RSS 59: AI Scales What You've Already Got: Matt Symes on Rewiring How You Operate

Speaker A: You know, most businesses think they know their customers. They've got the data, the records, the histories, but it's scattered from team to team. Four different systems, which means nobody can actually use it. HubSpot, though, they connect it all, every interaction, every support ticket, every conversation into one platform where every team can work from. So when sales talks to a customer, marketing already has that full story. And when you know more, you grow more. Check out HubSpot.com, the agentic customer platform for growing businesses. Folks, every single company that I know is racing to become AI ready. But here's what nobody gets warned about. AI doesn't fix a, uh, broken system. If your organization's structure is broken, if your approach to growth is broken, if the fundamental ways in which you operate are broken, AI is not going to fix that. My guest today has guided over 500 organizations throughout the transformation, and he says that most of the people who he talks to when it comes to AI are actually focused on the wrong problem. Matt Sims is the founder of Simplicity, an AI transformation company that helps organizations rewire how they actually operate so they can scale and drive growth through AI he'll tell you to get your data host in order first is just a, uh, stall tactic. He'll tell you that hiring a head of AI might be the worst move that you could actually make. And he, he's built an approach that I think will make a few people scratch their head, wondering whether or not they've made the right or wrong investments. Folks, this is a conversation that is not just for entrepreneurs. It's for executive teams, for operators, for builders, for early stage companies, and for enterprises that are truly trying to figure out how can they thrive in this new age, how can they spot whether or not AI will fix the problem, or simply be a band aid that never actually gets executed on. In this episode, I'm confident that you will have at least one or two plays that you can run within your business. Folks, if you're playing the long game, you're in the right place. Welcome to the Ross Simmons Show. All right, Matt, let's start with the thing that you say that makes people uncomfortable. 14 of companies say they use AI, 2% see a return. Everyone calls it a data problem, but you call it something else. What is it actually?

Speaker B: Yeah, the data problem is an excuse. So is the Privacy and Security 1. It is like this red herring that isn't a problem. You don't need great data. You can very quickly adhere to any security and privacy posture you need with AI. What you need to Understand is what outcome do you want to get to? What workflow are you currently using to produce that outcome? Now, how do I work with the people doing that work to rewire or reimagine that workflow so that I can get to that outcome? And if you don't think about this from a workflow first perspective, if you think about it from a tools first, a data first, you're toast in this game.

Speaker A: Right?

Speaker B: Right.

Speaker A: If you were to tell them, like, step one, what is it? I can't bring someone in. I don't have like the capacity right now to make that call. But I want to do something here. I want to embrace AI. I want to do it. I'm over the data issue, I'm over the privacy issue. What's the first thing?

Speaker B: First step is you got two choices here. The first thing that I like to do is, is go to one area that is a pain in your ass. One area that takes a long time to do. It doesn't create a lot of value, but you need to do it in your business and go use AI so that you can reduce the time to do that. That's one quick win, right. That you can go do. Right. So like for example, uh, getting ready for our sales meetings or getting ready for interviews, etcetera, we always do up a dossier on the person we're talking about, and we probably talk about this later, a lot more detail when it comes to driving the speed of trust. But that dossier used to take 10 to 15 hours a week from my EA to put those together so that every morning I had the dossiers ready, ready, attached to the meeting so that I could reframe and get ready for the meeting that I had. Now, with Perplexity Computer, it is a timed agentic workflow that shows up in my inbox every morning at 6am with the next 48 hours of meetings that I have. And it's got their entire dossier built, et cetera. So an example of where 15 hours a week, right. Disintegrate it to a, uh, $200 a month subscription to Perplexity Computer. Right. So, prime example. Go somewhere that is time consuming, needs to be done, but you wish that someone didn't have to do it on repeat. That's one great way to start playing with this in workflows that matter. But if you want to get really consequential about it, you as a business are taking your business somewhere. Okay? And you are somewhere else today and in between where you want to be and where you're going. There is one business constraint. What is it? Is it a marketing constraint? Is it a sales constraint? Is it a delivery constraint? What is the workflow? What is the area of your business? What is the capability that isn't working like you want it to be?

Speaker A: Right.

Speaker B: And then go there. And so that ends up being m. One of the most powerful ways to start with AI it is CEO led. It is done around a workflow that you need to re engineer sales, marketing, whatever it happens to be. And you're doing, doing it with the people so that on the other side it goes faster, better with less resources, using what you know of A.I. uh, and that's the best way to start playing with it. And we can, you know, we can unpack this a little bit more because you get into the 4D matrix here, right? A little bit.

Speaker A: Yeah, go into that. So what's that look like?

Speaker B: So, so say you go to a sales process, for example. Okay.

Speaker A: And.

Speaker B: And I love doing this with you, Ross, because you play mostly on the marketing side, the sort of awareness, consideration, conversion, the advocacy, loyalty side. And then I play a lot on. Okay, now that you've got them in your ecosystem, how do they move from like suspect to prospect to qualified opportunity?

Speaker A: Right.

Speaker B: To conversion. And then how do they become a salesperson for you on the other side? Right, right in the sales funnel. So five steps in a process. Sales process. So say sales isn't working for you. Awesome. So you go take a look at sales and you go, okay, I'm going to work with the sales team and we're going to see how we can drive clarity of prospect, volume of the number I have velocity through the funnel cycle time, touch time, conversion rate. And then after that I got to get into a rhythm. So you sit there and you go, what part of this isn't working?

Speaker A: Right.

Speaker B: Do I not have clarity over the right customer? Do I not have enough of them? Am I not getting them through fast enough? Am I not getting enough to say yes? Where, where's the constraint? So you go straight to that constraint. Say it's, say it's a, uh, conversion. Okay, so conversion is a problem. I got all kinds of opportunity, but I can't get enough to say yes. Okay. And let's assume that you have the right client coming in.

Speaker A: Right?

Speaker B: You go and you. Okay, it's taking me. And if you look at the average reporting on sales, it takes 16 and a half months for the average B2B sale to land takes 28.89 touch points.

