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October is Cybersecurity Awareness Month, and this year's theme is Don't Make It Easy for Them. Jason Russell counts down ten moves that make a small business a harder target, from locking down your Wi-Fi to the one setting Microsoft's research found cuts the risk of account compromise by more than 99%.
First, he retires a statistic you've probably seen: that 60% of small businesses close within six months of a cyberattack. Reporters found no study behind it, and the organization it's usually credited to has asked people to stop using it. What does hold up: the FBI logged more than one million internet crime complaints in 2025, with nearly $21 billion in reported losses, and Florida ranked third in the country for both.
The countdown
Chapters
Mentioned in this episode
Sources
Need help with your list?
If you couldn't check off more than a few, email Jason directly at [email protected]. Tell him which numbers you're stuck on, and he'll help you figure out where to start.
Harmony MSP provides managed IT and cybersecurity for small businesses, medical and dental practices, law firms, and accounting firms across Central Florida. harmony-msp.com
Description
Search for IT companies near you and every website makes the same four promises: proactive monitoring, fast response, security built in, and local support. Those words can't tell you which managed service provider is actually good. Evidence can.
Jason Russell founded Harmony MSP, the firm that sponsors this show, so he says up front that he has a stake in how you choose. Then he walks through the seven-step vetting process he'd want you to run on his own company. It starts with the one-page requirements list you write before any sales call and ends with the scorecard you use to pick a winner.
Along the way:
Florida listeners get three local specifics: hurricane planning, the state's 10-day breach-notice clock for IT providers, and the cybersecurity safe harbor Florida still doesn't have.
In this episode
00:00 Every IT company makes the same promises
00:43 A disclosure, and a promise
02:11 Step 1: Write down what you need before you call anyone
03:41 Step 2: Build your shortlist on fit, not ad spend
05:12 Step 3: Ask for documents, not demos
08:08 Step 4: Check references like an investigator
09:16 Step 5: Treat the sales process as a preview
09:59 Step 6: Read the contract for the exit
11:30 Step 7: Score your finalists on evidence
12:25 For Florida listeners: hurricanes, breach notice, and a myth
14:41 What vetting can't tell you
15:32 The short version, and how to reach us
Key takeaways
Resources
Sources referenced in this episode
Want a second set of eyes?
If you have IT proposals on your desk and want someone to go through them with you, call (407) 720-6540 or email Jason directly at [email protected].
About the host
Jason Russell is the founder and CEO of Harmony MSP, a managed IT and cybersecurity firm in Lake Mary, Florida. A former Navy cryptologic technician and NSA network security consultant, he's spent more than two decades translating security problems into decisions business owners can actually act on. He's the author of Secured: The Cybersecurity Survival Guide.
Sponsor
Ctrl+Alt+Protect is brought to you by Harmony MSP: managed IT, network security, and compliance for small businesses, law firms, medical and dental practices, and accounting firms across Central Florida. https://harmony-msp.com
Tags
managed service provider, MSP, how to choose an IT company, how to vet an MSP, managed IT services, IT support contract, service level agreement, SLA, third-party risk, vendor risk, cyber insurance, HIPAA business associate agreement, FTC Safeguards Rule, Florida Information Protection Act, hurricane preparedness, small business cybersecurity, Orlando IT support, Central Florida, Ctrl+Alt+Protect
Without any special tools and without breaking into anything, a stranger can send an email that appears to come from your business. Your domain in the From line. A short, reasonable request: pay this invoice, or update the account we send payments to. Your client opens it, because why wouldn't they.
In this episode, Jason Russell walks through why email was built this way, and the three DNS records that make spoofing much harder to pull off: SPF, the list of servers allowed to send for your domain; DKIM, the tamper-proof signature on every message; and DMARC, the rule that ties them together and tells receiving servers what to do when something fails.
Then the part most businesses miss. DMARC has three policy settings, and the most common mistake is stopping at the first one. A domain sitting at p=none gets you reports about being spoofed — not protection from it. CISA treats that setting as a temporary step toward reject, not a finish line.
The episode closes with what these records genuinely cannot stop: lookalike domains and display-name spoofing, both of which show up constantly in wire fraud aimed at law firms and title companies. Records handle the easy version of the attack. A verification habit handles the rest.
You'll finish this one knowing exactly what to ask your IT provider, and how to tell whether the answer you get is a real answer.
In this episode
Key takeaways
Resources
Your cyber insurance renewal questionnaire got longer this year, and it isn't because you did something wrong. It's because carriers paid out on a run of very expensive claims and started asking sharper questions.
Here's what most business owners don't realize: that application is a warranty document. Every box you check is a legal promise about how your business actually operates. If a forensic investigation after a claim finds your environment didn't match what you wrote down, the carrier can rescind the policy, which means your claim is denied and prior payouts can be clawed back. Some courts have held that the carrier doesn't even have to prove the misrepresentation caused the loss.
In this episode, Jason Russell walks through the three incidents that rewrote the modern cyber insurance application, what underwriters are really asking in each section, and how to answer accurately when you know you have a gap.
You'll learn:
The short version: an honest application with a couple of gaps and a plan is a policy that will still be there when you need it. A perfect-looking application that doesn't match your network is an expensive piece of paper.
Most small business owners didn't sign up to run security for their company. They signed up to practice dentistry, represent clients, file returns, or build something. The technology came with the job — and so did the risk.
Ctrl+Alt+Protect is a show for those owners and the people who keep their offices running.
Host Jason Russell spent more than eight years in the U.S. Navy as a cryptologic technician, running shipboard networks and encrypted communications during tactical operations. He went on to work at the National Security Agency as a network security consultant, then spent four years in Iraq leading the Multi-National Division–Baghdad Tactical Biometrics Cell and a team of forty field support engineers. In 2011 he brought that work home to Central Florida and founded what is now Harmony MSP, where he works with small businesses, medical and dental practices, law firms, and accounting firms.
In this trailer, Jason lays out what the show covers and how: one topic per episode, explained plainly. Why the email from your bookkeeper might not be from your bookkeeper. What a cyber insurance application is actually asking you to certify. Which items on a vendor's proposal matter, and which you can pass on.
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