Satya Nadella’s OpenAI Concerns, Google’s Next AI Model, The AI Monet Prank

Join us for the Big Technology AI Summit on June, 18, 2026. Get your tickets here: summit.bigtechnology.com.... Ranjan Roy from Margins is back for our weekly discussion of the latest tech news. We cover: 1) Satya Nadella criticizing his OpenAI partnership 2) Did Microsoft play the OpenAI deal right? 3) AI native vs. bold on debate 4) Which big tech company will rank No. 1 in AI? 5) Bill Ackman buys Microsoft 6) OpenAI and Apple are on the outs 7) Claude for Small Business is here 8) What's coming up at Google IO 9) The Great 'AI Monet' Prank 10) Alright, alright, alright --- Enjoying Big Technology Podcast? Please rate us five stars ⭐⭐⭐⭐⭐ in your podcast app of choice. Want a discount for Big Technology on Substack + Discord? Here’s 25% off for the first year: https://www.bigtechnology.com/subscribe?coupon=0843016b Learn more about your ad choices. Visit megaphone.fm/adchoices Learn more about your ad choices. Visit megaphone.fm/adchoices

• 0:00Speaker 00

  Microsoft CEO Satya Nadella's emails and text messages reveal a serious concern with his OpenAI partnership. Google has a new AI model coming. Is it going to compete with Codex and Claude Code? And is this Monet AI? That's coming up on a Big Technology Podcast Friday edition, right after this. This episode is brought to you by Genesis. What does it actually take to put Agentic AI to work across an entire enterprise? I recently spoke with Genesis Chairman and CEO Tony Bates about why orchestration is emerging as a competitive advantage in customer experience, and what companies need to get right in the AI era. Then I sat down with Adam Mitchell, Head of Enterprise Business Solutions at Voya Financial, to go inside a large-scale Agentic CX transformation,

• 0:46Speaker 00

  including the business decisions, trade-offs, and lessons along the way. You can watch both conversations now on my YouTube channel today. It's never been more challenging to get frontier compute. How do you know where to look, who to trust, or how much to pay? Akash is an open cloud that provides easy access, flexibility, and peace of mind. That's how companies like Razer were able to cut their inference cost by 15 times. Visit akash.network/alex for a free consultation. That's akash.network/alex for a free consultation. Welcome to Big Technology Podcast Friday Edition, where we break down the news in our traditional cool-headed and nuanced format. We have a great show for you today.

• 1:28Speaker 00

  We're going to go deep into the documents coming out of the Musk versus Altman trial, in specific, looking at Satya Nadella voicing his concerns about the OpenAI partnership in a very revealing email. We're also going to talk about Google's forthcoming AI model that is the company is planning to reveal at Google I/O next week. And we will determine whether this Monet is AI or not, and how people react depending on the originator of the art, human or machine. Joining us as always on Fridays to do it is Ranjan Roy of margins. Ranjan, great to see you. Good to see you, Alex. I feel this might be a Satya week here at Big Technology. It sure is because you know, one of the, we'll see what happens with this case with Musk and Altman

• 2:13Speaker 00

  and whether the verdict is consequential or not, but certainly the documents coming out of the case are consequential and give us a great view into the strategy around these companies partnerships and where the value is found along the chain in the AI ecosystem. So, you know, last week, we talked a little bit about the interpersonal dynamics. Ron John and I read this text thread between Miravati and Sam Altman. This week, we'll just go right into the business side of things because Satya, in a way that you rarely see from a leader of a Silicon Valley company, basically spells out the exact dynamics of his partnership with OpenAI and why he was a little bit dissatisfied with it. Here's what he says in an email.

• 2:58Speaker 00

  Here's what Satya says, "Overall, I want us to own the silicon infra foundational model IP and know-how. Right now, we are a very thin layer on top of Nvidia and the IP is with OpenAI. And we have a P and L that will lose $4 billion next year. I have not seen anything like this in my 30 years in our industry. I can justify it all by saying that OpenAI has smart people and Nvidia has Locken, et cetera. But if we're going to spend this kind of money and not have control of Destiny, it makes no sense. Better to be an investor and not take all this execution risk." I have, I have like thought through this email over the course of the week since it's been revealed. I mean, it's fascinating that Nadella is very clear that his company does not have the IP.

• 3:43Speaker 00

  And so therefore what they are is this layer on top of Nvidia that is effectively serving the compute to people using IP he doesn't own, which is the other side of the, you know, the praise he's been getting, right, that the praise he had been getting by being the company that had locked down OpenAI and invested in them and had rights to their IP. So what did you think of the fact that Satya is framing this this way internally?

• 4:09Speaker 01

  Is he wrong? Do you think he's wrong? Because I actually think my favorite part of this is I feel there's some tech leaders, you get a kind of, we all know what they're thinking in general. And then there's those who are just so savvy that they keep it close to the chest. And this is one of the first times I think I'm getting a genuine look as to how Satya Nadella really thinks. And again, he was prescient on this. I mean, he recognized exactly where they were, where the shortcoming was that, and I love that better to be an investor and not even take all this execution risk. So he recognized this idea of like the more partnership element as opposed to just the

• 4:51Speaker 01

  pure investor element was a major risk to the direction Microsoft was going. And I think we're going to get more into where Microsoft is today in just a bit, but he saw it coming. Satya, Satya is king.

• 5:06Speaker 00

  Disagree. Strong disagree. In fact, I'm quite disappointed in the way that Satya has approached this. So let me, let me put it to you this way, right? If you think about where you get value in this value chain of AI, it is building the foundational models and selling the, selling the intelligence, right? It's building the compute and selling the compute that powers the intelligence and then building the applications. And though I've always been on the side of the model as more important, there's actually real value in the application. And I think that with the OpenAI deal, Microsoft had this inside track to have the best AI applications because they required, I would say, the best intelligence builder, which,

• 5:49Speaker 00

  you know, had been the case up until maybe a few months ago. They had the lock in there. They had a requirement from OpenAI to work with them. They also had the lock in in terms of people that wanted to work with OpenAI through an API. They would have to do that through Microsoft's cloud offering through Azure. And instead of exploiting that advantage and finding a way to take OpenAI's technology and make Microsoft's applications, the best M applicant, business applications in the world, you know, he, he, this seems to me like a small minded way, and excuse me, I understand, I'm not the CEO of a top five company in the world, so, you know, understand I'm in the peanut gallery, but that being said.

