Summary:

Kevin O’Connor is the co-founder of the granddaddy of all Internet advertising companies, DoubleClick. Chances are, if you’ve seen a banner ad over the last decade or so, it was served up behind the scenes by DoubleClick’s DART technology. Now the backbone of Google’s banner ad inventory, DoubleClick was one of the first internet advertising companies formed, one of the largest of the dot-com era, and as we discuss in this interview, DoubleClick is really the Godfather of the New York City Silicon Alley tech scene.

One of the more interesting things to me, is when Kevin talks about the early controversy that DoubleClick ran into in terms of user privacy and cookies and control of user information. In the late 90s, the firestorm that DoubleClick encountered just for doing basic ad tracking was a huge deal. Now, in the age of Facebook and the NSA listening to everyone, that whole brouhaha seems… I dunno… naive? Were we ever really so young as an Internet? Anyway, Kevin has a lot of good stuff to say about that.

Summary:

When you talk about Yahoo, most people know the names Jerry Yang and David Filo. But if you talk to people who were there at the time, there is another name that everyone mentions: Tim Brady. Tim was Yahoo’s employee number 3. He wrote the original Yahoo business plan. He became Yahoo’s project manager, and as much as anyone, he played a major role in building the company that Yahoo became in the 1990s. Tim was also a college buddy of Jerry Yang’s, so he offers us excellent background on Yahoo’s founding and the thinking that went in to the company’s development.

Summary:

Yahoo became the web’s first truly great company, and in this episode, we examine why. Turning to advertising as a business model, Yahoo was among the first to find a way for the Internet to generate real money. In addition, we look back at the “portal wars” as Yahoo, Excite, AltaVista, et al, competed to become all things to all internet people, and in the process, helped set off the dot com mania.

Summary

This is a wide ranging and fascinating interview with John Danner. John was the co-founder of another of the major internet advertising pioneers, NetGravity. John gives us some more great background on how the technology and culture of the advertising industry evolved, and because NetGravity was the company that built Yahoo's first advertising system, we get some great details about early Yahoo. But John also gives us some incredible insights about what it was like during the dot com era madness. If you're currently an entrepreneur or aspiring to be an entrepreneur, you're going to want to listen closely to the 2nd half of this interview because John speaks some serious truths about the realities of growing a venture backed business.