Fred Smith founded FedEx on an idea everyone told him would fail and built it into an $88 billion empire that changed how the world moves. In this episode, we dive into how he built FedEx and the lessons he learned along the way. This story proves that impossible is just another word for opportunity. ----- Timestamps: (00:00) Introduction (03:36) Part 1: The Boy Who Wouldn't Stay Down (15:52) Part 2: The Impossible Company (29:36) Part 3: The Empire Builder (38:12) Epilogue: From Crisis to Legacy (1993–2025) (40:55) Important Things That Didn’t Make It Into the Episode (43:55) Lessons from Fred Smith ----- Upgrade: Get a hand edited transcripts and ad free experiences along with my thoughts and reflections at the end of every conversation. Learn more @ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------ Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------ Follow Shane Parrish X ⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠ Insta @farnamstreet LinkedIn Shane Parrish ------ This episode is for informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

Benedict Evans has been calling tech shifts for decades. Now he says forget the hype: AI isn't the new electricity. It's the biggest change since the iPhone, and that's plenty big enough. We talk about why everyone gets platform shifts wrong, where Google's actually vulnerable, and what real people do with AI when nobody's watching. Evans sees patterns others don't. This conversation will change how you think about what's actually happening versus what everyone says is happening. ----- Approximate Timestamps: (00:00) Introduction (01:04) What's your Most Controversial Take On AI? (05:11) Platform Shifts - The Rise Of Automatic Elevators (10:07) Profit Margins In AI (26:37) What Are The Questions We Aren't Asking About AI (39:41) What Benedict Uses AI For (44:21) Thinking By Writing (47:35) Can AI Make Something Original? (52:31) Advice for Students In The Age Of AI? (59:32) Who Will Win The AI Race? (1:11:09) What Is Success For You? ----- Thanks to our sponsors for this episode: SHOPIFY: Sign up for your one-dollar-per-month trial period at ⁠www.shopify.com/knowledgeproject ⁠ ReMarkable for sponsoring this episode. Get your paper tablet at ⁠⁠reMarkable.com⁠⁠ today NOTION MAIL: Get Notion Mail for free right now at ⁠⁠notion.com/knowledgeproject ----- Upgrade: Get a hand edited transcripts and ad free experiences along with my thoughts and reflections at the end of every conversation. Learn more @ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------ Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------ Follow Shane Parrish X ⁠⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠⁠ Insta ⁠@farnamstreet⁠ LinkedIn ⁠Shane Parrish Learn more about your ad choices. Visit megaphone.fm/adchoices

The most influential retailer you’ve never heard of. How Sol Price invented the warehouse club and a philosophy that still runs Costco and Amazon. Have you ever wondered why you can still buy a hot dog and soda for $1.50 today at Costco? We can thank Sol Price for that. To him, keeping promises to customers mattered more than profit margins. Sam Walton said he borrowed more ideas from Sol Price than anyone else. Jim Sinegal of Costco said, “I didn’t learn a lot from Sol. I learned everything.” Jeff Bezos studied him. Home Depot echoed him. He invented the warehouse club, pioneered membership retail and built two multi-billion-dollar companies. The real lessons aren’t about what he built, but how he did it. This is the story of how a lawyer with no retail experience created an industry, mentored his competition, and proved that nice guys don't always finish last. Sol Price founded FedMart and Price Club, pioneering the membership warehouse model that inspired Costco and Sam’s Club. His principles—limited selection, fair wages, capped markups, no loss leaders—shaped modern retail through disciples like Jim Sinegal (Costco), Sam Walton (Walmart/Sam’s Club), Bernie Marcus (Home Depot), and influenced Jeff Bezos (Prime). ------ Approximate Timestamps: (00:00) Introduction (02:01) Early