, this whole thing is built like a Jenga tower. And if you get how the pieces click together, then when you sit down you're not asking yourself, Oh, what's this next magical idea that just appears?

Nicolas Cole (03:59):

You just go, Oh, well this is the section where I say this type of thing. So what's that? And all of the speed to idea is just exponentially faster, it's really cool

Daniel Scrivner (04:09):

To make a parallel. So my background's in design, one of the things that you learn if you do front-end visual design is there's really two levels that you need to do great design work on. One is structural, that's typically called UX, and that will be it's largely sometimes somebody thinking in terms of wire frames, which is actually very similar. It's a template. It's literally just boxes and squares and how it will be laid out in hierarchy.

Daniel Scrivner (04:31):

And then there's the visual design once you have that, and the thing that sparked in my mind is as a designer, if you don't have the structure figured out and you're trying to execute, you actually have to bounce between what am I saying and how do I do it? And does this look nice? Is this the right way to do it?

Daniel Scrivner (04:46):

But then at the same time you're like, Is this the right place on the page? So it makes a lot of sense to just separate those two things. There's the execution and expression from the structure and the logic. So it seems like the template is the structure and the logic.

Nicolas Cole (04:58):

Okay, yes. You just vocalized that so much better than I did. But yes, I forgot that your whole background was in design, because the idea for this came from Canva, so Canva completely removed the barrier to entry for all of these people. And now I don't have a design, I couldn't design a box.

Nicolas Cole (05:22):

That is not a skillset I have, but even I can go onto Canva. Why? Because they removed the barrier to entry of needing to know all of these advanced skills. So the more that I've taught writing and I continue to mentor other writers, I was just like, Okay, well, it's the same thing.

Nicolas Cole (05:37):

If you're a writer and you give someone a blank page, they're not going to know what to do with that. You need to give them some sort of shell to color in. And now that I've unearthed this rabbit hole, it's like I can't turn it off. It's everywhere.

Daniel Scrivner (05:51):

Is this your next book?

Nicolas Cole (05:53):

It's going to be a book. It's going to be a course. It's going to be a zillion... I went to school for fiction writing, and I think about I valued my college experience. It taught me some things. But I look back at that and go, If someone had given me 50 templates when I was 19 years old, how different would my trajectory have been?

Nicolas Cole (06:16):

And instead me, like a lot of writers, you figure that out on your own. You're like, All right, well I'm going to create...

Nicolas Cole (06:22):

Most writers don't even realize this, but when they sit down to write they already have templates in their head. Because they've been doing a certain thing for so long. So they go, Oh, okay, well now this is where I say this. This is where I organize it this way. So it's already happening intuitively. It's just my realization is for the vast majority of people who are trying to start, you don't have that tool set yet. So how do you accelerate that?

Nicolas Cole (06:46):

Well, you just go give them 50 templates and now they have it. It's Canva for writers.

Daniel Scrivner (06:51):

I love, love, love the idea.

Daniel Scrivner (06:54):

Obviously you've written many, many books, so I'm going to try to ask you to recommend books without recommending your own books in a second. But one of the things I love to ask guests about is for their favorite books. And I think for you, it would be interesting I think if you could share any writing books or just writers that you especially enjoy reading, or anything that's helped you as a writer. And then separately, you obviously are an entrepreneur in many, many, many regards. So just anything that's been helpful for you on the business side.

Nicolas Cole (07:18):

So I have some creative answers here. So the first is, I guess it depends on what genre.

Nicolas Cole (07:25):

I have it here in my office. So one of the most legendary sales copywriters ever, his name's Gary Halbert. And a couple years ago I was scouring the web because a mentor of mine had told me, You got to go back through and read all of Gary Halbert's sales letters. And I found I think his site or this site is owned by his family now, the family estate I guess.

Nicolas Cole (07:50):

And what they did is they assembled... He had this direct response copywriting newsletter by mail. He would mail it to people. And they took all of the letters and they assembled them into this is one of two massive three ring binders with hundreds of these letters in there. And it is, the only way I can describe it is Gary Halbert is what would've happened if Hemingway had discovered business.

