Working for a bootstrapped startup as the CTO involves wearing a lot of hats. In this role over the years I've built servers, configured web hosting, configured databases, coded software, and designed user interfaces.
Often, this role also involve meeting with prospective clients, partners, and investors. Early in my career I worked for one such startup that was really struggling to pull in clients and the founder and CEO pulled me in on a really important sales meeting with a large prospective client to help show off our technical capabilities and make them feel comfortable.
During the conversation it became clear that our product wasn't going to meet their needs, but our CEO wasn't one to be deterred by this. Rather than be upfront about our capabilities or to offer to build what they needed, she went an entirely different direction and fabricated features out of thin air and described in great detail how our features (which didn't exist) would meet all of the prospective customers needs.
While listening to this I did my best to avoid wearing my inner feelings on my face, barely able to focus on what she was saying because I was so shocked at the blatant lie. While I was trying to figure out how to respond she cheerfully turned to me and said, "Why don't you tell them all about the technology behind these features?"
The only saving grace is the client didn't seem to know (or care) about the technology so they rushed me to a blissful silence. Needless to say, I didn't hold that position for too long after that.
