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Jeremy Stern is the editor-in-chief of Colossus, where he writes long-form profiles of leading entrepreneurs and investors. He goes behind the scenes of his reporting on Mark Zuckerberg, explaining how months of interviews revealed Zuckerberg’s fascination with Augustus, relentless competitive drive and commitment to building Meta for decades. Jeremy discusses why Meta’s distribution and infrastructure could give it an advantage in AI and why some founders seem incapable of walking away. He explains how a question about defense technology became his first profile, on Palmer Luckey, and why he brings the craft of fiction and poetry to writing about business. Jeremy also describes Scott Wu’s combination of mathematical genius, natural leadership and authenticity, and how Josh Kushner’s family history shaped his exploration of Thrive Capital and the American dream. The conversation closes with the story of Jeremy’s Russian professor, whose belief that people have an obligation to their gifts changed his life and helped shape how he sees the people he writes about. Show notes: https://www.davidsenra.com/episode/jeremy-stern Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra Learn more about your ad choices. Visit megaphone.fm/adchoices

Alexander Taubman is the co-founder and CEO of Long Lake, a company that buys established service businesses and uses AI to improve how they operate. He explains Long Lake’s $6.3 billion deal for American Express Global Business Travel, why deploying AI in the real economy is difficult and why he sees productivity gains creating more jobs as businesses grow. Alex describes how Nexus, Long Lake’s AI platform, connects models to business data and workflows, why its engineers work alongside employees in the field and why he wants to own businesses rather than sell software. He shares how his grandfather’s idea of “threshold resistance” applies to AI adoption, what he learned at Goldman Sachs and Oaktree and how investing in founder-owned businesses through Taubman Capital prepared him to build Long Lake. Alex also discusses the influence of Danaher, Henry Singleton and John Malone, why he values partners who make him more ambitious and why Long Lake plans to hold its businesses for decades. Including Amex GBT, he expects more than $4 billion in combined revenue the following year and explains why he believes long-term compounding could eventually build a trillion-dollar company. Show notes: https://www.davidsenra.com/episode/alexander-taubman Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) The $6.3 billion Amex GBT deal (00:01:21) Bringing AI to the real economy (00:06:17) Why greater productivity can mean more jobs (00:11:29) A prepared mind and a tight acquisition filter (00:16:01) Nexus and the AI platform behind Long Lake (00:17:32) Put the engineers where the work happens (00:20:36) Why own the businesses instead of selling software? (00:22:28) Build tools people want to use (00:25:24) A high bar for talent, acquisitions and technology (00:28:03) What his grandfather taught him about removing friction (00:36:40) Learning capital allocation at Goldman Sachs and Oaktree (00:41:01) Buying founder-owned businesses with permanent capital (00:44:35) How the Long Lake team came together (00:47:26) The best partners make you more ambitious (00:49:28) More than $4 billion in projected revenue (00:53:32) Why going public could expand Long Lake’s ambition (00:54:23) Henry Singleton and staying flexible (00:55:57) John Malone and the businesses that will endure (00:57:57) Why Long Lake doesn’t plan to sell (01:00:13) Could Long Lake become a trillion-dollar company? Learn more about your ad choices. Visit megaphone.fm/adchoices

Ronnie Fieg is the founder, CEO and creative director of Kith. At 13, he turned down an envelope of cash at his bar mitzvah to ask his cousin for a job, then spent 15 years working his way up from stock boy to buyer at David Z. He explains how growing up in Queens and working on 8th Street shaped his taste, how his first ASICS Gel-Lyte III collaboration landed on the front of The Wall Street Journal’s Pursuits section and why he still designs every product for himself first. Ronnie describes why Kith refuses to wholesale or license, why he opens new physical stores as online sales grow and why he believes luxury should mean how much people love what they buy. He also details how a failed white chocolate bread idea became Kith Treats, how he prices product so customers get more than they pay for and what he felt seeing all 1,800 of his shoe designs laid out in chronological order. Ronnie shares how an obsession with padel led to Kith Ivy, why he is expanding into hospitality with Ronnie’s and why growing up before the internet forced him to develop his own point of view. Show notes: https://davidsenra.com/episode/ronnie-fieg Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) You can’t work backwards from money (00:04:43) “Keep the envelope. I want a job.” (00:10:25) Why the CEO is also the fit model (00:18:43) The childhood shoe that launched his career (00:20:52) The Wall Street Journal, a line down the block and a visit from Adidas (00:26:48) Get rid of the crap (00:31:09) What luxury should actually mean (00:32:40) Why Kith doesn’t wholesale or license (00:38:24) Building the opposite of an arrogant sneaker shop (00:40:39) The Italian crook who registered Kith’s trademark (00:52:02) How a $20 deli experiment became Kith Treats (00:55:11) Serve your customers, don’t chase new ones (00:59:35) Always give people more than they pay for (01:02:41) Seeing 15 years of work laid out on the floor (01:12:00) Growing up before the algorithm (01:25:46) How a padel obsession created Kith Ivy Learn more about your ad choices. Visit megaphone.fm/adchoices

Peter Rahal is the co-founder of RXBAR, David Protein, and Medici Brands. After selling RXBAR for $600 million, he tried investing and quickly discovered he was miserable watching other people run companies. He explains why he returned to protein bars, why founders must deeply understand their products and how he plans to build the most important food company of the 21st century. Peter describes the intelligence, beauty and discipline behind David's brand, how growing up with dyslexia shaped his competitive drive and why he channels anger and resentment into company building. He also details his approach to hiring former founders, building a culture of truth seeking and humility and treating the organization itself as a product. Peter walks through the acquisition of his critical ingredient supplier, Epogee, the supply agreements that protected his business and what he would change about communicating the decision to other entrepreneurs. He shares why he chose Greenoaks as an investor, why speed matters more than maximizing a fundraising valuation and how he is building a decentralized organization where leaders master their products, confront problems and earn their autonomy. Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) Life after selling RXBAR for $600 million (00:07:29) Going all in and burning the boats (00:11:48) Building the most important food company of the 21st century (00:13:49) How a brand is like a human being (00:21:07) Why Peter always chooses the hard path (00:28:17) From zero to $300 million in two years (00:29:59) Why Peter started selling frozen cod (00:32:51) The organization is the product (00:36:56) Why he recruits former founders (00:41:15) Buying his supplier and victimizing his competitors (00:51:56) How Neil Mehta and Greenoaks earned a spot on the cap table (00:55:47) How Peter fundraises (01:00:31) Running a business is like a river (01:04:16) Why the company is named Medici (01:06:28) Bureaucracy is not inevitable (01:11:48) Why Peter has 25 direct reports (01:16:06) Peter's principle of reactionary leadership support (01:17:45) On divine discontent and loving the fight Learn more about your ad choices. Visit megaphone.fm/adchoices

Luca Ferrari is a co-founder of Bending Spoons, the technology company he built with his partners by rethinking how software businesses should hire, operate and allocate capital. He explains why Bending Spoons aspires to build “the best company there ever was,” why it favors raw talent and drive over experience and how a centralized talent team uses testing and more than 100 signals to identify exceptional people early. Luca describes the company’s culture of extreme ownership and relentless simplification, including why employees are given more work than they can possibly complete, why teams rotate across businesses and why Bending Spoons eliminated traditional job titles. He also details the proprietary operating system and AI tools that allow small teams to run acquired products such as Evernote, why Bending Spoons buys businesses to hold and transform rather than sell and how operational excellence gives it an advantage in acquisitions. Luca closes by discussing going public, his approach to negotiation and capital allocation and why he believes logic and rationality are more reliable than blindly following data. Show notes: https://davidsenra.com/episode/luca-ferrari Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra Chapters (00:00:00) Fanatical founders building enduring companies (00:01:23) Luca on building the best company there ever was (00:04:22) The origins of Bending Spoons (00:05:47) Talent and why experience is overrated (00:15:05) Turning hiring into a science (00:23:30) Why Bending Spoons doesn't use bonuses (00:29:26) Why everyone in the company has the same job (00:42:41) On finding great potential and saturating their capacity (00:49:50) Insisting on a culture of extreme ownership (00:59:28) Luca's principle of relentless simplification (01:05:15) Why Bending Spoons doesn't use job titles (01:10:27) The proprietary operating system behind Bending Spoons (01:17:07) Why Bending Spoons isn't private equity (01:19:32) How Bending Spoons acquired & transformed Evernote (01:28:01) How Bending Spoons uses AI (01:40:42) How Bending Spoons thinks about capital allocation (01:43:50) Why procrastination without laziness is good (01:46:46) Operational excellence is not optional (01:49:07) How Bending Spoons negotiates acquisitions (01:54:47) Logic over numbers Learn more about your ad choices. Visit megaphone.fm/adchoices

