In short
Microsoft CEO Satya Nadella’s internal concerns about the OpenAI partnership; Google’s upcoming Gemini model announcement at Google I/O; Anthropic’s Claude for Small Business; whether “Monet AI” pranks blur reality; plus OpenAI’s strained Apple partnership and a dramatic reading of Microsoft executives’ text messages from the Musk vs. Altman trial documents.
Guests
Ranjan Roy (Margins). No other guests appear as interview subjects; the episode is mostly co-host discussion.
Guest background
Ranjan Roy is a technology/AI commentator associated with Margins, discussing AI strategy, business models, and market implications.
Key claims
Nadella says Microsoft lacks foundational model IP/know-how, is “thin layer” on NVIDIA/OpenAI IP, and projects a P&L loss of $4B next year; he argues Microsoft should act more like an investor than take execution risk. Ranjan argues Microsoft squandered its distribution moat (Azure/OpenAI access) and failed to make products AI-native (e.g., Bing “lobotomized” after early ChatGPT integration). Bill Ackman’s new Microsoft stake is framed as a bet AI investments aren’t reflected in the stock.
Notable examples
Bing’s early ChatGPT integration; Copilot/Copilot Studio and GitHub Copilot licensing changes; Apple’s limited ChatGPT/Siri integration leading to possible legal action; Claude for Small Business integrations with QuickBooks, Canva, DocuSign, HubSpot, PayPal; the “real Monet painting” prank that triggered anti-AI critiques.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOExamining Nadella's OpenAI Concerns
1:50 to 3:56
Explore Satya Nadella's concerns about the OpenAI partnership and its implications.
“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.”
The Business Dynamics of AI Partnerships
4:00 to 5:14
Discuss the intricacies of AI partnerships and the potential risks involved.
“I mean, it's fascinating that Nadella is very clear that his company does not have the IP.”
Critique of Microsoft's AI Strategy
5:34 to 7:40
Evaluate Microsoft's approach to leveraging OpenAI's technology for growth.
“In fact, I'm quite disappointed in the way that Sadia has approached this.”
Reflections on Bing and AI Integration
7:40 to 10:14
Reflect on Microsoft's Bing and the challenges faced with AI integration.
“And that's the entire new branding campaign.”
Nadella's Vision and Organizational Challenges
10:34 to 14:01
Analyze Satya Nadella's vision for Microsoft's future and the struggles in execution.
“I just can't get over the fact that Microsoft had this unbelievable advantage in the bag.”
Understanding CEO Challenges
14:01 to 15:35
Explore the difficulties CEOs face when trying to innovate within their organizations.
“you do sacrifice a little bit of current gain and current revenue and profitability to be ready for the future.”
AI Native vs. AI Bolted Products
15:36 to 18:28
Discuss the difference between AI native products and those that bolt on AI features.
“Do you think Google's is bolting on AI products or building AI native products?”
Financial Perspectives on Microsoft
18:29 to 20:35
Analyze Microsoft's current market position and implications of AI investments.
“Again, Azure's growth is definitely kind of protecting them in the transition period.”
Power Rankings in AI
20:36 to 22:59
Debate the current standings of major tech companies in the AI landscape.
“Give me your power rankings, Apple, Microsoft, Meta, and Google, and Amazon.”
Dramatic Reading of Internal Communications
23:00 to 28:01
Engage with a humorous reading of internal texts between Microsoft executives.
“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.”
Show all 17 chapters
OpenAI and Apple: Legal Tensions
28:01 to 31:23
Discussion on the strained partnership between OpenAI and Apple, highlighting the implications of potential legal action.
“Apple OpenAI Alliance phrase, setting up a possible legal fight.”
Listener Feedback and Engagement
31:24 to 34:14
Hosts share listener feedback and reviews, discussing the importance of audience engagement and responses to past episodes.
“I mean, I just remember being at WWDC and like all the rage was that Apple was in attendance and made a huge deal about it.”
