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Machine Learning Podcast artwork

Microsoft's $2.5 Billion AI Investment: Street Talk

Machine Learning Podcast · 2026-07-10 · 15 min

0:00--:--

Key moments - from our scoring

Substance score

49 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality12 / 20
Guest Caliber9 / 20
Specificity & Evidence7 / 20
Conversational Craft10 / 20

Microsoft's commitment to an Applied AI consulting unit mirrors similar initiatives from OpenAI, Anthropic, Accenture, and Deloitte, but Connor challenges whether $2.5 billion spent on technical implementation is addressing the wrong problem. The core issue isn't that enterprises struggle to configure AI software; it's that employees resist change and lack genuine motivation to adopt new tools. Connor draws parallels to past digital transformations like SAP deployments, where users blamed the system rather than acknowledging their resistance to change itself. He argues that traditional consulting models, which worked for operational best practices, fail for behavioral transformation. Instead of tweaking features or pushing use cases, organizations need forcing mechanisms - processes that embed AI into daily workflows so employees have no choice but to engage with it, ultimately discovering its value organically. Jaden adds that leadership must prioritize AI adoption across the company, and that software companies shipping features every two weeks prove the competitive advantage of genuine commitment. The discussion emphasizes that the spark of personal discovery drives adoption far more than top-down mandates, and that without organizational priority - reflected in reward systems and workflows - employees won't embrace AI at scale.

Key takeaways

  • →Enterprise AI adoption fails because companies focus on tool configuration rather than changing employee behavior and resistance to change, which consulting implementations cannot solve.
  • →The spark of personal discovery in AI adoption comes from forcing mechanisms and process integration, not from encouraging employees to find their own use cases.
  • →Leadership must make AI a organizational priority through processes, workflows, and accountability systems, otherwise employees won't adopt tools regardless of implementation quality.
  • →Traditional consulting firms like McKinsey and BCG can optimize processes but cannot drive behavioral change, which is what AI adoption actually requires.
  • →Companies that rapidly ship new features leverage AI daily across their workforce, while those without AI as a priority remain stuck with business-as-usual workflows.

Guests

Connor

Topics in this episode

OpenAIAnthropicDeloitteDigital transformationMcKinseyAccentureBCGBainMicrosoft Applied AI consulting unitSAP enterprise transformation

Questions this episode answers

What is Microsoft's $2.5 billion investment in AI actually for?

Microsoft committed $2.5 billion and 6,000 employees to a new Applied AI implementation unit designed to help large companies configure AI software to their specific needs and generate meaningful returns, following similar partnerships by OpenAI and Anthropic with consulting firms like Accenture and Deloitte.

Why does Connor think Microsoft's AI implementation strategy might not work?

Connor argues Microsoft is solving the wrong problem - focusing on tweaking tools and features rather than changing how employees work and overcoming their resistance to change, which consulting models cannot address through best practices alone.

How should companies actually drive AI adoption in their organizations?

Organizations need to create forcing mechanisms that embed AI into daily processes and workflows so employees have no choice but engage with it, allowing them to discover personal value organically, rather than simply encouraging use cases or telling people to adopt tools.

What's the difference between consulting and coaching in AI transformation?

Consulting applies best practices from other organizations to optimize processes, while coaching requires changing individual habits and behaviors, which is what AI adoption actually needs but consulting firms cannot provide.

What percentage of employees actually use pilot AI tools when companies roll them out?

Connor states that when companies pilot AI tools with 5,000 to 50,000 person companies expecting wildfire adoption, typically only a fraction of those people actually use them, with the majority defaulting to complaints about features rather than acknowledging their resistance to change.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode contains some valuable contrarian thinking about enterprise AI adoption - specifically the distinction between needing process/behavior change versus tool tweaking, and the critique that Microsoft's implementation strategy misses the root problem. However, much of the content is repetitive (the treadmill metaphor and 'spark' concept are belabored across multiple exchanges), and substantial portions are filler including tangential sports references, product sponsorship, and padding. The core insight about adoption requiring individual-level behavioral shifts rather than consulting-driven 'best practices' is solid but not particularly novel to anyone who has studied change management.