Mati Staniszewski is the co-founder of ElevenLabs, an AI audio company he started in 2022 with his longtime friend Piotr Dąbkowski. He explains how a frustration with poorly dubbed content in Poland led them to build frontier speech technology, why ElevenLabs combines audio research with product deployment and how its focus on voice shapes where the company chooses to compete. Mati also describes the Palantir-inspired operating model behind ElevenLabs: small autonomous teams, a flat organization and forward deployed engineers who work directly with customers and feed what they learn back into the product. He discusses using AI to amplify human potential, helping people who have lost their voices speak again, why imperfections can make AI voices feel more human and his belief that voice will become one of the primary ways people interact with AI. After turning down multiple acquisition offers, Mati says he and Piotr are committed to building ElevenLabs independently and pursuing what they see as a rare opportunity to reshape how humans communicate with technology. Show notes: https://www.davidenra.com/mati-staniszewski Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra Chapters (00:00:00) Building an AI-Native Company Before ChatGPT (00:02:59) Why ElevenLabs Started With Audio & Dubbing (00:12:37) Research + Product Deployment: How ElevenLabs Is Built (00:16:15) Focus as a Competitive Advantage (00:18:47) Building an Ecosystem Around Voice (00:22:25) The Communication Platform & Deutsche Telekom (00:28:29) Forward Deployed Engineers & Lessons From Palantir (00:33:41) Flat Organizations, Transparency & AI-Native Management (00:37:19) Small Teams & Putting Engineers Everywhere (00:43:00) Where ElevenLabs Is Growing Fastest (00:44:38) Taste, Art & Science in AI (00:48:23) Using AI to Amplify Human Potential (00:55:19) Becoming an Entrepreneur & Building With Piotr (00:56:49) Why Mati Won't Sell ElevenLabs (01:04:01) Voice as the Interface for AI (01:06:49) Turning Conferences Into a Business Tool Learn more about your ad choices. Visit megaphone.fm/adchoices

Zach Dell is the co-founder of Base Power, an energy company on a mission to make electricity more affordable and reliable. His starting insight was that home batteries had the wrong business model. Companies sold expensive backup systems that sat idle most of the time. Base installs batteries at homes, retains ownership and operates them as a fleet: charging when electricity is cheap, discharging when it is expensive and providing backup when the grid goes down. The homeowner gets lower electricity bills and backup power. Base gets an asset it can put to work every day. Dell explains why batteries can make the existing grid more efficient, why installing them where people consume electricity helps overcome infrastructure bottlenecks and how Base serves both homeowners and utilities. His strategy is to build a compounding cost advantage through vertical integration and technology. That now includes Base Core, a battery designed and manufactured by the company, and a longer-term ambition to help meet the growing power demands of AI. Dell grew up watching his father, Michael Dell, build a company and knew from childhood that he wanted to become an entrepreneur. After several early ventures failed, he went into investing to study what makes a great business. He describes the “Dad Terminal”—ongoing conversations with his father about strategy, operations and the problems in front of them—and the lessons Base has adopted from former SpaceX employees. Engineers and manufacturing teams work close together, and the entire company organizes around a few clearly defined goals. He also explains the operating habits behind Base: monthly written updates, visible performance dashboards and a physical turtle placed on the desk of the person responsible for resolving a critical bottleneck. He keeps separate notebooks for working in the business and working on it, setting aside time each night to think on paper without distractions. He discusses building a beloved brand in energy, why his co-founder conversations focus on what is going wrong and why Base is his last company. His ambition is a lifelong effort to make, move, store and sell electricity more affordably and reliably. Show notes: https://www.davidsenra.com/zach-dell Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) Energy Abundance & the Power Demands of AI (00:06:15) How Batteries Make the Grid More Efficient (00:09:09) Early Ventures & the Insight Behind Base (00:15:34) We Don't Sell Batteries. We Sell Electricity. (00:22:25) How Base Works With Utilities & Competes for Customers (00:30:44) Learning From Michael Dell: The "Dad Terminal" (00:32:22) Vertical Integration & Lessons From SpaceX (00:39:34) Writing Clearly & Making Time to Think (00:44:53) North Stars, Turtles & Relentless Execution (00:53:55) Learning From Great Founders & Building a Beloved Brand (00:56:27) What's Your Constraint? (01:06:26) Base Core & Taking Control of Manufacturing (01:11:02) A Lifelong Mission & the Last Company He'll Build Learn more about your ad choices. Visit megaphone.fm/adchoices