Claude for Small Business and Google I.O.
37:31 to 42:00
Discussion on Anthropic's new product Claude for Small Business and upcoming announcements at Google I.O.
“Ranjan, I want to talk to you briefly about Claude for Small Business, which is a new product that Anthropic released.”
Google's New AI Model and Industry Dynamics
42:16 to 48:20
Discussing Google's upcoming Gemini model and the competitive landscape in AI.
“I'm really excited to release that on the show.”
The AI Monet Prank: A Commentary
48:20 to 51:16
Analyzing the implications of a prank where a real Monet was claimed to be AI-generated.
“All right, a couple more stories to talk about before we leave.”
The Future of AI and Celebrity Content
51:16 to 55:15
Exploring the impact of AI on celebrity likeness and content creation.
“And it's sort of like, I just, and sorry if we have art.”
Reflecting on Celebrity Impressions
56:00 to 56:48
The hosts joke about impersonating various tech leaders and movie stars.
“I'm like, man, Schwarzenegger would be such a good choice.”
Transcript
Automatic transcript. May contain errors.0:00Big Technology Podcast Hosts: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 CloudCode? 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 True Diagnostic. I've been trying to get more intentional about my health lately. Not just how I feel day to day, but what's actually going on under the hood. That's why I checked out True Diagnostic. They offer at-home tests that measure your biological age, not just how old you are, but how your body is aging on a cellular level.
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1:49Big Technology Podcast Hosts: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. 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 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.
2:24Big Technology Podcast Hosts: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 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.
3:03Big Technology Podcast Hosts:Ranjan and I read this text thread between Meera Maradi 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. 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 &L that will lose$4 billion next year.
3:40Big Technology Podcast Hosts: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 Lockheed, etc. 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 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. 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 praise he's been getting, right?
4:24Big Technology Podcast Hosts: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 Sadia is framing this this way internally? Is he wrong?
4:38Ranjan Roy: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 pure investor element was a major risk to the direction Microsoft was going.
5:24Ranjan Roy: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.
5:34Big Technology Podcast Hosts:Disagree. Strong disagree. In fact, I'm quite disappointed in the way that Sadia has approached this. So 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 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 is more important. There's actually real value in the applications. 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 had been the case up until maybe a few months ago.
6:20Big Technology Podcast Hosts: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 business applications in the world, you know, 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.
6:58Big Technology Podcast Hosts:But that being said, 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?
7:14Ranjan Roy: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 that was the potential. But they didn't achieve the potential, even with this leg up over everybody. 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 the best damn business applications in the world. But I think no, no. OK, that's fair.
7:51Ranjan Roy: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 would they have done differently, though? Like they already had those kind of advantages. So what do you think actually should have happened? that they kind of stepped on, like they kind 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.
8:38Ranjan Roy:Like what would have been the move? Right.
8:40Big Technology Podcast Hosts:Well, I think, first of all, I think the personalities in this partnership have let 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 maybe OpenAI was holding back some IP, but like ultimately you have this inside track. Use open AI technology in its fullest capacity to change the way your products work and make them AI first.
9:22Big Technology Podcast Hosts:They 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, or you probably weren't present, but Ronjan and I, we were such fans of Bing when it integrated ChatGPT or the GPT models. We called ourselves Bing boys. Bing boys. We actually referred to ourselves that way.
9:46Ranjan Roy:For a hot second. Think about that. I don't even look at it in a shameful way. I'm proud to have been a Bing boy.
9:52Big Technology Podcast Hosts:We were on the cutting edge and so was Microsoft. Until some weird stuff happened with Kevin Ruse 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 big enterprise business roster of customers that they've sold security and stability and safety for forever, which has been a good process. And they're not risk tolerant.