Speaker A: Right.

Speaker B: So your job is to decrease the cycle time.

Speaker A: Yeah.

Speaker B: And decrease the number of touches to a conversion. So what can I do with AI? Well, you know, we kind of hit on it earlier. I can make my dossiers ready so that I increase the speed of trust so that I can connect better, so then I can get the opportunity to co create. But what I have to do is I have to go and look and go where is the business constraint right now? How do I work with the team and with AI to unlock that so that it goes faster, better with less resources? And that is the way in which you can grow your business simultaneously while you integrate AI.

Speaker A: Right. So let's pretend tactically that this use case I want to keep doubling down deeper on this one. We're having too many touch points. We want to use AI. You've identified that this is a gap. The business is embracing it. They're ready to go. They've already, they're using zoom, they're using email, they're using HubSpot. Infrastructure is pretty good. But they want to use AI to like do something better to improve this. What does that look like? How would you help them figure that out? Or do you have the insights to say like, okay, for this example, touch points, we could use this. Like, what would the tactical look like?

Speaker B: So decreasing the number of touch points required to make a transaction. Maybe, maybe a story's better on this. You know, we do the classic webinar marketing stuff to get people in our ecosystem and then from that we get opportunities to have deeper discussions and then from that they convert or they don't.

Speaker A: Right.

Speaker B: Um, so I'll give you an example of a three week, three touch close.

Speaker A: Okay.

Speaker B: So we had one person come into our ecosystem and they were on a webinar, but they were like the black screen of death. You know, they just had the name. You don't really know whether they're there.

Speaker A: Yeah,

Speaker B: yeah, yeah. You're like, I, I think I'm speaking to somebody, but who knows? A week later I get an email from this person. Okay. And they're like, like to have a meeting, like, okay, so I ran open source intelligence, which is a military term for gathering data, Oent right on the company. And the person, this company happened to be one of these rural Canadian gems.

Speaker A: Cool.

Speaker B: 25 million in revenue in some weird vertical. They're all over the place, right? Ah, no idea. So it chat GPT listed out the company, listed out the market, listed out what the likely areas they would need help with. 1 through 6. This is an important thing. I'll come back to then. I ran OSINT on the individual I was meeting with. Okay. They were the OSINT open source intelligence around osint. And we open up that this guy is. He's the CEO. He is an engineer.

Speaker A: Yeah.

Speaker B: He is cost conscious. Okay. So I know this going into the meeting.

Speaker A: Right.

Speaker B: I also know that he runs ultra marathons.

Speaker A: Right.

Speaker B: I run marathons. Right. So we're both crazy. He's just another level. But we can, we can. There's a connection point.

Speaker A: Right.

Speaker B: Okay. So I go into this meeting knowing the likely things he could use help with.

Speaker A: Cool.

Speaker B: Who he is and his disposition and where the personal connection is. We get in there and I didn't really have the overlapping personal connection didn't really matter. He's like, look, I've done my due diligence.

Speaker A: Yeah.

Speaker B: I've looked you guys up a little bit. I'd like to talk about these three things. You can't make this up, Ross. One, two and three were. One, two and three. The chat GPT laid out.

Speaker A: That's wild.

Speaker B: I had already identified that number two was where the money was.

Speaker A: Right? Right.

Speaker B: So we unpack number two. And because he's cost conscious, I'm not going to the proposal yet. I'm going to talk about the business value. So I'm like, okay, well, tell me a little bit more about what it's worth to fix this.

Speaker A: Right.

Speaker B: We unpack this directionally, it's worth about $450,000 a year.

Speaker A: Right.

Speaker B: To fix this process?

Speaker A: Yeah.

Speaker B: Like, okay, awesome. Sounds great. Um, is that the only thing going on? He goes, no, I've got two people that I'm worried about. They're probably getting near the end of their career, probably worrying about retiring. Like, okay, so we got succession and 450,000. So I said, okay, this is great. Is that, am I understanding that right? Yep. I said, okay. I want to tell you first and foremost that, uh, in order for us to get in there and fix, it's going to be about $72,000 to fix this process.

Speaker A: Right? Right.

Speaker B: You could see his Adam's apple come out.

Speaker A: Right? Right.

Speaker B: At the cost. Right. He's like, oh, like, I mean, you've dealt with rural Canadian companies. 72,000 is like, you may as well just said, I need infinity dollars. Right.

Speaker A: So, so anyway, 25 million. It'll make them 450, but okay.

Speaker B: But it doesn't matter.

Speaker A: They're.

Speaker B: They're sitting there and you can like, you get the money next week. But anyway, so, uh, any, you know, you could see the Adams apple come out. And I said, look, I don't want to bother putting the proposal together. If this isn't in the. If this is in the realm, not a big deal. He goes, nope. He goes, look, I've done my due diligence. I'd, uh, like you to send me the proposal. So I send him the proposal, and he closes the next week. We got that project done. We're onto a next one. Now, why I bring this up is because if I hadn't have known the problems, the likely problems, if I hadn't, uh, known the personality.

Speaker A: Yeah.

Speaker B: I wouldn't have framed that sales discussion properly. And as a result, it would have probably taken us multiple touch points.

Speaker A: Yeah.

Speaker B: To get through it.

Speaker A: Yeah.

Speaker B: Uh, so there's an example of using AI.

Speaker A: Yeah.

Speaker B: Integrate it into the sales process at the conversion point to decrease cycle time and touch time to conversion and increase percentage.

Speaker A: I love that. That's awesome. When you look at the way you did business, let's say, five years ago versus how you do business today in the age of AI, like, can you quantify whether it's from, like, a timed perspective or value perspective, how much you're able to do more of or able to, like, focus on the bigger priorities versus back then? What's your, uh, take on how you perform now versus then because of AI?

Speaker B: So it's. It's interesting because we live in an ecosystem that's in flux and changing. Right. So you're. We're all competing in a new ecosystem that is dramatically changing.

Speaker A: Yeah.

Speaker B: But what I can say is this. We require 50% of the support labor that we required in 2019.

