The Problem
In 2009, I stumbled onto a thread on Typophile—a well-known typography forum—where someone had asked about open-source fonts. The response was immediate and hostile:
"How dare you?"
"This will destroy our profession."
"Real designers pay for type."
I had just started teaching myself to code. Open-source had been essential to my learning—programmers shared knowledge freely, helping each other grow. Why wasn't typography the same?
The Stakes
This wasn't just about fonts. This was about who gets to be a designer.
Every day, talented creators were being locked out of their craft. Design students couldn't experiment without breaking the bank. Small nonprofits couldn't afford professional typography. Independent publishers were stuck using the same overused fonts.
The gatekeepers claimed they were protecting the craft. But they were really just protecting their monopoly on knowledge.
Working at A Good Company with Caroline, we'd already seen how sharing knowledge could transform an industry. That hostile forum response wasn't just an insult—it was an opportunity to prove them wrong.
The Revolution Begins
I teamed up with Caroline Hadilaksono, my design partner. She had an unfinished type project from college—the perfect starting point. That became the first-ever open-source font in The League of Moveable Type.
But releasing fonts was just the beginning. We needed to build:
- Websites that could scale with our vision
- Branding that could stand the test of time and feel like it'd been around forever
- A community that could sustain the revolution
I spent nights and weekends:
- Building our platform from scratch in Ruby on Rails (we're fancier than that now — Next.js, TypeScript, etc)
- Writing a manifesto that sparked heart in the people who needed to hear it
- Creating a brand identity that was bold, but stood next to the greats
- Developing a community that would be there for the long haul
The Experimental Journey
Where others saw just free fonts, I saw the opportunity for a real, thriving business. But I had no idea how at first. So I experimented. A lot.
1. Sponsored Content
I partnered with brands to create valuable, insightful pieces that aligned with our mission.
It meant I had to write a lot of copy, and I was good at it — but it didn't feel scalable, and could easily fall into the trap of being a "content farm".
It worked—but didn't feel deep enough to sustain our vision.
2. Merchandise with Meaning
The "I Am That Quick Brown Fox" tee became more than merch—it became a statement piece for designers. I:
- Sourced the softest fabrics from Brooklyn suppliers
- Managed screen printing quality control
- Built an e-commerce system from scratch
- Ran email marketing campaigns that sold out multiple batches
- Packaged and shipped orders from my apartment, with hand-written notes to each customer to thank them for their support
That, of course, led me to research and find a print-on-demand service that could handle the volume, and I built an e-commerce site from scratch to handle the orders.
And it worked for a minute, but didn't feel as meaningful and impactful as I knew The League could be.
3. Custom Typography
We pursued commissioned typeface expansions, working with brands to create custom versions of our fonts. This proved we could:
- Maintain open-source principles while generating revenue
- Create professional-grade custom type
- Build sustainable relationships with major brands
It meant we got to work with big brands like NBCUniversal and others, and I got to flex my client and negotiation skills, fighting on behalf of the type designers who'd contributed to open-source with real significant financial support.
This led to a lot of great work, but it also led to a lot of frustration. It felt like I was just making fonts for brands, and that wasn't who The League was. It was an opportunity to show that open-source could be a viable business model, but just like any high-touch business, it was a lot of work.
4. The Breakthrough: Education
After my time at General Assembly, I was hooked on education, and saw the opportunity to help designers truly understand type. For months, I'd stay up late writing in-depth typography lessons, and sending them out to our newsletter.
The response was overwhelming. Designers weren't just hungry for fonts—they were starving for knowledge.
This led to:
- Writing "Making Sense of Font Licensing" - a guide that demystified the industry. I wrote it in a cafe in Los Angeles over a long weekend, and it was the first time I'd written so in-depth. I had no idea writing a book was possible.
- Developing our first major course on type design fundamentals — a true labor of love, partnering with Thomas Jockin of TypeThursday fame to develop the curriculum, and I personally led the marketing, production, video work, and tech.
- Creating a complete learning platform from scratch — to deliver workshops, courses, and more, that we were partnering with industry leaders to deliver as live events, with multi-week, in-depth newsletters funnels I'd write myself.
- Launching a typography podcast that built our authority with my then-business partner, Olivia, curating news and trends to share every week with the community, with weekly deep dives on typography topics and interviews with industry leaders.
This is still happening today, and I'm proud of it — I'm developing deeply thoughtful, in-depth courses and learning paths to both teach and curate the best in typography education. We're building the best design school in the world, online, accessible to everyone around the world, and in a way that's never been done before.
The Transformation
What started as a response to hostility grew into something far bigger than fonts.
Our work began appearing everywhere—from indie magazines to major websites, from student projects to corporate identities. Design educators started including our fonts in their curricula.
Each experiment taught us something valuable. The failures showed us what didn't work; the successes pointed us toward what did. Most importantly, they helped us build a comprehensive skill set:
- Technical: Platform development, e-commerce, content delivery, AI and deeply thoughtful educational content development
- Creative: Brand design, product design, educational content and web design
- Business: Marketing, fulfillment, customer service, experimenting with new business models
- Community: Event planning, mentorship, online engagement
The Impact
The League proved something powerful: when you break down walls and share knowledge freely, everyone wins. Here's what that looks like in real numbers:
- Used in 204 countries around the world
- 35,000+ engaged subscribers with a 26% open rate and 1.7% click rate
- 30,000+ monthly visitors drawn by our free, high-quality fonts
- 12 curated workshops, 5 in-depth courses so far, 100+ hours of content on typography, lettering, pricing, and more
- 17 open-source font families used by major brands worldwide
Our fonts have been used by an incredible range of organizations and projects:
- Major brands: NBCUniversal, Instagram, Whole Foods, MasterClass
- Entertainment: Lady Gaga, The Hunger Games, DC Comics
- Media: Wired Magazine, Pitchfork
- Politics: Barack Obama's campaign
Most importantly, we've proven that education is the key to industry transformation. When you combine open resources with thoughtful, structured learning, you don't just teach skills—you create new possibilities.
Your Turn
Every field has its gatekeepers, its "that's just how things are done" defenders. But the real opportunity isn't just in challenging assumptions—it's in building better ways to learn.
I've spent years proving that technical education can be different. More human. More accessible. More transformative.
The League began because I dared to ask "why not?" Then I built something that answered that question through code, design, community, and most importantly, through education.
Now I'm ready to bring that same revolutionary approach to technical education at scale. Because the next generation of creators deserves better than gatekeepers—they deserve guides.