10:30Big Technology Podcast Hosts:And you have to be risk tolerant when a new paradigm shift changes. And it feels to me like a squandered opportunity. I just can't get over the fact that Microsoft had this unbelievable advantage in the bag. And what has it done with it? Nothing. It's got a 27 % stake in open AI, and otherwise it's completely squandered this advantage.
10:57Ranjan Roy:No, no, you're right. You're right. I'm going to 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 reorient the entire company towards AI, make changes. They launch and actually build one of the cutting end state-of-the-art foundation models, start integrating it into all their products.
11:39Ranjan Roy:Meanwhile, 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 cloud code licenses they're supporting and forcing people to use GitHub Copilot. But like, you're right, at an organizational level, they had this advantage and they didn't do anything dramatic with it.
12:07Big Technology Podcast Hosts:Yeah, I mean, I think some credit to Sadia because in the same breath, he seems to have acknowledged this. He says, I want to spend the money. The Infer 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, open AI deal terms that all compose to achieve these two goals, we can take all kinds of other risk around monetization, etc. I think today, standing where we are today, even though Azure has grown 40 % a quarter, which is absurd.
12:44Big Technology Podcast Hosts:I guess until you start to think that Google's grown 62 % a quarter, albeit on a smaller base. but Satya knew where they needed to go and they still haven't gone there
12:58Ranjan Roy: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 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.
13:38Big Technology Podcast Hosts: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 open AI, but it is just at the last mile, sometimes it's really hard to, you know, sort of make that move.
14:21Ranjan Roy: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.
14:54Big Technology Podcast Hosts: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 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 that 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.
15:34Ranjan Roy:Wait, did he was referring to this was in December, right?
15:38Big Technology Podcast Hosts:Correct.
15:39Ranjan Roy: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 in maps, even again, we've talked about this at length that Gemini and Gmail still kind of sucks, but they still feel more AI native than Microsoft.
16:09Big Technology Podcast Hosts:Yes, right. Well, 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.
16:17Ranjan Roy:Yeah, okay, okay. All right, Sam. All right, Sam. Give you that one.
16:23Big Technology Podcast Hosts: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 Anthropics 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 &P is up by like seven 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.
17:02Big Technology Podcast Hosts:But let's go with the barometer of all great financial decisions, Bill Ackman. 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 shares declined following its earnings report. We will disclose a new position at Microsoft and that it is now a core holding.
17:37Big Technology Podcast Hosts: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. 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 they are the narrative was like Apple is a legacy company or toast obviously some of their bets can arguably seen as be seen as good ones what do you think about Microsoft and does Ackman have a point here
18:12Ranjan Roy: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 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.
18:58Ranjan Roy: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 open ai 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 and 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 any way.
19:43Ranjan Roy:But the fact that it's Bill Ackman, and I do like the reporting had 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 it's an interesting bet.
Read the full transcript
20:07Big Technology Podcast Hosts:Yeah, I'll say this in Microsoft's defense. I've heard multiple people say that the co-pilot 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 can be the sort of brand of choice for a lot of people just by an object in motion stays in motion. It's May 15th, December 31st.
20:38Ranjan Roy:Give me your power rankings, Apple, Microsoft, Meta, and Google, and Amazon. Throw them all in there. All right. 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.
20:57Big Technology Podcast Hosts:Google's one for me. Yeah.
20:58Ranjan Roy:Yeah. Um, I would say number two is a tough one. You can either have like the Azure business and it's 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, right meta is doing meta stuff and doing my dark horse for number two i'm just gonna say it i i think that you know they have the gpus they have the talent they released a respectable model and
21:34Big Technology Podcast Hosts:they have the distribution company yep they're the company i 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 Because Apple will still sell iPhones.
21:49Ranjan Roy:What do you mean by that?
21:50Big Technology Podcast Hosts: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 is going to 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 an afterthought in the tech world. They got to get it right.
22:19Ranjan Roy:Okay. I kind of 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? If you're suggesting that Apple might be able to, I don't think I agree with that because they're building on top of Gemini. Absolutely not.