Years (08:29) Starting FedMart (28:33) Price Club (36:19) When Students Surpass the Teacher (42:09) The Teacher's Last Lesson (43:46) Reflections And Lessons ------ Upgrade: Get a hand edited transcripts and ad free experiences along with my thoughts and reflections at the end of every conversation. Learn more @ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------ Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠⁠⁠ ------ Follow Shane Parrish X ⁠⁠⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠⁠⁠ Insta ⁠⁠@farnamstreet⁠⁠ LinkedIn ⁠⁠Shane Parrish⁠ ------ This episode is for informational purposes only. Learn more about your ad choices. Visit megaphone.fm/adchoices

When Katharine Graham took over the Washington Post in 1963, she was a shy socialite who'd never run anything. By retirement, she'd taken down a president, ended the most violent strike in a generation, and built one of the best-performing companies in American history. Graham had no training, no experience, not even confidence. Just a newspaper bleeding money and a government that expected her to fall in line. When her editors brought her stolen classified documents, her lawyers begged her not to publish. They said it would destroy the company. She published them anyway. Nixon came after her, attacking her with the full force of the executive. Then Watergate. For nearly a year she was ridiculed and isolated while pursuing the story that would eventually bring down the president. Graham proved that you can grow into a job that initially seems impossible and no amount of training can substitute for having the right values and the courage to act on them. ------ 10 Lessons from Katharine Graham: ⁠⁠⁠https://fs.blog/knowledge-project-podcast/outliers-katharine-graham/ ------ Approximate timestamps: (0:00) Start (02:19) The Making of an Unlikely Heiress (10:15) The Education of a Publisher’s Wife (22:16) Learning to Lead (30:46) Becoming a Media Titan (44:12) Legacy (47:59) Reflections + Lessons ------ Thanks to ReMarkable for sponsoring this episode. Get your paper tablet at reMarkable.com today ------ Upgrade: Get a hand edited transcripts and ad free experiences along with my thoughts and reflections at the end of every conversation. Learn more @ ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ ------ Newsletter: The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠⁠ ------Follow Shane Parrish X ⁠⁠⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠⁠⁠ Insta ⁠⁠@farnamstreet⁠⁠ LinkedIn ⁠⁠Shane Parrish⁠ ------ This episode is for informational purposes only and contains the lessons I learned reading her memoir, Personal History and watching Becoming Katharine Graham. ------ Check out our website for all stock video and photo credits. Episode photo sourced from: iwmf.org/community/katharine-graham/ Learn more about your ad choices. Visit megaphone.fm/adchoices

Daniel Kahneman won the Nobel Prize for proving we're not as rational as we think. In this timeless conversation we discuss how to think clearly in a world full of noise, the invisible forces that cloud our judgement, and why more information doesn't equal better thinking. Kahneman also reveals the mental model he discovered at 22 that still guides elite teams today. Approximate timestamps: (00:36) – Episode Introduction (05:37) – Daniel Kahneman on Childhood and Early Psychology (12:44) – Influences and Career Path (15:32) – Working with Amos Tversky (17:20) – Happiness vs. Life Satisfaction (21:04) – Changing Behavior: Myths and Realities (24:38) – Psychological Forces Behind Behavior (28:02) – Understanding Motivation and Situational Forces (30:45) – Situational Awareness and Clear Thinking (34:11) – Intuition, Judgment, and Algorithms (39:33) – Improving Decision-Making with Structured Processes (43:26) – Organizational Thinking and Dissent (46:00) – Judgment Quality and Biases (50:12) – Teaching Negotiation Through Understanding (52:14) – Procedures That Elevate Group Thinking (55:30) – Recording and Reviewing Decisions (57:58) – The Concept of Noise in Decision-Making (01:01:14) – Reducing Noise and Improving Accuracy (01:04:09) – Replication Crisis and Changing Beliefs (01:08:21) – Why Psychologists Overestimate Their Hypotheses (01:12:20) – Closing Thoughts and Gratitude Thanks to MINT MOBILE for sponsoring this episode: Get this new customer offer and your 3-month Unlimited wireless plan for just 15 bucks a month at MINTMOBILE.com/KNOWLEDGEPROJECT. Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠⁠ Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠⁠ and get your own private feed. Watch on YouTube: ⁠⁠⁠⁠⁠⁠@tkppodcast Photograph: Richard Saker/The Guardian Follow Shane Parrish X ⁠⁠⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠⁠⁠ Insta ⁠⁠@farnamstreet⁠⁠ LinkedIn ⁠⁠Shane Parrish⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

They weren’t employees. They were partners. Les Schwab didn’t build a company. He built a culture. This episode reveals how one small-town tire dealer scaled to $3 billion by turning customers into evangelists and employees into owners. Somewhere between changing his first flat tire and opening his 410th Les Schwab Tire Center, Les discovered something profound: his people weren't just working for him, they were working with him. They weren't building his dream, they were building their own. This episode is a case study on how strategy, incentives, and trust create massive advantages that resources can’t buy. When investment bankers offered Schwab billions to sell his empire, he refused after asking himself just one question: “What would I do with the money?” Les Schwab understood something most never learn: the real wealth isn't in what you keep. Approximate timestamps: Subject to variation due to dynamically inserted ads: (01:49) Roots (11:21) In Business (27:50) Building an Empire (40:18) Maturation and Legacy (48:21) Reflections from Les Schwab (51:22) Lessons from Les Schwab This episode is for informational purposes only and is based on Pride in Performance: Keep It Going by Les Schwab Thanks to Basecamp for sponsoring this episode: basecamp.com/knowledgeproject Check out highlights from this book in our repository, and find key lessons from Schwab here: https://www.fs.blog/knowledge-project-podcast/outliers-les-schwab Upgrade—If you want to hear my thoughts and reflections at the end of all episodes, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠⁠ and get your own private feed. Newsletter—The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠ Follow Shane Parrish X ⁠⁠⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠⁠⁠ Insta ⁠⁠@farnamstreet⁠⁠ LinkedIn ⁠⁠Shane Parrish⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Shopify’s Harley Finkelstein reveals the one standard that actually scales your career and your family. Harley shares why stepping down as COO was his hardest choice, the family motto that guides his daughters, and what makes someone good at storytelling. They discuss AI's real advantage, the calendar system that keeps him accountable, and how he maintains high standards. If this gives you one standard to raise your team—or your family—share it with a friend who needs to hear it today. ------------ About Harley: Harley Finkelstein is the President of Shopify. He leads storytelling, external relations, and company energy—translating world-class product into world-class adoption. Approximate timestamps: (00:02:10) Living With Unreasonably High Standards (00:03:40) Generational Trauma and Family Relationships (00:07:52) Growing Up With Adverse Circumstances (00:14:42) Prioritizing In Life And Becoming World Class (00:24:45) Requalifying For Your Job (00:30:05) Mindset for Professional Growth and Success (00:31:33) How To Find A Great Business Partner (00:32:57) Switching From COO Of Shopify To President/Chief Storyteller (00:40:34) How Storytelling Impacts Shopify (00:42:00) How To Get Better At Storytelling (00:46:13) Shopify And How Commerce Has Evolved (00:49:27) Forced Entrepreneurship Vs Passion-Based Entrepreneurship (00:51:34) Mentorship (00:59:41) Overcoming Failure And Rejection (01:02:46) Out Caring Is More Important Than IQ, EQ, Raw Talent (01:06:07) Parenting