The Caravan – August 2019

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AUGUST 2019 85

on the evening of 9 april, a select
group of Delhi’s dapper elite gathered
at the ballroom of the Hyatt Regency.
After about a half hour’s socialising,
aided by an assortment of teas and
starters, Chiki Sarkar, the co-founder
of Juggernaut Books, introduced the
evening’s speakers.
“Whenever we now think of Rajat
Gupta,” she said, “we think of a simple
question—did he or didn’t he?”
Juggernaut was releasing Mind With-
out Fear, Gupta’s memoir, which charts
his rise to becoming the first Indian-
origin managing director of McKinsey,
and his subsequent felony conviction
in a high-profile insider-trading scan-
dal that shook business circles in 2012.
The conviction resulted in a two-year
prison sentence, which Gupta com-
pleted in 2016. After his release, Gupta
sought to overturn his conviction, but
in January this year, the Court of Ap-
peals for the Second Circuit—one of
the United States’ 13 appellate courts,
which includes judicial districts in New
York, Connecticut and Vermont—ruled
against him. His memoir, and its ac-
companying media campaign, seemed
to be a final attempt at public rehabili-
tation.
Until his conviction, though, Gupta’s
story was the quintessential template of
corporate success that Indian parents
envision for their children before pack-
ing them off to an engineering college
and, later, a business school. He was
born to a middle-class family in Cal-
cutta, in 1948. His father, Ashwini Ku-
mar Gupta, was a journalist involved in
the freedom struggle. The family soon
moved to Delhi, where Ashwini helped
start the Delhi edition of the Hindu-
stan Standard, which was, incidentally,
owned by Sarkar’s family, as part of
their Ananda Bazar Patrika Group.
Gupta was orphaned at the age of
19, when he was still a student at the
Indian Institute of Technology, Delhi.
He began caring for his siblings with
the help of an aunt who moved into
their home, which he visited every

weekend. Gupta ran the household on a
strict budget while carrying on with his
active campus life—he was a member
of the dramatics club and head of the
student government. In his final year,
he applied to business schools while si-
multaneously sitting for campus place-
ments, bagging and then rejecting a
coveted job at what was then the Indian
Tobacco Company—now ITC Limited—
for Harvard Business School.
“One of the things that memoirs do
is that they show you the man behind
the CV,” Sarkar said. Mind Without
Fear, she added, “tells you the story of
a shy, diffident young student who goes
to Harvard Business School, and when
he first goes, he finds that he’s lag-
ging—he’d always been a very brilliant
student—because he doesn’t speak up as
much as the other Americans do.”
Gupta would overcome this and other
tribulations to land another enviable
position right out of Harvard—that of a
consultant at McKinsey and Company,
reverently known in the management
world as “The Firm.” There, he recalls
in the book, Gupta proved himself mul-
tiple times over the next twenty years,
eventually securing election as the
managing director in 1994.
As applause for Gupta subsided at the
launch, Sarkar introduced his inter-
viewer for the evening: Madhu Trehan,
the founding editor of India Today and
a co-founder of the news website New-
slaundry. Trehan warned the audience
that despite the empathy she had for a
man who had been through so much,
it was her mandate as a journalist to
ask tough questions. She quoted an old
friend of Gupta’s who had commented
that ever since Gupta finished his third
term as managing director, in 2003,
and returned to being a senior partner,
his “sense of having lost sway and influ-
ence was palpable.”
Gupta clarified that it was he who
had instituted term limits for the posi-
tion, believing that every leadership
position benefits from change and a
rotation of responsibilities. “So I wasn’t

hankering for the loss,” he said. “I
could’ve become CEO of a number of
different organisations, but that was
not my objective. My objective was to
put the skills I’d learnt, the leadership
skills I’d developed and the network I’d
developed to actually work for the good
of society.”
During this period, Gupta co-found-
ed the Indian School of Business; the
American India Foundation, with the
former US president Bill Clinton; the
Global Fund to Fight AIDS, Tuberculo-
sis and Malaria; and the Public Health
Foundation of India. Around the same
time, he became friends with Raj Raja-
ratnam, a Sri Lankan Tamil and fellow
immigrant to the United States. This
friendship would lead to his eventual
disgrace, as Gupta was indicted for his
business ties with Rajaratnam.
In the early 2000s, Rajaratnam was
a Wall Street star and the owner of a
multibillion-dollar hedge fund called
Galleon. He had a reputation for being
a talented trader with an incredible
work ethic. Gupta met Rajaratnam
through Anil Kumar, a senior McK-
insey partner whom he had mentored
and set up ISB with, and who had gone
to business school with Rajaratnam.
After consulting his close friends Hank
Paulson and Gary Cohn—both holders
of top economic posts in the US gov-
ernment and, respectively, the chief
executive and president of Goldman
Sachs—Gupta acted upon their positive
endorsement of Rajaratnam’s character
and entered into an investment with
him in 2005.
The investment fund was called
Voyager, and it was worth $50 million.
A year later, Gupta and Rajaratnam
started a new venture called New Silk
Route, aimed at investing in Indian
companies. New Silk Route was to have
two halves—one dedicated to private
equity, and another to hedge funds—
with Gupta as chairman. However,
investors seemed to be against this
two-pronged strategy, and there was
spencer platt / getty images talk of carving out the hedge-fund wing


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