• 6:33Speaker 00

  I still think I'm entitled to some criticism, the position to be able to make some criticism here. And this seems so small minded. I mean, Satya is the guy who brought growth mindset to Microsoft. Is this growth mindset?

• 6:47Speaker 01

  Well, I do like that you just possibly came up with the greatest ridiculous branding for the entire Microsoft Office suite, which is the best damn business applications in the world. I don't think I've ever heard anyone anywhere ever actually refer to the Microsoft Office suite as that, but

• 7:07Speaker 00

  That was the potential, but they didn't achieve the potential, even with this leg up over everybody.

• 7:11Speaker 01

  I still, I think they should lean into it and they should take it. And that's the entire new branding campaign. But I think best damn business applications in the world. But I think, no, no, okay, that's fair. I do agree. They had a bit of kind of like competitive moat around how OpenAI gets deployed across the entire enterprise, basically anyone who would ever use Microsoft Azure. But like, what, what would they have done differently, though? Like, they, they already had those kind of advantages. So, so what do you think actually should have happened? That they kind of stepped on, like, they kind

• 7:53Speaker 01

  of like, were much more aggressive with OpenAI, that this is the way things will work. When that AWS partnership starts, they kind of go hard at them. They integrate, remember Bing? Bing had the first OpenAI direct access. They actually invested in that. Like, what would have been the move?

• 8:12Speaker 00

  Right. Well, I think, first of all, I think the personalities in this partnership have led it down the wrong path, right? And maybe you could blame OpenAI on this, and we'll certainly get to OpenAI's relationship problems with Apple in a moment. And it does seem like OpenAI ends up having relationship problems with everybody it works with. So I'm not saying it's entirely on Microsoft, but there were reports of Microsoft getting frustrated with OpenAI and, and, you know, and, you know, maybe OpenAI was holding back some IP. But like, ultimately, you have this inside track. Use OpenAI technology in its fullest capacity to change the way your products work and make them AI first. They

• 8:55Speaker 00

  didn't do that. And in fact, the Bing situation is almost the perfect example. You know Bing for a time when you and I were Bing Boys, for newer listeners, I don't know if you remember this, but you probably weren't present, but Rontan and I were, we were such fans of Bing when it was, when it integrated ChatGPT or the GPT models, we called ourselves Bing Boys, Bing Boys.

• 9:16Speaker 01

  For a hot second.

• 9:18Speaker 00

  That way.

• 9:18Speaker 01

  A hot second.

• 9:19Speaker 00

  Think about that.

• 9:20Speaker 01

  I don't even look at it in a shameful way. I'm proud to have been a Bing Boy.

• 9:24Speaker 00

  We were on the cutting edge and so was Microsoft until some weird stuff happened with Kevin Roos at the New York Times where he cracked Bing, it made itself bad, Sydney, tried to take him away from his wife, and then what happened to Bing? Microsoft put the, it lobotomized the thing, I think, right? And took the personality away. So I think you have to be a little bit more risk tolerant than they were because of course they have this, you know, big enterprise business roster of customers that they've sold security and stability and safety for forever, for forever, which has been a good process.

• 10:00Speaker 00

  And they're not risk tolerant and you have to be risk tolerant when a new paradigm shift changes. And it feels to me like a squandered opportunity. I just, I just can't get over the fact that Microsoft had this, you know, unbelievable advantage in the bag and, and what has it done with it?

• 10:22Speaker 01

  Okay.

• 10:23Speaker 00

  Okay. It's, it's got a 27% stake in OpenAI and otherwise it's completely squandered this advantage.

• 10:29Speaker 01

  No, no, you're right. You're right. I'm gonna have to agree with you because thinking back to that time, and this is at a time when Anthropic was barely a whisper in the wind and like, I mean, that was, what was this, 2024? Like you have Google just going, you know, code red, reorganizing the entire company. We've theorized that maybe Sundar's McKinsey chops helped him kind of, you know, like completely reoriented, reoriented the entire company towards AI. Make changes. They launch and actually build one of the cutting state of the, cutting edge, state of the art foundation models, start integrating it into all their products. Meanwhile.

• 11:12Speaker 01

  You're right. Microsoft had the technology and instead there's Copilot, Copilot Studio, GitHub Copilot. Now GitHub Copilot is not, or even Microsoft is cutting back Claude code licenses they're reporting and forcing people to use GitHub Copilot. Like, you're right. At an organizational level, they had this advantage and they didn't do anything dramatic with it.

• 11:39Speaker 00

  Yeah. And I mean, I think some credit to Satya because in the same breath, he seems to have acknowledged this. He says, I want to spend the money. The innuendo needs to have a proprietary edge and we need to have a foundational model team that is self-sufficient at all time and has the know-how of taking what OpenAI does and productizing it. As long as we have an internal org investment model, OpenAI deal terms that all compose to achieve these two goals, we can take all kinds of other risks around monetization, et cetera. I think today, standing where we are today, even though Azure has grown 40% a quarter, which is absurd. I guess until you start to think that Google's grown 62% a quarter,

• 12:20Speaker 00

  albeit on a smaller base. But Satya knew where they needed to go and they still haven't gone there.

• 12:30Speaker 01

  I mean, now that I'm reading this, again, you're right. Like, he saw the danger. He saw what they needed to do and they didn't. But again, this is classic, you know, like the disruption difficulty of trying to understand which direction you go when you have these cash flow very positive businesses, very profitable businesses, when I guess the stock, you know, has kind of reflected that that lack of growth is kind of like assumed by the market. But yeah, he saw where it was going. They had the advantage and they didn't do anything about it is what seems to be coming out of this.