Speaker A: Yeah.

Speaker B: And we are doing more revenue.

Speaker A: Right.

Speaker B: With that infrastructure. So I can quantify it on a business level.

Speaker A: Yeah.

Speaker B: And I can also tell you that we're not. We're not maximized. Right. So, you know, like, I'm not. We're not even. We're not even running hot doing that.

Speaker A: Yeah.

Speaker B: So I know from a. From a gross margin actual number and from a net profit potential number.

Speaker A: Yeah.

Speaker B: How much better we are.

Speaker A: Yeah.

Speaker B: But I also think it's really important, and you kind of set it up, Ross, for me to. For me to say this. Like, we as an individual and as a company, we live in an ecosystem. Right. We live in an ecosystem of a world that's changing.

Speaker A: Yeah.

Speaker B: Regardless of where you sit politically, it's irrelevant. The straight of hermoise closing.

Speaker A: Right.

Speaker B: Means you paid more at the pumps. Uh, my guess is most of your listeners did nothing to close the Straight of her Moyes. But they all had to contend with extra.

Speaker A: Right.

Speaker B: Gas bills 100%. Okay. You live in a market that's changing. So like one of our portfolio companies, we have nine companies in the portfolio is a coffee company. When we first opened, we were the only coffee company within 200 kilometers that didn't serve burnt coffee.

Speaker A: Right.

Speaker B: Right now there's five within 15 kilometers. I didn't ask those other five to open up. But I've got market pressures. Right. And then capabilities to deliver to that market are changing. So we live in this ecosystem that's constantly in flux.

Speaker A: Yeah.

Speaker B: And as a consumer, it's a huge benefit because we get stuff much cheaper because of that environment. But as a business owner, it sucks because you're constantly having to interact in that ecosystem. Right. So I am more on the lines of. And this is why when I go through that. That little ecosystem you live in. Okay. I am not a AI evangelist, I am not a tech bro optimist.

Speaker A: Right.

Speaker B: But I am a Darwinian pragmatist. Like, you know, you can't ignore this. Right. Right. And when you think about AI in the aggregate, the IMF said that 60% of jobs in advanced economies are going to materially change in the to 36 months.

Speaker A: Yeah.

Speaker B: The World Economic Forum came out and said we're going to lose 92 million jobs and we're going to gain 170 million.

Speaker A: Right.

Speaker B: The problem, and this follows the Luddite fallacy. New technology brings new value creation which brings new jobs. It's just. It's really easy to see what we're losing. It's really hard to see what we're gaining. Right. So the example that I always use is when we move from the buggy to the car.

Speaker A: Yeah.

Speaker B: It was pretty clear we were going to need less buggy whips.

Speaker A: Right.

Speaker B: But it wasn't altogether clear what new economies were going to come out because people could level.

Speaker A: Right. Right.

Speaker B: But that was way more. And I think the same thing's going to happen with AI. The problem is it's happening way faster.

Speaker A: Right.

Speaker B: So you know, way faster. This is the fastest adoption of a technology in human history.

Speaker A: Yeah. Right.

Speaker B: It took two years to get to 800 million chat GPT users. It took the Internet 13 years to get to the same amount like that. That non linear order of magnitude is really tough for people to get their head around.

Speaker A: Yeah.

Speaker B: But you're living in that and delivering value in a market in that and both outside of it and inside of your market, it's changing. So that is the world we've all decided to enter. You as a business owner, me as a business owner. And the way that I want to approach this is how do we create more value with the time we have so we can grow the pie and share the gains.

Speaker A: Right. I love that. One of the things I've always admired, Matt, about your thinking is the systems thinking. Like, I find that you're very much able to put together the systems and think around the patterns and figure them out, break them apart, refix them, all of that stuff. And one of the things that you said is that AI scales, whatever you've already got. So broken systems just get faster. Broken. How do you find and spot when a broken system exists with one of your clients or. Or within a business, like within your portfolio, etc. Like, how do you spot that? That break?

Speaker B: Yeah, I mean, most people are in the middle of an uncomfortable puzzle they've put together that doesn't quite fit. And so if you're headed for the ditch and you add AI to that, you're just going there faster and you'll get there more violently. Right, right, right. So, uh, you all, at this point, it is so important to step back and rethink the game you're playing. Right. And so whenever we force people to step back and think of that, and we do it with all of our companies constantly. Because that ecosystem that I talked about is one that is constantly changing on you. So you step back and you go, look, every company makes a financial return because they solve a problem for a customer. They're able to solve that problem for the customer because they've attracted the right one market it they've converted themselves. They're able to deliver to them the promise that they put in front of them. And they're able to schedule enough of it to do enough gross margin per week. They're able to do that because. Because they have the right people with the right skills and the right tools and the right visibility. Okay. M. Right people, right tools, right visibility, executing marketing, sales and delivery processes. So I delight customers, so I make a financial return. When you speed stuff up, if you're a little bit off course, you just exaggerate the problems that didn't really pop up in the old world.

Speaker A: Right.

Speaker B: So it's really important. The first step is what problem do you solve for who? What's the value of solving it? So if you're describing your business from the product or service that you produce. Yeah, that's not going to work.

Speaker A: Right, right, right.

Speaker B: Like, I always give the example of, uh, of V8. Do you know anybody who likes V8?

Speaker A: No.

Speaker B: Anybody who drinks V8? It's kind of like Buckley's, right? They're getting it down the hatch because they think it's convenient nutrition.

Speaker A: 100%.

Speaker B: Right. The people at V8, though, thought they made juice, Right. And because they could make juice, they made more kinds of juice.

Speaker A: Right.

Speaker B: The net result of that is that they went from the end cap of the vegetable aisle to the juice aisle. Now, do you know anybody who gives a shit about their health who goes to the juice aisle?

Speaker A: Not happening.

Speaker B: Or the middle of the grocery? It doesn't happen. Right, right. And do you know anybody who wants juice who looks and goes, oh, I think I'll try V8 today?

Speaker A: Exactly. No, nothing like juice.

