At some point in our life, we’ve probably all seen a video/story/picture or two that originated from CollegeHumor (acquired by IAC in 2006) or maybe you’ve worn a t-shirt from BustedTees. For this interview, I sat down with one of the two brain children (a friend) behind the sites and chatted about entrepreneurship and strategy in general.

Please join me in welcoming Ricky Van Veen…

1. Please state your name, title, and years at current company/position:
Ricky Van Veen, Co-Founder and Editor-in-Chief at CollegeHumor.com, which is eight years old.

2. What are you currently up to? If entrepreunering (my word), tell me about your startup.
Entrepenuering is a word that makes me think of flashlights and caves. Maybe because it reminds me of the word “spelunking?” Anyway, I’m still doing what I’ve been doing since I was a freshman in college – making young guys and immature older men laugh through the internet. Though now I’m less involved in the actual day-to-day content and more focused on growing the site long term. Also, I’m working with my business partner Josh on coming up with ideas for new web properties.

3. Why are you doing this? You could be doing so many other things in the world, what about this particular idea strikes you?
Well, technically I’m under contract to be doing this (when IAC bought our company in 2006, part of the deal was that the partners would stay and help grow the business for a few years.) But I’d be here regardless. Watching a business you started grow is always interesting, but the stuff we’ve started to do in the past year with original video in particular has been really exciting for me. We’re basically trying to take a brand that has built up a big following for one type of product (user-gen stuff and articles) and transition into the future with another (high quality short form original video). From an editorial perspective, it’s almost as if we’re starting a new company. That’s a bonus for me since new ventures are my favorite drug (besides heroin).

4. All startups should be addressing a problem in the market. What is that exact problem and how are you solving it?
I think there are two problems we’re addressing. The first is that there is a massive amount of new content being created on a daily basis online (especially in the humor space) and trying to find content that appeals to your particular mindset can be difficult. CollegeHumor offers this proposition: if you’re a young male who’s into offbeat comedy, visit our site on a regular basis and we’ll create stuff that you’ll like. And if somebody else creates something you’d enjoy on another site, we’ll make you aware of it.

The second problem concerns the quality of most content online - there simply isn’t that much being produced specifically for consumption over the web. There’s obviously lots of amateur stuff that’s fun to watch and some high quality 30min and 60min repurposed TV stuff, but little made for the web that’s shot/edited/acted well. So we’re trying to make content to bridge that gap.

5. Have you thought about your business model yet? I’m assuming so, so tell us a bit about it.
Our fundamental business model is not unlike any other media business. We present content to a specific demographic, and then sell advertising around that content. Where we do differ is in our ability to offer easy integration with our content since we have our sales, edit, and production teams under the same roof. As the online world shifts away from banner ads, this becomes more critical.

6a. If you’re looking at an ad-supported model, how are you going about it? Do you have in-house ad sales? Using a rep firm? What are the challenges that you’re facing with getting ad dollars?
We do have an in-house ad sales team based in New York, with outposts in Chicago and LA. I’d say that scale is probably our biggest challenge – trying to compete with those who might not have a better product, but more monthly visitors. We’re working to grow our numbers by upping our original content output (that’s really been a driver of traffic for us lately), increasing our marketing budget, and starting new sites.

6b. If you’re selling a product/service/subscription, how is that coming along? What are the challenges? Are you using the freemium model?
We’re not using a subscription model for CH. Though we do sell t-shirts through our apparel division, BustedTees. That’s coming along swimmingly. Originally we started selling t-shirts on the site because we weren’t big enough to sell ads. Now that we are, we still use BT ads for remnant inventory on CH, but that business has taken on a life of its own independently.

7. As an entrepreneur or investor, what are your thoughts on competition? How do you view competition?
Competition can definitely be a help. Indirectly, it forces you to innovate – stagnation equals death. Competition can help directly as well — every once in a while we’ll sit around as a group, and surf our competitor’s sites on a projector to see what they’re doing right, what they’re doing wrong, and see what we can learn from them.

At CollegeHumor, we view our competition in two different categories, those who compete for the attention of our audience, and those who compete for ad dollars. Surprisingly, there’s little overlap between the two groups.

8. If your competitor called you up to have coffee and discuss shop, what would you do? Would you go? What would you divulge?
I’d definitely go. We’re friends with most all of our competitors. In fact, I share a Hamptons house with a friend who runs what many would consider to be our biggest competitor. We learned early that the web content business isn’t a zero sum game. Just because somebody goes to site A doesn’t mean they won’t visit site B as well. I think most people would be surprised at how much information is divulged among Internet entrepreneurs, even competitors. That probably has to do with the fact that the Internet industry is so young and everybody feels like we’re all on the same team figuring it out together.

9. Is the current state of the economy playing to your favor? If so, why? If not, why?
No, it is hurting us. On-line advertising, despite its obvious advantages, is still slowly catching on with most traditional advertisers. Since on-line is still considered somewhat experimental, many of our larger clients have had their on-line ad budgets cut down to achieve cost savings in anticipation of this years recession.

10. How much of your time is spent working? How much is spent with family? Have you found the entrepreneurial quality of life yet?
Though I’m not sure if I fit in age-wise, I do think I fit into the “Always On” generation psychographically. That mindset – constantly checking e-mail on my phone, etc — has defined my work/life ratio since I started the business. I’m finally getting over that and starting to do things like not bring my laptop if I go away for the weekend, to the delight of my girlfriend.

It’s tough to shut off the work part of your brain, however. I find that to be true of many fellow entrepreneurs and I think the reason for that is simple: there’s no clear work/play distinction if you’re engaged and loving what you do in life. As long as you remember to take a break every once in a while, that’s a pretty great way to live.

I want to thank Ricky for taking the time to sit thru the Interview and if there are any questions, please feel free to leave them in the comments area and we’ll do our best to answer them. Thank you!