• 13:10Speaker 00

  And if anyone should have known better on this, it would be Satya Nadella, who came up in Microsoft through the company's server and tools division, which was selling. He ran that division when it was mostly selling on-prem servers and was like, hey, guys, this might be our bread and butter, but we should probably do the cloud, right? Even though nobody in Microsoft wanted to do that. But he understood that maybe you do sacrifice a little bit of current gain and current revenue and profitability. To be ready for the future. And of course, that is certainly what underpinned his desire to get involved with OpenAI. But it is just at the last mile, sometimes it's really hard to, you know, sort of make that move.

• 13:53Speaker 01

  This is a reminder at that scale, what these leaders work with. You can, you are the CEO, you see the future, you have seen the future in the past, you're even making some bets that you can just sign and you get to make that bet like the investment in OpenAI. But even your own organization, it is very difficult and unwieldy to actually kind of change things or drive it in the right direction. It's just a good reminder of how big these organizations are.

• 14:26Speaker 00

  This brings me back to the end of the year, last year, when I was sitting with Sam Altman and speaking with him about Google. And Google's, you know, driving OpenAI into a code red and what his strategy was to win against Google. And he told me, he goes, basically, there's a difference between products that are AI native and products that you bolt AI onto. And I believe the AI native products will win. And therefore, Google bolting AI onto its existing products will lose. And that sentence could have easily been said and maybe even more accurately be said about Microsoft compared to OpenAI. And I wonder if that was in the back of his mind.

• 15:05Speaker 01

  Wait, did, he was referring to, this was in December, right?

• 15:10Speaker 00

  Correct.

• 15:11Speaker 01

  Yeah. So that is interesting. Do you think Google's is bolting on AI products or building AI native products? And I know Gemini and Workspace versus Gemini, but I still, versus Microsoft, certainly, Google has a more AI native feel the way even ask questions and maps even, again, we've talked about this at length, Gemini and Gmail still kind of sucks, but like, they still feel more AI native than Microsoft.

• 15:41Speaker 00

  Yes, right. Well, that's why that's kind of the way I was framing it, which is that that sentence could apply to Google, but it really applies to Microsoft.

• 15:49Speaker 01

  Yeah. Okay, okay. All right, Sam. All right, Sam. Give you that one.

• 15:55Speaker 00

  And of course, I think I was just speaking with an investor this week who mentioned something that OpenAI, something like OpenAI's valuation hasn't changed in eight months over the private markets, while Anthropic has gone up 3X. And that brings us really to like, where is Microsoft in the public market right now? Right? So Microsoft is down 9.96% on the year, year to date in the markets, while the S and P is up by like 7 or 8%, right? So Microsoft's deeply trailing the market. Maybe it's because of this, maybe it's because of its association with OpenAI, which hasn't done much on the private markets as Anthropic has grown. But let's go with the barometer of all great financial decisions, Bill Ackman.

• 16:39Speaker 00

  This is from the Wall Street Journal, and Ranjan, I want to get your perspective on this. Bill Ackman's Pershing Square bets on Microsoft AI ambitions with a new stake. Bill Ackman's taken a new stake in Microsoft to bet that the software giant's investments in AI aren't reflected in the company's slumping share prices. Ackman said that Pershing had started building the position in Microsoft in February after the company's shares declined following its earnings report. We will disclose a new position to Microsoft and that it is now a core holding. You know, I think this is an important data point to bring up, because every time we have had one of these discussions of a company, you know, completely out to lunch on an AI transition,

• 17:21Speaker 00

  we've actually, you know, seen many of them turn around very, very quickly. And I could say with Google, right? The narrative was Google was done. Google's obviously not done. With Apple, the narrative was like, Apple is a legacy company or toast. Obviously, some of their bets can arguably be seen as good ones. What do you think about Microsoft? And does Ackman have a point here?

• 17:46Speaker 01

  I think he has a point in terms of just being deeply entrenched. But I do think the risk Microsoft faces here is, again, like, there's been plenty of reporting around customers, especially like the AI offerings within Copilot not converting to or converting at a much smaller scale. Again, Azure's growth is definitely kind of protecting them in the transition period, but you have both sides that you are everywhere, everyone uses you, that's good. You can, you're, you should be much more able from a distribution standpoint to actually kind of take whatever's happening in the market and be able to kind of, you know, like transform that into your product and then actually get it out to users.

• 18:30Speaker 01

  But they haven't yet. And they've had, again, now that, I mean, they haven't, even when they had the advantage of that access to OpenAI and when others didn't. So the idea that it's going to be different going forward is, it's, it's a risky bet. But as you said, like, things change so quickly. And even again, these gigantic corporations actually moving quickly in something that we had not seen in a long, long time. I think, or like could never have imagined in the industrial age that like, the most, you know, the biggest conglomerates actually being the innovators. So they still, you can't write them off in

• 19:15Speaker 01

  any way. But the fact that it's Bill Ackman, and I do like the reporting had, uh, now, like Ackman offered at a highly compelling, or Ackman said in the more than 800 word post, and anyone who's ever seen an Ackman tweet knows exactly what they're talking about. Yeah. I'm glad he was succinct on this one, but I think, I think it's an interesting bet.

• 19:40Speaker 00

  Yeah, I'll say this in Microsoft's defense. I've heard multiple people say that the Copilot integrations within Outlook and other Microsoft products are actually getting pretty good and are quite useful. So I think when you have that install base and you do, and it's not like they're completely ignoring it, they're bringing it in. You know, you can be the sort of brand of choice for a lot of people just by an object in motion stays in motion.

• 20:06Speaker 01

  It's May 15th, December 31st. Give me your power rankings, Apple, Microsoft, Meta, and Google, and Amazon. Throw them all in there.

• 20:21Speaker 00

  All right.

• 20:21Speaker 01

  Right now, I feel there's, if from a pure, like, let's just talk about AI, I have to think Google is number one.

• 20:29Speaker 00

  Google's one for me. Yeah.

• 20:30Speaker 01

  Yeah. I would say number two's a tough one. You can either have like the Azure business and its AI division. You can have Alexa Plus, I guess, or Amazon's internal or Rufus, actually, Amazon's doing interesting stuff specific to their own business, not really in like a consumer sales standpoint. Meta is doing Meta stuff.

