No, it shouldn’t matter that your website has a typo.
It certainly shouldn’t matter that your latest newsletter uses an apostrophe incorrectly.
It shouldn’t matter, but it does matter!
A prospective client who doesn’t know you, starts making judgements on you based on the limited information in front of them. If they’re reading a piece of your marketing and spot a typo, it adds to the mental picture they are building of you and your business.
It’s heartbreaking to lose sales because of a typo or misplaced apostrophe. Thankfully, it’s totally avoidable with just a little extra attention to detail.