How curiosity and grit shaped my career path as a founder

How curiosity and grit shaped my career path as a founder

This is part of our "Who Is WhoCo?" series, which explores the unconventional career paths of our own team members.

March 7, 2022
 Min Read

My brother and I were raised as children of immigrants in the middle of South Dakota. My parents grew up very poor in India – but they worked very hard, brought us to the United States, and then did everything they could to build better lives for us, their children. 

They were both physicians and from an early age, I remember them instilling a deep value in education in my brother and me. When you come from an environment where you’re very poor, education is your way out. Education is what opens doors and creates opportunities. 

So, although I don’t have any specific recollection of having typical childhood dreams of being a firefighter or an astronaut, I’ve always been ambitious from a young age. As I was taught, I worked hard in school with the idea that I would be able to figure it out as I go.

Teamwork and competition

For many (not all) young people, joining school sports teams is how you flex your mental muscles for the first time around concepts like competition and teamwork. That was not the path I took as the son of immigrant parents – they simply didn’t know that stuff. 

Instead, my initial exposure to the exciting world of competition and teamwork came through my experience on my high school’s debate team.

Mitch Gaffer was our debate coach, and he was incredible. Not only did he take me under his wing with guidance and support, I also naturally excelled in debate. 

This led me to question myself, “Do I want to be a lawyer?” That’s the literal translation of debate, right? One that is easily bolstered by fantasies of becoming the trial lawyer who spends every day as the ringmaster at the center of suspenseful courtroom dramas.

Of course, then you get older and realize being a lawyer mostly involves doing paperwork. 

Then I went through another phase … “Do I want to go into politics?”

As a brown kid living in the middle of very conservative South Dakota, I encountered a lot of challenges throughout my life and especially early on. 

Some kids are not so nice when you’re young; at the same time, however, there are very nice and good people out there, too. So, I learned in my formative childhood and teenage years how to navigate tricky social dynamics and connect with all different types of people. 

So, after two years as student body president, I wondered if the best way to have a big impact and do good for others at scale was to leverage my social connectivity and debate skills in the arena of politics. But much like with lawyering, the idealistic sheen of politics soon gave way to the disillusionment of rigid bureaucratic structures, corruption, and lack of fairness.

As I inched closer to leaving high school for college, I knew I wanted to make a difference in people’s lives and have a lasting impact. However, I still had more to learn before I unearthed what my path to those goals would be. 

“Are you also going to become a doctor?”

With both of my parents being physicians, I did contend with outsider assumptions that I would follow in their footsteps. But my mother and father did not play into that.

“You do what you want to do,” they’d say. “If you want to be a doctor, great! But we’re not going to pressure you. Get out of South Dakota and find whatever it is that you’re amazing at and do it. We’ll support you.”

I took their advice. After high school, I left South Dakota behind to attend college at Stanford.

Let me tell you, it was like a world opened up before me. When you’re growing up on a farm in South Dakota, you don’t have a lot of options. But when I arrived at Stanford, there was so much opportunity for learning and discovery. What also excited me was how technology-centric Stanford is. 

Technology was the future, and that’s where I had to be

I narrowed my focus down to engineering, which excited me and also created more questions like: “What kind of engineer do I want to be?”

To answer this question, I put my head down and charged through a lot of introductory classes. To be honest, I was intimidated. The kids who were now my peers had already been exposed to this stuff in their high school years, but I hadn’t. 

I felt a little bit out of my league.

Still, I stuck with it. It didn’t take me long to realize that I was good at science and math. However, there were people in those classes who were better than me. And when I advanced to more hardcore engineering classes, the same thing held true – I was holding my own and doing well, and there were others around me who were smarter. 

Instead of backing down, this excited me. I caught myself learning from those around me. I learned how to approach concepts and challenges from different angles. And when I was immersed in classes that were more hands-on, working with tools and building things with other people, that’s where I found my true enjoyment. We were working as a team.

I ended up as a mechanical engineering major because that’s where you focus on building products and understanding how things work.

I worked well in the team environment

What had been true in my youth translated to my time at Stanford; being embedded in a team suited me well: 

  • I had the ability to get the most out of everyone. 
  • I understood how to bring the right mix of really smart people together to achieve a common goal. 
  • As someone who considers himself friendly, I was also able to attract similar people who would also contribute to a hard-working, fun environment.

