High flyer: Ruparell on top of Groupon’s Chicago offices
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When talking about his career and education, Rajen Ruparell tends to favour words related to speed, mainly variations on “hustle”, “accelerate”, and “hyper”.

On the covert pizza business he ran during his undergraduate days at the University of Toronto: “We expanded to almost six universities by the end of my fourth year, so it was kind of fun – we were just hustling.”

On a key lesson from Imperial College Business School in London: “Find your niche and your brand and [use] that to accelerate in the business world.”

On CityDeal, the daily deals website he co-founded and sold to Groupon five months after launch in an estimated nine-figure deal: “At CityDeal, I learnt a whole new form of business, which is about hyper-growth – it was everything.”

As the head of global sales for Groupon, the online deals company, at the age of 30, Ruparell knows a thing or two about moving quickly. He is sitting in one of the conference rooms of Groupon’s 146,000sq ft fourth-floor riverfront office building, housed in the former warehouse of Montgomery Ward, Chicago’s famed mail-order catalogue company.

Out in the sales pit, a hive of Groupon salespeople buzz over phones, working with merchants throughout North America on deals for laser hair removal and half-priced sandwiches, architecture tours and sailing lessons.

Ruparell talks fast, and he has moved fast to get where he is. That sense of urgency is what led him to enrol in the inaugural MSc in management course offered by Imperial in 2005.

“For me, this was an opportunity to go straight from undergrad into a one-year programme, be finished when I was 22 or 23, and accelerate from there,” he says. “It was a split-second decision. I knew I got in in late August and I was on a plane two weeks later.”

Imperial’s focus on entrepreneurship appealed to Ruparell. He comes from a long line of businessmen, stretching back to his great-grandfather’s generation, Indian immigrants who operated cotton gins in east Africa. Ruparell’s father moved the family to Calgary, Canada, in the 1970s in order to attend business school there, and eventually his brothers joined him. The extended family went on to have a hand in everything from hotels to property, with a core focus on their chain of car dealerships.

The informal education Ruparell received at the family’s flagship Nissan dealership, first as a teenage car washer and later as a salesman during summers off from university, helped prepare him for Imperial.

“Imperial was an automatic fit for me – out of all the schools it was so entrepreneurial,” he says. “The coolest part of the programme was that it was intended for undergrads who didn’t have a business background, so it was very diverse.”

Ruparell’s background was firmly in business, but the programme offered him the opportunity to formalise those skills. Most of the MSc courses replicated those offered to MBAs. He suggests this may be because the programme was in its infancy and administrators were still trying to work out exactly what to do with the entrepreneurial students. But he says that unlike a traditional business education, MSc students spent most of their time working in groups of seven or eight.

“That’s where I realised that people have different natural skillsets that are like pieces of a puzzle,” he says. “And if you have all the pieces of the puzzle, you can be very successful.”

That does not mean that many of his fellow students followed Ruparell down the path to entrepreneurship. Most entered consulting or finance.

London is a very expensive city; people have just paid a boatload for their education and so they follow that [more traditional] path,” he says.

Ruparell never really had that choice. As part of his decision to attend Imperial he made a deal with his father to return to the family business for a couple of years. He soon found himself on a flight back to Calgary, but not before founding his own start-up at Imperial, after two websites changed his perspective on what he wanted to do. The first was Facebook, which “blew my mind, partially because I could check out a picture of the pretty girl I had a crush on”.

The second was The Million Dollar Homepage, the brainchild of Alex Tew, a 21-year-old who sold advertisers 1m pixels for $1 each on a static web page in 2005. “It fascinated me – this kid, 21 years old, made a million bucks via the power of the platform, the internet,” he says.

Ruparell set out to copy it with his ninthworldwonder website. It involved a map of the world on which companies could purchase countries as a marketing move (Sapporo, the brewer, might buy Japan, for example). He and his partners sold a few countries but the idea flopped.

It did, however, alert Ruparell to the potent relationship between innovation and imitation. “It fascinated me to learn [at Imperial] that most of the great ideas… had been based on previous ideas or previous failed executions,” he says.

After a two-year stint managing his father’s Nissan dealership – where he could put the basic accounting, sales, finance and marketing skills he had learned at Imperial into practice – Ruparell returned to the UK to work, briefly, at Oxford Capital Partners, a venture capital firm. Three months in, he was called back to Calgary one last time to help his father sell the car business.

When that deal closed, he flew back to Heathrow and upon landing called Marc Samwer, whose German family-run fund has made a fortune by copying dotcom ideas that have worked in the US and implementing them elsewhere with an eye to selling the ventures. The three brothers made their first millions by selling a German version of eBay, the auction website, to that company in 1999.

Their business model of cloning existing ideas and selling them to their originators has garnered the Samwers a fair amount of criticism in tech circles, and a whole lot of money. Ruparell says he considers Marc Samwer to be one of the many great mentors he has had, including Andrew Mason, Groupon’s recently ousted chief executive, and his successor, co-founder Eric Lefkofsky.

By 2009, the Samwers were looking at a European version of a new US site: Groupon. That was exactly what Ruparell had called to chat about, and soon the Samwers had put him together with a group of young Germans to create CityDeal, which launched in January 2010.

Five months of development at a blistering pace, including day trips across the UK and Europe to convince merchants of the merits of the service, and CityDeal was scooped up by Groupon in a deal estimated to be worth more than $100m.

Ruparell was charged with growing the company’s international business, launching Groupon in dozens of countries. In order to gain access to top talent, Ruparell tapped his Imperial alumni network. A mass email led to more than 100 introductions and a number of hires, some of whom, Ruparell says, remain with the company.

Groupon has struggled since going public in 2011, and though Lefkofsky’s appointment as chief executive seems to have pleased investors, shares languish at less than half the price they listed at. One bright spot in the business is Groupon Goods, the company’s first foray into retail, which Ruparell was assigned to build and run

“That was very exciting – I got to build another start-up, but with all the learnings [from] the first time,” he says. It accounted for roughly 40 per cent of the company’s revenues in the second quarter of the year.

Ruparell says he does not demand MBAs or formal business training of his appointments, though he does see value in programmes such as Imperial’s, which he says was ahead of the curve when it came to incorporating practical learning.

“The shift still needs to be made in business education to allow people to have significant levels of practical experience,” he says.

Part of that shift may involve an acknowledgment that some young graduates will forgo an MBA or MSc in favour of a job in the tech world.

“There are alternatives [now] – five or 10 years ago there weren’t companies that you could go into and accelerate very, very fast,” he says. “Hyper-growth has changed the world significantly: we’ve built more billion-dollar companies in the past 10 years than we ever built before.”

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