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His Boat or Their Future?
What would you do if you had your "boat money" saved up? That nest egg you've been building toward a dream purchase, a comfortable retirement, or a ticket to an easier life?
Robbie Combs had his. He had the truck, the towing capacity researched, the whole plan. Then he put his kids in a Puerto Rican school and everything changed.
In this week's first episode, I sat down with Robbie and his co-founder Kyle Sumrow from Tech My School. Between them, they have 40 years of experience teaching in elite international schools across four continents. They've seen what world-class education looks like. But when they landed in Puerto Rico, they found something else entirely: an education system in crisis where American kids are being left behind in classrooms with no technology, no libraries, and teachers who make $1,500 a month.
Here's what stopped me in my tracks during this conversation:
17-year-old seniors reading at a 4th-grade level who have never touched a computer.
Schools where teachers use personal Gmail accounts (yes, including "[email protected]") to communicate with students because there are no school email systems.
A brain drain so severe that the government dropped the requirement for teachers to have a college degree just to fill classrooms.
Puerto Rico's PISA scores rank as the worst in the world, despite being part of the United States.
So Robbie did what most of us only talk about. He took his boat money and poured it into fixing the problem. He and Kyle launched a nonprofit that now donates $60,000 to $80,000 per school annually in technology, software, and teacher training. They've put over 1,000 devices into classrooms. They built podcast studios, media labs, and modern learning spaces. And through their "Flock Leader" program, they're training local teachers to become technology leaders in their own schools, creating a sustainable model that doesn't depend on outsiders forever.
This isn't charity. It's disruption from the inside out. And it's a powerful reminder that you don't need permission to start fixing a broken system.
"We tell kids to be brave, to be risk-takers, to go out and make the world a better place. I had to ask myself: have I just been lying to kids all these years?"
If you work for a company with old laptops, iPads, or tech equipment collecting dust, Tech My School will take them. Reach out at [email protected] or visit techmyschool.org.
Your AI is a Ferrari on a Golf Cart
Now let's shift gears (pun intended).
Everyone is talking about AI. Every company has an AI roadmap. But here's the uncomfortable stat: 95% of AI projects fail. And according to this week's second guest, the problem isn't the AI. It's everything underneath it.
Matt Soltau is the Global Director of Strategy and Operations at intelliPATH, an enterprise integration platform. He's spent nearly a decade across Europe, Asia, and North America earning the title of "The Integration Guy." His argument is simple and devastating: most companies are building a Ferrari engine and then bolting it onto a golf cart.
Here's what that means in practice. The average enterprise runs 80+ different applications. If you want to connect them all, that's potentially 6,320 point-to-point integrations. Most companies don't have that. Instead, they have a tangled bowl of spaghetti: data trapped in departmental silos, finance teams still emailing PDFs, and systems that literally don't speak the same language.
Matt broke down the problem using an analogy I won't forget:
"Data is to AI what clean drinking water is to the human body. Without real-time access to clean data, AI doesn't just underperform — it hallucinates. Just like a dehydrated person."
We also got into the future of data privacy and AI regulation, which is moving faster than most people realize:
South Korea has already passed an AI transparency law and is extending it to require full data provenance disclosure.
Canadian companies are starting to invest in on-premises AI infrastructure, refusing to send data to US servers.
Blockchain may become the "truth layer" for AI, acting as a digital notary that timestamps and verifies data authenticity.
Countries are beginning to treat personal data as a matter of national security, not just corporate compliance.
If you're a business leader, founder, or just someone trying to understand what's really happening behind the AI hype, this episode cuts through the noise and gets to the foundation that actually matters.
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The Common Thread
Two very different worlds. Two very similar problems. Whether it's an education system that's been neglected for decades or a corporate data infrastructure held together with duct tape and PDFs, the challenge is the same: someone has to have the courage to look at what's broken and actually fix it.
Robbie gave up his boat. Matt is untangling the spaghetti. What about you?
What's one system in your community or industry that you wish you could rebel against? Hit reply and let me know. I read every response.
Until next week,
Stay weird.
Cody
The Weird Canadian Podcast drops two new episodes every week. Subscribe on YouTube so you never miss one.