Unlocking AI's Financial Insights

28 May 2026 · 14 min · 5 chapters

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In short

What leaders get wrong about measuring AI ROI—AI should be evaluated as change management that augments how people think and work, not as a plug-in technology that automatically boosts returns.

Guests

Connor Grennan, who has worked with enterprise ROI measurement at Morgan Stanley and co-runs AI Mindset, a framework for “innovation quotient.” The host (Jaden) also runs AIChatDaily.com, which curates AI news.

Key claims

ROI isn’t just productivity gains (10–20%); it should include innovation transformation (potentially 10x). AI “acts like a person,” so ROI should be tied to team KPIs and how people work. AI can be costly even when outputs look great.

Notable examples

Morgan Stanley/enterprise rollout measuring ROI; Walmart productivity vs innovation; Anthropic as proof of higher ROI via innovation. Personal examples: AIChatDaily image generation cost (~$0.50/image) reduced by reusing categorized thumbnail assets; Claude agent-mode approach avoiding UI clicking by running scripts instead.

Written by AI. May contain mistakes. Listen to the episode to check what was said.

Chapters

Tap a time to open that second in VO

Exploring AI's ROI Challenges

0:53 to 2:24

Discussion on the complexities and misconceptions surrounding AI ROI.

“Connor has been absolutely talking my ear off recently about a really interesting story in Time Magazine.”

Measuring ROI: Human Work and AI

2:24 to 5:19

Understanding how AI affects human roles and productivity in organizations.

“saying is essentially like people keep looking at this as if it's, you know, a new system or a new product that you put in place and all of a sudden your ROI jumps.”

Innovation vs. Productivity with AI

5:19 to 7:48

The tension between productivity gains and innovation when implementing AI.

“Let's say you've kind of like, you know, gotten your 10, 20 % more productive over an hour.”

Real-World AI Applications and Optimization

7:48 to 10:46

Examining practical examples of AI use and the need for cost optimization.

“If I was like, how much faster can I edit a video in CapCut?”

Maximizing AI's Potential with Strategic Thinking

10:46 to 12:39

Tips on effective AI use and strategic thinking to boost business outcomes.

“Do you remember when, before the reasoning models came out, the way you could sort of like hack that was to sort of say like, it's like the chain of thought prompting.”
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Transcript

Automatic transcript. May contain errors.

0:28Welcome to the podcast. links in the description to all three of those shows. But today, I actually want to play an episode from the AI Applied podcast, a conversation I had with Connor Grennan. If you're interested in that show, you can go check it out and find more episodes at the link in the description. If not, we'll go back to normal programming tomorrow. But I want to give it a shout out because it is a show I'm super proud of. And we have a ton of fun talking about what's going on with AI. Without further ado, let's get into the episode. Connor has been absolutely talking my ear off recently about a really interesting story in Time Magazine.

1:00It says what leaders get wrong about the ROI of AI. And we were actually talking about this on the last podcast episode, I think a little bit as well. But this is a really important question. And actually, this is something I personally have been grappling with with one of my businesses in particular. I'll share some funny stories. But just because AI can do something doesn't mean AI should do something because you have to look at the ROI. And there's so many things that we have to balance. There's incredible automations you can do, but what is the cost? And sometimes the ROI is clear, sometimes it's not.

1:31So we're going to get into all of that. Kicking this over to you, Connor, what got you most excited about, I guess, this concept? Yeah, I mean, so I think I started to talk about this on the last podcast. Maybe I didn't. But anyway, so I was at Morgan Stanley just recently and really working with a big group over there about like ROI and what does ROI look like? Because I think that this is one of the big things. And we sort of am I that we get to roll out these enterprise partnerships with big organization like fortune 100 organizations like you know 25 35 000 people at a time we kind of like roll out this course with and one of the big questions obviously they have jaden is like well how do we measure roi and so we have like a few ideas on this but like our our thinking has evolved so i'm going to kind of take us through just like a couple of ways of thinking about this but then at the same time katie george who i'm a big fan of she was over at mckenzie for a long time and is now over at uh microsoft wrote that piece in time about like roi and and first of all i really agree with sort of like what she was saying about this, but I'm also, you know, what she was sort of saying is essentially like people keep looking at this as if it's, you know, a new system or a new product that you put in place and all of a sudden your ROI jumps.

2:35And she's like, it's just not like that. It's about how changing how people work. And we're like, that's exactly how we think. And so, Gene, just to sort of like kick off this conversation that we, the way we think about this is I'm going to give two ways that we think about this. Number one is we're already measuring ROI now every time we give somebody a salary, right? If you give somebody a salary for$200 ,000 in your organization, you are counting on the fact that there's an ROI on that person in that role paying that amount of money to. Now, everyone knows that there's not the same ROI on every salary.

3:08You know that sort of like people can be making the same. And on some, like the ROI on that salary is like, you know, 10X. And on some, it's like, oh, it's like, you know, 1X or 2X or something that you're basically getting your money's worth. Why? Because behind that ROI, behind that salary is a human that has to work better or work less. So if that's the ROI and AI is intended to augment how people work, now you're talking about X-ing that ROI of that salary. It's not like, and Jane, we do some work with hedge funds at AI Mindset and listen, God love you for a hedge fund to work with. I think you know that.

