LMS AT 30History of CourseInfo/BlackboardAn Interactive Memoir

When people tell the history of online learning, they usually begin with the companies that became famous. They begin with Blackboard, with the rise of the learning management system, with the larger transformation of education by the web. But history rarely begins at that scale. More often, it begins in small rooms, with small groups of people, in conversations that do not yet seem historic while they are happening.

That is the part people tend to forget.

They remember the company once it has a name. They remember the market once it has taken shape. They remember the institution once it has become visible. What they often miss is the quieter beginning, the period when an idea is still forming, when the language around it is unsettled, and when the people building it are simply trying to solve a problem that is right in front of them.

For me, that beginning was Cornell University in the mid-1990s.

When I think back to Cornell, I do not remember it simply as the place where I earned my degree. I remember it as the place where several strands of my thinking first came together. Economics, strategy, entrepreneurship, leadership, and institution-building stopped feeling like separate interests and began to form a single way of understanding opportunity.

I was studying in Cornell's Department of Agricultural, Resource, and Managerial Economics, or ARME as it was then known. Most people heard "ARMY" and assumed it had something to do with ROTC, which made for an awkward first impression. But behind the acronym was a program that gave me a serious grounding in economics, strategic thinking, and enterprise.

My formal degree designation was "General Studies," but the name hardly captured what it made possible. It positioned me as an academic scholar with the freedom to shape my undergraduate education in a highly intentional way, choosing the courses that allowed me to bring together managerial economics, entrepreneurship, and the broader questions of strategy and institution-building that increasingly drew my attention.

My undergraduate path was somewhat unique because it allowed me to blend managerial economics with entrepreneurship at a time when entrepreneurship at Cornell was still in a very early stage of development. In those years, the program consisted of only a few courses, and Professor Deborah Streeter, who became my mentor, taught the principal ones. That gave my education a rare coherence. I was not just completing a major. I was developing a way of thinking that connected economics, strategy, and entrepreneurship into a single frame.

Three identities, one operator

What people did not always see, looking at that path from the outside, was that I had also been a self-taught computer scientist for as long as I could remember. I have often thought of myself as a business person by academia, a computer person by personal interest, and a sales-and-marketing person by passion. That combination explains more of my path than any single title ever could.

One of my earliest memories of computing and electronic play came before I had a computer of my own. My dad brought home an early home version of Pong around the time those systems first reached the consumer market in the mid-1970s. Atari had released the arcade version of Pong in 1972, and the home version reached consumers through Sears in 1975. The home version brought that experience into the house. It was simple. It was physical. It connected the television to something interactive in a way that felt new. At that moment, I was hooked on computers and gaming.

As new home gaming systems were released, I found ways to get access to them. The Atari Video Computer System, later known as the Atari 2600, was released in 1977 and became one of the defining home game systems of that period. It took the interaction I had first seen through Pong and extended it through cartridges, joysticks, and a growing library of games. Gaming was not just something I watched from a distance. It was something I followed as the systems came out, as games circulated, and as kids found ways to play, share, trade, and get access to whatever they could. Years later, the Sega Genesis arrived in North America in 1989, after Sega had released the Mega Drive in Japan in 1988. By then, home gaming had moved from simple paddles and blocks on a television screen into a much more sophisticated consumer market. But for me the line was continuous: Pong, Atari, Apple, Commodore, Sega, and the larger movement from electronic play into personal computing.

Constraint as teacher

My experience with computers began when I was very young, in the hobbyist phase of personal computing itself. Apple I still belonged to the board-and-kit world. Steve Wozniak had designed it in 1975 and 1976, and Apple began selling it in 1976 as an assembled circuit board rather than as a finished consumer computer. Only around two hundred were produced. The rest of the machine still had to be supplied, assembled, or worked around: the case, the power supply, the keyboard, the display, and the larger environment that made the board useful. The machine was not yet fully hidden from view. It still carried the feeling of assembly, experimentation, and possibility.

Then came the Apple II era. Apple introduced it in April 1977 and began selling it in June 1977. It was one of the first highly successful mass-produced personal microcomputers, with a molded case, integrated keyboard, power supply, BASIC in permanent memory, and color graphics. But even as it moved personal computing toward the consumer market, it still carried some of the Apple I spirit. It still felt close to the earlier hobbyist world. It still felt like something people could understand, explore, configure, and, in a very real sense, build into usefulness. I remember the world of Apple computers when floppy disks still felt enormous — almost the size of your face — and screens glowed in green or amber. I remember black-and-white games, oversized media, and a style of computing that still felt handmade, exploratory, and full of discovery.

That early exposure came before personal computing had fully settled into something polished and ordinary. My dad and I would go in the evenings to the local high school to take part in Apple computer clubs, and those clubs were part of the early hobbyist culture of computing — places where people gathered not just to use computers, but to discover them, trade ideas, share software, and still, in many cases, put them together by hand. The "put them together" part says something about the time. The machine was not yet fully hidden from you. It still invited curiosity. It was very much the Radio Shack spirit of that era: experimental, hands-on, and driven by people who were as interested in how the machine worked as in what it could do.

There was also a practical side to that world. The Apple computers themselves were often financially out of reach, and even the supplies around them could be expensive. Floppy disks were part of that. When double-sided, double-density disks became available, I could not simply buy as many as I wanted. So I learned the workaround. I started punching the other side of single-sided floppy disks so I could flip them over and use the other side. It was a risk. The disks were not sold for that purpose. But it doubled the usable storage, and at that point storage mattered. That was part of the same education. You learned the machine. You learned the media. You learned the limits. And when the limits got in the way, you found a way around them.

Not long after, the Commodore VIC-20 became another important step in that journey for me. Released in 1980, it was the predecessor to the more widely known Commodore 64. Apple computers were financially out of reach, so the VIC-20 became the machine I could actually have and use. With its tiny 5 KB of memory, it demanded a kind of discipline that now feels almost unimaginable. But at the time, it was more than enough to draw me further into programming. I created simple games and saved them onto a tape drive. That was not just about playing with a machine. It was about beginning to understand logic, sequence, structure, and the satisfaction of making something work. The limitations themselves became a kind of teacher.

Pattern recognition as the founder edge

That whole world shaped me more than I could have known. It left me with an instinct for pattern matching, especially around technology, momentum, and emerging change. It trained my eye to notice when something was beginning to shift, even before the broader culture had language for it. That instinct would matter later, because one of the deepest advantages I had in the CourseInfo years was that I could often sense the direction of technical change before many people around me could see its practical consequences.

By the time I arrived at Cornell, I had years of hands-on computing experience behind me. And in college that instinct did not disappear; it took on another form. I spent time taking apart and rebuilding personal computers in the era when Michael Dell was demonstrating that there was a real market for direct-built PCs. That was another important chapter in the evolution of personal computing: the shift from hobbyist discovery toward performance, accessibility, and a more modular, configurable machine culture. My first PC at Cornell was actually one my brother had brought with him. As I remember it, it was an IBM 486 DX2-66, or something close to that class of machine, which he had used during an internship with Xerox. It became part of how I lived inside the technical environment of the campus. I remember the mindset of that era clearly — the case opened, the parts visible, the machine understandable in a physical way. You could take it apart, improve it, rebuild it, and know it more intimately afterward.

That same environment changed the way I approached academic work. I remember handing in papers to instructors that looked different from what most students were submitting at the time. One paper I wrote on Positron Emission Tomography had a full-color cover, protected by a transparency sheet. It was also littered with HTML web references at a time when even faculty were only beginning to become familiar with the technology. My brother not only had a computer; he also had a full-page color printer. That changed what was possible. I would sometimes get funny looks from professors when I handed those reports in, but I also remember ending up with A's because the reports were unlike anything they had seen before.

On that same computer, we would move from academic work into PC computer gaming. That opened up another world. It showed how quickly computers were advancing, not only as tools for writing and research, but as machines for simulation, graphics, interaction, and play. The games themselves were becoming more complex. Some were already large enough to be split across several CD-ROMs. That was another signal. The computer was no longer just a machine for schoolwork or programming. It was becoming a platform for experiences that were bigger, richer, and more demanding than anything I had seen in the earlier cartridge and floppy-disk world.

Living inside the shift

During that same period at Cornell, I was already living inside a networked campus environment. We were connected through Bear Access and Eudora, and Cornell's high-speed on-campus network made digital access feel like part of daily academic life. I was already experiencing the possibilities of what the internet could do for students, professors, and the university: information, communication, course work, and digital access moving through the network instead of remaining tied only to paper, place, and physical handoff.

