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