So yeh. This is the second post in the There Is No Host series. The first post argued that hosting creates unnecessary friction that hinders WordPress growth.
This post digs into something deeper: open source is fundamentally about freedom, but that freedom isn’t currently delivering competitive advantage. I want to explore how software and freedom are interconnected, how that relationship has evolved, and what strategies might translate freedom into meaningful differentiation.
We don’t make software for free, we make it for freedom.
That’s a compelling brand promise. But who cares about freedom if you’re not making money? And more importantly: how do we make freedom a competitive advantage?
Software Value × Freedom Evolution
I created this chart (inspired by conversations at SXSW 2024) to explore how software value and freedom have evolved:
The chart shows four evolution points in how people access and use software:
- Write your own software (highest freedom, lowest value)
- Software you didn’t write but can run and host yourself (high freedom, moderate value)
- SaaS/managed experiences (low freedom, high value)
- AI-generated/on-the-fly software (lowest freedom, highest value)
Like Software, But Pizza
Here’s a brilliant analogy for these evolution points using pizza:
- Write your own software = Make your own pizza from scratch (grow the wheat, make the cheese)
- Self-hosted open source = Supermarket pizza (pre-made, you bake it at home)
- SaaS platforms = Take-out pizza (someone else makes and delivers it)
- AI-generated = Dine-out pizza, or having a personal pizza chef
Understanding the Axes
Y-axis: Value
For simplicity, consider "Value" as an aggregate of ease of use, profitability, and overall benefit. In pizza terms: tastier, more convenient, faster to obtain.
X-axis: Freedom
Increasing centralization creates power inequality, which equals "inverse freedom." Higher centralization means uniformity and less user control. In pizza terms: eating at a standardized chain where you don’t need to understand how pizza is made.
The Red Line: Value vs Freedom
TL;DR – Freedom and value are inversely correlated in software. If WordPress and WooCommerce stay where they are, they’ll lose users to higher-value solutions. If they chase the red line (SaaS convergence), they compete head-on with better-resourced competition. But there’s a space above the red line that offers potential for differentiation by being "freedom maximalists."
Key Observations:
1. The Schelling Point
The red line represents where most digital solutions converge. It’s thick because different solutions have various characteristics within that space. The further along this trend line, the less freedom and democratization exist.
2. Pressure to Converge
Most users progress along the red line due to competitive market pressure to unlock greater value. Below the red line, there’s pressure to converge toward it—people will seek maximum value even if it means sacrificing some freedom.
3. Why Freedom Gets Squeezed Above the Red Line
Beyond evolution point 2, end users rarely need to understand infrastructure and hosting. Giving too much freedom to customers increases churn risk and relinquishes data/control that competitors use as strategic advantages.
Historically, managed services required hardware, real-world resources, investment, and teams—things capitalism excels at provisioning.
4. Red Ocean vs Blue Ocean
Staying along the red trend line is Red Ocean strategy: competing directly with companies that control every aspect of user experience. As Peter Thiel says, competition is a loser’s game.
The area above the trend line represents Blue Ocean—an opportunity to differentiate in ways others can’t.
5. WordPress & WooCommerce Are Stuck
WordPress and WooCommerce are largely stuck at point 2, with some ventures into point 3. WordPress.com was an early SaaS that drove significant success, but it still struggles with identity: Is it hosting? Or a SaaS? Right now it feels like very opinionated managed hosting with some SaaS-like features.
For this Blue Ocean opportunity to be real, freedom must become (directly or indirectly) a factor people actually care about when making purchasing decisions.
The Evolution of Freedom Online
Online freedom and innovation are both Red Queen situations. Freedom needs to run ever faster to maintain parity with the accretive powers of centralization. Innovation is progressive by definition.
The Historic Epochs of the Internet
Chris Dixon (in Read Write Own) argues that we can consider three epochs:
These three epochs are drastically different in terms of freedoms:
1. Protocol Networks (Read)
Open protocols like TCP/IP, SMTP, FTP. Permissionless and free to use.
2. Corporate Networks (Read-Write)
Permissioned and usually require either payment or data harvesting. These companies can provision and manage infrastructure and databases in ways open protocols historically couldn’t.
Corporate networks have largely eaten protocol networks. Facebook and Google dominate. Most people who want a "pizza" will buy from a supermarket, get takeout, or dine out. What used to be the norm (making your own if you wanted one) has become a luxury.
3. Blockchain Networks (Read-Write-Own)
Permissionless and famously "slow and expensive databases," but they are permissionless databases, and they’re getting faster and cheaper.
How This Changed What Freedom Means
Freedom needs to be important to people for open source’s brand promise to have impact. Currently, it doesn’t matter enough to enough people, enough of the time.
We still have the original digital freedoms:
- We’re free to write our own software
- Host our own email and web servers
- Use permissionless internet protocols
- Make pizza from scratch, growing wheat and making cheese
But the reality:
Those who take this approach struggle to compete with those leveraging corporate networks (faster product velocity, algorithmic distribution, network effects).
Thus freedom’s context has changed. For the majority of people, the majority of the time, freedom is not a significant factor in decision-making about which apps and services to use.
Evidence: Terms of Service have gotten out of control, but that doesn’t stop anyone from accepting them. Most people just want tasty, cheap, and fast pizza—even if it’s full of saturated fats.
So What Do People Actually Care About?
People care about having the resources they need to survive and thrive (and one-up the Joneses, of course). As we spend more of our lives online, we need to use that time to make a living—to make money.
Ecommerce is a straightforward way to make money online. WooCommerce is an ecommerce solution built on WordPress.