So while my formal academic path was framed in the language of economics and entrepreneurship, the technology had been there alongside me all along, quietly shaping the way I saw problems, systems, and possibilities. That is part of why it has always been difficult to reduce my skills to a single title. I was learning business in the classroom, but I was also learning systems by taking machines apart, rebuilding them, programming them, and living through the earliest stages of personal computing culture itself.

My early exposure to computing gave me an instinct for pattern recognition and the momentum of technological change. My academic life gave me structure in economics, strategy, and entrepreneurship. And my passion for sales and marketing taught me not only how to listen for the conversation beneath the conversation, but also how to boil down complex ideas into smaller, clearer ones that people could understand and latch onto. CourseInfo, in many ways, was built at the intersection of those three instincts.

By the time I arrived at Cornell, computing was not abstract to me. It was something I had handled, opened, repaired, programmed, worked around, and learned from. That mattered later because CourseInfo was never just a business idea to me. It was a system problem, a user problem, and a market problem all at once.

That intersection did not develop apart from Cornell. It developed inside Cornell. The academic structure gave me the language of economics, strategy, and enterprise. The computing background gave me a way to understand systems, tools, and emerging technology. The entrepreneurship program, and Professor Deborah Streeter's role in it, gave those strands a place to come together.

Professor Deborah Streeter was one of the defining forces in Cornell's entrepreneurship ecosystem at the time. Her impact reached far beyond the students in her classroom. She was helping build the larger culture of entrepreneurship at Cornell itself — connecting students, alumni, ideas, and institutions in ways that gave the ecosystem both energy and structure. It is hard for me to imagine that early Cornell entrepreneurship world without her at the center of it.

This was still a period when entrepreneurship education was far less common and far less developed across universities than it would later become. The entrepreneurship system that exists at Cornell today was still barely there in the form we would have needed while we were there. Streeter was one of the people helping make that future possible long before it became visible in the form it would later take. And the longer arc of that work is visible in what came after, including the fact that Cornell students can now pursue entrepreneurship in a formal minor alongside their major.

There was a larger and more interconnected Cornell entrepreneurship world around us than any of us fully appreciated at the time. In different ways, Professor Deborah Streeter and Cindy van Es were powerhouses inside that Cornell environment. Streeter was helping build the entrepreneurial culture and institutional frame. Van Es created the instructional setting where the course-material problem became immediate, practical, and real. Deborah Streeter stood at the center of much of the entrepreneurial and academic energy that shaped me directly. Cindy van Es created the immediate instructional context in which the need for digital course tools became real and urgent. Margaret Corbit represented part of the technical and institutional network around the Cornell Theory Center that helped make ambitious ideas feel possible. And Debra Moesch-Shelley was part of the Entrepreneurship and Personal Enterprise infrastructure that helped give Cornell's entrepreneurial culture practical shape. Along with figures like John Jaquette, these were some of the people and structures that made the Cornell environment far more powerful than we understood while we were living inside it. We credit Streeter, van Es, Corbit, Moesch-Shelley, and Jaquette with a meaningful part of our success. Each stood in a different place in the Cornell ecosystem, and together they helped create the conditions that made CourseInfo possible.

Teaching reveals product gaps

That sense of coherence deepened as I moved from being simply a student of entrepreneurship to becoming an active participant in the life of the program itself. I first encountered Professor Deborah Streeter's teaching as a student in her 325-level business planning course, and later in her 425-level business consulting course. The 425 course was especially important to me, because my work there, together with my team, received an award from Cornell, an early affirmation that I could operate in a more demanding and strategic environment. From there, my relationship with the program deepened even further when I returned not as a student, but as Professor Streeter's administrative teaching assistant for the 325 business planning course. It was a significant responsibility for an undergraduate. I oversaw eight other TAs and helped support roughly ninety students, organized into teams of three, as they learned how to write and develop business plans. It was one of the first moments in my life when I moved from being simply a student of entrepreneurship to helping shape the environment in which it was taught.

Professor Streeter taught me several lessons, not only inside the classroom and not only through her support of the Cornell Entrepreneur Organization. She also taught through the kinds of technology and instructional methods she was adopting in the classroom itself. In her class, each session included a prerecorded video of an entrepreneur teaching a lesson about the challenges and opportunities that existed inside an entrepreneurial journey. These were real people solving real-world problems and turning them into successes. That was part of the instruction. It made entrepreneurship real. It empowered and motivated students to think about how they could become active participants in change, not just observers of it. It gave students a way to see entrepreneurship not as an abstract topic, but as a lived process carried by people who had already built, struggled, adjusted, and learned.

At the same time, I began to feel the limits of the classroom alone. I wanted to help create a wider entrepreneurial culture at Cornell, something that would connect students not only to ideas, but to people, opportunity, and example. That led me to found the Cornell Entrepreneur Organization. Part of what I had in mind from the very beginning was bringing business students and engineering students into the same room. I believed the most interesting opportunities lived at that intersection, where business thinking and technical building could meet. In those years, entrepreneurship at Cornell was still in an early stage, and the organization became a way to build community around it: bringing entrepreneurial alumni back to campus, creating practical networking opportunities, helping students see entrepreneurship not simply as an academic interest, but as a lived and attainable path, and building bridges between disciplines that did not always cross.

Sell the category before the product

In many ways, the Cornell Entrepreneur Organization became a master class in marketing and communications. We had to prove the entrepreneurial value proposition to students before entrepreneurship had the campus visibility it would later have. We had to explain why they should come, why the speakers mattered, why the network mattered, and why they should see themselves as part of that world. The speaker series gave students access to entrepreneurs and alumni. The organization gave them networking opportunities. We even printed what were, for many students, their first networking business cards. It gave students a way to present themselves and a reason to put "CEO" on their resumes. Those details were practical, but they were also part of the lesson. Entrepreneurship had to be communicated, packaged, and made useful before it could spread.

The bridge you build before you cross

What I did not realize at the time was that the very partnership that would define my early career was going to come out of exactly that kind of collision. I was building the bridge before I knew I would walk across it myself.

I also had the opportunity to work closely with my mentor in carrying entrepreneurship beyond the classroom. On Professor Streeter's recommendation, the Cornell Entrepreneur Organization adopted the Sam Seltzer speaker series, named in recognition of Samuel Seltzer '48, whose support helped create the Personal Enterprise Program, or PEP, in Cornell's College of Agriculture and Life Sciences. PEP was the program Professor Streeter was developing, and the speaker series became one of the ways that work reached beyond the classroom. It brought accomplished Cornell alumni back to campus to speak with students about the realities of building careers, companies, and ideas. Through the Cornell Entrepreneur Organization, I helped make those evenings into more than speaker events. CEO became a driving force in bringing students into the room and into the conversation, creating a space where alumni could share what they had learned and students could begin to imagine themselves at that same table one day.

To build the Cornell Entrepreneur Organization, I recruited seven other students to help me manage and grow it. They became an important part of the effort almost immediately. Many of them would approach professors and ask for five minutes at the beginning of class so they could step in, speak directly to students, and build awareness of what we were creating. In a remarkably short period of time, CEO became the fastest-growing student organization on campus. Within six months, it had also become the largest student organization on campus and the one with the most financial resources. What stayed with me was not just the speed of that growth, but the deeper signal behind it: students were eager for a stronger entrepreneurial culture, and when given the chance, they responded with real enthusiasm.

All of this was happening at the same time that I was serving as the administrative teaching assistant for Professor Streeter's business planning course. The two roles began to intersect in a meaningful way. Launching CEO and serving as the administrative teaching assistant taught me how to motivate and manage people in dynamic environments. One role required me to help organize teaching assistants and student teams inside a demanding academic course. The other required me to recruit, encourage, and coordinate students around a new entrepreneurial organization that was growing quickly. With Professor Streeter's support, I was given access to a multipurpose room that became a kind of shared home base for both the teaching assistants in the course and my team in the Cornell Entrepreneur Organization. That was more important than it may have seemed at the time. It gave me a physical space where the discipline of the classroom and the energy of student-led entrepreneurship could meet, and where I could begin to see how culture, leadership, and institution-building often grow side by side.

At the same time, I was fortunate to be one of the first students to sit on the Entrepreneurship@Cornell advisory council while still an undergraduate. Entrepreneurship@Cornell was emerging as a university-wide effort to connect entrepreneurship across Cornell's schools, colleges, alumni, faculty, students, and business community. The advisory council brought alumni and business leaders into that work, giving the program a way to connect student energy and faculty leadership with mentorship, outside perspective, and broader institutional support. That experience gave me a broader institutional perspective. I was not only participating in Cornell's emerging entrepreneurial culture through coursework, teaching, and student leadership; I was also helping to think about how that culture could be shaped, strengthened, and extended across the university.

