Ryan Holiday’s Head of Content Isn’t Chasing Views

He's such a good storyteller and I feel something when I watch the videos. It's kind of a double-edged sword and this is the best piece of content advice I've ever gotten. Ryan Holiday is the New York Times best-selling author of an astounding 14 books. He has a newsletter with nearly a million readers and his YouTube channel just crossed two million subscribers days ago. Today I'm speaking with his head of content Blake Martin and this is a great conversation because in a world where we're all driven and measuring success with views, he's actually measuring success with something else. So Ryan Holiday is very famously analog and we live in a very digital world with AI and all these kinds of things. I'm curious how your team is actually using AI or if you're completely rejecting it altogether. Ryan has so many articles and emails and podcasts obviously in the social media content. He's produced so much content over the last 10-15 years. What I found when I want to make new content is that he's probably talked about something similar. So I use AI to help me go find what Ryan has talked about, buried in the blogs, everything like that. Get me to a concept, get me to some words on some paper and then I go and verify did he actually say this, how to make this into good content, but I use AI to help me get to the meat of what's there. Does he still use cue cards and everything? Like that's kind of the thing that I know him for. Is that still something he does? Yeah, 100% and there's actually a there's a video coming out. I don't know when this podcast will be released but it should be close to the time of his whole no card system and so 100% of Ryan still writes on no cards. It's the act of doing it that you're forcing your brain to remember, you're forcing your brain to put it down on the piece of paper and their whole no card organization system on how they organized by themes or chapters of books or whatever the project they're working on, they assemble their no cards to put in the project so it's all laid out for them. To you guys ever talk about offloading too much of your brain to AI because I feel like what you just described is a really intentional way and like a very clever way of remembering key information from hundreds of books or any kind of any kind of sources and then with AI you can do all of that in the blink of an eye but I feel like it's worse for your brain. Is that something that you and Ryan talk about? Yeah, he actually has a really good article about this that you know in the age of AI the most valuable skills are really good bullshit detector. We're not outsourcing critical thinking like AI should be the first step to get you to something but you can't just look at the AI and be like that's it and push it to a final product. So if you have scripts like there's been some times that a script has been presented that was literally just like you could tell it was copy and paste it from AI. AI can get you the information like never before and that helps the process but how do you weave a really good story together? What are the core pillars of good storytelling according to you and to Ryan Holiday's team? That's a really good question and I think it depends on what media you're talking about. For YouTube, yeah. Are you creating entertainment content? Are you creating information content? Are you creating a piece of content that is supposed to get people down to the funnel? That's not a thing too that Ryan talks about is like every piece of content has a purpose like everything that we do has a purpose and that purpose might not be just for views and I know that sounds crazy to like post a video or like we're not intending to like have a lot of views on this video but it could be either selling something so like a really good like sales pitch and if it converts one person at you know a thousand dollars like worth the video it's better than the cpm's on that video. The purpose could be showing Ryan up on stage like at an event and you know that video might get 20, 30,000 views but if one of those views is a CEO and wants to book Ryan for the next event then that video is very very valuable because that just brought in you know Ryan's speaking fee. In all these types of videos you have to think like value first like what is the viewer getting out of it and providing value before you ask something. You know let's say we sell course and video that would just talk about the course and all that it's not going to do very well right it's really going to get to the point that oh we have this course to sell but your attention is just going to bomb so it comes like how do we creatively provide value but then tell people hey if you want more or you want like a deeper diving to this we have this option but let's get back to the free stuff and the value of it then you're going to get two types of people one that weren't interested in it at all you know the masses the video goes to the people who aren't following you have no clue who you are they'll still get value out of it they're not going to be offended by just you know having that hard sell and then you're going to get the people that are genuinely curious that want to do deeper and again you're just a guide to help them get to the state that they want to get in and you're providing a path for them you have to talk about something so many times to get somebody to convert right and I think in the age of social media that was one of the biggest lessons working in this environment is seeing how many times we had to tell people that we were selling something or that something was coming out Ryan's book launch how many times and like you know every single day we posted about it on social media and my first thought was okay isn't this like annoying isn't this going to be like you know isn't this isn't dumb you know post it one time everybody's going to know about it but then like I would meet people in Austin that like new Ryan like right around the time of the book launch that new Ryan new Ryan's work and I'm like oh how do you