Let’s get something out of the way: cybersecurity isn’t just an IT problem. It’s a business risk. A financial one. A reputational one. And for many business owners—especially those focused on growth or gearing up for retirement—it’s an overlooked one.

We’ve seen clients with beautifully structured succession plans, thoughtful estate documents, and top-tier investment portfolios. But when we ask about cybersecurity, we get the same reaction we’d expect if we asked about alien abduction insurance: a confused chuckle, followed by, “We’ve got antivirus software. We’re fine.”

But are you?

Here’s the thing—many business owners are misjudging the true scope of cyber risk. And that misunderstanding can cost them a lot more than a few bad passwords.

False Sense of Security: “We’re Too Small to Be Targeted”

This is the most common myth out there—and one of the most dangerous.

Many small and midsize businesses think hackers are only after the big fish: Amazon, Bank of America, or the U.S. Department of Defense. The reality? Small businesses are the low-hanging fruit. Easier to breach. Less likely to have strong defenses. And often connected to larger supply chains—making them valuable targets in a broader attack.

According to a recent Verizon Data Breach Investigations Report, nearly half of all data breaches involve small businesses. Why? Because many don’t have a formal cybersecurity plan, let alone employee training or updated software.

So if you’re running a business with 20 employees and think you’re flying under the radar—think again. You’re not invisible. You’re vulnerable.

Relying on IT Providers to “Handle It”

Outsourcing your IT support is smart. But mistaking your managed service provider (MSP) for a cybersecurity firm? That’s risky.

Most MSPs focus on keeping your systems running—installing updates, managing backups, troubleshooting printers (because there’s always a printer issue somewhere). But cyber risk management? That’s a different skill set. Unless you’ve hired a firm with explicit cybersecurity expertise, odds are no one’s actively testing your defenses, monitoring for breaches, or running incident simulations.

You wouldn’t hire a bookkeeper and assume they’re filing your taxes, right? So don’t assume your IT help desk is handling cyber liability either.

Underestimating the Financial Fallout

When business owners think about a cyberattack, they often picture a temporary inconvenience. A few hours of downtime. Maybe a ransom payment. But the reality is often more brutal—and longer-lasting.

Here’s what a serious breach can bring to your doorstep:

• Legal fees and settlements if client or employee data is compromised
• Regulatory fines—especially if you’re in a sector like finance, healthcare, or education
• Business interruption that stalls operations for days or weeks
• Loss of client trust (which may take years to rebuild, if at all)
• Ransomware demands, which many cyber insurance policies now limit or exclude
• Cost of forensic investigation, system rebuilds, and credit monitoring services

Even a “moderate” incident can cost six figures. For business owners nearing a liquidity event, that could knock a major dent into your retirement plans. Worse still? A breach discovered during due diligence could reduce your business valuation—or even kill the deal entirely.

The Hidden Risks of Personal-Professional Overlap

One thing we see all the time: business owners using personal devices for work, or worse, using business email accounts for personal banking, social media, or online shopping.

That’s not just messy—it’s dangerous.

Mixing personal and professional accounts creates a web of exposure. If your kid’s Roblox account gets phished, and that same password is tied to your payroll system, well… you see where this is going.

Cybercriminals are patient. They’ll sit quietly in your inbox, watching your email patterns, waiting for the perfect moment to spoof a vendor or intercept a wire transfer. And they don’t care if you were just trying to order sneakers during your lunch break.

Cyber Insurance Isn’t a Silver Bullet

It’s tempting to think you can just buy a policy and be done with it. But cyber insurance is not plug-and-play—and it’s getting trickier by the day.

Many policies come with exclusions longer than the coverage section. If you haven’t done the “right” things—like employee training, endpoint protection, regular backups, or incident response planning—you might find your claim denied. Insurers are tightening underwriting standards, and some require annual risk assessments just to qualify for coverage.

Translation: Cyber insurance is one piece of a much bigger puzzle, not a get-out-of-jail-free card.

What You Should Be Doing (But Probably Aren’t)

So what does a more cyber-aware business owner look like? No, they’re not holed up in a server room surrounded by blinking lights. They’re just treating cyber risk the same way they treat tax risk, liability risk, or succession risk: as a critical part of the planning process.

Here’s what that looks like in practice:

• Conducting an annual cybersecurity risk assessment—ideally through a third-party expert
• Segregating financial systems and client data from regular business operations
• Establishing role-based access so not every employee has admin rights
• Creating a formal incident response plan, with clear steps for communication and recovery
• Training staff (yes, even the CFO) on phishing and social engineering attacks
• Using multifactor authentication on everything, especially email and financial apps
• Backing up systems regularly, and verifying that those backups actually work
• Revisiting your cyber insurance coverage, exclusions, and requirements every year

No one expects perfection. But preparedness? That’s becoming table stakes.

Why This Matters Now—Not “Later”

We get it. You’re busy. You’ve got a team to run, a pipeline to fill, and if we’re being honest, cybersecurity doesn’t exactly feel like it adds to the bottom line. But ignoring it doesn’t just risk losing money—it risks undermining everything you’ve built.

Especially if you’re in a transition phase—getting ready to sell, step back, or pass the reins to a family member—cyber risk becomes a multiplier. It can inflate legal complexity, damage goodwill, and knock zeroes off the value you’ve spent decades building.

We’ve seen owners who did everything “right” financially, only to have a breach delay their exit—or force them to stay in the business longer to recoup losses. Cybersecurity may not feel like a financial planning issue. But once something happens, it quickly becomes one.

The Bottom Line: Cyber Risk Is Financial Risk

If you’re a business owner and you haven’t had a real conversation about cyber risk—with your advisor, your insurer, or a cybersecurity expert—it’s time.

At Suttle Crossland, we help our clients see the full picture. That means not just managing investments or crafting tax strategies, but ensuring the risks they don’t see don’t come back to bite them.

Because building wealth is only part of the story. Protecting it—that’s where the real work begins.

Want to talk about how cyber risk fits into your bigger financial picture?
Let’s schedule a conversation. No sales pitch. Just honest advice on how to protect what you’ve worked so hard to build.