• 20:56Speaker 00

  That is my dark horse for number two. I'm just gonna say it. I think that, you know, they have the GPUs, they have the talent, they released a respectable model, and

• 21:07Speaker 01

  They have the distribution.

• 21:08Speaker 00

  They're the company, yep, they're the company, have distribution, and they're the company that seems like it has the most to lose here, if that makes sense. Like, these other companies, Apple will still sell iPhones.

• 21:21Speaker 01

  What do you mean by that?

• 21:22Speaker 00

  Well, I think Apple will still sell iPhones if, you know, AI doesn't pan out for them. Could be like, maybe they won't have the same growth on like the next line of hardware, but Apple's gonna be okay. Meta, I don't know. The leadership of the company is all in on this front. Mark Zuckerberg and Alexander Wang are sitting next to each other, trying to build us super personalized, super intelligence, and if they mess up, they're, they're an afterthought in the tech world. They gotta get it right.

• 21:51Speaker 01

  Okay. I kinda wanted to go out on a limb and give Apple a new, actually, do you think anyone takes over from Google? Out of the big five?

• 22:01Speaker 00

  If you're suggesting that Apple might be able to.

• 22:05Speaker 00

  I don't think I agree with that because they're building on top of Gemini.

• 22:07Speaker 01

  Absolutely not, but.

• 22:09Speaker 00

  Right now, no, I don't think so. I mean, if you think about it, okay. So Google has the advantage of having this proprietary tech within its company. It has the advantage of being able to being deeply partnered with Anthropic. I think Google Cloud is going to start selling OpenAI models within the next couple of months. Based off of, you know, just kind of a hunch, right? So they're going to be the infrastructure layer that enables all three big models. They're going to have their own system. They're going to make, by the way, I don't know if you've seen this, but the AI integrations within Google products are starting to get really good. So they are going to have this native set of products.

• 22:46Speaker 01

  I'm going to go ask the question in Gmail. When was the first email to my wife's email address?

• 22:51Speaker 00

  Look, that's our next AGI test. Don't get ahead of yourself. It's probably not going to happen anytime soon. But some of these other ones are really getting good. And I see it on the back end with like business tools within YouTube, where you can like kind of talk to YouTube now and it will take a look at your data and give you real excellent insights. And so I think, yeah, I think it's going to be tough to displace Google.

• 23:16Speaker 00

  All right. Well, look, you know, we will, we'll follow that story before we end this segment. Rajan, can we do one more dramatic reading of the text messages coming out in this court case?

• 23:29Speaker 01

  I think we have to in honor of Satya.

• 23:31Speaker 00

  Okay, great.

• 23:32Speaker 01

  Satya week here.

• 23:34Speaker 00

  All right, ladies and gentlemen, we will now do a dramatic reading of Kevin Scott, the CTO of Microsoft, positioning himself to join the OpenAI board. All right, so I will be Kevin Scott, CTO of Microsoft. Kevin says, I can quit for six months and do it. Ready to be downvoted by Satya on this one and not really serious. Very big wide smiling face emoji.

• 23:59Speaker 01

  Satya comes in disliked. That's the whole thing. Just to dislike. I was even gonna, I was actually practicing my Satya accent. He actually sounds a lot like my dad. He has like, you've been in the US for a long time. There's kind of like little trip ups, W's for Vs, Indian accent, but he doesn't even have to say anything. Just disliked.

• 24:24Speaker 00

  Thumbs down. And then Kevin Scott responds with a smiling face that's crying, laughing emoji. I mean, this is interesting. Let me just run this by you before we go to break, which is that like, I've been back and forth all week about whether Kevin Scott handled this the right way. Clearly, he wanted to join OpenAI's board. Maybe he wanted something even more. I don't know. And, you know, when you're playing internal politics, you always want to give your boss like an out, I think, if you make a big ask. And the out that he gives Satya is ready to be downfolded on this one and not, and not really serious. Like, if you're not really serious, why mention it? But like, I kind of think he, if he wanted to do this, which he clearly did, he should have just asked for it. What do you think, Rajan?

• 25:11Speaker 01

  I, do you think he wanted to do it? Or do you think, I don't know. Hold on. Let me step back a second. My favorite part of these trials, I still remember on the Twitter acquisition trial, and that was even a different kind of type of person where like, Jason Calacanis and others would kind of like grovel at Elon Musk, and then he would just send like a thumbs down, or a thumbs up, or a smiling face reaction. To me, you have the CTO and CEO of Microsoft, and my, they're just like us. They communicate like teenagers. Smiley face. They don't, he's not even responding, just a thumbs down reaction, crying laughing emoji. That's the whole

• 25:55Speaker 01

  conversation of these masters of the universe. And that's it.

• 26:00Speaker 00

  Yeah, I mean, I mean, what it's not like he's gonna send like a 15 page memo on such a suggestion.

• 26:07Speaker 01

  You know what? I want my

• 26:08Speaker 00

  You want the memo?

• 26:09Speaker 01

  Five trillion dollar tech CEOs, maybe write like old timey English letters to each other. Just communicate, not the crying laughing emoji. Save that for the rest of us. Be above us. Be above us.

• 26:25Speaker 00

  Just go back and answer my question, though. Do you think that he should have just come out and said, put me on the board? I don't like this wishy washy stuff.

• 26:33Speaker 01

  And he didn't get it. I don't think he wanted to do it. I think like

• 26:36Speaker 00

  Why even say it then?

• 26:38Speaker 01

  I mean, just to be like, I don't know, just that I want to do it, but I don't really want to do it. But I know I might be asked to do it. I don't know. I think, why do you think he's going this direction?

• 26:53Speaker 00

  I think he really wants to do it. It's kind of like when you ask out somebody who you think is pretty. You're like, hey, do you want to grab drinks on Saturday? Ha ha, not really serious. You know, winky face. I don't know. I don't know if you went through that phase, but I certainly did. And, you know, maybe this is me just coming back and saying, God damn it, just ask her.

• 27:16Speaker 01

  Just ask. Oh, man, that was painful to hear read out loud.

• 27:23Speaker 01

  Not serious, winky emoji.

