Kevin Ryan, one of the most highly respected leaders of the New York technology community, talks about the ecosystem that has grown up since the dot com early days, when he and business partner Dwight Merriman pioneered DoubleClick Inc., in this episode of The Deal's Behind the Money online video show.

We spoke with Ryan at last week's Startup 2009 competition, which was co-hosted by New York's Silicon Alley Insider and Boston's General Catalyst Partners.

Ryan may be best known for serving as CEO of online ad pioneer DoubleClick, which was sold to Hellman and Friedman LLC for $1.1 billion in 2005 and then sold for $3.1 billion to Google Inc. (NASDAQ:GOOG) in 2008.

Today, Ryan and Merriman run AlleyCorp LLC, a network of affiliated startups that includes Silicon Alley Insider, 10Gen and Gilt Groupe.

Click here to see our previous video interview with Kevin Ryan behind the scenes at AlleyCorp. And for more on the role he plays in Silicon Alley, read Gillian Reagan's profile of him in The New York Observer.Watch the new video with Ryan, below, or download it on iTunes.

And please check out The Deal's other Startup 2009 videos: Click here to see our conversation with grand prize winner Cheryl Milone, founder of Article One Partners, moments after her victory; with finalist Path101 Inc. co-founder Charlie O'Donnell on why he sometimes wishes he never heard of venture capital; with Tumblr Inc. founder David Karp on how new hires have made him "happier"; with Jason Calacanis on Wikipedia founder Jimmy Wales being a "poser," not an entrepreneur; with Blip.tv co-founder Dina Kaplan on the challenges New York's entrepreneurs face; with General Catalyst Partners' George Bell on why the VC firm co-sponsored the Startup 2009 contest; and with Venrock's David Pakman on how crucial it is for founders to read signals accurately.

Still to come later this week in The Deal's Startup 2009 video series: our interview with Original Signal Recordings' Daniel Klaus, and a special compilation video in which we ask, "What was your worst mistake?" -- Mary Kathleen Flynn

For comments or suggestions about Deal Video please contact mwoehr@thedeal.com.If you would like to embed this video on your website the embed code is:

<embed src="http://blip.tv/play/AYGIslgA" type="application/x-shockwave-flash" width="400" height="330" allowscriptaccess="always" allowfullscreen="true"></embed>