Distributed.20 Nov 2025

The joy of doing it right: lessons from 50 billion downloads with Jesse Wilson (Cash App, Google)

In this episode of Distributed, host Jack Hannah talks with Jesse Wilson, a longtime open-source contributor and Cash App engineer, whose work underpins much of the Java and Android ecosystem. Jesse shares why some of the most rewarding engineering work comes from doing things the right way, even when it’s the hard way.

Their conversation dives into the story behind Okio, the I/O library for Android, Java, and Kotlin that’s been downloaded >50 billion times, and what it revealed about craftsmanship, risk-taking, and building for the long term. They also unpack how remote teams can bring back the spark of in-person collaboration by pairing more often, embracing small interruptions, and using shared artifacts to stay aligned.

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Where to find Jesse Wilson:

• Mastodon: https://cosocial.ca/@jessewilson

• LinkedIn: https://www.linkedin.com/in/swankjesse

• Blog: https://publicobject.com

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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

(01:28) Why the quick and bad way is never the right choice

(04:07) A story from Okio that shaped Jesse’s engineering philosophy

(06:39) How company culture empowered Jesse to build Okio

(08:46) The challenges of building Okio

(12:40) Why Okio was worth building

(15:08) The value of spontaneous collaboration and why interruptions can be good

(21:10) Handling friction in distributed teams

(27:32) The value of shared responsibilities and scheduled maintenance

(31:05) How Jesse balances meetings with time for flow state

(35:42) How a shared whiteboard or Google Doc keeps meetings on track

(40:52) How shared artifacts guide meetings and make wrap-ups effortless

(43:23) Rapid-fire round

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Referenced:

• Okio: https://square.github.io/okio/

• Writing Code That Lasts Forever: https://publicobject.com/2018/08/28/writing-code-that-lasts-forever

• Todoist: https://www.todoist.com

• inessential by Brent Simmons: https://inessential.com

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