The problem is not the treadmill. The problem is you.
Microsoft is trying to solve the easy problem of, like, oh, well, let's just tweak the system. When the problem is not the treadmill. The problem is you just don't want to get on that treadmill.

Originality

12 / 20

The core argument - that enterprise AI adoption fails because of organizational resistance to change rather than tool limitations - is sensible but well-trodden territory in change management literature. The distinction between 'coaching' (behavior change) and 'consulting' (best practices transfer) is presented as fresh insight but is standard organizational development thinking. The idea of using 'forcing functions' and 'expectation abuse' to drive adoption is somewhat novel in the AI context, but the execution in the conversation lacks specificity about how this actually works. The contrarian framing ('Microsoft's $2.5B bet is a miss') generates heat but the underlying argument is conventional.

You have to get people to change their habits and behaviors and everything else.
moving from encouragement to expectation abuse

Guest Caliber

9 / 20

Connor is presented as having done consulting work with large enterprises on AI adoption and behavioral transformation, which suggests practical experience. However, the transcript provides no biographical detail, company background, track record, or evidence of large-scale implementation success. The host (Speaker A) appears to be a podcast operator and AI tool builder rather than a practitioner at scale. Neither guest is identified by name or affiliation clearly enough to assess their credibility as an operator who has 'actually done it' at enterprise scale. The conversation reads more like two informed observers discussing theory than operators sharing what they've built.

So we were working with the big. So uh, AI mindset like works with big companies to sort of like transform from a behavioral standpoint
we've had uh, success on that

Specificity & Evidence

7 / 20

The episode relies heavily on anecdotal examples (a single energy company SAP implementation story, a front-end developer at a gaming studio) rather than data or named case studies. Microsoft's $2.5B commitment is mentioned but immediately qualified as 'reallocated' without numbers. No metrics are provided on adoption rates, ROI, time-to-value, or comparative outcomes across different implementation approaches. The guest mentions working with organizations but provides no named clients, project scale, timeline, or measurable results. Broad claims like 'a fraction of people use it' lack quantification. There is one specific product mention (AI Box) but it appears to be a sponsor read rather than evidence.

And I remember working with this huge um, like oil and gas or energy. Energy company.
Everybody complains because people like the old system.

Conversational Craft

10 / 20

The host (Speaker A) does ask clarifying questions and attempts follow-ups ('Connor, I'd love for you to maybe explain'), but rarely pushes back on claims or probes into contradictions. When Connor makes sweeping assertions (e.g., 'consulting model doesn't work'), the host nods along rather than challenging the logic. The conversation devolves into agreement-seeking ('A hundred percent') rather than productive tension. There are long, unchallenged monologues from Connor that lack interruption or deeper questioning. The host does offer some independent observations about feature velocity in startups versus incumbents, but doesn't use these to challenge Connor's framing. Overall, the dynamic feels more like two people validating each other's views than testing ideas rigorously.

A hundred percent. I mean, if you're going into an organization...
Yeah. And I mean the last thing that I'll say is there also is an issue in a lot of organizations...

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B64%
  • Speaker A36%

Most-used words

microsoft20spark17billion10doesn10everybody9problem9happens7organizations6jaden6change6cases6trying6applied5connor5love5consulting5

Episode notes

In this episode, we discuss common insights on Microsoft's $2.5 billion AI investment. Dive into street-level attitudes and reactions. Chapters 00:00 Introduction 00:22 Microsoft's AI Investment 00:56 Challenges with Implementation 03:00 The Behavioral Shift Needed 07:00 Role of Leadership in AI Adoption 14:35 Conclusion and Recommendations Show Links Get the top 80+ AI Models for $8.99 at AI Box: ⁠⁠ How I Grow and Scale My Business with AI: Get the AI Chat Daily Newsletter: See Privacy Policy at and California Privacy Notice at

