Why fewer meetings lead to better products with Steve Schoeffel (Whimsical)

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: https://www.linkedin.com/in/steveschoeffel — Where to find Jack Hannah:   • LinkedIn: ⁠⁠⁠⁠⁠⁠⁠https://www.linkedin.com/in/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 State of Async (formerly The Whimsical Way): https://whimsical.com/blog/state-of-async-2026 • 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