Doug Leone spent 26 years helping lead Sequoia Capital through successive eras of technological change. Born in Italy, he came to the United States without speaking English and carried the insecurity of an outsider into his career. That fear became fuel: whenever he felt himself falling behind, he forced himself to start over. After stepping down from Sequoia at 65 to make room for the next generation, he returned four years later. Now he considers himself a low-level analyst again, racing to understand an AI revolution that he believes is rewriting business more radically than anything he has seen before. Leone explains the three questions he asks before making an investment: Would he put his children's money into it? If he could make only 20 investments in his life, would this be one of them? Could it return the entire fund? He is interested only in extreme outliers—companies capable of returning 100 times the original investment—and says the biggest mistake venture investors make is selling their winners too early. Sequoia once owned enormous stakes in Apple, Cisco, Google and NVIDIA, but even the greatest investors failed to anticipate how long exceptional companies could continue compounding. His role as an investor is not to shape a founder's technology. It is to help turn a product into a business: recruiting the first team, building sales and marketing, navigating crucible moments and preserving the founder as the soul of the company. He describes backing David Vélez before Nubank existed, what Fred Luddy's unusual ServiceNow pitch revealed about him and why Sequoia looks for the same qualities in founders and its own partners: a hypercompetitive person with a heart of gold. Leone also discusses trust as the accelerant that makes business move quickly. Trust requires both competence and good intentions, and it is earned by helping founders when they are most vulnerable. He explains why founders should architect their boards as carefully as their products, why productive disagreement is different from argument and how to deliver difficult feedback so it can actually be heard. He closes with lessons from his longtime partner Michael Moritz: listen to the exact words people choose, put the other person first and always ask what a company could become if everything goes right. Show notes: https://www.davidsenra.com/episode/doug-leone Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) How to Dominate for Decades (00:03:17) Turning Fear Into a Tailwind (00:05:40) Immigrant Drive, Hard Work & the Beach Club (00:12:19) Simplifying Life & Choosing Discomfort (00:14:37) The Homeless Sequoia Partner With No Plan B (00:16:49) Stepping Down, Coming Back & Starting Over (00:20:04) Why AI Is Different From Every Previous Technology Shift (00:22:13) Doug's Three Investment Heuristics (00:23:52) The Cost of Selling Great Companies Too Early (00:25:39) Helping Founders Turn Products Into Businesses (00:28:28) David Vélez, Nubank & the Psychology of Founder Support (00:32:25) Why Founders Must Remain the Soul of the Company (00:36:13) Torturing Yourself Into Greatness (00:39:57) Don Valentine, Succession & the Sequoia School of Hard Knocks (00:44:28) Staying Grounded & Developing a Sniffer for People (00:47:46) Hypercompetitive With a Heart of Gold (00:50:13) Fred Luddy, Israeli Founders & Radical Directness (00:52:28) Trust Is the Accelerant of Business (00:59:57) Starting From Zero & Hunting for the Next Great Founder (01:05:59) Architect Your Board Like Your Product (01:10:24) Truth, Disagreement & the Art of Difficult Feedback (01:13:43) Humanity, Introversion & the Value of Relationships (01:18:18) What Doug Learned From Michael Moritz Learn more about your ad choices. Visit megaphone.fm/adchoices

