Editor’s note: Jason Caplain is a general partner and co-founder of Southern Capitol Ventures, a venture capital firm in Raleigh. The firm focuses on partnering with outstanding entrepreneurs in the Southeast and Mid-Atlantic. It has invested in companies like Art.com, ChannelAdvisor, Global Value Commerce, Motricity, AVIcode and ArtusLabs. Personally, Caplain is very interested in software, e-commerce and digital media. He also writes the Southeast VC blog.

RALEIGH, N.C. – A couple of months ago, I spoke with Kevin O’Connor, co-founder and former CEO of DoubleClick. Kevin is also the co-founder and current CEO at FindTheBest. He has a lot of really good entrepreneurial stories and advice to share so I thought it would be good to do a quick Q&A with him as a post. And he agreed.

Kevin has some ties to the Southeast since he was the initial investor in Atlanta-based ISS, which went public and eventually sold to IBM for $1.4 billion. Of course, his success with DoubleClick is a widely known story exiting to Google for $3.1 billion in 2007.

Most recently, it was announced that FindTheBest was one of the first recipients of investment from Kleiner Perkins’ new sFund. So here is the Q&A. I hope this helps. Thanks again to Kevin for spending the time.

Q: With the businesses you have started in your career, how did you generate the ideas behind them?

A: We always start with brainstorming big problems facing a market. Then, we brainstorm major technology trends. We narrow the problems and tech trends to the top few. We then brainstorm again by applying a top tech trend to solving a big problem and out pops a bunch of product or company ideas. The feeling is disjoints happen with new tech trends and is the best opportunity to launch a new company.

What are the top three elements that you’ve had in your businesses that have helped your companies be successful?

There are really only three things in business: big market, best product and smart/competitive people.

Talent is obviously very important to you when you build your companies. What are the best methods you have used to attract the very best people to your companies?

A: I’m upfront with them and say if they are smart, passionate and hard working they will have the best time of their life. If they are not, then this job will suck and they won’t last long. Great talent loves to hear that – they want to compete with the best.

What are some lessons learned in your career that other entrepreneurs should pay attention to?

Ideas are cheap so come up with a lot of them, innovate constantly and focus all your efforts executing your strategy.

What are the areas that are most ripe for innovation for 2011 and beyond?

TVIP [television over Internet Protocol], cloud, vertical search and social.

What are some of the biggest mistakes you made? How did you correct the situation?

I repress all bad memories like a good entrepreneur. My biggest mistakes probably center around hiring the wrong person or coming out with a product too early and not sticking it out.

When is the best time to take VC funding? What alternatives should an entrepreneur be thinking about?

The best time to take funding is when you don’t need it. Ideally, you’ll have a product and customers which validate your market before you approach a VC. Most startups still begin with $25k so build a prototype and test it on the cheap.

Talk about FindTheBest. Why did you start it? What are your goals with it over the next three to five years?

A couple of years ago, I kept running into the same problem where I needed to make a big decision – school choice for the kids, web hosting for business, ski resort for vacation, but either couldn’t find great comparison data or couldn’t get past all the “affiliate shill”/scam sites purporting to tell me what was “best.” It took me a while before it occured to me these seemingly disparate problems were actually the same – the ability to filter and compare products and services with objective data.

What Kayak.com does for travel, we want to do for the other 1,000 important decisions you need to make in life. This is a massive market with no viable solution. We created a “comparison engine CMS” that allows us to rapidly create and develop comparison Apps for hundreds of product categories from best cities, fast food nutrition, smartphones and tablet computers. We create the foundation for these comparison Apps and populate the initial dataset but our goal is to have businesses and experts continue to build the data over time. This is happening.

We think FindTheBest is a big idea addressing a great number of large niches. However, as we learn more about “socially curated data” we believe we’re on the cusp of something gigantic. The web is this massive labyrinth of mostly unstructured data. Shouldn’t “like” things be organized in a way that is most useful to users? Stay tuned…

Get the latest news alerts: Follow LTW at Twitter.