pre-order the new book and they'd be like oh he's coming out with a new book and I'm like it's funny I've heard Alex Ramosey kind of say a similar thing where you have to tell people multiple times about your offer or about just anything that you're talking about and then Patty Galloway kind of talks about it as well where he says a lot of creators feel like they've done something and then they can no longer do it again and he's actually suggesting for people to lean into what's working and make it again and make it again and make it again and wait for the data to say okay your audience is actually fatigued by this it's just interesting like to hear it from you because it goes against with I think a lot of people think is the norm where it's like you talk about something and then you move on talk about something else yeah and even in the in the organic content like you said and this is the best piece of content device I've ever gotten is make something that you want to watch and keep doing it until you find another person who wants to watch it and then another person another person and there's so many business theory and content theory and lessons that stem from that one sentence of you know do the thing that nobody else can and be one of one of one or as Ramosey says like one of none and you know you're gonna win if you can do if you play your own game that nobody else can even compete in but it all trickles down to that simple articulate sentence of make content that you want to watch because then you're gonna be able to do it better than anybody in the world you're gonna be able to do it for longer than anybody in the world because you genuinely enjoyed doing it and I think like creator stumbled where they start off that way and they get to a certain level doing that but then they try to reach the moon or they get impatient and then start to sacrifice those values and start chasing views and chasing what might work and really lose what made them successful in the first place as head of content how do you know that you're doing a good job knowing the creator and knowing what they're trying to optimize for and taking this overarching brand of all these creators have a business behind them right so your job is head of content is also aligning with business objectives and being in communication with those teams if email subscribers are going down how do we use these social channels video acts written content how do we get people to the email list if that's the problem and that's like an objective of a head of content right how do we make the content that provides value to get people to that funnel if we have a course or we have a book or we have something like that how do we make content that directs people to that if we're in a phase we're honestly promoting anything how do we use this phase to grow the accounts and then the the metric is followers and views and all of that the way that I built my dogs instagram account my dog has about 200,000 followers and I got him that in about a year you're in a half and he has about a 20th of the views of a normal dog creator so I was very efficient in growing the account like didn't have like we didn't have millions and millions and millions of views but I grew the account very fast and the way that I did that is I optimized for conversions and that was the metric that I thought was the most valuable right because views people the views are just based on the algorithm right are people watching the video you know whatever platform you're on essentially boils down to that where if they're watching the video your video will get seen more but if people resonate with the video and they're getting value from it people speak with their money and business on social media people speak with the follow button are you providing value that they want to come back and see and build a relationship with you that's not determined on views that's determined on that follow button and so what I realized with my dogs account we were the first people on the internet to make ever make food for humans and dogs I had the first cooking show and there's a lot of creators that have done this now and have made similar stuff but we were the first people to like take a recipe and how it cook it give the give the viewer the full recipe from nuts to soup I just realized with these videos that for every 100,000 views I'd get a thousand followers it was a 1% conversion rate which was is insanely high on Instagram and so I kept thinking to myself like I made this video with my ex-girlfriend that got like 10 million views and from 10 million views that video got like 2,000 followers from it but from a cooking video that got 150,000 views I will get around that 2000 follow mark so I'm like why would I like keep making these like high levels, you say thin content that yeah, we'll reach a lot of people, but like does absolutely nothing for my brand or make these high value videos play with the packaging 'cause views I think are just based on packaging, right? You have your value that's conversions, views are packaging, how entertaining it is, how you're hook, all that kind of stuff. How do I play with that packaging to get more views on the videos? And then the conversion rate holds. So if I get more views on the video, I'm just gonna get more followers because it's a really good conversion right there. - Let's say you move on from Ryan. It's really easy to say, oh well I started with Ryan and he had this many subscribers and then we went to this many subscribers or I got him from an average view per video of half a million to however many. It's kind of a double-edged sword because you might not want to be measuring success with views. - When I first came on his Ryan's head of content, I was, I remember I was cooking and I was like thinking about content and I'm like Ryan owns this bookstore. That's one of the most unique bookstores in the country of not the world. Yet from the content side, there weren't really any like book recommendation videos. There wasn't content of like Ryan talking about books on his personal channel. So