Doing more makes more possible

At Cornell, I also learned an important practice. Just when you think you cannot do any more, you find time to fit it in. Or, put more simply: the more you do, the more you can do.

It was through that overlapping world of coursework, teaching, student leadership, and institutional involvement that I first came to know Dan Cane. In the fall of 1996, Dan was one of about ninety students in ARME 325, "Business Planning for Entrepreneurs," taught by Professor Deborah Streeter, Cornell's Bruce F. Failing, Sr. Professor of Personal Enterprise. I was serving as the administrative teaching assistant — the Zalaznick Teaching Assistant in Entrepreneurship and Personal Enterprise — inside CALS's Entrepreneurship and Personal Enterprise Program, coordinating with Professor Streeter and managing the team that was building the Cornell Entrepreneur Organization in parallel. Meeting Dan in that context was ordinary. I may have bumped into him once or twice during the teaching of the course, but those moments were not yet historic. Dan was a student. I was the administrative TA helping indirectly as ninety students developed business plans. Dan was one in the mix of students.

His team presented a K–12 education website concept called EleFun, complete with an elephant as its mascot. It was a student project, but even then there was something larger in the way he approached it. He was building a website for K–12 students, and that is what made it unique. He was not simply trying to finish an assignment. He was already using the web to think about education, access, and the way students might engage with learning differently. At first, our connection seemed entirely ordinary. Only later did I understand that it would become an important relationship within my early professional life.

As the semester drew to a close, Dan approached me to talk more seriously about some of the work he had begun doing with faculty who wanted to put course information online. He invited me to meet him at Ruloff's in Collegetown. Nothing about the setting suggested history. It was just a conversation between two Cornell students in a familiar campus place. But that is often how these stories begin, not with ceremony, but with a conversation that only reveals its significance in retrospect.

At Ruloff's, Dan began describing the work he had been doing building web pages for professors. Cindy van Es was another important common point between us. She was part of the ARME environment I knew, and she was also the professor whose course gave Dan the immediate instructional problem he had begun working on. The work had begun as an independent study with Professor Cindy van Es in her ARME business statistics class, where he had started by digitizing her syllabus, class notes, and answer keys. The problem was familiar to us as students. When we missed class, or when we needed to stay caught up, we often had to trudge up Libe Slope to Warren Hall to get the sheets of notes that had been placed outside the classroom. There had to be a better way. In that conversation, Dan and I explored that idea thoroughly: making those kinds of materials available to students more directly, including students like us.

What quickly became clear to me was that this was not simply a collection of isolated projects. There was a larger need beginning to emerge. Faculty wanted a practical way to publish course information and materials online. Students wanted easier and more reliable access. We both understood that universities were beginning to feel the pressure of those needs, but the systems to support them did not yet really exist. We had jointly come to the conclusion that it was more than work. It was the outline of an opportunity that neither the market nor the institution had fully named yet.

When Dan and I met at Ruloff's, he told me something I never forgot: he had deliberately refused to join the Cornell Entrepreneur Organization because it had grown so strong that, from the outside, it almost felt like a cult. There was irony in that, of course. The journey we were about to begin together would create a very similar dynamic — not in any unhealthy sense, but in the deeper sense of belief. CourseInfo quickly became a magnet for people who believed in the mission, in what we were trying to do, and in the possibility that higher education could work differently. In fact, Dan used that very point as one of the reasons he wanted me involved. He had seen that I could build not just an organization, but belief.

Dan told me he was looking for a founding business partner, someone who could help shape the business strategy, development path, sales, marketing, and organizational growth around what he was beginning to build. I could see immediately how my own path had prepared me for that moment. Dan brought technical vision and the instincts of a builder. What I brought was a more hybrid mix: the strategic structure I had developed through economics and entrepreneurship, the technical intuition that came from years of living inside computing culture from its earliest hobbyist stages through the more modular PC era, and the sales-and-marketing drive that made me want not only to understand a solution, but to help it find its audience. By the end of that conversation, we jointly knew that we wanted to build it together.

Filing CourseInfo LLC

Not long after that first conversation, Dan and I formalized our partnership as CourseInfo LLC, going downtown to create the company in the Town of Ithaca. Dan and I were the original business partners of CourseInfo, building it together from its earliest days. On the surface, it may have looked like a straightforward legal step. But in memory it feels much larger than paperwork. It was the moment when a shared idea became a shared commitment, when something that had lived in conversation began to take on the weight and shape of a real venture.

It began in late 1996, when this small CourseInfo team followed a shared passion: putting course materials online for the instructors we knew, and for the students we were. We pooled what we had — the problem, the code, the plan, the business model — and we kept building.

The early team takes shape

At the time, Dan was living on Linden Avenue with housemates, and I was living on Catherine Street with my brother, since we had ended up at Cornell at the same time. We were only a couple of blocks apart in Collegetown, and that detail has stayed with me because it says something about the nature of those early days. CourseInfo did not begin in a boardroom or office park. It began inside the ordinary geography of student life, where classes, friendships, work, and new ideas all seemed to run into one another.

Dan likes to say that, when he first came to Cornell, he unknowingly met many of the people who would later become part of the CourseInfo story. That did not all happen at once. The team formed over time. But in hindsight, the relationships were already there before the company itself had fully taken shape.

After we formed the business and began working out of Linden Avenue, for a while it was really just Dan, me, LJ — John Yang — and John Knight, along with the others who soon gave CourseInfo its next layer of strength. John was our friend, our Cornell brother, and our CourseInfo brother, and we miss him dearly. At one point he started wearing oversized sunglasses that made him look, to the rest of us, a little like a bug. He loved them. We teased him enough that "Bug" became the nickname that stayed with him. LJ, however, remained LJ, and that nickname has stayed too. Those are the kinds of details memory keeps because they carry both affection and loss.

After that first summer, the circle widened. Stephano Kim and Tim Chi came back into the work, and not long after, Lee Wang joined the group as well. Along with John Yang and John Knight, they became part of the early team that gave CourseInfo its next layer of strength. What mattered was not just that we had smart people, but that we had an unusually complementary mix very early on — product, engineering, finance, sales, and marketing all beginning to take shape around the same idea.

That complementary mix became clearer as each person found a role inside the work. Stephano Kim focused on the business side and the financials, helping give structure to the company as an operating venture. Dan functioned, in practical terms, as the company's CTO, and together with Tim Chi built the bulk of the CourseInfo platform. LJ — John Yang — focused on infrastructure, networking, and connectivity, supporting the systems environment that made the product work. John Knight focused on software engineering in support of Dan and Tim and became the core owner of the assessment engine. Lee Wang came in as a utility player, but over time he picked up the reins with me on sales, marketing, and outreach. Those roles mattered because CourseInfo was not built by one kind of person doing one kind of work. It required product vision, engineering, infrastructure, finance, customer development, and market communication to come together at the same time.

Carving out the cap table

As the work evolved, Dan and I also had a direct one-on-one conversation about the cap table. We understood that the company had begun with the two of us as the original business partners, but we also understood what was happening around us. Tim, Stephano, LJ, John Knight, and Lee were not just helping around the edges. They were becoming central to the company's ability to build, operate, sell, and support what CourseInfo was becoming. Dan and I talked about carving out a small part of the business's cap table so the rest of that team could participate more fully in the company itself.

The decision reflected how we actually experienced the work. CourseInfo was not being built as a narrow two-person story. It had become a small team story, with each person carrying a real part of the load. As certain early team members became deeply involved in building the company, we made a conscious decision to have those active contributors participate more fully in the business itself. Over time, the natural result of that was that they came to be regarded, affectionately and meaningfully, as co-founders. In that sense, the early life of CourseInfo was shaped not only by its original formation, but also by a broader group whose contributions became inseparable from the company's story.

Product discovery and "big ears"

By then, I had graduated, while Dan still had another year to go at Cornell. We spent the following summer working closely together in Ithaca, at Cornell, refining both our understanding of the problem and the shape of the solution. Those months established the rhythm that would define our partnership. I was out doing outreach, meeting with potential customers, listening closely to what they needed, and gaining further insight into how the problem we already understood from Cornell would translate into broader market adoption. That work drew on all three parts of me at once: the business side that looked for structure and viability, the technical side that had been formed through years of hands-on computing and pattern recognition, and the sales-and-marketing side that cared deeply about language, positioning, and traction. I was also working on and writing pieces that would help describe what we were doing to the market. I would bring those insights and that language back to Dan, and he would build in response to what we were learning.