Speaker B: Exactly. So what V8 forgot is that they solved the problem of convenient nutrition. And once you realize the problem you solve, how you grow, your skew base totally changes.

Speaker A: True.

Speaker B: Right. Like. Like, what would you do if you're V8 and you knew that you solved the problem of convenient nutrition? Like, what other products might you put out, Ross?

Speaker A: Oh, AG1 would have had a hard time competing with me.

Speaker B: Well, that's exactly it. Right. You would have got the powders. Yeah. And I don't know about you, Ross, but I've had more peer pressure in my 40s to consume protein than I did in my teens to do drugs like, Jesus.

Speaker A: Protein creatine. Let's do all the E. Yeah.

Speaker B: And fiber's coming down next, apparently. Like.

Speaker A: Yeah.

Speaker B: Awesome. But I mean, the reason why I put this out, though, is the first exercise that we do with, with our clients is before I make any part of the engine hum better with AI.

Speaker A: Yeah.

Speaker B: I got to make sure that we know the client we want.

Speaker A: Right.

Speaker B: The problem we solve the value of solving. And if you can't describe it as convenient nutrition.

Speaker A: Right.

Speaker B: You don't know yet. And by the way, for your listeners, uh, Ross, very happy to give the prompt that will help them connect it. Like, because this used to take forever. You take, like, months to get to convenient nutrition.

Speaker A: Yeah.

Speaker B: Now it takes minutes.

Speaker A: Okay, let's do it. Let's get into it. How. How can you get there that quickly with a prompt? Like, what would be the approach?

Speaker B: Okay, so if you give me two seconds. I didn't know we're going here, but we'll. I'll bring it. I'll bring it up.

Speaker A: So people, uh, one of the things that I hear from folks all the time is, like, they don't know whether or not what they've created, what they've built is actually solving the problem. I'm sure you've heard of the like, is it a vitamin, is it a painkiller? All of that conversation, it's a blend of that. And also just like, what do we solve? Like, I was talking to an agency owner just earlier last week and they run a video firm and they're building videos with their clients and they're like, we're stuck in this project game where we're always pitching these one off video projects. And I'm like, yeah, that's what you do. That's your thing, that's your offer. He's like, but that, that doesn't give us the recurring. And I'm like, okay, maybe you need to ask yourself, like, what is the problem with what you're offering? And like, where do you actually fit into a video solution for your clients that's recurring? Because they exist, trust me. And helping them see that is just, it's tough. So I think folks will be excited to get this prompt from you.

Speaker B: Well, let's, let's, let's just drive it right here. I'll just show it right on the screen for those in the video. Right. So you just sit there and say, now this is really important with, with prompting that you, you give it a role. So you are a management consultant helping a company figure out their winning value proposition. You know the hard lesson? V8 learn. V8 does not sell juice. It sells convenient nutrition. It made a mistake by thinking it was a juice company and focused on innovating new juices and competing with companies like Ocean Spray. Instead of understanding this customer and realizing that the problem they solve is convenient nutrition for health conscious customers. When looking at, and this is the square brackets, your company name website serving this market. What problem do we solve for who?

Speaker A: That's awesome. That is old man. Absolutely brilliant. BT will come back, give it all to you. You could even probably ask, give us two variations so you can kind of see one or another and then like pressure test it against your own senior leadership team. That's gold.

Speaker B: And look, the client you were talking about, that is like a project based organization.

Speaker A: Yeah.

Speaker B: So you can either continue to be a project based organization and then what you have to do is you have to be the best in the world at selling flexible projects and having a surge workforce.

Speaker A: Right.

Speaker B: Because what you have to be able to do is still make the most amount of gross margin per week with the most resilient workforce. Or you could challenge it with AI. True and then turn around and say, how can I take what I do today and give me 20 examples of companies that have been project based, that have turned into recurring revenue companies and you start the wheels going. Right. But now what we're into is strategy. And the most important part of strategy, deciding what markets you're going to serve, what value is it to solve the problem for who?

Speaker A: Yeah.

Speaker B: And I know we're talking at the customer lens, but honestly, until you figured that out, don't make anything faster in your organization.

Speaker A: Right. So someone's listening to this, they're hearing about prompts, they heard you say, perplexity, computer, open source, all of this stuff. They're thinking, I need to go hire ahead of AI.

Speaker B: Yeah, yeah, yeah.

Speaker A: What do you think?

Speaker B: No.

Speaker A: Why?

Speaker B: Because if you look at 37 studies done over the last 18 months, BCG, McKinsey, etc. Studying successful transformations, the 4% who hit the K curve, not the 96 that sit in the J curve.

Speaker A: Yeah.

Speaker B: There are very predictable mistakes. Okay, so the biggest mistake you can do, we're done with pilot purgatory and tool experimentation. It is, it is not enough to buy your people tools and say, I hope you do good with it. Like, hope is a terrible strategy. Don't do that. That's just a waste of money. And the reality is if you give technicians tools and say do better, they actually take more time and get worse results.

Speaker A: Yeah.

Speaker B: So don't do that. The number two mistake though, and this is, this is, I always surface this as the most important thing for leaders to get their head around. You have to be. Your job as the CEO is to be the chief of AI.

Speaker A: Right.

Speaker B: You need to be using it to make your day to day better. You need to be using it to make your one on ones better. You need to be using it to get clarity like we just did on what problem you solve for who. What's the value of solving it? You need to be using it to understand how your workflows actually work. Like, this is your lens and you need to deeply understand it. And then from that you cascade it to your leaders, understanding it. Right. And look, if, if you're going to have AI live anywhere in an organization, it needs to be led by the CEO and it needs to live in hr.

Speaker A: Right. Why hr?

Speaker B: Because AI is not a technology, it is a teammate. It is a crew member.

Speaker A: Right.

Speaker B: In value creation. As we move between assistive AI and agentic AI. Yeah, we have a teammate that can work with us with assistive AI. You and a chatbot Right. Or we have things like Perplexity, Computer Notebook, LM, OpenCLaw, Cloud Code, Claude Cowork that are harnesses that can actually work for you.

