Dylan Borden

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.

AI in Construction: 84% Use It, Only 8% See Real Value.

AI in construction is now common, but most firms are not getting much from it yet. Two recent stories explain why, and what the firms that are getting value have in common. The short version: AI pays when it lives inside the systems your crews and PMs already use, not in a separate browser tab.

PHP2Shell Vulnerability: What Your Business Needs to Do This Week

Last updated: October 22, 2026. This is a fast-moving story. We will update this post as new...

Best Managed IT Providers in Southwest Florida Compared

Written by Four Winds IT, a Sarasota-based managed IT provider serving Southwest Florida since...

HIPAA cloud storage: Your EHR Is in the Cloud. Almost Nothing Else Is.

Ask a practice manager whether they are in the cloud and the answer comes back fast. Yes. The EHR...

Your Law Firm's Server Is a $35,000 Decision Nobody Has Made Yet

Nobody at your firm thinks about the server. That is sort of the point of it. It sits in a closet...

Microsoft Copilot for Small Business: Costs, Licenses and Rollout

Microsoft Copilot is Microsoft's AI assistant for work. Every Microsoft 365 business plan already...

Your Team Is Already Using AI. 3 Rules That Keep It From Costing You.

What a room of 80 Gulf Coast business owners taught us about the gap between how fast AI arrived...

Most of What Gets Sold to Manufacturers as Security Does Not Protect a Single Production Hour

Ask a plant manager what keeps them up at night and you will not hear about data breaches. You will...

Your Custodian, Your Clients, and the IRS Are Not Asking the Same Question

"Financial services" is not one industry, and treating it as one is why most security advice aimed...

Four Winds IT Acquires Suncoast IT Consultants, Expanding IT Support in Venice & Wellen Park

Four Winds IT has acquired Suncoast IT Consultants, LLC, expanding its reach among small and...