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

What The Tech?

What The Tech?
The Companies That Win This Decade Will Be the Ones That Learn Fastest: Inside Limitless AI
Jul 14, 2026 Season 2 Episode 114
Boast 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.

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