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...
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.
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Where to find Steve Schoeffel:
• LinkedIn: https://www.linkedin.com/in/steveschoeffel
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Where to find Jack Hannah:
• LinkedIn: https://www.linkedin.com/in/jack-hannah/
• Website: https://tuple.app/
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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
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Referenced:
• Whimsical: https://whimsical.com
• The Whimsical Way: https://whimsical.com/whimsical-way
• Kaspars Dancis on LinkedIn: https://www.linkedin.com/in/kasparsd
• How async work inspires craftsmanship: https://whimsical.com/blog/how-async-work-inspires-craftsmanship
• Development cycles, process, and tooling: https://tuple.app/distributed/head-of-engineering-at-sublime-security-on-development-cycles-process-and-tooling-with-sumeet-jain
• Craftsmanship, the heart of Whimsical: https://whimsical.com/blog/craftsmanship-the-heart-of-whimsical
• Frank Slootman on LinkedIn: https://www.linkedin.com/in/frankslootman
• Shapeup: https://basecamp.com/shapeup
