Except that McConlogue’s assertion that he can save at least one homeless person from this plight by teaching him how to code (he swears) isn’t satire.
To make a TL:DR story short: The problem with this is pure Kantian ethics: “Act so as to treat people always as ends in themselves, never as mere means.” While the intentions are obviously a lot more benevolent, McConlogue’s bet comes off as tone-deaf, like the time Paris Hilton’s boyfriend paid a homeless guy $100 to spill a soda on himself. You’re supposed to treat other humans like subjects, not objects, remember?
While he asserts that the title isn’t implying that some people are “justly” homeless, McConlogue, whose CrunchBase profile picture is a photo of him sailing, is demonstrating a profound cluelessness about poverty and the disenfranchised. In the most infinitesimally improbable chance that “The Journeyman Hacker” chooses the coding above the money and accepts the laptop, he is putting himself at risk of theft every night.
Then there’s the issue of mental illness and the myriad factors beyond self-determination that would cause someone to be homeless in the first place. Ever hear of Ronald Reagan?
“We (society) make things complicated when this is simple,” McConlogue writes in an email to me. “I can walk by him tomorrow and ignore him, or I can offer the only things I have, the ability to write software and a small amount of cash. I choose to offer, maybe its wrong, maybe it its right but some things are matters of the heart.”
Well here’s a solution: If you want to bypass the traditional, and less morally suspect, “donate to a homeless shelter” route and “take action,” why not offer both the books and the cash?
Update: “Leo,” McConlogue’s homeless friend has, in the most “infinitesimally improbable” chance, accepted the offer of coding books and a laptop versus money. And McConlogue tells me that he’s actually bought “A Modest Proposal” to read as he works with Leo. Honestly, there might be something to this on an individual level — we’ll keep you posted.