meez podcast

In the Ai weeds with Sterling Douglass. And "Build or Buy?" is now a decision every restaurant can make with their tech stack.

Headshot of Sterling Douglass

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About this episode

Josh sits down with Sterling Douglass, CEO and co-founder of Chowly, alongside Michael Jacober, for a deep dive into how AI is reshaping the restaurant and technology landscape in real time. What starts as a conversation about building versus buying quickly evolves into a broader discussion on how even independent operators now have access to tools that were once reserved for enterprise-level brands. Sterling shares how AI is accelerating product development, empowering teams across disciplines, and fundamentally changing how companies think about adoption, efficiency, and innovation.

The conversation expands into the future of SaaS, where traditional competitive advantages are rapidly eroding and being replaced by new forms of leverage like distribution, integrations, and execution speed. They explore the shift from static “systems of record” to dynamic “systems of action,” the risks of relying on subsidized AI infrastructure, and how companies can stay relevant as technology cycles compress from years to months. Along the way, they reflect on the cultural impact of AI, from how teams work to how leaders think, offering a candid look at what it takes to build and adapt in a world where everything is changing faster than ever.

Links and resources 📌

Visit meez: https://www.getmeez.com

Follow meez on Instagram: https://www.instagram.com/getmeez

Follow Josh on Instagram: https://www.instagram.com/joshlsharkey/?hl=en

Follow Josh on LinkedIn: https://www.linkedin.com/in/joshua-sharkey-406965b/

Follow Sterling on LinkedIn: https://www.linkedin.com/in/sterlingddouglass/

Follow Sterling on Instagram: @sterdb

Visit Chowly: https://chowly.com/

Visit Blanket: https://www.blanket.app/

Follow Michael: @michaeljacober

What We Cover

01:10 Introduction to Sterling Douglass and AI-focused discussion

04:20 Why AI is dominating restaurant tech conversations

07:35 Real-world AI use cases for restaurants

11:50 Adoption vs efficiency: what matters most right now

15:30 Token costs, infrastructure, and AI economics

19:40 The shift from systems of record to systems of action

24:10 How AI is changing SaaS and product development

28:45 New competitive moats in an AI-driven world

33:20 Build vs buy decisions for independent restaurants

38:00 Closing thoughts on the future of AI in restaurants

Transcript

Joshua Sharkey (00:00.148)Restaurants now have a decision that they never had before, which was build or buy. You know, like they, that wasn't an option before, but now restaurants can decide to build instead of buy.

Sterling Douglass (00:11.928)a single location group that actually built a really damn good website. Everything they did on the SEO and the GEO side, like I got really close and they even built like a little deployment pipeline. We gave them some tips and helped them out a little bit, but like that was never a thing. And it's not going to be a hundred percent of independence, but even if it's 5 % of independence, it went from zero.

Run from zero to 5%. They are so much more enabled. And I think that's going to be a key part of every single restaurant tech product is what do you have for skills? What do you have for MCPs or whatever the next version that comes out next week that makes both of them obsolete is that basically happens once in a

Joshua Sharkey (00:50.158)You're listening to Me's podcast under host Josh Sharkey, the founder and CEO of Me's, a culinary operating system for food professionals. On the show, we're going to talk to high performers in the food business, everything from chefs to CEOs, technologists, writers, investors and more about how they innovate.

and operate and how they consistently execute at a high level day after day. And I would really love it if you could drop us a five star review anywhere that you listen to your podcast. That could be Apple, that could be Spotify, could be Google. I'm not picky, anywhere works, but I really appreciate the support. And as always, I hope you enjoy the show.

We're gonna kick this off, gentlemen. And Sterling, I didn't send you topics, so I'm just gonna read the docket of things that we have, and obviously there's a bunch that I wanna ask you about. I have a bad feeling, that's not a bad thing, but I have a feeling we're just gonna, we're gonna spend 100 % time on AI, but that's okay. Welcome back, Sterling. Sterling was on the show, Mike, I don't if you know Sterling was on the show, like, I don't know, like year and a half ago, two years ago, something like that, season two.