Torsten Reil has spent his career working at the intersection of artificial intelligence, simulation and entrepreneurship. He began as a biologist studying neural networks and complex systems before founding NaturalMotion, whose technology was used in films including Lord of the Rings, Troy and Harry Potter and later in games including Grand Theft Auto and Red Dead Redemption. After building and selling NaturalMotion, he eventually returned to entrepreneurship to co-found Helsing, a European defense technology company focused on artificial intelligence and autonomous systems. Reil believes warfare is undergoing a fundamental shift from humans operating expensive weapons systems toward what he calls autonomous mass: large numbers of AI-controlled machines operating together. He explains why drones are making tanks, artillery and eventually crewed fighter jets increasingly vulnerable; how AI can navigate without GPS in jammed environments; and why Helsing developed Centaur, an AI fighter pilot that has controlled a real Saab Gripen in air combat against a human-operated aircraft. That work led Helsing to begin building its own autonomous fighter jet, the CA1 Europa. The underlying strategy is to combine simpler, mass-manufacturable hardware with increasingly capable software. Reil argues that future conflicts will become battles of materiel, making manufacturing capacity as important as technological sophistication. Helsing's HX-2 strike drone was redesigned to scale from dozens of units per month to a baseline of 1,000, with the ability to surge to 3,000. He also explains Helsing's concept of distributed “resilience factories,” which allow countries to manufacture systems domestically while reducing their dependence on vulnerable centralized production facilities. Reil also describes how he runs Helsing and why he considers talent density the most important ingredient in company performance and culture. The company closely monitors recruiting, conducts quarterly performance calibration and makes an unusually large investment in finding and retaining exceptional people. He discusses Helsing's values of “whatever it takes” and “the truth is in the field,” why founders should pursue ambitions large enough to matter, and why he believes commentary has little value compared with actually building something that changes the world. Show notes: https://www.davidsenra.com/episode/torsten-reil Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com Deel: https://deel.com/senra Chapters (00:00:00) Drones, Tanks & the Future of Warfare (00:07:08) Why Torsten Founded Helsing (00:09:27) Founder Conviction & Betting on European Defense (00:19:19) Helsing's Mission: Protecting Democracies (00:23:38) Programs of Record & Winning the Eurofighter Contract (00:28:35) Building a Superhuman AI Fighter Pilot (00:36:14) Deterrence, Autonomous Weapons & the Morality of Defense (00:42:11) Mass Manufacturing, Software & the Future of Materiel (00:48:33) Airbase Vulnerability, Procurement & Scaling Strike Drones (00:52:46) Talent Density, Hiring & Performance Management (00:59:44) How Torsten Hires Exceptional People (01:05:27) Helsing's Culture: Whatever It Takes & Truth Is in the Field (01:07:38) Deploying in Ukraine & the Weight of Defense Technology (01:10:50) NaturalMotion, Gaming & Torsten's Path Into AI (01:18:33) Outsiders, First Principles & Ambitious North Stars (01:20:54) Why Commentary Is Worthless & Founders Should Build Learn more about your ad choices. Visit megaphone.fm/adchoices

Sam Altman has spent his career at the intersection of startups, investing and artificial intelligence. He says he was fascinated by AI as a child in St. Louis, studied it in college and eventually helped start OpenAI in 2015 after concluding that the most important opportunities often begin as non-consensus bets. His experience investing in startups taught him to look for power laws, back unconventional talent and recognize the decisions that can change a company’s trajectory. At OpenAI, Altman says most of his effort goes toward research and compute. Scaling compute requires coordinating chips, fabrication plants, data centers, power systems, finance, policy, supply chains and logistics—what he describes as potentially the most expensive infrastructure project in history. He argues OpenAI should function primarily as a platform: one direct interface to powerful AI and one application programming interface that lets people build on top of it. That strategy requires killing good ideas to preserve resources for the great ones. Altman expects AI capabilities to advance faster than society and the economy can absorb them. Human habits and institutional inertia will slow the transition, which he believes may make it smoother. He also expects human connection to become more valuable and AI to enable a major increase in small-business formation. His central concern is that AI should expand human agency rather than concentrate power in a small number of companies, people or models. He also explains how Y Combinator shaped OpenAI’s operating philosophy: make non-consensus bets, put technical people in charge, ship early, learn from reality and iterate. Yet OpenAI required breaking the classic startup playbook. The organization spent four and a half years without launching a product and had to invent ways to measure research progress without customer feedback. On its first day, roughly a dozen people gathered in Greg Brockman’s apartment and quickly realized they did not know what to do next. Years of what Altman calls “chaotic stumbling” eventually produced the research path that led to GPT. Show notes: https://www.davidsenra.com/episode/sam-altman Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) Tobi Lütke, AI-Native Companies & Why Adoption Moves Slowly (00:05:45) Sam's Own Resistance to AI & the Missing iPhone Moment (00:10:00) Models, Compute, Power Laws & Non-Consensus Talent (00:18:37) From AI-Obsessed Kid to Founder, Investor & Back Again (00:23:19) Impossible Problems, Scientific Discovery & Human Connection (00:30:16) AI's Two Biggest Risks: Loss of Control & Centralized Power (00:33:09) Iterative Deployment, AI Safety & Learning From Reality (00:40:27) Why People Fear AI & the Coming Small-Business Boom (00:46:13) Context, Memory & the Next Way We Will Work With AI (00:49:17) OpenAI's Platform Strategy & Killing Good Ideas (00:53:20) Peter Thiel, Paul Graham & the Value of Nonlinear Thinkers (01:00:42) How Y Combinator Changed Startups & Shaped OpenAI (01:04:03) Learning More From Success & the Power of Repetition (01:09:45) Building OpenAI Without Customers, a Product or a Playbook (01:15:57) Letters to His Son & Preserving the Story Learn more about your ad choices. Visit megaphone.fm/adchoices

Travis Kalanick is best known for co-founding Uber and building it into one of the world’s largest transportation platforms. Before Uber, he spent years building Red Swoosh under extreme financial pressure. He says he took no salary for its first four years, repeatedly ran out of money and lost much of his social life to the company before eventually selling it. He later invested much of the proceeds in friends’ startups, becoming the first investor in Expensify. Kalanick started Uber at 33 and carried the intensity of those earlier years into the company. He describes operating with “precision, perfection and obsession” and continued running Uber with the mentality of someone worried about making the next grocery bill even after the company had reached a valuation of roughly $70 billion. Under his leadership, Uber expanded rapidly across cities and countries, creating a new category of app-based transportation and challenging the entrenched taxi systems that controlled many local markets. Uber’s growth depended on empowering young operators to build markets from scratch while maintaining tight control over the decisions that mattered most. Kalanick personally participated in the pricing process for the company’s first 20 to 30 cities, using each launch to refine a playbook that could eventually operate without him. He describes this management philosophy as finding the line between order and chaos: using the fewest possible rules while preserving the structure required to move quickly at scale. After leaving Uber, he returned to company building within months. His current company, Atoms, is developing artificial intelligence and specialized robotics for industries including food, mining and transportation. Kalanick describes his role as “problem solver in chief,” focusing on the most consequential problems that are not already being solved and pursuing what he considers his broader calling: digitizing the physical world. Show notes: https://www.davidsenra.com/episode/travis-kalanick Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra Deel: https://deel.com/senra Chapters (00:00:00) Building Atoms & the Meta Problem of Management (00:03:51) The Appeal of Impossible Problems: Starting Over in China (00:12:19) Uber vs. Didi: Copycats, Hypergrowth & China's Rules (00:21:02) How Network Effects Become an Efficiency Fortress (00:31:48) Capitalism vs. the Taxi Cartel (00:44:05) The China War Goes Global & the Entrepreneur's Capacity for Pain (00:54:04) Life After Uber: Lawfare, Media Narratives & Reputation (00:58:21) What Founders Get Wrong About Venture Capital (01:08:35) The Fundraising Playbook: QED Storytelling & a Five-Room Auction (01:18:38) The Uber Coup, Radical Accountability & Outgrowing Fear (01:26:42) Why Specialized Robots Beat Humanoids at Industrial Scale (01:31:30) Finding Your Sport: Food, Mining & the Physical AI Stack (01:40:14) How to Build Many Companies Inside One Company (01:46:33) Entropy, Civilization & the Meaning of Progress Learn more about your ad choices. Visit megaphone.fm/adchoices

Lulu Cheng Meservey is the founder of Rostra and one of the world's most trusted communication strategists, supporting companies such as Anduril, Shopify, Cognition, and Coinbase. In 2016, she co-founded TrailRunner International with Jim Wilkinson, who had just run corporate affairs for Alibaba's record IPO. She had never done comms in her life. One of her first clients was Anduril, in the company's first year, when Palmer Luckey had just been pushed out of Facebook, and no reporter would give him a fair hearing. So they stopped asking. They went to Quantico, to Camp Pendleton, to the CIA, and showed people the technology directly. She left to run communications at Substack, then joined the board of Activision Blizzard—and in October 2022 stepped off the board and into the company as chief communications officer. Microsoft's $69 billion