Founder Charlie O'Donnell discusses nextNY, a community for young professionals who have a stake in the future of tech and new media in New York City. NextNY hosts events in and around NYC and offers its members a resource-rich, wiki-based web site.

• A community driven organization of up and coming tech and digital media professionals in NYC
• Made up of 1500 members, the majority of which have between 5 and 10 years of experience
• The nextNY website offers a great resource for the tech community

All the usual suspects spent the weekend at BarCampNYC3 in Brooklyn. In keeping with the non-format format, here are some random impressions from the event.

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!

March 12 is here… finally. I’m proud to announce that my first book, Coloring Outside the Lines: Confessions of a Digital Native is officially for sale. It can be purchased online at the book marketplace, Lulu.

I’ve spoken about the book for the past couple of weeks and even have run some promotional advertising for it, but the day has finally come where the talk stops and it’s universally available for all. The paperback version of the book is fairly priced at $14.95 and the digital download is $0.76. Please note that profits from the book will be invested through Prosper to entrepreneurs in other countries who are trying to feed their families. I will post about this experience seperately over the coming weeks.

I couldn’t have written this book without the strong support of YOU - the readers of this blog, my family, friends, and colleagues. I hope you enjoy the book as much as I enjoyed writing it.

If you don’t step out of line, you end up waiting.

West coast company Mashery is hosting a Business of API’s Conference next Monday at The Yale Club of New York. Speakers include Nathan Freitas, Scott Rafer, David Rose and Jeremy Zawodny.

If you enter “web2newyork” on registration you will get a $100 discount on the ticket price!

Innovation within the advertising industry is accelerating each day. Fortunately at The Media Kitchen, I get to see dozens of emerging companies each month and get a real sense of where the market is on an insiders point of view. Andy and I came across each other just before I had joined The Media Kitchen and I got to preview what he was building and it’s exciting. I believe they are offering some truly unique services in terms of serving up audiences… not pages. Read through this interview, I bet you will find it interesting.

Please welcome Andy Monfried…

1. State your name, title, and years at your current company:
Andy Monfried, Founder/CEO of Lotame Solutions Inc., and 18 months.

2. What are you currently up to? If entrepreunering (my word), tell me about your startup.
I am dedicated to providing publishers and advertisers with knowledge about how to most effectively leverage the fastest growing segment of media today—social media. That is why I started Lotame. We focus exclusively on providing publishers with advanced monetization techniques and offer advertisers the most effective tools for targeting.

3. Why are you doing this? You could be doing so many other things in the world, what about this particular idea strikes you?
After my previous employer, Advertising.com, was bought by AOL, I began consulting both major media buyers and planners, as well as advertising agencies about how to use the Internet as a successful vehicle to promote their brand. Over the course of a year, I found that it was a challenge to harness the true potential that user-generated content offered. Further, there were no mechanisms in place to accurately target branded campaigns or effectively monetize inventory on the publisher side. There was a specific need, in terms of data surrounding social media that I felt I could address.

4. All startups should be addressing a problem in the market. What is that exact problem and how are you solving it?
Currently, the problem facing the marketplace is that there is an overabundance of inventory within user-generated content that needs to be effectively monetized and more accurately targeted. We form a true partnership with our publishers by guaranteeing them revenue on a monthly basis. In addition, we help them overcome the hurdles of frequency issues and time-spent unique to each user.

From an advertiser standpoint, we build completely customizable audiences that allow brands to touch people not pages. We aim to be their sole point of contact for aggregating social media outside of MySpace and Facebook.

5. Have you thought about your business model yet? I’m assuming so, so tell us a bit about it.
Our business model is one of the most unique in the industry. First of all, we only deal with and focus on social media. Second, we guarantee our publishers revenue on a monthly basis, which definitely sets us apart. We also share all our learning’s and knowledge with our partners before, during, and after campaigns. We aren’t an ad-network, but rather pride ourselves on being the premier aggregator of intelligence across social media. No more “black box” technology like others in the industry employ. Our model allows our partners to build audiences from the ground up, by focusing on unique data points inherent to user-generated content. We make the process of buying social media as seamless and as easy as any other purchase within a media spend.

7. As an entrepreneur, what are your thoughts on competition? How do you view competition?
I welcome competition. It’s the driving force behind any successful endeavor, business or otherwise. When I see others in the space working hard, it validates everything our company stands for

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 would have coffee with anyone, anywhere, at anytime and talk about any topic.