• 27:27Speaker 01

  I still don't think he was fully trying to think like, go for it. I still think that they're just kind of hanging out. They're just, you know, shooting the shit, making decisions that will kind of shape the entire future of the entire technology industry, sending some emojis.

• 27:45Speaker 00

  Well, anyway, he didn't get the date. So that's, I think, the moral of the story. All right. One last bit here. I know I said we're gonna go to break, but we're not. We're gonna talk about this OpenAI and Apple Alliance, right? This is from Bloomberg. Apple OpenAI Alliance Phrase Setting Up A Possible Legal Fight. Apple's two-year-old partnership with OpenAI has become strained, according to people familiar with the matter, with the AI startup failing to see the expected benefits from the deal and now Preparing possible legal action. OpenAI lawyers are actively working with an outside legal firm on a range of options that could be formally executed in the near future. That could include sending the iPhone maker a notice allegedly breach of contract.

• 28:25Speaker 00

  And OpenAI believed that the company's partnership, which wove ChatGPT into Apple software, would coax more users in subscribing to the chatbot. It also expected deeper integration with more Apple apps and Prime placement within a Siri assistant. Instead, Apple uses OpenAI, Apple's use of OpenAI's technology across its operating system remains limited and features can be hard to find.

• 28:49Speaker 00

  I don't know, isn't it the ultimate sign of weakness to sort of sue your partners for not featuring you enough?

• 28:55Speaker 01

  Well, okay, okay. So I loved this story and I loved it because my first reaction to it is clearly like, yeah. How can you sue them? Like, okay, it didn't work out. Just move on. It was a partnership. And even there was like a moment, I remember we talked about it might be disadvantageous to OpenAI. If people start kind of cranking out searches and using tokens, but don't fully understand that they're using ChatGPT or OpenAI. Even if Siri says, let me ask ChatGPT. But then what I, I want this to be. For no other reason, and please at the folks at OpenAI or when you're talking to Greg Brockman and June 18th at the Big Technology Summit.

• 29:39Speaker 01

  Please tell me that this lawsuit was because the ChatGPT integration into Siri was one of the single worst product experiences I have ever seen. It was so clunky, bad that like if a Series A startup put out something like that, I would be ashamed of it. And it was just so, so bad. I don't know if you remember, like, it wouldn't even give you the full answer that ChatGPT would. It would give you this truncated answer. You had to take this extra step. There's so like you, again, you just opened the ChatGPT app and it was a lot better. So my hope is. OpenAI was actually insulted at what Apple did with their model and their product, and that's why they're suing.

• 30:25Speaker 00

  I mean, that would be, I mean, that's what the article it seems to imply. OpenAI, man, like, why do you keep getting into these fights? How many partners have they had where they end up like, you get these stories where they're drafting legal paperwork then?

• 30:39Speaker 01

  You know what? They are saying you devalued our product so horrifically with that ChatGPT integration into Siri. That's what they're saying. And no one, we want to set legal.

• 30:54Speaker 00

  Integration.

• 30:55Speaker 01

  We want to set legal precedent for the entire tech industry that no one can ever make such a terrible integration again anywhere, or you will face legal consequence. That's what they're saying.

• 31:08Speaker 00

  Oh, my God, that's hilarious. I mean, I just remember being at WWDC and the, like, all the rage was that.

• 31:13Speaker 01

  Apple made a big deal about it. Apple made a huge deal about it and it was garbage.

• 31:22Speaker 00

  I think Ranjan, Ranjan here is also setting his own precedent. And if you, if you keep messing up Siri, Apple, he will, he will savage you here on the show.

• 31:31Speaker 01

  That's, let's make that agreement, Apple. If you fix Siri, I will sing your praises, but we're not there yet. And this is, this is just going to kind of live in the annals of history as I, one of the single worst product integrations of all time, if not the worst.

• 31:49Speaker 00

  If not the worst, if not the worst. All right, before we go to break, I do want to thank our listeners. We've been getting a lot of really great feedback from you, not always agreeing with us. But I want to say, if you've been sending emails or LinkedIn posts, I've read every one of them. And, you know, it's been a crazy couple of weeks, not always able to respond, but I have read, I'm taking it to heart and definitely also appreciate the, first of all, we got some nice feedback on our dramatic reading last week of the text messages. We really enjoyed doing it. Thank you. We'll keep doing that. And then we get, we got some reviews on Apple Podcasts, which are like, I want to just point out and be thankful for, we had one from John Carley, glad I listened. The podcast isn't perfect, but I've been listening for about a year and I'm glad about it.

• 32:35Speaker 00

  I appreciate that. Like, you know, we're, we're not here like saying we're, we're perfect at this. And if you have like, if there are places we fall short, definitely want to hear about it. But to come in, give it five stars and share that perspective is very meaningful. So thank you, John. And also, we have Apple app lover who came in two stars and gave us the five star rating, though, and said two stars out of two. Whether that's, you know, this show could be better, but I appreciate what you're doing. I'm giving you five stars. Or whether maybe Ron John, you're a star, you're one of the stars, and maybe I'm the other, and we get the two stars.

• 33:11Speaker 01

  And you know, two out of two, maybe they're just changing, they're changing the entire rating system. They're changing the game. Two out of two.

• 33:18Speaker 00

  Apple, after you botched the chat GPT integration, I'm not playing by your dumb podcast rating standards. Two stars now. I'll give them both.

• 33:30Speaker 00

  Yeah, but I, you know, bottom line is, and it won't be a broken record about this, but these reviews do really help. They let folks know that the show is active, it's worth listening to. And of course, it lets, lets guests know that they should come on. So thank you for your five star reviews. Keep it up. On the other side of this break, we're going to talk about Claude for small business, what Google might announce at Google I/O next week. Oh, God, we have so much to talk about. Maybe the, and we're going to talk about this, this fake Monet painting, or was it fake in the end? We'll be back right after this. This episode is brought to you by App Point. Everyone's racing to roll out AI right now. Co-pilots, chatbots, agents doing real work. But here's the part nobody loves talking

• 34:11Speaker 00

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• 35:01Speaker 00

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• 35:47Speaker 00

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• 36:03Speaker 02

  This episode is brought to you by Michelob Ultra. Good times mean competitions between you and your friends, like seeing who can throw some pigskin the farthest or rush the field the fastest. Winner gets an Ultra. Because it's not just a superior-like beer, it's also giving fans superior access to their favorite sporting events. Superior is worth playing for. Visit michelobultra.com/superioraccess to enter. Enjoy responsibly. Copyright 2026 Anheuser-Busch InBev Michelob Ultra Beer, St. Louis, Missouri.

