The Companies That Win This Decade Will Be the Ones That Learn Fastest: Inside Limitless AI

In this episode of What the Tech from Boast.AI, we sit down with Matthew Dillon, CEO and Co-Founder of Limitless AI, to discuss how AI automation is changing customer discovery—and why the real competitive advantage isn't speed, it's learning.

What You'll Learn:

→ Why the customer discovery phase is moving from Google to AI search engines
 → How Limitless AI automates the first step of the customer journey while capturing critical intent signals
 → The self-improving loop: how captured conversation data trains AI to be more effective
 → Why service-based businesses need enterprise-grade customer intelligence (and why it's now accessible)
 → Matthew's entrepreneurial journey: from lawn care at age 10 to AI automation at 21
 → How real customer use cases drove product development (not the other way around)
 → The R&D investment required to build AI agents ($10K+/month in Claude API costs alone)
 → Why SR&ED tax credits matter for bootstrapped AI startups
 → Partnership strategy: scaling through e-commerce platforms and agencies
 → How SMBs can access the same customer intent data that enterprises spend hundreds of millions to understand

Key Insights:

"The companies that win in the next decade, they're not just gonna respond faster. They're gonna learn faster. They're gonna learn about their buyers' signals, wants, needs, pain points, objections—and surface those quicker."

"It's not about automating for the sake of automating. It's tracking the conversation, understanding what the customer actually asked for, and using that to improve the AI and the product itself."

"We didn't develop an idea. We went out, integrated, worked with multiple different businesses, got proof cases, and then built a product around it."

Boast accelerates the success of innovative businesses globally with software that integrates financial, payroll, and engineering data into a single platform of R&D intelligence.

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Intro and Outro music provided by Dennis Ma whose mixes you can find on Soundcloud at DJ DennyDex.

Transcript

SPEAKER_01 0:04

Hello and welcome to What the Tech from Boasts, where we talk with some of the brilliant minds behind new and exciting tech initiatives to learn what it takes to tackle technological uncertainty and eventually change the world. I'm Paul Down, Port Post Resident Tech Journalist, and today I am thrilled to welcome to the show Matthew Dillon, CEO and co-founder of Limitless AI. Matthew and I first connected at Web Summit 2026 in Vancouver, where I first learned about his team's mission to transform businesses through cutting-edge AI automation solutions that drive efficiency, growth, and competitive advantage, a passion that we over at BOST share deeply. The Limitless team does this by providing customers with accessible, powerful AI solutions that simplify complex processes and improve productivity while fostering sustainable growth. It's an impressive mission. And along with his co-founder Nick Bruce, Matthew and his team are actively turning big ideas into real products that are useful and scalable for builders, founders, and even just curious professionals looking to explore new opportunities. Can't wait to pick Matthew's brain on how he got into the entrepreneurial and tech ecosystem, any challenges he's faced along the way, and what's on deck for Limitless AI. Without further ado, welcome to the show, Matthew.

SPEAKER_00 1:09

Thank you, Paul. So glad to be here.

SPEAKER_01 1:10

Awesome. I am happy to have you. Like I said in that little intro there, we met a few weeks back, it feels like forever ago, but it's only actually been about a month just because of how busy everybody has been with events season. But we were at Web Summit. You were kind enough to hop on camera with me for some of our social promotion. And I got a little bit of a taste about the great stuff that you guys are doing at Limitless. So rather than take it from me, I would love straight from the source. Tell us what you're looking for to do over at Limitless and what your goals are in building this business.

SPEAKER_00 1:38

Absolutely. Yeah. So our main goal, Paul, is to create a new ecosystem of AI tools, agents, and intelligence for businesses. And so we do this by deploying your traditional AI agents and we automate the first step of the conversation. Then what we do is we capture all of those analytics across the customer journey and we use that in a self-improving loop to train the AI to not only be more effective, but to then give your team those intelligence and signals that those customers are telling you so you can rework that back into your marketing. And so that's that's our main mission is developing this ecosystem for service-based businesses to implement AI agents for not only automation, but also intelligence.

