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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.
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Someone wants to replace a platform that's working because they like another vendor better. That's not a business case. Here's what to ask before you fund the switch: vist.ly/5s6g2
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Still waiting for @meow to launch a GL
QuickBooks is the enemy of small business owners.
So I built LazyBooks. Connect your bank and it does the work for you.
$19/mo. QuickBooks is $38/mo and you still do the work yourself.
First 60 days is free - price is locked if you join during launch: lazybooks.com
Lawyers advise decision makers, if you leave them unchecked they'll come up with all sorts of things that kill deals
Get the decision makers (who can sign) on a call with the lawyers present, have the lawyer explain their concern to the decision maker
It's amazing how many things just aren't that important at the end of the day
Ooh, story time!
Our first fundraise, investor used Goodwin and we used NVCA docs as the starting point, of course.
Second fundraise, new investor also used Goodwin. Same partner, different associates.
Associates called a meeting to discuss some IP sections the previous Goodwin associates had negotiated, and seeing where this was going, I joined the call and said:
"Man, it's so great working with your team on this again! Since you guys negotiated this section in the previous fundraise, it's going to go so much more smoothly this time."
What would have been an infuriating hour long call was over in ten minutes with no further redlines.
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Sign a 3 year cloud commitment and you promise AWS your spend. AWS promises a discount. Servers aren't part of the deal, and AWS just reported a $578B backlog it can't build capacity fast enough to serve. See what your commitment costs if usage drops: vist.ly/5r29a
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If your internet renewal is coming up, send me the quote before you sign it. I’ll tell you if the price holds up and what the renewal clause actually commits you to. No pitch. No prep. Just answers.
vist.ly/5rpgy
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I'll bet you can't run a test restore without finding something that doesn't work the way you expected.
Better to find out now than during an outage.
Here's what to check: vist.ly/5rndw
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One step closer to never opening QuickBooks or quicken again
Introducing Personal Finance in Claude, in beta in the US.
Connect the accounts you choose, and Claude answers your money questions in everyday language, from your own balances and transactions. Access is read-only, and Claude can't move, manage, or invest your money.
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Google Cloud lost a London zone for 6 hours on Oct 20. Workloads moved to the other 2 zones, and those zones ran out of compute.
Quota is permission to launch servers. It isn't proof the servers exist. Test failover with a zone down.
vist.ly/5rjay
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If your VMware host lost its authorization, your servers may keep running while your contract moves to another provider.
Do you know who would take it over?
Here's what to ask: vist.ly/5rh39
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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!
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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
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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
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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
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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
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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
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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?
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