22:37Big Technology Podcast Hosts: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 open AI 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.
23:11Big Technology Podcast Hosts:So they are going to have this native set of products.
23:14Ranjan Roy:I'm going to go ask the question in Gmail. When was the first email to my wife's email address?
23:19Big Technology Podcast Hosts: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. All right. Well, look, you know, we will we'll follow that story before we end this segment, Ranjan. Can we do one more dramatic reading of the text messages coming out in this court case?
23:56Ranjan Roy:I think we have to in honor of Satya.
23:59Big Technology Podcast Hosts:OK, great. Satya week here. 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. Satya comes in disliked.
24:31Ranjan Roy:That's the whole thing. Just to dislike. 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 V's, Indian accent, but he doesn't even have to say anything. Just disliked.
24:51Big Technology Podcast Hosts: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 opening eyes board. Maybe he wanted something even more. I don't know. Um, 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, uh, and the out that he gives Satya is ready to be down voted on this one and not, and not really serious.
25:26Big Technology Podcast Hosts:Like if you're not really serious, why I mentioned it? Um, 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, Ranjan?
25:39Ranjan Roy: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 they're just like us. They communicate like teenagers. Smiley face. He's not even responding, just a thumbs down reaction, crying, laughing emoji.
26:22Ranjan Roy:That's the whole conversation of these masters of the universe and that's it. Yeah.
26:28Big Technology Podcast Hosts:I mean, it's not like he's going to send like a 15 page memo on such a
26:34Ranjan Roy:suggestion you know what i want my you want the memo 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 just go back and answer my question though do
26:55Big Technology Podcast Hosts:you think that he should have uh just come out and said put me on the board i don't like this wishy-washy stuff and he didn't get it.
27:02Ranjan Roy:I don't think he wanted to do it. I think like, why even say it then? I mean, just to be like, I don't know, just that, uh, 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?
27:21Big Technology Podcast Hosts:I think he really wants to do it. It's kind of like when you ask out somebody who you think is pretty and you're like, Hey, do you want to grab drinks on Saturday? haha 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
27:41Ranjan Roy:ask her just oh man that was painful to to hear read out loud not serious winky emoji i i still don't think he was fully trying to think like go for it i still think that uh 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 well
28:13Big Technology Podcast Hosts: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 going to go to break but we're not we're going to talk about this open ai 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.
28:47Big Technology Podcast Hosts:That could include sending the iPhone maker a notice allegedly breach of contract. 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. And I don't know, isn't it the ultimate sign of weakness to sort of sue your partners for not featuring you enough?
29:23Ranjan Roy:Well, OK, OK, 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, OK, 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 open ai if people start kind of cranking out searches and using tokens but don't fully understand that they're using chat gpt or open ai even if siri says let me ask chat gpt but then what i i want this to be for no other reason and please that the folks at open ai or when you're talking to Greg Brockman and June 18th at the big technology summit.
30:06Ranjan Roy:Please tell me that this lawsuit was because the chat GPT integration into Siri was one of the single worst product experiences I've 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, 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. 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.
30:51Ranjan Roy:And that's why they're suing.
30:53Big Technology Podcast Hosts:I mean, that would be, I mean, that's what the article 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? You know what?
31:07Ranjan Roy:They are saying you devalued our product so horrifically with that chat TPT integration into Siri. That's what they're saying. And no one. Legacy killing integration. 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.
31:35Big Technology Podcast Hosts:Oh, my God. That's hilarious. I mean, I just remember being at WWDC and like all the rage was that Apple was in attendance and made a huge deal about it.
31:46Ranjan Roy:And it was garbage.
31:49Big Technology Podcast Hosts:I think Ranjan here is also setting his own precedent. If you keep messing up Siri, Apple, he will savage you here on the show.