That process strengthened one of the most important entrepreneurial disciplines I would rely on thereafter. I have often said that if you want to be successful as an entrepreneur, you need big ears. It takes big ears to listen to the conversation beneath the conversation. You cannot be so self-absorbed or so fixed in your ways that you cannot hear what your customer base is telling you. More than that, you need to learn how to listen to the conversation beneath the conversation. It is not enough to hear what one person says in isolation. The real work is to reconcile what many people are saying, to hear the patterns beneath their words, and to find the common ground that can become the basis of a successful product.

Cornell as a wired environment

Being at Cornell gave us an advantage. Cornell housed the Cornell Theory Center, one of the original National Science Foundation supercomputer centers, and the university sat inside a research network environment that was unusually advanced for the time. Cornell felt that way from the inside as well. We had Bear Access, a simple, menu-driven gateway into network life on campus: click "E-mail" and Eudora opened, click "Web" and Netscape opened, and if the needed software was missing, Bear Access could even install it for you. It made the network feel immediate and usable in a way that was rare at the time. That atmosphere was captured memorably in the "Cornell is WIRED!" moment and the larger sense that Cornell was living in a technical future before most places were. We were living it. We were experiencing it. And we wanted more of it.

But the rest of the world was not Cornell. CourseInfo was being built in a pre-internet, pre-dot-com moment, when we were living inside a technical and networking bubble that most people outside it had not yet entered. The common person had not even heard the term "internet," much less begun to imagine it as a platform for business, communication, or education. That distance between our environment and the broader culture shaped everything. It fueled our creativity because we could see possibilities others could not yet see. But it also made the company harder to explain, and later, harder to finance.

Living the problem from inside it

What gave us an advantage was not just the technology around us, but the fact that Dan and I were both living the problem ourselves. Dan was living it from the student and builder side, already working directly with faculty who were trying to move course materials online. I was living it as a student as well, but also as the administrative teaching assistant, which meant I was sitting directly in the middle of the teacher-student problem. Dan could feel the technical friction and possibility from inside the emerging work itself. I understood the student side because I was living it, but I also understood the faculty side because, in a very real sense, their problems had become my problems as well. I was helping coordinate the environment between instructors and students, seeing firsthand where communication broke down, where access was difficult, and where friction accumulated. So by the time Dan came to me, it was not as if a light bulb suddenly went on. The light was already on; it simply grew brighter. That closeness mattered. One of the best places to be as an entrepreneur is intimate with the problem, because when you are living it yourself, it becomes much easier to recognize a solution that is both real and necessary. It also becomes easier to translate complexity into something other people can actually grasp. I have always had a knack for boiling down complex concepts into smaller, clearer ideas that people can understand and latch onto. That, for me, has always been part of the deeper craft of sales and marketing. It was never just about promotion. It was about translation. In that sense, we were not just building for a market. We were, in a very real way, our own first customers.

This was a convergence of timing, environment, and problem. We were inside an unusually wired university. We were close to a problem we were living ourselves. We were standing at the edge of a technological shift that most of the world had not yet fully recognized. In the span of a few months, those forces came together: the needs of students and faculty, the possibilities of the early web, the creativity of a handful of smart undergraduates, and the conviction that we could build something useful before the market fully understood what it needed. Out of that convergence came the invention of what would become a course management system.

There was another strand feeding into the story as well. The summer before, Dan and Tim Chi had spent time as interns at Intel, and as I remember it, that was where they learned PHP. When Tim came back, he and Dan became the two people driving the development work in earnest, and that continued as the product evolved. Their interest in scripting and dynamic web behavior was no longer abstract. It had become part of how they thought. While Dan and Tim focused on the engineering, I became the interface for product strategy — helping interpret the need, shape the direction, and connect what we were building to the people and institutions it was meant to serve. We were not just in the environment at Cornell; we also had relationships with people in it. Margaret Corbit was part of that larger world. She later recalled that Tim and Dan wanted to build websites, which captures something important about that moment. We were close enough to the technology, and close enough to the people around it, that what we were trying to do did not seem impossible. It seemed early, ambitious, and real.

From course pages to Teacher's Toolbox

In the earliest stage, Dan's work with Professor van Es began as a website with course pages. The initial problem was concrete and immediate: getting course information, notes, and materials onto the web in a usable form. But that phase did not remain static for long. Dan had come off his Intel internship the summer before, and by the time I came to know him through my class and then more directly near the end of the term, it was clear that his technical thinking had already begun to move beyond simple pages. What had started as course websites was already leaning toward something more functional, more dynamic, and more ambitious. Once we formed the business together, that evolution accelerated.

Once we founded CourseInfo, we were no longer interested in leaving it as a collection of static pages. That was too small an answer to the problem we were beginning to see. What faculty needed was not simply a prettier way to display course information on the web. What they needed was a practical environment for managing the actual life of a course. That was the shift. Teacher's Toolbox was the first real expression of CourseInfo as a product, not just a set of pages. It was where the company first began to take the shape of something repeatable, structured, and usable beyond one instructor, one class, or one isolated experiment.

We began building what CourseInfo called the Teacher's Toolbox, or TTB. Teacher's Toolbox was the product name at that stage of the company. The name mattered because it captured exactly how we thought about the system. This was not meant to be an abstract technical achievement. It was meant to be useful. It was meant to put tools into the hands of faculty in a form they could understand and actually use. We called its functions generators because that was exactly what they did. The announcement generator generated announcements. The quiz generator generated quizzes. The content generator allowed faculty to post documents and course materials. A pattern was beginning to form around three core needs: content, communication, and assessment. Faculty needed a way to post materials. We, as students, needed a way to receive them without always being tied to a classroom door, a handout pile, or a physical location on campus. Faculty needed a way to communicate with students, and students needed a clearer way to stay connected to the course. Faculty needed a way to ask questions, collect responses, and begin to understand student progress, and students needed a way to participate in those interactions through the web. Over time, the larger logic became clear: we were creating not merely a website, but a set of instructional utilities that supported the real interactions, transactions, and rhythms of a course.

It is easy in retrospect to make the early product sound more static than it really was. From the outside, someone might have looked at those early course sites and seen pages on the web. But from the inside, we were already moving toward something very different. We were building tools, structure, and repeatable functions. The business side of me could see the value of a system that could scale across courses and institutions. The computer side could see how scripting, databases, and structure could make that possible. And the sales-and-marketing side could see that once faculty understood the tools in simple, usable terms, adoption would follow. In other words, the shift from course pages to Teacher's Toolbox was not cosmetic. It was the moment CourseInfo began to become a real product.

Global Gateway and the replication engine

The front end of that environment was what we called the Global Gateway. It was, in effect, the dashboard and entry point into the Teacher's Toolbox — the common front door through which users entered the course environment and navigated its tools. The Global Gateway was not a side feature or a decorative layer. It was the organizing point of entry into the larger system. It gave shape, coherence, and navigability to what we were building. Once you entered through the Global Gateway, you were no longer simply viewing a course page. You were entering an environment with logic, sequence, tools, and participation built into it.

A later CUNY / Queensborough Community College CourseInfo student help page shows the system in use through the CourseInfo Global Gateway. The page identifies course areas for Announcements, Course Information, Staff Information, Course Documents, Assignments, Communication, External Links, and Student Tools. Course Documents included online handouts, lecture materials, and other course files. Student Tools included a drop box, calendar, web page tools, and a student manual. The drop box allowed students to browse a local hard drive or floppy disk and upload a file into the course.

A practical replication model sat underneath that first system. In order to recreate the functionality we had built for one course site, we used independent scripts that could copy the template of one site and make another. That was one of the fundamental underpinnings of the first CourseInfo system: taking the assets, images, navigation, and scripted tools from a templatized model and replicating them each time someone wanted a new course. In the beginning, that process was manual. Over time, we automated it through a create-course form and a copy capability. That gave us a single engine for creating multiple CourseSites.

This early 1.0 stage deserves attention because people tend to jump directly from primitive beginnings to the more mature system that came later. Teacher's Toolbox was the CourseInfo product name in this first product era. It was where much of the real learning happened. It was where we began to understand that the value was not simply in putting a course online, but in giving faculty a practical, repeatable set of tools for teaching in a digital environment. It was where CourseInfo began moving from expression to operation, from pages to functions, from presence to participation. In this first product era, we were already building an instructional operating environment.

Design discipline at the browser frontier

We worked in a flurry to create templates that would make this manageable for faculty. Part of the goal was practical and aesthetic. The early academic web was often a patchwork of text-based user experiences, brown backgrounds, pink links, construction-worker graphics, and inconsistent page layouts. In that environment, Teacher's Toolbox was an anomaly. We were sensitive to the user experience from the beginning. Layout, color, placement, graphical buttons, headers, and icons all mattered because they helped turn the web from a collection of links into something that felt like a real interactive interface. Others were often using links to do the work. We were trying to use the emerging visual language of the browser itself to make the system understandable, navigable, and credible. That shaped how faculty experienced the product and how the market began to perceive what an online academic system could look like.

