He who knows when he can fight and when he cannot, will be victorious.  – Sun Tzu

Management quotes are rife with the metaphor of the “fight”.

- Fight for a raise from your supervisor

- Fight against a competitor for a deal with a customer

- Fight for acceptance from the community you do business in

The fight metaphor pits you against the party who has the resources which must be extracted by force.

Next time you get into this arena, how about fighting for trust?

- Fight for your supervisor’s trust…not their budget

- Fight for your customer’s belief…that you will not let them down

- Fight for a community’s confidence…that you care about their interests

Trust not only changes the battlefield, it eliminates the battle.

Now the fight is with yourself – building capability, consistency, and competence so you are willingly given what you are looking for.


It’s not information overload, it’s filter failure.

Clay Shirky

My father is an artist, art historian, and conservator of painting. One of his roles when I was growing up in the 80s, was Curator of Painting at the Prince of Wales Museum in Mumbai. I had the unique privilege of being exposed to a range of art as a result. Art from the great Indian contemporary painters like M.F. Hussain and Sabavala, to the European greats like Rubens, to painted, sculpted, and gilded masterpieces from ancient India.

I realized back then, that this was an unbounded and fascinating world filled with millions of creations. It took a bit longer to realize that I had by my side, one of the best “filters” for helping me discern the attributes of great art: my father and his band of fellow scholars. When they pointed to a piece of art and agreed (or disagreed) that it was great (or not), it came from years of training, observation, and research, culminating in what we might call discerning taste. If they had an algorithm to identify art they liked, it was only in their sub-conscious, intuitive, matured over time and complex like a fine wine. Equally interesting were their stories associated with the art and artists; bringing them to life, adding a whole other dimension to the decision. Suddenly, a somewhat imperfect piece of art became worthy of restoration or acquisition with the backdrop of story and history.

Somewhere along the way we lost this expert human filter to the online world and need to bring it back.

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Taste is a by product of study, observation and being steeped in the culture of the past and present, of “trying to expose yourself to the best things humans have done and then bring those things into what you are doing.”  -Steve Jobs [1]

Good taste, that elusive quality only a handful in our network seem to possess. Can’t define it precisely, but we know it when we see it, and, if it’s aligned with our own sense of taste, we love it, appreciate it, and are inspired by it. Steve Jobs was the Emperor of good taste in the integrated digital experience. Steve Jobs was THE  taste-MAKER.

Me? I fall more on the taste-ER and taste-ERR side I think, experimenting my way through new experiences in food, wine, art, books, movies, outdoors (the list goes on), recommended to me by my taste-MAKER friends; trying to steep myself in the things I would like to learn about, help me grow, and enjoy.

I have two confessions about how I handle recommendations:

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It was a privilege to speak at the first Startup Saturday (Ahmedabad)  this year and meet some of the best local entrepreneurial minds. Thanks to Startup Saturday and their local team for including me. What follows is the core of my talk titled, “Five Uncomfortable Lessons From The Silicon Valley Trenches”, adapted to a readable format.

Some Context

For my talk to be meaningful I constrained myself to two guidelines:

First, if I was to say something new / different I needed to move away from the prescriptive which is way better documented and better narrated by many others. Instead of focusing on the how tos of pitching, funding, “getting outside the building” etc.,  I figured that narrating some of my own experiences from the trenches would be more useful.

Second, I wanted to make it relevant to my local audience. The general body of prescriptive knowledge often assumes that passion, drive, and smarts are the great equalizer; startup how tos apply generically; and that culture and experiential DNA (where you come from) are somewhat orthogonal to entrepreneurial success. My experience was different. I learnt that before attempting to disrupt markets, I had to disrupt my own comfort zones because of where I came from, and I suspect, a large segment of the Indian high-tech entrepreneurial talent comes from:

  1. An engineering/analytical background with an emphasis on data and problem solving…hence a discomfort with fuzziness, approximation, and ever-changing targets.
  2. An educational system that rewards perfection and “knowing” within the constraints of a syllabus…hence a discomfort, even embarrassment, at “not knowing” or asking for help.
  3. A tradition of hierarchy of roles and relationships where speaking up and “selling” is impolite…hence a deep-rooted discomfort with the idea of “selling” one’s idea or “marketing” oneself.

The uncomfortable part of these lessons then, is the unlearning and unshackling from this training and scripting to gain a broader perspective of the startup and business.

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At some point in your rising career you will meet an Eighteen Point Someone

Regardless of your line of occupation, if you are successful and rising, sooner or later you’ll bump into and present to an Eighteen Point Someone. Unlike the underachieving Five Point Someones from Chetan Bhagat’s hilarious book by the same name, the EPS is a time constrained, attention deficit, impatient, decision maker.  The EPS may have your promotion, funding, or resources at their mercy. If you met an EPS in domestic life, you can be sure their dog and family loves them but in the heat of everyday business the EPS is a different being…it comes with the territory.

The Eighteen Point Someone cannot see below eighteen point font or focus beyond one page

Lest you take the Chetan Bhagat Five Point analogy too far, I’m not talking about the EPS’ GPA but rather an optical problem most of them have – they cannot read fonts below eighteen point. Far too often I have seen the “EPS uninitiated” deliver large amounts of data, text, images and stats to get their point across, battling the time and optical constraints of the EPS. It’s a foregone conclusion, as their thoughtfully organized analytical masterstroke is smeared by the blur of their 10 point font. If your content, decision, analysis or whatever is below eighteen point and over one slide forget it!

Dealing with an Eighteen Point Someone is a PAIN but you will thank them in the long run

Remember the diamond? It’s just black and smudgy old carbon subjected to pressure isn’t it? Well, dealing with an Eighteen Point Someone does the same to you business communication. It crystallizes your thought, cutting through the smudge of TMI (too much information) to reveal just the key facets of your presentation that will lead to a quick decision.

At some point we were all Eighteen Point Someones

Remember Kindergarten? We all started there. The big picture of the apple and large font A worked so well…look how far we all came. Then at some point multiple fonts, varying line spacing, formats, colors, graphics, spreadsheets, tables, animations and effects took over. Brevity was beaten by Verbosity.

Get pithy back

Now if you only skimmed the bolded big font in this blog post, you are well on your way to being an Eighteen Point Someone yourself. If you read my entire blog, there is still  hope for you. You now know what it takes to get past an Eighteen Point Someone.

I’m still working on it too :)

Yours Truly,

Sixteen Point Someone.

p.s Being a 12 point someone myself for longer than I can remember, I learnt the neat trick of having a 1 slide decision presentation with a 9 slide backup. Its works well. If you are lucky you get done with one slide and get your Eighteen Point credit. If you are unlucky, you are at least credited for being prepared. 

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