• 36:31Speaker 00

  And we're back here on Big Technology Podcast Friday Edition with Ron John Roy of Margins. Ron John, I want to talk to you briefly about Claude for Small Business, which is a new product that Anthropic released. It's from TechCrunch, Anthropic courts a new kind of customer, small business owners. Anthropic is looking to court small companies, smaller companies. To that end, the company announced Wednesday the launch of Claude for Small Business, a new suite of services that are designed for companies like your local hardware store or coffee shop. The new bundle of features includes bookkeeping functions, business insight, and generative tools for ad campaigns. The new suite also includes integration between Claude Cowork and a number of software products like QuickBooks, Canva, DocuSign, HubSpot, and PayPal.

• 37:17Speaker 00

  I am I irrationally excited about this like I mean, I'm obviously a small business owner, but I do think that the fact that Anthropic is starting to release these things just shows that the range that Claude is able to handle is growing. And if I could get like a Claude coworker to handle my bookkeeping for me, it would be thousands of dollars a year saved for a potentially $20 subscription. Reality check me or or agree with me?

• 37:48Speaker 01

  Um, I'm gonna disagree more because any of these kind of offerings, I never quite understand what is different about them. Meaning like, okay, packaging up some kind of like prompts and skills into something that actually makes it so you don't have to figure it out from scratch is good. Kind of positioning it around the integrations to a QuickBooks. I think if they were like really going for it, here like take a spreadsheet, connect your bank account via Plaid, and we just do your bookkeeping and forget QuickBooks. And that would be interesting to me. But still, this kind of play nice, here's your existing tools. I know like people don't want to switch over right away, but I would

• 38:32Speaker 01

  enjoy a little bit more aggressiveness on this if they're really going for it. But by the same token, again, like I ran a startup for a number of years. I wish I had the technology that exists today from like in this only 2013 to 2017. And like, my God, all this stuff I get was a huge pain in the ass. But more from like an announcement standpoint, I don't know, I it doesn't really, it's not that interesting to me.

• 39:01Speaker 00

  Bronchon, I mean, what you're saying is where this is going. The connection to Plaid. Here, this is from ChatGPT. This happened the next day or a couple of days later. A preview for pro users, a new personal finance experience in ChatGPT. Pro users in the US can securely connect financial accounts, see where their money is going and ask questions based on the information they choose to connect your full financial picture now in ChatGPT, and that is through a Plaid connection, exactly what you asked for.

• 39:27Speaker 01

  Well, no, Claude did this May 2025. I've completely moved all my finances to it. Yeah.

• 39:34Speaker 00

  Oh, I didn't know that.

• 39:35Speaker 01

  It's done. See, this is what I, this is what I mean that-

• 39:37Speaker 00

  Capability overhang.

• 39:38Speaker 01

  No, but, but I mean, actually, I'm curious what you think about. A lot of these big announcements are essentially kind of repackaging existing capabilities, which is fine. Like if it means it gets people to understand how to use it more or what they should be doing with the product. But that's where I think like, and then, I don't know, they becomes, it's not even the model or the product at that point. It's essentially the, the marketing and the packaging. But a lot of this has been around for a long time, or it doesn't significantly change a lot. Like there was a QuickBooks integration for Claude before as well. So, so it's more they may, they, they keep making these announcements

• 40:23Speaker 01

  and they're have their moment and they're kind of exciting. But yeah, I don't, you're not, are you, did you use any generative AI tools doing your taxes?

• 40:36Speaker 00

  Yeah, I did. I done my spreadsheet into Claude and it was pretty good.

• 40:39Speaker 01

  Of course. Yeah.

• 40:40Speaker 00

  I mean, I had my account, a real accountant work on it, but I checked the work next to everything by uploading it to-

• 40:47Speaker 01

  How annoying has that got to be for accountants, but also terrifying?

• 40:50Speaker 00

  It's like the Zocdoc thing. It's like someone coming in and being like, I got Ebola. And they're like, nope, you have the common cold. But now it's every, every profession is going to deal with it.

• 40:58Speaker 01

  Yeah, yeah. That's real time. It's happening.

• 41:02Speaker 00

  All right. We always should, we should, we should, oh, sorry. Before we move on, I want to let folks know Boris Cherny, the head of Claude Code is coming on the show next Wednesday. We conducted that interview this week in San Francisco. I, one of my favorite interviews of the year. So definitely stay tuned for that. I, I'm really excited to release that on the show. And yes, Ron John, we did speak about token maxing and AI inefficiencies and my problems with Opus 4.7 and rate limits. So it's, it's juicy. It's, there's some meaty stuff on there and we're going to release that Wednesday on the feed.

• 41:36Speaker 01

  All right. I'm going to be listening.

• 41:38Speaker 00

  Speaking of next week, Google I/O is coming up. This is from sources. Google is about to release a new Gemini model. Sources say that Google plans to announce a new Gemini model at its annual I/O conference on Tuesday. The release will land roughly in the class of OpenAI's recent GPT 5.5 and well short of Anthropic's mythos, which despite not widely being available, has reset how every lab is talking about what leading means. Interesting. I thought this might be a moment for Google to follow the Codex and Claude Code path, but it doesn't seem like that's what's going to happen.

• 42:19Speaker 00

  Are we almost, you know, preparing for another narrative shift around Google where they're going to say it's behind again? It seems like that's where the story could be shifting.

• 42:33Speaker 01

  Well, it's interesting you say that because it hadn't occurred to me, but innovation other than VO and video generation, it's like Google has not come up in any conversation. And, and I mean, maybe it's what eight to 12 months, which is, you know, not that long. And maybe they're just like, I mean, they're printing cash and, you know, like signing up customers and et cetera. But like, also there hasn't been anything dramatic in terms of innovation, especially on the entire Agentic side and the whole world moving towards this. And so it's, I'm very curious what they're going to be doing. I feel they're due, they're due, even though we just gave them leader status out of the

• 43:18Speaker 01

  big five tech companies. I still feel like they should be doing something kind of like notable very soon.