3:47I think you're, no, I'm not telling you anything you don't know. But the thing about hedge funds is that like, they're thinking often in terms of like, you know, algorithms and things like that. Like how can we, you know, just sort of like get a slightly better return on investment, but on huge investment on, you know, billion dollar investment. And I get that, but that's not AI. So where does the disconnect come in? It comes in because AI looks like a technology, but acts like a person, right? What AI, we, we know when we do this with big companies, what we say all the time is like, this looks like a digital transformation, but it has nothing in common with a digital transformation.

4:17It has everything in common with change management. The digital transformation comes when you switch out your old system for Salesforce, and then you have to burn down your old CRM, and then you move everybody over to Salesforce. That's a digital transformation. You've moved people from a less efficient system to a more efficient system. AI is not that. AI is how do you augment how people think and work. And so when we think about ROI, the first one, as I said, is can you look at the KPIs that you expect out of people and teams and are those things going up? And by the way, it doesn't have to be AI.

4:50Like I don't care if somebody shows up to work and they took their car and got here in 10 minutes or if they walked two hours, like they still show up at work. So in a way, AI isn't that important. Do you know what I mean? Like the AI part is not as important as what drives value, right? And then the second one that I think about, Jaden, is the innovation quotient. And we do this actually at AI Mindset. We have a whole framework around it. But the idea behind that is, and we did this with Walmart actually, like we find that productivity tends to be the enemy of innovation. And what I mean by that is like an hour of productivity gain.

5:21Let's say you've kind of like, you know, gotten your 10, 20 % more productive over an hour. Look, that's going to add up. That's great. That's awesome. That feels like everybody has the end state, but that's not how we think about ROI. We think about ROI as like in terms of innovation. How do you actually transform? If you spent that hour and just like, you know, really focus on how you would transform your role and you use AI to lift the cognitive load off you so you don't have to figure all that out. Now you're talking about ROI that's not 10%. It's like 10x. And I'm not even exaggerating. Because we see this with companies like Anthropic.

5:53This is possible. But that's when you focus on innovation. So ROI can mean a lot of different things. But what I urge people to think about is not like, we now have AI. What can we expect from our company? I'm like, it's not what you expect from your company or product. It's what you expect from your people. That's where it gets interesting. A hundred percent. And I think one interesting thing about all of this is, you know, you can, you can be like, okay, how do we optimize what we're currently doing? Okay. We're using AI, we're getting, you know, 10 % better, 20 % better, 50 % better, and all of the same processes.

6:22But the way you use AI can, or what AI can do can fundamentally shift how your entire company operates. It's like, how can I get my horse to go like 20 % faster, 10 % faster? Don't, don't use the horse, go to a car, you're in a completely different league, you're doing things in a completely different way. It's interesting. And this is probably a terrible analogy here. But it's it's kind of like, for me, the way I think about this, when I first started using chat GPT's agent mode, which was like, maybe like a year ago, I had to pay like$200 a month to use it. And everything it would try to do on my screen was doing it the way I was used to doing things.

6:56Take a screenshot of my screen, move the mouse, click a button, take a screenshot, move the mouse, click a button. It was very slow. It had glitches. It had issues. Then came along Claude and the way Claude's co-work, which has absolutely taken over and they went up 80X in like, you know, usage is because with code and co-work, what it does is it sure it might look at your screen. It might take a screenshot. It doesn't try to click the button. It runs a Python script in the background that extracts everything on the webpage and figures out where the buttons are and how everything goes. And then it formulates a plan and does like logic and reasoning to think about what you're trying to do.

7:27And then it's like running scripts to do things. I told it to edit a video on CapCut once thinking it was going to open up the CapCut app and click around the UI and edit the thing. And first it tried that for two seconds, said this is too slow. Close the CapCut app, opened the file it had created, edited the code on the file and said, okay, your video is edited. I opened it up and it had edited everything for me. This was a completely different way of approaching the problem. If I was like, how much faster can I edit a video in CapCut? And Claude opened up the screen and it clicked, you know, 20 % faster than me on the edits I needed to do.

7:57well, whatever. But he did it in a completely different way. So anyways, this applied to every business is, I think, a big thing that we should be thinking about. And then my last point on AI and ROI, which this isn't really the point. This is probably a smaller thing, but I just have it. I'm here for this. It was killing me the other day. I have my new site, which is AIChatDaily.com, and it basically scrapes 20 different sources and writes up, consolidates the news and writes It was really great articles on everything happening in the news every day in AI. So something that I was doing was I needed to generate like really good thumbnails or like hero art for every article that was being generated.

