Their whole philosophy is that you don't need to scale or sell out for VC money, and everything they did (and didn't do), is consistent with that.
Hey is just another service, like Basecamp, for those that want to pay for it, to sustain a profitable business. Not some Gmail-level wanabee.
I also happen to agree with that philosophy, considering eyeballs/VC/exit-oriented companies that aim for world domination poison and detrimental to consumers, to society, and to software.
I'd also like to note that what you call "boutique" is what, for the most part of capitalism, and even in IT up to the late 90s, we used to call a regular business.
Suddenly running a business with 10M-100M of revenue and a hefty profit is somehow an insult, and it's "boutique" or "lifestyle"...
I don’t know why. But the purpose of the marketing campaign of Hey sent that message.
I’m a big fan of non VC backed or boutique like companies (I have built and sold some of them), and it’s dangerous to send the wrong message to the market. I think that is what happened with Hey.
Did it tho? I'm not so sure. It's a marketing campaign, they're supposed to hype a product.
But if they were really going for this, it wouldn't just be pushed to their regular customers and nerd public. They'd get big VC money involved, make it free, push it much harder with ads everywhere, etc.
Well, they built Basecamp and a few other products, which kept them going for close to 20 years with tons of paying customers (and even some Bezos investment), so there's that.
Not to mention creating RoR...