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.
A healthcare company priced three ways forward on VMware over 5 years, with numbers from 11:11 Systems on Signed. The cheapest was keeping VMware hosted, not leaving it. Price yours before you assume a migration saves money: https://t.co/h1OgTcpIZy
Someone told me he was ripping out all his Cisco gear for Juniper because he didn't like Cisco. Not liking a vendor is a bad reason to put a team through a migration. Here's how to decide whether to replace, fix or wait: https://t.co/SnZSmjAW7C
An AI summary can look right and still be wrong. Before your team acts on it, who actually checks it? "Human review" isn't much of a control if nobody owns it.
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: https://t.co/Rn2NsNDxcg
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: https://t.co/GTR7O6QgWu
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.
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: https://t.co/jB9bKPfIax
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.
https://t.co/IkKrP459Uk
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: https://t.co/lJ0XxxnHZm
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.
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.
https://t.co/4VbbA0stWi
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: https://t.co/Fi9l0nXdax