8:37And I was using OpenAI 1.4 or OpenAI 2 image model to do this. Now, I had these really amazing prompts and I had this amazing prompt cycle where I had like 20 different prompts and it would cycle through them and it was making these images that just looked incredible and it was like grabbing them from Wikipedia and then editing. Anyways, I had this like whole process that was amazing. the problem was every image was costing me like 50 cents this is a brand new site that wasn't making any money i was making like 100 articles a day um and so i mean it was like 50 bucks a day that all of a sudden i just started having to pay for all of these images and i was like i was like just because ai can do this and it looks amazing and and like i'm getting people on linkedin that are like posting like oh my gosh have you seen this new website it's like so good for ai news it's like and i'm like wow this is cool like people are finding this i was thrilled but like it was costing me 50 bucks a day for like a brand new project doing nothing and i'm like extrapolating like how much am I going to spend on this in a year anyways at the end of the day I was like I basically just changed it so that every time it made an image it automatically categorized into a category and then I made a folder for every single company and person in the world and then I just put you know 10 20 images that had been generated of every person in the world into these folders and then I just automatically picked one and cycled through so every 20 articles it kind of cycles through them okay all of a sudden I went from spending x to spending free basically on this just because ai can do something doesn't mean ai should do it you have to look at the roi and so anyways i get really excited about ai but even i sometimes realize you got to optimize this stuff i don't know if this is the point of the article but i had to share that story no i i love it because it to me it's sort of like a couple of things too right it's like like ai chat daily i'm actually a fan of it it was pretty cool like jaden was telling me about it i'm like yeah but that kind of does the same thing everything else does and i'm like oh this is actually like really good and now the funny thing guys like when we're like researching for this show jaden just goes on his own site so it's not only like an external thing but like this thing's already curated things for him too so that there's an roi on that even right because like you because jaden only has so many hours in a day so roi doesn't have to look the same as as roi always has in the past but the other thing i guess i would say is um you know jaden remember there's this so this is a tip so i don't usually do a lot of like tips right but i'll just tell you something that works really well for me.

10:47Do you remember when, before the reasoning models came out, the way you could sort of like hack that was to sort of say like, it's like the chain of thought prompting. It's like, hey, walk me through this. Hey, think deeper about this. The whole tip about take a deep breath and everybody's like, why does that work? It's because AI understands what you mean by that. It means to think deeper. And so like what I do all the time is I'm sort of like thinking like, hey, I want to do this. And I'm kind of like faster horsing it, right? I'm sort of like kind of working my way up and it's getting better and better.

11:14I'm like, this is great. And then I always do the same thing. And it's usually in Claude or Gemini, something like that. And I'll say, hey, listen, you know what I'm trying to do here, right? Can you just think like, what would you say if you're coming in and like reinventing this because you're sort of like trying to answer me and do what I'm doing? And Claude will often say it's like, yeah, listen, like, let me just take a second and think about it. So it's a weird sort of like old-timey 2023 trick, but it works unbelievably well because what it does is it's, Jaden, if you and I were sort of like building something, it's sitting back.

11:44It's like, hey, I guess we're going down this road, but what are we actually trying to accomplish? Do you know what I mean? And usually we're taking all these steps, but if the trick is to get this end state, and Claude will sometimes literally say, yeah, Conor, listen, I've been doing it this way because you've been asking me to do it this way. my thought is like if you really want to get this why don't we do it this way and there's no way jaden because of my cognitive limitations i ever would have thought about that so guys just an easy trick on this is just to sort of like pause get that 2023 tip handbook out here and just be like hey listen gemini claude chat whatever you're using just take a breath for a second this is what we're actually trying to accomplish we are trying 10x our revenue and i'm taking you down this bathroom.

12:28You're trying to help me build this little staircase over here. But is there an elevator that you could just like build, you know, sort of like over there in the background? It's unbelievably effective. 100%. Guys, thank you so much for tuning into the podcast today. If you enjoyed Connor's breakdown here, the number one thing I would absolutely recommend you have to do is go check out Connor's AI mindset course. He gets into a lot of these kind of bigger questions, you know, what people are getting wrong about the ROI with AI, a lot of ways to fundamentally shift how you're thinking about AI and how you apply it.

13:00And the place that I think this is the most valuable because he's telling me about, you know, different organizations that will buy like 10 ,000 seats for their whole organization to get this rolled out internally. That's what I would really recommend is bring this to your department, bring this to your boss, bring this to your own organization and roll this out for everyone in there to really be able to level up themselves with AI, how they're approaching AI and what they're doing. So there's a link in the description to Connor's AI mindset course. the number one course I would recommend to anyone on AI.

13:28Absolutely phenomenal, especially in enterprise. All right, guys, thank you so much for tuning into the podcast. We'll catch you guys all in the next episode.

From the publisher
In this episode, we explore the critical insights around measuring the return on investment (ROI) of AI technologies in business. Discover why simply implementing AI isn't enough, as we discuss the importance of rethinking productivity, innovation, and the overall impact on how people work within organizations.


Chapters
00:00 Introduction to AI Shows
00:55 ROI in AI Context
01:55 Measuring ROI Effectively
04:02 Innovation vs. Productivity
06:34 AI Application Examples
12:47 Final Thoughts on AI ROI


Show Links See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

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