As a result, halfway through my mechanical engineering program at Stanford, I had the following realization:

"I don't want to be a mechanical engineer. I'm not nearly as good at this as a lot of these other people. And this isn't something that I think that I should be doing professionally. It's not going to be as good for the world or as interesting exciting to me."

When you’ve committed to a certain path for so long, it’s very hard to step off of it. This is particularly true in college. Because when you get to a point where you’ve completed so many courses toward a very demanding degree, pivoting is incredibly difficult, if not impossible. 

So, once I knew I was a mechanical engineering student who didn’t want to be a mechanical engineer, I decided to stay the course:

I told myself:

"Look, I’m getting this great foundation in these different sciences and technology, spaces I still want to work in. Not only that, this major is going to have credibility because it's a really difficult one to get through. I am going to stick with this, and I'll leverage that some way."

I started college in 1999, at the peak of the “.com” bubble 

And I remember countless job fairs where companies were telling us, “You don’t need to finish school, you’re already really smart. Come work with us now, and you’ll make a ton of money.” By the time I graduated in 2003, the landscape was wildly different. That fantastical tech bubble had burst, and the job market collapsed.

Seriously, if you wanted to be in tech and you were living in the Bay area, it was a very depressing time. 

Initially, I thought I was one of the lucky ones. 

Coming out of college, I ended up with two job offers. One was at a big energy company with a business track, and the other was a high-tech boutique consulting firm. I opted for the latter because I thought there were a lot more growth opportunities for me. 

By the time fall rolled around and I was looking for roommates and a place to live in Palo Alto, I received a phone call that the firm was going out of business.

With the rug pulled out from under me, I felt lost

I didn’t have a job. I didn’t have a place to live, and I didn’t know what I wanted to do. The only thing I did know for certain was that I didn’t want to go back to South Dakota. I moved to Los Angeles. I stayed with my best friend and his mom, crashing on their couch until I could figure out what to do. They are like a second family to me. 

But even with that short-term safety net, I was depressed. I had worked hard and studied. I was a Stanford graduate with a job lined up. It was a rude awakening, and I had no idea what to do because those exciting tech jobs simply no longer existed. 

Again, I tried to make the most of my circumstances. I was in L.A., it was an entertainment town. Eventually, I was able to land an interview with Universal Pictures in their business development unit. I was less a fish-out-of-water than I expected; I gelled with the people I met and found myself more excited than I had anticipated. I was offered a job and I worked there for about a year.

There was a lot I liked about what I was doing. But during my time there, I also learned a lot about what I didn’t want. I struggled with the politics and jockeying that came as part of the deal of working within a large corporation. Also, because of its size, things moved very slowly. 

I kept my eyes open for new opportunities …

And then I saw a job opportunity at MySpace

OK, let’s take a beat to get the big question out of the way: 

“Did you know MySpace Tom?”

Yes, I did. In fact, he introduced me to my wife at a party. Now, back to the real story.

Back then, MySpace wasn’t really a known thing. Still, I’m not sure how I got my foot in the door with my resume and cover letter. I wasn’t qualified for the marketing manager role I had applied for. In fact, the person I met with told me as much. 

“This is not the job for you. But I like you. Come with me.”

I was escorted to the CEO’s office and met with Chris, one of the co-founders. An hour later, he said, "Why don't you come run business development for us? We're trying to figure things out, we're growing."

You can bet I said yes.

As soon as I walked in the door, I was hooked on the energy. There I was, wearing slacks and a button-down shirt, and everyone else is in jeans and t-shirts, and they were a part of something. You could feel it in the air, and I had to be a part of it.

I loved my job at MySpace for two reasons

The first was that it was reasonably ambiguous and the second was that there was so much opportunity to have an impact – after having been in a rigidly structured corporate environment, it was a very welcome shift in culture.

More than that, we were figuring things out and building our platform in real-time. For example, we were starting to see music take off on the site. How are we going to think about like working with different studios? We need to think about publishing rights, how does all that work?

I worked my butt off. I was the first person in, last person out. (Well, except for Tom.) 

I did that because I recognized I was in a fortunate position, being on the ground floor of something special. I wasn’t going to throw the opportunity away and take it for granted. Eventually, I became MySpace’s COO.