Speaker A: Right.

Speaker B: Agentic AI. So if, if you're going to get at this, you need to think about this as a sentient and non sentient workforce or human, non human workforce.

Speaker A: Right.

Speaker B: And so it's actually better positioned to put it in AI and have it comment on your security and privacy posture.

Speaker A: Right.

Speaker B: But not act as the guardian of what we can actually deploy within workflows.

Speaker A: So with CEOs listening to this, I would hope that most of them are using AI at this point, but they've been told forever that they need to delegate. Right. Like CEOs, uh, are supposed to delegate. You have to pass things off. How do you affect an impact and drive transformation? If you're responsible for the AI approach and you need to lean into it the most, how do you appropriately transform your org to embrace this stuff? If you're supposed to own it, but you're also told that you have to delegate.

Speaker B: Yeah. So you're, you want to own the mindset and you want to own that it's being deployed, then you want to make room for. Okay, every time you go to deploy, you can rewire or reimagine a new workflow about every 30 days. So every time you're rewiring or reimagining the workflow, you do that with the leader and the team in that area.

Speaker A: Right.

Speaker B: That is how they then take responsibility for the outcomes and the performance of that workflow and the continuous improvement of that. Which means how do I continuously improve people, process technology and AI?

Speaker A: Right.

Speaker B: As a cluster that comes together to create value.

Speaker A: Right.

Speaker B: So you are delegating process area by process area or uh, workflow by workflow. And if you attack the right workflows in the right order, you just unlock business success, workflow success and you delegate leadership accountability to that area as you go through the business.

Speaker A: Right. A lot of CEOs listening to this. I'd say the vast majority are embracing assistive, as you called it, like going to a chat, asking questions, etc. Do you have use cases that you think more CEOs should be trying, experimenting with on the agentic side that you would encourage folks to like play with, experiment with or try.

Speaker B: I always distill what your responsibilities as a CEO are and for the most part they are to know the performance of the business and the performance or the capabilities within your business and the competencies and abilities of your Leaders, Uh, and then sometimes you report back to a board and then commonly you have CEOs that lean into one part of the business and they lift it up.

Speaker A: Right, right.

Speaker B: I don't know Ross, if you're still deeply involved in sales or not. I am in my business revenue for sure. Right. So I would lean more into the sales bit. So what I do is take a step back and look at those responsibilities and then go, how can AI help me with those responsibilities?

Speaker A: Right.

Speaker B: So I'll give you an example of something that I do often. I am normally as you are with keynotes. I do a number of keynotes. I'm doing workshops, AI awareness keynotes. I have a standard deck for that that is like the six hour, the four hour, the one hour, the 20 minute. Right. So I got the four decks.

Speaker A: Cool.

Speaker B: So I'll go to Perplexity Spaces and every seven days I have a research analyst that goes to all my core sources, looks at what's been said new in AI so all the sources that I trust it then compares it to the deck, offers suggestions for slide changes and why and how this either counters or augments, um, my slide deck. So every seven days I basically have a research analyst making sure that I'm staying on top of my main sources so that I'm not learning something eight weeks later that I should have learned that week. So there's one of my core responsibilities. The amount of time for me to stay up to date now.

Speaker A: Yeah.

Speaker B: Has decreased dramatically because I basically have a, a non sentient research analyst.

Speaker A: Right.

Speaker B: In perplexity computer running a time scheduled deep dive.

Speaker A: The amount of time that it takes to keep a deck relevant and timely in today's day and age is insane.

Speaker B: So it's exhausting.

Speaker A: Build an agentic like system is brilliant. I have not done that. But it makes so much sense. Like if you present and you're saying, hey, back in February this was the thing, it's out of date in June, you can't say in February this was the number one cited site. Like it doesn't matter anymore. So I love that type of model where you have an agent, uh, scanning your decks, identifying new research and providing you with that type of insight. Like that's hours saved just from that alone.

Speaker B: Well, and what it does is it immediately makes you relevant to the audience. So in early June, when late May, early June, when they were booing Eric Schmidt off the stage.

Speaker A: Right, right.

Speaker B: For talking about how good AI was going to be. True. That was the seventh slide.

Speaker A: Yeah.

Speaker B: In my deck, people going oh, God. And there's a March 2026 report from Anthropic that talks about the capability of AI versus the current uses and how much more there is. So as you look in the deck, what you have is a series of really relevant pieces for where we are today. I don't have the hours. No one has the hours to stay on top of this. So I listen to the AI Daily Brief.

Speaker A: Yeah.

Speaker B: Which is like my go to. To understand the top line. And then I have my trusted sources.

Speaker A: Right.

Speaker B: That do it. And I also. Ross. I have it scanning my email for. So the third prompt. Scan my email for every newsletter that mentions AI and compare it to the deck and see if there's anything that I need to. So. So that I don't feel like I'm missing something in there. Because eventually I'll get to those and scan them.

Speaker A: Yeah.

Speaker B: But it might be four weeks too late. So now every seven days, it's scanning my inbox under the marketing label and off it goes. But again, what I would say is take a moment and go, what are the things you're doing? Like, there's other things that's helped me with enormously. Like, I did my own360.

Speaker A: Right.

Speaker B: Okay. And, uh. But I had a. I do the 360.

Speaker A: Love it.

Speaker B: And then I sent it to my team and a reflection as a senior leader that you desperately need but will never get because everybody's blowing smoke and dancing on eggshells around you.

Speaker A: Yeah.

Speaker B: So what they weren't able to tell me. Oh, boy. Were they able to edit or audit that. And it was awesome.

Speaker A: Right, right, right. Yeah. 100. I love that. I think one of the superpowers that AI gives founders and leaders is, like, it's a lonely job, but when you bring AI along, you feel like you have this trusted source who can tell you what's real and give you some insight around.