Full transcript

15 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: I host two other podcasts. One is called AI Hustle. It's about growing and scaling your business with AI tools. And one is called AI Applied, about using AI in your career. Every once in a while, I play an excerpt of one of those podcasts on this show. To give you an idea of what it's like, I'm going to play an excerpt from Today's episode of AI Applied. We're talking about Microsoft's $2.5 billion AI bet. I hope you like it. And if you enjoy this episode, go check out the AI Applied podcast. Anywhere that you get your podcast, it's AI. AI Applied. Microsoft has just committed $2.5 billion and 6,000 employees to a new AI implementation unit. Now, this is not new. They're not the only ones that have done this. They're following what OpenAI and Anthropic both have, you know, made partnerships with different organizations. Accenture and Deloitte, if I'm remembering correctly. And I mean, there's a bunch of players that have been doing this, a bunch of, uh, private equity firms that have been kind of getting in on this and kind of investing money into, uh, these sort of AI implementation units. Now, Connor has a spicy take on this that I was reading on LinkedIn, and I was like, connor, we gotta talk about what you've been saying, because this post has been blowing up and I think it's making some people mad, but I see a lot of truth to this. So, um, and. And basically his take is that maybe what Microsoft is doing is, is not the right way to do this, which is, you know, shocker, especially when this is $2.5 billion that are about to be spent on this. So, Connor, I'd love for you to maybe explain a little bit about what these implementation units are hoping to achieve, what you think they will achieve, what you think people should do. And if, uh, this is all a