SPEAKER_01 2:26

I love that. So I was taking some notes while you're talking there and a few things I want to pull up too. I love that you love with an ecosystem of tools and agents. So you're not going to pretend that there's one one size fits all solution for every go-to-market problem facing a services industry business. You want to make sure that you are wrapping them in holistic tools in a more than one basically way to address their problem because you don't want to cast aspersions or too broad a net. So I love that. Also love how you mentioned automating the first step. Could we dig into that a little bit and just what you mean exactly uh with that?

SPEAKER_00 3:00

Yeah, absolutely. So they're there's the customer journey starts with discovery. And so most people uh will look you up on Google or see your uh marketing material. But long story short, is they end up on your website and uh ready to contact you, right? And so that discovery phase is really important. And it traditionally it was Google and now it's moving over to AI search engines, right? Uh and so our first goal is to help businesses improve their discoverability across uh AI search models. And we do this by basically using a AI agent um orchestration that basically and a system that goes through and searches all of the different LLMs, uh, queries your business, looks at your competitors, looks at Google as well, and we take that data and we we then show the businesses what they can do to improve their visibility and discoverability. And so that's the first step of the automation, and that's the discovery phase, right? Um, and then from there it's the customer reaches out. Um, and that's the second phase. So how do they contact you? Do they go on the website? Do they fill out a form? Do they message your chat bot? Um, and then eventually the final stage is are they calling you? Are you booking a meeting? Um, and then actually taking that through to the final stage, which is are they then your client?

SPEAKER_01 4:16

Oh yeah. Yeah, Matthew, you as you now and we discussed, you're talking to somebody on the marketing team here. So everything that you just mentioned there is what I'm eating and breathing day to day, especially your point about how you don't necessarily find things on Google anymore. Of course, there's people who've gone savvy about it and will be like, I hate AI, let's turn it off. But the the the train has left the station. I know that's used and abused, but we got to start chasing where the opportunities actually are. And that is an AI search. And so I just know firsthand, being in the content game, it's changed how I even approach just the organic content that we're putting out there. Like videos are one component of it because I think that's very high value for like intent and making sure you're covering all the bases from that very top of funnel um perspective. But where are we thinking everything these days? And honestly, it's a lot of guessing when you don't have that data to back it up to understand exactly like these steps that go into it, because we got so good at understanding the Google of it all. But I think this is an entirely new paradigm. And we need, again, that kind of holistic, but also self-improving um system to make sure that teams are doing it, which was another point I wanted to pull back up on. So again, you're gathering those key intelligence and those intent signals, and then you're actually helping that, again, holistic kind of ecosystems of tools improve on an ongoing basis. So maybe speak to that a little bit more because I think a lot of um companies, when they're talking about their AI solutions, they think it's implied that this is something that is learning and accelerating and actually improving in its ability to deliver. But you guys bake that into your messaging. So tell me a little bit more about that.

SPEAKER_00 5:53

Yeah, absolutely. So, like I said, every conversation that is had from the first discovery phase all the way to um when the uh prospect becomes a client, we you can now that you now that we've automated that and now that we are implementing new systems, we're tracking buying signals and customer behavior signals across that entire uh lifecycle uh and through that whole journey. And so what are they what are they asking for when they're first discovering you versus what are their objections and pain points and even questions when they're you know going through that final stage in the purchasing decision? And so those kind of signals are detrimental to how we actually implement and integrate AI into the business. Um, you know, it's not about just automating and automating for successful outcome from like a standpoint of booking meetings, but is it booking meetings with customers um with the right intent signals, right? Um and so that's a lot of our focus is we're taking that marketing aspect and we're applying that into it so that way when we track a conversation, not only are we tracking the successful automation score of how well did it handle that and push it forward, but we're also tracking those signals and sentiments. So it what is the customer asking? Um what's their objection here? What does this stage look like? Uh, what was their initial um you know query that made them discover your business and your service, right? And so we take all of those insights across all of those um conversations and we then score them, analyze them, map them, and we we pull out these patterns and then we use those patterns to better improve the AI agents um and even educate the business on their buyers because uh we believe that the companies that win in the next decade, they're not just gonna respond faster, but they're going to learn faster. They're gonna learn about their buyers' um signals, wants, needs, pain points, objections, um, and they're gonna surface those quicker, they're going to improve on them quicker, and that's how they're gonna succeed. Because at the end of the day, what we all want is a business that listens and learns, and uh it's you know, the traditional service-based businesses didn't have that same ability to track all of those conversations. So this is really the kind of the new age that AI is bringing to us is actually listening and learning from those conversations.

