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Editorial: OpenAI Fails Its Ask Jeeves Moment

You Teach The Machines

Release Date: 10/21/2025

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You Teach The Machines

Domestic manufacturing, onshoring, re-industrialization? Poursteady founder Stephan Von Muehlen walks the walk despite the challenges.  A fascinating look at a 10 year old specialty electronic equipment company in the Gowanus neighborhood of Brooklyn, NY.  Hear how it ain't easy doing things domestically.  Also glimmers of hope that new technology can contribute to profitable growth across design, engineering, automated manufacturing, operations, and customer service.  

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You Teach The Machines

You can't make this up! Apple's podcast AI tagged our other podcast The Boaty Show as "comforting sleep stories." Thing is, the sleep stories are bits in a couple episodes where we talk like pirates! "Arrr time to take off ye peg leg and lay yer head down in the bilge wee ones." I got an automated bot email with the news we're charting at #15, sure enough it checked out.  Go listen to Conan O'Brien Needs A Friend, Netflix used AI to make marketing material that mistakenly included Conan as a former Star Search contestant. More evidence that AI WILL TAKE OUR JOBS but not do them very well....

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You Teach The Machines

Listen to Chapter 5 of my book You Teach the Machines! If you find this helpful, please download the full book wherever you get audiobooks.  Available from , , , and many more.  Also in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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You Teach The Machines

Listen to Chapter 4 Part 2 of my book You Teach the Machines! If you find this helpful, please download the full book wherever you get audiobooks.  Available from , , , and many more.  Also in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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You Teach The Machines

Take a break from the heaviest chapter of my book You Teach the Machines! If you find this helpful, please download the full book wherever you get audiobooks.  Available from , , , and many more.  Also in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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You Teach The Machines

Listen to Chapter 4 Part 1 of my book You Teach the Machines! If you find this helpful, please download the full book wherever you get audiobooks.  Available from , , , and many more.  Also in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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You Teach The Machines

Listen to Chapter 3 of my book You Teach the Machines! If you find this helpful, please download the full book wherever you get audiobooks.  Available from , , , and many more.  Also in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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You Teach The Machines

Listen to Chapter 2 of my book You Teach the Machines! Please share with friends and download the full book wherever you get audiobooks.  Available from , , , and many more.  Get it in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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You Teach The Machines

Listen to Chapter 1 of my book You Teach the Machines! Please share with friends and download the full book wherever you get audiobooks.  Available from , , , and many more.  Get it in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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You Teach The Machines

Listen to the Introduction to my book You Teach the Machines! If you find this helpful, please download the full book wherever you get audiobooks.  Available from , , , and many more.  Also in print at , , and my favorite: delivered to your local bookstore through  Help other readers by leaving a review on Amazon or Goodreads! Thanks so much --Jeff

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Oh Sam.

Ask Jeeves established precedent for the search industry that monetizing porn is bad for people and for business. OpenAI and its Microsoft godfather seems intent on doing the opposite. Will Google and Amazon read the room* and ask What Would Jeeves Do?

When I worked at Ask Jeeves in 2000 there was a debate. We were valued at $12B but nowhere near breaking even. Should Jeeves be a butler for porn? Eric our internet architect sat on the traffic control council for the internet (W3C) and reported that the bulk of the packets flying through this early system of tubes carried porn pixels. As one voice in my favorite group chat put it "...any user experience optimized to the n-th degree will be porn." Barely ten years in it was clear that porn drove the internet.

So the question was, would Ask Jeeves set the precedent that porn drove search? The license for the character from the PJ Wodehouse family was silent on porn, but in early conversations, the family made it known they didn’t want to see beloved Jeeves selling flesh.

But. Sooooo muuuucchhhh moneeyyyyyy. The answer? A pot smoke-filled back room. A remarkably sexually diverse (for 2000) crew of human supervisors of the core NLP engine "secretly" took over a conference room to teach an offline version of Jeeves about the dark side of human sexuality.

They called themselves the "Jeeviants."

In true Bay Area form, the Jeeviants immediately decorated Jeeves' Walled Garden with inflatable sex dolls, wall displays of dildos, and a giant inflatable vagina. All supervised by a cardboard cutout of Jeeves dressed to the nines in S&M leather. I was allowed in as part of a conversation on how to approach continuous learning from user data, though we didn't have those words back then. The goal was a completely separate search site where you and your firewall knew porn was on the menu.

Thankfully Porn Jeeves was shut down by leadership and the Wodehouses. Everyone recognized and accepted this was a bad short-term financial decision. The "usage-maxxing" and revenue projections were astronomical. But Jeeves had become a go-to safe space for school teachers and parents to teach children about the newfangled World Wide Web. A safe brand for decades-old businesses to dip brick-and-mortar toes into the eCommerce waters. So it was a bad business decision.

The twenty-something clown in me? Disappointed because there were ah-mazing illustrations of Jeeves done up in leather chaps holding a riding crop ready for go live. And that was HILARIOUS! The father or three in me? So, so grateful. Google took off a couple years later and followed Jeeves' example that porn was a third rail. A hot stove. The search industry took its sweet time figuring out how to put porn in a back room, like the video stores at the time did with VHS tapes.

Microsoft calls the shots at OpenAI now. Microsoft CEO Mr. Nadela's deft political moves hung Sam Altman from puppet strings, meaning it's Sam who announces Artificial Porn Intelligence (API?). Microsoft reportedly gets 75% of ChatGPT's profits until its $13 billion investment is recouped. After which their take drops to only 49%. Altman sells porn and godfather Nadela gets the envelopes full of money. But I'm not boycotting Word and Teams like I am ChatGPT. Smart.

I had the first AI Talk with my teenage son about his education last Spring. ("look, I know you're going to use it. I'm not trying to stop you. I just want you to make good decisions.")

Looks like I have to have another one. /s Thanks Mr. Nadela /s.

Can we get some feminist CEOs please?

Jeff Pennington is author of You Teach the Machines: AI On Your Terms, available online where you get books. Please consider connecting with other humans by ordering to your local book store through bookshop.org.