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If I Knew Then: Tech Entrepreneur's Challenging Upbringing Led to Passion for Solving Problems


A long-time member of Seattle's tech scene, serial entrepreneur Naveen Jain is the center of a rags-to-riches story that has him now reaching for the moon. Literally. Growing up around impoverished Uttar Pradesh, India Jain's difficult upbringing had him often feeling hunger pains and frequently having his home uprooted, spending no more than a year in one location. Despite his hardships, Jain managed to get a degree in engineering and his MBA. Upon graduation, he moved to the U.S. with $5 in his pocket and soon began his entrepreneurial journey.

After having a stint at Microsoft in the late '80s, Jain went on to found online-search company Infospace and public-record service inome (formerly Intelius). Currently, he is the founder of Moon Express, a commercial space exploration company dedicated to discovering the Moon's resources.

We caught up with Jain to discuss what he's learned on his journey and what advice he would impart to aspiring entrepreneurs.

Related: If I Knew Then: Co-Founder of Natural Beauty Products Company on Staying Positive and Being Patient

Q: Knowing what you know now, what would you have done differently when you were first starting up?

A: I learned a great deal with my first startup InfoSpace. In particular, I learned the hard way how one should build out a team.

 At InfoSpace, I was the sole founder and lacked a group of peers and advisors, as well as the experience to know how badly I needed them. My own personal identity became interwoven with the identity of the company. I prided myself on being involved with every facet of the day-to-day operations of the business, being involved in every important meeting and taking full responsibility for every mistake and victory.

I did things considerably different when founding inome. Our six co-founders were experts in a variety of different areas. So while today I may be not immersed in every decision, I am surrounded by a team of experts, each charged with the responsibilities to drive their own elements of the business. As a result, we were able to scale quickly and create a sustainable, profitable business that has stood the test of time.

Q: What do you think would have happened if you had had this knowledge then?

A: I would have taken an approach to team-building with InfoSpace that was very similar to what we’ve done at inome.

Related: Three Lessons a Serial Tech Entrepreneur Learned from Bill Gates

Q: How did you learn this lesson?

A: In the early days, InfoSpace was a small operation. I ran it intentionally lean to maintain costs and also didn’t want to over-expand. We had a small office in Bellevue, Washington with little support staff. As the principal of the company, when something broke, it was my responsibility to fix it.

On one occasion, during a particularly heavy rain storm, our office was at risk of flooding. I spent hours alone boxing up everything I could and then placing anything I couldn’t transport onto tables, chairs, old computer monitors -- anything to get them as high above ground as possible. In those painstaking hours, I realized this experience was a metaphor for the entire business and that its future was based strictly on what I brought to the table, as opposed to being able to leverage the skills and expertise of a team. The experience was an eye-opening moment in my career.

Q: How do you think young entrepreneurs might benefit from this insight?

A: Talented co-founders who offer complementary skills are critical. They have expertise in specific areas you don’t. I am consistently skeptical of executives who think they can do it all. Mature executives have made a clear assessment of what they are good at and where they need to rely on the skills of others.

Successful entrepreneurs find great talent, add them to their team and continue to give credit where credit is due.

Q: Besides inventing a time machine, how might they realize these sorts of helpful pearls of wisdom sooner?

A: I believe there are three fundamental ways we learn: by asking questions of others, by reading and by doing. Certainly, the first two are very important. However, at the end of the day, there is no substitute for actually taking the plunge as an entrepreneur and learning from your own mistakes. Successful entrepreneurs are constantly experimenting and tweaking their products and other aspects of their businesses. Failures are inevitable and should be celebrated for the subsequent opportunities they bring. The key is to learn from them quickly and make adjustments.

Related: Do You Have the Moxie to Be a Parallel Entrepreneur?

Q: What are you glad you didn’t know then that you know now?

A: I’m glad I didn’t know how many professionals are simply going through the motions, feigning interest in an idea or business, without a real passion for them. If you don’t care deeply -- very deeply -- about what you do, what’s the point?

Too many people compartmentalize their work and personal lives when the truth is, successful entrepreneurs know the two bleed over in countless ways, each and every day. And the best entrepreneurs wouldn’t have it any other way.

Q: Best advice for young entrepreneurs?

A: Have a passion for solving a problem rather than a specific idea or product. When entrepreneurs grow highly attached to ideas and they start to invest huge amounts of time and money, it often becomes impossible to let go. Over time, your products will change and business models will evolve. There really is no such thing as a magic product. And rarely is there “overnight success.” Success is brought about by hard work, focus and indeed, passion.

The most valuable lesson I’ve learned: don’t forget to enjoy the journey. The road to success is long and mired with landmines, well intentioned mistakes and sleepless nights. It is important to celebrate the milestones and successes along the way, however small they may be. Through this enjoyment you will create a more loyal and passionate team and a more well-rounded and passionate you.

-This interview was edited for clarity and brevity.

What do you know now that you wish you would have known then? Let us know in the comments below.

Nina Zipkin

Written By

Entrepreneur Staff

Nina Zipkin is a staff writer at She frequently covers leadership, media, tech, startups, culture and workplace trends.