Inflection (Book Excerpt) by Nilesh Shrivastava & Pushp Deep Gupta

Real careers are not perfect. Professional success is not absolute. People shape careers and then over time, careers shape people.

Feb 1999. The batch of 1999 steps out from one of India’s leading business schools—Indian Institute of Management, Kolkata—into the real world of careers, not unlike many other professionals before and after.

Eighteen years later—in the middle of their working lives—32 of these professionals pause and take stock.

They look back on their careers, on the choices they made, their successes and their failures, their highs and their lows.

They reflect on what they assumed when they graduated from B-school and what the world has taught them since.



This is the story of real careers taking shape in the rapidly evolving post-liberalisation India of the last two decades. Of conventional careers and not-so-conventional careers and something in between. Of people who took the corporate path, who became entrepreneurs, who became academics, who went abroad, who became specialists, and even those who let their careers go with the flow, unplanned. Step in as they take stock of their journeys.

As relevant for mid-career professionals, to peek over their shoulders at peers, as for those starting their professional careers, curious about the careers choices ahead and the road signs on the way.

Nilesh Shrivastava has been working in the financial sector for the last eighteen years and currently heads the South Asia financial sector investments portfolio at International Finance Corporation, part of the World Bank Group, based in New Delhi. Earlier, he was with a leading foreign bank in Mumbai. He has also continued with his interest in writing and is the author of two fiction novels: “No Man’s Land ” (published 2014) and “The Second Hand” (published 2009).

Pushp Deep Gupta is Executive Director at Deloitte Consulting in Leadership Advisory, based in Singapore. Pushp is a career human resources professional and has eighteen years of experience in working with global and regional clients in the areas of Talent and Leadership consulting.



If you are making mistakes, it means you are out there doing something

–Neil Gaiman, ‘Make Good Art’

In 1999, business school was like a pit stop on the way to a corporate career. It certainly wasn’t the route to a personal venture, for the most part. There was no course on entrepreneurship in most B-schools in India then. If someone ventured out on his own, support was at best limited—be it via capital, role models, or advice. The trend of people opting out of placements to start something of their own was still a few years away. Even though there was a job for everyone on campus, there were a few who had already made plans for stepping out on their own; some more overtly than others. Risk takers exist everywhere as they did in the 1999 batch, and we thought it best to start with what was more of an exception than the norm at that time. Hopefully, that started to become more of a trend line in later batches.

“Risk takers” does not simply mean those who started a website of their own or hatched a business plan while on campus. The lack of an active venture ecosystem—both on and off campus—prevented such a drastic move. Risk taking then took on several shapes. In most cases, the people joined their campus jobs for a while but were clear that the relative safety of large corporates was not what they aspired for. Even in the first couple of years, many of them stepped out of their comfort zone and hitched up with ventures that were not established, ideas that were nascent, or simply looked around for businesses where they could play a lead role—often without the comfort of a brand, or even a steady salary.

There was also a macro trend that had just become apparent in the last years of the 90s. The internet had begun spawning innovative businesses in the west. While Google and Facebook were still a few years away, Yahoo! had become a sensation and shadowing it, there were some early startups beginning to take shape in India, spurred by eyeball tracking valuations and hopes of massive growth. If there was a good team and an innovative idea, there were a few venture and angel investors willing to take an early bet, albeit in a measured manner. Telecom and internet services, while still evolving, allowed for some IT based businesses to claim a large consumer base. This was a marked departure from even a few years ago, when a new business essentially meant brick-and-mortar and the accompanying need for heavy capital and resources.

A more unspoken but implied attraction of such innovation-based businesses was that they did not need a long list of government permits, high level contacts, or any standard traits of crony capitalism inherent in rent-seeking industries. Companies like Infosys, which were started by a group of engineers had proved it was possible. Those from a middle class background in a B-school could at least dream of starting or joining a fledgling venture with just the strength of their ideas to back them, even if their immediate ecosystem wasn’t too encouraging.

We profile three such early risk takers—all of whom took different paths on their entrepreneurial journey which continues to this day. One had spectacular success in his first venture while subsequent efforts have been more tepid; another had moderate success early on but feels more assured and confident of his current venture, while the last took on the challenge of a brick-and-mortar business almost accidentally and slowly but surely has begun to thrive in it. Different journeys for each, which stand out even more starkly compared to the late stage entrepreneurs we met (described in a later chapter), who took the plunge only after several years of corporate life and building a much stronger foundation—both financially and professionally.

The three batchmates we met up with were:

Nitin (Andy) Jain: Andy hails from Ludhiana and was quite visible on campus riding his Bullet motorcycle (one of few on campus, at that time), and audible for his love of high decibel remixes. He joined an online poker company called Partygaming early on, which went on to become a very successful LSE IPO hitting company with multi-billion dollar valuations. He then started another venture in the sports and media space and is currently an active angel investor based in the UK.

Manikandan: Apart from academics, Mani was active during his IIMC stint organising management fests, which included sponsorship hunting. Known for his prowess with the guitar and backhand table tennis returns on campus, Mani started work in the IT services space and then joined his in-laws’ family business of making educational toys for the Montessori/pre-school space. He has now branched out into offering turnkey services for pre-schools and is among the largest players in the segment, based out of Bangalore.

Vikram Kumar: Tall and lanky, Vikram joined the campus after a stint in the software services field. Another of the rare owners of two-wheelers on campus—his scooter was rumoured to be somewhat slower at full throttle than sleepy pedestrians. Vikram was among the first to join the internet boom players working with He then built an early player in the marketing analytics space, growing it for nine years to scale. Post-2009, he set up a second venture focusing on using artificial intelligence in healthcare marketing and is now growing the business with a product-based approach having bagged his first round of VC funding from Norwest Venture Partners—a leading Silicon Valley VC. He is based in Hyderabad.


The initial influences that bent the three of them towards entrepreneurship were different from one other. Andy came from a family of CAs based in Ludhiana and his environment always had entrepreneurs of all shapes and sizes around him. He says he “always wanted to do something on my own” so much so that in his first attempt at IIMs, he would openly state his interest in setting up his own shop at the interviews. He quickly realised that neither the interviewers nor the B-schools thought much of people flying off on their own to begin with, and quickly changed his track to more of cookie cutter responses (“I want to add value,” “grow with a company” etc.!).

Mani and Vikram, on the other hand, came from staid service class backgrounds where it was “not in our blood to do business.” Mani’s father was a career banker, while Vikram’s father was with a public sector company based in Ranchi. While Mani did have it in the back of his mind to do something on his own, it was not apparent or clear what it would be, at least not at the B-school stage.

Vikram’s first impactful influence came in during his first job post-engineering, in TCS Chennai. It was here he came across a person with a respectable IIT background, who had quit a UK-based job (and salary to go with it), and come back to set up a cricket-based website. Vikram’s first reaction was one of incredulity; who in his right mind quits a snug overseas salary to follow a random passion for cricket especially at a time when half of Chennai seemed to be trying to get an IT job abroad! It was only a year later when internet businesses were picking up that the cricket website (it was was back in the news as a success story hitting millions in valuations. It was Vikram’s first flavour of the new economy business and that there was something in it.

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