acquisition was under attack from the FTC. She fought back in public, under her own name, which almost no executive in a deal that size is willing to do. It closed in October 2023. In March 2024, she started her own firm, Rostra, and published Go Direct: The Manifesto. The first project out the door was Cognition's launch of Devin, the first AI software engineer. Shopify put her on its board that June. In December 2025, she raised a $40 million fund to back founders she believes in. She takes about a dozen clients at a time and has a waiting list of hundreds. She named the firm after the Rostra, the speaker's platform in Rome, where a man could climb up while the city believed one thing and step down after it believed another. Show notes: https://www.davidsenra.com/episode/lulu-cheng-meservey Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra Chapters (00:00:00) From China to America (00:02:08) Learning to Read the Room (00:06:18) Building a Movement (00:07:30) Learning Comms by Doing (00:10:50) Anduril as an Insurgent (00:15:07) The Power of a Manifesto (00:18:47) Go Direct (00:26:45) Conviction Over Charisma (00:31:30) Why Rostra Exists (00:33:23) How AI Leaders Lose Trust (00:40:40) Tell a Better Story (00:47:55) Do Things That Can't Be Faked (00:50:55) The Return to Beauty (00:57:11) Originality Over Templates (01:04:02) Do What Only You Can Do (01:07:14) The Jetsons Rule (01:10:41) Trust Yourself (01:12:29) Why Humans Crave Stories Learn more about your ad choices. Visit megaphone.fm/adchoices

Michael Ovitz⁠ is the co-founder of Creative Artists Agency (CAA), one of the most powerful and influential talent agencies in Hollywood history, built on a revolutionary approach to representation that fundamentally transformed the entertainment industry. He is an entertainment executive and dealmaker widely regarded as one of the most formidable operators in Hollywood. During his time leading CAA, Ovitz represented virtually every major star, including Tom Cruise, Robert De Niro, Meryl Streep, Steven Spielberg, David Letterman, Barbra Streisand and many more. Starting as a mailroom trainee in the 1960s and reshaping the power dynamics of the entire industry by the 1980s, he became known for his relentless strategic thinking, his creation of the "packaging" model that bundled talent for studios, and his ability to orchestrate deals of unprecedented scale and complexity. He built a reputation in entertainment circles through his fierce intelligence, relentless work ethic and his ability to build CAA into what many called "the most powerful company in Hollywood." His major accomplishments include co-founding CAA in 1975 in an audacious break from the establishment, pioneering the packaging system that gave agents unprecedented leverage over studios, orchestrating landmark deals including the sale of Columbia Pictures to Sony, serving as President of The Walt Disney Company and building CAA into a multi-billion dollar enterprise that expanded far beyond traditional talent representation into sports, consulting and global entertainment infrastructure. This is Michael's second time on the podcast. Watch the first episode. Show notes: https://www.davidsenra.com/episode/michael-ovitz-2 Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra Chapters (00:00:00) Why Michael Ovitz Is Busier Than Ever (00:04:27) Why This Era Is More Exciting Than Hollywood's Golden Age (00:08:45) The Fundamentals of Building Enduring Businesses (00:12:06) How Ovitz Chooses What Deserves His Time (00:14:28) Why Ovitz Refuses to Be Typecast (00:19:43) Japan, Trust & Playing the Long Game (00:20:44) Phil Knight, Nike & the College Football Playoff (00:25:59) Competition, Work Ethic & Winning Without Ego (00:31:33) How Ovitz Outworked 200 Rival Agencies (00:37:51) Protecting the Vision: Scorsese, Rain Man & Great Founders (00:40:37) Josh Kushner & Guarding the Company's Soul (00:43:47) Steve Jobs, Pixar & Building a Culture of Ideas (00:47:20) "He Won, We Lost. Next Case." (00:49:21) Bill Ackman, Universal Music Group & the Future of Music (00:53:08) AI, Music & the Future of Entertainment (00:59:13) Jurassic Park, Spielberg & Using New Technology Well (01:01:10) Why Great Creators Study the Past Learn more about your ad choices. Visit megaphone.fm/adchoices

