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Don’t Just Start With Why, Lead With It

Cameron ConawayLast Updated: March 31, 2016


Inspiration struck Vikas Gupta in 2012 when, after quitting his job as Head of Consumer Payments at Google to travel the world, he was hiking with his wife in the French Alps. With his 9-month-old daughter strapped to his back, the vast blue, white and green landscape before his eyes, and the freedom of not having to think about work, this simple truth washed over him:

The time I spend at work is time away from where I most love to spend it—with my family. So I came to see work hours as absolutely precious. If they were taking me from my family they had to be meaningful.”

So Gupta decided that his future work would be about making the world a better place for children.

In other words, he found the why of his reason for working before he could articulate the why for any future company he’d create. And it’s this mindset that he infuses into his role as CEO of Wonder Workshop, a company based in San Mateo that he co-founded in November 2012.

With only 25 people on their team, Wonder Workshop has garnered several major awards for their creation of Dash & Dot—robots that, through play, teach kids 5 and up how to code.

In addition to the honor they received from Good Housekeeping, Gupta’s team has won awards from Popular Mechanics, Scholastic Parent & Child, and FamilyFun Magazine. They were named one of Inc. Magazine’s most innovative startups of 2015, they’ve been adopted in over 1,000 elementary schools throughout the United States, and Melinda Gates recommended Dash (on the right in the photo above) as the best way for children to learn Computer Science.

And then there are the hard numbers. When Gupta first launched the project on Kickstarter, it quickly generated $1.4 million. The stream of money and interest didn’t end there. Since the company’s formal launch, they’ve raised over $17 million from Google Ventures and Madrona Venture Group, among others.

It’s the kind of startup success story that feels at once inspiring and entirely out of reach, so I caught up with Vikas to gain a deeper understanding of how that inspirational why helps him lead his team.

Starting with why, and how Gupta did it

wonder workshop 1

Left to right: Mikal Greaves: Co-Founder, VP of Product Development; Vikas Gupta: Co-Founder, CEO; Saurabh Gupta: Co-Founder, CTO

Born in Chandigarh, India, Gupta learned to program when he was 14. Learning to code was an experience that has stuck with him not only because it equipped him to enter the tech space, but because he legitimately enjoyed it.

I learned to program when my school purchased its first computer and hired a Computer Science teacher. Computer programming was fun for me from the very first moment; there was something magical about writing a set of instructions that the machine would run and produce an output,” Gupta says.

After immigrating to the U.S. in the 90s, Gupta attended graduate school and, shortly after graduation, moved into a position with Amazon, a 7-year experience that eventually led to him leading their payments and web services teams. “I had an incredible experience at Amazon,” Gupta began.

I benefited from the culture of end-to-end ownership, and loved how they believed in me and empowered me to innovate and take risks.”

When Gupta left Amazon to launch Jambool, a virtual monetization platform that enables developers to create and manage virtual currency (which he later sold to Google), it was partly because Amazon helped to nurture his ability to take risks.

When I then joined Google, I was blown away by the culture of openness. There were literally no walls when it came to information within the company,” Gupta told me.

But while Gupta was well on his way to carving out his place as an innovator, and racking up quite a resume in the process, he was primarily driven by his intellect and work ethic. He could masterfully handle the how and the what, but he didn’t really know why he was doing it all. Sure, he had the talent, often enjoyed the work, and it was a way he could support his family, but something felt missing.

When my first child was born, it just felt like the perfect time to take a break and figure out what I should do next,” he said.

Gupta didn’t set out to define his why, and he hadn’t read Simon Sinek’s Start With Why, a popular book (that grew from this massively successful TED Talk) encouraging leaders to place less emphasis on what they are doing and how they are doing it, and more on why they are doing it.

But Gupta did grant himself space away from day-to-day work, and there are many other success stories that follow a similar path.

Take, for example, the story of TOMS founder Blake Mycoskie. In its first six years, TOMS grew into a global company with $300 million in revenue. Mycoskie owned 100% of it, and for five consecutive years it had an annual growth rate of around 300%. So why then, in the fall of 2012, did he take a sabbatical?

As Mycoskie tells it in the January-February 2016 issue of Harvard Business Review, he needed to have a “physical and psychological separation from the company to do some soul-searching.”

Like Gupta, Mycoskie’s time away made him realize why he wasn’t entirely fulfilled by his work anymore: He was bogged down in the daily grind of the what and the how. Unlike Gupta, this realization was sparked by Sinek’s book:

The more I thought about this idea, the more I realized that TOMS had veered away from its ‘why.’ In the early days we always led with our story: We weren’t selling shoes; we were selling the promise that each purchase would directly and tangibly benefit a child who needed shoes. But our desire to sustain the company’s hypergrowth had pushed us away from that mission and into competing on the ‘what’ and ‘how,’ just as every other shoe company does.”

