BONUS | Ryan Holiday Responds to Daniel Radcliffe

Summary

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The Daily Stoic – BONUS | Ryan Holiday Responds to Daniel Radcliffe

Podcast Host: Ryan Holiday
Episode Date: May 12, 2026
Key Guest Mentioned: Daniel Radcliffe

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Episode Overview

In this special bonus episode, Ryan Holiday responds to Daniel Radcliffe’s strong recommendation of a book exploring American colonialism and imperial history. Using Radcliffe's endorsement as a springboard, Holiday elaborates on the importance of understanding America’s past imperial endeavors—not just for the sake of history, but to gain essential perspective on current global politics, American identity, and the ongoing consequences of empire. The episode serves as both a passionate book recommendation and a contemplative discourse on history, morality, and the lessons still unlearned by American society and leadership.

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Key Discussion Points & Insights

1. Daniel Radcliffe's Book Recommendation (03:25–03:44)

• Ryan Holiday introduces Daniel Radcliffe’s (widely known as Harry Potter) recent enthusiastic praise for a book about American imperialism and colonial history.
• Holiday echoes Radcliffe’s endorsement:
  • Quote [03:25]: “Daniel Radcliffe, Harry Potter’s been raving about this book. I just want to co-sign on this recommendation because it is an incredible book that not only changed how I understood America, but it changed how I understood the world.” — Ryan Holiday

2. The Importance of Understanding Historical Context (03:45–05:05)

• Holiday stresses that to truly grasp present-day events and attitudes, one must understand the intricacies of the past, especially America’s lesser-discussed imperial actions.

• Guano Islands and Colonial Competition: He gives a vivid historical anecdote about 19th-century powers fighting over guano-rich islands for gunpowder production, highlighting how bizarre and influential such episodes were.

• Pearl Harbor & the Philippines:

  • Quote [04:28]: “When America is attacked at Pearl Harbor, Roosevelt gives this famous speech, he says, you know, this was an act of war. Japan attacked America in Hawaii and also attacked the Philippines. Except for from Japan’s perspective, the Philippines were also America.” — Ryan Holiday

3. America’s Colonial Past and Its Dissenters (05:10–06:09)

• Holiday notes that not all prominent Americans supported imperial expansion; figures like Andrew Carnegie and Mark Twain were fervently opposed to annexing places like the Philippines.
• Memorable Reflection [05:52]: “Although this book shows some of the horrible things that America did as a colonial power, it also makes it clear that not all Americans were on board with this…” — Ryan Holiday

4. The Lessons (and Failures) of Empire and War (06:10–07:40)

• One of the key lessons from WWI and WWII was that outright control and colonization are “a stupid strategy,” detrimental morally and strategically.

• Holiday insists this lesson is still frequently forgotten, citing America’s failures in Vietnam as a tragic echo of past mistakes.

• Quote [07:17]: “What a moral quagmire it would put us in. Replacing one colonial power by becoming one ourselves.” — Ryan Holiday

5. The Puerto Rico Chapter—A Haunting Reality (07:45–08:25)

• Holiday and Radcliffe specifically mention the disturbing treatment of Puerto Ricans as a crucial, unsettling chapter in the book—highlighting forced medical experiments and broader themes of dehumanization.
• Quote [07:58]: “There’s all these terrible medical experiments that we did on Puerto Ricans, as if they were not only not Americans, but somehow not human beings.” — Ryan Holiday

6. Memorable Moments and Reflections from the Book (08:26–09:55)

• Drawing inspiration from his own reading habits, Holiday describes marking up the book and being unable to forget its many powerful passages.
• The contrasting attitudes of Rudyard Kipling and Mark Twain towards empire are discussed, with Twain’s deeply moral opposition emphasized:
  • Historical Quote [09:18]: “We abolished them utterly, Mark Twain said, leaving not even a baby alive to cry for his mother… What we did in the Philippines was horrendous. Those critics were absolutely right to warn about how badly it was going to go.” — Ryan Holiday (quoting Twain)

7. America’s Modern Global Position (09:56–10:35)

• Holiday points to the long-term consequences of colonial and wartime policies, such as the establishment of US military bases worldwide. He disputes modern “America first” arguments by highlighting how these bases actually serve American interests more than host nations’.
  • Quote [10:10]: “What you understand reading this book is we’re the ones getting the free ride. We have the great deal. No other country has stuff like that.” — Ryan Holiday

8. Tangential Book Recommendations & Stoic Reflections (10:36–11:13)

• Holiday links the book to other key works:

  • War Is a Racket by Smedley Butler: Butler, a highly decorated Marine, fought in many of these wars and became a vocal critic of US militarism.
  • Gangsters of Capitalism: A biography on Smedley Butler.
  • Civil Disobedience by Henry David Thoreau: Contextualizes Thoreau’s protest against the Mexican–American War and the expansion of American slavery.