Speaker B: giant $2 billion mistake, total billion dollar mistake, everybody. Yeah, I love the hot take here, man. This is. So, by the way, I did have people from Microsoft, like, you know, writing to me and being like, it's not really 2.5. It's sort of like. That's kind of like reallocated, but the message is the same. And even people inside Microsoft are like, yeah, you know, that the headline. Don't really love the headline, but essentially like the, you know, the headline is essentially, um. Let me grab it. It's, uh, from the information originally. Uh, if you don't have the information, but it's expensive to apply to subscribe to but it's worth it. Microsoft commits 2.5 billion to new Applied AI consulting effort and then says the new unit comes as large companies. And this is important. The new unit comes as large companies have groused that it can be tricky to configure AI software to their own needs and generate meaningful returns. Jaden, I'll tell you why I am up in arms about this. So it reminds me. So we were working with the big. So uh, AI mindset like works with big companies to sort of like transform from a behavioral standpoint, right? Organizations to really transform AI adoption. And I remember working with this huge um, like oil and gas or energy. Energy company. Sorry. And we were kind of like talking about all this in this, doing this big senior leadership workshop which we do. They're like, you know, three and a half hours long or something like that. And at the end these folks were talking about when they did like their SAP enterprise transformation thing and they're like yeah, and remember how we had to keep on tweaking it because people just weren't really satisfied with it and all that kind of stuff. And I kind of paused the conversation. I didn't really want to get involved because it was a conversation kind of among them. But I was like, can I just point something out? Has this happened before? And they're like yeah, it happens all the time. I'm like this is what we think about all the time. Every time you sort of like have a new system, Jayden, a digital transformation takes place. Hey, we're now going to use Salesforce. What happens? I promise you, everybody complains because people like the old system. So what do they do? They blame the system instead of how they work. And so when Microsoft sees this, and I'm telling you this is what happens. It's not just Microsoft. I mean it's every big Lai lab, it's Google, it's anthropic, it's uh, OpenAI. It's all of these labs. And I'm telling you this is what happens. They put out a pilot of like, you know, 5,000 to a 50,000 person company. And what they say is everybody's going to use this and then it's going to catch like wildfire. And then we're going to sell our licenses to the other 50,000. What happens? A fraction of those people use it. Uh, it's just truth, right? And the whole point is that they are now getting feedback because they're like, well what's happening? Why aren't people using it? They're like, oh, I don't know, I just don't like the features or some. And they complain about the thing, which. Jaden, I'm going to sound like a broken record here, but, like, it's like complaining about the treadmill. It's like, you know what? Uh, I don't know. It's just sort of like it's downstairs or like I have to do laundry or like the features. I don't really. The problem is not the treadmill. The problem is you. Right. And why? Because we're just. We don't like change, we don't like new systems, all that kind of stuff. And everybody who's sitting there listening to the sound of my voice and being like, that's not true. AI is great. It's just people have to be more curious and they have to just find their use cases and they have to. I'm like, you've tried that, right? Has anybody responded to that? In the same way? Has anybody responded when you've shouted eat less and exercise to them? It doesn't work that way. So when Microsoft is putting all of this effort, and I understand that there's nuances to this, it's not exactly like they took a pot of $2.5 billion and 6,000 people are putting it to this, but what they're doing here, and I love Microsoft, I really do. I'm actually, you know, one of these people that I'm like a huge Microsoft M fan. But I keep telling them, like, you're the adult in the room here, like you own enterprise. Why focus on it like this, where you're like, yeah, let's come in and help you, like, tweak the systems and work on the features. That's not the problem. The problem is that what they actually need the McKinsey's for and the BCGs and everybody else's is how to get people to sort of like transform how they work. But even that doesn't work. Jayden, I promise I'm going to shut up after this. But even that doesn't work because the consulting model doesn't work. Why is that? Because when the big, uh, consulting firms, the Microsoft, sorry, the McKinsey's, the BCGs, the Bains, the Deloitte Eyes, et cetera, when they go in, what they are great at is they are great at looking at a system of like, hey, you guys do sales this way? Well, we know that from doing sales in a million other companies. The best way is to do this way. So do it like that. Or you do operations. This way, the best way is to actually do it like this. So change what you do. That's fine. That's great. That's called consulting. But coaching is very different. You can't just say to people, hey, be nicer to each other, or hey, think differently, or, hey, be more collaborative. That doesn't come from best practices from other organizations. You have to get people to change their habits and behaviors and everything else. Which is why. Sorry, now I've brought it all the way back. Jaden. Microsoft M is trying to solve the easy problem, and corporations are trying to solve the easy problem of, like, oh, well, let's just tweak the system. When the problem is not the treadmill. The problem is you just don't want to get on that treadmill. That's where I wish Microsoft would put $2.5 billion on helping people to rethink how they work and rethink processes. I just think it's a big miss.

Speaker A: A hundred percent. I mean, if you're going into an organization and you're like, hey, hey, everyone, you got to try the new Microsoft Copilot. We're signing it up on everyone's computers. These are all the 10 things we recommend doing, we're going to do on all hands every morning and share our favorite Microsoft copilot. Like, tip. I mean, that's, uh, not how they're implementing this in reality, but, like, let's think about it, right? Or we get the engineers in there and we're looking at the workflows and we're trying to, like, get the Microsoft work, you know, work copilot tools, like, embedded into the workflows and, and everything. That's not how you. That's not how you drive the big change. The big change comes from individual people getting a spark and realizing, oh, my gosh, look how capable this is. Look how much time I can buy back for myself personally, to work on the parts of my job that I like doing. Automate the repetitive, mundane parts. Like, as soon as someone gets that spark, you don't need to spend $2.5 billion to convince them to use it. They're obsessed with it. I mean, most of you guys listening to this podcast, uh, are in that ballpark, right? Like, you see, uh, you see something incredible that it can do, and you want to go all in and figure out all of the ways. And even myself, who covers AI all day, every single day, there is so many ways that I discover every day. I'm like, oh, my gosh, I never even thought of that. That's so cool. I want to try it out, right? Like, this is what drives the adoption is people being genuinely excited because they. They catch that spark and you have to ignite that spark for people. And you're not going to do it by just going and telling everyone to go download copilot onto your computer and make sure to go ask it, you know, what time the Yankees are playing at xyz. Some simple little thing, right? Like, you really gotta get them to actually get a spark with it. So that's one thing. Um, and the other thing that I think for me is just, I mean, like, it's just so much money that could be spent in so many other places. I know you said Microsoft was like, oh, it's not really 2.5 billion. I mean, it's just kind of the way the presser goes out or whatever. But I just think that there's a lot of ways. In your opinion, Connor, and from a lot of the consulting that you've done with organizations, what's the. What's the best way for people to help others in the organization catch that spark?

