I run four technology companies and fix the problems inside them.

In 2008 I was at Loyola, buying and reselling tech to help pay for school. It started the way it starts for most people. Find something underpriced, buy it, sell it for more.

Do that enough times and you figure out the buying is the easy part. You have to know what to pay before you pay it. Inventory sits. Prices move. Customers return things. Employees need rules instead of instincts. And the software almost never does what you actually need.

I built a company around solving some of that and called it GreatBuyElectronics. My childhood friend Steve put $20,000 into it so we could build a more automated buyback operation. Around 2012 I met Byron, who came to me wanting to buy seven Macs. We stayed in touch, later partnered, and GreatBuyElectronics was folded into TechGator.

It grew quickly. Overhead, debt, cash management, and the way the business was being run got ahead of it, and it stopped being sustainable. I took a buyout and left. Byron kept TechGator and SellMac. TechGator closed later on. Roughly two years after I left, Byron offered me SellMac.com back for around $5,000. I bought it, rebuilt it, and started over.

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The second run started with a much clearer idea of what mattered. That became Techable, which sells technology with a heavy focus on Apple, and SellMac, which buys devices from consumers, businesses, schools, and organizations.

Selling technology creates a problem after the sale, so SafeTech Warranty happened. Running all of it created software problems nobody was going to solve for us, so Secure365 happened. Neither one started as an idea. They started as something that was already broken.

Right now most of my attention goes to pricing at SellMac, internal systems at Techable, and figuring out where AI actually helps instead of where it demos well. I am also writing down what I wish I had understood at the start, in Operator Notes.

I do not know how all of it turns out. That is part of why I write it down.