Speaker B: Like, well, if I can hit on that, it's really important that you give it a role. So you want to say, like, for example, you can go to marshallgoldsmith AI and you can commandeer the number one coach in the world who has his give back to society, has put all of his literature online for you to interact with. But maybe it's not Marshall Goldsmith. Maybe you're going into a conversation and you have, uh, descended into ruinous empathy. You need a little Kim Scott pep talk. Right, Right. You go. You are Kim Scott, author of Radical Candor. I'm headed into this meeting. I'm worried about abc. Da, da, da, da, Da AI will take on the Persona. Kim Scott.

Speaker A: Yeah.

Speaker B: And help you frame it, or, you know, maybe you need to do scenario analysis, etc. And everybody looks at me and they're like, oh, uh, I can't. Like, I'm too. I'm not going to role play. Like, I'm not going to role play. Jesus. Like a pilot, you wouldn't let them in the cockpit.

Speaker A: Right, Right.

Speaker B: And just let them learn while they're flying.

Speaker A: True. That's true.

Speaker B: Right. So why, as senior leaders, do we not do more of this? And what I should allow you to do is spend less time lifting material and more time figuring out how you're going to integrate it for value creation.

Speaker A: I agree. One of the things I always talk about with founders is like, when we're growing up, or at least for me, I looked at athletes and I always studied athletes. And I was like, athletes practice. And the greats practice at a lot. But in business, a lot of people graduate from university and then they don't practice anymore. They don't put in any work, they don't try to learn new things. They don't, like, record their talks, they don't look at their recordings. They're just like, um, I'm who I am. And I'm like, what about the practice? Like, you have to practice. Even as entrepreneurs, leaders, you have to practice. One thing you've also talked about a lot is the founder trap. So I want to take us a little bit out of the AI world for a second, but you often talk about how companies fall into the founder trap. What do you describe as the founder's trap? What is that? What does that look like?

Speaker B: Well, it's when you haven't created a business, but you've created a prison and you've created a business where you are required in some part of it to make it go right. And you as a business owner now, you either fell in hate with how someone else was doing it, so you started it, or you're like me and you're functionally unemployable. So you have to be an entrepreneur. Right? Right. Or you really wanted to solve a problem that you didn't think anybody else was solving, like that, and then you started a business. Kind of like my grandfather, the roofer started a roofing company.

Speaker A: Right.

Speaker B: The issue is invariably and predictably, there are parts of that scale where it's not the value prop and it's not the potential of the business, but it's the way that you're leading the business that is creating and look, we're both part of the entrepreneurs organization. We see these entrepreneurs all over the place who kind of hit that 1.8 to uh, $2 million range. And congratulations, you're in the 6%. Only 6% of businesses ever get past a million. But they can't get past that. They're just caught. So the Founders trap is when you are caught in your business and you are required in one part of that business in order to make it go. And what we want to do is help business owners like, look, if you want to be doing that because it fills your bucket, awesome. Like build the business. So you do that. But don't have a business where you're required to be there. I was once working with a home builder and uh, he said, matt, I just really want to do landscape landscaping.

Speaker A: Right.

Speaker B: I'm like, awesome, well then let's build a business so you can landscape two days a week. And he's like, well, but I'm the third best landscaper and I only have two other ones. I said, well, I don't really care if you like the landscape.

Speaker A: Right.

Speaker B: Then let's build it. So anyway, it was a, it was about a um, 12, 15 million dollar business at the time. It's now a 50 million dollar business and he spends two days a week landscaping.

Speaker A: That's it.

Speaker B: Because he loves it.

Speaker A: That's the only love he wanted it.

Speaker B: Right. So the Founders trap is one where you are stuck playing a role.

Speaker A: Yeah.

Speaker B: Because your business doesn't function without you playing that role.

Speaker A: Right, Right. Talk me through how simplicity supports brands founders with this whole thing, do you have to be a portfolio company? Like how does it all work? Talk me through the simplicity ecosystem.

Speaker B: M. At large, we have three ways we play with companies. So we have our own portfolio of companies that we have invested in or taken minority positions in where we're enabling them. Right. So nine companies that should do about 35 million this year. And I share that openly to say we've got skin in the game. And when we talk about how to turn organizations around like our, our wallet hurts when we don't get it right. But we're in verticals like law, preventative health, psychiatry, construction, coffee, as I told you. Right. When the hobby gone wild. But anyway, um, learned a lot about product anyway, so. And then we have a company that does large transformations called Simplicity where we work one on one with organizations. Generally those organizations are already doing at least 5 million plus in revenue and they have enough that they want the one on one attention. And it's worth the one on one attention because you can unlock so much value. Right. Like I often say in a strategy session with a 20 to 60 million dollars company, we can trip over a $600,000. Just do it.

Speaker A: Right, right.

Speaker B: But in a million five company or a $500,000 company, it doesn't matter what you do. You're not finding a $600,000. Just do it. It just, it doesn't exist. Right. So simplicity is the one on one. And then we have Levership and Levership is for those founders are who somewhere between 500k and 5 million. And it's our cohort approach. We do three standard things, whether it's with our portfolio, whether it's one on one or whether it's leadership. The first thing is we introduce a strategic cadence, which is a battle rhythm for how you make decisions. And if you look at all of the great organizations, they have some sort of rhythm. They operate under cadence of accountability, calendar of commitments, battle rhythms with the military. Calls it, uh, call it whatever you want. We help companies stop two days a quarter, half a day a month, one hour a week, two days a quarter to make the big decisions. Where am I going? 10 year, 7 year, 3 year, 1 year connected to 90 days. Then you get into a 90 day sprint, a 4 week work plan. You check in on that every week for an hour to make sure that something hasn't blown up on Tuesday and taking you away from what you said you were going to do. Yeah, right. Every month you're doing a minor check in to go like has the world changed? And what that does is it allows you to make the big decisions and then just go to work for four weeks.

Speaker A: Right.

Speaker B: And stop changing your strategy every random Thursday when something happens.

Speaker A: Okay.

Speaker B: So we implement that battle rhythm that comes with a balanced scorecard. We have the conversation around what problem do you solve for who? What's the value solving it? We, we just mature the way the business sees success. Love, um, it and what they're and how they're articulating what they're building. From there, there are no doubt workflows that need to perform better. So every 90 day sprint or every 30 days is what we're getting to with mature organizations. You are rewiring.