Our approach to the interface was also about reducing friction for inexperienced users. Most faculty were not web developers, and many were only beginning to understand what the browser could do. We could not assume technical confidence. The product had to make the next step feel obvious. Buttons, navigation, icons, layout, upload workflows, and course tools all had to work together so that a faculty member could move through the system without feeling exposed by the technology. The goal was not simply to make the system look better. It was to make participation feel possible.

That focus on usability also led us to think early about support. We wanted interactivity at the most basic level, not only inside the course tools, but also in the way faculty might be guided through the system. At one point, the team even began exploring our own version of something like Microsoft Bob, the mid-1990s Microsoft interface that used rooms, familiar objects, and animated characters to guide users through applications. The idea was interesting because it treated help and navigation as part of the experience rather than as something separate from it. But the concept and the technology were too early at the time. The web was not ready for that kind of guided interface, and neither were most users or institutions. Still, the fact that we were even exploring it says something about how we thought. We were not only building pages. We were thinking about usability, guidance, support, and interaction from the beginning.

HTTP upload and the additive web

There was also a very practical production side to that design sensitivity. We had to create what was almost a button factory. Each menu item on the left-hand navigation required a full set of complementary images. Every button state had to work visually with the rest of the interface. At one point, we had something like thirty sets of buttons, all meticulously created by Tim. That work was not decorative. It was part of how the product communicated structure. The buttons, headers, icons, and navigation gave users cues. They helped faculty understand where they were, what they could do next, and how the system fit together.

The deeper goal was to lower the barrier to participation and make the web feel usable rather than intimidating. This was still the early browser era, when Netscape was the dominant environment and the web itself felt raw, unstable, and full of possibility. At times, the tools were simply not sophisticated enough for what we were trying to do. One of the real breakthroughs came when Dan began working with mSQL, which helped push the work toward a real database-driven product. From there, the database layer continued to evolve as newer tools became available. Around that same time, we saw the power of HTTP file upload: the ability to send a file to a server, store its reference in a database, and retrieve it later through the web. Today that sounds routine. At the time, it felt almost magical.

That is one reason the HTTP upload concept was so important. On the surface, it was a technical capability. In reality, it was a bridge in human terms. I have often said that people do not really fear change; they fear loss. They resist what feels subtractive — what threatens to take away familiarity, competence, or control. But they are much more open to what feels additive. HTTP upload made the web feel additive. A faculty member could take something they already knew — a syllabus, a handout, a document — and place it into this new environment without having to become a programmer or abandon the way they already worked. It built confidence by breaking the barrier of acceptance through a simple internal realization: I can do this. And once faculty began to feel that, the effect spread. People talked to one another. They showed peers what they had done. A quiet wave of confidence began to move outward through the institution, because once one person proved it was possible, others could imagine themselves doing it too.

That is why the feature was so powerful. It was not just a piece of engineering. It created reassurance, and then it created momentum. It gave faculty a way to step into the future without feeling that they had to surrender themselves to it first. And that, in many ways, was one of the deepest patterns in the whole early life of CourseInfo: when change felt additive, people leaned in. When they believed they could do it, the culture around them began to shift as well.

By October 1997, CourseInfo had already grown well beyond a college campus experiment. The company had moved from a room in Dan's Collegetown house into the Student Agencies building on College Avenue. It already had at least twenty-five Cornell courses using the service. And by that point, the product already supported announcements, documents, assignments, communication tools, discussion boards, surveys, and quizzes while sparing faculty from needing HTML knowledge. Later Cornell accounts would remember just how quickly that growth took hold. What mattered to us at the time was that the Teacher's Toolbox idea was no longer theoretical. It was already taking hold in the real life of courses and institutions.

Teacher's Toolbox was the first CourseInfo product era. It proved that faculty would use web-based tools when those tools were useful, understandable, and additive to the way they already worked. But its success also exposed the limits of the first model. The more courses we supported, the more obvious it became that individual course sites, separate usernames, separate passwords, and isolated administration would not work at institutional scale. That realization led to the next era: the Interactive Learning Network.

From Teacher's Toolbox to the Interactive Learning Network

The Interactive Learning Network began as our answer to the institutional limits of Teacher's Toolbox. At first, building courses individually had made sense. But once the number of courses started to grow, the limits of that first model became impossible to ignore. Working with Cornell Information Technologies, or CIT, we began to understand just how unmanageable separate course sites with separate usernames and passwords would become. What had seemed workable at the level of a single course began to break down at the level of the institution. We realized we had a structural problem: our first version did not have a central core built to handle common authentication, shared identity, and administration at scale.

That realization forced us to rethink the architecture. In effect, we had to set aside the first version and build toward something much more coherent. Out of that shift came what we affectionately called Version 1.5: the Interactive Learning Network, or ILN. The name reflected a real evolution in our thinking. Teacher's Toolbox had been the first expression of CourseInfo as a product. ILN was the first expression of it as an institutional system. We were no longer focused on isolated course websites or individual course tools. We were beginning to envision a connected academic environment inside the institution itself, capable of supporting not just one course at a time, but a network of courses across the academic environment.

At its core, it was what would later be recognized as a course management system, though at the time that language was not yet fully settled, either in the industry or even in our own minds. A course management system was, at its simplest, a shared online environment for course content, communication, assessment, administration, and student access. What mattered to us was that the idea had clearly grown beyond the first version. We were now trying to build a shared institutional framework for teaching and learning online.

Naming the category

As ILN took shape, I also began to understand that we needed language for what we had built. That was where those same three parts of me came together again. The business side understood that categories matter. The technical side understood that the product had evolved beyond individual course pages. And the sales-and-marketing side understood that if we could name the thing clearly, and describe it in language the market could understand, we could help the market see what it was. That was part of why I began describing it as a course management system. I was not just helping shape the product. I was also helping to shape the words that would carry it into the world.

Public references from late 1997 and 1998 show that this language was beginning to settle around the work CourseInfo had already been doing. In December 1997, I was quoted describing CourseInfo as a "Web course-management tool." By 1998, CourseInfo was being described publicly as a course management system. The category was being named around a product and operating model that had already moved beyond individual course websites.

This was not just the role I played in the founding years of CourseInfo. It was, in many ways, the role I continued as the company grew. I was the primary lead on those efforts, with the core of my work centered on corporate strategy — the business of the company — and product strategy, the work of helping manifest the product the market actually needed. I brought that combined perspective to the management table: how to shape the business, how to shape the product, and how to help the market understand the connection between the two.

Communication as the heart of the system

The Teacher's Toolbox did not disappear in that shift; it evolved. The generators, templates, and course-level capabilities we had been building individually now began to take their place inside a broader institutional framework. ILN represented that next level of work: not a single course, but a network of courses; not just content pages, but content, communication, and assessment working together; not just isolated utility, but a system designed to function at the enterprise level.

Communication became especially important because the web itself was still embryonic. One of the clearest early patterns on the web was community. People were dialing up not only to retrieve information, but to join discussion-board-powered communities where they could ask questions, share ideas, and participate in conversations that continued beyond a single moment. We understood that pattern and brought it into the structure of every course. The same kind of persistent discussion that was beginning to define early web communities could also exist between students and teachers inside an academic course. Discussion board technology became the communication heart of online learning. It gave students and faculty a way to continue the conversation outside the classroom, not in real time necessarily, but in a persistent space connected to the course. That asynchronous quality mattered. Students could post and reply at their own pace. They could reflect, research, and compose a response instead of being limited to the speed of an in-class exchange. It also created a different kind of community. In an online or hybrid course, the discussion board could become the primary place where students interacted with one another, reducing the isolation that could come with learning at a distance. It gave a voice to students who might not be the first to speak in a physical classroom. It made participation broader, more visible, and more inclusive.

Morehead State, a server, and a snowstorm

At the same time, we were also watching and evaluating chat technologies. That made sense in the period we were living through. ICQ had launched in 1996 and helped define the early instant messaging era. AOL Instant Messenger, MSN Messenger, and other services would push online chat even further into popular use. Those patterns mattered because they showed that communication on the internet was not going to remain limited to publishing pages. It was becoming interactive, social, persistent, and immediate. The world was also using PHP for web development, and we were assembling every tool we could find to make the Interactive Learning Network exactly that: interactive. In many ways, we were like kids in a candy store, evaluating new concepts as they appeared and figuring out how they might fit into our content, communication, and assessment strategy. ILN needed to carry that same direction into the academic environment.