And Teaching A Hardwork Ethic (01:11:23) Teaching Resilience Thanks to our sponsor for supporting this episode: SHOPIFY: Sign up for your one-dollar-per-month trial period at shopify.com/knowledgeproject MINT MOBILE: Get your 3-month Unlimited wireless plan for just 15 bucks a month at mintmobile.com/knowledgeproject Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠⁠fs.blog/newsletter⁠⁠⁠⁠⁠ Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠⁠ and get your own private feed. Watch on YouTube: ⁠⁠⁠⁠⁠@tkppodcast Follow Shane Parrish X ⁠⁠⁠⁠⁠⁠@ShaneAParrish⁠⁠⁠⁠⁠⁠ Insta ⁠⁠@farnamstreet⁠⁠ LinkedIn ⁠⁠Shane Parrish⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

The job was editor-in-chief. The goal was to become the platform. And she did. Once she made it to the top, she didn’t just edit Vogue. She reinvented the power structures beneath it. This episode unpacks how a British girl who couldn’t type built the most bulletproof career in media, survived five decades of disruption, and made herself indispensable to fashion, politics, and culture. You’ll hear how she weaponized speed over perfection, fired half the Vogue staff in three days, and turned a porn-funded job into a fashion laboratory. Why she said “Your job” when asked what she wanted. Why she put Madonna on the cover at the peak of a scandal. Why standards—not popularity—are her real moat. It’s not about fashion. It’s about building systems no one can take from you. Most people aim for realistic. Anna Wintour named her destination—Editor of Vogue—at sixteen, then built a ladder no one else could climb. This episode is for informational purposes only and is based on Amy Odell’s Anna: The Biography. Simon & Schuster, 2022. Check out highlights from these books in our repository, and find key lessons from Wintour here—⁠⁠⁠⁠https://fs.blog/knowledge-project-podcast/outliers-anna-wintour/ Approximate timestamps: Subject to variation due to dynamically inserted ads: (03:48) PART 1: A Childhood Defined: The Girl Who Couldn’t Type (05:50) Anna Chooses Her Path (07:28) Learning by Drowning (09:46) The Tyranny of Standards (12:01) When Merit Meets Reality (13:44) PART 2: Conquering New York: The Quiet Revolutionary (16:05) Quiet Focus (18:10) The Best Worst Job (19:29) A Reputation from Nothing (21:00) In the Wilderness (22:39) The Preparation Advantage (25:40) The Audacity Play (27:22) The London Interlude (28:44) The Execution (30:19) PART 3: Vogue’s Transformation: The Devil in the Details (32:04) Speed as Strategy (34:56) The Celebrity Revolution (38:44) The Three-Assistant Solution (41:07) Balancing Art and Commerce (43:11) Cannibalizing Yourself First (46:46) PART 4: Anna’s Empire: The Power of Compartmentalization (48:05) The Empire Strategy (49:44) Crisis as Opportunity (51:58) The Digital Reinvention (53:27) The Currency of Influence (54:36) The Machine Anna Built (56:11) The Persistence of Power (58:23) Reflections, afterthoughts, and lessons Upgrade—If you want to hear my thoughts and reflections at the end of all episodes, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠⁠ and get your own private feed. Newsletter—The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠⁠fs.blog/newsletter⁠ Follow Shane on X at: ⁠x.com/ShaneAParrish Learn more about your ad choices. Visit megaphone.fm/adchoices

Harvey Firestone built one of America’s great industrial empires from scratch, transforming from a farm boy to Henry Ford’s key partner. This episode reveals timeless principles about building businesses through booms, busts, and technological disruptions. This episode is based on the biography Men and Rubber: The Story of Business. Check out The Firestone Principles: 12 Timeless Lessons from an Industrial Pioneer: ⁠⁠⁠https://fs.blog/knowledge-project-podcast/outliers-harvey-firestone/ (03:00) PART 1: The Best Businessman I Ever Knew (06:50) The Vanilla Extract Lesson (10:23) When Premium Doesn’t Matter (12:05) PART 2: Right Beneath the Wheels (14:21) The Back of an Envelope (16:36) If Two of Us Stay, Neither Makes Money (18:39) Betting on what Doesn’t Change (20:55) The Accidental