• Notable Reflection [11:00]: “To me, the powerful sign about how good a book is is whether it stays with you.” — Ryan Holiday

9. The Urgent Relevance for Today’s Leaders (11:14–11:21)

• Holiday wraps up with a pointed Stoic lesson: If American leaders read and understood these histories, perhaps current mistakes—especially those based on ignorance of the imperial past—could be avoided.

• Final Quote [11:17]: “If more of our leaders in Washington read this book, maybe we wouldn’t be making some of the fatal mistakes that we are making right now.” — Ryan Holiday

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Notable Quotes and Moments

• On book impact:
  “Not only changed how I understood America, but it changed how I understood the world.” (03:25, Ryan Holiday)

• On colonial atrocities:
  “We abolished them utterly, Mark Twain said, leaving not even a baby alive to cry for his mother.” (09:18, quoting Mark Twain)

• On Puerto Rico’s painful history:
  “There’s all these terrible medical experiments that we did on Puerto Ricans… as if they were not only not Americans, but somehow not human beings.” (07:58, Ryan Holiday)

• On American empire and military bases:
  “What you understand reading this book is we’re the ones getting the free ride.” (10:10, Ryan Holiday)

• On lasting value:
  “The powerful sign about how good a book is is whether it stays with you.” (11:00, Ryan Holiday)

• On lessons for leaders:
  “If more of our leaders in Washington read this book, maybe we wouldn’t be making some of the fatal mistakes that we are making right now.” (11:17, Ryan Holiday)

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Thematic Timestamps

• 03:25 — Daniel Radcliffe’s endorsement and book overview
• 04:28 — Pearl Harbor, the Philippines, and American imperialism
• 05:52 — Dissenters within America’s imperial history
• 07:17 — Vietnam, failures to learn from history
• 07:45 — Puerto Rico’s tragic experiences under US rule
• 09:18 — Mark Twain’s condemnation of American conduct in the Philippines
• 10:10 — The real beneficiaries of America’s global military bases
• 10:36 — Additional book recommendations and Stoic insight
• 11:17 — Final reflection on history’s urgent relevance

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Summary

Ryan Holiday, inspired by Daniel Radcliffe’s public praise of a book on American imperialism, unpacks the book’s lessons and their significance to both American identity and contemporary politics. He uses vivid historical anecdotes, moral reflections, and references to related readings to argue that the United States’ imperial and colonial actions remain underappreciated drivers of present-day attitudes, policies, and global conflicts. Holiday’s tone is reflective yet urgent, urging listeners—particularly leaders—to understand these histories to prevent repeating their mistakes.

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For deeper learning and historical context, consider reading the works discussed or visit DailyStoic.com.

Transcript

[Ryan Holiday]

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[Ryan Holiday]

welcome to the

[Stephen Hanselman]

Daily Stoic podcast designed to help bring those four key Stoic virtues, courage, discipline, justice and wisdom into the real world.

[Guest Speaker]

Hearing anybody complain about Bad Bunny, like not being American or any of that stuff, like now having, I mean hearing them complain about it anyways is heinous. But like after having read that book, you're like, no, you guys need to shut up, get very defensive.

[Ryan Holiday]

I also love the Puerto Rico chapters. It really informed re watching the super bowl and I was just like, did you watch that?

[Guest Speaker]

I sounds like a brag. I can't help it. I was there. I I picked the right year to do a sports based comedy with NBC because they also had the super bowl. So they sent me that and I got to go and it was awesome.

[Ryan Holiday]

