I feel like this comment and the article itself together in context have kind of a sour taste for me.
Just the fact that it takes such a great effort to experience first-hand how poorer people just help each other out because nobody has money, so they help. But for a tech bro to do that they have to engage in a self-indulgent hobby and cosplay as poor like they're on Undercover Boss.
Ironically this effort to relate to other real live humans with normal incomes is only possible by indulging in the ultimate luxury, which is taking major time off of work rather than being stuck working a shit job.
This is all done with a straight face while jamming a sentence full of words like "paraglider" and "packrafting."
This whole subject is all so stereotypical tech bro in such an unappealing way.
Maybe this sounds unnecessarily bitter, but I think a valid alternate take on this is that privileged people are taking advantage of the kindness of others to get a bunch of help they don't need to help them achieve a goal that is a frivolous luxury. It's great we all get to feel warm fuzzy gratitude but it seems like the NPCs in this main character syndrome story are the people inconvenienced by the OP.
Example: asking the fire department for a place to sleep, they probably feel bad so they let OP sleep in the fire department. But as a tech startup founder and software engineer, OP could have almost certainly afforded a basic motel each night with minimal to zero planning and effort and not resorted to inconveniencing other people.
It feels a little bit like your CEO going to the food bank doesn't it? The median firefighter earns under $60k and dude who has probably outearns that salary in passive investment income is asking for a place to crash. I bet if the firefighter knew that they'd surely still be nice on the outside but they'd probably have a negative story to tell their spouse when they got home.
I completely understand that not booking a motel facilitated human connection and all that loveliness but I sense that the benefit is very one-sided. In Zuckerberg-esque style, the tech bro gets to cosplay as a human with real emotions, while on the "normie NPC" side they get to deal with a tech bro on a bicycle asking for weird shit while they're just trying to get through a shift.