32:00Ranjan Roy:Let's make that agreement, Apple. If you fix Siri, I will sing your praises, but we're not there yet. And this is just going to kind of live in the annals of history as one of the single worst product integrations of all time, if not the worst.
32:17Big Technology Podcast Hosts: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.
32:49Big Technology Podcast Hosts:And then 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 Carly. Glad I listened. The podcast isn't perfect, but I've been listening for about a year and I'm glad about it. I appreciate that. Like, you know, we're not here like saying 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.
33:29Big Technology Podcast Hosts:Whether that's, you know, this show could be better, but I appreciate what you do. And 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. Oh, I like that. And, you know, two out of two, maybe they're just changing.
33:43Ranjan Roy:They're changing the entire rating system. They're changing the game. Two out of two.
33:47Big Technology Podcast Hosts:Apple, after you botched the chat GPT integration, I'm not playing by your dumb podcast rating standards. Two stars now. We'll give them both. Yeah, but, you know, bottom line is, and I 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 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 are 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.
34:21Big Technology Podcast Hosts:And we're going to talk about 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 True Diagnostic. I've been trying to get more intentional about my health lately, not just how I feel day to day, but what's actually going on under the hood. That's why I checked out True Diagnostic. They offer at-home tests that measure your biological age, not just how old you are, but how your body is aging on a cellular level. Their True Age test looks at things like your pace of aging, organ system health, and even risk factors tied to lifestyle, giving you real data to act on.
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37:22Big Technology Podcast Hosts:If you're ready to stop guessing and start seeing, visit scribe.how slash big tech. That's S-C-R-I-B-E dot how slash big tech. And we're back here on Big Technology Podcast Friday edition with Ranjan Roy of Margins. Ranjan, 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.
38:00Big Technology Podcast Hosts: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. Well, 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 co-work to handle my bookkeeping for me, it would be thousands of dollars a year saved for a potentially$20 subscription.
38:42um reality check me or or agree with me um i'm gonna disagree more because
38:51Ranjan Roy: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's like take a spreadsheet, connect your bank account, be a 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 enjoy a little bit more aggressiveness on this if they're really going for it.
39:35Ranjan Roy: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.
39:59Big Technology Podcast Hosts:Ranjan, I mean, what you're saying is where this is going. Um, the connection to Plaid. Hear this 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 U.S. 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.
40:26Ranjan Roy:Well, no, Claude did this May 2025. I've completely moved all my finances to it yeah oh i didn't know that it's done see this is what i this is what i mean that capability overhang 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 it becomes it's like it's not even the model or the product at that point it's essentially the the marketing and the packaging um but a lot of this has been around for a long time or it doesn't significantly change a lot like there's a quickbooks integration for claude before as well so so it's more they may they they keep making these announcements and they're have their moment they're kind of exciting but yeah i don't you're not are you did you use any generative or ai tools doing your taxes yeah i
41:35Big Technology Podcast Hosts:did i done my spreadsheet into claude and it was pretty good of course yeah i mean i had my account a real accountant work on it but i checked the work uh next to everything by uploading it how
41:45Ranjan Roy:How annoying has that got to be for accountants, but also terrifying. It's like the ZocDoc thing.
41:50Big Technology Podcast Hosts:It's like someone coming in and being like, I got Ebola. And they're like, nope, you have the common cold. But now every profession is going to deal with it.
41:57Ranjan Roy:Yeah. Yeah. That's real time.
41:59Big Technology Podcast Hosts:It's happening. All right. We should, sorry, before we move on, I want to let folks know Boris Churney, the head of Claude Code, is coming on the show next Wednesday. We conducted that interview this week in San Francisco. One of my favorite interviews of the year. So definitely stay tuned for that. I'm really excited to release that on the show. And yes, Ranjan, we did speak about token maxing and AI inefficiencies and my problems with Opus 4.7 and rate limits. So it's juicy. There's some meaty stuff on there, and we're going to release that Wednesday on the feed. All right. I'm going to be listening.
