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After 20+ years in IT, I’ve learned this:
The most expensive mistakes aren’t picking the wrong tool - they’re signing the wrong contract, trusting the wrong vendor, or skipping the hard questions because everyone’s in a hurry.
I share what I’ve seen go wrong so others don’t have to learn the hard way.
Gangsta move by @sama right there
Some news: I’m joining OpenAI to lead product management for Core Products!
I have a lot of respect for OpenAI for showing the world that scaling works, for bringing AI to over a billion people, and for believing great products are core to the mission.
I’m excited to work with @thsottiaux, an incredible PM team, and everyone across OpenAI. Together, we’ll build agents that have your back and your team’s, and keep you in control, so you get more time for the people and work you love.
Lots to learn, and lots to build. Please keep your feedback coming!
When I had an HOA my neighbors were suddenly experts at architecture, construction, design, building codes, law, physics, etc…
This is the same (but worse) phenomenon with any disaster and the internet, plenty of voices that think they are experts but have no clue what they’re talking about
An SLA credit is a percent of your monthly bill. It has nothing to do with what the outage cost you.
If a circuit keeps failing, the credit won't get you out. A chronic outage clause will. Ask for one before you sign: vist.ly/5rd7a
A company priced immutable backup storage before checking what the rule actually required.
Once they checked, the projected five year cost dropped by about $1.5M.
Here's what to verify before buying: vist.ly/5rbvb
I've seen VMware buyers spend so long evaluating alternatives that they run out of time to leave.
More research doesn't move the renewal date.
Here's what to figure out before then: vist.ly/5r6nt
You're not deciding which FinOps platform to buy. You're deciding whether the person accountable for your cloud bill has the authority to change it. Six checks tell you which problem you actually have. vist.ly/5r3rh
Wow, Brad just gave each of our kids $100 just with a QR code!
This gift will be worth $8k for each of them when they hit retirement age
Good people are in the world, don’t believe what you read in the news
Happy Halloween! Hit me in replies with your kid’s 530A @TrumpAccounts QR code for an investment treat. Download your kids 530A account now - it’s already open w $$ - just download the app to claim it! Get them invested for a lifetime of financial freedom! 🧡👻🇺🇸
We’ve moved our sites off Webflow to Astro this year. So worth it.
We moved 40 WordPress sites to Astro. They now run on Cloudflare Workers for free.
It took us 2-3 months. Before that we paid for Hetzner servers plus Plesk to keep them alive. Updates, plugins, security patches, the usual WordPress tax.
What we did:
1. Pulled the content out of WordPress
2. Rebuilt each site in Astro, static pages, no plugins
3. Deployed to Cloudflare Workers
4. Switched DNS site by site and checked each one live
5. Backed everything up, then cancelled Hetzner and Plesk
Result: around $90 a month saved and the sites are faster and all we can control with AI agents team
Still running WordPress for clients in 2026?
People download and use Ubuntu for free
What obligations exist in this relationship?
This is why open source maintainers burn out, they owe us nothing when everything is expected from them
So @Ubuntu still hasn't patched this open hole on any Ubuntu server on the public internet that lets anyone take it over
We might just have to switch all our servers over to Debian in this new post-AGI time of rapid cybersecurity hacks which require just as rapid patching
Slowpokes will be left behind
chalmovsky.com/posts/wtf-ubu…
One of the big US carriers listed 10 Gig dedicated internet at $9,375/mo in 2016. Today it’s $3,000. If you signed in 2023 you’re paying $4,499 against a $3,000 rate card. Your contract didn’t get the memo.
Ten years of this carrier’s internet and private line pricing, what changed, and what to check before you renew: vist.ly/5qzf9
We’re entering the era where patching is no longer the red headed step child but will be a priority for infosec programs
Also the demands will be evaluating and deploying patches in hours not days/weeks
Log4j is going to feel like a a dream soon
What a disaster atlasum.net/blog/cve-2026-98…
Too bad Google invented transformers and then put them on a shelf
Just like Kodak and Xerox you can either disrupt yourself, or you can give someone else the opportunity
The question now is does Google lean in or are we in a Yahoo spiral?
I'd gladly give up another 5% discount for a provider that can actually support my business.
If you've got users across ten states, having someone who can show up and fix things matters more than a few points off the quote.
Here's what to check before choosing: vist.ly/5qnjd
Microsoft patched 1,400+ vulnerabilities this month - one of them was already being used in attacks.
Say your MSP report shows 98% patched within 14 days. That number won’t tell you if the one being exploited is fixed on your machines. And if your contract only asks for a patch percentage, that’s all the MSP owes you.
Before you renew, the agreement should say who handles actively exploited vulnerabilities and how fast. If it doesn’t, fix that first.
We review MSP agreements before renewal and help you compare providers if it’s time to switch: vist.ly/5qmd5
Your provider can keep missing its uptime commitments and still hold you to the full contract. All you may get for the outages is a credit on your next bill.
If the service keeps failing, can you leave without paying to terminate?
That's the clause I'd check before signing or renewing. Have an agreement on your desk? Let's review what your exit terms actually allow: vist.ly/5qini
Three vendor quotes won't help much if you asked the wrong three vendors.
Before comparing prices, figure out who belongs on the shortlist and what you're actually comparing.
Here's what to check first: vist.ly/5qhhm
It's the lack of judgement up and down the stack that shows the rot, unfortunately the only fix is to root it out and start over
Siri is still bad, like really really bad. I opened an email with my Uber Eats confirmation, there was a live activity on the screen with progress, and I pulled down and asked Siri "what did I order for lunch?" And it thought for like 2 minutes and then said it doesn't know. 🤦♂️
Okay so the harness and models are clearly bad. Well, then next I opened up the Siri GUI app on macOS and HOLY. It's the worst looking, beginner, basic bitch app I've ever seen. Did someone spend more than 5 minutes on this?
Whoever worked on this app along with the full chain of people who checked off on this needs to be terminated immediately. This is 0/10 terrible software, so embarrassed for Apple to ship this.













