Mixed Signals from Semafor Media Blackbird Spyplane’s Jonah Weiner on Substack, resisting selling out, and Obama’s pants legacy
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Oct 3, 2025 Join Jonah Weiner, co-founder of the Blackbird Spyplane newsletter and a seasoned magazine journalist, as he delves into the evolution of his acclaimed style and culture platform. He shares insights on resisting affiliate links to maintain reader trust and discusses how his newsletter changed his marriage dynamics. Jonah explores fashion trends, highlighting Obama's 'dad pants' as a cultural touchstone. He reflects on the future of writing, balancing commerce with authenticity, and maintaining a sustainable approach in the ever-evolving media landscape.
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Focus On Makers And Cherished Objects
- Blackbird Spyplane focuses on clothes, makers, and the talismanic value of physical objects.
- Jonah centers on small producers and personal relationships to cherished items rather than pure shopping lists.
Early Slang Voice As A Creative Switch
- Jonah describes how his early newsletter voice was slang-heavy and intentionally different from magazine prose.
- He used that persona to signal a switch from Times Magazine features to a looser, in-group newsletter style.
Tone Evolves With Story Length
- Jonah explains he toned down the newsletter voice after writing longer reported pieces.
- He realized investigative or long-form work required subtler diction to fit the subject matter.