By Cindy Atoji Keene

For Internet entrepreneur Drew Sharma, building online companies is like “an intense game of chess.” He owns hundreds of domain names, pared down from a thousand or more, and successfully founded two conglomerates that own and operate sites such as CarInsuranceQuotes.com, CDRate.com, HealthInsuranceQuotes.com, PrinterInk.com and PartySupplies.com. “I am a raging serial entrepreneur. I really enjoy e-commerce ventures – it’s like a sport for me,” said Sharma, 33, of Newton.

Sharma got hooked on building web-based businesses when he sold multiple businesses, including InkCartridges.com in 2009 to a large e-commerce company, beginning a winning streak of numerous other acquisitions. “This validated the model of building businesses by acquiring and developing strategic domain names, then gaining traction and reach with search engine optimization and other means,” said Sharma, whose latest venture is Cookies.com.

Sharma says the biggest challenge to developing an e-commerce site is “the waiting game.” “Even before you have revenue, you need to build and grow your website. You can go a year and a half just shoving coal into the fire without getting anything in return,” said Sharma, who said often the tipping point comes about 18 months, when the fruits of labor finally start paying off.

Q: What goes into acquiring domain, or website, names?
A: The most valuable domain names encompass an entire industry, such as PartySupplies.com or Cookies.com, because of the level of traffic they can achieve. For example, a huge amount of visitors type in “Cookies.com” into a browser without us even needing to advertise.

Q: Was it difficult to get Cookies.com as a domain name?
A: This type of domain name sells for astronomical prices, up to six to seven figures. Acquiring a domain name is a complicated process; you can contact the seller directly or go through a broker. We were pursuing Cookies.com for a long time but didn’t get to the negotiating table until the day after the Lehman Brothers collapse. Everyone felt panicked in the economic world, but we were able to get the name at a more reasonable price because of the economic demise. We picked up a few other gems at that time as well.
Q: How did you fund your first few businesses?
A: My partner and I funded our first company, Mindfire Interactive. We both put in $6,000, and it turned into a multimillion dollar business. We used the cash flow and proceeds as well as the sale of the business to acquire properties on the side and it all evolved from there.

Q: Are entrepreneurs like you made or born?
A: When I was five years old, I told my mom I wanted to be an entreprenuer when I grew up. I got my MBA and did the Wall Street route for a while but remained fascinated with all the entrepreneurs out there who fly under the radar and build great companies out of their basements and garages. Then a few friends and I started a dotcom venture. It took me out of mindset of living a 9-5 job and wanting to chart my own course, something that is very scary at first.

Q: Not every entrepreneurial idea works out quite as planned, right?
A: That dotcom venture ultimately failed but it was the best thing that happened to my career. When things don’t work out on your first try, you have to fall down on your face, then dust yourself off and try again harder.

Q: Who have been your role models for you?
A: Zappos founder Tony Hsieh is my inspiration. I’ve read his book, “Delivering Happiness,” cover-to-cover multiple times. E-commerce is so competitive. You have to create a loyal fan base of customers and instill passion in your customers and company.

Q: You have an undergraduate degree in philosophy. Does that help you at all?
A: Absolutely. It broadens my mind so I don’t focus so much on structure and I’m always questioning how things can be done differently.