No Meetings, No Deadlines, No Full-Time Employees

But the deal we already had in place was better for what our people prioritize: freedom over growth, sustainability over speed, life over work.

In his words, “most entrepreneurs have two options: work a full-time job and hustle nights/weekends, or leave your job and risk everything to start the company. Gumroad provided a third way: I could contract 20-35 hours a week, and for a couple days a week, incubate ideas and work on my next thing.”

But we can compete–and win–on flexibility.

There are no retreats planned, and no social channels in Slack. There are limited opportunities for growth. And we can’t compete with the comp packages that big tech companies can provide.

This way of working isn’t for everyone.

When someone new joins the company, they do what everyone else does: go into our Notion queue, pick a task, and get to work, asking for clarification when needed.

Everyone writes well, and writes a lot.

Instead of having meetings, people “talk” to each other via GitHub, Notion, and (occasionally) Slack, expecting responses within 24 hours. Because there are no standups or “syncs” and some projects can involve expensive feedback loops to collaborate, working this way requires clear and thoughtful communication.

Today, working at Gumroad resembles working on an open source project like Rails. Except it’s neither open source, nor unpaid.