What is the best advice you ever received?

One of our early investors, Vinod Khosla, believes it’s better to try and fail, than fail to try—advice we’ve put at the core of building our company. We’re constantly looking to optimize our current functionality—from every new feature and color to patient communication and customer service initiatives to company events and announcements—we test how well they resonate with our various audiences. We aren’t afraid to have failed experiments. These small failures inform us of what we can improve to provide a better experience.

What would you say to a group of young people looking to enter the tough job market?

There’s more opportunity out there than you might think. Be flexible and consider a variety of roles and industries that you normally wouldn’t. At ZocDoc, we hire based on candidates’ intrinsic abilities. Many of our employees are hired for roles that differ from the job they originally interviewed for, and it’s exciting to see how much success they can achieve by leveraging their natural abilities. Oftentimes we find that after just six months, the person with high potential outperforms those with high experience.  So don’t disregard a potential job opportunity just because your experience doesn’t perfectly match up with the description—you’ll be surprised what you might find.

What was the most important thing you learned in school?

In graduate school, some people say that grades don’t matter, but I learned that not only do they matter—everything about what you do at school matters. From the grades you receive to the relationships you build, they all determine how you’re perceived, which will come full circle later in life. Take the time to meet with as many people as you can, you never know how or when they might be able to help later on. For instance, some of ZocDoc’s early investors are friends I met at school.

What do you do for fun?

I love to go running to clear my head, stay in shape and explore the city. It’s important for me to disconnect, so I leave my phone at home and bring a small iPod Nano loaded with the songs at the top of the iTunes chart that week. I also look forward to brunch every weekend with my friends and family.

What has been your biggest failure?

The company I founded before ZocDoc, called One Size Too Small, seemed like it had everything going for it—a great team of dedicated people, high-profile board members, and some capital—but when the e-commerce industry collapsed, so did my company. I don’t blame the economy and instead look to learn from the mistakes I made along the way. Much of how I’ve approached building ZocDoc is due to those important lessons.

What business or technology person do you admire most? Why?

Although it may be cliché, I truly admire Steve Jobs for his powers of focus and simplicity—two things I’m constantly working on at ZocDoc—both for myself, and for the larger team. With this laser focus, he was able to build great products and a great company that embodied simplicity in everything from product design to the company’s structure. It’s been said that in order for companies to become truly large, they need to be simple, and I don’t think anyone has ever done this as well as Steve has.

What other companies do you admire? Why?

I’m a big admirer of Amazon because they’ve been extremely successful in a wide variety of different areas. Not only have they built the best in class e-commerce platform, but they built the leading e-reader and business infrastructure tools as well.  It’s very difficult to be good in one area, let alone be exceptional in many—and I’m not just saying this because Jeff Bezos is an investor. This type of successful versatility is something I aspire to for ZocDoc as we build out a more robust platform.

What technology sector excites you most?

I believe it’s important to be passionate about the work you do, so it’s no secret that I find the use of technology in healthcare very exciting. Traditionally there has always been a tradeoff for improving one of the three core areas: access, cost and quality.  Improving one area was always at the expense of another. But now, using technology, we’ve found that we can improve one area without damaging another, such as what ZocDoc has done for access. This is something I’m really proud of and am excited to see what other breakthroughs emerge.

What is one characteristic that every leader should possess?

I believe in the concept of “Humbition.” It’s a characteristic I aspire for myself and look for in my team. Leaders should be ambitious and constantly strive to improve. With that being said, they should also be humble and gracious, open to ideas other than their own, and willing to put the team before themselves. This is reflected in one of our core company values – Us Before Me.

What is your greatest achievement?

A couple of years ago, ZocDoc was named the #1 Best Place to Work in New York City by Crain’s New York Business. This was such a humbling and proud experience for me. Mayor Bloomberg even invited us to stand on stage during his State of the City address. Company culture has been something my co-founders and I placed great value on from the beginning, as I believe it’s impossible to build a great company without great people.  Creating an environment where employees feel valued is a responsibility I take incredibly seriously, and continually being recognized as a great place to work year after year in NYC, healthcare, and the entire country is something I take great pride in each and every day.