One of my clearest memories of that early ILN period was Morehead State University becoming a client. We had completed the sale, but at that point we had not yet created formal install scripts for the ILN system. The team had to figure out how to move from one working installation to another. In practical terms, that meant developing a script that could do something close to a system copy. We bought a server, and LJ created a crossover cable so we could copy one system to the other. I suppose, in retrospect, that was one of our first real installs.

Once the system was copied, we organized a trip to Morehead State University and brought the server with us. The plan was straightforward in concept and primitive in execution: carry the server to campus, plug it into their network, and make sure it connected. Today someone might call that a network appliance. At the time, we were simply trying to figure out how to get our system connected to a campus network in a way that would actually work.

Dan and I took the server on the plane with us and ended up on the Morehead State campus in the middle of a snowstorm. No one was on campus. I mean no one. We were in contact with the MSU team, and they gave us directions to the student union, where there were a few dorm rooms we could use. Our transport got us to campus in the snow. We found the server room, plugged in the server, and made sure it was connected, which took us about fifteen minutes. Then Dan and I spent two days on the MSU campus waiting out the storm until we could be picked up for our return flights. We never saw a soul during that event, but our new client was happy. It was early, imperfect, resourceful, and completely real. That was what enterprise software implementation looked like for us at that stage: a server on a plane, a crossover cable, a campus network, a snowstorm, and a team determined to make the system work.

Morehead State made the institutional reality visible. ILN was no longer only software we had built. It was something we had to install, connect, support, and make real inside another university's infrastructure.

A category forming around us

Once we reached the Interactive Learning Network stage, CourseInfo was no longer just solving a Cornell problem. We were operating inside a category that was beginning to form around us.

Our focus on user interface and user experience also set us apart from many of the people trying to do something with learning online. As we continued to develop the Interactive Learning Network, we began to see other systems and projects appear, most of them still emerging from academic or institutional environments. The category had not yet fully stabilized. Different teams were trying to solve different parts of the problem: course websites, course delivery, communication, assessment, content management, standards, interoperability, and institutional scale.

WebCT was one of the important early efforts in that landscape. Murray Goldberg had begun the underlying work at the University of British Columbia in 1995, and WebCT was first presented publicly at the Fifth International World Wide Web Conference in Paris in May 1996. After that presentation, WebCT entered a free distribution phase. In 1997, Goldberg co-founded WebCT Educational Technologies Corporation as a University of British Columbia spinoff to sell and support the software commercially. WebCT was visible publicly in 1996, and its move from university research project to market-available commercial product came in 1997.

Lotus LearningSpace was another early system in that same emerging category, with commercial availability in 1997. TopClass, from WBT Systems, was also commercially available in 1997. Web Course in a Box also belonged in this timeline. It originated at Virginia Commonwealth University as a template-based course-web tool in the mid-1990s, was licensed to madDuck Technologies in 1997, and was commercially visible in the courseware market by 1998. Each of these systems reflected a different part of what the market was trying to understand. Some emphasized course delivery. Some emphasized template-based course publishing. Some came from universities. Some came through commercial software channels. The common signal was that higher education was beginning to recognize the need for structured online learning environments, but the category itself was still fragmented.

Moodle came later. Martin Dougiamas began trialing early prototypes in 1999. The first Moodle site appeared in 2001. Moodle 1.0 was released on August 20, 2002. Moodle became enormously important later, but those dates place it outside the first wave of CourseInfo's primary 1996 and 1997 activity at Cornell. The distinction keeps the historical sequence clear. Moodle was not part of the immediate early competitive moment we were living through at Cornell. It belongs to the next stage of the category's development.

The NLII and IMS timelines also sit in the same narrow window as CourseInfo's early work, but their role was different. EDUCAUSE's own history says the National Learning Infrastructure Initiative was outlined in 1993 and announced in 1994, and that work began on the Instructional Management System in 1996. IMS Global's history places IMS as the Instructional Management System project within EDUCAUSE's National Learning Infrastructure Initiative in 1997. Those efforts were aimed at the standards and interoperability problems that early systems like ours were making visible. Educational content, tools, assessments, and learning-system components could not easily move or work across platforms. That interoperability problem was not abstract. It was a direct result of the kind of work teams like CourseInfo were already doing: building real systems, with real tools, for real institutions, in a market where common technical standards did not yet exist. The field was beginning to recognize that online learning systems could not remain isolated, proprietary islands forever.

The commercialization dates reinforce the point. By late 1996 and through 1997, CourseInfo was already building, selling, integrating, and supporting a working online course system at real academic institutions. WebCT moved from public university research into commercial form in 1997. Lotus LearningSpace and TopClass were commercially available in 1997. Web Course in a Box moved from its Virginia Commonwealth University origins into the commercial courseware market in 1997 and 1998. Moodle came later, with early prototypes in 1999, the first Moodle site in 2001, and Moodle 1.0 released on August 20, 2002. CourseInfo was already in the market with customers, enterprise integrations, and a working product while the category and its commercial shape were still forming.

The broader activity shows how early this work really was. This little CourseInfo team at Cornell was not waiting for a mature category to form. We were already in the heat of it, powered by our own intuition as a collection of students and technologists working to solve a problem we were living ourselves. CourseInfo's place in the timeline was not that we were watching the course management system category form from the outside. We were one of the teams actively forming it.

Ithaca Commons as the next stage

After the rest of the team graduated, we moved from the Student Agencies offices to the Ithaca Commons. That move marked another transition in the life of CourseInfo — from something still partially sheltered by the Cornell environment to something that was now trying to find its footing as a real company beyond campus. We had graduated. The entrepreneurial infrastructure that exists at Cornell today was still barely there in the form we would have needed it. And from the Ithaca Commons, we were trying to decide what came next. Could Ithaca still hold the company? Did we need to move into a stronger ecosystem? Were New York City, Long Island, or Washington, D.C. more realistic next environments for the kind of growth we were seeking? That was the setting in which the next decisions began to take shape.

Another story from that period captures the operating reality of those days. My dad was working at Morgan Stanley Dean Witter at the time, and they were closing their Rochester office. I asked him if there might be any office furniture we could have. With permission from the local firm lead, the answer came back that all the desks needed to go. That sounded like a gift until we got there and saw why they were willing to let them go. Those desks were absolute beasts — heavy steel things that felt like lead weights. No wonder they were happy to see them leave. But a few of us made the trip to Rochester, loaded them up ourselves, drove them back to Ithaca, and filled our new Ithaca Commons office with them. We brought back enough for each of us. It was exactly the kind of team adventure that defined that stage of the company — resourceful, physical, a little absurd, and completely sincere. I believe one or two of the guys may still have either a whole desk or part of one somewhere even now.

Capital, distance, and "the Inter-what?"

By that point, the entrepreneurial system that exists at Cornell today was still almost non-existent in the form we would have needed while we were there. And by then, we had all graduated and knew we needed to move on. We were already looking beyond Ithaca — toward New York City, Long Island, and the Washington, D.C. corridor — for the kind of ecosystem that could better support what we were trying to build.

What we did not have was access to capital. In 1996 and 1997, Ithaca was not a place where an internet software company could easily raise money. Very few people around us seemed to understand what the internet was about to become. That was the missing ingredient. It was not that we lacked the product, the value proposition, or the makings of a successful business. It was that we were building an internet company in a place and at a time when the local capital environment was not yet prepared to see what we were building. CourseInfo was being built in a pre-internet, pre-dot-com moment, which was part of why the product was ahead of the capital environment around it.

Dan and I still laugh about one conversation we had with a potential investor in Ithaca. We had gone through our pitch, trying to explain what we saw coming and why the internet mattered. When we finished, the investor looked at us and said, in effect, that we should forget the whole internet thing because it was not going to work. Then he pointed instead to a set of little black boxes and began explaining why that was the real opportunity. The story stayed with us because it captured the moment. It was not just that raising money in Ithaca was difficult. It was that many people around us simply did not yet understand what the internet was, what it was becoming, or why it mattered. At the time, it was a revealing reminder of how early we really were.

Honoring what came after, focusing on what came first

In telling this story, I want to be clear about what it is and what it is not. It is not an effort to diminish what came later with Blackboard Inc., and it is not a denial of the larger Blackboard brethren family that grew from those years and after. I still hold deep appreciation for that broader story and for the people who were part of it. The entire CourseInfo team were extraordinarily talented in their own right, and that talent did not stop at the edge of the Cornell years. It carried forward into the next chapter as we moved into Blackboard Inc., where a broader Blackboard brethren family began to form around the work. That world, too, included talented people, important contributions, and relationships I still value deeply — including Matt and Mike and many others whose part in that larger story deserves its own telling another time. This chapter is simply focused on the Cornell and CourseInfo lineage, not because what came after matters less, but because the earlier story deserves to be told clearly in its own right. In many ways, it is also being fueled by our most recent time together and by the reflection that came from hearing those stories told again, all of us looking back from where life has since carried us.