Speaker A: Yeah.

Speaker B: A workflow.

Speaker A: Cool.

Speaker B: Right? So changing form, fitter function of how that is deployed. And this is reviving everybody who can do process improvement because in order for AI to work for you, assistive can do task level stuff and agentic can do multiple tasks, but it can't do the full job Right. So if you don't know how the sausage is made, you really can't benefit from AI.

Speaker A: Right, right.

Speaker B: So you have to unpack how the sausage is made and then make it in a better way. So we will help you rewire workflows. And then the third component that we come into is there's a whole bunch of enabling stuff, whether it's finance or whether it is hr, you know, kind of that back end shared services.

Speaker A: Right.

Speaker B: Where we can rent that out in a temporary fashion while you're in between either stages of growth or when you're in between personnel, if you will. Right, right. So that's how we help. And we're always around to coach the leaders as we go.

Speaker A: Yeah.

Speaker B: But those three big areas, we got simplicity, that does large scale, we got Levership, that does the small and micro. We do it in a cohort fashion. It's completely accessible. It's like 1500 to 3750amonth. It's decimal dust compared to what you'd pay for the other stuff. And then in rare occasions it works and we partner and take an equity position where one plus one can equal three.

Speaker A: Right, right.

Speaker B: And we've learned. I've learned I am much more energized working with highly motivated operators where I can enable them at the speed they want to go.

Speaker A: Right, right, right.

Speaker B: And if you look at all of our companies, we're basically betting in the worlds where AI is going to have a more difficult time playing.

Speaker A: Right, right.

Speaker B: And then enabling it with AI.

Speaker A: Yeah, that's fair. Makes sense for yourself. Like looking back over the course of the years, did you ever fall into founder trap?

Speaker B: Uh, and arguably I'm still there when it comes to simplicity. Simplicity is our major transformation. It takes an incredible amount of experience to help guide a larger company. Because you're living in the abstract world, you have to be able to see systems, you have to be able to see second and third order consequences. And we had to make a decision on whether we were growing another McKinsey or not. And we decided that I didn't. You know that project world you talked about earlier where the guy's trying to get out of.

Speaker A: Right.

Speaker B: That's where we were five years ago. Right. And I said, wait a minute, this is, this is insane. I have no interest. And, and look, when you grow somebody who can do the things that we're trained to do, after a couple years, why are they still doing it with us? They can go out and make half a million to a million bucks a year. On their own.

Speaker A: Right, right.

Speaker B: And have an awesome life. So it's, it's really hard to grow a uh, high end management consulting firm. And you're also for as, as fun as it is to help organizations transform, you're always building other people castles.

Speaker A: Right? Right.

Speaker B: Which you're invited back to, but they're never your castle.

Speaker A: Fair. Fair.

Speaker B: Right. And, and, and look, here's the classic. And you've probably faced this as a marketer like in the beginning you're like some form of ulterior being that's bringing them lenses they've never heard of before. And you're, you're the best thing since sliced bread. And then you're a partner, but a high paid one. And eventually you're someone they don't want to pay for anymore.

Speaker A: Right, right. Yeah.

Speaker B: So it's never a long term relationship. It's always a situationship of somewhere between 18 and 36 months.

Speaker A: Yeah, no, that's fair. That makes sense. When you think of the future of Simplicity with AI, like what does the next wave look like? Do you see you're not going to be the mini McKinsey. Like what does the future look like?

Speaker B: There are three parts. One, we have re engineered or re geared our sales process at Simplicity to be around large transformation clients where we can make a societal impact.

Speaker A: Cool.

Speaker B: So like we're working deeply in health care and that's near and dear to my heart to help people transition from one level to another level of health. And we're working deeply within a couple of other regulated industries. We're working with utilities and you know, sorting the equation of the future of power generation and how we're going to navigate that is, you know, it's, it's, I uh, mean basically the abundance of society runs on sustainable kilojoules per person per hour.

Speaker A: Right.

Speaker B: So when, when I can help in that area and when we can deploy our resources there, that's, that's motivating. So we pick a select few with Simplicity where, where we believe we can play a, a really important role. And then at Levership we just want to help as many small businesses as possible. Not play the game on hard, want to help them get out of the founder's trap. So we are driving a cohort approach to that and really excited about scaling that because that is very scalable.

Speaker A: Yeah.

Speaker B: The exercises are well baked and proven. They drive roi. The patterns are predictable. Certain type of company, certain size. They run into consistent problems and you can predict them um, pretty, pretty accurately. And then on the portfolio side I'm just, I'm really looking for the right partnerships. I want to build between 100 and 250 million dollar portfolio. And I say out of Atlanta, Canada. But we have, we just uh, acquired a minority position in a company in Ontario and I do believe that we will be out of Atlantic Canada, but we will be at least nationwide.

Speaker A: Right.

Speaker B: And then we'll see what the geopolitical situation looks like. But I can see I've got a few tentacles in, in the UK and Europe and it would be fun to play a European Canadian. That's growth engine. So that's, that's the future for, for us.

Speaker A: I love it. That's awesome. So you started this with your dad, your brother, childhood friend, and now you folks have built this massive thing. What does mixing family with business look like? Does it, was it hard? Was it rewarding? Was it all of the above? Like talk me through what that journey was like.

Speaker B: Yeah, uh, the quick answer is yes. The longer answer is entrepreneurship is like a uh, self development exercise disguised as a business, business pursuit. And it will expose every one of your flat sides and slap you with them, um, until you learn the lesson. And it was incredibly rewarding to start with dad and Mark, but it was also excruciatingly difficult. You know, you always knew that they had your six and you didn't have to worry about that, which is, you know, 1, 1 check mark in favor of nepotism and in favor of family businesses. And on the other side, because you're so close and so tight, there are areas that you will go to in debates that you would never go to with other people.

Speaker A: Right.