Speaker B: Yeah, it's. I love that you call it the spark. So the thing that we figured out, I think in this whole thing is the reason why we don't teach use cases and we teach process instead is that use cases just encouragement. Come on, guys, find your use cases. It's again, it's sort of like, come on, guys, don't you want to feel better? Like, get out there and run. Like, that doesn't work. You have to put processes in place. So for some people, you know, we do it through this whole behavioral thing, which actually drives a lot of spark because people like, oh, I didn't think of it like that. It's actually like this and not like that. So that gets a lot of people kind of like with that spark. But we can't get everybody. We just can't. So then the people that we don't get, we have to put a process in place, right? So the two. The. Let me attack those two sides, right? So first of all, Jaden, I totally agree on the spark. The only thing that drives AI adoption. It's one. First of all, it has to be driven at the individual level. Unless, um, you're talking about AI in a product, right? Like, like JY's AI box, right? Like, that's. Your product keeps getting better and better and better because of AI, right? Like, I mean, and that's. That's awesome. But for individuals at a company, when you're trying to Drive value. It has to happen at the individual level because you're paying people to drive value for your company. You don't have like some people and some robots. It's all people. So what do you do in that case? You want to have everybody have their spark. And the problem with the spark is that it often happens outside the scope of work. Anybody listening probably has had that spark, as you said. Right. I want to know like how many of you have found that spark in a personal thing versus a work thing? Because I find it's often impersonal, but. Right. You're like, oh my gosh, I spilled, you know, coffee on this and I don't. And all of a sudden chatgpt gets you out of a bind. You're like, oh my gosh. Like it doesn't usually come because somebody discovered how to write an email faster. That. Who's that? Uh, who's that like being like the genie has come out of the bottle, right? No, it's like it's not exciting. It doesn't get you sort of like wanting to stay up all night like just working with AI. It doesn't get those things. So then how do you drive that if you, if, if you sort of like if people just aren't finding that spark. Right. So again, like in our, in our training, like we get a lot of people, but we don't get everybody. So the people we don't get, we have to have like the people leaders in those organizations put processes in place, like meetings, things like that, where AI is integrated and we have specific ways of doing this. But like where AI, you can't get to the end of the day without going through AI in some way because then it's sort of like forcing people. It's almost like, hey, listen guys, to start the day at this company, we're all going to go out on a two mile walk or whatever. At some point you're going to get more and more people who are like, you know what? I actually, I'm really glad I'm doing this. You know what I mean? Like you force it in that kind of way, a forcing mechanism, because then they will find their spark through that. But that's why we don't do use cases. Because use cases are just like, come on everybody, just find your thing and you're kind of encouraging. So we say moving from encouragement to expectation abuse. Expectation abuse is. Listen, all our meetings are on the third floor and the elevator doesn't work anymore. That's how you get people healthier. Do what I Mean like you're just saying like people have to go through a process. So that's how we've had uh, success on that. And I just wish again Microsoft to m my friends at Microsoft, you are the adult in the room here. Like you are able to do this like you own enterprise. I mean obviously so does you know, so does IBM, so does you know Google, so does you know SAP, so does Salesforce. Uh, a lot of these places do. So I'm kind of speaking to them as well. But if you focus on how you get people to change their processes rather than the tool itself, then they're going to buy your product at scale, like because they'll have that spark. That's what gets me probably over as you could see, overly excited. But that's how we think about it.