So Daniel Radcliffe, Harry Potter's been raving about this book. I just want to co sign on this recommendation because it is an incredible book that not only changed how I understood America, but it changed how I understood the world. The way to understand the present moment is almost always by better understanding the past. For instance, did you know that in the 1800s there was a race to take up islands in the Pacific and all over the oceans and that were covered in bird shit? Because that bird shit guano was a critical ingredient in making gunpowder. So many of the wars in the 19th and the early 20th century were a product of colonial wars. Before that, these empires were fighting over these obscure islands that weren't even inhabited because they wanted to own the bird shit that they could use to make weapons to fight over other more valuable pieces of land. One of the most interesting things I took from this book is at the beginning, he's talking about how when America is attacked at Pearl Harbor, Roosevelt gives this famous speech. He says, you know, this was an act of war. Japan attacked America in Hawaii and also attacked the Philippines. Except for from Japan's perspective, the Philippines were also America. It was just attacking America in two places. The American flag was still flying over the Philippines. We'd given it back to the Filipinos, but we were still ruling it for like a 10 year interim period before we handed it off. Douglas MacArthur grew up in the Philippines, he was almost more Filipino than he was American. And I think it's worth saying, though, although this book shows some of the horrible things that America did as a colonial power, it also makes it clear that not all Americans were on board with this and that other Americans, Andrew Carnegie, Mark Twain, some luminaries of the time, were adamantly opposed to, say, annexing the Philippines. Right. America is saber rattling, threatening its neighbors, about overtaking Greenland. This feels like a throwback to the 1700s and the 1800s and the early 1900s, and indeed it is. And so to better understand that, you should understand that period, and you should also understand the lessons that were learned from that period, from the. The mistakes and the injustices and the wars and the disasters that came from it. One of the most powerful things that America learns coming out of World War I and World War II, two wars that were essentially about colonialism, is that actually owning the territory, controlling the land, subjugating the people, is a stupid strategy. It's not effective. It's not efficient. It opens you up to not just undermining your values, but. But it makes enemies of people. We famously didn't learn this lesson so well. Vietnam wouldn't have happened had we fully understood it. We end up backing the French as they attempt to regain possession of Vietnam after the Second World War. And then we replace them. And we told ourselves we were fighting communism, really, we were fighting to preserve the remnants of colonialism. But this is just an amazing book. I think the title is funny. It gives you a peek into how. What a great job the author does at making a seemingly dry or academic subject really, really interesting. And look, how desperately do more people need to know and read about this book. People claiming that Bad Bunny is not an American. They need to have a better sense of America as an empire. And Daniel rightly highlights the Puerto Rico chapter, which is particularly haunting. There's all these terrible medical experiments that we did on Puerto Ricans, as if they were not only not Americans, but somehow not human beings. I just actually had someone grab my copy off the shelf. Let me see some of the stuff I liked in here. I always mark the pages of books that I read, and I marked a bunch of them. But to me, the powerful sign about how good a book is is whether it stays with you. Oh, yeah, there's a great chapter in here talking about the difference. Kipling and Twain are both friends, but he points out how they had a very different view of colonialism. And so he obviously talks about the white man's burden which is interesting. Something that Twain sort of disputed long before the. Some of the famous photos coming out of Vietnam. The one with the gun, his head, the napalm photo. There's this famous photo in 1906, a trench filled with bodies in Badajo. We abolished them utterly, Mark Twain said, leaving not even a baby alive to cry for his mother. And then Pershing said, famously, I would not have that event on my conscience for the fame of Napoleon. And what we did in the Philippines was horrendous. Those critics were absolutely right to warn about how badly it was going to go. What a moral quagmire it would put us in. Replacing one colonial power by becoming one ourselves. There's a great chapter in this book in Lend Lease for people now who are sort of like America first, isolationist, not understanding that what America did by coming to Britain's rescue In World War II, the, the lend Lease act, and then what we ended up getting to were rights to bases all over the world. Priceless real estate that allows America to project its power in the world by, but only controlling small bits of territory, not the whole country, not needing to subjugate people, letting there be free determination. And that the act of rebuilding Germany, the act of rebuilding Japan, this wasn't simply an act of charity. This wasn't altruism. The bases that America has there allows it to be a superpower, and then the ongoing maintenance of that relationship. Trump sometimes complains that these countries are getting a free ride. What you understand reading this book is we're the ones getting the free ride. We have the great deal. No other country has stuff like that. And certainly to set up those relationships now would cost far more than whatever the terms were in the 1940s and 1950s. And with Puerto Rico, how many people know that President Truman was almost assassinated by Puerto Rican nationalists? There was a shooting in, I think, like in Congress about it. Oh, and it's so funny. I. I always define a good book by whether I get another book out of it. It wasn't till towards the end of this book that I read this little passage about Hoover loving to fish. It says Hoover's love of fishing, an activity he revered for the quieting of hate, hushing to ambition and a promotion of meekness. I ended up finding a book that Herbert wrote about fishing, which was this lovely, sweet, sort of soul nourishing book. Just to make this a good video, I'll connect you to two other books that I absolutely think you should read. There's this book, War is a racket by General Smedley Butler, the most decorated Marine in U.S. history. He fought in those colonial wars and he came to understand what they really were and what they were really about, and he spoke out about it. And there's another book about him, a biography about him that pairs well with this called Gangsters of Capitalism that I would recommend. But definitely read this book. Henry David Thoreau's Civil disobedience is included in this one. People forget that Thoreau going to jail and civil disobedience, what was that about? That was in resistance to the Mexican American War, which Thoreau rightly understood was part of the expansionist slave powers trying to turn America into a slave empire. They had designs not just on Mexico, but Puerto Rico, the Dominican Republic, Cuba, all of Canada. They wanted to expand and expand slavery, and they saw America as a future slave empire. Thankfully, that didn't happen. So anyways, couldn't recommend this book highly enough. You should absolutely read it helps you understand what's happening in the world. And if more of our leaders in Washington read this book, maybe we wouldn't be making some of the fatal mistakes that we are making right now.

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