Nicolas Cole (08:18):

He writes the same way that Hemingway writes in a very terse, minimalist way, but it's all geared around how to get people to buy stuff. It's really, really fascinating. And I've probably learned more from reading all these old marketing letters than anything. So that's my first recommendation.

Nicolas Cole (08:36):

My second is if you haven't read Portnoy's Complaint by Philip Roth, that was one of the most transformative books for me. I don't even know how to describe it, it's hilarious but it's extremely well written and smart. It's fictional, but he was Jewish. And so it was a pseudo memoir of growing up in a Jewish household, overbearing mother, strict but aloof father.

Nicolas Cole (09:03):

And that tone, the tone that book is written in, I think is one of the most eloquently and perfectly sculpted, sarcastic, but smart tones I've ever found in literature. And so I reread that book probably once every two or three years, because I just think the way it's written is so incredible.

Daniel Scrivner (09:24):

Yeah, amazing. After this, I'm definitely going to go look up and try to buy those George Halbert direct response letters.

Nicolas Cole (09:30):

Gary Halbert.

Daniel Scrivner (09:31):

Sorry, Gary Halbert. Thank you, that's obviously going to be helpful. I have at home a massive reference library for design stuff. And one of the favorite things, I have a couple of things, but one of them is a book of all of the old VW ads from the 1950s and 60s, just because they had a run there. I think that was a very unique moment in time in terms of advertising, but just the way that they brought together writing in visuals, I haven't seen anyone else do it outside of Apple.

Daniel Scrivner (09:56):

And Apple doesn't really do that anymore, but they used to be very playful with the interaction of copy and design. And then the other one is I have a book of 1950s ads that's part cringeworthy because obviously everything has changed in terms of how we view roles in society and work and all of that, but it's just a really cool moment in time. I really like that style. Anyways, so I love those answers.

Nicolas Cole (10:15):

There's a bunch. Yeah, on that note, the Ogilvy on advertising is a bit similar, and that's a great...

Nicolas Cole (10:21):

I'm a huge believer in going back and studying old stuff.

Daniel Scrivner (10:26):

Well, I just think, yeah, for me, I guess the way I think about it is it just is flexing different... Well, one, it opens up your mind into different ways that you can execute an idea, which is really powerful. Because no matter what you do, whether you're a writer or a designer, working that part of your brain of how do you get out of what you're comfortable with and shake up your style a little bit and challenge yourself is really important.

Daniel Scrivner (10:48):

But then the other one is just to your point, there are certain people that have mastered a medium. And it pays huge dividends to go back and just look at what they've done and just take it in. And I think one of the beliefs I have is that everything's connected. So I'm sure for some people listening, they might think, Oh, Gary Halbert, how's that going to connect to the tweets that I want to write or the threads that I want to write? It'll happen. It'll happen. It all connects.

Nicolas Cole (11:09):

Yeah, there is some gems hidden in that stuff. There's a reason why all the best sales copywriter go study all the guys that were crushing it 20, 30, 40, 50 years ago.

Daniel Scrivner (11:20):

I want to switch up and ask a very different question. If people listening could shadow you for a day, so be with you from the time you wake up all the way into when you go to sleep. Setting aside, that'd probably be a little bit creepy. What do you think they would be most surprised by? And what I'm trying to get at there is is there anything about your habits, your routine, the way that you work, the way that you do different things during the day that might surprise people listening?

Nicolas Cole (11:46):

I'll give you two answers. One, I think in a very genuine way, I think most people would... I think they'd be pretty bored, to be honest. They'd be shocked at how much I just sit and write. Today is a perfect example. Knew we had this at 4:00 PM my time. I am not exaggerating, aside to get up and grab my lunch, I've sat here and written since 8:00 AM.

Daniel Scrivner (12:11):

That's not a bad thing, that's not a bad thing.

Nicolas Cole (12:12):

It's an amazing thing. I remember when I was younger and I would think about what it would be like to be a full-time writer, and somehow you romanticize this thing where somehow you're writing a lot and yet your life isn't boring and you're not sitting down and writing at the same time.

