Hi Anushree, thanks for your questions 
The people part of company building is the hardest and most important part. Most other problems can be solved if you have the right people are on the bus (and the wrong people not on the bus, which is just as important though not a particularly fun topic).
I think if you have people who are excited about working together, and working on the product/problem you are trying to solve then failures don’t really matter too much in the big picture, there are good weeks and bad weeks in startup life but I think everyone understands that.
As CEO the most important thing is to hire and promote the right people and to set a clear vision. I’m still learning that
How do you educate customers when you are a category creator targeting SMBs? A lot of outbound may turn out to be costly, your unit economics may go for a toss. Inbound may not work at all, since you are a new category! What are some of the less costly education tactics?
Content is amazing, if you truly nail a piece of content then it can get you noticed, and get you leads. The news media are the masters at this, their articles, opinion pieces, etc. get thousands of shares, we should learn from them. Having an opinion makes people interested in what you have to say, that’s partly why the Basecamp guys are so interesting, they put out a constant stream of their opinions (sometimes even publishing books of them).