What is this?

I spent twenty years in networking and cybersecurity, building products, shipping platforms, and staring at dashboards that would bore the living !*#& out of most people.

Then I start pulling at a thread.

My sister shows me what happens when someone quietly buys ‘boring’ businesses and runs them well. My cousin moves down the street and starts telling me about his life as a P&C insurance producer. My partner’s friends buy and expertly play string instruments worth more than most houses, and I can’t stop thinking about how you’d insure one. I have dinner with a couple of climate advisors and don’t sleep that night.

Somehow, all of it connects: cybersecurity risk frameworks and homeowner climate exposure. Spatial computing and building inspection. Ancient agency software and modern product design. Neurodivergent pattern recognition and why traditional career paths break certain brains.

This is a blog and video series about following that thread.

I write about what I’m learning at the intersection of technology, risk, insurance, climate resilience, and the weirdly fascinating world of small business. I also write about being AuDHD, because that shapes everything: how I think, how I work, and why I’m wired to see connections that other people toss in the garbage.

Each post comes with a video. It’s just me talking. Sometimes geeking out, sometimes telling a story about someone in my life who taught me something I didn’t expect. I try to be honest about what I don’t know, specific about what I do, and occasionally hilarious about both.

If you’re into any of this, subscribe. It’s free. I publish once a week. I won’t spam you.

Thanks for reading! Subscribe for free to receive new posts and support my work.

Thanks for reading! Subscribe for free to receive new posts and support my work.

User's avatar

Subscribe to Matt Kollander

Technology, risk, and what happens when a cybersecurity PM starts pulling a very unexpected thread.

People