Nicolas Cole (12:26):

And it hasn't been until the past few years where obviously this is my whole life and my livelihood, and from the outside it's boring. I'm just sitting here writing.

Nicolas Cole (12:38):

I'll say the more unconventional answer is I used to be a pro gamer as a teenager, I played World of Warcraft professionally. And an interesting quirk that I can't seem to let go of is I still will have old World of Warcraft videos playing on YouTube in the background. And I don't know why, but there's something very calming and soothing about that.

Nicolas Cole (13:00):

I think it just reminds me of being a kid. It just makes me feel like I'm a kid. So if someone was watching me, they'd see me tab back and forth between writing and these 2008 gaming montages.

Daniel Scrivner (13:13):

That's definitely surprising, that checks the box.

Nicolas Cole (13:17):

And so I feel like that's a good, genuine, honest answer to that question.

Daniel Scrivner (13:20):

No, I love it. I want to ask one follow up question. In terms of days like today, you sit down to write, I was listening to a book recently, Stephen Pressfield has a book, I forget one of...

Daniel Scrivner (13:31):

You won't be wrong by just looking up his name and ordering any one of his books. But there's one book in particular, and he's talking about creativity. And he talks about when he stops for the day and he quotes other writers, and some writers say to stop when you start making mistakes. Some writers say to stop when you know what's going to happen next. Some writers say to leave something in the well for tomorrow.

Daniel Scrivner (13:50):

Do you have any approach to when you decide to stop working in a given day?

Nicolas Cole (13:55):

I stop when my fiance says It's time to stop, that's the answer right there. It's time for dinner, you need to stop.

Nicolas Cole (14:04):

It's funny, because I've read a lot of that same advice. I've tried the Hemingway stop in the middle of a sentence. There was probably a year or two where I took that extremely seriously and I would literally force myself to stop in the middle of a sentence thinking that was going to guarantee that that was the magic.

Nicolas Cole (14:20):

In general, I would say a rule I try to live by is if you can feel that you're flowing on an idea, try and not disrupt that. Push it as far... And usually you can feel when you're like, All right, I've gotten what I need to get out, I can pick this up tomorrow. But I've learned that it's a pretty big mistake. If I really connect with an idea, I start and then I just stop. The next day it's not the same.

Daniel Scrivner (14:46):

Yeah, so well said. I want to ask one other question around your skills and talents. And the way I typically ask this is to have you think of areas where you have an edge or a superpower. And superpower might seem like a super loaded term. We've spent a bit of time talking, I think you actually have a lot of strengths that are pretty unique.

Daniel Scrivner (15:05):

When you think about your superpowers or areas where you have an edge, what comes to mind? And then how does that show up in your day to day life and work?

Nicolas Cole (15:12):

I will definitely say I think the biggest one is my ability to endure very boring things if it means having some sort of advantage. I've never thought of myself as a naturally talented writer. There were a lot of teachers in school that told me this is not the path for you.

Nicolas Cole (15:32):

But the one thing that I know that I have is I am willing to sit there and endure it for way longer than the average person, and I think that comes from my years as a gamer. I would just sit in front of my computer and grind and grind and grind and whatever I had to do. So I think the endurance is a big piece.

Nicolas Cole (15:53):

And in the past few years I've really realized that I'm very good at understanding how things are assembled.

Nicolas Cole (16:00):

Again, I think it goes back to gaming. It's my recent fascination with templates. I can look at something and understand how it needs to be built. I might not be the most eloquent at it or it might take me longer to develop that part of it, but the building, how things get assembled I think is a big reason why I've been able to write and publish as much as I have.

Daniel Scrivner (16:24):

Yeah, those are super interesting. I want to switch tax here a little bit. You're a prolific writer, you're the author of snow leopard, how legendary writers create a category of one, which just came out. I highly recommend everyone listening pick up. We're about to do a long form interview all about that book.

