The first small steps that led to the launch of Zensurance
Part I: The Leap from Stability to Uncertainty
It’s been a few years now since Zensurance was acquired by The Travelers Companies. I am often asked questions by people about my experience and that’s led me here. I decided to share some of the key learnings from each stage of the experience starting with this post that covers the first step.
It was sometime in the early fall of 2015 when I finally decided to make a very big change in my life. However, it wasn’t a decision made in a moment. I would argue it was a decision that had been in the making for 20 years.
In 1994-ish I had been exposed to a web browser in my first year of college. It was really life changing for me. That exposure led me down a rabbit hole. I ended up building up a website(you can read about it here) to practice my technical skills but what I was really doing was building a business without even knowing it. I never actually turned it into a real real business but it set the seed. It was the early days of the dot com revolution but I was an international student in the US and didn’t have the liberty of doing whatever I wanted. I had to maintain my status as an international student and then after graduation to stay in the US I had to get a job. I ended up falling into the trap of delaying and delaying because there was always a good reason to delay.
The time that I was delaying was not wasted though. My experiences were helping me grow a variety of skillsets. I went from being a software engineer to business school, onto consulting, working at an accelerator, and finally as an internal strategy professional. I also moved countries, from the US to Canada. It seemed like I was lost jumping from one thing to another. I was always keeping up with the tech sector and the startups that were trying to change the world. I’d spend weekends playing around with code. The fire was still burning in me. The one constant in me was that I always kept thinking about that startup that I was going to launch.
In mid-2015 I was really feeling the startup itch intensify. It was around this same time that I once again came across Jeff Bezos video in which he spoke about the Regret Minimization Framework; what the new generation calls YOLO. I really didn’t want to look back at my life and have major regrets.
Although I had a great job working with a great boss at a great company I was not content with not going for it. A series of events led me to realize how little time we actually have and if we don’t spend it doing what makes us happy then what’s the point?
I walked into a meeting with my boss and informed him I was planning on leaving. He was supportive but did ask me to stay on for a couple more months to give him time to transition in someone else. This was also really helpful because it gave me time to transition myself into startup mode too and it was over this period that a lot happened that led to Zensurance.
I started to get out there and meet people and have the conversation about the next phase. I was going all in. I was going to startup something. What was it? I had no clue! I wasn’t scared though. I just knew that starting it and shifting my mindset would get me to where I wanted to be.
One of the meetings I had was with an acquaintance whom I had gotten to know after I moved to Toronto. It was over breakfast on a Saturday morning at a restaurant called the Canteen. I was catching up and informed him that I was embarking on the entrepreneurial path. He asked if I knew exactly what I was doing and I was honest, I had ideas but not committed to any idea because we tend to get excited over our ideas. What matters is to do the research and validate a problem exists. That along with having some passion about solving the problem are probably the two first steps one should take.
Our conversation continued and it seemed to inspire him to perhaps leave his role. He had been at a consulting firm for nearly his whole career and wanted to leave. We continued talking and he suggested maybe insurance would be a good space. Fintech had been hot for a while and I knew behind fintech there was an insurance tech wave building. We decided to explore the space. He had done some consulting in the space but that was not where we went. We ended up white boarding ideas around insurance for small and medium sized businesses…we looked at all the different options. Do we become a full brokerage offering an online end-to-end solution? Do we create the software and sell it to existing brokers? and so on. We were doing this on nights and weekends as I had to wrap up my commitment to my boss and he decided to end his work around the same time I was ending mine.
We had settled eventually on developing a digital brokerage focused on the Canadian small and medium sized business sector. There were examples south of the border and we thought Canada could use one too. I personally was passionate about building a solution that made it easy for business owners to buy & manage their policies digitally. The traditional methods were archaic and not for the future.
So that was it. Found the problem to solve. Had a co-founder. Now it was time to launch!
Key Takeaways from This Phase:
Making the commitment is VERY VERY difficult. Even now that I’ve had an exit I still find it to be difficult to take that first step of committing to go all in on a startup. It requires the courage to move away from stability and that’s always going to be difficult. One possible way of making it easier is to start a side gig with a plan to get to a specific milestone before you go all in.
Knowing what problem you want to solve is great but there are plenty of problems in the world. The idea isn’t the only key, execution is what will make a big difference.
It’s okay if you don’t have industry expertise. You can hire for it. That’s what we did.
If you have any questions please post them in comments and I will respond as soon as possible.