Breakfast (24:53) The Third Option (28:19) PART 3: The Innovators Dilemma: Pneumatic Tires (32:24) The Ford Connection: A Partnership of Outsiders (35:23) Navigating the Crisis (37:17) The Underdog’s Advantage (39:24) The Million Dollar Milestone (43:10) Weathering the Panic of 1907 (45:55) The Simplicity Imperative (51:25) PART 4: The Ship-by-Truck Revolution (54:31) The Boom That Hid Everything (56:11) The 25% Solution (01:01:42) Cutting to the Bone (01:04:25) PART 5: Why He Never Stopped (01:06:54) The Human Element (01:08:09) The Legacy (01:10:05) Reflections, afterthoughts, and lessons Upgrade—If you want to hear my thoughts and reflections at the end of all episodes, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠⁠⁠ and get your own private feed. Newsletter—The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠⁠⁠fs.blog/newsletter Follow Shane on X at: x.com/ShaneAParrish Learn more about your ad choices. Visit megaphone.fm/adchoices

Rose Blumkin didn’t just build a business. She revolutionized retail. After fleeing Russia with $66 in her purse, she opened a basement furniture store in Omaha at 43 years old—with no English, no education, and no connections. Her formula? Sell cheap, tell the truth, don't cheat the customer. Nebraska Furniture Mart would survive depressions, fires, lawsuits, tornadoes—and eventually become a billion-dollar empire Warren Buffett called “the ideal business.” Learn how Mrs. B’s relentless focus, radical simplicity, and unbreakable work ethic built an empire from scratch—and what her story teaches us about business, resilience, and the power of earned trust. This episode is for informational purposes only and most of the research came from "Women of Berkshire Hathaway" and oral history interviews with Rose Blumkin and her daughter Frances. Check out highlights from this book in our repository, and find key lessons from Blumkin here — ⁠fs.blog/knowledge-project-podcast/outliers-rose-blumkin (03:20) PART 1: Early Childhood (07:10) A Natural Entrepreneur (09:37) PART 2: Building an Empire (12:53) The Competition (15:54) The Passing of Isadore (18:32) Expansion through Hardship (20:32) Natural Instinct for Character (25:15) PART 3: The $60m Handshake / The Buffett Connection (28:25) A Rebel at 96 (33:47) Reflections, afterthoughts, and lessons Thanks to our sponsors for supporting this episode: MOMENTOUS: Head to ⁠livemomentous.com⁠ and use code KNOWLEDGEPROJECT for 35% off your first subscription. NOTION MAIL: Get Notion Mail for free right now at notion.com/knowledgeproject Upgrade — If you want to hear my thoughts and reflections at the end of all episodes, join our membership: ⁠⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠⁠ and get your own private feed. Newsletter — The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at ⁠fs.blog/newsletter Learn more about your ad choices. Visit megaphone.fm/adchoices

What happens when one of the most legendary minds in tech delves deep into the real workings of modern AI? A 2-hour long masterclass that you don’t want to miss. Bret Taylor, current chairman of OpenAI, unpacks why AI is transforming software engineering forever, how founders can survive acquisition (he’s done it twice), and why the true bottlenecks in AI aren’t what most think. Drawing on his extensive experiences at Facebook, Google, Twitter and more, he explains why the next phase of AI won’t just be about building better models—it’s about creating entirely new ways for us to work with them. Bret exposes the reality gap between what AI insiders understand and what everyone else believes. Listen now to recalibrate your thinking before your competitors do. (00:02:46) Aha Moments with AI (00:04:43) Founders Working for Founders (00:07:59) Acquisition Process (00:14:14) The Role of a Board (00:17:05) Founder Mode (00:20:29) Engineers as Leaders (00:24:54) Applying First Principles in Business (00:28:43) The Future of Software Engineering (00:35:11) Efficiency and Verification of AI-Generated Code (00:36:46) The Future of Software Development (00:37:24) Defining AGI (00:47:03) AI