Entrepreneurship & Startups
Founders, venture capital, company-building, and the strategic work of turning ideas into durable organizations.
- #10436,000 Companies, One Metric: What DPI Did to Private EquityStewart SquaredAugust 27, 2026
- #561The Internet Was Democratic By Design. AI Was Built to Concentrate Power.July 13, 2026
- #560Can AI Build a Better Civilization?July 10, 2026
- #93Too Big to Question: SpaceX, Wall Street, and the End of AccountabilityStewart SquaredJune 11, 2026
- #88Conspiracy Factist vs. Practical Capitalist: The Alsop DebateStewart SquaredMay 7, 2026
- #85The Conspiracy Theory That Isn't: When Silicon Valley Quietly Changes the DealStewart SquaredApril 16, 2026
- #536From Filament to Agents: The Tools Keep Getting Cheaper and the Judgment Keeps Getting ScarcerMarch 9, 2026
- #78The Vibe Coding Takeover: How Bot Swarms Are Turning SaaS Into an Endangered SpeciesStewart SquaredFebruary 26, 2026
- #530The Hidden Architecture: Why Your Startup Needs an Ontology (Before It's Too Late)February 9, 2026
- #527Breaking the FinTech Echo Chamber: Tommy Yu's Behavioral Finance Operating SystemJanuary 30, 2026
- #66The Randomness Engine: Why Silicon Valley Can't Be Cloned (And Why That Matters for AI)Stewart SquaredDecember 4, 2025
- #65From Strawberries to Silicon Valley: The Origin Story of Atari’s MindsetStewart SquaredNovember 27, 2025
- #494Recursive Loops, Cult Startups, and the Mirage of AIOctober 3, 2025
- #458How a Tiny Irish Startup Beat Amazon to the AirMay 6, 2025
- #32Startups, Deadlines, and Drift: The Venture Logic Behind Modern NewsroomsStewart SquaredApril 10, 2025
- #29Bridging the Physical and Digital: Investing in the Next Big ShiftStewart SquaredMarch 20, 2025
- #442Satellites, Strategy, and Staying Profitable: A No-BS Look at Space TechMarch 10, 2025
- #26Steve Case on the Internet’s Wild Ride and What’s NextStewart SquaredFebruary 27, 2025
- #437From Garage Sales to Multi-Million Dollar E-Commerce EmpiresFebruary 21, 2025
- #18Why Innovation Needs Leadership: Stories from Silicon Valley and BeyondStewart SquaredNovember 28, 2024
- #5Silicon Valley's Dark Horse: Oracle’s Past, Present, and FutureStewart SquaredAugust 29, 2024
- #4Building Giants and Guarding Integrity: Lessons from the Tech TrenchesStewart SquaredAugust 22, 2024
- #383From Founder-Led Sales to Team Excellence: A Blueprint for Startup SuccessAugust 16, 2024
- —Navigating the Digital Revolution with Steve CaseJune 28, 2024
- —Silicon Valley y Buenos Aires: Dos Mundos TecnológicosCrazy Wisdom en Español26 de junio de 2024
- —Explorando Nuevas Fronteras en la Ciencia y la Tecnología con German JuradoCrazy Wisdom en Español29 de mayo de 2024
- —Byte-Sized Brilliance: Crafting the Future with Creativity and CodeFebruary 12, 2024
- —The Argentine Advantage: Thriving in a World of UncertaintyNovember 21, 2023
- —Business Beyond the Numbers: A Conversation with Maranda DziekonskiNovember 13, 2023
- —Deep Tech Renaissance: John Lee on Emerging Technologies and Capital AllocationOctober 23, 2023
- —The Changing Face of Entrepreneurship in Latin America: A Conversation with Ivan MontoyaAugust 14, 2023
- —What makes some people contrarian? - Enzo CavalieAugust 21, 2020
- —What is the lifespan of the most important technologies? Svilen Rangelov: CEO of DronamicsFebruary 28, 2020
- —What is the relationship between creativity and venture capital? - Leo Polovets: Susa VenturesFebruary 26, 2020
- —What is it like to succeed when 290 investors tell you no? - Benjamin Fernandes: CEO of NALAJanuary 29, 2020
- —What is the hallmark of true mastery? - Jacob Cole: CEO of IdeaFlowJanuary 27, 2020
- —What does it mean to commit to something challenging? Dulma Altan - CEO of MakelaneJanuary 16, 2020
- —Singapore as a technology hub - Ben ReinhardtJanuary 15, 2020
- —What do you learn from starting a company in Mexico and then selling it in SF? - Domingo GuerraJanuary 14, 2020
- —What is the relationship between money and entrepreneurship? Marco Fuxa: Investor and EntrepreneurDecember 10, 2019
- —How to think about investing in remote companies? Jeff Morris Jr: Growth at Lambda SchoolNovember 18, 2019
- —What is the global playing field for startups? - Boris Wertz (Version One VC)November 11, 2019
- —What does it mean to innovate? Wiza Jalakasi: Head of Global BD and StrategyNovember 8, 2019
- —How has the global startup ecosystem changed? Torsten Kolind: CEO & Cofounder YouNoodleNovember 6, 2019
- —What is the difference between a pitch and telling a story? - John Fein: Managing Partner Firebrand VenturesOctober 25, 2019
- —How do you tell your investors you have cancer? - Michael FitzGerald (CEO of Submittable)October 8, 2019
- —How do you take a company from idea to IPO? - Joe AlsopSeptember 20, 2019
- —Steve Schlafman: Venture Capital, Chronic Pain, CreativityAugust 26, 2019
- —Maia Bittner: Startups, Business and Life in SFAugust 23, 2019
- —Special Interview Series: Investing in the Ocean Technology SectorAugust 21, 2019
- —Natalie Nagele: CEO of WildbitAugust 16, 2019
- —Online course for startup founders to raise money for a distributed teamJuly 22, 2019
- —Ryan Caldbeck - The Other Side of EntrepreneurshipJuly 22, 2019
- —David E. Weekly: CEO and Cofounder of MedcorderJune 28, 2019
- —Brett J Fox - Lessons from a True OperatorJune 3, 2019
- —Marc Bitanga - What is marketing and how does it work?May 31, 2019
- —Sahil Lavingia - CEO of Gumroad: What happens when you move from SF to Provo, Utah?May 27, 2019
- —Jude Gomila: CEO of Golden - Polymaths at workMay 24, 2019
- —What happens when you move West?May 6, 2019
- —How to Use Stress as an Entrepreneur (feat. Mike Maples Jr.)November 19, 2018
- —What is the difference between stress and anxiety?October 8, 2018
- —Can you build a company with minimal stress? Andy Alsop - CEO of The ReceptionistAugust 27, 2018
- —How do you deal with the anxiety that comes from being on stage? - Joey Greiner: CEO of WoojoJuly 16, 2018
- —How does meditation help you to find balance while creating something new? Anders Jones - CEO of Facet WealthJuly 9, 2018
- —How do you stay calm when everything around you is telling you to freak out? - Ruben Harris: Founder of Breaking Into StartupsJuly 2, 2018
- —Can you view stress as a motivator instead of as a disease? - Keith Rabois of Founders FundMay 22, 2018
- —Does following your bliss lead to more success in work and life? - Bill Tai of BitfuryMay 8, 2018