On Building Media Companies with Dan Shipper (Every) x Alex Konrad (Upstarts)

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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 Media, 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.

In this episode of The General Podcast, 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 advantage 2. How thinking like a product person (and not just a writer) shapes everything they publish 3. The surprisingly tactical ways they protect time for original thinking 4. Why Upstarts and Every both resisted the pressure to “build the platform” too soon 5. How Every runs multiple AI products and a daily newsletter with only 15 people 6. Why they both believe your business model is a creative decision 7. Their thinking around independent journalism as a “tech-enabled service,” not content 8. How AI tools like Claude, Cora, and ChatGPT actually fit into their creative process 9. How to avoid burnout when your business is also your identity 10. How to stay joyful and experimental when everyone else is optimizing

Where to find Dan: Newsletter: every.to X: @danshipper

Where to find Alex: Newsletter: upstartsmedia.com X: @alexrkonrad

Referenced in this episode:

• MrBeast

• The Pragmatic Engineer

• Stratechery by Ben Thompson

• Lenny’s Newsletter

• Tom Brady quote: “Winners focus on winning. Losers focus on winners.”

• Acquired Podcast

• Claude

• ChatGPT

• War and Peace by Leo Tolstoy

• The writer Maggie Nelson

• Spiral by Every

• Cora by Every

• Think Week (Bill Gates’s famous retreat)

• Documentary: WeWork: Or the Making and Breaking of a $47 Billion Unicorn