Daniel Scrivner (16:41):

So I want to ask a couple of questions around writing, and where I wanted to start, and I'm sure this is a question that'll probably bore you as soon as it comes out of my mouth, is writing process. You've talked a little bit about just this act of, well, one, if there is flow, making sure that you take advantage of that and don't stop for any other reason if you don't have to.

Daniel Scrivner (16:58):

And then two, just this ability to sit and write and to endure. If you can describe for people, is there anything else that's unique that might be applicable for others that other people can learn about your writing process? Or is there anything that you've learned, maybe another question.

Nicolas Cole (17:13):

Yeah, it's hard because it's such a loaded question. There's so many parts that go into it. The simplified version that I've been thinking about a lot lately is this idea of first, do you know what you should be focusing on? So there's multiple pieces here, and I'll walk through each one. So most people go, I don't know what I should be doing. I don't know what I should be doing. So they can't take action because they don't know.

Nicolas Cole (17:44):

The second layer is you go, I know what I should be doing, but I'm choosing not to. And then there's a whole bunch of beliefs and things you got to unpack when you get there. And then the third layer is, I know what I should be doing and I'm doing it. So you're at least taking the action, but you might not be doing it as well as you could.

Nicolas Cole (18:09):

So you have more to learn on the execution side. And then there's the, I know what I should be doing and I'm doing it as best as I can. And so all you can do is wait for time to catch up. And so in terms of writing process, to me it starts with where are you in those four levels? And depending on where you are, you're going to focus on very different things. Opposed to the average person just goes, Well, what do I need to do to just become a great writer?

Nicolas Cole (18:39):

It's like, well, step one, are you even doing it every day? If you're not doing it every day, you have a habit problem to solve first rather than we can't really get into the headlines and all the nitty gritty stuff. Versus someone who goes, I'm doing it every day and I'm blocking the 90 minutes, but I need some help understanding how do I spend those 90 minutes more intentionally?

Nicolas Cole (19:03):

So I think that's an easy answer. I don't know if it's the most satisfying answer, but I think that focusing more on where are you in the process and are you actually doing it? If you're not doing it consistently, there's no point talking about anything else.

Daniel Scrivner (19:18):

Yeah, no, I think it's very well said. And I think that framework of stages makes sense. And it checks out in my own experience as well too.

Daniel Scrivner (19:25):

One of the things that I always try to uncover is tools. And for a lot of people it's just like, well, I just use the same average tools. But I wanted to ask you what tools you use? Because one, you're a prolific writer, you also do a lot of publishing obviously of books on Twitter, over email, a bunch of different mediums. Are there any tools that you really lean on or just tools that you really enjoy using?

Daniel Scrivner (19:49):

And that could be pieces of software, it could be a favorite notebook brand, it could be a pin, it could be anything. What comes to mind?

Nicolas Cole (19:56):

Once again, shameless plug for my own software tool, because templates are great.

Nicolas Cole (20:01):

To be honest, I'm really not a big tool person. I'm not a productivity app person or anything. I use the notes feature on my MacBook and on my phone, and I have a couple notes that are book ideas, article ideas, Twitter thread ideas, and I just dump stuff in there.

Nicolas Cole (20:18):

One tool, it took me a long time to find and I had been looking for it for years, and I noticed not too many other writers know about it, is there's a site called Reedsy, R-E-E-D-S-Y.com. And I think primarily it's a marketplace that matches writers with editors, and it's almost like a writer specific Upwork type situation. But they have a tool that's free there that is a text editor that you can export the text as Kindle files to upload to Amazon.

Nicolas Cole (20:54):

And that feature, which sounds really simple is not simple. And for years, what I would have to do is I would have to go find an editor, because I didn't want to learn how to do it myself. So I would go find an editor and I would pay them whatever their rate was to take the Word document and put it into the formatted file for Kindle.

Nicolas Cole (21:14):

And when I found Reedsy, I feel like I'm doing the video pitch right now, and when I found Reedsy everything changed. And I still use it every week now for Category Pirates, which is a paid newsletter I have with two other guys, the three of us authored snow leopard.