Speaker B: It was honestly, we had to learn a whole bunch of new skills. Right. Uh, in order to make sure that we showed up with intention and were impeccable with our words. And we also, you know, my dad left the golden handcuffs at a multi billion dollar family business to come start simplicity with my brother and I and the platform that he allowed us to launch from the standard of living, the opportunity that I have in this world is because of that decision.

Speaker A: Right.

Speaker B: And you know, we were able to support him as he went through his terminal illness and the business allowed us to do that without any problem. Right. Uh, and then my brother, in January of last year, we sat down, had a conversation, just talked about and you know, you would know this from the EO stuff, I mean, and I do this with founders. What's your best life?

Speaker A: Right.

Speaker B: And then how does your business enable that? And my brother and I had some really deep discussions November December and January. And. And my brother eventually decided that he wanted to focus on one thing. He wasn't passionate about strategy. He wasn't passionate about AI. He's a blue collar hard worker with this knowledge base. And so he went to work as the COO at Fundy Pros.

Speaker A: Right.

Speaker B: And so, you know, I would say that I have gone through every emotion that you could imagine in a family business, from the depths of despair to the elation of being able to share major wins with the people that are closest to you.

Speaker A: Yeah.

Speaker B: I think about, I think about what dad wanted to leave as a legacy. And, you know, because he wrote out four years after being given that one year sentence, he was able to communicate that, you know, he was, he was very, very happy with the legacy that he had lived.

Speaker A: Right.

Speaker B: And I'm very grateful.

Speaker A: That's awesome.

Speaker B: For the time with him.

Speaker A: That's awesome.

Speaker B: Right. And I look, if I can go one more story. I, uh, Yeah, I remember in 20, I think it was, I think it was 2010, you know, how you, you interact with your dad and your dad's your dad. Fine. And you know, you argue with them and you don't really see what your dad does outside of your interaction with them. And he asked me if I would join him for a session that he was facilitating with the Ontario Junior Hockey League. And we walk into this thing and there are billionaires and there are a couple people who are trying to put two pennies together and hoping a dime comes out. And you got like the whole gamut of people in there. And he's facilitating this league that needs to contract, that needs to make impossible decisions with every spectrum of the socioeconomic reign in there. And over that weekend, it wasn't my dad anymore.

Speaker A: Right, Right.

Speaker B: It was. I was like, holy, this guy is unbelievable at, uh, what he does.

Speaker A: Right. He's him.

Speaker B: And not only is he unbelievable, but this is important work.

Speaker A: Right? Right.

Speaker B: Like, like getting alignment and helping leaders commit to something and then going to create something. Right. I mean, like, look, we all think about getting it right. It's. It's often not about that. It's often about getting it less wrong faster.

Speaker A: Right.

Speaker B: And it's. And it's often about not making the right decision, but deciding something and making that decision. Right?

Speaker A: Yeah, yeah.

Speaker B: And bending. You know, you got the delusion of, you know, was it the reality distortion field that Steve Jobs talked about? But.

Speaker A: Right.

Speaker B: But founders have to live in a world where they have. They already know something's possible before it's done. And my Dad's great skill.

Speaker A: Yeah.

Speaker B: Was being able to take people who had that vision and help them get alignment with a team to drive towards it.

Speaker A: Right. Matt, you fast forward 60, 70 years from now, your little one might be on a podcast having a conversation with someone, and they're talking about you, your legacy. What, what's the hope that you have for the way in which you leave this world as better or whatever? Like, what are you hoping to kind of leave as your give back to your littles, the world at large and the work you do?

Speaker B: You're a father of young children as well, so you, you know that, that question hits. Look, most of us are going to be forgotten within two generations, so the only thing you really leave behind are those that you showed up for. And I was an older dad, which I'm grateful for because I have more patience than I would have if I was younger. And I'm also grateful for the entrepreneurs organization and the connection with Warren Rustin and the deep, challenging questions that forced me to ask the bigger ones. And so when I'm working with others and the exercise that I've always done is I've written my own obituary, which helps me understand my legacy values. And I've done it from four perspectives, right. I've done it from the friends, family and close relationships. And I want them to say, he was there, he showed up, and then I've done it from a community standpoint and there has to be. When I talk to you about what AI has brought to our organization in terms of less people, more profitability, I think it's also important to note that everybody in our organization takes at least five weeks vacation. Everybody's paid in the 90th percentile.

Speaker A: Right?

Speaker B: And so when you think about it, everybody has more time and has more money compared to their peers with that time to be able to show up. For those that matter, we have a take what you need policy when it comes to vacation and leave. So we've had people, you know, you got deaths in the family, etc. That you need to be there for. And we have a, uh, we have a common principle in our, in our organization. If you can't be there for those that you love when they need you, either in times of despair or hopefully times of celebration, graduations, concerts, then what are we doing this for?

Speaker A: Right? Right.

Speaker B: So the community that we want to influence, the ones that I have, you know, that are directly in my charge, and then the ones, uh, on the, on the halo of it, I want to create an environment where they knew that when they came to work that they were cared about and for. And then on personal and professional, you know, it's. I love getting up every morning, and so I want to be able to say from a personal and professional stuff that he, that he went after life, um, and that he did things right. And. And then I want my kids to always say he was there.

Speaker A: I love it. Matt, if people want to find more about you, where can they go to learn more about you, your work, all that good stuff?

Speaker B: Well, they can head to mattsims CA M a t T S y M e S ca. That's my personal website. That's where the keynotes and all that kind of fun stuff is. Or they can head to Simplicity Ca with a Y, although we have both S y A M Simplicity CA or Levership.com and they can get in touch with us. And, uh, I say sometimes on these podcasts, the InfoImplicity CA Stow goes to my inbox to triage. So if you want to get at it, there it is.

Speaker A: I like it. Matt, thanks so much for all you've done for the local community, for the EO community, and thanks for coming on the podcast. Really appreciate it. I'll be sure to drop your links in the show notes. Thanks again and I'm sure I'll see you soon. Appreciate your time.

Speaker B: Uh, thanks, Ross.