The result? Mycoskie returned to TOMS with a newfound fire, and a new idea that, as he puts it, “reinspired the ‘why’ of TOMS”: he launched TOMS Roasting, a coffee venture which, for every bag sold, provides a week’s worth of clean drinking water to a person in need. The move has led to over 175,000 weeks of clean drinking water, and has ignited the TOMS customer base back to levels Mycoskie hasn’t seen since they were the new kid on the block.

Herein lies what many people miss about Sinek’s vision, especially those who have only watched his TED Talk: Starting with the why isn’t merely a way to improve your sales pitch or even carve out your company’s vision, it’s a way to help you question how you’re spending what Gupta calls those “absolutely precious” hours at work.

For Gupta, it’s not enough to “start with why.” He uses it as a way to lead his growing team.

Leading with why, and how it helped Gupta pivot

If you’ve made it this far, you deserve this glimpse into the what.

Why for Gupta begins with the overarching idea of making the world a better place for children. This idea became more real, however, when he was able to frame it like this: The potential for children to learn to code is great; the tools available to help them do this, however, are not.

“As I read and explored this topic, I came upon an article about Estonia mandating their first graders to learn programming. This took me by surprise—I felt first grade was far too young to learn programming,” Gupta began.

How were these kids learning? Could children learn to program at that age? As I read through the research on the subject, I learned that while on one hand kids have the cognitive ability to learn the Computer Science fundamentals at a young age, the existing tools don’t serve their needs. Educators have been trying to take products for older kids, or adults, and make them work for kids at a young age, and through no fault of their own they were failing in those attempts.”

Teaching kids to code through robots wasn’t Gupta’s initial idea, though. His team spent their first few months trying to figure out how they could get kids to actually build their own robot. “We eventually realized that we were making the same mistake others before us had made, and we needed a fresh approach,” Gupta said.

To overcome this challenge, Gupta brought his team out of the what and back to the why:

Why are we trying to help kids build a robot?

This questioning led them to:

Why don’t we instead teach them to code through a robot?

The pivot turned out to be a crucial one for all parties involved, and allowed Wonder Workshop to immediately get to work on solving their three most pressing questions:

1. Is the robot usable for a child as young as 5 or 6?

2. Is it fun from the moment the family opens the box?

3. Is it affordable?

“This was a pivotal moment for us. I’m not sure if we could have made it if we didn’t keep why at the forefront, and use it as a guide to ensure we created the best team we could,” Gupta began.

If I have any advice for growing startups out there it’s this: never lower your hiring bar. Hiring well is the most important aspect to a startup’s success. Bringing in the best talent, and investing early in the culture and their growth helps assimilate new employees better, and reduces bottlenecks as the company grows.”

Why keeps Wonder Workshop evolving, and having fun

wonder workshop 3

A screenshot from Path, an app that works with Dash.

If our why is about allowing kids to learn while having fun,” Gupta says, “then it makes sense that we keep fun a part of how we learn as well.”

Aside from how having fun robots zooming around the office can lighten the mood, there’s often a ping-pong or foosball game going on at Wonder Workshop as well. They run a flat organization, frequently share company metrics with each other, and embrace open seating—which means opportunities for their mechanical engineers, electronics team, software developers, marketers, and fulfillment operations team to brush shoulders, share ideas, and connect.

They are a team that realizes the importance of play, both in how it allows employees to clear their heads and how it can foster creativity.

“Let it be known,” Gupta told me, “We work hard and we take our work seriously, but we take play pretty seriously as well.”

Dash & Dot are often praised for their ability to evolve alongside the child’s capabilities. There are hundreds of challenges, and more in the works, and the team is often releasing new attachments that allows kids to program different movements. As Gupta put it:

We knew from the beginning that if a child does not engage with our robots for an extended period of time, we will not succeed in delivering on the why of our mission. Learning to code isn’t just a matter of mastering syntax—we’re trying to give children a new mental model for understanding the world around them, a new mental tool for solving problems. We wanted children to discover the joy of achievement, repeatedly.”

He also knew that for Wonder Workshop to succeed as a business, parents must recommend the robots to other parents—and sustained engagement of their kids was going to be key. If these were, like most toys, something kids could take out of the box and master within a few hours, their business would fall flat.

We kept our why, this mission to allow young kids to have fun while learning to code, front and center. This compelled us to focus on ensuring the experience with our robots stayed fresh for a long period of time,” Gupta said.

In an age where tech more often enables passive entertainment rather than active engagement, the team at Wonder Workshop has created a product capable of challenging kids over a long period of time.

When Gupta first learned to code back in India, he most remembers those exciting times when, after asking himself why a string of code produced a certain output, he was able to figure out the solution for himself. Now, he’s trying to lead the computer programming revolution for kids by building the capacity for similar experiences into Dash & Dot.

Judging by the public’s reaction, he’s doing that quite well.


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