Dan Shipper (Every) x Alex Konrad (Upstarts) on building media companies

Dan Shipper is the co-founder and CEO of Every, a media company built around writing, software, and AI. With a tiny team, they put out a daily newsletter, build products, and run a consulting arm, all while staying weird and experimental. Dan’s one of the most thoughtful writers on how AI is reshaping creativity, business, and what it means to build.Alex Konrad is the founder of Upstarts, a newsletter about the next breakout companies before they break out. He spent over a decade at Forbes, where he wrote 15+ cover stories, co-created the Cloud 100 list, and led Midas List coverage of the top VCs in the world. Together, they discuss and debate building sustainable media businesses today, using AI to amplify creativity, and why legacy playbooks no longer apply.In this conversation, you’ll learn:1. Why being weird is often a competitive advantage2. How thinking like a product person (and not just a writer) shapes everything they publish3. The surprisingly tactical ways they protect time for original thinking4. Why Upstarts and Every both resisted the pressure to “build the platform” too soon5. How Every runs multiple AI products and a daily newsletter with only 15 people6. Why they both believe your business model is a creative decision7. Their thinking around independent journalism as a “tech-enabled service,” not content8. How AI tools like Claude, Cora, and ChatGPT actually fit into their creative process9. How to avoid burnout when your business is also your identity10. How to stay joyful and experimental when everyone else is optimizingWhere to find Dan:Newsletter: every.toX: @danshipperWhere to find Alex:Newsletter: https://www.upstartsmedia.comX: @alexrkonradWhere to find TheGP:Newsletter:  https://thegeneralpartnership.substack.com/X: @thegpReferenced in this episode:MrBeast: https://www.youtube.com/@MrBeastThe Pragmatic Engineer: https://www.pragmaticengineer.comStratechery by Ben Thompson: https://stratechery.com/Lenny’s Newsletter: https://www.lennysnewsletter.com/Tom Brady quote: “Winners focus on winning. Losers focus on winners.”Acquired Podcast: https://www.acquired.fm/Claude: https://claude.aiChatGPT: https://chatgpt.com War and Peace by Leo TolstoyThe writer Maggie NelsonSpiral by Every: https://spiral.computerCora by Every: https://cora.computerThink Week (Bill Gates’s famous retreat)Documentary: WeWork: Or the Making and Breaking of a $47 Billion Unicorn