Why I quit my job at Microsoft to start a Startup

Today was my last day at Microsoft. I decided to quit my job after 1.5 years of an amazing learning experience. In all my time here I don’t think there has ever been a time where I regretted joining Microsoft. Sure there were moments where I wasn’t happy with the way things were shaping up but that’s part of the journey.

Overall I think Microsoft is one of the best things that has ever happened to me. Making the decision to leave wasn’t an easy one and was made after a lot of contemplation and thought put into it.

I apologize beforehand but this is going to be a long post. For people who need a quick summary, this is it

I know startup is what I want to do and there is no better time than now

So Why did I Quit?

I don’t really remember why but by the end of my third year in college, I knew that I wanted to one day start my own company. Maybe it was the joy of making something and see other people use it and have full control over the process or maybe it was me just following the Fad.

I had started working on my own startup Intigrent, where we were basically trying to make an online course platform with a few new features. We wanted the online courses to be more personalized. Maybe it was a good idea, maybe it was a terrible idea. I will never know because 9 months into the startup me and my co-founder had a fight and we decided to part ways. I graduated college and joined Microsoft after this.

I continued working on the idea on weekends and brought in a new co-founder. She was my best friend at the time. We made a pivot in the idea because we felt making content would be a huge challenge. So instead we decided to focus on leveraging existing online content and making personalized curriculum for school kids. But 5 months into the startup, she and I had a personal falling out which was also a death blow to the professional relationship.However I still believe that this is a very good idea but maybe I am not the right person to build it.

So by now I had experienced both losing personal relationship due to professional fight and losing professional relationship due to personal fight. The personal fight however had a big impact on me and maybe in some ways I am still trying to cope with it. But post these 2 experiences I thought maybe startups weren’t my thing and I should just get back to regular work and try to build a strong career at Microsoft.

And I tried, I tried really hard to put all my focus on my work at Microsoft. But I would always get excited when I heard a new startup idea or came up with one myself.

After-all the heart wants what it wants

I was just starting to explore what chatbots meant during this time by building a few useless fun bots like pokedex and a personal resume bot. But as I explored more about this field I realized that 98% of the chatbots out there suck and this was an AI problem and not how easy it to build a bots problem. So I came up with the idea of http://ozz.ai which helps people make smarter chatbots.

I was pretty convinced that this is what I wanted to work on and made the decision to quit. It was a hard decision to quit my comfortable, well paying job but I only had to answer one question, whats the downside?

I think most people think of risk the wrong way. There is no risk in quitting a job, the risk is in staying back. Think of it this way. You are 23, have no family to take care of, can survive on fast food and have a long career ahead of you. This exact combination happens once in your life, just once. You will have 100s of opportunities to work for a big company but you are 23 only once.

Having realized that, the decision was pretty much made and I was lucky that my parents understood my point of view and supported me in this.

Why not work on it part-time?

By far this is one of the most common questions I get. “Why don’t you work on this in your free time?”, “Why don’t you work on this during weekends?”

I believe that this a fundamentally wrong approach. Startups are hard, I know from my two failed experiences that there are so many things that can go wrong and most of them at some point will. You need a lot of focus and will to get over these and keep moving on. I think startups are one of those things where you are either all in or you are not. There is no middle ground.

Reid Hoffman, founder of LinkedIn, famously said starting a startup is like “throwing yourself off a cliff and assembling an airplane on the way down.” To start a startup while having a day job is like throwing yourself off a cliff but with a parachute on. When things get hard you are going to deploy the parachute.

The only way to maximize your odds of actually building the airplane is to have no parachute, no backups and nothing to go back to.

What’s next?

I am not sure if ozz will work out or not but the one thing I am sure of is, I won’t have regrets. And the failure wouldn’t have been for lack of trying.

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