Hey, I'm Matthew 👋

Here's why I started CTO Nuggets

I’ve spent the last 23 years knee-deep in code, architecture decisions, and the beautiful mess of building and leading engineering teams. And if there’s one thing I’ve learned, it’s that the best lessons don’t come from textbooks — they come from the moments when everything is on the line and you have to figure it out in real time.

I’m Matthew Chan. Here’s the quick version of my story: I started as engineer #3 at Wattpad, where I helped scale the platform from 2 million to 60 million monthly active users. That experience was a masterclass in what happens when growth outruns your architecture — and how to stay ahead of it. From there I moved into engineering management, led teams at Muse and League, and eventually became CTO of Blackcart, where I built and led the product and engineering orgs that powered try-before-you-buy for leading Shopify merchants. These days I’m Head of Funding Engineering at Gemini, leading an org that powers fiat movement across the global crypto exchange.

I’m all in on AI. I use it every day and it’s changing how I lead, how my teams ship, and how I think about managing people and systems. You’ll hear a lot about that here — the wins, the pitfalls, and many open questions.

Also, I’m an angel investor, fractional CTO, and startup advisor. If you’re an early-stage founder trying to figure out your technical strategy, hiring your first engineers, or just need a seasoned sounding board — I’d love to connect.

Along the way I founded a STEM education company — seven locations, 1,700+ students a year, 30+ instructors — because apparently I don’t like having free time.

Outside of work, I’m a dad of two boys, which has honestly taught me more about patience, negotiation, and managing chaos than any leadership course ever could. A few years ago my family and I packed up our life in Toronto and moved to New York — a transition that was equal parts exciting and terrifying, kind of like every major engineering decision I’ve ever made.

But none of those wins came easy. They came from hard conversations, bad calls, late-night outages, and a whole lot of trial and error. And that’s exactly what this blog is about.

Whether you’re a new engineering manager trying to figure out how to give your first piece of tough feedback, a startup CTO holding together a product that’s scaling faster than your team can handle, or a Director of Engineering trying to keep 200 people rowing in the same direction — this blog / newsletter is for you.

Every post is going to be practical, real, and a little bit battle-scarred. No theory for theory’s sake. No fluff. Just nuggets from the weeds — real talk for engineers who lead.

Let’s get into it!

— Matthew