we started small. The first video was kind of a trend, self-help author rate, self-help books, honestly. - Yeah, yeah. - Yeah, we did that with Mark when I worked with Mark Manson. - Yeah, I think that was the inspiration there. So it was like, okay, so like that video did well with Mark. So like it's proven. So if for whatever reason this video doesn't work, it's an indication that our audience just doesn't resonate with it. Where it's not a question of like, is the video good, is the content good? This is a real like audience question when we're trying to like pivot the brand, right? So that variable was the one to test. And the video, it didn't get tens of millions of views. It got like 200,000 views. But if the views were the only thing we were looking at, we might not have done it. We might not have continued doing it. However, I noticed the engagement was really high. People loved it in the comments. They were asking to do more of it. And that conversion rate was back to the 1% of the cooking videos. And so from my experience, I knew this is something we need to double down on. So then it became a packaging game. We knew that the value was there. People liked to write in recommending books. Now, how do we package this concept of book reviews to get the videos to get a lot more views? 'Cause we know that the value is there. So it was like, you know, how would a video about best biographies do versus a video about books for athletes? And the difference is best biographies is a category of books versus like books for an identity. Testing that. How would a video do if a really well-known book was the first book in the video or an outlier obscure book was the first book in the video? 'Cause maybe people want a book recommendation that they haven't heard about. And that's why the obscure book would work. Or maybe people want the validation of this list is good because they've heard of the book and they'll watch the rest of the video. Testing all these variables, pulling these levers in the packaging. Then it hit away where the algorithm lined up, the timing lined up that was the beginning and the year people were interested in books. And then it was a game of how many of these can we crank out? How many of these can we come up with and just get up and get out there, sending up the system, having that competitive nature behind it. And again, views probably, I don't have the exact number. I would say probably around 20 million views across this whole book review series. Which is a grand scheme of things is not like massive. We're not talking billions of views. It's a lot of views in a short period of time. However, on Instagram in about four months, he got over 100,000 followers. The YouTube doubled from these book recommendations. So went from about 80,000 subs to now he's hit about 160. The best videos across the YouTube channel are these videos around these reading rules. And again, views not exceptional, not groundbreaking. However, the impact and the culture behind it, I met people at South by Southwest, a festival here in Austin, that I said I worked for Ryan Holiday and they said, oh, the guy that does book reviews, the guy that like recommends the books, I love that. They didn't know that he wrote about Stoicism. They didn't know he wasn't an author. This now has reached a completely new audience and a new world. People are coming into the bookstore, saying I saw this on social media. They're going to the bookstore to buy books from. And just yesterday was Ryan's second time on the morning Joe where now he has a recurring episode on mainstream news, which he's never had before in his career, recommending books because the anchor saw him on social media and now is moving to TV. And that's a huge win and something I'm super proud of. That's another way to look at it and say like, this content, this format got to this point to the news. - That's super cool. I think one thing that I've learned from this conversation has been like the criteria for YouTube content is always like, oh, packaging first and then have the idea, figure out the title thumbnail, write the scripts. I think also what should be included is like, what is the goal of this video? And I think that's something that you put at the top of the Google Doc and it's like, the goal is new views. And so we're measuring success by reaching a million views. Or the goal is get Ryan on TV six months later because we've got this master plan to make him this excellent book reviewer on social media to the point where more and Joe reaches out. How did you get connected with Ryan, by the way? - I had followed the Daily Stoic for, let's say, four or five years at this point. The way that I first heard about Ryan was my mom got me his book set and I loved those books. I read "Meditations by Marcus Aurelius." So I'd been following the Daily Stoic and Ryan for a little bit of time. And I had not checked their account in like six to eight months. Like it was a long time and I don't know what came over me to just check their stories that day. And they had just posted, we're looking for a social media coordinator, a part-time social media coordinator in Austin. Send us like email us your resume and we'll see. So I jump on it. I open up my new tab, I write this email. And I'm thinking about it. And I'm like, yeah, I like got my dog like 200k, but like that's 200k versus like three million on this. Like I think there's like 15 million subs, followers, newsletter across all the platforms, right? So I'm like, there's there's a whole way. And so I send this email to a woman, I'm like, yeah, I'm in Austin, I'm you know, I'm there. And I was, I remember driving up, I was in Tucson at the time, the next day I was driving up to Phoenix. And I get an email back from his head of content at the time, Chelsea. And she said something along the lines, "Hey, we're really interested in your resume. Would love to set up a phone call." And I remember probably shouldn't be checking your phone while you're driving, but I remember seeing that notification. And just screaming up like, "What's up?" This is awesome. I was so nervous. And then I like, next week I have a phone call with Chelsea. And then I got to the in-person interview with Ryan's business partner, waited to hear back. They said they get back to me in like a couple weeks then it turned out to be like the next day. And they're like, we'd love to make you an offer. And then I started off part time as a social media coordinator for a few months and then was promoted to the head of content. - Yeah, so many stories in this industry are just from serendipitous things happening, checking someone's story on Instagram. And it's only there for 24 hours. And it got, you timed it perfectly to find it. It is fun to hear stories like that. 