Nicolas Cole (21:29):

Every week we publish a mini book and I use Reedsy to convert the Word doc into a Kindle file and upload it to Amazon. That's how we're able to publish so many mini books. So there's the whole process if anyone's listening that wants to go use it.

Daniel Scrivner (21:43):

That's fascinating, and I imagine a lot of people might also be interested. If anyone listening is a writer, I think an Upwork for writer sounds super interesting. So I'm definitely going to go check out the site. I want to ask one more loaded question, don't hate me. And this one is about your philosophy of writing.

Daniel Scrivner (21:58):

One of the things you've clearly spent an enormous amount of time on, I assume you think of it as an infinite game, is just getting better at writing. Finding your voice, developing your voice, and continuing to push forward with that.

Daniel Scrivner (22:09):

So the question I want to ask is if someone pointed a gun to your head and said, "Distill down your thoughts about what makes good writing into just a few words or just a few sentences or just a few bullets," what comes to mind?

Daniel Scrivner (22:21):

And these can be just a couple of principles. This can be an acid test for good writing versus bad writing, how you think about your philosophy of good writing?

Nicolas Cole (22:30):

This is something that has taken me a really long time to understand, but again, once it flipped for me now there's no going back. Good writing changes the reader. And I think one of the most misunderstood parts of writing is, I remember when I was a kid and I wanted to grow up and be a writer, is thinking that it's about you. Thinking that being a great writer is the you show and it's all about how good you write.

Nicolas Cole (23:03):

And it's almost like the whole focus is just pointed back at yourself. And it takes you a really long time to realize that great writing has very little to do with you. It will change you in the process. It can be about you, yourself and your heart and your story and everything can be in it, but it is ultimately about the reader.

Nicolas Cole (23:23):

And so it's almost like you have to go through this process of retraining yourself to go, Okay, pretend for a second you're not writing. You walk up to some random person on the street and you ask them questions and you go, "What are you struggling with?" And then they have something that they're struggling with that you have an answer to, and you start explaining it to them.

Nicolas Cole (23:45):

It's not about you, it's about wanting to help that person. And so writing is just the mechanism for scaling that interaction. That's it. And even people that write memoirs about their own lives or people that write science fiction or mysteries or stories or whatever, ultimately the reason we love those stories is because they're archetypal of ourselves. We see ourselves in them.

Nicolas Cole (24:10):

And so yeah, my whole philosophy now is very, very over rotated on understanding the reader. If you don't know who you're writing for, then your writing is not for anyone. And if your writing's not for anyone, then it's a journal. And if it's a journal, then don't be frustrated when readers go, "I'm not paying attention to that because it's all about you." That's a hard pill to swallow.

Daniel Scrivner (24:33):

No, that's a really hard pill to swallow, I think especially for most people today. I want to ask two simple closing questions. The first one is, if you can share a tiny habit or practice that has had the biggest positive impact on your life or your work.

Nicolas Cole (24:47):

I'm going to give the most cliche answer ever here, but writing. And not just writing, but writing and hitting publish on the internet. My entire life changed, I was 23 years old living in a very small apartment with no air conditioning in Chicago. And I wanted to be a writer, had no idea how. And I challenged myself to write one Quora answer every single day for a year straight.

Nicolas Cole (25:13):

And publishing something, not just writing and hiding it away in my apartment, but publishing something accelerated my learning process. It allowed me to gather feedback from readers, which is the point that I was just making. It allowed me to see my work outside myself, which forced me to learn in a different way. It allowed people to get a sense of what I was writing earlier. I didn't have to reveal some big grand opus project.

Nicolas Cole (25:41):

So I can literally trace every single major milestone in my life over the past 10 years back to that decision.

Daniel Scrivner (25:50):

That's a great answer. It sounds like that the takeaway there is just committing to an active discipline in an area where you want to get better is extremely powerful. And just doing it, even if you have to stumble through it.

Nicolas Cole (26:02):

An active discipline, and I would even say an active discipline that you can do in public. There's something different about practicing in public. Small tangent, it's the same story of, I forget which Malcolm Gladwell book he put this in, but it's The Beatles story. Most people don't know that before they got signed, for 10 years they would play in clubs for seven hours a day.