9. Is the current state of the economic market playing to your favor? If so, why? If not, why?
Almost everywhere you look all signs seem to indicate that ’08 is going to be somewhat of a rough time economically. We are well aware that the economy is going to affect how everyone does business. We have set realistic goals for growth over the course of the upcoming year and are focusing on monetizing inventory for our publishers to provide them with new streams of revenue

10. How much of your time is spent working? How much is spent with family? Have you found the entrepreneurial quality of life yet?
As I mentioned, we are undergoing major expansion and growth so it’s hectic to say the least. I spend half my time at our headquarters in Maryland and the other half at our NY location. I definitely put in way more than your typical 9-5 let’s just say that.

When it comes to family, there’s nothing more important to me. Honestly, my wife and kids are the ones who provide me with unwavering support and give me the strength to do what I do. My wife also has an entrepreneurial spirit and runs her own children’s clothing line. Despite our work, we always make family time our highest priority.

On a personal level, I also consider each member of the Lotame team as family. The company is one of the greatest and most rewarding endeavors I have undertaken, and I am both proud and excited to watch it continue to grow and mature.

If you have any questions for Andy from this interview, please feel free to post them below in the comments area… and we’ll make sure they are answered

This is the sixth interview in this series and I’m excited to announce that Sam Lessin, Co-Founder of Drop.io is participating. I’ve known Sam for a bit as we’re both participating in the New York entrepreneurial scene and apparently, our circles are fairly close together. His company is picking up some buzz here and there in the marketplace and I’m looking forward to what the future holds for his company, Drop.io.

Please welcome Sam Lessin…

1. State your name, title , years at current company/position:
Sam Lessin, Co-Founder, Drop.io. (Since August 2007, when my partner Darshan Somashekar and I started drop.io)

2. What are you currently up to?
Drop.io is a solution for simple private exchange (and Input/Output if you will). Take any type of media (pictures, video, audio, documents) through almost any digital input (web, email, mms, phone, fax) put it in a ‘discrete‘ location online, share it privately with exactly who you want, and no one else. No network, no search, kind of like an improved multi-channel FTP.
The ‘web 2.0’ community has been churning out great stuff for a long time for public sharing, where personal media and information is widely diffused across networks through social-, search-, tagging- etc. the thrust of the whole movement has been to let technology push your content out across different networks…

Drop.io takes a very different tack. We allow users to create simple private exchange points called ‘drops.’ Drops can be created in as little as two clicks, and users can optionally set things like passwords and self-destruction parameters. The service has no email signup and no “accounts.” Each drop is private, and only as accessible as you choose to deliberately make it. There is no network and no search function, drops are just floating points for private exchange. You can create multiple drops, add any type of media, and share/subscribe/zip download the originals as you want.

The solution has an incredibly broad base of use, largely because there is incredibly broad demand for simple private sharing. There are thousands of people who use drop.io every day to privately share baby photos with family members, or party pictures with friends. At the same time, we have a ton of freelancers and SMBs using drop.io to collaborate on projects, and schools using drop.io as a simple platform for privately communicating with students.

3. Why are you doing this? You could be doing so many other things in the world, what about this particular idea strikes you?
There are a few reasons – some which are business and some which are personal. At the highest level, it is wonderfully gratifying and fun to build something from the ground up you care about.

Business wise, there is an enormous and extremely broad demand for private sharing online and it is not being met by anyone in the market. Social networks and search engines are great, but the concept of simple private sharing is being left out in the cold. We want to fix that, because it is fun and important to build something that people want.

Personally, I really believe in this service on both functional and theoretical levels. Functionally, when Darshan and I set out to build drop.io we both maintained FTP sites just to move stuff around. We were constantly personally inconvenienced by the lack of a viable private sharing option for both work and personal uses. So, first and foremost, we built a service that we really wanted and needed ourselves.
On a theoretical level, I believe that it is important for people to have an option for simple privacy online. Lots of people like to talk about whether ‘privacy is dead’, that is just plain wrong. What has gone on is that for lots of reasons the internet has made it far easier to be public than to be private. People online have traded privacy for ease and functionality. This is the inverse of the historical norm, where privacy was easier and cheaper the publicity. The trade away from privacy fundamentally doesn’t have to be made online anymore. We are highly enticed by the opportunity to help return the internet to the historical norm by making digital privacy easy.

