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That one time I was worth a million



What was once seemed like something out of a movie turned on it’s head. The San Diego sun beat against me and my surfboard. I thought I was cool, but really, I was just a geek who bought the cheapest surfboard he could buy and after a million attempts, still couldn’t catch a wave. I didn’t care though, I felt free. A week previously, I was worth a million dollars on paper, a lot of money for an early 20-something. That day, I was worth, maybe a few thousand dollars. I gave it all up and it felt incredibly liberating knowing I didn’t give a shit about money. I didn’t know what I’d do next, but how many of us really do? 

This story starts in Waterloo, a sleepy city filled with deprived students who dream of one day escaping the horror that is the University of Waterloo. My former boss had connected me to someone who connected me with someone. She sold me a future where the future of healthcare was one where integration and shared context among healthcare providers saves lives. She knew something about the problem, as she was a former C level exec of one of the largest electronic medical record companies in the world. Her cofounder had started and exited 10 companies. His first exit was for $24B. He owned something like 5 helicopters.

I had already accepted an offer to become a technical program manager intern for Amazon (the first one in the history of Amazon) but you don’t get to work with people at that level very easily. They flew me down to San Diego where I had my first sea urchin. There aren’t very many good leaders in the world. Most leaders lack vision and the answer to “why”. These two were an exception. The “why” was clear: we’re going to save lives and a lot of them. I was in love.

I reneged Amazon’s offer, got a lot of heat from both the university and Amazon, and set my eyes on SoCal. Having had 8 internships throughout my undergrad career, the first day moving into a new city is always a race. You have to rent a car for a few months, sign your lease papers, run to Walmart to get some essentials, find a mattress, all within the timespan of a day. I was exhausted but pumped. 

The office was in the middle of nowhere (Carlsbad, California). Nobody was ever really there except for me and sometimes one of the cofounder’s sisters. I started to wonder, “what did I get myself into?” It was still amazing though, the beach was a 3 minute walk, the people were beautiful (and way out of my league), and I was working with incredible people.

Fast forward a few weeks and I get a phone call. The two cofounders are excited. They have reason to be because they had just gotten Clay Christensen (royalty in business) to commit to being on their board. A signed copy of “The Innovator’s Dilemma” sat proudly on one cofounder’s desk. Oh and there was more. They had gotten Kaiser Permanente to commit money at a $100M valuation. I was a millionaire on paper. Life was amazing.

That dream started to turn. Politics became the central theme to every discussion. Everybody who was hired, was fired. There was no product direction, I had no idea what I was supposed to create. My mentor at the time told me to watch my back. One of the cofounders had a habit at yelling about everything and I lost faith in our ability to execute. A part of me thought “maybe this feeling will pass”. It didn’t. I couldn’t sleep for weeks. 

I’d go running at night beside the ocean. I was out of shape, I struggled to run 5km. I didn’t really care, there was something healing about it. I had a candid conversation with a cofounder. I was running hard. I lost faith in the management. I felt like I couldn't trust anything said. There was no concrete vision. I was putting my heart and soul into the company and at the same time, I was worried about being screwed. She empathized with me. She told me, solemnly, that she thought I should quit, pack my bags and go back to school. It’s exactly what I did. I gave up a million dollars and I’d do it again. A million dollars on paper might mean nothing. Had I stayed, I would have hated myself and I might have suffered for no reason. There’s a euphoria you get when something magical happens in your life. Your first kiss, your first paycheque, your first customer (if you start a company). I don’t think anything I’ve ever experienced, beats the feeling I had that day, quitting. I learned a lot from those experiences and still do the more I reflect on those experiences. All that said, the biggest takeaway was that, money, the thing that people live, kill, and die for, didn't matter to me. I can't describe to you how liberating that feels.

I left that company burnt out. I spent the next few weeks surfing, trying to woo a girl I've always been nervous around, trying weed for the first time, doing crossfit, anything to keep me from the paranoia that had been eating me up. It worked. I started feeling better. I went back to school, on schedule even, as if I just had an internship and that was that. 

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