'Cause 100% pretty common thing. - I think like the advice I would give to anybody like coming into the industry or wanting to work with one of these big creators to work with a big platform. Ryan talks about his hiring policy and this is the way that I ran the internship that we had hired on is a very simple question. Have you done the thing before? And what I mean by that is like social media is very unique industry that there's no barriers to entry. You have a phone, you can download the apps and you can start posting. The thing is is like you don't have to like have like millions of followers, probably if you have millions of followers you're not gonna be going in, of trying to work for somebody else. But the point is is like learn the skills, do the thing consistently show improvement. And again, don't just be posting stuff like without improving. Get 1% better every single video. Show that you have the ability to analyze something, learn from it, iterate and improve. Then you can take that and it's a lot easier sell of, hey, I've done this. This is what I've learned doing this. I know I'm not as sensual as you know, I don't have as many followers or whatever, but these are the skills that I've made. I'm confident that I have the skills to get me started and the ability to learn and catch up quickly and I can make a difference in your business. And I think that that like, it's so hard to find talent that has two essential qualities. One, the ability to learn and then execute on that learning and two, the working hard. One of my good friends, his name is David Iraq, he was Gary V's creative director for many years. He was talking about, I'm gonna paraphrase it, but he was talking about when he first worked for Gary, he met Gary on the street. I was like, Gary, please, like, give me a shot. Like, I'll make a video for you and he sent that video. A lot of people hear this advice and they email the creators and they're like, hey, can I make this for you? If I make this for you, will I get a job? It's like, no, no, no. You just make it and send it. Like, you're in position coming to them. So he did that, Gary and my shot. This guy, I was living in a basement, going into the office, like filming, editing, uploading stuff till we hours in the morning, 1, 2, 3 a.m. And then he was the first one in the office at 7 a.m. and did this for many years, right? And the ability to work your butt off and to get better, you're gonna make mistakes, you're gonna mess up, you're gonna have moments that like it's like, oh, I shouldn't know better, like I'm learning. That's acceptable as long as you are learning from it and you're trying really hard. When you're continuously making the small mistakes or something like that, it's really hard to justify to your boss that you are working hard, that you have a capacity to have the responsibility that you do working in one of these really big brands. - Yeah, higher for attitude, not aptitude. If you have the right frame of mind, if you're willing to do the work, you're already at a 99% of people, so. - Well, 100% will come, just get it done. - And you have like a body of work to at least show your attempting to get that skill set. - Right. - Where it's like, I made this dog account. I have to start a pool table, I have nothing to do with philosophy, but like, I'm trying here. - Yeah. - And yeah, effort goes a long way. All right, my last question for you is the same question I asked everybody and that is, who is a smaller creator that's on your radar right now? - This guy that I really like right now, his name is Zerkey on Instagram. He makes the most simple, but emotional, cord striking videos I've seen on the internet. And he can see it's one take, it's not editing, he puts captions over it, he uses an old, there's a style to it. And he just talks about a situation in his life and like the lessons learned from it. And he's a great storyteller. You know a video that's coming from him, the second you see it in the algorithm, because every video is like pretty much the same him holding the camera, talking straight to it. It's kind of that like, yap style, but it's one step beyond the yap style. Like I said, there's no cuts. And I think that ability to make people feel something, that's the most valuable skill you can have. And it's very, very hard. I keep going back and forth, is this something that you can learn or maybe just, you know, things that people have and others don't, but this guy is so good. I love his videos. - Well, you're very well spoken and you've made me think a little bit differently, which is what the goal of these podcasts always are. So thank you for coming on the show, congrats on the success you've had with Ryan and hopefully looking forward to connecting with you in the future. - Thank you, appreciate you, Don. - That's it for this episode. Thank you so much for watching and listening. If you're new here, please consider subscribing or leaving us a review on the audio channels. It really, really helps us out in the early days of this show. Share it with a friend. Share it with someone who you think might be a good guest. We're looking to profile producers, creative directors, heads of content, people who work for YouTube channels that have over a million subscribers. If that's you, please consider reaching out as well. I would love to speak with you. We'll see you in another episode. Take care.