SPEAKER_01 8:14

I I love how you phrase that. So I'm gonna jump back to one of the first points you made about it's not just automating for the sake of automating. I know that's not exactly how you phrase it, but you that's become now one of those buzzwords that people are like, uh-oh, I can smell the sniff test. That's not gonna do. But just because it's use and abuse doesn't mean that automation can't actually give you the superpowers, so to speak, that I think Limitless is aiming to arm their teams with. So it goes back to two that you're collecting the signals and sentiments, it's intent data. So again, not reinventing the wheel in terms of what we need, but in terms of actually getting it. You guys have made it accessible. Whereas it's kind of been the black box that every go-to-market team is trying to crack. Like we need to understand like what this intent data is telling us, but also how do we even get that intent data? And is this actually the intent data that we need to learn about our customers at the end of the day? Because to your point, you guys have your proprietary scoring and mapping, which delivers that data to the people, but then they can actually educate the business about the buyers too, which I think is the biggest point. Because, like you said, like businesses that are gonna succeed are gonna be the ones that can learn quickly. Learn more about their buyers too and their problems, because there's there's give and take there. You can modify what your actual service is to actually get more buyers. That's a cynical way of looking at it, but solve more problems because you know what people who find you are looking for, and maybe you solve a piece of it, but that's gonna open up a new market for you potentially if there's enough volume and critical mass behind that. So yeah, again, clearly you're talking to somebody in the go-to-market space. So this is the kind of stuff that gets me excited, but I'm very happy to hear that you guys, again, are tackling a problem that is so, so prevalent and especially timely. Um, yeah, it's literally what every marketing professional who might be listening today is listening, is going to be finding themselves in that uh journey that you're on. So taking it back a little bit, I'd like to learn a little bit about Matthew. Like I said when we met at Web Summit, I met you, but I also met your team. And I know that you're a small scrappy crew today, but you're tackling some really big problems. I'd love to learn how did this all come together? How did you meet your co-founders? How did you kind of get the idea to put this business into action and achieve so much so quickly, to be honest? I'm very impressed uh looking at how young you are, if I'm gonna be honest. I have the gray hair here, and um you you are leaps and bounds above others I've talked to uh who are at least in your age group. Not a knock on them, but more just props to you. So tell me a little bit about that Genesis story.

SPEAKER_00 10:46

I appreciate that, Paul. Yeah, it's uh it's been a journey for sure. Um I I like to bring it back to uh kind of the way I was raised. Uh when I was probably 10 years old, I started a lawn care company and uh and and yeah, a lot of landscaping. And the difference, I think, for me was um again, a big part was marketing. Like I created um uh a little trailer, I put my branding on it, and I hired my friends, and we all you know created this team. Um, and that got me motivated to just continue um in my entrepreneurial spirit. So uh I ended up doing a 3D printing company when that came out because that was a big thing and selling uh 3D printed parts and and that was a fun journey. But um at the end of the day, when um when Chachapiti was relaunched launched, I was in uh first year of university and uh I was obsessed immediately, right? Um I like I said, I was love 3D printers, I've always been in the tech industry. I love um I love space and rockets and you know just all sorts of the new tech. And so when I heard about artificial intelligence, I was immediately obsessed. And I actually started um developing. So I coded an AI resume generator. Um, failed to monetize that, but it was a cool passion project for me as I was looking to apply for jobs at the time. And then I ended up doing an AI fitness app because I wanted to see if AI could help me with my workout schedule and keep me on track. Um, and then from there, basically, uh my co-founder Nick, he was also always a tech guy, always engineering things, trying to make uh autonomous lawnmowers, cut his lawn for him, like just fun stuff. And uh what what ended up happening is he has all he also got the obsession in that bug for at the time. And we both talked and we looked at a family friend of ours uh who owned a business, a uh tree care company. And from there, we thought, how can we help automate uh part of his business and how can we implement AI? And so we started brainstorming and looking into it. And obviously, a trades business, a big portion is just getting their leads. That's that's his that's the owner's biggest problem is the marketing, getting the leads and that digital presence. He was still doing everything on pen and paper at the time. So yeah, we saw the need for it, right? And uh, we went in, we integrated AI chatbots to boost the conversion on the website and uh take those leads off of uh you know pen and paper and actually put them into a digital system. And that was extremely successful. And once we did that, we partnered with his web team and from there um networked with a bunch of other businesses and integrated more and more tools. And um, that's where we discovered AI visibility. And when that started booming, we looked into developing solutions there. And so it evolved into because we worked so closely with um these web and marketing agencies that are actually responsible for innovation growth on a lot of the service businesses, and we saw what they were looking for, which is intelligence, um, automation, uh, and as well as like a full loop picture of how to help grow these businesses. And uh that's kind of how it evolved, and we built our product around that. And we built our product around real use cases. Um, we didn't develop an idea. What we did was went out, integrated, worked with multiple different businesses, got proof cases, and then built a product around it. Um, so we only really finished building our product just in the past couple months. Um, like in the past four months. Before that, we were doing everything manual, setting up every chatbot and agent manually every single time until we built that platform uh around it, right? So it's that's kind of been the journey, and it's we're looking to grow and we're looking to continue with partners and web agencies.

