Smarter tech decisions start here.
Last spring, during what was supposed to be a routine review of cybersecurity for small business clients on my roster, I sat in a back office with the owner of a twelve person accounting firm while she read an email out loud. At first glance, it looked like it came from one of her longtime…
The first cloud invoice I ever audited for a client ran 41 pages. Before our meeting, the finance director had printed it, highlighted every line she did not understand, and slid it across a conference table with a look that said, “Tell me this is normal.” In fact, most of the pages were yellow, and…
I have spent most of my career on the receiving end of the phone call that starts with “the internet is down and nobody can work.” Sometimes it was the router. Once it was a cleaning crew that unplugged a switch to run a vacuum. More than once it was a business owner who had…
If you’re planning a web application development project, the first question on your mind is probably “how long will this take?” Nearly every new client asks me that, and my honest answer is always the same: I can’t tell you yet. I know how frustrating that sounds when you have a budget meeting on Friday…
How much does a penetration test cost? In 2026, penetration testing cost usually runs $10,000 to $35,000 for a standard engagement, and almost every scoping call I take starts with that exact question. First, someone from finance or IT asks for “a ballpark.” Then I ask what they want tested, and there’s a pause. In…
Every few weeks, someone forwards me a proposal for managed security services with a version of the same question attached: what am I actually paying for? Usually, the quote has a tidy monthly number at the bottom, a page of acronyms above it, and almost nothing explaining how one connects to the other. For context,…
Every few weeks someone asks me about AWS vs Azure over coffee, usually a founder, a managing partner, or an operations lead who has been handed the cloud budget and has no idea where to start. The question is always some version of “which one should we pick?” and Google Cloud gets mentioned almost as…
The call that starts most cloud migration strategy conversations usually comes on a Friday afternoon. First, the air conditioning in the server closet fails again. Then someone notices the nightly backup job has not finished cleanly in over a week. On top of that, the one person who really understood the ERP database left the…
When it comes to choosing a managed service provider, I have sat on both sides of the table. Early in my career I worked inside one, writing proposals and promising response times I privately hoped we could hit. Later I became the person reading those proposals as a CIO, and today I do the same…
I have sat on both sides of this table. Early in my career, I built internal IT departments, and I once grew a single overworked admin into a team of twelve. For the last several years, however, I have worked as a fractional CTO for companies with 20 to 300 employees. One of the most…