Turning 40. Bootstrapping for 5 years, and 15 years of marriage.

Krishnan Nair
3 min readApr 28, 2020

I turned 40 last month, been running a startup for 5 years, and married for 15. Thought this is a good time to spew some gyan on turning old(er), being a founder, and give one piece of advice on marriage.

I have no sadness in turning older. For some reason, I’ve always enjoyed getting older. No, really :)

But life becomes rote after a point. At that point, I left my job and started up. Then everything turned 180 degrees.

I had no clue what I got myself into. The saddest part is that it took me a long time to realise I didn’t know jackshit.

Be always aware that you don’t know much. You learn by observing, listening to advice or going through stuff. I did the last.

At a startup, everything is because of you. Pandemic struck? Well, you should’ve built more cash reserves. Global recession? Should’ve gotten into a different space. Hired a jerk? Obviously your fault.

Unless you’re earning money for time rendered, bootstrapping is hard. I realised later that bootstrapping also requires capital. Looking back, this was idiotic, but ya, I didn’t plan for this. Even if you’re not looking for investors, look for money. Having enough cash, is the #1 priority for a CEO.

If you’ve been in tech all your life, my friend, you don’t understand business. My respect for folks who’ve built their company from scratch, even small brick and mortar shops, has grown manifold. A lot of techies think only they do real work, everyone else does “timepass”.

If you’ve built tech at a startup and have not been involved in building the business, then you have not really been exposed to the real difficulties of starting up. Tech is what scales the business but if there’s no business, what are you scaling.

To build a company, you have to do things that don’t make sense. If it made sense, everyone would be doing it. As your company grows you realise that most people in your company also want to do what others are doing. Social comfort is hugely underestimated in decision making.

As a founder, if you’re constantly doing stuff, you’re doing something wrong. You need time to think. Once in a while, it’s important to get up and not know what you’re going to do today. That’s how you improve the business. If you’re just turning the clacks, something’s wrong.

Lot of startups fail. For all the reasons that people attribute their failure to, another startup will be doing the same, and succeeding. The common thread amongst successful startups is that they persevered. But I worry if I’m persevering or being foolish :)

Taking decisions > identifying faults and doing nothing. People don’t like to decide things. As a founder you need to. I’ve reached a point where I just can’t put across a problem without offering a solution.

Getting customers is the easier part. Using marketing to get your customers is a function of how much cash you have. The hard part is figuring out how to get the right customers and at the lowest cost. This is a make or break activity.

Getting customers to use your product is a different ball game altogether. Discounting seems to be the preferred way. But as a bootstrapped company you need to provide value and get customers to pay for it. It’s hard, but fun. This is what keeps me going.

And the last piece of advice is on marriage. From 15 years of being happily married. The secret to a happy marriage is never using the words “I told you so”, “it’s your fault” or any variation of it (“why didn’t you”, “I was right”, “you should’ve” etc..). Try it out :)

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