Sterling Douglass (01:55.01)You're in seasons.

Joshua Sharkey (01:56.809)Yeah, this is season four. four? We're in season four. That's right, a hundred and, I don't know, a hundred and forty episodes now.

Michael Jacober (02:04.61)Was everyone on their best behavior? there, was there, was there cursing?

Joshua Sharkey (02:09.102)with her. Pants on. you know. could. I did. actually did. Oh, no, no, I really did. And I have them on now. So. Well, welcome back. Sterling is the co-founder CEO of Chally and among many other things, he was an actuary for a very long time. I mean, a long time ago because he's had Chally, it was about 14, 15 years now.

Sterling Douglass (02:11.306)No, you know you did.

Michael Jacober (02:14.52)No you

Sterling Douglass (02:31.598)Uh, no, we're like coming up on year 10, like in a couple of months on our 10 year anniversary.

Joshua Sharkey (02:36.814)And now you're really, really deep into AI and you started a new podcast. We're to talk about that. Yeah. First question though, and this is not going to be just, you know, an inquisition, but you got a Google hat on. Yeah. Are you, you, are you selling to Google soon?

Sterling Douglass (02:50.254)I'm I'm a big, I'm a big Google fan and I have to have been for awhile. I think Google is one of the like restaurants, best friends when it's like working, you know, and managed right. think, uh, I've always been a good big Google guy ever since I kind of started getting into restaurants, but yeah, especially recently, a lot of the stuff we do with our new platform product where we're literally just building a website that is just designed to get Google traffic. So all Google all the time, big supporters, shout out Lisa land.

Joshua Sharkey (03:19.406)Google I hope you hear this this is the best investment you could make if you were gonna buy it If you want like I I suggest a 30x multiple An ARR and then the but I mean the the the carve out for for sterling is gonna need to be at least 40 % of the purchase, but

Sterling Douglass (03:24.27)You were to acquire.

Sterling Douglass (03:38.606)Let's make sure we cut that for the cold up and that'll go over great.

Joshua Sharkey (03:43.55)Well, glad to have you, man. I'm going to share some of stuff that's on the docket and then Sterling, I also obviously I want to hear about how it's going with the with the new podcast. Shout out Mike Sermon. Great. Yeah. Greatest producer, greatest producer in the world. So, Mike, you're a beast. So here's what I got on the docket for today. One is going to be Sterling, you can pick topics because, you know, there's a lot. I'm sure you could just.

Sterling Douglass (03:55.064)Great, great, great.

Joshua Sharkey (04:08.974)jam on in terms of what you're working on now. But we didn't actually dig into the BK's Burger King's AI assistant, which has got, is a little polarized. So we can talk about that. Shake Shack launched the Project Catalyst. So that's another one. Sterling, I might actually just send you a link here because there's some, there's some source links here with some data. Third party delivery economics are up in the air. This is Pizza Chain. I know if you guys heard about this, that like, you know, walked out on Uber Eats and um,

It's going all in on DoorDash, which by the way, I don't know if you know this, can, if you go exclusive, if you have enough volume with DoorDash, you can get some pretty interesting deals. Oh yeah. 60 % of operators reported lower traffic in December. Open table demands to be the system of record. think Mike, you put that in. Yeah. SAS M &A, I'm assuming you put that in Mike. Mike, we talked a little about building SAS as a CEO.

Sterling Douglass (04:56.876)Yeah.

Michael Jacober (05:01.804)I did.

Joshua Sharkey (05:06.606)because now we can build all our own things.

Michael Jacober (05:08.6)feel like that's going to take over the conversation.

Joshua Sharkey (05:10.99)All right. Well, those there's a bunch of topics there and I'm gonna let Sterling pick. But I also we can't leave without I want to hear how it's going with your podcast, Sterling. And we do need to I just want to talk a little bit about like what we're all building the AI because fun. But you pick you heard those. And if you want, I can also just send you this link so you have a you have it your disposal.

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