If you think it doesn't matter, you're wrong.
What I don't see is a lot of founders who are bad at written communication. Maybe it's self-selection (those who can't write are less likely to try to write online, so I won't see them as frequently, if ever), but it really seems like being good at written English is a requirement for being a successful tech entrepreneur now. "Good at written English" doesn't necessarily mean perfectly idiomatic and grammatical American College English, but clear and persuasive when the reader is fluent in (American, College, Middle/Upper class, Standard) English.
The nice thing is written English is much easier for "tech people" to learn; the best training is reading lots of well-written English, and you need to do that to participate in the technology and startup world anyway. The keys are: 1) having good source material (there's a tipping point, like some sizable non-US English communities -- which is why Singlish is a thing) 2) actually caring.
Replace Drew's intentional lack of capitalization with this "your/you're swap," and you've got the same situation.
It seems like people are just prejudiced, and are so prejudiced that they feel justified in calling people out on a forum under the guise of "helping" them.
Yes, grammar is powerful, but this isn't a situation where it matters. They were expressing empathy. They weren't writing a press release. And we can't seem to find it in ourselves to avoid bikeshedding this thread.
"how is babby formed" type stuff is what is incomprehensible.
"How is babby formed" is still generally a bad question, marginally worse than "Where do babies come from?", in that it's unclear if the focus is impregnation or gestation, and "babby" could be potentially misinterpreted as "babble".
IMO OP was borderline "bad at written communication" too, at least if the goal was to convey factual details of the situation. It was entertaining, but unclear. Sometimes obscuring key details is the goal, but generally not in technical or business writing.
The point you're trying to make is based on the mistaken assumption that they were being unclear. They weren't. Nothing was obscured. No one seriously believed that they meant to imply ownership instead of "you are."
They also weren't doing technical or business writing. It was empathy, which is sometimes helpful.
At the very least, not making an effort to use the correct word is extremely disrespectful of your audience and their time.
When you're in a situation when your message is competing with others, the clearer wording will out-compete muddled wording. That could be in advertising, recruiting, pitching, evangelizing, or any number of places where you want to influence the reader in some way. Every Joule they waste puzzling out your words is one they won't use being influenced (positively) by your message.
How often do you see you're/your confused in professional advertising or press releases? Very rarely.
When learning a language, I love gentle corrections to the many inevitable faults, and wish people would do it more often, because it helps you improve. Perhaps that varies with the person, but please don't interpret them as insults or bikeshedding to reinforce someone's ego, as they very rarely are. Communication is also about authority, tone and style, so just being able to guess what someone meant is not always good enough.
This was just a small note to this person about a repeated mistake which is undermining their credibility. If they take note, their communication will be improved for the rest of their life by not confusing these two homophones.
Daniel Kahneman refers to this as "cognitive ease" vs. "cognitive strain". Making your writing correct and easy to read increases cognitive ease, which makes your readers "like what [they] see, believe what [they] hear, trust [their] intuitions and feel that the current situation is comfortably familiar." [2]
Grammar is important for making a good impression as well, but that's really not the key selling point, especially for anyone in business. The key point is that if you want to persuade anyone of anything, whether it's to invest in your startup, to buy your product, or to leave their cushy Google job to work for you, you will be more persuasive if you use proper grammar.
[1] "Effects of Perceptual Fluency on Affective Judgments" http://psy2.ucsd.edu/~pwinkiel/reber-winkielman-schwarz-Flue...
[2] Thinking Fast and Slow
Start-up life keep it coming. I've rode your high and lows and will continue to do so til the end!
your => you're * 2
rode => ridden
Again, why not get it right, since there's no doubt you can?
The same happened with the article: too well written to be enjoyable. You could feel the effort in finding clever ways to say simple things.
The fact that you didn't thank him for taking the time to help you, makes me think that for you self improvement is less important than looking smart. As he said, <I'm not knocking you down but trying to help you from making trivial mistakes that change people's perception and distract and detract from the important things> That explains it perfectly.
This:
> "it's the underlying thoughts however spelt that matter."
is not true. You didn't write your post in txtspk because that is not the locally acceptable way of communicating. It could be comprehensible, unambiguous and require less typing, but it just doesn't meet the tacitly agreed standards in this community and you would not expect your ideas to have the impact they deserve if you chose to write that way.
I doubt that "your" and "you're" are homophones in most other languages. As a native English speaker myself, I often slip up and write "your" when I mean "you're" because they both sound the same in my head and it's quicker to type "your".
I think that a non-native speaker would be less like to make this mistake, because it requires the writer to decide to contract the pronoun and the verb and then forget to use an apostrophe.
I think this is far more likely to happen if you're simply typing out a stream of consciousness than if you're translating your thoughts from a different language.
Another reason non-natives don't do this mistake might be that usually they are thought the written language first, so schools concentrate on grammatical issues more.
As the parent commenter said, I've also noticed in the past that this mix up occurs usually among native English speakers. I've noticed it with other languages too, that native speakers often mix up homophones, probably because as a native speaker you write as you would speak and either you don't care or don't even think about it.
I agree with the other comment that this thread is toxic. I didn't intend that. I guess I learned a lesson.
It may seem obvious, but I never before considered how the simple grammatical mistakes I frequently make disproportionately hinder the ability of non-native speakers to efficiently comprehend my posts.
Your comment has given me an extra incentive to carefully proofread my future HN comments before posting.
The functioning of ideology. http://en.wikipedia.org/wiki/Ideology
Silicon Valley has its own ideology, and HN is the center of it. Any statement of "...is awesome" is a good candidate for finding the foundations of this ideology. Any good ideology has to encompass a diversity of views to survive. In this case, we see the public prostration of the spat out soul who voluntarily subjects their weakness to the crowd in the name of self-development. Addressing whether this is a good or bad thing would be to enter into the terms of which this particular ideology functions.
Most ideologies typically benefit a certain class of people: clergy, politicians, a bureaucracy, academia, venture capital.
When you see "community X is awesome" posted within community X, it's mostly a recent convert looking back and realizing that wherever they just came from was a comparatively bad fit for their personality and views.
I hear it a lot, here, from hackers switching from /r/programming to HN. I hear it on LessWrong from people who came from, for example, the atheist community, or the skeptic community, and didn't realize it was possible to talk about those subjects without constant dick-waving and chest-beating regarding their respective out-groups.
Either way, it's almost the opposite reaction to what you're accusing it of being: it's not like joining a cult; it's more like leaving high-school and realizing you can make friends with people because they talk about things you like, and behave in ways that don't annoy you, instead of just putting up with them because they're constantly forced to be around you for six hours a day.
Drew Houston writes without capitalization. Would you say the same to him? Ideas are what matter, not apostrophes.
On your second point, I think there's a clear difference between consistent lack of capitalization that is obviously a stylistic quirk, and simply using a homophone because you don't know (or, I guess as it turns out, don't care) that you're doing so. This is a common mistake and not usually due to ESL/EAL.
But I won't do it again, as it evidently is not a net good in this medium. Sorry, folks.
Thank you for informing me. Now that I know this, I'll look more seriously at Dropbox alternatives. This degree of carelessness and disrespect for others is dangerous in the CEO of a company asking me to trust them with my data.