speaker notes for Philip Greenspun; revised January 2019

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I want to work on Internet applications. The MIT faculty says that nothing interesting or new is happening with the Internet. I do the big Boston-to-Alaska-and-back drive that I always wanted to do.

Worried about being lonely, I emailed friends and family a weekly letter, hoping to get thoughtful responses back. I had cameras with me, but the trip was more about the experience and the writing; the photos were just snapshots for a slideshow upon my return.

Set up the Web site for friends who couldn't attend the slide show, scanning the negs and chromes with Kodak PhotoCD, converting the letters from MSFT Word into HTML. I decided that a Web book could be much more interesting than a printed book since you could gather alternative perspectives from readers in the form of posted comments. Wrote a little software to let people type in a comment and have it added to the pages. Took about three days.


Huge response from the general public, usually in the form of "how did you get that photo of the bear?"

Wrote tutorial articles, which generated more questions than they answered.


Question and answer forum, trying to save myself from having to answer the same question twice. Reader B would answer Reader A's questions; my role reduced to moderation.

Built classified ad system for Hearst Corporation, which owns newspapers around the U.S. Said "let's have everyone in the U.S. in one big database, placing ads that can be for a fixed price or subject to auction; after the sale, Reader A can rate Reader B's credibility in a reputation system." (i.e., every feature of eBay) They said "that's a terrible idea; we would never want to use that." I asked "Can I use it on my site?" The response: "sure".

Taking a lot of ridicule from friends, family, and colleagues about wasting time on my personal Web site. With no ads or other obvious revenue source, what was the point? I responded that I enjoyed teaching and that it didn't cost much to operate.


Packaged up the software behind and gave it away as a free open-source product to other publishers to help them get started, saving them several programmer-years of work. Culminated in the name "ArsDigita Community System" and a company, ArsDigita Corporation, to provide support and service for the free product.


Added a photo sharing service so that people could upload their best work and/or work that they wanted critiqued.


Spun off to a team of MIT-affiliated friends who hoped to turn into a successful dotcom business. The timing was unfortunate, with money borrowed from friends and family shortly before the dotcom crash. The team commercialized the site with ads and subscription fees for service tiers, but revenues were not sufficient to pay their salaries. Everyone wandered off except Rajeev Surati, who had the vision to keeps the site alive.


Sold ArsDigita Corporation to some business-minded folks and retired. (Like every other leftover computer nerd from the 1990s, went down to the local flight school and learned to fly airplanes and helicopters.)


Google's entry into the Internet advertising market with contextual ads boosts the value to advertisers and publishers, proving that Rajeev was either prescient or lucky (or both?).


I'm officially on the Board of a company that has been largely dormant for years with no Board meetings, no shareholders meetings, etc. I decide that I need to resign or take it over as CEO and clean it up. Bright side: a lot of readers. Dark side: a lot of debt. Core decisions: bring Jin S. Choi back to lead software development; get Rajeev Surati to redouble his efforts on business development and monetization; get advice from Neil Mayle, Doug Robinow, and Shimon Rura.


With traffic steady at 60+ million page views per month and 3 million unique visitors per month, even with a new Internet boom going it will take years to pay off the friends-and-family debt plus interest. Rajeev, Neil, Doug, Shimon, and I, decide that the most sensible path to retaining our sanity and paying off the original creditors in full is to sell to NameMedia, a local enterprise that owns a ton of domains and a handful of "organic" sites such as They have a better revenue split with Google and are able to double the ad revenue immediately. So had a lot more economic value to NameMedia than it could have had to us as small-scale publishers with no power to negotiate a better deal with Google.

fall 2016

NameMedia hasn't met its own investors' expectations. Internet advertising revenue for smaller web sites has been devastated by competition from Facebook. sold for a tiny fraction of its purchase price to Creative Live, a VC-funded company that seeks to promote tutorial videos.
Text and photos (if any) Copyright 2007-2019 Philip Greenspun.