• 43:27Speaker 00

  I mean, it is a fascinating dynamic, right? They are the leader out of the big five tech companies on AI model building and application. But if you rank them with OpenAI and Anthropic. I don't know. You'd have to put them at the bottom, right?

• 43:43Speaker 01

  Well, I I had to do again for newer listeners. Alex and I have had a running thing about if you go to Gemini within your Gmail and how different Gemini is and behaves. And the simple question that I ask regularly that I've been asking for a few years. When was my first email to? And then I'll add my wife's email address and it was about 2011. And I know that this, I think it got worse because before it would actually be wrong and give me a date range that was just like from the last few years. Now I ask, when was my first email to her email address?

• 44:25Speaker 01

  And the answer is sure, exclamation point, you can find your emails in Gmail search.

• 44:34Speaker 00

  Sorry, I just want to bounce my head off the mic right now.

• 44:37Speaker 01

  Like guys, state of the art models owning the distribution. Bring AI to the masses. Sure, you can find your emails in Gmail search, period.

• 44:51Speaker 00

  Yeah, but I guess here's here's sort of my point. I mean, where they are is, okay, best of big tech, worst of the AI labs. Just gonna say that's probably where they sit right now.

• 45:01Speaker 01

  Yeah.

• 45:01Speaker 00

  Even though Gemini is a competitive model, right?

• 45:05Speaker 01

  Standalone Gemini is good. It's good.

• 45:07Speaker 00

  They'll make a pretty good living doing that. I mean, Google Cloud platform on the back of Gemini went up 62%. I don't know. I went to Google Cloud next. People are just silly right now in terms of how happy they are with.

• 45:21Speaker 01

  Actually.

• 45:22Speaker 00

  Yeah, go ahead.

• 45:23Speaker 01

  Yeah, I was gonna say, or sorry, go.

• 45:25Speaker 00

  I'm just saying there's there's stunningly happy implementing Google Cloud platform right now with Gemini in the back. So yeah, but you don't want to, you don't want to like, kinda, you don't want to just sort of make a business based off of that. You want to be the leader, don't you?

• 45:40Speaker 01

  Well, that's why I feel they, everyone does want to be the leader than the amount they're investing. One would hope they could be. I got to say though, like in Maps, the Ask Maps feature has started to become more part of my life. Again, there's this weird disjointed thing like if you ask a question in Gemini around location, it's actually kind of a clunky experience to actually deep link it out to Maps. But if you ask within Google Maps, a question, it actually works pretty well. So I would say that's like my first integrated Gemini experience into one of their products. It's actually been good. So if they can do that, they are, they're in a good place.

• 46:25Speaker 00

  Yeah, the YouTube back, the YouTube backend is insanely good. Like it's crazy. It's like,

• 46:29Speaker 01

  what do you mean?

• 46:30Speaker 00

  Uh, just there's a Gemini integration that they built into YouTube, which will tell you about video performance, channel performance, give you optimization suggestions.

• 46:38Speaker 01

  So it's like an analytics.

• 46:39Speaker 00

  Personalized, it will have your data, it will look across YouTube. It's absurd. It's so, so, so good.

• 46:46Speaker 01

  Well, but that's not consumer facing though. That's more, that's for the creators of the world. Yeah. I mean, Meta, actually Meta.

• 46:52Speaker 00

  We're both saying if they do a version of this in each product. Sorry, go ahead.

• 46:56Speaker 01

  Well, sorry. I like Meta, the tools within like actually understanding performance have definitely dramatically improved. If you're saying that on YouTube as well. But Gemini, I need to, I'm going to play around with Gemini within the YouTube app itself as a consumer. I'll get back to you on my experience.

• 47:18Speaker 00

  Okay. To be determined. We'll obviously have Google News to talk about next week. So we'll put a pin in that. All right. Couple more stories to talk about before we leave. This was my favorite one of the week. Ron, John, I love this. This is from Futurism. Devious prankster posts real Monet painting tells people it's AI generated and watches the chaos unfold. A poster wrought some moderate havoc this week when they shared a cropped image of a real Monet While claiming it was an AI fake, unleashing a flood of ill-informed reactions and muddled discourse. So the user says, I generated an image in the style of a Monet painting using AI. Please describe in the much, in as much detail possible, what makes this inferior to a real Monet painting? And everyone who's ever played on like the online forums know, knows that this is like bait.

• 48:03Speaker 00

  Because everyone loves to point out a mistake or to complain and no one loves to say this was right or praise. And so the internet were bananas on this guy. Someone wrote, um, it was the Monet painting, which he said was AI was actually real, was an incoherent muddle of inconsistently saturated greens. Another one said there was no coherent composition. Someone else called it busy, artificial, nature in turmoil, polluted. Uh, another one said the AI image, AI generated image was trying too hard to resemble Monet's later paintings. Uh, and someone just said, it looks like shit and it is shit. It was the real Monet. They were all tricked. Stunning. Um, what do, what do you think about this, Ronda? I just thought this was amazing.

• 48:47Speaker 01

  I, I love this because there is this, I mean, the, I get a lot of the anti-AI sentiment out there. But AI is not good. Like, I think we have to move past that. I mean, it's like, the actual outputs, given the right context, given the right, like, I mean, just input. It's just, you can create pretty amazing things with AI now. And it's actually artistically good. It's, so I think, but I don't know, like the, imagine if you posted this on Blue Sky. My God, if this would have looked tame, I think.

• 49:29Speaker 01

  But yeah, I do love this kind of, yeah, this kind of trolling, uh, is kind of amazing to watch. Cause it just does capture, uh, where things are right now. And again, there's so many problems in terms of like, how these models were trained. And we can get into it, but just. It doesn't have to be bad, just if it was generated with AI.

• 49:52Speaker 00

  Yeah, no, you're totally right. I mean, there's, there's, there's, of course, it ran into this moment of anti-AI sentiment, right?

