5 things bootstrapping a startup has taught a two-time CIO 100 winner

In a previous life, I was the CXO at one of India’s largest asset finance companies. Before that, I was the CIO at one of India’s largest insurers.

I’ve spent over a decade at one of India’s largest technology companies, both in India and abroad. I thought I was fully prepared to bootstrap startup. I had some youthful energy from my yoga routine and the benefit of all the experience, i thought!

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The reality has been somewhat different. What I’ve had to work hard at over the past year has been quite different than what my two decades of experience taught me.

While startups are made to seem glamorous, with stories of mind-boggling success, innovation and passion, the beginnings of all startups are entirely different. Here are five key things I’ve learnt while conceiving and building a bootstrapped startup over the past year:

Always be humble

All of us have different strengths and weaknesses, based on our backgrounds and habits. A techie may not be a good salesperson. A salesperson may not be able to deliver the operations stuff day in and day out.

A person who has been an employee all his life may not be able to think fast and take bold decisions like a ‘businessman’. A startup situation exposes one to these frailties completely.

That is the fun and thrill of the startup, as one is constantly exploring one’s limits. With the right humility and nimbleness, one has to decide quickly: should i re-develop myself or collaborate with someone with complementary skills.

Collaboration could be at various levels, a co-founder, an employee or even a partnership. In a bootstrapped setup, it often means re-applying oneself as throwing money at problems will only increase the ‘burn’.

Test of endurance

There are a zillion things to do: both unfamiliar and uncomfortable. Unless one is mentally prepared to face the fear of doing new things, and face the anxiety of things not done, it will be tough to survive. 

The need for sacrifices

A startup is all consuming. Be prepared to give up a lot of stuff, but have clarity on what is important. For me, it has meant cutting down on reading, movies and tennis. I still invest some time on my yoga routine and try to sleep well.

Skills are important, but only if you create stuff with it

With so many technology changes hitting the economy, having the relevant skills has become very important. How one learns and deploys these skills is key. A regular job, if it’s operational, many not be ‘future proof’, as it could be automated.

So having a career view is more important than worrying about a job. If you extend it further, creating stuff that others are willing to pay for, is the ultimate recession-proof way to pick skills.

A startup is a great place to do that. I have learnt so much about things like digital marketing, public cloud, user experience design and AI during my journey. 

Ultimately, Life > Startup

Ultimately happiness and general fulfilment cannot be tied to startup or career success. No matter what we do, life goes on each day. Our children will grow faster and our dear ones older. Life cannot be ‘paused’, thinking we will come back, after say 5 years.

For me this means taking out time to spend quality time with my daughters every day, even if it is for a few minutes.

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