A Note from James: We kept recording because the conversation wasn’t done. Part 1 was about writing and honesty. Part 2? It’s about consequences—what happens when people believe their own hype, when we confuse being loud with being right, and when storytelling gets weaponized. Ryan Holiday has written about ego, stillness, and obstacles. But this part of the conversation gets at something deeper: what happens when power and narrative collide. And how do we live with integrity when the tools we u...
Jul 30, 2025•40 min•Ep. 1343
A Note from James: Ryan Holiday is one of the few writers I consider a peer—not just because of the work he’s done, but because of the choices he's made along the way. We’ve both published a lot of books. We've both dealt with audiences, platforms, and the weight of having a “point of view” in a world that increasingly wants you to pick a side. This episode wasn’t meant to be a debate or an interview. It was just two people trying to make sense of the tension between creativity and truth, honest...
Jul 26, 2025•40 min•Ep. 1342
A Note from James: When I first said that college was a scam, people thought I was joking—or worse. But I wasn’t. If you’re 18 and listening to this, don’t go to college. And if you’re a parent, don’t send your kid without doing the math. College doesn’t guarantee a better life anymore. In fact, it could cost you years of freedom, tens of thousands of dollars, and saddle you with debt you can’t escape. In this episode, Doug Hill and I talk about why the traditional path of “get a degree, get a j...
Jul 23, 2025•25 min•Ep. 1341
A Note from James: Owning a home has been sold to us as the American dream. But what if it's actually a financial nightmare? In this episode, I talk with my friend Doug Hill about why I think buying a house is a bad idea—not just a little bad, but one of the worst investments you can make. Doug and I disagree on some points, and that's the fun part. This isn't about being contrarian for the sake of it. It's about questioning assumptions that most people never even stop to think about. Episode De...
Jul 18, 2025•25 min•Ep. 1340
A Note from James: So Chef Curtis Duffy—he’s won Michelin Stars, a James Beard Award. He’s been on Netflix’s Iron Chef , was a judge on Top Chef season 21, and he’s even shown up in The Bear . He runs the Chicago restaurants Ever and Grace, and he wrote this incredible memoir called Fireproof: Memoir of a Chef . I could list all the accolades, but what really got me was his story—it's one of the most intense and heartbreaking I’ve ever read. The kind of story that stops you in your tracks. We ta...
Jul 11, 2025•58 min•Ep. 1339
A Note from James: Miesha Tate—at first, I’ve got to admit, I didn’t know much about UFC or MMA. But Miesha was the World Bantamweight Champion, and she fought Ronda Rousey—probably the most famous female fighter in the sport. I watched one of their fights, and honestly, I don’t know how I’d survive even a quarter of a second. But the conversation we had wasn’t what I expected. Miesha opened up about the mindset behind championship success, the weight of public expectations, and how depression c...
Jul 08, 2025•1 hr 13 min•Ep. 1338
A Note from James: One of the funniest guys I’ve ever spoken to—Dave Barry. I always love talking to him. He’s been America’s top humorist since the early ’80s with a syndicated column in 500 newspapers and a long list of bestselling books. This is his third time on the podcast, and his latest book, Class Clown: Memoirs of a Professional Wiseass , is out now. We get into everything—his process, his adventures, and his signature style of humor that’s made him a legend. It’s always fun with Dave. ...
Jul 01, 2025•49 min•Ep. 1337
Notes from James: I had no idea this conversation would go where it did. I thought we’d talk chess. Instead, we talked about life, trauma, manipulation, redemption… and how one of the world’s most popular games can be both a tormentor and a savior. Episode Description: In this raw and powerful episode, I sat down with Danny Rensch—International Master, Chief Chess Officer of Chess.com, and author of the upcoming memoir Dark Squares —to uncover a story that’s anything but a typical chess tale. Ra...
Jun 28, 2025•28 min•Ep. 1336
A Note from James: Man, what a fascinating career Robert Rosenkranz has had—multi-billionaire, involved in virtually every part of finance and American industry. He wrote a book called The Stoic Capitalist , and what really stands out is how he's actively applied stoic principles to achieve immense success throughout his career. Even from a young age, stoicism played a crucial role, guiding him through critical business decisions. It's a real pleasure speaking with Robert—an American icon. Episo...
Jun 25, 2025•1 hr 3 min•Ep. 1335
Notes from James: When I turned 40, I was depressed. I checked the top 50 chess players and saw only one person around my age: Viswanathan Anand. That moment gave me hope. Episode Description: I met one of my lifelong heroes—five-time World Chess Champion Viswanathan Anand—and got to sit down with him at the Norway Summit to unpack what it really takes to stay at the top… for four decades. We didn’t just talk about chess—we talked about life, legacy, improvement, and how to overcome self-doubt a...
