This makes sense to me. I saw similar things in newspaper comments sections. I have a weird habit of always scrolling to comments sections of news articles. It gives me an interesting snapshot of a huge range of opinions. On political articles, I consistently saw so many comments from Trump supporters, with some consistent threads of opinions (as well as more fringe or extreme ideas) that just weren't being represented strongly enough in the general media. I also of course saw comments from Hillary supporters and Trump haters. Their arguments and thoughts WERE already being represented strongly in the general media - there was not much new that I learned there. Something that Obama hasn't addressed is just how biased our mainstream newspapers and magazines were in the run-up to the election. As someone living in a highly liberal area (and who is not aligned with Trump's politics - before I get criticized to infinity) I felt I gained a lot of understanding for why people were supporting Trump, not from the dozens of mainstream newspaper articles I read each day, but from comments sections. I view that as a media fail. I was the only person of my peer group who was not shocked about Trump's win. I'd also add - the media strategy didn't work. Marginalizing people's voices and points of view - often people who felt marginalized in other ways (economic etc), strengthened their resolve to vote for the person who DID hear them (which was Trump.)
A couple things stood out to me about Homejoy:
-When seeing the founder Adora speak at YC female founders day, she talked about doing cleaning herself to learn how things worked, and something along the lines of it being embarrassing if she'd been "seen" by someone she knew. That underlined to me there wasn't really a respect for cleaners. It seemed strange to start a business where you think it's embarrassing to be one of your own staff.
-When I did order Homejoy, the cleaner was sooo bad/slow that I felt that they'd secretly sent me one of their engineers who'd never cleaned an apartment before. He just seemed lost. He spent an hour and 45 minutes just cleaning my bathroom which was really strange. When he left, I realized that he'd moved the plunger out of the bathroom and left it on the bedroom floor and I had to move it back! It was just weird, an experienced cleaner wouldn't move a plunger into a clean area and just leave it there! I wrote a long email to them about the experience and they offered to send someone back to finish up the clean - of course I'd finished cleaning myself by then and said I wasn't interested. I didn't feel they really took my feedback to heart - it was detailed an took a while to write, but they didn't respond to any part of it directly.