Jake Schaaf

20+ years running an MSP in Ohio. Just started a fractional PE advisory practice. Just started a third firm building AEO-first websites. Three companies, three different stages, one operator. Follow for what launching looks like in real time.

If you're an owner-operator, fractional executive, or working with PE-backed companies, you'll find something useful here. If you're not, you're welcome too. Tiffin, Ohio. Reach me here or at jakeschaaf.com.

And occasionally: → How I lost 35 lbs walking, eating better, cutting alcohol and caffeine → Why staying in shape matters at 49 with two daughters and three companies to build Both lanes serve the same audience: people who build things.

20+ years running an MSP in Ohio. Just started a fractional PE advisory practice. Just started a third firm building AEO-first websites. Three companies, three different stages, one operator. Follow for what launching looks like in real time.

Your verbal agreements are time bombs open.substack.com/pub/jakeschaaf…

I wrote a 4-paragraph price increase email once. Explained my overhead. My rent. My costs. Client called 5 minutes later. Talked me down to 3%. Left $4,000 on the table that year. The entire email should be two sentences. Wrote about it here: jakeschaaf.substack.com/p/raising-your…

RAISING YOUR PRICES open.substack.com/pub/jakeschaaf…

Policy beats emotion every time. Full breakdown: jakeschaaf.substack.com/p/fire-your-wo…

That's the shift that matters. You set the standard when you were thinking clearly. When the third strike hits, you're not emotional about it. You're following the rules you wrote for yourself.

Most owners know which client has to go. They've known for months. The problem isn't the client. It's that the firing feels like a personal failure, so they stall.

This week's issue of The Next Call has the math, the story from 2019 that cost me more than I saved, and the exact script to use. Free. No fluff. jakeschaaf.substack.com/p/fire-your-wo…

You are filling your capacity with gravel and leaving no room for gold. The fix is not a price increase. Not a scope renegotiation. Not waiting for them to leave. Fire them.

ou look at a client paying $4K/month and think you can't afford to lose them. You can't afford to keep them.

Fire your worst client today open.substack.com/pub/jakeschaaf…

wtf… Google just shipped a CLI agent that runs Gemini 2.5 locally No browser. No API key. No bill. Just you and AI in the terminal. Here’s everything you need to know 👇

Picture this: It’s Monday morning, and you’re ready to take on the week. You fire up your computer, log in to your systems… and… nothing works. Emails won’t send. Your website is down. Your team can’t access files. Customers can’t place orders. 😱 Panic sets in. You call I

You’ve seen these, right? Those (slightly annoying) little puzzles that make you click all the traffic lights or bicycles or bridges. Or you must type out wobbly letters to “prove you’re not a robot”. They’re called CAPTCHAs, and they exist to stop bots from spamming websites, l

Does your business rely on Microsoft’s Remote Desktop app to connect to PCs or virtual desktops? Listen up… 👂 There’s an important change coming. This month – from May 27 – the Remote Desktop app will no longer be supported by Microsoft. This is the app that’s downloadable