After a few years at the company, however, I started to get the itch.

I started thinking about starting my own company

This wasn’t a brand new revelation for me. 

Even back in college, I knew I wanted to start a company of my own. And again, it comes back for me to that idea of having a real, tangible impact on the world. When I looked at my peers at Stanford, I saw the ones who had the most impact were the ones who had built an organization from the ground up themselves. 

That’s what made me say, "I want to do this. I want to challenge myself and see if I can do this, and build something on my own." 

Like Steve Jobs said, I wanted to make my own “ding” in the universe. 

I’m sure part of that has to do with how I grew up. Truthfully, being different, I always had a chip on my shoulder, an ineffable drive to prove myself and do something big. 

Yes, I had helped build MySpace to what it became at the time, but I wanted to create something from nothing.

The opportunity presented itself when MySpace was acquired, and I started feeling some of the internal chaffing around corporate structures that I felt at Universal. 

I started a company called Gravity. I developed it in response to the fact that more and more of our content was moving online, and soon we would need to find a way to filter the noise out to present what was most interesting and relevant to users.

I did so along with a couple of amazing co-founders whom I had worked closely with during my time at MySpace. Karl, who’s the co-founder of WhoCo, also joined at the beginning – we had been roommates early on at Stanford and were very dear friends. Today, we’re more like family. 

Together, we built an incredible platform. It certainly wasn’t easy and we struggled, of course – building something from nothing rarely, if ever, is. But we gained traction and eventually started working with incredible companies like Yahoo, AOL, and the Wall Street Journal. 

We moved into AOL’s orbit and later on were acquired by them. And that eventually led to the chapter I’m still writing right now, with the founding of WhoCo. 

I have a lot of empathy for founders and startups

When I started Gravity, I had the confidence to pull the right people together as a team to make the dream a reality. 

I was right, and also I learned a number of hard lessons. 

I had come off of my time at MySpace expecting that my clout would follow me; initially, my departure made some headlines, but beyond that and some funding we secured, what I was working on was no longer newsworthy. 

Founding a startup sounds sexy, but it’s really hard to do. Back then, even more so because you didn’t have the resources and lean startup enabling technologies at your fingertips like we do today. You had to figure it out on your own. 

That’s why I empathize with founders so deeply. It’s so frustrating to read how “easy” it was for startups to raise a bunch of money and be super successful. Even when you know those stories are the exception, not the rule, it’s demoralizing. 

But when you run through that fire and keep pushing when it burns, you’ll be amazed at how much you are able to level up. Yes, there will be moments of doubt and anxiety, but that’s baked into the process. The most important thing you can do is keep going. 

Failure is not fatal

It’s only recently that I’ve realized I hear the same thing a lot from people over the years: "I know you're going to figure it out because you don't give up. You just keep going."

To be a successful founder of a company that is built to last, you need to potentially recalibrate your relationship with failure. 

You cannot treat momentary failures as mortal wounds. Failure is never fatal. It’s a learning opportunity. When looked at constructively, a failure is simply a mechanism by which you see what you need to do next. When you are confronted with a failure, challenge yourself to see what’s next instead of what’s broken. 

That is where true growth comes from. 

Growth is not the absence of error, it’s the direct outcome of encountering setbacks and finding a way around them. 

You’re going to make mistakes. You’re going to feel moments of defeat and you’re going to have a lot of sleepless nights. You’re going to hire the wrong people, and then it’s going to sting horribly when you have to let them go. (To that last point, that’s why I founded WhoCo; we want to help others avoid that.)

Then, hopefully, one day, you end up where I am. 

Where, when someone asks you if you’d go back and tell your younger self something wise to help them better navigate the future, you say, “I might not tell myself anything. I love my family and I love what I’m doing, why would I risk changing that?”

To those of you still on your journey …

Go find a company that excites you and energizes you. 

Seek out the infectious positivity; you may find it in unexpected places. For some of you, that may mean doing what I did – joining a company in a different seat than you envisioned yourself. But if you’re in the right place, more opportunities will present themselves. 

Also, connect with mentors and cultivate relationships with those who inspire you. Ask them questions, learn from them. 

Finally, don’t give up. Your path may shift in unexpected ways, but if you stay curious and open, you’ll be surprised where your own road may lead you.

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