42:37Big Technology Podcast Hosts: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 IO conference on Tuesday. The release will land roughly in the class of OpenAI's recent GPT 5.5 and well short of Anthropics 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 cloud code path, but it doesn't seem like that's what's going to happen. Are we almost preparing for another narrative shift around Google where they're going to say it's behind again?
43:27It seems like that's where the story could be shifting.
43:32Ranjan Roy: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 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 etc 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 I'm very curious what they're going to be doing. I feel they're due. They're due.
44:13Ranjan Roy:Even though we just gave them leader status out of the big five tech companies, I still feel like they should be doing something kind of like notable very soon.
44:25Big Technology Podcast Hosts: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?
44:41Ranjan Roy:Well, 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 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, um, 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? And the answer is sure exclamation point you can find your emails in gmail search sorry i just want to bounce my head off the mic right now like guys state-of-the-art models owning the distribution bring ai to the masses sure you can find your emails in gmail search
45:48Big Technology Podcast Hosts:period 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 yeah even though gemini is a competitive model right um standalone gemini is good it's good they'll make a pretty good living uh doing that i mean google cloud platform on the back of uh 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 actually yeah go ahead yeah i was gonna say or sorry go i'm just saying They're stunningly happy implementing Google Cloud Platform right now with Gemini in the back.
46:30Big Technology Podcast Hosts:So, yeah. But you don't want to just sort of make a business based off of that. You want to be the leader, don't you?
46:39Ranjan Roy:Well, that's why I feel everyone does want to be the leader. The amount they're investing, one would hope they could be. um i gotta 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 that's actually been good. So if they can do that, they are, they're in a good place.
47:23Big Technology Podcast Hosts:Yeah. The YouTube backend, the YouTube backend is insanely good. Like it's crazy. It's like, what do you mean? Just, there's a Gemini integration that they built into YouTube, which will tell you about video performance, channel performance, give you optimization suggestions. Oh, so it's like an analytics. Personalized. It will have your data. It will look across YouTube.
47:41Ranjan Roy:um it's absurd it's so so so good well but that's not consumer facing though that's more no that's for the creators of the world yeah i mean meta actually meta we're both saying if they do a version of this in each product sorry go ahead well so 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.
48:16Big Technology Podcast Hosts: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, a couple more stories to talk about before we leave. This was my favorite one of the week. Ronjan, 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 painting 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.
48:50Big Technology Podcast Hosts:Please describe 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 knows that this is like bait 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 went bananas on this guy. Someone wrote that 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 and turmoil polluted. Another one said the AI-generated image was trying too hard to resemble Monet's later paintings.
49:33Big Technology Podcast Hosts:And someone just said, it looks like shit and it is shit. It was the real Monet. They were all tricked. Stunning. What do you think about this, Rondon? I just thought this was amazing.
49:45Ranjan Roy:I love this because there is this, I mean, 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 yeah 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 Like the, imagine if you posted this on blue sky, my God, if this would have looked tame, I think. But yeah, I do love this kind of, yeah, this kind of trolling is kind of amazing to watch because it just does capture where things are right now.
50:38Ranjan Roy: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.
50:50Big Technology Podcast Hosts:Yeah, no, you're totally right. I mean, there's, of course, it ran into this moment of anti-AI sentiment, right? 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. You 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.
51:28Big Technology Podcast Hosts:Don't you think? I don't know. Maybe I'm going overboard.
51:31Ranjan Roy:I wonder what the Venn diagram of the art snob in the big technology listener is. High, high.
51:38Big Technology Podcast Hosts:I would say. Very high, very high. Many, many fine painting collectors.
51:41Ranjan Roy:You have just offended them all.
51:43Big Technology Podcast Hosts: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 do worry that we're in reality hole. That's all.
