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Editorial: OpenAI Fails Its Ask Jeeves Moment

You Teach The Machines

Release Date: 10/21/2025

Editorial:  OpenAI Fails Its Ask Jeeves Moment show art Editorial: OpenAI Fails Its Ask Jeeves Moment

You Teach The Machines

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....

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Editorial: OpenAI Fails Its Ask Jeeves Moment show art Editorial: OpenAI Fails Its Ask Jeeves Moment

You Teach The Machines

. *Not holding out hope for Meta. Zuckerberg's bunkers aren't going to pay for themselves. The rats nest of Instagram's AI is already "engaging" our brainstems with as much soft core porn as it can get away with. Meta's recent virtue-signaling of "Instagram for Teens" is 99.999% certain to be a setup for serving hard core porn.

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Paul Berger Gives MJ Hope show art Paul Berger Gives MJ Hope

You Teach The Machines

Paul Berger joins and shockingly convinces MJ that AI is not the enemy! His thoughtful and constructive approach to MJ's skepticism is based on a lifetime of experience and success in two wildly different fields.  An excellent episode!  If you find the episode helpful, please share with friends and family.  Thanks for listening! 

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Cincinnati Children's - Philip Hagedorn, MD show art Cincinnati Children's - Philip Hagedorn, MD

You Teach The Machines

Chief Health Informatics Officer Phil Hagedorn shares a "this is happening right now" bedside view of artificial intelligence and clinical education.  MJ asks Phil to advise aspiring medical and nursing students, as well as twenty-somethings new to the workforce.  MJ asks Jeff the same question. Both have (some) answers! Thanks for listening! 

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Book show art Book

You Teach The Machines

Hi,  Here's how you can get You Teach The Machines... The Library... visit one of the libraries listed below or ask your local library to consider ordering from the distributor (IngramSpark) so you and others can read it.  eBook ISBN is 979-8-9988-152-2-5, hardcover is 979-8-9988152-1-8, paperback is 979-8-9988152-0-1. You may also email me at and I'd be happy to donate a copy directly to your library.  Local Business... visit one of the bookstores listed below or   and pick up from your friendly bookseller. Bookshop.org shares profits with physical stores, like a...

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How To Get You Teach The Machines: AI On Your Terms show art How To Get You Teach The Machines: AI On Your Terms

You Teach The Machines

Hi, Jeff here! Here's how you can get You Teach The Machines... Best for humanity: ask your local library to order from the distributor (IngramSpark) so you and others can read it. Give them the ISBN*. Hardcover ISBN is 979-8-9988152-1-8, paperback ISBN is 979-8-9988152-0-1.  Best for your community: ask your local book store to order from the distributor. Give them the ISBN. Paperback ISBN is 979-8-9988152-0-1. You pay $16, bookstore makes $8.50, I get $2.40. Hardcover ISBN is 979-8-9988152-1-8. You pay $24, bookstore gets $12, I get $2.01.  Best for my bank account: Buy direct...

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Pablo Urdiales Antelo - Journalism at Swansea show art Pablo Urdiales Antelo - Journalism at Swansea

You Teach The Machines

If you thought AI killed journalism, you haven't met Pablo! Thrilled to speak with Pablo Urdiales Antelo, full-time journalist and Class of 2024 graduate of the excellent Swansea University! Class of '25, '26, '27: this is a great discussion of Pablo's experience starting out in a profession AI is supposedly automating. We find space between doom and optimism, but if you're looking for easy answers with AI... let us know when you find them! Thanks for listening, check out Pablo's articles at , and get in touch at 

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Jack - CS at CalPoly show art Jack - CS at CalPoly

You Teach The Machines

Our first graduate in the workforce! Jack takes his fresh computer science degree to Silicon Valley and along the way shares how he lives and works with AI as a student, job candidate, and new employee.  We discuss whether AI will put 20-somethings like Jack and MJ out of work, or just maybe 50-somethings like me will be on the outs! MJ asks a great question about learning to think vs learning to program and we get closer to some answers. Get in touch at youteachthemachines.com and thanks for listening!

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Serena - AI, Privacy and Public Health show art Serena - AI, Privacy and Public Health

You Teach The Machines

The kids care about privacy! Hallelujah! Serena joins to discuss privacy and use of health data in AI.  Also, use of your content in OneDrive, Gmail, Google Drive to train AI.  We try for a balanced view, but are mostly freaked out. Thanks for listening, please review, subscribe and get in touch at youteachthemachines.com. 

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Alexa - French, and Sarah - Econ at Colby show art Alexa - French, and Sarah - Econ at Colby

You Teach The Machines

Does AI fall flat with French idioms?  Why should you NOT prompt AI with important data?  Three different answers to the question "If AI went away, would you be able to do what you learned with it."  Three seniors adapt their learning to an AI world whether they like it or not.  

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More Episodes

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.