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.

Law firm cybersecurity requirements: The Eight Security Questions on Your Renewal Application

There is a moment that happens in a lot of law firms around renewal time. The cyber insurance...

Right-sized security healthcare: HIPAA scales to your practice

Every few months a medical practice calls us after getting a quote from another technology company....

Trade Secrets Are Walking Into Free AI Tools. You Just Can’t See It.

A well-meaning engineer pastes a proprietary design into a free chatbot to troubleshoot it. An...

The SEC Is Now Asking How You Govern AI. Most Firms Can’t Answer.

On November 17, 2025, the SEC’s Division of Examinations released its priorities for the year. For...

Your Staff Is Already Using AI With Patient Data.

I’m going to tell you something most practice owners don’t want to hear: your staff is already...

Your Staff Is Already Using AI With Privileged Client Files.

I’m going to tell you something most managing partners don’t want to hear: your associates and...

Intuit Doesn't Back Up Your QuickBooks.

If you run your business on QuickBooks Online, there’s one question you should be able to answer in...

What Your IT Invoice Is Hiding, And What It's Actually Costing You

I want you to do something right now. Pull up last month's IT invoice and try to explain every line...

How Markups & Equipment Rentals Keep You Paying, and Keep You Stuck

Here's a question I ask every prospect we sit down with: do you own your firewall?

File Storage issues: Your Crew Can’t Access the File. Again.

How construction companies are solving the job site connectivity problem without expensive custom...