Similarly, DHH isn't writing "don't sell your business if you burn out". If you burn out and you can't fix it, do right by your team. DHH is critiquing the notion that you should build to flip, and the notion that there's great honor in doing that repeatedly. It's undeniable that there is a mythology around "serial entrepeneurs" who repeatedly flip companies.
You know what would be incredibly boring? A DHH post that anticipated and acknowledged every special case and every objection. "What if someone offered you $1Tn" is an especially b o r i n g objection. One of the reasons people read DHH's articles and don't read ours is that we write things like "Of course, if someone offers you $100MM, you should blah blah b l a h b l a h", and he doesn't.
It is also OK for him to be wrong. Being wrong --- at least, when you're not writing about password hashing --- does not put a point on your blogging license. The bar is, "is it interesting and does it come from an honest place".