Dylan Borden is VP of Operations at Four Winds IT, a Sarasota-based technology partner serving 300+ businesses across Southwest Florida. He writes about the things most IT providers would rather not explain: what's buried in your IT invoice, whether your security would hold up to a cyber insurance claim, and how to put AI to work without creating a data problem. Dylan chairs the Sarasota AI Business Lab with the Sarasota Chamber of Commerce and led the AI in Construction Series for the GCBX Education Committee. Reach Dylan directly at (941) 315-2380 or dmborden@fourwindsit.com. Dylan lives in Lakewood Ranch with his wife, their two boys, Archie and Atticus, a dog, and two cats. When he's not juggling work and family, he's a rabid Philadelphia sports fan and a disc golf champion.
Written by Four Winds IT, a Sarasota-based managed IT provider serving Southwest Florida since 2014. We're one of the providers on this list, so we've stuck to facts each company publishes about itself and linked to the source. We support 300+ businesses across the Gulf Coast, so we know this market from the inside. This guide covers what to look for in a local MSP and compares real providers you'll find between Tampa Bay and Naples.
Ask a practice manager whether they are in the cloud and the answer comes back fast. Yes. The EHR...
Nobody at your firm thinks about the server. That is sort of the point of it. It sits in a closet...
Microsoft Copilot is Microsoft's AI assistant for work. Every Microsoft 365 business plan already...
What a room of 80 Gulf Coast business owners taught us about the gap between how fast AI arrived...
Ask a plant manager what keeps them up at night and you will not hear about data breaches. You will...
"Financial services" is not one industry, and treating it as one is why most security advice aimed...
There is a moment that happens in a lot of law firms around renewal time. The cyber insurance...
Every few months a medical practice calls us after getting a quote from another technology company....