SPEAKER_01 14:28

That is amazing. Okay, so Matthew, I'm gonna pull on uh a few points that you made there too, just to make sure that it gets emphasis for this audience because I love where you're coming from. First off, a theme that we have with a lot of the founders who we talked to on the show, it's that entrepreneurial spirit and that ethos that started as a child and how they were raised, to be honest. Um, I don't want to say everybody does it, but like so many folks, it's like, okay, my dad owned a shop and I had to work with him, and we it wasn't child labor, but we couldn't pay for everything that we needed. So I jumped in and I got my hands wet and I learned about computers. That's what some of the more techie side folks go. But the fact that you started with an entrepreneurial ethos and it was truly entrepreneurship. Mowing lawns, you were going out doing the lawn care and everything like that. I think the second point I want to pull up on is when you talked about even the 3D printing company that you got involved with at the early stages of all of that. What that says to me is that you have an eye for actual problem solving. And it's not necessarily about chasing something that has bells and whistles on it. Like a lot of tools come and go, a lot of new technologies will be trending and it will be something people go all in on. But is this actually solving problems or is it just something kind of like going back to the automation of it all? Innovation, just for the sake of innovating, that's not solving a problem and that's not creating a product, honestly. So the fact that you have, again, that eye for problem solving, but also just that energy for the entrepreneurship. That is awesome. Third point I want to pull on is you talked about Nick and also just how he has that kind of tech ethos. Another common theme among successful people who we talk to on the show, like yourself, is that they find people not only who they like, who they can stick with for the long haul, because your co-founder, it's a marriage. That's another cliche that gets used and abused. But it's very true. Your personalities have to mesh and you have to be able to be with somebody who you can have uncomfortable conversations with, but also who can complement your skill set. So don't want to misrepresent you guys, but the way I see it is you have that entrepreneurial ethos, you got that marketing mindset, and you also understand problem solving. That's what we need to do here, not just put something out into the market because it's AI. But then Nick has that technical prowess and he can come in and actually build new tools that, again, solve those problems. So love that. And then fourth thing, I want to call back on. Obviously, I got excited and was taking a lot of notes while you were chatting. Some of those folks for the tree services. Like, yeah, finding those good people and recognizing when there is an opportunity to complement above and beyond what your skill set is. And the fact that they're people who, again, you want to be in business with, I think that is key. So really want to just emphasize those key points because that's a recipe for success. And so many people stumble by not taking all of that to heart. Like they think, oh, I really like this guy, but does this guy just do exactly what I already have in my back pocket? Like you've got that marketing mind, you've got that entrepreneurship, you needed some technical maybe know-how to really get it off the ground. And that's where this marriage made sense. That is beautiful. And again, evolving based off the real use cases. Something that a lot of companies, when they're actually getting the funding to bring their business off the ground, kind of miss the boat on, is not understanding that you have to actually be taking in the users and making them your evangelists by modifying the solution to solve their problems. Goes back to what we were telling, what we were talking about without limitless AI actually has the ability to teach businesses more about their customers so they can evolve their product market fit. That comes because you guys have practiced what you preach. You put you actually work with people to find out how you could solve their problems using your AI technologies, and you're evolving it in kind to meet that. And yeah, I mean, I know I just repeated a lot of what you said, but really, really, really want to make sure that that hammers the point home for everybody here.

