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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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hahahahaha SOC2 lol
dude’s lucky he doesn’t have to work within the narrow bounds of SOC2
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Caught myself calling 200 PB/month “small” today.
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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: vist.ly/5sc2e
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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: vist.ly/5sbs7
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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.
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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
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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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Don’t hold your breath
Now we'll finally learn what's in the Epstein files. Mike Johnson is no longer in a position to shut down the House in order to prevent votes on measures to force their release. It's time. It's past time.
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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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