Imagine trying to sell hot dogs in a park where everyone knows the recipe and can make their own hot dogs. How do you survive? You sell premium buns with artisanal mustard. Or you offer a "hot dog as a service" (aka, delivery). Or you make it really annoying to cook hot dogs at scale without your industrial-grade hot dog infrastructure. This is Commercial Open Source in a nutshell, and your license is basically deciding which condiments you're allowed to charge for. Choose wrong, and you're the person handing out free samples while Costco builds a hot dog empire using your exact recipe. Choose right, and you've got defensible margins and a path to exit. The License Determines the Architecture of the Business In the world of proprietary software, the business model is straightforward: you build a fortress, and you charge admission. But in Commercial Open Source (COSS), you are building a public park and trying to sell hot dogs from a cart. Your choice of license plays an essential role in the success of a COSS business, yet many technical founders select an open source license with the same casual intuition they use to pick a t-shirt color. They choose MIT because it feels “free,” or AGPL because they want to “stick it to the man,” or Apache 2.0 because “that’s what Kubernetes used.” This is a category error of the highest order. Your license is not merely a legal document intended to satisfy a compliance officer; it is the structural engineering that bridges that gap. It defines the physics of your unit economics, the coefficient of friction in your sales cycle, and the height of your defensive walls. Unless you have a licensing strategy, you are essentially building a skyscraper without a blueprint. To correctly architect your strategy, you must map your business across three dimensions of tension: how you make money, how you distribute value, and how you defend your margins. The disconnect between value creation (which is public) and value capture (which is private) is the fundamental tension of the model. Dimension 1: Monetization The first question is not “What is open,” but “What is for sale?” Consider the support and services model, often romanticized because of Red Hat. The architecture here is usually permissive (Apache 2.0 or MIT). The theory is that you remove all friction to drive ubiquity, effectively lowering your Customer Acquisition Cost (CAC) to near zero, and then monetize a fraction of that user base through SLAs and indemnity. The brutal reality, however, is that this is a service business masquerading as a product company. Service margins are often 30% to 50% compared to the 80% to 90% margins of pure software. Unless you possess the operational excellence of a Red Hat, a company that scaled by being the only adult in the room during the chaotic early days of Linux, you will likely find yourself running a low-margin consultancy that cannot scale venture returns. A far more robust architecture for the modern venture-backed startup is the proprietary feature layer, or “Open Core.” Here, the license acts as a scalpel, bifurcating your product into two distinct value streams. You license the core engine, the thing that developers need to adopt, permissively (e.g., Apache 2.0). This drives the standard. But you retain enterprise features, such as governance, SSO, audit logs, and multi-region clustering under a proprietary commercial license. This works because you are selling high-margin software to the enterprise buyer who cares about control while giving away the commodity utility to the developer who cares about speed. Then there is the aggressive stance: Dual Licensing. This is the “Quid Pro Quo” architecture used famously by MySQL. You release your software under a strong copyleft license like GPL. This acts as a viral agent; anyone who touches it must open their own code. For the hobbyist or the open ecosystem, Dual Licensing is fine. But for the OEM or the proprietary vendor who wants to embed your database into their closed-source appliance, the GPL is a poison pill. To swallow it, they must buy a commercial license from you. This architecture transforms your license into a sales forcing function. It is powerful, but it comes with a strict operational requirement: you must own 100% of the copyright. If you accept even a single external contribution without a rigorous copyright assignment, you may risk losing the right to sell the commercial exception. Dimension 2: Distribution In COSS, the community is your marketing engine, your R&D lab, and your distribution channel. Your license determines the velocity of this engine. If your strategy relies on developer velocity, if you need to become the de facto standard protocol, language, or library, then friction is your enemy. Permissive licenses like MIT or Apache 2.0 act as a lubricant. They tell the developer at a Fortune 500 bank or a scrappy startup that they can pull your library into their stack without asking a lawyer for permission. The data is clear: permissive projects see 3x to 5x higher contribution rates and integration velocity because they remove the fear of legal entanglement. However, friction works both ways. While copyleft licenses (AGPL/GPL) slow enterprise adoption, they serve as a binding agent for the end-user community. Because a developer cannot simply fork an AGPL project and turn it into a proprietary product, they are more likely to contribute back to the upstream repo. The community becomes “stickier” because everyone is bound by the same reciprocal rules. But you must be realistic about the enterprise immune system. A significant majority of Fortune 500 legal departments (roughly 73% by recent counts) have standing policies restricting or banning AGPL software. If you choose a copyleft license to bring coherence to your community, you must accept that you are introducing a massive point of friction into your sales cycle. You will need a more patient sales team, longer cycle times, and a strategy to navigate procurement roadblocks. Dimension 3: The Competitive Moat The final dimension is defensibility. What stops a competitor (specifically, a trillion-dollar cloud provider) from taking your innovation and selling it as their own? This is the “free rider” problem. If you choose a permissive license to maximize adoption, you implicitly accept that AWS or Azure can take your code, wrap it in a managed service, and sell it without paying you a dime. You are betting that your brand gravity and the “network effect” of your ecosystem are strong enough moats to withstand commoditization. If that bet feels too rich for your blood, you look toward IP containment. Copyleft licenses attempt to build a legal moat by forcing competitors to share their modifications. But in the cloud era, this wall has cracks. The “SaaS Loophole” often allows cloud providers to run AGPL software as a service without triggering distribution clauses. This led to the invention of the hosted service defense, which uses licenses like the SSPL (Server Side Public License). These are not open source in the strict OSI definition; they are commercial weapons. They explicitly forbid a cloud provider from offering the software as a managed service. This is the nuclear option. It effectively stops AWS from eating your lunch, but the fallout can be severe. It can fracture your community (often resulting in a community-led fork) and alienate the open source purists. It is a moat, yes, but it often encircles a lonely castle. The Founder’s Trilemma The brutal truth of this framework is that you cannot optimize for everything. You are facing a trilemma. You cannot simultaneously maximize adoption velocity (which requires permissive licensing), IP defensibility (which requires restrictive licensing), and monetization flexibility (which requires commercial rights). Every choice is a trade-off. If you optimize for adoption, you expose yourself to cloud competition. If you optimize for defense, you slow down enterprise sales. If you optimize for monetization, you risk alienating your contributors.