SPEAKER_00 18:18

Yeah, no, absolutely. And and that truly is the case. Like I'm uh I'm a people person and I always have been uh with that entrepreneurial and innovative uh mindset, but I always wanted to go kind of into sales. I always knew I wanted to be in tech. Um, but yeah, no, like when when I partner with um with businesses, our clients are like calling us every day almost um for advice for growth. And a lot of them invite us out to their office to help just um even do some um consulting for them, just of how they can grow and what else they can do. So yeah, we really keep those relationships to heart and um it it honestly generates more opportunities for us. Um and like that's that's our big difference. I think if we were just a tech company trying to launch another SaaS product, it it that is it's a little bit commoditized, and you have to be really good at that nowadays. Um, versus if you have strong relationships, strong proof cases, and you're really working with these people to solve those problems, um, that's where we think we're gonna shine. So we're gonna double down on that. And uh we do obviously want to innovate and and build these cool um, you know, tech products and integrate more AI and and you know, achieve that, but we also got to keep to what what works and what solves problems. So it's that balance because yeah, like you said, you don't want to innovat, you don't want to automate everything, not everything needs to be solved.

SPEAKER_01 19:35

Exactly. We don't need to overcorrect to the point where it just like is the AI just talking to itself at this point and not actually getting to the heart of this problem that we're trying to solve. I I I I I love that. Now, I'd be remiss not to pivot to the next point about kind of funding your innovation and how you guys have actually built the business around here. So, to the extent that you're comfortable talking about it, what has that look like? Because I think that's one of the biggest challenges, especially in 2026, and especially with AI uh being kind of the the boogeyman and the savior at the same time for any and all tech solutions today. So, what has your funding journey looked like?

SPEAKER_00 20:13

And yeah, just how's it going? It's it's been interesting. Like I'll tell you, we spent $10,000 in on Claude in one month just on development, um, research and development, right? And that was when we were really trying to get this platform up and running and get that self-improving loop going. And uh, it was it was a lot of money. We're still spending like close to half of that a month on development. Um, and so funding it is important for us. Uh, we've been fortunate enough to, like I said, start with those initial clients. And because we do focus so much on um the value and solving the problem, we have pretty high-ticket um clients that pay very well. Um, so we've we've been bootstrapped to this moment, but we are very much so looking to start our funding rounds. Um, we're looking for, we've applied to um the futurepreneur program, and we've been looking for investors, right? I think that's the the BDC program, right, as well. Um we're we're really trying to pull some funds together, double down, because it as you know, in marketing, it takes a lot, a lot of time, a lot of money. Um, and that's kind of what we need to grow at this point. So we're we're making those first steps. We're we're trying to figure it out and put it all together. We have some um senior advisors who are in um you know the financial sector who can really help us organize all of that. But uh yeah, our our main goal is to at least get some funding, um, take advantage of some grants. Grants are amazing in Canada. And uh I think we announced uh I'm pretty sure Canada announced more grants coming soon. So we're we're taking advantage of that and um hopefully doing a seed round eventually.

