
Paul Cheek
Senior Lecturer at MIT Sloan and Executive Director of the Martin Trust Center for MIT Entrepreneurship; bestselling author of Disciplined Entrepreneurship: Startup Tactics and founder of the AIDE Institute.
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Sep 17, 2026
Paul Cheek, MIT Senior Lecturer, AI Strategist, Entrepreneur & Author
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Willy WalkerHOST
So dive in on those two things, because we're right, we're right on top of those two things.

Paul CheekGUEST
The return on investment with AI, it's something that everybody's looking at and thinking, where's the short-term ROI? We're not seeing it.

Paul CheekGUEST
Are we looking in the wrong places? Are we doing the wrong things? And the thing that I always come back to, Willie, is the fact that when a high school student decides to go to university, they say, I'm going to go do, let's just say for sake of example, a four-year undergraduate degree.

Paul CheekGUEST
They're making a significant investment of time, let's say four years, and money, the cost of tuition, right? And when I think about that, I think they're doing that.
7 MINS LATER

Willy WalkerHOST
What are some of the either tactics, tricks, hacks that you've seen scaled organizations take to be able to get both the board and the C-suite on that learning curve?
[ScaleX Bite-Size] Using ChatGPT Isn't AI Transformation with Paul Cheek
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Paul CheekGUEST
But I might pause there just for any reflections you might have on that model and how you see that manifesting for SMEs.

Brendan McGurganHOST
But I haven't met anyone yet who has AI deeply embedded in their organization.
[ScaleX Bite-Size] The Business Model Built for the AI Era with Paul Cheek
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Brendan McGurganHOST
What does this look like? If you describe to our leaders the traditional org structure, just so that we're all aligned on what that looks like, and then how that differs from the AI-driven enterprise.

Paul CheekGUEST
Yeah, and we can talk about org structure and org charts and things like that, how we organize.

Paul CheekGUEST
But I want to maybe start with the model, the definition, and then how that manifests within a company.

Paul CheekGUEST
traditionally, we've looked at two primary models of business and business growth.

Paul CheekGUEST
And one would be the SME, the small medium enterprise that scales linearly with limited upfront resource requirements, serves a local or regional market, but it hits a capped level of growth.
AI-Driven Enterprise: How SMEs Can Unlock 10x Efficiency with Paul Cheek
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Brendan McGurganHOST
So what does this look like if you describe to our leaders the traditional org structure, just so that we're all aligned on what that looks like and then how that differs from the AI driven enterprise?

Paul CheekGUEST
Yeah, and we can talk about org structure and org charts and things like that, how we organize.

Paul CheekGUEST
But I want to maybe start with the model, the definition, and then how that manifests within a company.

Paul CheekGUEST
Traditionally, we've looked at two primary models of business and business growth.
29 MINS LATER

Brendan McGurganHOST
What's your vision for the organizations of the future? What does a workplace look like and what work are people actually doing? When you're sitting back on, I see a world that looks like, what does
No One Works Here: What AI Actually Changes About Work
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Paul CheekGUEST
But no, like a concrete example, I want to come back to your question, but I think it's important to flag that up front.

Paul CheekGUEST
Now, I would also say many people jump to something that is not actually an organizational priority.

Paul CheekGUEST
And we could talk about the four characteristics that I look at for any opportunity to use AI.

Paul CheekGUEST
I see a lot of people who look at whatever that very clear KPI is in front of them.
35 MINS LATER

Jason BaumgartenHOST
And then, like, what's an example that maybe surprised you and what did you learn from it?