How a Silicon Valley Entrepreneur from Pakistan Reinvented Himself

Umair always loved Mathematics and pursued it with a vengeance in school, but also had teachers who helped him appreciate the role of the arts in his life. Going to work as a high school teacher himself helped him learn how to manage and motivate large groups, reinforcing the need to be innovative so his teachings would add value rather than be forgotten with the pages of a textbook. Given his interest in Mathematics and Engineering, MIT was where he ultimately wanted to go.

Working with people is what he did best and life at MIT constantly challenged his skills as a collaborator and a leader. Umair Khan learned many lessons in college life, some more difficult to digest than others. By the time Umair and wife were both Grad students, they had just had their first child. He laughs and remembers that if you can raise a child when both parents are Grad students, you can do anything. Life was chaotic to say the least, full of time, logistical and management challenges. Exactly the kind of training needed to run a startup in Silicon Valley.

But something happened in 1995 that steered the direction of Umair’s life towards the entrepreneurship. A small but niche company, Sapient Corporation, invited Umair to join them right after his Graduate studies but he opted to work at Intel, a giant everyone knew of. 1995-1999 were the golden years for the industry and he really hit the ground running. Almost a year later he got a $1000 bonus which, after taxes became $592.

He didn’t understand the higher tax rate on bonuses so he leaned over to the next cubicle to ask his colleague, when he noticed a financially healthy-looking graph on his screen. It was Sapient Corporation that had just gone public. That day, sitting there, it became clear what had happened – he had chosen Intel for the extra $2000 in salary, yielding me a bonus of $592 over the 6000 shares Sapient was offering, which then, would have been worth between $200,000-300,000. And that just blew his mind.

You’re listening to TNS Connect and my name is Rabia Garib.

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From the Top
The building blocks of his life were set up in Karachi where he studied at Habib Public School through O’levels, then moved to Karachi Grammar School before going to MIT. He also met his future wife in Karachi, whom he married after they both completed their undergraduate studies, and so was settled in life before taking on the startup world. While Habib Public was the tough, boys-only school that forced you to be street smart, Grammar was at the other extreme, exposing Umair to a different socio-economic class.

But what helped him most professionally was what he was doing in the one year after he graduated high school, and before coming to the US. Umair was a 17-year old, teaching Mathematics and Additional Mathematics to 15 year olds at The City School on Hali Road.

Over the course of one year, he taught and gave private tutoring to those who needed additional help at virtually no cost. Nearly all his students ended up doing very well. Umair was having his first entrepreneurial experience quite by coincidence. He was essentially leading a team of 30 to 40 people, figuring out the social dynamics of the group, motivating those who weren’t performing and further challenging the ones who were. It was a crash course in most things he would need to know about managing a team.
His first-day teaching was actually quite a challenge. He went in to interview for the job and was asked to fill in for the Math teacher. None of the students really wanted to listen to the “new guy”, who was fresh meat. They said they had no textbooks with them and made other excuses to get out of the lecture. Instead of ‘teaching’ the subject, he shared a blueprint of how O’ level Math would be the key to their success in life and explained to them how life could turn out because of this subject. There was pin drop silence broken only by one student asking if he could go into another classroom and borrow a textbook so they could start the lesson. It was thrilling. That standing in for the regular teacher was actually Umair’s interview and he landed the job. This first day was also the experience he wrote about in his college essay. This narrative was at a completely different level than what most others were writing about in their applications: this was real life, a demonstration of how Umair could handle a tough situation and influence a group of kids to think about their future.

In its essence, entrepreneurship is simple. It’s all about persuading people and everything else becomes secondary. You connect with people, empathize with them and persuade them. Whether it’s your co-founder, your first employee, advisor, investor, your first partner or customer, you have to persuade them to believe in your idea and in you. That makes an entrepreneur part of a rare breed: the sincere salesperson and someone who truly believes in an idea and can persuade others to believe in it. This is something that you can only learn from the Arts, Humanities, Literature, Language and other Social Sciences.

The challenge, especially in Pakistan, is to develop this appreciation of reality and of the humanities in a system that is trying to stuff figures, dates and names down your throat via rote memorization. This might actually be a natural filter mechanism: if you can still develop the basics of creating, innovating, communicating and managing despite the system, you’re probably going to end up breaking the mold.

MIT gave Umair what is known as the ‘fire hose education’ where there’s no spoon-feeding and you either sink or swim. I remember him saying, “If you are smart you will never sink. If you are egotistical, however, you will sink because no matter how good you are, there is always somebody better than you, something that can drive you nuts. If you’re there to learn, you’ll do well. In case you’re there to prove to the world that you are the best, as was the case with many of us, it’s going to drive you insane. You quickly learn to know your limitations and be very resourceful.”