In that sense, the next-step conversation did not create our desire to leave Ithaca. It met us at a moment when, as a team, we were already looking for the next environment in which the work could grow.

Product validated, capital missing

By 1998, the question was no longer whether CourseInfo had created value. The question was where that value could be financed, scaled, and carried into a national market. CourseInfo had already created something real. We had working software. We had real customers. We had institutions using the product. The product had moved from individual course websites and faculty tools into an institutional platform. The Interactive Learning Network showed that CourseInfo was no longer just a set of course website generators. It was becoming a course-management software company before the market language had fully settled. We also understood what made part of our system unique. CourseInfo introduced a what-you-see-is-what-you-get authoring capability that allowed faculty to modify course materials on the fly. That was a huge differentiator. It directly met the needs of the market because faculty did not want to depend on programmers or technical staff every time they needed to change course content. We were also already working on how to import content more easily into the system so we could reduce the level of service required to get institutions up and running. We understood that enterprise software could not depend on handholding every course into existence. It had to scale. It had to make adoption easier for faculty and administration. It had to meet institutional needs, not just individual instructor needs. We were keenly aware of that. CourseInfo had the product direction, the early customers, the institutional use case, and the market insight. What we needed next was rocket fuel. Over the course of 1997, the system was already running at Cornell University, Yale Medical School, the University of Pittsburgh, and across a broader group of institutions that, in our early accounting, brought the total to fifteen. We had crossed a threshold. The system was no longer merely an interesting campus tool. It was proving that it could function in real institutional settings.

In many ways, we existed in a bubble. Inside Cornell and Ithaca, we had many of the components needed to build the company. We had technical talent. We had product insight. We had institutional access. We had faculty feedback. We had early customers. We had the beginnings of a category forming around us. CourseInfo had become an enterprise-level company with an enterprise-level product, one capable of supporting content, communication, assessment, authentication, and institutional scale. We also had the essential ingredients of a real business: working technology, early customers, institutional integrations, and a business model that made sense. What we did not have were the capital relationships. That was the constraint. We knew we needed capital. We knew we needed to move fast. Ithaca had helped us see the problem and build the product, but it was not the easiest place to finance an internet software company in 1998. When we spoke to some investors, they would respond with versions of, "The Inter... what?" That reaction captured the gap between what we were building and what the local capital environment was ready to understand.

Part of our activity at the time was also driven by conversations we were beginning to have outside the university market. We were already doing outreach to industry publishers about what we had developed. I clearly remember a conversation with a senior executive at Thomson Publishing who told us that we were building the next generation of technology and that what we were doing was extremely valuable. That stayed with us. It was one of the first times a large outside party had validated our thinking. I remember us all going out to a local pub afterward to celebrate. It gave us another signal that CourseInfo was not just solving a local Cornell problem. The work had broader value.

Outreach, validation, and looking outward

From the Ithaca Commons, we were already looking beyond Ithaca. We were traveling to different cities, meeting with investors, and trying to understand where CourseInfo could find the capital relationships, business networks, and market visibility needed for the next stage. New York City, Long Island, Washington, D.C., and Boston were all part of the broader conversation. Each represented a different possible path. None of this was predetermined. We were evaluating options, testing assumptions, and trying to make a conscious decision as a team about where CourseInfo could move fast enough to match the opportunity in front of us.

The later S-1 record reflected that foundation. It described the first software product as an online learning application developed at Cornell University. It also described the CourseInfo technology as an internal online learning system used by faculty at Cornell, which had begun being marketed to universities and school districts in the United States and Canada. By the end of 1998, the company had approximately 26 licenses of one software application. That later public record confirmed what we already knew from inside the work: CourseInfo had brought the product base, the implementation experience, the early customer foundation, and the institutional use case into the next stage.

In early 1998, we were first exposed to a standards-type conversation on a call with a potential client. As the call continued, the conversation turned to how courses might be imported and exported, and what that could mean for an institution. They told me there was a small company out of Washington, D.C. that was trying to help move the standards-based conversation along. As always, we did our research after the call and discovered a very small company in D.C. that was working on the standards initiative on behalf of NLII and IMS. That company was Blackboard LLC. We thought very little of it at the time and continued to focus on our work.

During that same period, we sent Dan to an adaptive testing conference to explore a possible funding opportunity. The conference was centered around an adaptive testing grant and was looking for companies that could execute against it. We thought it was a strong opportunity to extend what CourseInfo was already doing further into assessments and potentially capture the funding to go with it. While there, by happenstance, Dan bumped into a few members of that team who recognized CourseInfo and were aware of our leadership position in the market. This was our first real introduction.

The conversation piqued our interest because they were working under contract on standards for online learning. They were thinking about what a standards-based platform could mean, and that was interesting to us. It connected to the import-export questions we had already heard from the market, even though our primary focus remained on building, selling, and supporting CourseInfo.

They also mentioned that they were working on a prototype for schools. We largely dismissed that part of the conversation because CourseInfo already had a working and highly functional product in the space, one that clients were paying for and expecting us to continue expanding. We were not evaluating them because they had a product we needed. What caught our attention was the standards conversation, the D.C. network, and the possibility that there might be a broader strategic path worth exploring.

By the time the next-step conversation began, CourseInfo had already moved well beyond an idea. The company had a working platform, more than a dozen customers, institutional integrations, implementation experience, a business model, and clear signs of product-market fit. The question was no longer whether CourseInfo could succeed. It was how fast it could move and what environment would let the momentum continue.

That was the decision the team had to make together. CourseInfo could have continued forward on its own, but doing so from Ithaca would likely have taken longer than the opportunity in front of us allowed. The category was still forming, and our early lead mattered. We wanted speed to market, capitalization, and a more resourced environment. The discussion was not casual, and it was not automatic. We were looking at what had been built and weighing which path gave the product, the team, and the market opportunity the best chance to move quickly. We knew we needed to accelerate our efforts and that we were at a pivot point where we needed capital to multiply the efforts against what we had already achieved.

The Blackboard LLC opportunity became the path we chose because it gave CourseInfo's working platform and market traction a broader frame. Blackboard LLC brought a standards story, a Washington, D.C. location, and a capital-facing narrative that could help move the company into a larger national market.

Directly upon that combination, the new company, Blackboard Inc., received its first capital funding. Blackboard LLC would not have received that funding without a working product, and CourseInfo brought that product into the combination. From that point forward, CourseInfo became the foundation for Blackboard Inc., and the company's future funding was built on the success of the product and platform CourseInfo had created. After the combination, Dan and I moved onto the management team while the rest of the CourseInfo team members took on divisional operating roles inside the new company. Once the teams came together, much of the operating center of gravity shifted toward the CourseInfo team and the work we had already been doing, including sales and marketing, product development, support, and implementation. In many ways, CourseInfo became the heart and soul of what was now Blackboard Inc. From my own vantage point, I remained deeply engaged in the corporate and product strategy work that helped shape what came next.

From the CourseInfo side, the combination was understood as a merger. That was how it was explained to us, and that was part of how the team was brought into the decision. The later public label of "acquisition" served a different purpose. It simplified the outside narrative and helped position the company for investors as a high-growth entity in a market that was beginning to open.

That public version was cleaner, but it was not the full lived experience. Inside the work, we understood the combination as the joining of what each side brought to the table. The next generation of the business worked because CourseInfo brought a real product, paying customers, a working business model, and a team that had already learned how to implement and operate in the market, while Blackboard LLC brought standards alignment, working capital, a new ecosystem, and prestige in Washington, D.C.

The public story became easier to repeat. The lived version was more exacting, and more earned.

Part of what brings all of this back to me so vividly now is that I recently had the chance to see much of it again, not as memory alone, but in living form. A few weeks ago, my dear friend Dan Cane received Cornell's 2026 Entrepreneur of the Year award, in recognition of the full arc of his work — from CourseInfo and Blackboard to Modernizing Medicine. As part of that event, Dan invited the entire team back to celebrate with him. It was not just an award ceremony. It was a reunion with the very people who had lived that early story together. To see the team again, in that setting, was to feel once more the energy of what had begun in those Cornell years. It brought back not only the work itself, but the atmosphere around it — the belief, the improvisation, the ambition, the uncertainty, the loyalty, and the sense that we were all part of something larger than we could fully name at the time.

