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Lessons from a Serial Entrepreneur

By Kushal M. Choksi

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We entrepreneurs are an irrational bunch. Who else in their right mind would choose a path with a probabilistic expected value realization of close to zero? The entrepreneurial journey often gets painful. Lonely. You realize very quickly that life doesn't owe you anything. And knowing all of this, some of us still go back right to it, wearing a badge on the sleeve that reads "serial entrepreneur'. Logically this makes little sense!

I was triggered to become an entrepreneur after I survived 9/11 attacks in New York. I felt that life was too short to be playing safe after getting a new lease on life. I left my promising Wall Street career with the top investment bank to join a nondescript startup. Over a period of time, one failed startup and two successful exits later, I still can't claim to have hacked the code of entrepreneurship entirely, but I've picked up a few learnings along the way that I wouldn't trade for anything.

The loser is the winner

It is a game of losing. Losing your fear of the unknown. Losing your false sense of control. Losing your attachment to perfection. It is the game of losing all the noise, till you can hear your own heartbeat. Losing all those also-ran ideas, till you meet that one that refuses to go. In this game, the seeker is a finder. The loser is the winner.

Get out of your own way

As humans we are programmed to label ourselves. I am good at A. I can't do B etc. While it's important to play to one's strengths, we often become the scapegoats of our own conditioning. This results into holding back one's self, not taking enough risk for the fear of failure, and validation-seeking behavior that has never helped any entrepreneur.

Everyone's path is different.

In this non-deterministic game of survival, there are no definitive formulae that apply. External circumstances and all other background parameters like personal finances, relationship status, age etc. are laid out uniquely by nature for each one of us. Respect your reality and take a leap.

Market research has its place. In a bin.

All the studies, surveys, and research suffer from a strictly backward looking bias. When you believe in yourself and in your product, you have the power to create the need. Your passion supports you until your product finds the right market. The past few years of running an artisanal chocolate company has been one of the highlights of my journey. However, if I had relied on market research for a go/no go decision, I would have never gone for it.

Listen to your most underrated organ. The gut.

We are trained to think logically. But logic is only limited to what we know. And what we know is limited. So, relying on logic entirely would be like driving while looking in the rear-view mirror. That's where the gut instinct or intuition comes in play. Time is a scarce commodity and intuition can help save a lot of it. A refined intuition is a lubricant against the massive friction that one experiences when starting anything new.

Dorothy was right. There is no place like home.

Put yourself on your to-do list. We entrepreneurs are good at justifying why we have time for everything but ourselves. I benefited immensely from my practice of mediation and breathwork. Just taking out a few minutes to connect with ourselves every day makes a huge difference in how we show up for everything else that we do. An arrow must be pulled back before it tears forward.

Entrepreneurship after all is nothing but a dance on the edge of a sword. A delicate balance between passion and dispassion. Being uncomfortable with being comfortable and being comfortable with being uncomfortable.

Kushal M. Choksi

Author & Entrepreneur

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