Bitten by the e-bug

So what do I think?

I counter-question him: But why?

We discuss the pot at the end of the rainbow and we agree that now companies do afford a reasonable opportunity to create enough wealth to afford a home in Alibaug and shopping at the Ponte Vecchio, but perhaps not what he calls “serious money". Is it a desire to make his mark on the world, and the belief that his business idea will be transformational? Or does he want to be the master of his own destiny, to be his own boss, to build something? Does he want to be free from corporate shackles, to prove that he can do it? Or perhaps, is it just the good old-fashioned desire to better-thy-banker-neighbour, who listed at the peak of the capital market boom?

Well, all are good reasons.

We run through the big idea, whether it’s been done before, the market potential and what’s different. Why he is well positioned, well skilled to take this on and why now, when his star is rising and his credibility is high, is this potentially the best time to do it. We take a realistic look at roadblocks—regulatory, competitive and financial. We discuss the potential, the cash flows, the value versus valuation proposition, the base business plan. He reveals that he’s had initial commitments around base funding. Six months ago. And yet he is still on the fence.

So then, why doesn’t he make the leap?

Clearly, there is risk. Of losing one’s shirt, of not being able to scale up, of running out of money, of the economy tanking again, of a “big brother corporation" copying the idea and blowing him out of the water. Perhaps, more importantly, given his position, the social and possibly very public risk of failure.

Then there is the lifestyle change, I remind my friend. Club class travel, red carpet events, business club memberships, the World Economic Forum passes. And the risk that he may not be able to climb back on the carousel, if it doesn’t pan out. Does he find this conversation scary or inconsequential?

Given that he has the management breadth and the industry knowledge, does his own core skill really lie in galvanizing and growing large corporate platforms and doing big-ticket deals or could he bootstrap, readjust himself to a small company or a start-up mindset? Does he have the self-confidence and the discipline? His family’s support? The ability to weather the loneliness of the journey?

But most importantly, I asked him to look within and assess if he had an entrepreneur’s DNA, that bug, the burning desire? The sheer bloody-mindedness and doggedness that it takes to keep believing when the chips are down, to get up and rejig, rebuild, try again—or know when to quit? While he clearly wants to operate independently, was he ready to also carry all the responsibility and risk? Could he carry people, make them believe the dream? The acceptance that there would be no work-life balance, that work would became life if he become an entrepreneur?

I told him of an entrepreneur I first met in the early 1990s, when he ran a small clothing store with a funny name, who described his grand plan to me at a coffee shop. At first I was sceptical—shopping malls, department stores, discount stores in India, and him? And then, as he drew out his dream, eyes shining, I began to believe that if anyone could do it, he could. And almost a decade later, when he called to say he was ready to hire professionals, we were right there. However, it took him 15 years, in a booming—and protected—market to become the king of retail. I asked my friend if he had the patience, the planning skills and the energy for that?

There are no right answers to my quiz, but as they say about those Fratelli shoes across the piazza, if you have to ask, you probably can’t afford them. If all these questions don’t sit well, then you’re probably not yet ready to become an entrepreneur. And that’s not necessarily a bad thing at all. But the dholkis are sounding out at the Duomo, so that’s for another time.

Sonal Agrawal is chief executive, Accord Group, an executive search firm.

Write to Sonal at careercoach@livemint.com