April 9, 2025

Sahil Lavingia's future of work experiments

Sahil Lavingia, the founder of Gumroad and Antiwork, is living two years in the future.

He's testing a lot of compelling ideas, inspired by his experience "failing to build a billion-dollar company" and his astute observations about the changing nature of software development and work.

Here are a few ideas of his that I find particularly interesting:

Open source bounties: Having open sourced several of Antiwork's projects – including Gumroad and Flexile – the company creates open issues not just for bugs but also for features. They assign bounties to each one, and offer bounties to be paid in equity.

Cybernetic teammates: The AI code agent Devin is responsible for 41% of Antiwork's PRs, and Sahil expects this to grow to 80% by the end of next year.

Royalty-based Funding: We've previously thought about how traditional venture funding isn't a good fit for AI-enabled solo founders, because such founders don't necessarily need to aim for a massive exit.

  • Instead, an initial allotment can help talented indie hackers work on new projects full-time.
  • Their companies could become profitable more quickly than startups with many employees because of the relatively low overhead.
  • The funder could claim a share of the company's future profits, which aligns incentives between the funder and the founder.

Flexible work: Antiwork is agnostic to working location, schedule, and even hours. They've built Flexible to help other companies employ talent with more flexible arrangements, including packages of salary, equity, and dividends.

Transparency: Sahil writes in a lowkey, casual way that is refreshing. For example, in the blog post above, he says:

I think our equity model is cool. My mom thinks it is confusing. Others, like my wife, see anything that is not a direct cash payment as a Ponzi scheme. This is my best attempt at explaining Gumroad's approach to equity, and the history behind it, so you can decide for yourself.

He also conducts quarterly board meetings in public where he shares company financials and usage data.

No Meetings, No Deadlines: This is maybe my favorite thing. Meetings suck. Deadlines are recipes for disaster. Nonetheless, meetings and deadlines are endemic plagues at software firms.

Writing and videos (like Looms) are vastly better than meetings. Deadlines are usually arbitrary; users don't care what date a feature is released, just that it's good.

We'll see how Antiwork progresses, but I'm excited to see someone experimenting so widely and openly.