Umair was studying Math and Computer Sciences and loved his time at MIT. The college had a significant Pakistani population, which was very helpful to tap into as a freshman. But then the best thing happened to him: he got his last choice for dorm selection in a seemingly dark and decrepit building where he didn’t know anyone (none of the Pakistani’s lived there), pulling him completely out of his comfort zone. At the time he thought the worst had happened. In three months, he fell in love with being in a place where he could meet and connect with the diversity that was MIT. While most people seek out others they have commonalities with, college is a social environment that pulls in people from diverse backgrounds who can help expose their lives and experiences to you.

When you start your own business, of course, you want to reach into your community and network and pull in people from there, but what you need is the confidence to search for people who compliment your experiences, not mirror them. From the time he was teaching in Karachi till the time he graduated from MIT, Umair had become extremely comfortable in stepping out of his comfort zone, of interacting with diverse people and persuading them towards his ideas.
Silicon Valley is heaven for entrepreneurs. There is nothing that compares with the entrepreneurial energy – the buzz – in the Valley and the resources here to go out and achieve the unimaginable success are incredible. But if you can’t operate out of your comfort zone and be part of the risk-taking culture, you may not do so well.

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From Cubicle Khan to Clickmarks and Beyond

Being in an established company can be a great learning experience before you take the leap into the world of entrepreneurship. In addition to detoxing what immaturities might still be left over from the student life, it exposes you to different functions within a business, if you are willing to put in the effort to do so. It also gives you time to build the courage needed to leave the stable job and a Green Card to jump off the cliff.

Umair hooked up with Safwan Shah and worked on building, an online platform that inspired online community and discussion. In 1999, he made the decision to start on his own and this was the start of Clickmarks.

Clickmarks started off as a shareable bookmark service like Delicious or Digg is now, but about 8 years before the Facebook/iPhone generation had arrived. They raised $27 million in funding over four years, which, in retrospect was not as conducive to success. It restricted them in what they could do with the company in terms of an exit.

An entrepreneur really has to have ridiculous ambition and intense humility and the challenge is to find the balance: If you have ridiculous ambition and are arrogant, you’re dead. If you are too humble and undersell yourself, you’re dead.

Trying to do too much with a business is perhaps the quickest way to kill a business. Umair and his team could only do so much with limited resources and the capabilities they had. With the investments they were landing, they just ignored that reality. In Q4 of 2000, Clickmaks was making a million dollars in revenue a quarter with only 20 people. One of their VCs then insisted on bringing in seasoned management because they felt the impending high-paced growth phase would be too much for young Umair to handle. With seasoned management in, Clickmarks grew from 20 to 80 people and expanded out to offices in LA, New York, Atlanta, UK, Spain, etc., but went from a profitable million dollars a quarter to $3 million a quarter in expenses and no revenue.

Their core focus had expanded from ‘get all your favorites in one place’ to ‘get all the content from the web out to any device’; they were using the growing team to go after all the telcos. This was before smartphones. WAP phones and Palmpilots were the hottest platforms, and Clickmarks was taking all the content and web services and transcoding them onto these (now primitive) mobile platforms. Vodafone was an early adopter, generating most of their revenue” Their seasoned CEO (who used to be a CFO) believed in building linearly on the financial success they had just gotten from Vodafone, by getting several other telcos. However, the early success with Vodafone was not easy to simply replicate with other telcos. And then the 2000 crash happened.

When startups win their early adopter and there is only one whale generating the revenue, they cannot afford to relax. They have to evaluate if the product and vision is scalable beyond the early adopter. If not, they must retool their product, which is capital intensive and if you only have one source of revenue in an unstable environment while you are retooling, you may have a very serious problem on your hands.

It was a Wednesday night late in 2000 when Umair felt more overwhelmed than ever before and needing a break he found himself sitting in an almost-empty cinema theater watching “The Lord of the Rings”. He recounts: “It was nearly midnight and the middle of the week, and I remember watching the movie initially with forced interest… until I heard Frodo Baggins tell Gandalf, ‘I wish none of this had ever happened, I wish the ring had never come to me.’ And Gandalf turns to him and says, ‘So do all who live to see such times, but that is not for you to decide. All you have to decide is what to do with the time that is given to you.’ I remember sitting bolt upright in that theater at 1 am, and I knew exactly what I was going to do.”

Umair called a meeting of the Board soon after and laid out the plans for revival.

Want to know what happened next and where Umair is today? Read the rest of the of Umair Khan’s story at the link in the description. Share your thoughts on where you think a company like Clickmarks would be today? And of course, share what your key takeaway is from a story like this one.

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This episode of TNS Connect was brought to you by The New Spaces. Until next time, this is Rabia Garib.

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