By Sahil Zaman, Legora.
I was born in India, a place where dawn seems to hold a special warmth, the streets hum with hawkers’ calls, and the notion of ‘middle class’ can include a housekeeper and driver. In my earliest memories, I’m running down a tree-lined lane near our home in Delhi, chasing the clanging bell of a rickshaw driver. I fell and still have a scar on my eyebrow as a memento. Then one day, my parents announced that we were moving to Canada.
Canada, I knew, had its capital in Ottawa, was a major exporter of wheat, and had one of the top three best flags in the world. I used to read my family’s encyclopedia to pass the time. As I found out, the world’s tallest freestanding structure didn’t factor heavily in my life after we arrived in Toronto’s scruffier suburbs. I quickly learned it was possible to go from ‘comfortably middle class’ to ‘almost broke’ in record time, especially in a country where we had no established connections, no charted future, and no relatives to slip us job leads.
As we settled into our new environment, I bounced from one public school to the next. Between the mould-infested ‘portable’ classrooms, the ever-present smell of sour milk in the cafeteria, and the occasional fight breaking out over perceived slights, I wondered if I’d ever fit in. Still, for all the struggles, I discovered a deep affection for Canada. I loved the underlying warmth of people who – once you got past the hallway bullies – were genuinely kind and helpful. To a fault: a well-meaning teacher once assumed I didn’t speak English because of a misunderstanding and offered to let me skip my assignments and tests. Not one to look a gift horse in the mouth, I immediately accepted. The plan unraveled after I had to explain to my parents that I was almost failing sixth-grade English because not only had I stopped doing any work, I had also been pretending to not understand English to keep up the ill-conceived ruse.
By the time I was sixteen, my love for Canada translated into the bright idea to join the Canadian Army reserves. I suspect I was drawn by the promise of a sense of purpose. The only problem was, the day-to-day existence in the army involves marching interminably on scorching parade squares, digging intricate trenches by hand and then filling them back up, and polishing combat boots to a mirror shine. I wasn’t exactly saving the free world.
After completing undergrad, I voluntarily deployed to Afghanistan, much to my family’s horror. I’d love to say it was pure courage or unwavering principle, but frankly, I wanted to be part of something important. I was seeking purpose, and I found it. My team worked on providing military support to Afghanistan’s fledging civilian government. We helped restart a dam. We directly supported an orphanage. My feelings on seeing all of that destroyed about a decade later is a story for another day. Also for another day is the story of how I became a poor man’s Milo Minderbinder in my nationwide endeavour to source and smuggle Tawny Port into a military base to help the Royal Canadian Navy celebrate Admiral Nelson’s victory at the Battle of Trafalgar in 1805. In hindsight, that was my first entrepreneurial adventure.
Upon my return, law school lured me in with visions of status and power. I drank the Kool-Aid and jostled my way into a prestigious global firm to chase big deals with an even bigger ego. One minute I was pumped about working on world-changing mergers; the next, I found myself manually sifting through gigabytes of ‘slack space’ – literal garbage nonsense on hard drives created due to the vagaries of file allocation tables – just because a client was willing to pay for that work. This was ‘digging trenches and filling them back in’ and thus I needed to find my ‘restart a dam.’
Eventually, I left to co-found Closing Folders with a friend from law school. I’d love to say it was pure courage or unwavering principle, but frankly, I thought it was going to be easy! The idea was simple: automate the mind-numbing tasks that had me pulling all-nighters, so lawyers could get back to being lawyers.
Little did I know, the road to disruptive legal technology is paved with polite rejections and the occasional scornful laugh. We strutted into the offices of large global firms with steely confidence, only to be met with ‘oh, that’s cute,’ before they sent us packing. We pivoted to small local firms, who found the idea intriguing but cowered at the mere mention of ‘the cloud.’ For a while, I felt like we were hawking a radical new invention – electric lightbulbs in a world that still found comfort in candles – only we didn’t have Edison’s genius or backing to assure anyone.
Our big break came when a large Canadian firm decided to give us a chance. We made it our mission to wow them by any means necessary: begging, bribing with sandwiches, giving personalized demonstrations in cramped cubicles, you name it. We lurked in hallways. We humbly apologized for nearly every email we sent (‘Sorry to bother you again!’). As word spread, we pounded the pavement around King & Bay, a legendary Toronto intersection where all big firms are clustered. We didn’t see it at the time because the left side of a hockey stick growth curve is no different than a cardiac monitor’s flat line, but things were turning around. That single success story multiplied, and before we knew it, every major Canadian firm was using Closing Folders. With each new success, my old sense of purpose was reaffirmed: we were actually making life better for overworked lawyers.
Those were exhilarating years: part hustle, part happenstance, and a lot of dumb luck. Then iManage came calling with an offer to acquire us. At first, I was torn. After years of grinding, running the business was finally fun. And what of our customers and employees? But iManage made an offer that went far beyond financial numbers, one that preserved our core vision and promised to grow it. So we took the leap, ensuring our product, our customers, and our employees would be well-supported.
I spent three years at iManage running Closing Folders. We continued to grow, which felt terrific, but as any entrepreneur will tell you, going from ‘let’s move fast and break things’ to ‘let’s do 3 days of compliance training’ can be a jarring transition. It felt a bit like going from rebuilding a country back to marching on a parade square. Once my three-year term was up, I decided to step away, chasing the next iteration of my purpose.
A few months morphed into a year and a half, largely spent with my wife and our two young daughters. I spent that time travelling, cooking increasingly intricate feasts for my girls, and testing random startup ideas that never quite saw the light of day. Meanwhile, the world of AI evolved faster than a toddler can throw my keys in the toilet. The technology has reached a point where it can crack jokes that are actually, well, funny, and not just ‘funny for a computer.’ A few years ago, an AI making a joke would have been considered artificial general intelligence (AGI). Now we just move the goalposts on what we consider AGI. We’ll look back in a few years and scarcely recognize the world we left behind.
That’s where Legora came into the picture. Their approach to collaborative legal AI is exactly the kind of purposeful mission that gets my heart pumping. So I joined them, ready to help bring that game-changing technology to North America. By leading with purpose, optimism, and a bit of good cheer, I’m hoping we can shape the future to make a positive difference in the universe.
Many thanks to Richard Tromans for inviting me to submit this article, and also for inspiring me to take a career sabbatical.
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About the author: Sahil Zaman is Head of Canada at Legora. He previously co-founded Closing Folders, where he was the CEO, and then worked at iManage as Head of Business, Legal Transaction Management.