What Merchants Actually Consider When Choosing Ecommerce Platforms
According to ChatGPT (and verified by research):
Factors merchants evaluate:
- Price and cost
- Ease of setup
- Customizability
- Integration and plugins
- Scalability
- Payment options and security
- Mobile responsiveness
- SEO and marketing features
- Support and community
- Platform reliability
- Internationalization
- Analytics and reporting
Key characteristics distinguishing successful stores:
- User experience (UX) design
- Customer service and support
- Product selection and management
- Marketing and SEO
- Pricing and promotions
- Technology and integration
- Payment options and security
- Logistics and fulfillment
- Feedback and adaptation
- Branding and storytelling
Freedom doesn’t even get a mention. And that’s fine—assuming open source platforms are winning on all the other factors that matter. But the evidence suggests they’re not.
Who cares about freedom if you don’t make any money?
Even when you are making money, you probably never care about freedom unless you’re unlucky or at the edges of corporate terms of service. Financial security is one of the most important freedoms. For most people, it’s a more relevant and compelling freedom than software freedom.
But Freedom Still Matters
Here’s who cares about freedom: We do. And we should.
The WordPress and open source communities have earned the right to tell this story. I care deeply about freedom because I care about the world my daughter will grow up in—the world all our kids will grow up in.
The question of individual freedom is one of the most important of our time. Avoiding a panoptical dystopia is the foundation of popular fiction, but it’s also a compelling brand story.
Good Freedom vs Bad Freedom
Open source helped WordPress and WooCommerce succeed. It allowed people to freely experiment, innovate, and collaborate—the core strategies behind non-zero-sum games.
But as use cases mature, those same qualities stop being advantages and start becoming disadvantages.
At some point, we know what ‘good’ looks like in a form module, ecommerce solution, or blogging platform. Value is then created by iterating and optimizing that known good, not creating 19 different form modules.
The Brain Development Analogy
There’s a useful analogy in human brain development:
Nerve cells have myelin sheaths that help send signals. As brains get older, myelin sheaths get thicker. This makes it:
- Harder to create new connections (associated with learning)
- Faster at processing existing data (associated with efficiency)
The point: Freedom to experiment and freedom to optimize are both important at different stages of development—true for ecommerce solutions and brains alike.
Open source is great for innovation. Totalitarian control is better for optimization.
But innovation doesn’t stand still. To continue reaping benefits of innovation, platforms must advance as innovation does and accept that most ecommerce is no longer innovative.
How Current Freedoms Are Undermined
| Freedom Offered | How It’s Undermined |
| — | — |
| Anyone can download WooCommerce and host their own store | Hosting your own WooCommerce store is difficult and expensive for average users. Time spent managing infrastructure is time unavailable for marketing and product development. Updates add complexity. |
| Anyone can create themes and extensions | Without quality standards and best practices enforcement, incompatible themes and extensions proliferate. |
| Merchants can take their data and move to another host or service | Ecosystem incompatibility makes this process difficult and expensive—a key churn point. |
| "Democratize commerce so anyone can sell, regardless of income, gender, politics, language, or location" | The potential ability to sell is irrelevant if merchants don’t know how to get stores live and generate traffic. Democratization fails when success requires expensive professionals. |
And so on.
The Data Liberation initiative shows the WordPress community cares. But we can go further.
To liberate data means to free it. What if we could ensure it never needs to be freed because it is already free?
What to Do?
Sticking with Blue Ocean strategy, the work needed is to figure out how to use freedom to Eliminate-Reduce-Raise-Create factors that help people make money online in meaningfully differentiated ways.
Looking Back from December 2025
Writing from 18 months after this essay was published:
What’s Changed:
- AI-generated software (evolution point 4) is no longer theoretical—it’s happening rapidly with tools like Cursor, v0, Claude Code, and Bolt
- WordPress market share continues to plateau while AI-native solutions emerge
- The "freedom vs value" tension has intensified—most users still prioritize convenience over control
- Managed WordPress hosts continue to struggle with identity: hosting or SaaS?
What Hasn’t Changed:
- The fundamental tension between open source freedom and competitive SaaS user experiences
- Most merchants still don’t care about "freedom" as a purchasing factor
- The challenge of translating philosophical values into differentiated products
The Question Remains:
How do platforms built on freedom principles compete in markets where users consistently choose convenience over control? The Blue Ocean opportunity above the red line remains largely unexplored.
Conclusion
This post argues that open source’s core benefit is freedom, but the current state of WordPress and WooCommerce ecosystems limits success. There’s a strong correlation between value creation and loss of freedom in software.
In a technology supercycle, if the goal is to catch up, you’ve already lost—action is required without delay.
The key challenge: How do we make freedom a competitive advantage?
I think freedom is a story that matters and one that the open source community has the right to tell through brand values and actions. We’re all here because we believe freedom matters. Let’s work together to use freedom as a catalyst for growth and success.
The question isn’t whether freedom is valuable—it clearly is, philosophically and societally. The question is whether it can be translated into products, services, and experiences that people choose over more convenient, centralized alternatives.
That’s the work.
Note: This essay was originally written as internal thought leadership exploring strategic questions about WordPress ecosystem growth. I’ve adapted it for public discussion about how open-source platforms compete with proprietary SaaS in an increasingly centralized internet. The core strategic analysis applies broadly to any open-source project facing similar challenges.
Series Navigation:
- Part 1: There Is No Host – Why WordPress needs to hide the plumbing
- Part 2: On Software and Freedom (this post) – The inverse relationship between value and freedom
- Part 3: Freedom Stacks – Leveraging emerging technologies for freedom-based differentiation