57. Cyrus Massoumi

The pitch is simple: Rather than try to book an appointment with your busy doctor by phone, do it online at ZocDoc. Patients seem to dig it; the site has more than 1 million users and $95 million in funding, and won’t even be nationwide until 2013. (It’s in 16 cities now.) But the sell to docs and investors wasn’t easy.

5 steps to: Winning over doctors

Step 1: Start with dentists

Step 2: Get kicked out, come back

Step 3: Sign up 10 doctors

Step 4: Follow the geography

Step 5: Arm with early data

3 steps to: Winning over VCs

Step 1: Identify the culture clash

Step 2: Buy jeans

Step 3: Meet and greet

Timeline

• 1998

  Receives bachelor’s degree from the Wharton School of Business at the University of Pennsylvania; meets Nick Ganju, who would later help found ZocDoc, while working at Trilogy Software in Austin

• 2003

  Receives MBA from Columbia Business School

• 2007

  Massoumi’s eardrum bursts on a flight from Seattle to New York; it takes four days to find an ENT specialist who can see him on short notice; ZocDoc launches nine months later

• 2009

  ZocDoc expands to Washington, D.C., its first market outside New York

• 2010

  ZocDoc is named the best place to work in New York City

• 2012

  More than one million people visit ZocDoc each month