Buyers aren’t just buying your EBITDA. They’re buying your risk profile, and IT is a huge part of what makes a deal feel safe or scary. I sit down with Matt Kinsey of IT Fusion to unpack how IT readiness impacts valuation, deal multiples, and transaction certainty in the lower middle market, especially for businesses in the $2M to $20M range. If you’ve ever assumed “we’re too small to be a target,” this conversation will change how you see diligence.

We dig into the IT due diligence surprises that spook buyers fast: weak access controls, missing multi-factor authentication, undocumented patching, untested backups, and the bigger issue behind all of it, a lack of repeatable process. Matt explains why mature IT practices make your numbers more believable and your operations easier to replicate, which is exactly what buyers want after closing. We also talk about hidden cyber risk, including the uncomfortable reality that attackers can sit inside a network for a long time before triggering a breach, leading to holdbacks, retrades, or even a buyer walking away.

From there, we get practical. Matt shares what a deal-ready environment looks like, how to prioritize in the last 90 days before going to market, and why a third-party IT readiness assessment can uncover quick wins that don’t require massive spend. We cover key compliance and regulatory exposure, including HIPAA, PCI compliance, FTC Safeguards, and Florida privacy requirements, plus why frameworks like NIST can show “reasonable” cybersecurity governance. We close with post-integration pitfalls like messy data integrity and missing admin access that can derail timelines and budgets if they’re not cleaned up early.

If you found this useful, subscribe, share it with a fellow owner or advisor, and leave a review so more sellers can avoid preventable IT and cybersecurity risks before a transaction.