Paul English

Being bored and frustrated is what makes Paul English tick.

English, a serial entrepreneur, has co-founded five technology businesses, including Kayak.com, one of the world's top 10 online travel search firms.

His decision to co-found Kayak.com came out of an impromptu meeting with a founder of the popular online travel website Orbitz in 2003.

"Steve Hafner and I had lunch and an hour later it was official," English said of their decision to launch Kayak.com. Today the company is led by a dream team of travel expert executives who were founders of Expedia, Travelocity, and Orbitz. Last month alone, Kayak.com had 20 million user searches for travel, and the site continues to grow rapidly.

When the West Roxbury, Mass. native does anything, he does it in a big way. As a teenager, English developed a software application using IBM punch cards, and by the time he was a senior in high school he had taught himself to write code and had developed a simple video game which he then sold for $5,000.

Still, he says, "I'd rather tell you that I sell used cars than say I'm a programmer, as I'm embarrassed at how difficult most software is to use".

And while programming may not seem sexy, English finds technology a perfect medium to discover the world and its opportunities.

"Many people mistake my interest in computers as having something to do with the computer," English says. "My fascination with computers has nothing to do with a keyboard or screen, but it is instead an opportunity to connect with people around the world, and to imagine new products. A computer is like a pair of eyeglasses that help you see the world in a different way."

After earning his computer science degree and working through a variety of programming jobs, English formed Boston Light Software — a company he grew to 15 people before it was acquired by Intuit. He stayed with the company for nearly four years and credits Intuit for a few life lessons, both professional and personal.

He says he learned that as an entrepreneur, "unless you pick one thing to focus on at a time you will not be successful." Another lesson — or perhaps realization — was bitter sweet. Having been offered the position of chief technology officer of Intuit, which had 6,000 employees at the time, English turned it down. While he was flattered by the offer, he said, he realized it was beyond his ability because "at the end of the day, I'm a small-business creator."

"I love creating small companies, and I knew I couldn't participate in that large environment," he says. "I get bored easily and my best strengths are at the creation stage."

Another one of English's creations came as a result of frustration.

English, one of seven children, had just lost his mother. His father was at the early stages of Alzheimer's — a disease that inflicts havoc on even the simplest of tasks. One exacerbating problem for English's father was automated phone systems.

"He couldn't use the telephone anymore, and it angered me because it robbed him of some dignity," he says.

Frustrated, he formed gethuman.com, a free online database that provides tips on getting past corporate America's automated phone systems to reach an actual person.

"I look at these stupid phone systems as an example of engineering gone wrong," he says.

What took only a weekend to form has spiraled into a major consumer movement that publishes best practices for quality phone service, and then rates companies' adherence to those best practices.

So what can we expect in the next decade from the serial entrepreneur?

English expects to launch more technology companies but he has also made a commitment to working on technology for world health for the next 20 years.