In 2012, I was working at Google in India, jet setting to new cities every month to talk about Google Search to people in India and abroad. After a random drunk call with a Captain in the Indian Navy, I decided to exchange my stable life to become one of the first Indians to sail in the Clipper Round the World Yacht Race.

Never had I expected that the two years starting from taking the decision to getting off the boat would teach me more than I learned in my MBA. Starting today I am going to share some of the most interesting lessons I learned on the journey.

If you don’t ask, you don’t get

Growing up in a family with limited means meant that I feared to ask for money from my parents. Same applied when I had to raise £50,000 to participate in the Clipper Round the World.

Asking for anything demands commitment, clear communication and the ability to take rejection. Commitment and conviction were never a problem because a photographer friend had said, that the best way to make me smile was to talk about a boat and that he had only seen me smiling when I was sailing. But the fear of rejection while asking in person scared the wits out of me.

Here is how the Clipper campaign helped me perfect the art of asking:


I wrote over 300 emails and letters to potential sponsors to raise the money and received only 4 responses. In a way, it was easy for me to handle these rejections as emails are impersonal to a large extent. I feared to ask and I was about to give up on my dream of sailing. This is the point where someone interested in the intrigue of sailing round the world would have given up.

I kept at it and by the time I finally got on the boat I had sent upwards of 4000 emails and letters.

I had made presentations to politicians, businessmen, talent management companies, media, prominent sports-persons which all had ended in rejections. The idea of sailing round the world is cool, but perseverance sets apart the interested and the committed.

Clear Communication

Crowdfunding gave me a great opportunity to begin gaining confidence to ask as I had to start by asking my friends first. I had to develop a great communication strategy to get the people who knew me well and the people who didn’t shell out money from their pockets to help me achieve my dream. After all, most of them had been witness to my antics on social media and owing to my introversion had hardly ever had a meaningful conversation with me. There was a clear discontent among most people for the disproportionate amount of funding and attention cricket receives in India. Packaging this with the clear pride Indians take in supporting any first that happens in the country wasn’t the ideal message I had in mind, but it seemed to touch a nerve.

This was possible only because I was able to establish a relationship with people through my daily communications and interactions where I was able to demonstrate my commitment for the goal. A lack of communication could have created a distance in the relationship which would have hampered the virality of the campaign.

I was the talk of the town on Facebook and Twitter and the money started coming in. People who I had never met, people who knew me only through an acquaintance had started sending in checks because of the intense messaging that I had could develop owing to my clear communication.

Getting Over the fear of rejection

But life being life, crowdfunding had only gotten me to 2% of my goal. Rejection was my biggest fear in going out and asking people who could support me by writing one check instead of crowdfunding from people who were writing off a huge part of their salary’s. This is when I took the biggest gamble, I shot off an email to the then CFO of Google, expecting the email to get lost in the black hole in his inbox. To my surprise, and that of the people who were cc’ed on that email the CFO had replied within 34 minutes (I still can’t believe this happened). He had personally crowdfunded money for my sailing campaign from the L-Team at Google and I got to keep my job while I had gone sailing (How cool is that?).

One could say that your deep commitment for a project could make you fear rejection, more so when you have given it all that you have. However, it is essential to realize that rejection will come from time to time and it is essential to not take that rejection personally if you have to ever see your project come to fruition.

It is easy to oversimplify the art of asking by saying that “if you don’t ask, the answer is always a no”, but the art of asking needs a sensitive combination of the three elements above to make the answer a ‘maybe’.  

Leave a Reply

Your email address will not be published. Required fields are marked *