08/02/2010 11:18 am ET Updated May 25, 2011

DoubleClick Founder Kevin O'Connor On The 'iFad,' Google, And His New Venture

Kevin O'Connor, founder of DoubleClick, is launching a new venture after taking a ten-year hiatus from the Silicon Valley scene.

Today, O'Connor officially unveiled his new "comparison engine" (still in beta) which aims to organize the glut of data on the web to give consumers the "objective, factual information" they need to "make side-by-side comparisons" that will inform everything from where they travel to what they eat.

The entrepreneur, who enjoys playing practical jokes on his colleagues and is known for asking bewildering interview questions ("Are you smart?"), took some time to answer HuffPostTech's questions about his new venture, his advice for entrepreneurs, and what he thinks of everything from Google to the iPad.

HuffPostTech: In 2000 you resigned from DoubleClick, moved to California and took up surfing. Why?
Kevin O'Connor: My whole career has been driven by my obsession and passion for inventing new products. In 2000, I found myself CEO of a 2500 person company [DoubleClick] operating in 25 countries spending all my time dealing with lawyers, politicians and - sorry - the media. I lost the passion and knew I couldn't be a good CEO without it so I resigned.

I did remain as Chairman until the company was sold in 2005. After 17 years of 80 hour weeks I decided to lead a more balanced life which finally included the family and a new sport - surfing.

What have you been doing in the last 10 years?
I've poured my passion into my family, my wife and three kids. We've had a lot of fun together. My interest in next wave technology companies never fizzled so I started a VC company and invested and helped start-ups like Travida, Meet-Up, Procore and

Why are you returning now?
I became increasingly frustrated by the chaos of the web. It's a problem that needs a solution. Once I'm fixated on something I get incredibly focused and obsessed to build the best solution.

How is starting a company in 2010 different than it was 15 years ago?
Now the Internet is everywhere, it's essential and in all facets of life. In 1995 we were just laying the foundations, building roads, laying the plumbing, many didn't know what it was or how to use it.

It was hard to focus on your core competency as a start-up in 1995 because you also needed to build your own infrastructure. Most companies were doing it all themselves from creating the software to deliver their website to developing an ad serving system.

Today, start-up costs are lower and there are infinitely more resources. When starting DoubleClick we couldn't scale fast enough, at we can scale in a day.

As your Wikipedia page notes, you've run three companies, one sold to Google, another to IBM and the third reached revenues of 35million. What's the most important lesson you've learned as an entrepreneur? What advice would you have given yourself when you were starting out?
My advice is always the same - pick something you're passionate about because it will require a total life commitment to build a successful company.

Also, business is very simple but we tend to make it complicated. At the core of any successful business is you must provide the best solution to a big problem. This is obvious but often overlooked - people tend to focus on things like gross margin or setting goals for profit when in reality these things are the result of solving an important problem.

Looking back, what do you consider one of your biggest failures or mistakes? Why?
I've learned it's best to overreact to problems because small problems can become big ones quickly. For example, I will focus more on a customer loss then a win because any loss could be an indicator something is wrong.

What existing tech companies are you most excited about and why?
The entire SaaS [Software as a Service] industry is of great interest because of the massive economies of scale. DoubleClick was one of the first SaaS companies and it was a struggle, the internet was not proven - now companies love SaaS.

Cloud Computing is an extreme example of SaaS and is definitely the future.

What current trend / direction in tech concerns you most?
I think most people are concerned with information overload and trust. There are over 200 billion web pages and how much of this information is legitimate? People need information in a format they can understand and from reliable sources.

What does it take to be a successful entrepreneur?
Tenacity, disdain for authority, charisma and a lot of luck.

What were the most important leadership lessons for you?

Create a vision people can believe in, inspire them to achieve more then what they believed possible, and lead from the front and not from the corner office.

Tell me a little about "" Why do people need it?
You can find anything on the web but it can take you hours or days of research to compile it into a useful form to make a decision. People need objective, factual information in order to make side-by-side comparisons in order to make the best decision. We've created the first broad-based comparison engine to help people make informed decisions quickly.

I use FindTheBest to plan our family ski trips. I filter my options by lift ticket price, elevation, trail difficulty, and snow fall - there's nothing like it. Meanwhile, my oldest son is using FindTheBest to compare colleges, while my young daughter and her friends can't seem to get enough of the Horse, Dog and Cat Breed Apps.

FindTheBest is a comparison engine that allows users to find a topic, compare their options in a side-by-side chart, sort and narrow data with smart filters, and select the best choice based on what's important to them. This all happens inside of "Comparison Apps," or "Apps," which are presented in the form of filterable charts.

Presently, FindTheBest has about 350 Apps spread around nine broad categories:

• Arts and Entertainment
• Business and Economy
• Education
• Health
• Reference
• Science
• Society
• Sports and Recreation
• Technology

Free association! What's the first that comes to mind when you think of the

DoubleClick: Crazy ride.
Apple: Engineering done right.
Google: Wish I'd thought of it.
iPad: iFad or the next big thing.
Microsoft: Pity, I'd hate to have lawyers and government regulators determine what products should look like.
Facebook: I use it but can't understand why people spend more than 10 minutes a day on it.
Tweeting: I get enough spam.
Foursquare: I'm sure my friends are less interested in where I am than I am in having my friends know where I am.
Social Media: New name for stuff that's been around for a long time.
Bing: Too slow in crawling the web.
Webinar: Great but I still prefer Vegas.
Silicon Valley: Don't become Hollywood.

Is there anything else you'd like to share with us?

Yes, we want to hear from your readers. will continue to grow through "Expert Sourcing," we want professionals in their fields to add and change listings and suggest new Apps.