SPEAKER_01 21:51

That's amazing. Yeah, to your point, actually. Um we just published a blog this week because the prior week, Kernney dropped the new AI strategy for all and part and parcel with that. That was allusion to more funding coming. Not necessarily the official announcement of more of it, but for you and for the audience at home, a key pillar of that is Shred, which was one of the, which is the core product that we have on the both side for our Canadian customers. And more for everybody who's kind of in the room, again listening, who is at the same phase as you too, when you're just starting up on all of this, a lot of investors do want to see that you at least applied for Shred or you apply for government funding from RD tax credits. Because even though it takes that initial investment, like that 10K you put into the Claude for your initial RD, it's different from a grant in that way, and that you actually have to spend to receive your refund. It demonstrates due diligence to investors, but also if you are able to claim the funding, it makes you more attractive to investors because it shows not only are you pennywise and how you're actually putting everything out there, or pennywise with the wrong word, but you're being effective with your funding strategy and thinking strategically about it. It also shows that the government validated that you're doing something truly new and something that is truly unique and tackling technological uncertainty. And they want to be in the business for you. So that's one piece of it beyond the whole it's free cash. So it's money back that you can plug into your RD runway, and then you can do even more cool RD. So um don't have to get into whether or not you guys have claimed Shred yet at this point. I do think that there's also a misconception, too, that when you're using Claude, you're automatically disqualified. That's absolutely not the case. So we got some resources on our blog as well that I can put into the show notes here for anybody who's curious about how all of that works. But I love to hear that again, you've been bootstrapped because you're tackling a true problem. And again, you have those high-ticket customers who want to be in business with you because there is value to it. So that is going to be golden for you as you embark on kind of the funding rounds going forward. And again, anyone else in that position, explore the non-dilutive funding avenues that are available to you, especially if you're in Canada. We got the programs down here in the states too, along with the federal. There's 37 different states with 37 unique funding um RD tax credit programs. So, all to say, my echo across all the episodes that we record here on Wet the Tech is explore it. It looks good to investors and it gives you free money at the end of the day. So that was my boast piece that I had to get in there. But Matthew, now that I'm done um hopping off my uh soapbox, I'd love to hear what's up next for you and your team? What do we got to look forward to over the next few years, over the next year, or even just the next few months? I know things are absolutely moving fast for you guys.

SPEAKER_00 24:32

Yeah, right. And especially in the AI world, everything's changing so quick. Um, yeah, the next couple months for us looks like finishing out um our partnerships with certain agencies. Um, we even part were partnered with uh an e-commerce platform uh that'll be launching, I think, in the next couple days, and um basically making our our service available to 3,000 of their different um customers. So really nailing down on that distribution, um, focusing on that. And so yeah, just partnerships, um web agencies, marketing agencies, and uh getting that message out there because I think one thing people don't understand is these large enterprise companies have been looking at customer signals and buying intent um for a while now. It just takes a lot of attention, a lot of money, and they put honestly probably hundreds of millions of dollars into doing that research. Um but those you know, small, medium, and sometimes even large businesses don't have the opportunity to understand those signals. And so getting that messaging out there that now that we can pull that in using our automation, we can help smaller businesses actualize those insights and signals that enterprises have been using for the past couple of years that help them grow. So um we're really doubling down on that message so that way people understand and uh hopefully we'll partner with a lot of uh CRMs and other providers as well. Um, because like I said, we want to be that one ecosystem that really brings us all together.

SPEAKER_01 26:02

So absolutely. Oh, I I can't emphasize enough how much value there is in everything that you just listed there. I don't even want, I was about to say it helps level the playing field a little bit for those SMBs. I'm like, hopefully that's not misrepresenting, but it's a little bit of what I heard. It gives them basically the abilities that one of the big players in the enterprise space might have to get that intent data, but it doesn't make it at a far reach or a far cost, which I think is fantastic. I mean, I I already know that I'd love to connect you with our own internal teams to see what work we can do together. So um, this is music to my ears, just as somebody in the marketing space. But for everyone listening today, too, don't only follow Matthew's lead, but if you're struggling with intent data, if you're trying to get those advocates for your product, or even if you're just trying to find that product market fit, a lot of what Matthew has been talking about here and what Limitless is able to do could help you get some more firmer grounding, at least in your mission there. So yeah, Matthew, this has been a total pleasure. I cannot thank you enough for joining us on the show.

SPEAKER_00 27:01

No, thank you, Paul. I really appreciate the opportunity. And uh yeah, this is this has been phenomenal. You've recapped everything perfectly.

SPEAKER_01 27:07

Beautiful. All right, thank you again.