We Have No Future, But We Know How to Have Fun
A due diligence trip to Toledo during the financial crisis, staying at the Ritz in Detroit, and a car rental receptionist who summed up a city — and turned out to be wrong.
My tenure at ConnectWise ran from early in the year 2000 to around 2017, when I left — but remained on in a consulting capacity beyond that. This was a particularly tumultuous time in world history, with many interesting things happening in the world, juxtaposed on top of the many interesting things happening at work.
There were always interesting technical and business challenges, alongside what, in normal times, would be a once-in-a-lifetime global event.
The mundane, next to the unprecedented. That's the way things were.
The Financial Crisis
One time that sticks out is the financial crisis. I remember reading that we were a few days from money being unavailable in ATMs, while staring out the window at a seemingly normal world. It was surreal. But also — the dotcom cloud was crashing because .NET didn't like our authentication payload.
Several months later, when the effects of the global financial crisis were in full swing, I remember absentmindedly heading over to the kitchen for my Diet Coke (as is my wont), and the CEO was sitting on the couch. I hadn't noticed him as I walked by.
"Do you have a second?"
Trapped.
Toledo, LabTech, and Detroit at Christmas
We needed to fly to Toledo to look at a small RMM company called LabTech as part of a due diligence trip. He and I would meet with the developer — in the lab — and decide whether ConnectWise would be getting into the RMM business. It was just a few days from Christmas, and I was worried whether we could get home in time.
Although we were meeting in Toledo, we stayed at the Ritz Carlton in Detroit. We were at the epicenter of the suffering in America while also at an exciting and pivotal moment in the company's history. The snowy, bleak landscape and lifeless industrial backdrop outside our hotel didn't register with me then, but it does now.
We spoke to the receptionist at the car rental counter.
"What is there to do in Detroit?"
"We have no future and we have no opportunities, but we know how to have fun."
The receptionist turned out to be incorrect about Detroit — they were going to experience a surprising revival. We bought that little RMM company. We had no flight home. And throughout the entire trip, we were experiencing a rather severe cloud outage.
A story for another day.
I am struck by the contrasts.