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Apoorva Dutt · · 8 min read

Want a career in tech? Study the arts, says this venture capitalist

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The following is an abridged excerpt from The Fuzzy and the Techie, authored by Scott Hartley, a leading venture capitalist and global startup adviser who has worked at Google, Facebook, and Harvard’s Berkman Klein Center for Internet and Society. The excerpt is published courtesy of Penguin Random House.

Shoaib Makani, with his Bollywood good looks and broad smile, was working for an Indian billionaire, helping him invest in the latest technology start-ups, when he quit his plush job to start his own technology company focused on delivery trucks. He didn’t have experience as a technologist or in driving a truck, but he’d observed the evolution of efficient marketplaces that used technology, and he’d gained an appreciation for logistics.

A Pakistani-American, Shoaib grew up in Texas, studied government at the London School of Economics in England, and began his career working at a mobile ad-tech company called AdMob in Silicon Valley. Through a stroke of good fortune, Google had acquired AdMob, and Shoaib soon found himself on the investment team of the opinionated Indian billionaire and co-founder of Sun Microsystems, Vinod Khosla.

Though he had a degree in political science, Shoaib was the one evaluating the technology of hundreds of founders, and he soon began to form his own opinion on what really made a great business. The tech was important, but it wasn’t everything. He had something not all people are born with: grit, passion and an ability to sell his vision, and he learned that he could easily hire those who could build the tech.

Shoaib left the investment world to found KeepTruckin’, a service that allows truck drivers to electronically manage their logs of when and where they deliver goods. Along with his brother-in-law, Obaid Khan, whose family had emigrated from Islamabad and Karachi in the 1970s, they had been in search of a good business. Obaid had an “aha” moment when sitting in a filthy truck, having a conversation with its driver.

As the driver complained about his job, and a new federal requirement mandated by then president Barack Obama, Obaid remembers how “a light bulb went off to make him realize that this was an opportunity”. KeepTruckin’ uses a mobile phone application to allow truck drivers to update their duty status, and comply with hours of service regulations for commercial drivers.

Shoaib and Obaid are both “fuzzies”, students of political science and government, who came from broad liberal arts backgrounds, whose non-linear approach to starting a company is by far the norm rather than the exception. Shoaib had become a domain expert in marketplaces, and he observed trends and efficiencies in advertising technology that he thought could be applied to electronic freight and logistics.

Shoaib might be an unlikely character to be at the helm, but it was exactly his liberal arts prowess that set him up to succeed

As one of the world’s largest industries is on the cusp of change, Shoaib might be an unlikely character to be at the helm, but it was exactly his liberal arts prowess that set him up to succeed. He saw the big picture, knew how to study a market and ask the big questions, learn the nuance of government regulation, and sell his vision through charisma, communication, collaboration, and a strong sense of empathy.

He was able to identify a market need because he had talked with hundreds of people, and learned their pain points. He had a deep sense of empathy for who they were and what they needed.

While Tesla and Mercedes are debuting expensive driverless trucks, this transition away from old durable goods will take decades, and in the interim, the winners will be the Shoaibs and Obaids of the world.

These are the people who don’t blindly believe the hype that “the robots are coming,” nor are they intimidated by engaging with new-found technology, but they are also the ones who see its broader purpose in helping solve problems that are deeply human. The biggest problems are those that require seeing the big picture, having a strong sense of values and purpose, and empathizing with others.

Today KeepTruckin’ has raised over $50 million at a half-billion dollar valuation, and has over 300 employees in Pakistan.

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Apoorva Dutt

Content creation, marketing and consumption.