4. All startups should be addressing a problem in the market. What is that exact problem and how are you solving it?
See above… the ‘problem’ is the #1 thing we care about.
5. Have you thought about your business model yet? I’m assuming so, so tell us a bit about it.
We have thought about the business model extensively. In my opinion, if you don’t have a tight business case you can’t really do anything of long-term significance because your service is unsustainable. So, we didn’t do anything until we were really confident in our model as much as our service.
We are a ‘freemium’ play, in that we give away a basic level of service and then make money when users want to upgrade for more storage capacity. Over time we are going to be rolling in other upgrade options around our various services (phone, fax, etc.) all of which have been proven already by different players in related markets.

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 don’t believe in the ad market for a service like ours anytime soon

6b. If you’re selling a product/service/subscription, how is that coming along? What are the challenges? Are you using the freemium model?
It is coming quite nicely. We are very happy with the rates at which users are upgrading. For us it was very important to quickly staring to sell some premium services off the bat, less for the immediate revenue, and more so we could start the process of test and learn around the fuller offering we are going to be opening up over the next several months.
The challenge is to be giving people what they want and allow them to buy it in the way they want to buy it. I think often people don’t do enough testing around how they are selling things/how people want to buy things.

7. As an entrepreneur or investor, what are your thoughts on competition? How do you view competition?
Competition is good. Competition is clarifying. It is great to push the envelope in a new direction, which we very much believe we are doing, but if people aren’t trying to compete with you or even straight up ‘rip off’ your service within a matter of several months you should start to get worried.
One of the very early questions you have to ask is why hasn’t someone already done this? We have some very compelling answers.

8. If your competitor called you up to have coffee and discuss shop, what would you do? Would you go? What would you divulge?
We play a relatively open hand of cards. I love speaking with ‘competitors’ or people generally in the space, it is a great way to find out how they are thinking about problems and helps you figure out where the market is going. I wouldn’t divulge anything technical that they couldn’t easily guess on their own, but beyond that we are quite open about what we are doing.
In most cases there are technical, legacy, or even HR reasons your competitors are not doing exactly what you are (that is, if what you are doing is good) – so, I generally believe you can be quite open about what you are up to and not risk all that much.

9. Is the current state of the economic market playing to your favor? If so, why? If not, why? What is your forecast of the market throughout 2008 and do you see affects? Macro and Micro economic theory would be interesting to hear about.
We are not too concerned with the US economy at large for a whole bunch of reasons. But, to single out one central idea, despite the fact that we have only been online since November, we are already highly internationally diversified in terms of our user base and our development is domestic… so, we love a weak dollar.

10. How much of your time is spent working? How much is spent with family? Have you found the entrepreneurial quality of life yet?
My girlfriend works way more than I do. On Valentine’s Day this year neither of us wanted to leave our blackberries at home, so she came up with a great solution – we swapped, I took hers and she took mine. That was a hugely trusting step on both our parts and took the relationship to a whole other level (kidding, sort of).
The cool part about drop.io is that I really love it and love working on it. I love working with the team, I love thinking about the problems. So, the line between work and play is highly blurred. In my mind, that makes the quality of life superb. Maybe a few less ski days and a bit more stress, but net-net I feel way ahead of where I was pre-venture.

Especially in NYC you are going to work a ton of hours no matter what you do – you should be working on something you care about and have equity participation.

If you have any questions or comments for Sam Lessin based on this interview, please leave them below and we’ll answer.

Online media company For Your Imagination today announced a partnership with IFC to produce, in New York City, a new lunchtime daily web video series called “Lunchbox.” The IFC.com web series will highlight the wide range of content available on IFC as an independent cultural experience and will be executive produced by For Your Imagination and Colin Moore.

The premiere episode of Lunchbox, available on Monday, March 10^th 2008 at noon EST, will be hosted by Matt Singer, reporting from SxSW 2008 in Austin, and will introduce the audience to Lunchbox by presenting an overview of what’s to come. Currently, the show is scheduled to run until the end of 2008.

“IFC has a proven track record of providing some of the most interesting independent content available both online and on cable,” said For Your Imagination’s CEO, Paul Kontonis. “These incredibly witty daily shows will further spark thought and interest in IFC’s content and take advatnge of the lunchtime rush for cool videos.”

Each short-form daily episode of “Lunchbox” will have a specific focus and host – Monday will be home to “On IFC” with host Jonathon Gabrus, Tuesday will feature IFC’s unique take on “Music” with host and blogger Jim Shearer. Co-hosts Sara Scully and Will Rabbe, who currently provide the political segments on IFC, will delve into “Politics” every Wednesday, while Thursday will focus on the world of “Film” with Alison Wilmore. Wrapping up each week will be the “Media Lab” once again hosted by Jonathon Gabrus which looks at the coolest video on the web including featured user generated short films from IFC.com.