How not to do Open Source Licensing, with Trigger.dev founders Matt Aitken and Eric Allam
Trigger.dev founders Matt Aitken and Eric Allam explain what permissive, copyleft and fair-source licenses actually do—and why founders should choose a familiar license by starting with the risk they need it to address.
Open-source licensing is easy to treat as a badge and difficult to reason about as a business decision. Trigger.dev founders Matt Aitken and Eric Allam have worked through that decision across JSON Hero and Trigger.dev, whose public repository uses Apache-2.0.
This conversation is a practical map of the tradeoffs: what MIT and Apache permit, when copyleft obligations apply, what the Functional Source License changes, and why a successful open-source company still has to win on product and service.
The Q&A below is experimental — extracted from the episode transcript with AI. If you spot a mistake, let us know at jack@scalingdevtools.com.
What should a founder decide before choosing a license?
Begin with the behavior the license needs to prevent. One concern is a cloud provider or direct competitor repackaging the product; another is a large company self-hosting it indefinitely without becoming a customer. Those are different risks and may call for different restrictions. The product also matters: if it is difficult or mission-critical to operate, enterprises may prefer to pay the team that understands it even when the code itself is permissively licensed.
Why did Trigger.dev choose Apache-2.0?
The team wanted the product to be genuinely self-hostable and deployable into an enterprise’s own cloud without depending on proprietary infrastructure. Apache-2.0 is permissive, familiar to legal teams and includes explicit patent terms that MIT does not. The same philosophy shapes the architecture: Trigger.dev used ElectricSQL for real-time behavior rather than making the self-hosted product depend on a service available only through one cloud.
What can a permissive license do for distribution?
It lets developers try and adopt the product with very little institutional friction. Self-hosters can become internal advocates, create organic inbound demand and later ask for a commercial relationship once many teams rely on the software. Matt and Eric see the fear of an AWS-scale clone as premature for most startups: reaching the point where a hyperscaler wants to copy the product would itself mean the category had become important.
Why not write a custom open-source license?
Novel wording creates work for every user. Enterprises often have an allowlist of known licenses; anything outside it can trigger a slow legal review or an outright rejection. A custom license may also call itself open source while failing the standard definition. Unless a company has a precise, important protection that established licenses cannot provide, familiarity is a product advantage.
How does Trigger.dev separate open-source and commercial code?
The public Apache-licensed repository contains the core product, including features enterprises need to run it themselves. A separate private codebase operates Trigger.dev Cloud and covers concerns such as autoscaling, billing and the managed service. The intention is not to cripple the self-hosted edition, but to charge for operating the best hosted version and for the organizational value around it.
Does self-hosting undermine the hosted business?
Trigger.dev’s experience suggested the opposite. Growth in self-hosting and cloud usage moved together, and users sometimes moved in either direction as their needs changed. The public product builds trust and adoption; the managed product wins when customers value convenience, support and the team’s ability to operate its own software better than anyone else.
What does copyleft actually mean?
Licenses such as the GPL attach conditions when covered code is distributed as part of a derivative work. Complying may require releasing that work under compatible terms; otherwise the copyright holder can enforce the license. The code is not magically published merely because it was written. Traditional GPL language also left a SaaS gap because running modified software over a network is not the same as distributing it, which the AGPL was designed to address.
Why can copyleft be difficult for a DevTools startup?
The uncertainty can be as damaging as the eventual legal answer. Companies may avoid a dependency when they cannot easily determine whether their own code becomes a derivative work or what they would have to disclose. That makes adoption harder inside enterprises. If copyleft is not directly advancing the project’s mission, Matt and Eric favor a permissive license that removes the ambiguity.
How does the Functional Source License differ?
FSL is a source-available license intended to deter competing commercial use for a rolling two-year period, after which a release converts to an open-source license such as Apache-2.0. That can protect a company while eventually opening the code, but it is not an OSI-approved open-source license during the restricted period. The distinction can confuse users and prevent inclusion in deployment tools whose policies accept only established open-source licenses.
What is the durable open-source business strategy?
Treat the license as the rules of the game, then build the best service within those rules. A company should expect forks and competitors and earn customers through its cloud experience, reputation, pace and support. Relicensing later cannot revoke rights already granted to old versions, so the community may continue them—as happened when Redis code was forked into Valkey. The defensible position is therefore the team and product, not resentment that others used the permissions the company chose.
Links & references
- Trigger.dev ↗
- Eric Allam on X ↗
- Matt Aitken on X ↗
- Apache License 2.0 ↗
- MIT License ↗
- Fair Source ↗
- Valkey ↗
- JSON Hero ↗
- Heather Meeker ↗
- Open Source for Business (Heather Meeker) ↗
- Sentry ↗
- Redis ↗
- ClickHouse ↗
This episode is brought to you by WorkOS.