• 50:01Speaker 00

  And the one thing I worry about is there's been this problem described as like reality hole, where AI-generated content is so ubiquitous among us that we really lose our ability to tell what's real and what is AI. And this might be, you know, finally, it's like a funny prank. I admit it, it's hilarious. He got these people good. And it's sort of like, I just, and sorry if we have art. I mean, I like art, don't get me wrong, but it's just, there's something delicious about pranking like art snobs, don't you think? I don't know. Maybe I'm going overboard.

• 50:32Speaker 01

  I wonder, I wonder what the Venn diagram of the art snob and the then big technology listener is.

• 50:37Speaker 00

  But, uh, hi, hi, I would say.

• 50:39Speaker 01

  Very high, very high.

• 50:40Speaker 00

  Many, many fine painting collectors.

• 50:42Speaker 01

  You have just offended them all.

• 50:44Speaker 00

  Yeah, no, I love, look, I love art, I love art. Trust me, we have many nice paintings here, all created by humans. But it's the effect, or the affect, I guess, that I don't love. But anyway, but I may, I do worry that we're in reality hole, that's all.

• 50:58Speaker 01

  No, no, I mean.

• 50:58Speaker 00

  My one concern.

• 50:59Speaker 01

  I, there was a clip going around of The Office and Michael Scott introducing Claude to like Pam and Dwight and everybody. And it was so well done. Like I was actually having this moment of like, did they all come back and try to recreate and do like a office reunion or something and also not age at the same time? Like it was kind of terrifying.

• 51:26Speaker 00

  I mean, I'll admit, I've really enjoyed watching some of these AI videos recently.

• 51:30Speaker 01

  No, if they're good, they're good.

• 51:31Speaker 00

  They're good.

• 51:32Speaker 01

  If they're good, they're good. And there's plenty of slop out there, but if it's good, it's very good.

• 51:39Speaker 00

  All right, Ron John, bring us home with Matthew McConaughey, speaking of what's real and what's fake, and what it means for us as we move forward.

• 51:48Speaker 01

  I wanted to end on this story because I do think as like AI-generated content becomes more mainstream and actually kind of like the people stop caring if it's AI or not, still actually like how are creators compensated, especially ones whose likeness is being used, is going to become an increasingly important conversation. So apparently in 2023, Matthew McConaughey and his team filed for eight trademarks. Those included a sound mark on audio of the actor saying, "All right, all right, all right. All right, all right, all right." And then the "Just keep livin', L-I-V-I-N."

• 52:31Speaker 01

  Okay, that's too southern for McConaughey, I think, but anyways, apparently Taylor Swift.

• 52:36Speaker 00

  This episode, we might have gotten Ron John doing a Texas and an Indian accent.

• 52:42Speaker 01

  That is America at its finest, at its finest. No, but I do think it's interesting because I, there was like, I used actually something called Creatify, almost like a year and a half, two years ago, where it was actually actors providing their likeness to a service. And then you could create influencer, like AI-generated influencer videos, but using a real actor. And they would create enough video, and even this is two years ago, was pretty good. So how do actors monetize themselves in video? And is there going to be some kind of way? I think it's going to be one of the really most interesting ways versus they're all just going to get left in the dark

• 53:24Speaker 01

  and like imagine major brands using an actor's likeness and not giving a shit about it. So I don't know. I think the idea that McConaughey is going to be at the forefront of the legal wranglings around AI-generated content trademarks has me excited because it means that there's a non-zero chance he will testify in Congress at some point, much like Lars Ulrich in Metallica and then did in the 90s. So that's what I'm hoping for, him and Taylor Swift next to each other.

• 53:57Speaker 00

  Yeah, but do they testify as themselves or do their AI avatars testify? Because you know, a celebrity, the demands could be high for a celebrity's time.

• 54:05Speaker 01

  Well, my favorite part of Matthew McConaughey is he actually sounds like his characters. Like, like that, no, like when he talks in any interview, he actually sounds like, and also brought me back to Dazed and Confused, which I've not watched in a while, but I'm, maybe I'll need to do a rewatch.

• 54:22Speaker 00

  Wasn't that guy gonna be the governor of Texas, decided not to go into politics?

• 54:27Speaker 01

  McConaughey?

• 54:28Speaker 00

  Yeah. Oh, he wanted to run.

• 54:30Speaker 01

  I mean, wasn't Schwarzenegger was the governor of Texas, like?

• 54:35Speaker 00

  No, California.

• 54:36Speaker 01

  Or California. My God, you're right. You're right.

• 54:38Speaker 00

  I remember, we've done it. I mean, we do put TV stars, movie stars in elected office. Look at the White House right now.

• 54:45Speaker 01

  Never, never.

• 54:46Speaker 00

  I remember flying into California when I was in college and like looking out at all the houses and being like, a majority of these people are really a plurality of these people voted for Arnold Schwarzenegger to be their governor. And now with the state of the California governor's race, I'm like, man, Schwarzenegger would be such a good choice.

• 55:06Speaker 01

  Jesse Ventura, any of them. Yep.

• 55:10Speaker 00

  Amazing. Should we end with, all right, all right, all right? Is that, is that the best way to leave people this week?

• 55:15Speaker 01

  All right, all right.

• 55:16Speaker 00

  All right, all right, all right.

• 55:17Speaker 01

  Me doing a Satya accent. I'm gonna work on my Satya accent all week. I'm gonna come in strong next week. Dramatic readings, entire emails, pure Satya. Get ready.

• 55:27Speaker 00

  Amazing. All right, we're ready. Black and loaded. And we will have, I'm sure, a massive week of AI news ahead. Next week, we might even get a verdict in the Satya and the Musk alt and the trial. So closing arguments are going on.

• 55:41Speaker 01

  I'll work on my Sundar as well as Google.

• 55:45Speaker 00

  I don't know who am I? I guess I'll do my Zuckerberg. Okay. All right, everybody. Thank you, Ken, for joining us. Well, we can't, can't, we gotta go, we gotta go. We'll see, we'll see you next time on Big Technology Podcast.

• 55:58Speaker 03

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• 56:28Speaker 04

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