Jun 22, 2025•24 min•Ep. 1334
A Note from James: So I’ve been doing this podcast for a long time—over 1500 episodes—and I’ve spoken to everyone from billionaires to best-selling authors, athletes to entrepreneurs. But there are a handful of episodes that still ring in my ears years later. One of them was Episode 156 with Gary Vaynerchuk. I was just re-listening to it while pulling together notes for a potential book, and I realized this conversation is timeless. It’s not about hype. It’s about freedom. Gary’s blueprint—learn...
Jun 19, 2025•1 hr 1 min•Ep. 1333
A Note from James: So the question is, I really feel that in order to get not good at something, but great at something, you have to be obsessed. You can't just wake up and decide to be obsessed—it has to be deep, almost irrational. Obsession is like addiction. It throws your life off balance, and yet... there’s this insane joy when you enter the subculture of your obsession and get better at it. I’ve seen this recently in crypto. I saw it in chess in Norway, commenting on what might’ve been the...
Jun 15, 2025•1 hr 2 min•Ep. 1332
A Note from James: Michael Dell. Founder of Dell. I remember in college, hearing about this kid who was building computers in his dorm and making millions. I thought it was a myth. It wasn’t. He’s the real thing—and he just kept going. I wanted to understand what drove him, what it felt like to deal with Carl Icahn trying to wrestle his company from him, and what success feels like after decades of being in the game. Also: I had to ask why Dell didn’t invent Google. That, plus how he’s now think...
Jun 12, 2025•53 min•Ep. 1331
Notes from James: Most people get stuck at the idea stage. That’s why I’m sharing frameworks—so you’re not staring at a blank screen. These techniques have helped hundreds of people (including me) go from idea to published book in just 30 days. Episode Descriptions: In Part 5 of my 30-day writing series, I unveil four of the most powerful book-writing frameworks I’ve ever used or taught—and they’ve helped hundreds of people write their first book in just a month. These aren’t theoretical. They’r...
Jun 05, 2025•34 min•Ep. 1330
Episode Description: James reconnects with entrepreneurs Michael and Kass Lazerow, whose journey spans selling Golf.com for $24 million, launching and pivoting Buddy Media into a $700 million Salesforce acquisition, and now investing in breakout brands like Liquid Death. This episode isn’t about startup clichés—it’s about emotional resilience, firing with kindness, how marriage can (barely) survive co-founding, and how to spot a trend before the world does. They break down their “Go Gauge,” the ...
Jun 03, 2025•1 hr 3 min•Ep. 1329
Notes from James: Let’s be honest: most people who write a book never make money from it. Why? Because they stop at the last page. I want you to go further. In this episode, I show you how I turned my books into speaking gigs, consulting work, investment deals, and more. You don’t need a big publisher or a massive budget—just the right strategy. Episode Descriptions: In Part 4 of my 30-day writing series, I tackle one of the biggest questions aspiring authors face: Should you self-publish or go ...
May 30, 2025•35 min•Ep. 1328
A Note from James: Well, you can't get more information about tariffs and the economy than what I just got and you're about to listen to. Wilbur Ross, who was Secretary of Commerce under the first administration of Trump, just came on the podcast. I got to ask any question I wanted—about tariffs, the economy, everything. Don't forget, in Trump’s first administration, we saw steel and aluminum tariffs, and there were all the same concerns—about the economy, inflation, political blowback. Wilbur R...
May 28, 2025•47 min•Ep. 1327
A Note from James: So I’ve been podcasting for, gosh, 11 years—over 1500 episodes. And through that whole journey, PodcastOne always stood out to me. They recently went public, and today I’ve got Rob Ellin and Kit Gray joining me. What’s the future of podcasting? If you're thinking about starting a podcast—or wondering how to grow one you already have—this episode's for you. These guys helped shape the entire industry, and they're sharing what works now, what doesn't, and how creators and networ...
May 24, 2025•47 min•Ep. 1326
Notes from James: This is where a lot of people quit—but you won’t. This episode is about pushing through the dip that comes when writing gets tough. I give you tools I’ve used across 25+ books to keep going, stay motivated, and write better. Episode Descriptions: This is Part 3 of my 30-day writing series—and we’re getting into the real tools that will make your writing not just better, but publishable. If you’ve ever stared at a blank page and felt overwhelmed, stuck, or unsure of where to go ...
May 22, 2025•49 min•Ep. 1325
Notes from James: The biggest lie about writing is that it takes years. I’ve written multiple books in less than a month—including bestsellers. With the right system, anyone can do this. In this episode, I break down how to structure your first book and why your life experience, not your grammar, is your superpower. You’ll also hear my take on AI writing, and why your personal story is something no algorithm can ever replicate. Episode Highlights: Yes, you really can write and publish a great bo...
