In this YouTube segment, Matt Ragland explains why Ryan Holiday occupies the final spot on his personal "creator Mount Rushmore." Ragland admires Holiday not only for his impact on his own creator mindset—particularly around content strategy, business structure, and flywheel thinking—but also because Holiday’s lifestyle (husband, father, small‑business owner) feels attainable to him. Ragland walks through Holiday’s body of work, from early titles like Growth Hacker Marketing and Trust Me, I’m Lying to his later Stoicism books (The Obstacle Is the Way, Ego Is the Enemy, Stillness Is the Key). He highlights Holiday’s sophisticated content‑repurposing system: daily emails (Daily Stoic, Daily Dad) feed a daily podcast, weekly long‑form interviews, YouTube videos, and short‑form clips, with each piece cross‑feeding the others. Ragland details the monetization model—sponsorships on the 800k‑plus‑subscriber email list, a $20/month (or $240/year) membership that removes ads and bundles several $150 courses, and a physical bookstore/studio called The Painted Porch in Bastrop, Texas, which also serves as the production hub and a direct‑sales channel for recommended books. He notes Holiday’s integration of family life, noting that Holiday’s two kids engage with his content, and mentions Holiday’s note‑taking system as an additional source of inspiration. The overall message is that Holiday’s interconnected, values‑aligned business and personal life exemplify a creator model Ragland aspires to emulate.
Chapters
The fourth and final person on my Mount Rushmore creator list is Ryan Holiday. Ryan is an author. He is also a podcaster, a YouTuber, a speaker, and he is a husband and father. That's something I'll talk about. He's also a small business owner. And I'll talk about this a little bit more. But the reason that— one of the reasons that Ryan comes to mind for me is not only like the impact he's had on my creator life and how I think about content and business structure and team and flywheels in, in a sense, is that he's also doing it in a way that I could see myself like living the kind of life that he does. And not everyone that I've like mentioned on this list, I wouldn't want to have like Tim Ferriss's life. He— I'm very inspired by him, but I wouldn't want to have Tim's life. I wouldn't necessarily want to have than Seth's life. And part of that is because Seth is older, older than me. But I look up to and I admire Ryan because of the way that he creates content, the way that he built his business, and because of the person that he is outside of those two things. But the reason that I love Ryan's work is because I've been reading his books for a long time, whether it's Obstacle Is the Way or Stillness is the Key or Ego is the Enemy. The other, the other thing, the first very, the very first book that I read of Ryan's, I actually saw it when I was scrolling through my Kindle the other day, is Growth Hacker Marketing. And that was when he was like before he was doing the Stoicism writing and he was working at American Apparel. Another book that I read of his really early on was Trust Me, I'm Lying was, was another one about like media manipulation. And that's another one, like I mentioned Tribes and Seth Godin, Trust Me, I'm Lying, written 10, 15 years ago, written a while ago. And it is insane how like applicable that is to our modern media landscape. That's not a thing that we're going to go into right now, but He has just, he's done so much. And like specifically what I like about seeing how he's built his business and like develops his content right now is he's like the king of like how to repurpose content in like a healthy way that doesn't seem like you're just using the same thing over and over again, but it's still like all almost every piece of content that he makes is used at least as a piece in something else. And so like when he writes, he writes 2 daily emails, there's Daily Stoic and Daily Dad. And he also is on YouTube 2 or 3, 2 or 3 times a week. He has a daily podcast, his daily. But here's like where some of the overlap happens. The Daily Stoic podcast is literally him reading the Daily Stoic email. And so that, like, repurposing is one-to-one. But then on Saturdays, he has a long-form Daily Stoic interview. But then that content, that interview becomes sections of future emails, and parts of that are pulled out to become clips on short-form clips on social media. He will also do the same thing with his longer form YouTube videos. And those become like, maybe not direct word for word emails, but those become inspiration for other emails. And also like back the other way, if he writes an email and gets a lot of great replies on, he's like, hey, I'm going to do a video about this now. The other thing that I don't know if a lot of people realize is just about like his business that I think is really cool is One of the main ways that he monetizes his email list is through sponsorships, because like Daily Stoic, I think, has over 800,000 subscribers now. So obviously, if you are going to sponsor the Daily Stoic email, you're going to be paying for it. But there's also a membership community called Daily Stoic Life, and Daily Stoic Life is basically $20 a month, $250, $240 for the year. And so if you're a member of Daily Stoic Life, you don't see any of the advertising on the emails. But wait, there's more. If you're a part of Daily Stoic Life, the membership, Ryan also has like these, these courses like around stoicism and reading and like habits. He has like 3 or 4 really great courses that sell for $150 each. And if you're a part of the membership, then you get all those courses. So you get a membership, you get all the courses in the membership, you don't see any sponsorships, just the way that he puts it all together. And then my favorite little part of this, and I don't know how much money he actually makes on this, it just, it inspires me to think about like how interconnected all these things are, is he owns a bookshop in Bastrop, Texas. And I hope I'm pronouncing that, that town properly. Called The Painted Porch, and it's like really awesome bookstore. It also doubles as his office. He records all of his podcasts and YouTube videos in there. So it's also his studio. But he recommends a lot of books in his emails. He actually even has another email list, a once-a-month email that goes out. It's like, hey, here are all the books that I read this month. Voracious reader. Like, I don't know how he reads the amount that he reads. But when he sends like, you know, here are the 5 to 7 books I read this month, and then like end of the year, here are my favorite books of the year. Every, almost every single book that he mentions is linked to purchase at The Painted Porch. So he's not linking to Amazon, he's linking to his bookstore, to his own inventory that he is selling from. And he talks about this a lot, uh, or he talks about this a little bit when he was, uh, one of the episodes he was on My First Million. But I just like the way that he has built his life and his business to be so interconnected and overlapping is like really, is really inspiring and interesting to me. I think he's the other reason, like Ryan and I are a similar age. He has two kids that he like reading, reading his emails and interacting with him just a little bit. Very, very in tune with their lives. And so like him being a parent, him being a husband and doing the kind of things that he's doing is also really, really inspiring to me. I haven't even talked about his note-taking system, which is also very inspiring to me as like a note-taking nerd. But to round out my Mount Rushmore, I would definitely put Ryan Holiday up there for me.
Yeah, he feels like the culmination for you of like all of the different things you've learned and things that interest you with, with business and being a creator. He feels like for you, like you found the person who like encapsulates all of that. I think, I think it's really cool.
