Oxford: A Thousand Years of Inspiration
I walked through Oxford’s cobblestone streets, past the library where Tolkien wrote the Lord of the Rings and the door that inspired The Lion, the Witch, and the Wardrobe.
These weren’t just tourist attractions—they were my daily surroundings during one of the most transformative periods of my professional life.
My decision to pursue an MBA at Oxford represented something fundamentally different from my previous educational experiences.
Unlike undergraduate studies, which often feel like an expected continuation of one’s academic journey, pursuing an MBA was a deliberate choice.
It wasn’t something I was “supposed” to do—it was something I actively wanted. This distinction made all the difference.
The Power of Intentional Learning
Going to do an MBA was something that I actively chose, and I think the result of that decision being made by the 200+ people that were in my cohort meant that the level of energy and commitment to making this an incredible environment together was so obvious.
There was an environment that forced me to be my best every day, and ultimately was a large reason as to why I decided to go back into the education space later and to build LOTI.
I think I had never felt so intellectually stimulated.
This dynamic highlighted something I’ve carried forward in my career: the power of environments where everyone has actively chosen to participate.
Whether in business or education, the quality of engagement transforms when people are present by choice rather than obligation.
The Cafeteria Effect
I learned more in the cafeteria than I did in the classroom.
Showing up every day, meeting people from all corners of the world, people who were well-informed on topics that I thought I knew a lot about, but clearly I didn’t—this was an environment that forced me to be my best every day.
During meals and coffee breaks, conversations with classmates exposed me to perspectives I hadn’t considered and knowledge domains I’d barely explored.
I’d sit down thinking I was well-informed on a topic, only to discover through casual conversation that my understanding barely scratched the surface.
These impromptu exchanges challenged me intellectually in ways formal instruction rarely could.
They forced me to question assumptions, defend positions, and regularly update my thinking based on new information—all within the context of relationships rather than academic requirements.
This experience reshaped my understanding of how learning works at its best.
While structured education provides necessary foundations, the transformation of knowledge into wisdom often happens in these interstitial spaces—the conversations between classes, the debates over dinner, the late-night discussions in common rooms.
Being a Step on the Timeline of History
There’s just something unmatched about being a step on the timeline of history and what Oxford is.
This historical context wasn’t merely decorative—it was instructive.
Walking the same paths as great thinkers and innovators from centuries past created a humbling perspective on my own work and ambitions.
In a place where time is measured in centuries rather than quarters, I gained a longer-term view of what constitutes a meaningful contribution.
When I reflect on my time at Oxford, I’m reminded that the most valuable education often happens outside the formal curriculum.
It occurs in the spaces between—the conversations, connections, and contexts that transform information into understanding and facts into wisdom.
The Infinite Learner: From Newsletter to Startup
When COVID-19 hit in 2020, I felt the entrepreneurial itch again.
After four years at Netflix building products, I was ready to return to building something from zero to one.
So I left Netflix at the end of 2020 and, as I like to joke, “like any great millennial founder, I started a newsletter before starting a business.”
That newsletter was the infancy of The Infinite Learner, and it would eventually lead to my next startup venture.
Starting with Curiosity
The genesis of The Infinite Learner was straightforward: I was eager to build something in the education space, specifically around professional development, but I recognized the limitations of my knowledge beyond my personal experience.
Rather than simply cold-calling experts and asking to pick their brains, I took a different approach. I reached out with a more appealing proposition: “Can I interview you?”
Whether due to COVID-19 creating more available time or simple vanity (probably a combination of both), over 90% of the people I contacted responded positively.
This opened doors to conversations with an incredible range of people—entrepreneurs, academics, venture capitalists, and professionals across various fields.
These interviews became the foundation for a weekly newsletter, creating a forcing function that compelled me to articulate everything I was learning.
The process of distilling sometimes complex subjects into clear, digestible content wasn’t just valuable for readers—it was transformative for my own understanding.
Having to explain concepts simply forced me to truly grasp them first.
The Birth of Learning On the Internet (LOTI)
Through these conversations and the process of writing The Infinite Learner, I developed the concept for LOTI.
The inspiration came from a simple observation: I had just spent four years helping build what was arguably the world’s greatest personalization engine for entertainment content at Netflix.
Could I apply that same logic to professional development content?
In 2021, I launched LOTI with this vision.
Given the circumstances of COVID-19—with individuals more motivated to upskill themselves and companies more willing to invest in remote professional development—the business initially performed well.
The company aimed to create personalized learning experiences, matching individuals with the professional development content most relevant to their specific needs and learning styles.
Just as Netflix recommends shows based on viewing patterns, LOTI would recommend learning resources based on career goals, learning preferences, and skill gaps.
The Reality Check
As the market shifted in 2022 and 2023, with tech companies implementing layoffs and cutting budgets, I had to confront a difficult reality: I had built what I call “a vitamin, not a painkiller.”
In other words, LOTI was a nice-to-have rather than a must-have solution.
In 2023, I threw everything at the wall to see what would stick, but ultimately had to acknowledge that the customers we had acquired wouldn’t support the large business I had envisioned.
Someone who was working with me on the project ultimately took over, and I decided to move on.
Lessons from the Journey
The evolution from The Infinite Learner newsletter to LOTI and its eventual transition teaches several valuable lessons about entrepreneurship:
- Start with learning: Beginning with a newsletter allowed me to build knowledge and connections before committing to a specific product direction.
- Market timing matters: LOTI initially benefited from COVID-related changes in learning and development priorities, but those advantages weren’t permanent.
- Vitamins vs. painkillers: Products that are nice to have but not essential face particular challenges when market conditions tighten.
- Adapt or transition: Recognizing when to pivot—or when to let someone else take the reins—is an essential entrepreneurial skill.
While LOTI didn’t become the large-scale business I had envisioned, the experience provided valuable insights that continue to inform my approach to building and evaluating businesses.
The Connected Learning Journey
My experiences at Oxford and with LOTI, though seemingly disconnected, share a common thread: they both represent environments where intentional learning creates opportunities for transformation.
At Oxford, I found myself in a space where centuries of academic tradition combined with a globally diverse cohort of motivated peers to create an extraordinary learning ecosystem.
With LOTI, I attempted to create a digital platform that could similarly connect motivated individuals with the right learning resources at the right time.
Though these experiences took different forms—one as a student in a historic institution, the other as an entrepreneur building a digital platform—both taught me about the conditions under which meaningful learning flourishes.
The fundamental questions I was exploring remain relevant:
- What does the workforce of the future look like? And what role will continuous learning hold in shaping it?
- What products can be developed to create a collaborative partnership between government, private industry, and the individual to promote perpetual upskilling?
- What can be built that will assist people in learning how to learn and better manage learning cycles?
These questions now inform how I evaluate potential business acquisitions through MTL Capital and how I think about creating value in more traditional business contexts.
From Oxford’s ancient quads to my tech startup’s virtual spaces, my journey has reinforced that the most powerful learning happens when we deliberately create environments that challenge us, connect us with diverse perspectives, and compel us to articulate and refine our understanding.
The Infinite Learner began as a name for a newsletter, but it’s also become something of a personal philosophy—a commitment to extracting wisdom from every experience, whether conventionally successful or not.