Silicon Insider: The New World of Startups

Jan. 25, 2007 — -- Every true entrepreneur faces a moment of personal reckoning.

For Santosh Jayaram, that moment came last week.

For the last 18 months, ever since he earned his MBA from Oxford University, he has devoted almost every waking hour of his life to trying to create a new company. He moved back to San Francisco, where he had once been a salesman for a tech company, reconnected with a couple of old acquaintances -- Indian immigrants like himself -- and set to work. Each morning he said goodbye to his wife, Dawn, as she drove off to work, then settled into a local coffee house with his laptop and got down to business.

Santosh's initial notion for a new company involved local wireless connections for municipal governments, an idea that foundered in the face of difficult technical problems and almost insurmountable political challenges. Three months of 80-hour weeks, scores of interviews and long nights of research… and Santosh walked away without looking back.

He might have given up then. After all, most of his classmates had already settled into high-paying and prestigious jobs in industry, finance and venture capital. But Santosh had found his calling. He was an entrepreneur. And he sat, day after day, sipping his coffee, surfing the net, still wearing some of the increasingly ratty clothes he'd bought in college, soldiering on in search of another great idea that could be turned into a viable company.

He found it several months later.

While at Oxford, Santosh and Dawn had taken hundreds of photographs -- of the school, of England and of their vacations on the continent. Now those photographs sat, disorganized and mostly unshared with friends and family on Santosh's desktop. He had long ago concluded that too much time had passed, and that he was just too busy, to ever send them out. Worse, he was continuing to take photos, all destined for the same fate -- until, like some of his friends, there would one day be thousands of photographs, unseen, unshared, clogging his disk. He already had friends in that predicament.

Making matters even more painful was that Santosh, like his friend Ayush Gupta was an immigrant -- both young men had left families a half-world away. As good sons, they felt guilty that they were not staying in touch with home often enough; by the same token, letters -- and more importantly, pictures -- from home were few and far between.

Almost every important new technology product and service has its beginnings with the angry question: Well, why the hell can't we do that?

That was the question Santosh asked about photosharing in early 2006. Finding the answer led Jayaram, Gupta and a third friend, Supreet Singh, to create a new company, called Powersnap, and to spend a year sacrificing almost everything they had in the quest to make that company and its product real. As with any startup operation, it was exhausting, physically and financially.

Now, late on a night in mid-January, just a week before the formal public announcement of Powersnap Alpha to the world, Santosh hit the wall. He was exhausted, sick and broke. He hadn't slept more than two hours per night since Christmas, and even that sleep was fitful because he was worried about his baby son -- just to put the maximum stress on themselves, both Santosh and Ayush had recently become fathers -- who was also coming down with the same flu bug. Having dug himself in so deep, what happened, Santosh asked himself, if the product failed? It was an entrepreneur's classic 3 a.m. moment.