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What does craftsmanship look like in an async-first, remote company? In this episode of Distributed, host Jack Hannah sits down with Steve Schoeffel, co-founder of Whimsical, to talk about async-first work, craftsmanship, and the tradeoffs of running a fully remote company. Steve shares how Whimsical creates momentum without constant meetings, why quality lives in the details, and how async-first work shapes both the product and the company culture. Steve also reflects on the harder, more personal side of the work. He talks candidly about co-founder misalignment, the strain of leadership during periods of uncertainty, and what it’s been like to learn to hold work more loosely over time. They also dig into the return-to-office push and why Steve remains convinced that remote work, done well, is worth fighting for. Where to find Steve Schoeffel: • LinkedIn: / steveschoeffel Where to find Jack Hannah: • LinkedIn: / jack-hannah • Website: https://tuple.app/ Timestamps: (00:00) Intro (01:02) An overview of Whimsical (02:02) The size of Whimsical’s team and how it operates across time zones (03:08) What the Whimsical Way is and how it shows up in practice (04:58) Why Whimsical is async-first and what that looks like in practice (10:49) How Whimsical maintains energy and connection in async work (13:59) Craftsmanship as a core value at Whimsical (18:21) How Whimsical pursues “insanely great” work (24:14) What’s been hardest about running a remote company (28:24) How Steve realized he and his co-founder were misaligned (32:08) How Steve is learning to detach from work and care for himself (36:32) Why Steve remains pro–remote work amid big tech’s return-to-office push Referenced: • Whimsical: https://whimsical.com • The Whimsical Way: https://whimsical.com/whimsical-way • Kaspars Dancis on LinkedIn: / kasparsd • How async work inspires craftsmanship: https://whimsical.com/blog/how-async-... • Development cycles, process, and tooling: https://tuple.app/distributed/head-of... • Craftsmanship, the heart of Whimsical: https://whimsical.com/blog/craftsmans... • Frank Slootman on LinkedIn: / frankslootman • Shapeup: https://basecamp.com/shapeup