Watching the Detectives

As what some would call a “serial entrepreneur,” I have a soft spot in my heart for small businesses and those fledglings just leaving the nest. Armed with great ideas or better approaches, it’s an exciting time, and I get to take a hit of some of that new venture vibe.

Often I come in at the 2nd or 3rd stage, where they’ve hired previous technology dudes (I can’t call them professionals) who maybe had good intentions and got overwhelmed by the frantic pace. Or maybe they knew how to do things in the pre-2015 world of LANs, Datacenters full of servers, etc. and didn’t know how to cope with the Cloud and especially not with remote work/work from home. Maybe they’re guys who know how to build a PC and think therefore they know proper network architecture approaches. They don’t.

Sometimes they’re hired but have a secret wish to test a theory or approach, using this poor entrepreneur as a guinea pig. Eventually the truth is revealed and the experimenter is escorted out the door. One of the parties is sadder but wiser.

As usual I’ll not mention names, but I do have cautionary tales. The common thread is that I come in and before I can make things better, I have to become a Detective. Or maybe like a Prosecutor, where I ask for “permission to treat the witness as hostile.”

Everyone thinks their house is in order. But once I start asking for receipts and documentation…

“Who configured your domain? Do you have the login credentials?”

“You have HOW MANY domains? And HOW MANY domain hosting providers?”

“I see you have Microsoft 365, but when I try to get in to Admin, it points to a GoDaddy account that doesn’t seem to exist.”

“You seem to have an array of different apps that you use for business that you don’t pay for. Are you worried about that, or are you having trouble finding mission-critical information quickly across all these platforms?”

They fold like a cheap suit.

I always try to leave good documentation, at the ready, so someone else can come in and understand where things are. One of my proudest moments was helping a remote sales staffer configure his systems in a pinch when the corporate tech couldn’t make it. When the roaming professional finally made it to town, he said something like “Clearly, your friend knows what he’s doing. Everything is set up perfectly.” It’s not hard when you stick to a professional code.

I have one case (“Yeah, Sam Spade…what’s it to you?”) that I’ve been working on since March, interrogating staff, finding a veritable Who’s Who of local tech talent has touched this organization over the years. Some of whom should know better, and others I’ve been cleaning up after for years. Hacks, who somehow keep plugging away.

When no one seems to have the domain credentials except the guy who got fired months ago, I’ve learned methods to streamline working with Risk Management departments, to say the right things to convince them that “Yes, that domain does actually belong to us rather than the scumbag we were paying hourly who used his PERSONAL email to register it.” Or professional words to that effect.

No matter. By the time I’ve unearthed all the credentials or got them out of the cloud vault, I’ve learned a great deal about their organization, and the flow of information through it. I have learned what’s working, and what’s not, and can suggest alternatives or new approaches. For me then, the fun really starts. The stuff that dreams are made on.

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