Unsolicited advice from an older entrepreneur

Look at me being all grown up and calling myself old. I had a few other titles that I was considering for this and it was a close contest. But I finally decided that I’m comfortable calling myself old (relatively speaking!). In terms of tech startup founders’ age, I’m definitely on the older side. The alternative titles I had in mind were –

  • A letter to my 24 year old self (from the future 34 year old self)
  • Yo 24 year old founder, stop being cocky for a minute and listen up

I fondly remember being a cocky 24 year old, so don’t be offended if you are one right now. You’ll grow up too!

Onwards with the advices / rules / lessons then, in no particular order –

Don’t mistake shortcuts for speed.


It will come to bite you back. Sooner or later. (be thankful if it is sooner). Conversely, if something comes to bite you back later, and you can attribute it to something that you wanted to save time on, call it a shortcut, and learn to identify those patterns.

More hours and more effort does not equal more productivity.

click for the back story if you’re a Simpsons fan

The fact that you’ll work harder, will not be enough to beat competition. Sure it is a valuable ingredient, and you’ll work hard anyway. But be aware of this rule. This will help you in out-thinking your competition, instead of trying to out-work them.

When estimating time for a particular product / feature, apply the thumb rule of multiplying your estimate by 3.

Mobius strip - Dilbert by Scott Adams

A very tactical thumb rule that has served me well. This will also help you understand the true cost of time and make you rely less on hope. Sometimes it’ll just sound ridiculous that such a small feature can take 1 week to complete. Trust me, it’ll actually end up taking 3. This rule has rarely failed me. The good thing is, if it does fail me on that rare occasion, I’m usually pleasantly surprised. And the other times I just wonder if we should all give up on making software.

Try to apply yourself on the most valuable aspects of business.

Menial - Dilbert by Scott Adams

Try to hire or outsource for the rest. I know you will not always have resources to hire. But your time is much more expensive than any of these odd jobs you keep doing without even thinking. I’m happy to report that I became much better at this as I grew up.

Don’t get too happy with the highs.

happy new year - Dilbert by Scott Adams

If you’re feeling you just made the deal of a lifetime, or had the most awesome killer idea ever, don’t go overboard with celebration or expectations. You’re not done yet, so keep your head down and keep working. This too shall pass – which may seem like a downer until you discover that it also applies to the next rule.

Don’t get too sad with the lows.

Be like batman. http://weknowmemes.com/2012/09/depressed-bane/

Or in other words, things are never as bad as they appear. There is always a way forward, even if that way means letting go of something you hold dear. Keep calm and carry on.

Ideas can be exciting. Until..

Great idea - Dilbert by Scott Adams

All ideas tend to fall into one of these buckets (usually within the first 10 minutes of them occurring):

  • Shitty
  • Done already
  • Too early for their time

The shitty ones are the ones which you should learn to ignore and not spend time and money on. I guess it is a skill that you’ll just have to learn by doing a few shitty ones. Only in retrospect will you appreciate how stupid it was to waste time on one of those.

The ones that are done already are not to be discarded. In fact some of the best ideas have already been done, but have tremendous scope for improvement. As your sense of observation develops, you’ll be able to find how you could make certain ideas 10X better. At first you’ll try doing so by adding 10X more features (Good luck with that!). Then you’ll start to value simplicity. Keep practicing, and you’ll start making things simpler and more elegant.

The ones that are too early for their time are also sometimes very hard to identify as such when you’re working on them. Again, mostly in retrospect does this knowledge come. You’ll never be shielded from pursuing these, perhaps that is a good thing. These are the ones that are always exciting and shiny and new. Keep them in your radar. The time will come!

Which also brings us to the corollary..

No one cares about stealing your ideas.

Brilliant idea - Dilbert by Scott Adams

Because once you’ve had that idea, all you’ll need to do it is bring it to life. You’ll be surprised at how lazy mankind is in bringing new things to life. So be open about discussing your ideas. This will bring perspective.

To end the post, lastly

Have fun!

Don’t take business and life so seriously that you forget why you started in the first place. Knowing this in times of extreme stress will help you look at things in a different light.


PS. I think I’ll come back for a part 2 of this post some time down the line. I could go on with this for a bit more! Also, if you have a cartoon to share, please do so in the comments. I like to learn from cartoons.

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