At the core of the Basecamp kerfuffle, it’s a disagreement at work around a tense subject. I’ve seen this play out many times before and after reading all the accounts from all sides it boils down to an executive unwilling to take the L.
Tense discussions happen from time to time at work, it’s part of life. But when an employee questions a statement or a joke or even an apology by an exec, what happens next speaks volumes.
employees brought up the list of funny names and 10yrs later, it’s not fun and a little mean and racist. I will credit DHH for the response he wrote acknowledging it was bad and why it’s gone but in the ensuing discussion someone points out how name calling leads to worse things.
It’s an interesting point but maybe it was a step too far deep in a tense discussion that started with a full fledged apology. I think the person posting it wanted to make sure DHH knew why the list was wrong but he felt like he already said it was wrong.

But here’s the crux:
Even when you’re the CTO and you’re eating crow by apologizing to staff, if one response is you didn’t do enough, TAKE THE LOSS and be quiet and think over why this person didn’t think you got it. DON’T GET DEFENSIVE. Repeat: don’t get defensive.
There’s a tendency to always have the last word in an argument that is also working here.

In my mind, this whole basecamp thing hinges on DHH flipping out after seeing “genocide” on a graphic when he could have said “harsh! but fair, we won’t do these things going forward”
I’ve seen far too many execs refuse to take the L and apologize or step back in the heat of the moment and so many seemingly small things blew up into giant problems because in a thread of 50 comments an exec couldn’t ignore one thing they saw as a jab or barb or dunk on them.
An exec should take the high road, do big picture stuff & protect employees.

But DHH didn’t deescalate, he dug through years of chat logs to repost a hypocritical gotcha from the person who posted criticism which is remarkably petty! DHH’s gotta win every argument at all costs!
There's a path to redemption but it would be tough. DHH could acknowledge he flipped out, they could admit "no politics at work" is ridiculous (and impossible to avoid when making big choices in software design) and try to rebuild from there.

But instead they'll triple down.
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