This question haunted me and literally made me very restless for 2 years. I was on a full time job and every passing day made it more difficult for me to show up at work. Not saying that I did not enjoy the job that I had. In fact that was the problem. I loved the job that I had. In fact I would go on to say that I had a dream job. I was working on interesting problem statement, I had the best team I could ask for, I had the freedom, I got recognition and we we collectively making a difference for the organisation. Yet, it felt that something was missing. It took me 2 long years to come to terms and then #startup.

So when do you #startup?

If you prefer video

else read along.



Each of us are born with a set of lenses. We all see every day life and happenings through our lenses. What excites me does not excite my spouse and what worries her doesn’t worry me. Well many things dont worry me! Similarly when problems present themselves to you, you might observe them differently from the rest of the world around you. Some aspect of the problem might attract your attention more than other aspects of it. As long as you recognise this you will see some kind of inspiration from the observation that you are making.

In my case when the whole media was obsessed with reporting the human and personal losses from the Vardah storm that hit Chennai in 2016, my mind was intrigued to know more about the losses incurred by small businesses.


The next stage happens when the observation that you made starts to come back to you and keeps posting questions at you. This is when you are driven to identify the root cause of the problem. You end up googling, talking to people and reading the news to uncover more facts around your observation. Sometimes you may fall into the trap of confirmation bias, but it’s OK as long as you keep an objective approach to identify the problem in the long run.

Post the storm I started to look at why the small businesses incurred so much of losses and why they had to shut shop down. Since I was coming from an insurance background, my mind started to explore that part of the problem. Yes, there was an element of confirmation bias here. I identified that small businesses in India were grossly un-insured or under-insured. In fact 99 % of small businesses in India were either un-insured or under-insured.


This is the most critical step in the process in my opinion. I mentioned about confirmation bias in the previous section. This is the step in which you start to look at the problem using the lens of the stakeholder as against yours. If you do a good job of empathising then you get to understand the world view of the stakeholder and are able to get to the bottom of the problem. Empathising cannot be done by just reading articles. You need to have open-ended conversations with the stakeholders. Conversations upon conversations help you get there. In many instances, you might be that stakeholder who is facing the issue. This is the case with many B2C startups that we see. You as an individual face a problem and at some point in time you don’t want to live with the problem any longer.

I started to talk to small businesses in Chennai, insurance companies and insurance agents to understand why 99% of small businesses dont have adequate insurance to cover for catastrophic losses. I probably would have had 100+ conversations to really get to the bottom of it.


It is dangerous to enter this stage without doing enough of the previous stage. Entering this stage should sound and feel natural to you. In fact you may realise it only later on that you are already obsessed with the problem. You may discover this when your friends and family tell you to stop obsessing. One important piece of advice that I want to share is to obsess with the problem space and not the solution. Obsessing with the solution is most likely to be counter-productive to your startup.

I did enter this stage with my first startup. The blunder that I made was that I had started to abscess with a solution and not the problem. I was more passionate about building the solution and giving it life than about solving the root problem.

With my second startup, GoFloaters where I wanted to help remote and distributed teams work from anywhere, though the stage happened naturally and I was open to consider all types of solutions for the problem that I was obsessed with.

You #startup when you reach this obsess stage and can’t stand more of it and the only thing that looks like a logical thing to do to ease yourself of the agony is to start solving the problem.

I take inspiration from a TED Talk by Itay Talgam to summarise when do you startup. He talks about various music conductors and their style of leadership in his talk. He talks about a German music conductor called Herbert von Karajan. One of his musicians asked him when do I start playing the notes.

He replied “You start when you can’t stand it anymore”.

Shyam Sundar is the Founder and CEO of GoFloaters. He is a Fulbright Scholar and an accomplished technologist. He is a champion of work from anywhere and remote working. GoFloaters helps individuals and teams to #WorkFromAnywhere.

Founder & CEO of GoFloaters (On-demand work spaces) | Champion of #Responsible #WorkFromAnywhere