Osman Rashid had the customers. Now he needed the books.

The students wanted the books. This was encouraging, right up to the moment Osman Rashid had to buy them. In Chegg’s early rental experiment, an order could arrive before the company owned the textbook it had promised to deliver. The team would find a copy online, pay for it and send it directly to the student. A business that would become known for orange boxes began with a rather less photogenic asset: its co-founder’s credit card.

There is a particular kind of satisfaction in discovering that people want your product, followed by a particular kind of alarm when they want more of it than you can afford. Rashid and his colleagues had reached both stages. They were learning retail, customer service and logistics while taking orders. The syllabus had arrived after the exam.

“We have no idea how to run a warehouse,” he recalled. That admission belongs near the beginning of his story. Chegg’s founding CEO would go on to build digital textbooks, science games and schools. But his career is easier to understand from the point at which a student needed a book and somebody had to work out how to get it there.

A bookstore grievance travels well

Rashid was born in London, where his father’s work for Pakistan’s Foreign Ministry had taken the family. His childhood included Ghana and Pakistan; Islamabad was where he completed his later schooling. He attended Islamabad College for Boys before moving to the United States in 1989 to study electrical engineering at the University of Minnesota. He graduated in 1993.

The engineer’s education came with a second course in student economics. Textbooks were expensive to buy, disappointing to sell back and liable to reappear on the bookstore shelf at a price that made the whole transaction feel like a practical joke. Years later, the memory still supplied the emotional logic for Chegg. He understood the customer’s irritation because he had paid for the privilege.

His early work crossed the line between technology and commerce. Product management led into marketing and business development at ATIO-related businesses, a customer-service venture called Gravitywell, and work at Chordiant. The sequence matters because the later education entrepreneur had spent years learning how products become businesses. An engineering degree was the beginning of that training, rather than its completion.

The customers had already voted

Chegg was incorporated in 2005, but textbook rental was a turn in the road. Its predecessor, Cheggpost, was a campus classifieds service, a place to trade the assorted necessities of student life. Books shared space with other transactions. The proposition was broad. The evidence of what students actually did was much narrower.

Facebook’s arrival in classifieds made the original business harder to defend. Rashid and investor Mike Maples discussed applying the Netflix rental model to textbooks. A student needed a book for a semester; owning it forever was incidental to the task. The experiment appeared under the wonderfully literal name Textbookflix. Nobody required a branding seminar to understand the offer.

Rashid remembers the team testing demand on campus and discovering more interested students than their tiny trial could accommodate. Success immediately raised an awkward question: how would they finance the inventory? Taking the order before purchasing the book gave them a way to learn what was wanted without filling a warehouse on speculation. His personal credit helped bridge the gap.

The method required an unglamorous collection of decisions: which titles to offer, where to find them, which suppliers could be trusted and how quickly a copy could reach a customer. Rental may sound like a simple verb. At national scale, it demands rather a lot of nouns: inventory, shipping labels, storage, software and money.

By January 2009, Chegg had already exceeded its revenue for the whole of 2008. That same year, Rashid received Ernst & Young’s Northern California Entrepreneur of the Year recognition in consumer products. The award was public; the mechanics behind it were mostly things a customer should never have to think about. A successful textbook delivery is a conspicuously uneventful occasion.

Keep the page numbers. Lose the paper.

Rashid’s tenure as Chegg’s CEO ended in early 2010. By then, another education project was under way. He and Babur Habib co-founded Kno in 2009, approaching the textbook from a different direction. Chegg had changed the transaction. Kno set out to change the object, and the things a student could do with it.

The original proposal included a large tablet with two screens. It was an understandable attempt to carry the familiar spread of an open book into a digital device. It was also a hardware business entering a market that Apple’s iPad was rapidly reshaping. Kno eventually licensed its hardware designs to Intel and concentrated on software.

In June 2011, its iPad app arrived with more than 70,000 digital textbooks. The useful details were deliberately familiar: page numbers, chapters and diagrams that matched the printed edition. A professor could still direct a class to the same page. Around that stable core, Kno added annotation, organization and ways to interact with the material.

That combination says something about the practical side of educational invention. Students and teachers already had routines. Making every routine obsolete would give them another assignment. Kno tried to preserve what made a textbook recognizable while taking advantage of what a screen could add. Intel acquired the company in November 2013.

A small question about gold

One of Rashid’s later ideas began at home. His young daughter asked where gold came from. He went looking for visual material to help explain it and came away dissatisfied. It is a pleasingly specific origin for an education company: a child asks a large question, an adult opens a browser, and the browser fails its interview.

Galxyz took shape around science as an adventure. Its Blue Apprentice game made learning part of a quest, with scientific ideas opening the way forward. The premise asked children to use concepts rather than merely recite information. It also treated their judgment about games seriously. A quiz wearing a space helmet would still have to earn its audience.

The project drew inspiration from his daughters and from his belief that children can learn more than adults sometimes expect. In public discussions of Galxyz, he challenged the assumption that an educational product could get away with being less enjoyable because it had good intentions. Children were perfectly capable of recognizing the bargain on offer.

Coming after two textbook businesses, a game might look like a departure. The recurring question was still access: how does an idea get from a page, a teacher or a parent into a learner’s understanding? A cheaper book addresses one obstacle. A digital edition addresses another. A child who wants to keep playing presents a different opening.

The classroom comes back into view

SOAR STEM Schools, founded in 2019, brought Rashid’s education work into Pakistani classrooms. The school network’s proposition combines science, technology, engineering and mathematics with concept-based learning. His co-founder, educator Dr. Shazia Khan, brought the classroom experience. Their partnership put a school builder beside a technology entrepreneur.

“Your number one challenge is always your team.”OSMAN RASHID

Affordability remained part of the stated purpose. Rashid has spoken about preparing children for the work they will encounter years later, and about reaching families beyond those who can buy an expensive education. Those are ambitions with consequences for staffing, fees and teaching. A school has to deliver them on an ordinary weekday, long after the launch announcement.

His next education role widened the circle. Khan Academy Pakistan launched in Karachi in December 2024 with Rashid as chairman and Zeeshan Hasan as CEO. Its work centers on bringing Khanmigo, Khan Academy’s AI tutor, into local education through curriculum alignment, teacher support and local implementation. The teacher is central to the plan.

The federal partnership’s scale is an ambition for a rollout, rather than a count of completed results. Training teachers is part of the agreement. It is a familiar complication in Rashid’s career: the useful idea needs an operating system around it, made of people, institutions and everyday habits as much as software.

A room with a different view

Education does not account for every project on his desk. At Convo, he moved from being a user to an investor and then bought out the founders. He now leads the enterprise collaboration company. It is another example of his interest in what happens between a product’s promise and the way people actually use it at work.

With his wife, Renee, he also co-founded Khoj Resorts in Pakistan. Their Shigar venture pairs hospitality with local craftsmanship and employment; a later announcement introduced Khoj Allana near Karachi. Mountains and beaches are a change of scenery from textbooks, though the work again depends on getting many practical details right for somebody else.

There is no need to make every undertaking fit one tidy theory. Some people like building several kinds of things. Rashid has said so plainly: “I mean, I love building things.” The remark makes the restless list of companies feel less mysterious. Finishing one project has rarely meant finishing with projects.

The thread worth keeping is his willingness to revise the means while staying interested in the person at the other end. A student wants a book for a semester. A child wants to know where gold comes from. A teacher needs something useful in tomorrow’s lesson. His career keeps returning to that point of contact, where an ambitious idea has to become a small, workable favor.