Why ‘Why’ is possibly the best worst word for an entrepreneur

Talking not listening; that’s not entrepreneuring

I’d like to start by saying that odd titles don't necessarily have to be tabloidish or attention seeking, although it does help get you … here.

While packing my stuff in my awesome carry on samsonite for a 3 day flight to Colombo, I felt the urge to check the weather. Instinctively (taught not genetic), I reached for my nexus 5 and swiped up for #GoogleNow to tell me the good word. It occurred to me in that moment a thought that I felt I should pen down and share.

It’s funny how sometimes the mind wanders without being prompted intentionally. Rather, an unintentional prompt can trigger some interesting perspectives. While I wrote that last line, some dude just walked by me in the Emirates lounge trying to pick a wedgy. #Erase #Visual #Stat.

Coming back, my wandering mind took me to the thought about how Google Now may have come to be. I’d like to think some simpleton thought it would be a great idea to give people access to fundamental, functional information that helps them…think, prepare, do better. For an Android user, this won’t come across as a sales pitch — obviously.

But what if that simpleton went to Sergey or Larry and said, “Hey guys, what if we could give people access to the information most important to them in a simple gesture?” and in return got “Why?” as the only rational response?

Apply that thought to anyone who has/is/will try to do something ridiculous. I mean Google Now would have been a pretty gnarly idea 2 years ago, but 20 years ago people be like, whaaa?

I hear people giving me the big ‘W’ as a reply to an idea. Not that I’ve done anything worth a wikipedia page mention, but what if I do and it’s because I kept getting challenged, not by encouragement but rather by discouragement?

I started a startup nearly a decade ago but did jack squat to realize its potential. Instead I trudged along and followed a career. Sure it had it’s ups…and downs. I even learnt a ton, so there’s no regret whatsoever.

I read stories about how startups get funded and then go back to share how so many ‘intelligent’ people didn’t take a bite because they just didn’t see the logic…then. Now of course everyone does, since the money came from somewhere and the business succeeded to create the same traction in question.

I like ‘Why’ because it gives me perspective. Not because I know the person asking me is doing so to challenge my idea in an unsupporting way, but because it is up to me to accept that meaning. Alternatively, I can pull a Barney Stintson and say, “Challenge Accepted” and just game on to prove what I’m doing.

I think the best way to fix a problem is to apply determination and clarity of thought, not just ‘focus’ and KPIs. If building a startup was like baking cookies, we’d all be billionaires and there’d be no one to share an experiental story with. Except maybe our cats. But then one never knows about that either.

I started to pay more attention to that first startup. Then I started another startup to finance the first startup because I wasn’t ready to ask for money. Now I’ve got two startups, a third in the works and almost ready to take the first for seed funding. Who knows…

Dare you to ask me ‘Why’.


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