Greg Boesel is the co-founder and CEO of Swaptree.

What is your personal history in business and entrepreneurship?

I have always worked for start-ups and small companies, so my entrepreneurial spirit has definitely evolved from those experiences. It's very rewarding to be able to identify a problem or opportunity that exists in a business or better yet, everyday life, and being able to start with a blank slate and come up with a potentially new or unique solution.

Swaptree is actually the second software company that Mark Hexamer and I have founded together. Our first company, which we started during our last year of graduate school at Boston College developed software that assists attorneys with legal research. It is a great niche business, but since EVERYONE has books, CDs, DVDs and video games and not everyone spends their time sweating over legal research, the universal appeal of Swaptree is one of the reasons we enjoy working on it so much.

How long did it take for Swaptree to evolve from an idea to a functional service?

When most people think of swapping, they think envision two people exchanging items. While Swaptree does set up trades between just two users, we have actually developed fairly complex algorithms that can set up multi-way trades between users. This allows the number of items that a user can receive in trade for an item to increase exponentially.

So when a user adds a copy of Freakonomics or their White Stripes' CD to their "trade list", we have refined our algorithms to the point were it only takes us a few milliseconds to calculate all of the multi-way trades available and then we can instantly show the user the thousands of items that they could receive in trade for that book or CD.

With this level of complexity going on behind the scenes, it took us two years from the genesis of the idea and initial prototype until we were ready to start having the system generate trades for "real" users.

Why did you choose ASP.NET over other frameworks and programming languages?

The initial impetus was that .NET was the framework and language that I personally felt most comfortable with, so it was easy for me to prototype different sections of the site as we were fleshing out the idea. Secondly, we did the initial development of the site in India and at that point, the vast majority of the web developers were working in ASP.NET, so it made it easier to round up a team of developers to get development started.

Finally, given the complexity of our back-end mentioned in the previous question, the close integration between the .NET framework and SQL Server, and some of the advanced scalability and reliability features of SQL Server 2005 have really helped us as we have ramped up the site.

What has Swaptree done to ensure smooth and reliable swaps?

We use the eBay "trust model" so every user in a transaction rates every other user and before you enter into a transaction you can review the other user's transaction history. In addition, because our system is setting up the trades, we have implemented a number of additional safeguards for our users. For example, we can automatically identify users that have not had successful trades and exclude those users from our trading algorithm so that they won't receive trades in the future. All of this offers an additional layer of protection.

Also the fact that we are dealing with relatively "small value" items (no one is trading plasma television sets!) and no money is exchanging hands between users so there is less incentive for fraud means the percentage of transactions where a user ends up unhappy has been miniscule compared to some of the other sites where users and buying and selling from other users.

In addition, we have an automated system which allows a user to print a mailing label right from our website that actually includes the proper amount of U.S. postage, because we know the weight of all the items. Not only is it very convenient for users, but those labels provide us with tracking during the shipping process, so everyone in the transaction knows that the item has been sent and can follow the item as it makes it way to its new owner.

Who are your major competitors and what advantages do you have over them?

For starters, Swaptree is unique in that we allow users to do "cross-media" swaps, in that a user can trade a book for a CD, a DVD for a video game, a CD for a DVD, etc. This obviously makes Swaptree an useful site for really anyone, because everyone has a bunch of at least one of those types of items, and lots of households, especially with kids have lots of each.

It works out very well, and let's take myself as an example: I have bookshelves full of books and before Swaptree, I only owned a handful of DVDs, but would probably rent a couple of DVDs a month. I just put a bunch of books on my "have list" and DVDs on my "want list" and in a couple of weeks time, I had a great selection of movies that I can watch anytime. And the best part is that when I am done watching those movies, I can trade them again for other movies that I want to see. This way, I was able to get rid of a pile of books (which I had been telling myself for months that I needed to do anyway!) and I now have a great selection of movies that I own, and I know that I'll never hassle with renting movies ever again. We hear that a lot from our users: "It's amazing that I have more new media than I've ever had, yet I haven't purchased a single item."

Secondly, we are the only true trading site in that every time you trade an item, you will receive an item at the same time. A number of the other swapping sites use a "currency" or point system. In our opinion, these types of systems don't pass the "Can my mom easily understand the system?" test, and they require a leap of faith when you send your item off, because there's no promise that in the future there will be an item that you are interested in receiving for the number of points in your account.

Lastly, Swaptree is completely free for our users, we do not charge a fee for trading on the site. This is important because not only does this save our customers money, but it allows us to create a sense of community, since we can encourage users to trade informally, without trying to figure out how Swaptree can collect a transaction fee.

The swapping space is just now starting to gather a lot of attention and at this point, Peerflix, LaLa and PaperbackSwap are probably the leaders in the swapping space for their particular media type.