May 18, 2025•43 min•Ep. 1324
Notes from James: I’ve written 25 books—some huge hits, some total flops—and what I’ve learned is this: anyone can write a book, but not everyone gives themselves permission to start. This episode is the foundation. I break down the mindset, motivation, and structure you need to go from blank page to published book—even if you’ve never written a word before. So you want to write a book. Where do you even start? In this kickoff to my new series on writing and publishing a book in just 30 days, I ...
May 16, 2025•37 min•Ep. 1323
A Note from James: Sunny Ray is working on an incredible project involving Bitcoin and his company, Matador. They’re digitizing gold—turning it into crypto—and he’s a Bitcoin maximalist. That’s different from my stance: I think there are many crypto tokens that are useful for specific purposes. But Sonny’s view is clear—Bitcoin is the foundation. We talk about what digital gold really means, why tokenization is so important, and how the biggest institutions in the world—like BlackRock—are embrac...
May 09, 2025•58 min•Ep. 1322
A Note from James: So Dr. Oz—television personality turned government official—this is such an interesting thing. He's going to be the new administrator of the Center for Medicare and Medicaid Services, CMS. He’s going to be in charge of all Medicare and Medicaid. What does he know or think about these parts of our government? Medicare and Medicaid, combined with Social Security, make up the biggest part of government spending. So it'd be interesting to know what he thinks. On his show, he’d tal...
May 07, 2025•36 min•Ep. 1321
A Note from James: Marty Makary is the new head of the FDA, but he is also an old friend of the podcast. He's been on several times, and it's really important to know how this is going to be a new and different FDA, and it's going to be molded by Marty's very specific opinions about healthcare and the medical industry—and here they are. Episode Description: In this episode, James reconnects with Dr. Marty Makary, now heading the FDA, to discuss what’s broken in the American healthcare system—and...
May 06, 2025•1 hr 30 min•Ep. 1320
A Note from James: The Data Republican —it almost sounds like a superhero name. And in a way, she is. She’s been single-handedly uncovering massive amounts of government waste and inefficiency. It’s honestly unbelievable. And regardless of whether you're a Democrat, Republican, Independent, or anything else, I think we can all agree: there shouldn’t be waste or fraud in the government. You’ve heard the old stories—like the military buying a pencil for $6 million. Those weren’t urban legends. The...
Apr 30, 2025•39 min•Ep. 1319
A Note from James: So I gave a little talk at the Full Stack Business Builder Conference. Basically, a conference for entrepreneurs, VCs, technologists, aspiring entrepreneurs. It was more of a Q&A, where the moderator, Peter Satton, asked me questions, but also took questions from the audience. A big concern for many people was, what if I have no qualifications at what I'm interested in doing? And I have to admit, I've probably never been qualified for anything I've ever done. I described h...
Apr 25, 2025•1 hr 1 min•Ep. 1318
A Note from James: Oh my gosh. This guy was thrown in jail for 65 years—and he deserved it. You'll hear about his crimes and misdemeanors. He started as a superstar quarterback, high school and college hero turned meth addict, and eventually became a hardcore RICO gang criminal. Sentenced to essentially life in prison, Damon's story is genuinely one of the most inspirational I've heard. He's got a bunch of books out—his latest, Six Dimes and a Nickel: Life Lessons to Empower Change , just came o...
Apr 23, 2025•1 hr 28 min•Ep. 1317
Notes from James: I don’t care if you’ve never written a word before—if you’ve lived, you have a story worth telling. The people who write the most impactful books aren’t the most famous or the best trained. They’re the ones who tell the truth with clarity and heart. In this episode, I show you how to do exactly that. You’ll learn how to structure your life story for emotional and commercial impact, and how to weave in other stories, research, and personal growth without losing the power of your...
Apr 18, 2025•43 min•Ep. 1316
Notes from James: Here’s the truth: if my great-great-great grandfather had written anything —just 10 pages about his daily life—I’d treasure it like gold. And I promise, your great-grandkids will feel the same about your story. You don’t need to be a celebrity to write something that matters. You just need to be honest. Whether you're sharing how you survived grief, learned to say no, built new habits, or rebuilt your life after failure—your story could help someone else. And it could help you ...
Apr 16, 2025•47 min•Ep. 1315
A Note from James: I can't think of anything more boring to talk about than tariffs, but right now, I can't think of anything more interesting either. Tariffs are dominating the news, stock markets are crashing, and everyone is scared. Are tariffs good or bad? Is Trump wrecking the economy or saving it? I'm going to address these questions, looking at what tariffs aim to achieve, their impact on the economy, the stock market, inflation, and even Bitcoin. Let's set aside politics and try to under...
Apr 09, 2025•42 min•Ep. 1314
