I've Lost Friends While Building Businesses — And Gained Clarity About People
Building a business is hard. But figuring out who should be building it with you... that’s the part nobody warns you about.
My entrepreneurial journey has been a mix of wins and wipeouts. I’ve built and sold several companies, and I’ve had a few fall apart. When I look back, the successes and failures usually came down to the same thing: people.
The Engineer’s Approach to Leadership: Fixing the System, Not the Symptoms
Most leadership problems aren't people problems—they're system problems wearing people-problem costumes.
I spent years as an engineer before moving into leadership, and honestly? That engineering brain has been my secret weapon.
Bigger Isn't Always Better
Does your AI chatbot really need to understand the complete works of William Shakespeare before it can answer a customer's billing question?
Probably not.
Yet here we are—watching companies chase bigger and bigger AI models, convinced that if the first attempt didn't work perfectly, the solution must be MORE. More data. More parameters. More everything.
Employee Surveillance / “bossware†and Workplace Privacy
A few days ago, I posted about a project I built at a previous company—using Raspberry Pis to track Bluetooth-enabled devices worn by care providers. The goal? Make sure they were actually doing their job and not just billing insurance companies for time they didn't work.
We tested it at our own company HQ first. And even though the data was anonymous, people freaked out. "You're tracking us?" "Is this legal?" "Do you not trust us?"
The post I wrote about it? Also controversial.
Automation vs. Hiring: The Bet Every Leader Is Making Right Now
I've been thinking a lot about this a lot lately.
We're at this weird crossroads where automation is stupid easy to implement. A few clicks, maybe some API calls, and boom—you've replaced what used to be someone's full-time job.
AI & Job Displacement (Including Rehiring After AI Rollouts)
Businesses are firing people because of AI. Then they're quietly rehiring them.
Okay, maybe not the exact same people. But definitely the same roles. Just with fancier titles now.
You're Under Surveillance
You are being spied on and probably don't even realize it.
Not by your boss.
Not by your coworkers.
By the AI you’re talking to every day.
Synthetic Monitoring: Catching Problems Before Customers Do
If there’s one lesson every engineering and operations team learns—usually the hard way—it’s this:
The cost of an outage is always higher than the cost of preventing one.
Thankful for the Little Things (in Tech)
Thanksgiving's around the corner, and yeah, I'm grateful for the big stuff — new clients, successful projects, finally taking that long-overdue vacation.
But you know what I'm really thankful for?
Two Minute Tech Tip Thursday: Learn to Code
You don't need to be a software engineer to build something powerful anymore.
You just need curiosity — and about two minutes a day.
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