When I was running my company, I recall being vaguely terrified at the prospect of falling victim to a cyber attack. Not only did the threat seem more likely with each year that passed, but it also felt like its potential impact grew as we acquired more customers, hired new employees, and put more of our internal systems online. Today, in 2026, you probably don’t need to look terribly far to read about both the frequency and seriousness of cyber attacks on both individuals and small businesses. As a result, this week's episode is dedicated entirely to exploring the basic building blocks that small businesses need to have in place to protect themselves. To help me, I was joined by Kip Boyle, a security expert with 25 years of experience in cybersecurity and IT risk management for organizations in insurance, financial services, technology, military, and logistics, among others. In our discussion today, among many other topics, we cover: (1) The most common cyber vulnerabilities for small businesses (2) The “minimum viable” cybersecurity stack for a small business (3) How to build out these types of internal capabilities if you don’t have IT leadership (or even an IT employee) (4) When outsourcing to a separate company is a good idea and when it isn’t (5) Whether the growth of AI tools is a net positive or a net negative for small business cybersecurity (6) The role that cyber insurance should play in an overall protection plan (7) What to do if your systems are breached (8) The role that these considerations should play in a due diligence process ...and much, much more