That experience is part of what has driven this period of historical reflection for me. It has made me want to give credit where credit is due, and to do so with real appreciation for the people who built that story together. Over time, history tends to simplify. It pulls a few names forward, flattens the supporting structure, and turns lived collaboration into a cleaner public narrative than it ever really was. Seeing the team again reminded me how much of the real story lives elsewhere — in the people who were there, in the work they did, in the risks they took, in the hours they gave, and in the way their lives continued to carry that early momentum forward long after CourseInfo itself had changed form.

Dan likes to say that lightning does not often strike twice, but in our case it did. I would go one step further: in our case, lightning struck many times. What began at Cornell and in CourseInfo kept expressing itself through the people who had built it. The later paths differed, but the pattern was shared: we kept finding complex markets, building platforms, and carrying that early momentum into new chapters.

In that sense, this too is part of the Cornell story. What happened there was not a single flash of entrepreneurial success tied to one company and one moment. It was the beginning of a pattern. It was the beginning of a group of people learning, almost in real time, what it meant to build, to trust one another, to recover from uncertainty, and to carry hard-won momentum from one chapter into the next.

A promise we made each other

One of the clearest signs of what CourseInfo was can be seen in where we went afterward. When the CourseInfo team decided to merge with Blackboard LLC, I remember that we made each other a promise. CourseInfo would only be our first company. We told each other that we would go on to build others. That was not bravado as much as it was a statement of how we understood ourselves at the time. We did not see the merger as the end of the entrepreneurial story. We saw it as the completion of one chapter and the beginning of others.

The later paths of the CourseInfo team grew from the same pattern. The company was small, but the talent density was extraordinary. The same instincts that shaped CourseInfo — product thinking, technical execution, market translation, institutional understanding, operational discipline, and entrepreneurial nerve — continued to show up in the work we each went on to do. The early CourseInfo team did not simply build one company and disappear into the larger Blackboard narrative. We kept building.

Where the team landed

For my own part, I continued working at the intersection of education, technology, governance, entrepreneurship, and platform strategy. Through Gilfus Education Group and other ventures, I kept returning to the same kind of work that had shaped CourseInfo: helping institutions understand emerging technology, translating product ideas into market structure, and building strategy around education innovation, cybersecurity, AI, safety, risk, and institutional transformation. I also serve on the ISACA Board of Directors, where that work now extends into governance, digital trust, cybersecurity, AI governance, and enterprise risk. Today, I find myself working at the intersection of AI, cybersecurity, digital trust, innovation, entrepreneurship, vibe coding, and online learning. The terrain has changed, but the pattern is familiar. These forces are reshaping how people live, learn, work, build, and govern institutions. Much of my work now sits in that space: helping organizations understand what is changing, modernize legacy processes, design practical solutions, and make better decisions about the systems they will need for the next decade.

Dan Cane carried the same entrepreneurial pattern into healthcare technology. After CourseInfo and Blackboard, he went on to co-found Modernizing Medicine, now ModMed, where he serves as co-CEO and co-founder. ModMed's work in specialty-specific healthcare technology, electronic health records, practice management, patient engagement, and related software reflects a familiar pattern: listen closely to how professionals actually work, identify the broken workflow, and build software around the real operating patterns of the field. Cornell named Dan the 2026 Cornell Entrepreneur of the Year, recognizing an arc that began with CourseInfo and Blackboard and continued through his work building ModMed. The environment changed from higher education to healthcare, but the underlying instinct remained familiar.

Tim Chi carried the CourseInfo lineage into the consumer marketplace through WeddingWire and The Knot Worldwide. The Knot Worldwide describes him as a former CEO and current board member, and its company history places the 2018 merger of WeddingWire and XO Group as the formation of The Knot Worldwide. Tim's later account of WeddingWire describes the risk of leaving Blackboard, building at night and on weekends, and turning a domain he could afford into a major platform company. That feels very familiar to the CourseInfo story. Tim took another fragmented, high-friction market — wedding planning — and helped turn it into a platform category where discovery, vendor connection, planning tools, and consumer experience could operate at scale.

Lee Wang also carried that pattern into the WeddingWire story and beyond. Cloudforce's 2025 announcement identifies Lee as co-founder of WeddingWire, President and COO, and later as a leader of the combined company after WeddingWire merged with XO Group, the parent of The Knot and The Bump, creating The Knot Worldwide. The announcement also named him President and Chief Revenue Officer of Cloudforce. Lee's path reflects the operating and scaling side of the CourseInfo lineage. CourseInfo had required more than an idea; it required sales, operations, customers, systems, and institutional trust. WeddingWire required the same kind of discipline in a different market. Lee's later work shows the continuation of that skill set: building and scaling companies where technology, customer acquisition, operations, and market structure have to come together.

John Yang carried forward the technical infrastructure side of that lineage. His later work sits squarely inside the same operating pattern: the technical leadership required to keep platforms reliable as user activity, transactions, integrations, and organizational complexity grow. In the CourseInfo years, that kind of work was easy to overlook from the outside. In practice, it was central. Products that serve institutions and markets only become real when the infrastructure keeps working.

Stephano Kim went on to a career at the intersection of strategy, media, advertising, data, operations, and technology. Fox Corporation announced in February 2025 that Stephano had joined as Chief Strategy and Operations Officer, Advertising Sales, a newly created role overseeing advertising sales strategy, solutions, platform partnerships, and operations. Related coverage described his prior senior strategy and data roles at AT&T and WarnerMedia, including work tied to Turner Broadcasting, corporate strategy, data strategy, and broader media operations. In the CourseInfo story, Stephano represented the strategic and financial side of the early team. His later work shows that same orientation at a much larger scale: connecting strategy, operations, data, platforms, and market execution inside complex media organizations.

CourseInfo as a proving ground

Taken together, those later paths show that CourseInfo was not only early because of what we built. It was early because of the people it gathered. It became a proving ground for a group of Cornell students who went on to build, lead, advise, govern, and scale organizations across education, healthcare, weddings and events, media, governance, cybersecurity, AI, and enterprise technology. We told each other CourseInfo would only be the first company. In different ways, that is exactly what happened.

The smaller beginnings

When I think back on that history now, I think first about the smaller beginnings: the classroom, the student organization, the advisory council, the multipurpose room, the walk downtown to form an LLC, the streets of Collegetown, the summer in Ithaca, the conversations with faculty and administrators, and the habit of listening carefully enough to hear the problem underneath the stated problem.

That is where the real history lives.

Cornell and CourseInfo did more than launch a company. They revealed the role I would keep playing for decades after: working at the intersection of business strategy, product strategy, and the language that helps people understand what a new technology is becoming.

Be there in the first few years

Over the years, I have mentored and coached hundreds of entrepreneurs, and I often tell them the same thing. If you really want to start something, shape it, and create something that is yours, you need to be there in the first few years of the business, when it is still forming. That is when the work is most direct. Ideas become products and services. Customer and market interactions begin to shape what the business can become. Processes, procedures, habits, and operating patterns start to form around the people doing the work. Those early years leave an imprint on the company, and they leave an imprint on the people who build it.

After those first years, the work changes. You can still refine the company. You can still build it, strengthen it, and help it grow. But by then you are often working from something that already has its original shape. The work becomes more derivative, more a matter of successive refinements than original invention. That does not make it unimportant, but it is not the same as being there when the idea is still being formed into something real, tangible, and workable. Once you help bring something into the world, it remains yours in a way that later work never fully can.

That was the CourseInfo experience for us. The team was there when the company, the product, the operating model, and the category language were still forming. We were not only refining something that already existed. We were helping manifest the thing itself. That experience became part of how we each learned to build, and it is part of what each CourseInfo team member continues to carry into the companies, platforms, organizations, and future activities that follow.

Smithsonian, Cornell, and a quiet coincidence

As I put together this memoir, I was doing research on the fact that in 2000, Blackboard, Inc. appeared in the Computer World Smithsonian Awards collection in the Education category. I remember it vividly. As I recall, after we received it, some of us walked around the office with the award medal hanging around our necks. In a strange twist of irony, I also discovered that Cornell University appeared separately that year through the Cornell Theory Center and its Advanced Cluster Computing Consortium work on the Velocity cluster. Coincidental? I think not. Apropos? Absolutely.

Quiet beginnings

Before there was a recognized market, before there was a company the world would remember, there were just a few of us trying to make sense of a change that was arriving inside higher education. We were close enough to the problem to see what was coming, even if not yet in its final form. And like many ideas that later seem obvious in retrospect, it began not in a grand arena, but in small rooms, with small groups, and with people who were willing to listen carefully enough to hear the future beginning to speak. CourseInfo's place in the history of online learning is not as a footnote to what came later. It is part of the beginning of the category itself.