Nicolas Cole (26:29):

And a lot of their songs they wrote as they were just riffing in these clubs, filling time. And so by the time they got their record deal they already had 10,000 hours of practice. But the reason that that practice is so valuable is because it was in front of other people giving you feedback. "Oh, you like this riff? Oh, you don't like this riff."

Nicolas Cole (26:50):

So I feel like it's the same with the gym, there's a totally different experience if you're exercising with or in front of other people versus completely by yourself at your house.

Nicolas Cole (26:58):

So yeah, daily discipline multiplied by in public is exponential result.

Daniel Scrivner (27:04):

Yeah, discipline plus feedback loop. So you can actually tell if you're making progress.

Nicolas Cole (27:09):


Daniel Scrivner (27:10):

You get that likely brutal feedback loop.

Nicolas Cole (27:13):

But it accelerates it, that's the point.

Daniel Scrivner (27:15):

No, no, no. It's extremely powerful. It's extremely powerful. It goes back to a principle that I always love and think about, which is just skin in the game. Making sure that, yeah, for those things, that you're putting yourself out there, because that's the only way you're going to learn and be able to get better.

Daniel Scrivner (27:27):

Last question, if you could go back to the start of your career, is there any advice, words of wisdom, reminders that you would whisper in your ear?

Nicolas Cole (27:37):

I'm starting to sound like an old person when I say this, but I just wish I would've known a lot of the things that I knew now back then. I wish I would've started earlier, even though I started as a teenager writing and all of these things.

Nicolas Cole (27:50):

But I wish I would've started earlier. I wish I would've not overthought it all so much. The number of times I would start, stop, restart. I was so obsessed with thinking I had to have it all figured out before I went on the journey, and now I've just completely let go of that.

Nicolas Cole (28:09):

I'm like, All right, I'm going to write this thing and whatever. Feedback loop, I'll put it out into the world and I'll see what happens, versus overthinking it for nine months and then...

Daniel Scrivner (28:18):

Well, or just keeping it in that notes app, and it's just something there that you stare at day after day after day after day.

Nicolas Cole (28:23):

Yeah, wasted a lot of time doing that.

Daniel Scrivner (28:26):

Well, this has been so much fun. Thank you so much for joining me, Nicholas Cole, this has been great.

Nicolas Cole (28:30):


Daniel Scrivner (28:31):

Thank you so much for listening. You can follow Nicholas Cole on Twitter at NicholasCole 77, and you can learn more about Ship 30 for 30, which is one of the largest cohort-based writing courses that kicks off every 30 days at startwritingonline.com.

Daniel Scrivner (28:46):

You can find a searchable transcript of this episode as well as our episode guide with ways to dive deeper into the books and ideas we covered at outlieracademy.com/139. That's outlieracademy.com/139.

Daniel Scrivner (28:59):

For more from Nicholas Cole, listen to episode 140 where we decode the art of category creation with Nicholas's latest book, snow leopard, how legendary writers create a category of one.

Daniel Scrivner (29:10):

You can find that episode at outlieracademy.com/140. That's outlieracademy.com/ 140. For more from Outlier Academy, follow us on Twitter, LinkedIn, Instagram and TikTok.

Daniel Scrivner (29:23):

Subscribe to our channel on YouTube or visit outlieracademy.com for more incredible 20 minute Playbook episodes. We'll see you right here with a brand new episode next Tuesday.

On Outlier Academy, Daniel Scrivner explores the tactics, routines, and habits of world-class performers working at the edge—in business, investing, entertainment, and more. In each episode, he decodes what they've mastered and what they've learned along the way. Start learning from the world’s best today. 

Explore all episodes of Outlier Academy, be the first to hear about new episodes, and subscribe on your favorite podcast platform.

Daniel Scrivner and Mighty Publishing LLC own the copyright in and to all content in and transcripts of the Outlier Academy podcast, with all rights reserved, including Daniel’s right of publicity.

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