Self-Improvement? (00:47:58) Safety Measures and Supervision in AI (00:49:47) Benefiting Humanity and AI Safety (00:54:06) Regulation and Geopolitical Landscape in AI (00:55:58) Foundation Models and Frontier Models (01:01:06) Economics and Open Source Models (01:05:18) AI and AGI Accessibility (01:07:42) Optimizing AI Prompts (01:11:18) Creating an AI Superpower (01:14:12) Future of Education and AI (01:19:34) The Impact of AI on Job Roles (01:21:58) AI in Problem-Solving and Research (01:25:24) Importance of AI Context Window (01:27:37) AI Output and Intellectual Property (01:30:09) Google Maps Launch and Challenges (01:37:57) Long-Term Investment in AI (01:43:02) Balancing Work and Family Life (01:44:25) Building Sierra as an Enduring Company (01:45:38) Lessons from Tech Company Lifecycles (01:48:31) Definition and Applications of AI Agents (01:53:56) Challenges and Importance of Branded AI Agents (01:56:28) Fending Off Complacency in Companies (02:01:21) Customer Obsession and Leadership in Companies Bret Taylor is currently the Chairman of OpenAI and CEO of Sierra. Previously, he was the CTO of Facebook, Chairman of the board for X, and the Co-CEO of Salesforce. Newsletter - The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter Upgrade — If you want to hear my thoughts and reflections at the end of the episode, join our membership: ⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠ and get your own private feed. Watch on YouTube: @tkppodcast Learn more about your ad choices. Visit megaphone.fm/adchoices

Cornelius Vanderbilt was a force in 19th century America, playing a pivotal role in transitioning the U.S. economy from rural mercantilism to industrial corporate capitalism. Vanderbilt didn't just compete—he dominated; and didn’t just dominate one industry—he conquered three: ferries, steamships, and railroads. He understood that power lay in controlling infrastructure and not just operating within it. His cutthroat tactics were both feared and admired but his vision for what the economy could be was undeniable. This is the story of how Vanderbilt turned calculated aggression into an art form, how he endured more pain than his competitors, and how he built systems that outlived him. Learn the mindset, strategies, and brutal lessons behind his dominance; the game of business hasn’t changed as much as you think. (02:20) Prologue (05:12) PART 1 - The Dutch Inheritance (08:21) The Young Boatman (12:30) Capitalizing on War (15:27) General Merchant of the Sea (19:29) PART 2 - The Meeting That Changed Everything (21:48) The Steamboat Wars (24:12) The Anti-Monopoly Crusader (27:06) The Rise of the Commodore (32:08) The Monopolist's Nemesis (34:58) PART 3 - Sole Control (37:28) Prometheus (40:18) Star of the West (44:06) Europe and Betrayal (48:15) The Independent Line (50:13) PART 4 - The Commodore’s Return (51:55) Gray Eyed Man of Destiny (53:36) The Conspiracy (54:41) Finishing Walker (55:54) Conquering the Seas (58:13) America's Wealthiest Citizen (60:47) PART 5 - Vanderbilt's Railroad Dominance (01:01:59) The Path to Confrontation (01:03:37) The Breaking Point (01:04:43) The Power to Punish (01:06:32) The Collapse (01:07:50) The Silent Conquest (01:08:57) The Consolidation (01:10:54) The Legacy (01:12:15) FINAL PART - Vanderbilt: The Architect of Modern American Business (01:14:19) Reflections This episode is for informational purposes only and most of the research came from reading The First Tycoon by T.J. Stiles and Tycoon’s War by Stephen Dando-Collins. Check out highlights from these books in our repository, and find key lessons from Cornelius Vanderbilt here — fs.blog/knowledge-project-podcast/outliers-cornelius-vanderbilt Upgrade — If you want to hear my thoughts and reflections at the end of all episodes, join our membership: ⁠⁠⁠⁠⁠⁠⁠fs.blog/membership⁠⁠ and get your own private feed. Newsletter — The Brain Food newsletter delivers actionable insights and thoughtful ideas every Sunday. It takes 5 minutes to read, and it’s completely free. Learn more and sign up at fs.blog/newsletter Learn more about your ad choices. Visit megaphone.fm/adchoices