Speaker A: Yeah. And I mean the last thing that I'll say is there also is an issue in a lot of organizations, um, where I feel like the companies themselves are not doing enough. And like you mentioned that forcing function is so important because I feel like the companies themselves are not doing enough to encourage or push people. Maybe they had early like bans on AI, maybe they just never encouraged it, maybe they never rewarded it. And I mean there's all sorts of absolutely ridiculous reward systems like who's using the most tokens? Okay, terrible ideas but, but like genuinely getting people to leverage these tools. Because the things I'm seeing a couple different things. Number one, a lot of the software companies I use and the scrappier, savvier startups, they are churning out new features every two weeks because they just can. And it's like, it's actually blowing my mind. There's a bunch of companies I've followed for a long time and the rate that they're able to just put out these incredible features or rebuild their entire platform is so impressive to me. And I understand why because I'm doing the same thing with all my software and platforms and tools. But I'm not seeing it from all companies. And the companies that I'm not seeing it from, for example, I mean there's just so many people where you realize that we are sort of in a bubble. There's some people that are really taking advantage and there's some that are just not. I was recently talking to someone and uh, he's a developer at like a big gaming studio and he's said, um, I'm like, I'm like, oh my gosh, like he's a front end developer. I'm like, you must just like Clyde must Be your best friend, Right? It's, like, so awesome because I'm doing this all day, right? And he's like, uh, to be honest, like, I don't know if I've tried the Claude one yet. Like, I think I tried. We had, like, a GitHub one, but then it's. We don't have it anymore. And, like, I've started using it a little bit lately. But anyways, it just blew my mind.

Speaker B: Yeah.

Speaker A: How much he didn't use it. And I'm like, if it's not a priority in your company, it's not a priority for your employees. And if it's not a priority for your employees, you're not shipping new updates every two weeks. Because you can. You're not 10x in your output because you, like, you can with AI. And so, yes, there's like, business as usual. And some companies are like, in these industries where you're kind of entrenched, you kind of have a good thing going. And business as usual works pretty good. But, I mean, if you really want to stay competitive, you have to make this a priority. I know I'm speaking to the choir here, but it blows my mind because this probably happens at least once a week where I talk to someone and, um, they're, like, not using AI. Jane.

Speaker B: This is. This is the bubble we live in. It's the bubble we live in just to close that out. Like, just remember, guys, that, like, two things. First of all, we live in a bubble that anybody listening to the show lives in the bubble. A lot of people are not, excuse me, using AI. I'm not getting emotional. I'm just going to take a sip of water.

Speaker A: Connor is incredibly emotional about, uh, this point, and people just aren't using AI.

Speaker B: I was watching England, Mexico the other night, and Harry Kane lost his voice. I'm like, how embarrassing is that? And he had a much bigger audience, so I think I'm okay. Jaden. The thing is, like, this has to start with leadership. It has to sort of, like, start with leadership and work its way down. Just as you're saying, there's literally no way for a company to sort of, like, hold people accountable unless leadership is holding people accountable. That's where that has to start. But again, we have to understand that, like, just telling people to use it is just never going to work. Guys, before I lose my voice again, like, again, if anybody saw Mexico, England, they know this. The Harry Kane interview was glorious. He lost his voice. He sounded like Kermit the Frog. Luckily, I think I've rescued myself. But here is the thing, guys. If you are sort of, like, trying to push yourself and trying to sort of, like, see how you can use this better, I cannot recommend more highly Jaden's AI Box. AI. This is my absolute favorite thing to use, because when I'm bouncing between Claude, Gemini, OpenAI, those are my kind of, like, big three. Uh, this allows you to do that for less than 10 bucks a month. It's absolutely unbelievable. Use all these models, help, you know, compare things. This is what I'm doing. And spending hundreds of dollars a month. Check this out, if you haven't already. It is unbelievably worth it. You won't regret it. And don't forget to leave a rating and review. We are so grateful for these conversations with you all, and we will see you in the next episode.

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