51:56Ranjan Roy:No, no. My one concern. 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
52:24Big Technology Podcast Hosts:I mean I'll admit I've really enjoyed watching some of these AI videos recently no if they're
52:29Ranjan Roy:good they're good they're good if they're good they're good and there's plenty of slop out there But if it's good, it's very good.
52:38Big Technology Podcast Hosts:All right, Ronjan, 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.
52:47Ranjan Roy: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 alright alright alright alright alright alright and then the just keep living L-I-V-I-N okay that's too southern for McConaughey I think but anyways apparently Taylor Swift
53:35Big Technology Podcast Hosts:this episode we might have gotten ron john doing a texas and indian accent that is america at its finest at its finest um no but i i do think it's interesting because i there was like i used actually something called creatify
53:51Ranjan Roy: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 the ai generated influencer videos but using a real actor and they would create enough video. And even this is two years ago is pretty good. So how do actors monetize themselves in video? And is there going to be some kind of way I think is going to be one of the really most interesting ways versus they're all just going to get left in the dark and like imagine major brands using an actor's likeness and not giving a shit about it. So I don't know.
54:29Ranjan Roy: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 and Metallica and them did in the 90s. So that's what I'm hoping for. Him and Taylor Swift next to each other.
54:55Big Technology Podcast Hosts:yeah but do they testify as themselves or do their ai avatars testify because you know celebrity the demands could be high for a celebrity's time well my favorite part of matthew mcconnell is he actually sounds like his characters like like that's true like when he talks in any interview
55:13Ranjan Roy: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 re-watch wasn't that guy going to be the governor of texas
55:23Big Technology Podcast Hosts:decided not to go into politics.
55:26Ranjan Roy:McConaughey? Yeah.
55:27Big Technology Podcast Hosts:Oh, he wanted to run.
55:29Ranjan Roy:I mean, wasn't Schwarzenegger was the governor of Texas?
55:33Big Technology Podcast Hosts:No, California.
55:35Ranjan Roy:Or California. My God, you're right. I remember, we've done it.
55:39Big Technology Podcast Hosts:I mean, we do put TV stars, movie stars in elected office. Look at the white house right now. No, never, never, never. I remember flying into California when I was in college and looking out at all the houses and being like a majority of these people or really a virality 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.
56:05Ranjan Roy:Jesse Ventura, any of them.
56:07Big Technology Podcast Hosts:Yeah. Amazing. Should we end with all right, all right, all right? Is that the best way to leave people this week?
56:14Ranjan Roy:All right, all right, all right.
56:15Big Technology Podcast Hosts:All right, all right, all right.
56:15Ranjan Roy:Better than me doing a Satya accent. I'm going to work on my Satya accent all week. Okay. I'm going to come in strong next week. Dramatic readings, entire emails, pure Satya. Get ready.
56:27Big Technology Podcast Hosts:All right, we're ready, locked 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-Alton trial. So closing arguments are going on.
56:40Ranjan Roy:I'll work on my Sundar as well as Google I am.
56:44Big Technology Podcast Hosts:I don't know who am I. I guess I'll do my Zuckerberg. Oh, God. Okay. All right, everybody. Thank you, Ken, for joining us. We can't, we gotta go, we gotta go. We'll see you next time on Big Technology Podcast.
57:18Ranjan Roy:to your door shop wayfares memorial day sale may 11th through 26th at the wayfares store at edens
57:23Big Technology Podcast Hosts:plaza in wilmette wayfares every style every home every sunday we cover the week's tech news on this week in tech hi this is leo laporte inviting you to join me this week as uh berber gin from the wall street journal and paris martineau from consumer reports join ian thompson uh and we'll talk about of course open ai and anthropic they got together with a bunch of religious leaders and decided what religion AI is. They've also figured out how to keep it from blackmailing you. You just say, well, that would be wrong. This Week in Tech, you'll find it at twit.tv and wherever you get your podcasts.
From the publisher
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
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