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My AI History

Last Updated On: 2025-09-01 04:31:53 -0400

My Personal AI History - A Tale in N Tweets

  1. AI is what we don’t know how to do in computing. Period. It isn’t about neural nets, NLP, etc. AI is what we don’t know how to do.

  2. My first pass at AI was founding NTERGAID, a hypertext tools company back in 1987. In 1987 hypertext linking was AI as we found at out the ACM’s Conference on Hypertext, Chapel Hill, NC. I was there man.

  3. My first AI colleague was the brilliant Mark Bernstein who, to this day, runs the same AI firm, Eastgate Systems which makes Tinderbox, a Mac tool for note taking that is unparalleled.

  4. Mark just added into Tinderbox the Link Apprentice, a tool for computing hypertext links via textual analysis. https://www.markbernstein.org/Feb20/LinkApprenticeAgain.html Again I was there.

  5. My second pass at AI work was working in Prolog to write an intelligent front end to online systems as part of a graduate class for Lee Teft in 1989. Prototyped using Quintus Prolog on SunOS, I actually delivered it using Borland Turbo Prolog.

  6. I ran NTERGAID for a decade until selling in 1996 to Dataware Technologies in an acquisition done by Kurt Mueller.

  7. My third pass at AI work came in 1997 when I led development of the Dataware II Knowledge Management System which featured a component that determined, dynamically, who in your organization was an expert in an area of an ontology. Took Gartner’s Magic Quadrant.

  8. My fourth pass at AI work came in 2002 when I got my NTERGAID cofounder to build an Outlook Email Inbox assistant called Inbox Buddy. We did dynamic prioritization of your inbox and we color coded your inbox. I’m less productive today with Gmail than I was then.

  9. I was at the first MIT Conference on Spam back in 2002 and we predated a lot of that work. Ultimately developing outlook addins as a technology architecture failed; sigh.

  10. My fifth pass at AI work came in 2003 when I founded the search engine Roogle ne Feedster.com. Not only did we do real time indexing of the blogosphere (that era’s social media) but we did object recognition such as figuring out if a blog post was a recipe.

  11. That last one was my algorithm and, damnit, we were so fast paced we didn’t patent that one. We also developed techniques to deal with the barrage of Elf Porn, blog spam, online gambling spam, etc. My own board fired me, damn it!

  12. My sixth pass at AI work came in a failed startup attempt to do facial recognition on family photographs and we underestimated how hard that was. That effort cost me a good friend and I still miss him.

  13. My seventh pass at AI work was eduFire which was a platform for online learning that dynamically matched students with teachers. We built a great product and lost focus and failed. But it taught me Ruby and Rails which I still use and love beyond all measure.

  14. Post eduFire I went the high paid consultant route and did work in online dating, rubrics for educational testing, algorithmic oncology detection, indexing and analytics of the App store ecosystem including revenue estimation math (Hi Jake!) and more.

  15. I then took a consulting gig with Dave Sifry, my biggest competitor in the blog search world and that brought me into the world of fitness bands. And while fitness bands proved to be a failure, well, while there

  16. I conceived of and prototyped TheraChat, eighth AI gig, which was a way for patients of mental health professionals to journal using a smart phone and used WordNet (state of the art then) for analysis. We also used an Eliza like model to keep patients talking.

  17. I left TheraChat, despite it being my damn concept because a) The CEO took all the credit for the innovation internally (which I could cope with but pissed me off)

  18. and b) the move to handling patient data meant HIPAA work and I wasn’t willing to carry my own Errors and Omissions insurance. HIPAA fines are steep and I could lose my house since I wasn’t covered by the company’s insurance (as a consultant). NOPED OUT!

  19. More work as a consultant and then a full time gig for the wonderful people at SEAS Education (not AI but a plug for great damn people; Hi Taylor).

  20. I now work for a non profit doing measurement and analytics of hate speech in social media and this is my ninth AI application. That’s roughly one new AI application over a 30 year career. And yes I still write code every damn day.

  21. AI isn’t magic; it is what we don’t know how to do with computers.