Why vs. How: What’s the big difference? After all, they are just different semantics, right? Actually not.
Here are a few questions that industry analysts/investors were asking to startups in 2008:

“Why would people buy bus tickets online when there are multiple offline booking options?”
“Why would people use 140 characters to share ‘what they are thinking’?
“Why would Indians buy online where they can’t even touch and feel the products?”

Well, Entrepreneurs often challenge this notion of “Why” to “Why not”, but there is a transition phase between the two states, which often gets missed out in the startup ec(h)osystem discussion.

That is, ask “How”.

When to answer “Why”, before ‘how’?

When your hypothesis has been validated. That is, you started with a certain hypothesis that ‘my target segment will buy <my product>, if <clause>’ and you have validated the hypothesis to a large extent.

Answering ‘Why’ will actually help you in getting the value proposition out.

When to answer ‘How’ before ‘why’?

When there is a lot of uncertainty regarding the product, answering ‘why’ could (and I say, could) turn out to be a never-ending-loop. You might be looking for data that doesn’t exist, you could be looking for customers who are still asking for ‘faster horses’.

So what’s the other way to tackle this? Answer ‘How’.

How can I make people buy bus tickets online (an idea which sounded damn crazy till redBus was launched).
How can one make people ‘share thoughts’ without the notion of blogging? the micro way of doing things?

In the early days of your startup, you will often meet people who will ask ‘why’, i.e. why would users use your product? Why would consumers install your app etc etc? And chances are that you may not have the answer. You may not have enough industry insights/connects to answer the ‘why’.

So what’s the next best alternative? Answer : How.

The real question for an entrepreneur is HOW. That’s your first hurdle to cross. And once you have done that, you will notice why turning into why-not.

Long story short: Do NOT get carried away by your inability to answer “WHY” when asked by industry pundits. Focus on “HOW”.

How equates to call-to-action, while Why could be a blue sky visioning.

How has to drive Why and sometimes, you anyhow need to get to How to start off.

For instance, “How do I sell bus tickets” leads you to explore how people are buying now, and discover what you could do different. You could develop new insights to the why. And maybe you will ditch the idea, but the experience of going in the offline world, talking to operators etc will enrich you more than doing a mere excel sheet calculation of answering why.

Thoughts?