Micky Malka is the founder of Ribbit Capital and helped create Node, which he describes as the first digital art studio designed for digital artists. He calls himself “an entrepreneur at heart and an investor by design”—a deliberately broad description that allows him to resist labels, which is precisely the point. The one label he wants on his tombstone: “He was a rebel.” In his mid-20s, Malka and his partners put all the proceeds from their first dot-com exit into starting Lemon Bank in Brazil. He says they nearly lost everything when the economy failed to take off. At its peak Lemon Bank operated roughly 7,000 locations and served 50 million customers while targeting Brazil’s large unbanked population. He later sold it to Brazil’s largest bank. Years later, after meeting Walmart CEO Doug McMillon in 2019, Malka proposed that Walmart and Ribbit build a better financial-services business together. That effort became OnePay, which now provides payments, debit, credit and lending products across Walmart’s ecosystem. At Ribbit, decisions are made as a group, no single partner is assigned to a company, and the team shares calendars, inboxes and emails. Malka confirms that Ribbit is his sixth company and says he intends to keep building it indefinitely. As he puts it, “The best entrepreneurs never have to sell their company.” Show notes: https://www.davidsenra.com/episode/micky-malka Made possible by Ramp: https://ramp.com Deel: https://deel.com/senra AppLovin: https://applovin.com/senra Chapters (00:00:00) Why Micky Malka Refuses to Be Labeled (00:03:00) Writing Your Way to Conviction (00:05:41) Buying Berkshire at 13 and Learning Buffett's Operating System (00:11:48) Token Factories, AI Bankers, and the Future of Money (00:18:38) The Infinite Game: Why It's Better to Be Behind (00:22:09) Gen Z Founders and the Chaordic Company (00:29:00) Why Young Founders Want to Build Atoms, Not Just Bits (00:34:29) Bringing Beauty and Taste Back to Technology (00:36:56) Revolut, Founder DNA, and Earning Deep Trust (00:45:54) Building OnePay With Walmart (00:50:53) From Lemon Bank to OnePay: A 20-Year Idea (00:56:00) Compounding Trust and Protecting Your Reputation (01:00:30) Node and the Rebel Case for Digital Art (01:07:34) What It Means to Live as a Rebel (01:10:50) Why Ribbit Is Built Like a Startup (01:14:41) Charlie Munger and the Power of Time Learn more about your ad choices. Visit megaphone.fm/adchoices

David Heinemeier Hansson (DHH) is the creator of Ruby on Rails and the co-founder of 37signals, the company behind Basecamp, HEY, and ONCE. He has spent 25 years building a software business around one condition: no one gets to tell him what to do. Jason Fried hired him as a contractor out of Copenhagen for $15 an hour. He built the first version of Basecamp with just 10 hours a week — 380 hours in total — and still credits the shortage of time for how good it turned out. He does not trust himself with unlimited resources. Nobody should, he argues. Give a team too much money and too many people and it will build a blob. Forty-some venture firms came calling in 2005. The only investor 37signals ever said yes to was Jeff Bezos, who accepted a term sheet priced so absurdly high they were certain he would walk. They have been sending him dividend checks ever since. Basecamp has been rewritten three times, and the original 2004 version — discontinued in 2010 — still runs and still makes millions in profit. His marketing strategy, borrowed from Kathy Sierra, hasn't changed in two decades: you can't outspend the giants, but you can out-teach them. His product test hasn't either. He builds the thing he wants for himself, and once he'd rather use it than anything else available, he assumes he isn't alone. That's how Ruby on Rails started. It's how Omarchy started too — the Linux distribution he’s spent thousands of hours making and gives away. No investors. No board. And now, with Omarchy, no customers. He calls that last step a retirement from capitalism: still making things, still sharing them, with nobody holding a claim on his time. Show notes: https://www.davidsenra.com/episode/david-heinemeier-hansson Made possible by Ramp: https://ramp.com AppLovin: https://applovin.com/senra HubSpot: https://hubspot.com/startups Deel: https://deel.com/senra Chapters (00:00:00) Cutting Rework From 50,000 Words To 25,000 (00:02:54) Basecamp Was Built In 380 Hours (00:06:46) Unlimited Resources Build A Blob (00:10:22) Terminator Beats Avatar By A 1000x (00:15:24) The Printer DHH Never Wants To Upgrade (00:17:31) Millions In Profit From 16 Year-Old Software (00:20:10) The Beauty Of A Finished Product (00:22:54) I Would Quit Before Working In An Office (00:25:41) Four Uninterrupted Hours Or The Day Is Lost (00:31:21) Tobi Lütke Saw The AI Future First (00:38:51) Apple Pissed Him Off Enough To Switch (00:42:47) The 19 Year-Old Who Beat Apple (00:47:16) If Nobody Else Will Build It, I Will (00:52:02) The Need For Control, Independence, And Freedom (00:53:44) Chef's Choice, Not A Construction-Kit Burger (00:56:50) A New Computer Ready In 2 Minutes (01:00:33) A Cheaper Mac Will Never Win (01:02:27) The Best Ideas Sound Stupid At First (01:03:47) Out-Teach Your Competition (01:06:57) The Algorithms Broke Reciprocity (01:10:53) No Investors Is Freedom. No Customers Is Transcendence. (01:13:25) No One Gets To Tell Me What To Do (01:16:49) Your Moral Obligation To Buy A Ferrari (01:23:19) Costs Are The Only Thing You Control (01:26:49) Bezos Paid For The Promise (01:30:17) The Confidence To Say No To Everyone (01:32:59) The Day A Third Of The Company Left (01:36:49) Marc Andreessen Came To Help Learn more about your ad choices. Visit megaphone.fm/adchoices