Matthew Dillon's path as an entrepreneur started with mowing lawns when he was just a kid.

He put his branding on a trailer, hired his friends, and created a team that worked hard to tackle a problem.

Today, that same entrepreneurial spirit has led him to Limitless AI, where instead of cutting grass, he's cutting through the noise that keeps service-based businesses from understanding their customers.

The Real Problem: You Can't Manage What You Don't Measure

Here's what traditionally happens when customers find you online: They discover you (Google, AI search, reviews), they reach out (chatbot, form, phone call), they ask questions (objections, pain points), and eventually they either become a client or they don't.

That entire journey contains gold in the form of customer intent signals, objections, pain points and insights that can result in stronger customer outcomes.

But most service-based businesses aren't measuring it, either still using pen and paper or spreadsheets, if not using a chatbot that books meetings but tells them nothing about why customers are booking.

"The companies that win in the next decade," Matthew said, "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 they're gonna surface those quicker."

That learning gap is where Limitless AI lives.

The Solution: Automate the First Step, Capture the Signals

Limitless AI aims to automate discovery without trying to replace service.

When a customer lands on a website and wants to contact you, Limitless deploys AI agents that handle that initial interaction. While the agent books the meeting or qualifies the lead, it's capturing data about what that customer asked for, what objections they raised, what their pain points are.

Then Limitless uses that data in a self-improving loop. The AI learns, the business learns, and the marketing team gets actionable insight about who's finding them and why.

"It's not about automating for the sake of automating," Matthew said. "It's not automating and hoping for a successful outcome. It's tracking the conversation, understanding what the customer actually asked for, what their objections are, and using that to improve the product itself."

Think of it this way: Enterprise companies like Amazon, Google and Salesforce have all been mining customer intent signals for years and spending hundreds of millions of dollars in the process which, until now, SMBs couldn't afford

Limitless is democratizing enterprise-grade customer intelligence for the businesses that need it most.

The Origin: A Tree Care Company That Needed to Stop Using Pen and Paper

Matthew and co-founder Nick Bruce started their journey with a customer, not a traditional business plan.

A family friend owned a tree care company, which had no digital presence, and no effective way of capturing customer information. Everything was on pen and paper, and it was impacting their ability to get leads.

Matthew and Nick built him an AI chatbot. It worked; customers could contact their client digitally, leads went from paper to a system and the business grew.

That success led to other businesses thateach had the same fundamental need: Understand who's finding you, what they want, how to serve them better.

"We worked with multiple different businesses, got proof cases, and then built a product around it," Matthew said. "Before that, we were doing everything manual, setting up every chatbot and agent manually every single time. We only finished building our product in the past four months."

That's the opposite of how most SaaS companies work. Matthew and Nick didn't build first and find customers. They found customers first and built around real use cases.

Why This Matters: The SR&ED Connection

Here's where Boast's mission intersects with Limitless AI's work:

Matthew and his team have made significant investments into Claude API calls alone for research and development, building those self-improving loops, and for testing new AI capabilities. That's real R&D that's delivering powerful innovation.

In Canada, companies like Limitless that are developing new AI capabilities, automation systems, and proprietary intelligence platforms qualify for SR&ED (Scientific Research and Experimental Development) tax credits.

Limitless is already exploring funding options, including the Futurepreneur program, BDC programs, and Canadian grants. But SR&ED should be on that list too.

For a bootstrapped startup spending serious money on AI development, SR&ED can mean the difference between moving fast and moving at scale.

Key Canadian programs to explore:

  • SR&ED (Federal): Up to $6M in annual eligible expenditures, with $2.1M maximum refundable credits for CCPCs (effective 2026)
  • Provincial grants and incentives: Vary by province, but Canada has some of the most generous R&D tax credit programs in the world
  • Futurepreneur Canada: Startup funding + mentorship (Matthew is already exploring this)
  • BDC (Business Development Bank of Canada): Loans and growth capital for tech companies

To investors looking at Limitless (or any startup in this phase), the fact that Matthew is claiming government funding demonstrates due diligence. It shows the government validated that the team is doing something truly new. It shows the team is thinking strategically about their capital, while extending runway so they can do more R&D without burning through equity.

What's Next: Scaling Through Partnerships

In the next few months, Limitless is launching integrations with e-commerce platforms (thousands of potential customers) and deepening partnerships with web and marketing agencies.

But the bigger play is obvious: They're building an ecosystem. Every tool a service-based business uses to manage customers, Limitless wants to integrate with so the intent signals flow through everything.

The future Matthew sees is one where a small service business has the same customer intelligence capabilities that Salesforce gives to Fortune 500 companies.

Listen to the full episode to hear Matthew's complete journey, from lawn care entrepreneurship to AI obsession to building a company that's helping SMBs finally understand their customers.

 

About What the Tech from Boast

What the Tech features conversations with brilliant minds building transformative solutions. Hosted by Paul Davenport, Boast's Head of Content.

Learn More About Limitless AI

If you're a service-based business looking to understand customer intent, automate discovery, or unlock growth through AI, visit Limitless AI. Available to businesses across North America through agency partnerships and direct channels.

Learn More About SR&ED and R&D Tax Credits

Since 2011, Boast has helped 2,000+ companies across North America access $900M+ in non-dilutive R&D tax credits. We specialize in helping AI companies, software developers, and tech startups maximize government funding for product development.

If you're bootstrapping an AI startup while spending serious capital on R&D, non-dilutive government funding is part of your capital stack. Let's ensure you're not leaving money on the table.

Ready to fund your AI innovation strategy while extending runway? Contact Boast today.