From Waterloo to Microsoft: An entrepreneur’s hustle

Sam Pasupalak was studying computer science at the University of Waterloo in 2008 when he found out that Bill Gates was delivering a talk on campus. Pasupalak didn’t have a ticket to the Microsoft chairman’s talk — but that didn’t stop him.

Pasupalak pulled off the first of many hustles that day by carrying T-shirts and bags so that he looked like a volunteer. He got past the event security to sit in the last remaining seat in the house.

Growing up in the small town of Bhubaneswar in eastern India, Pasupalak didn’t know anything about entrepreneurship, he was more interested in learning Sanskrit or playing cricket. After that talk, he was so inspired by Gates’ tremendous impact in the world, that he decided to start his own company as soon as he graduated. 

In 2010, he and his future business partner, Kaheer Suleman, built a piece of software for robots to understand natural human language commands in Chrysanne Di Marco’s class. He loved the freedom the class provided to build whatever students could imagine. The prototype he developed in that class became the basis of his future company. Between his computer science classes and co-op terms, Pasupalak’s excitement about programming and Artificial Intelligence (AI) grew.

At the time, not many people were talking about AI, but Pasupalak was dreaming about the future. With his best friend James Simpson, who was also studying computer science at Waterloo, Pasupalak drove to Carnegie Mellon University to show the prototype to a professor. The professor rejected the idea outright telling Pasupalak if he ever managed to build a real-world product with that technology, he would offer him a PhD in computer science.

In 2011, at the Velocity Garage, Pasupalak and his team continued work on the algorithms he developed in Di Marco’s class. Before Apple's Siri was publicly launched, they developed mobile search algorithms that allowed users to speak naturally into phones and get the information they wanted. Velocity set them up with everything Pasupalak needed to start thinking about building a business, which he named Maluuba. 

“We were razor focused on solving the problem of language understanding and we didn’t care if technology giants like Google or Facebook were pouring billions of dollars into developing this technology,” said Pasupalak. “We just wanted to be the best at any cost.” 

After graduating, Pasupalak had little money but didn’t take a job. While crashing on the couch of Iyinoluwa Aboyeji, another successful Waterloo entrepreneur, Simpson encouraged Pasupalak to take his passion to venture capitalists in Silicon Valley and raise funds for his company. Simpson even booked Pasupalak’s flight with $700 he had saved during his last co-op term.

Although hesitant, Pasupalak took the flight and hustled his way into a meeting with his first investor from Samsung Ventures. He also tried to meet with the business team of Yelp without a pre-arranged meeting. It led to security guards escorting Pasupalak out of the building. His persistence eventually paid off and Yelp became Maluuba’s first commercial partner. Then the next big hustle began. 

First, Maluuba won $25,000 at the Velocity Venture Fund in the fall of 2011. With $25,000, Maluuba developed training data and built a prototype to show investors. After graduating from the Velocity Garage, the company raised $2 million in seed funding from Samsung. During the first few years, Pasupalak and the team were rejected by hundreds of investors and almost went bankrupt three times. He never gave up hope and flew more than half a million miles hustling around the globe attending thousands of meetings, signing business deals and raising funds for his company.

The hustle paid off. By 2014, Maluuba had a Waterloo headquarters just across the street from campus. In 2015, Maluuba landed $9 million in Series A funding from a number of institutional investors and Maluuba’s language recognition technology had launched as personal assistants across more than 50 million Smart Phone and Smart TV devices worldwide, including partnerships with Samsung, LG, and BlackBerry. 

With even larger ambitions, Pasupalak became interested in extending the technology beyond personal assistants. He envisioned a world filled with intelligent machines capable of understanding and reasoning language just like humans. In 2015, before Montreal became a hot spot for AI, Maluuba strategically opened an office there for its research and development initiatives.

The research in Montreal helped the development of applications in Waterloo, where they continued to refine dialogue understanding, machine-reading comprehension, and some human capabilities like common-sense reasoning and memory. Unlike the closed operating systems and apps for some smartphones, Maluuba released huge datasets and research to other AI developers, and worked with researchers at University of Montreal.

“We believed in making AI more open and accessible to the community worldwide,” said Pasupalak. “Advances can be made more quickly in the field when the community at large works together and shares the knowledge.”

Pasupalak credits his passion and colleagues like Simpson for getting him over numerous obstacles. It paid off when Microsoft purchased Maluuba and the entire 50-person team for an undisclosed amount in 2017.

“Maluuba was my baby - from an idea in Velocity to building one of the top AI startups to being acquired by one of the largest technology companies in the world was quite the adventure,” said Pasupalak. “It required a tremendous amount of guts, determination, perseverance, and 80-100 hours a week most weeks for a period of six years. I would say a little bit of luck too. We had to believe that there was definitely light at the end of the tunnel, and even if there wasn’t, we had to create it ourselves.” 

The sale meant that he could take time off to realize some of his other passions, like climbing Mount Kilimanjaro, studying world history, and doing social service in India. It also meant he could give back to the University of Waterloo - the place that inspired him to be an entrepreneur. His $500,000 gift will provide a scholarship for the Computational Rhetoric lab, the Robotics lab, support for research by Di Marco in computational rhetoric, Velocity awards for computer science capstone projects, a graduate student startup award, a scholarship with a focus on AI through the Women in Computer Science (WICS) group, an AI Fellowship for Kate Larson and the AI Lab renovation. 

“I would never be where I am today if it weren’t for the University of Waterloo,” explained Pasupalak. “I have travelled around the world and gained a wide variety of experiences, but I am indebted to Waterloo for making me who I am today.”

It’s not lost on Pasupalak that the man he admires – Bill Gates – is also a philanthropist. It wasn’t until he sold Maluuba to Microsoft that Pasupalak met Gates in person. It was an opportunity of a lifetime for Pasupalak, and an opportunity to tell Gates the story of his very first hustle.