SC 018 — Getting Weird with Squarely

Summary

The origin story of the Squarely case study series. Facing a three-way tension — developing craft, empowering others, and driving business growth — the founder applies a “do the weirdest thing that feels right” decision framework. Rejects generalizing lessons (textbook-like), fictional scenarios (too much setup), and finding a willing real business (too hard). Instead, launches a longitudinal case study on his father’s puzzle company, Squarely Puzzles.

Acknowledges this is illogical — no revenue expectations, unfavorable unit economics — but argues the advantages are real: full transparency permission, real ecommerce challenges, and family benefit.

Curated section highlights the open-source data ecosystem’s democratization: Hamilton’s 7-powers, Wes McKinney on composable systems, and Pedram’s Open Data Stack demo.

Key Arguments

• “Do the weirdest thing that feels right” as a legitimate decision framework when options are equally reasonable
• Real > fictional for case studies — messiness is the point
• Open-source ecosystem is genuinely expanding access for emerging practitioners
• The best content comes from authentic situations, not manufactured ones

Writing Style Notes

This is peak founder voice — vulnerable about the illogic of the choice, honest about motivations, excited about the open-source ecosystem. The “getting weird” framing is playful but the reasoning is sharp.

Connections

• index — launches the Squarely case study arc
• index — meta-writing about the newsletter’s direction