Taming the Multiverse with Plaud
June 24, 2026
Most of my days feel like snapping between dimensions of a multiverse, and the important stuff slips. A small AI recorder called Plaud tamed the chaos.
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Field Notes
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Your IT Stack at 30, 50, and 100 Employees: What Should Already Be True
June 22, 2026
Technology debt compounds quietly. The companies that stay out of crisis are the ones who fix things on a schedule, keyed to headcount instead of the calendar. Here is what should already be true in your IT stack at 30, 50, and 100 employees, why each layer becomes mandatory when it does, and what it actually costs you to fall a stage behind.
Cyber Insurance Renewal Just Got Harder: What Underwriters Want Now
June 22, 2026
Cyber insurance used to be a form and a credit card. Now the renewal questionnaire reads like a security audit, and the wrong answers mean a denial, a premium several times higher, or a claim that does not pay. Here is what underwriters actually require now, why it changed, and how a growing company gets ready in about 90 days.
Why Microsoft 365 Business Premium Is the SMB Operating System
June 16, 2026
Most growing companies do not have an IT strategy. They have a pile of subscriptions that accumulated one emergency at a time. Microsoft 365 Business Premium replaces the pile with a platform: identity, devices, security, and collaboration in one bundle, one bill, one decision.
The True Cost of Cheap IT: What the Lowest Bid Really Costs You
June 15, 2026
You asked three providers for a quote and one came back noticeably cheaper. Here is where the lowest bid really leaks money.
When You Outgrow Your Accidental IT Person: The Signs, and What to Do About It
June 15, 2026
The person who became your IT department never trained for the job — they just wore one more hat. Around 40 or 50 people, they start drowning, and it is not their fault. Here are the signs you have outgrown a one-person IT function, and the move that fixes it without losing the person who got you here.
How Much Should IT Support Cost for a 50-Person Company?
June 15, 2026
Most growth-stage CEOs ask the wrong question. The right one is what it actually costs to supply your team with everything they need. Here is the bucket-by-bucket math for a 50-person company.
IT for Growth-Stage Companies (5 to 100 Employees): The Operating Manual
June 15, 2026
An operating manual for IT at a 5-to-100-person company: what your stack should do, when to change it, what it costs, and whether to hire or partner.
In-House IT Hire vs. Outsourced MSP: A CFO's Worksheet
May 21, 2026
Most growth-stage CEOs assume they should hire someone for IT. That instinct is wrong about 80% of the time at the 20-100 person stage. Here's the worksheet your CFO would build if you handed her the problem.
The Eight-Dollar Outage: Why Summit Doesn't Publish SLAs
May 10, 2026
Published SLAs are theater. Here's the story of the eight-dollar credit, the 27-page Kaseya template, and what Summit promises customers instead.
Your Business Is Built on an Inefficiency. AI Can See It Now.
April 8, 2026
Every business is built on an inefficiency that was too expensive or invisible to close. AI is closing those gaps on the timescale of model releases, not decades. Here's the taxonomy and three questions every leader should be asking.
Utah Cybersecurity Affirmative Defense Act: How It Protects Small Businesses After a Data Breach
March 28, 2026
Utah's Cybersecurity Affirmative Defense Act gives businesses a legal shield after a data breach, if they have a written cybersecurity program. Here's what Utah business owners need to know.