How can I convince my (non designer) boss he is wrong?

I currently do design work for a company that sells items online to trades people and we are about to launch a new website under different branding that will be open to everyone to buy from.

My boss has picked the name he wants (it is a sort of pun or wordplay related to the industry we are in) and he is now looking a logo designed for it. I thought maybe I was going to get to come up with ideas on my own but yesterday he handed me a piece of paper with a quick sketch of what he wanted the logo to look like and straight away I knew it wasn't going to work. The sketch was a typographic based logo but with random letters replaced with a real life image of an item we will be selling that kind of looks like the shape of the letter it is replacing and a triangle tacked on to an extended stem of the last letter in the name to make it look like an arrow (sorry this is a bit vague, we haven't bought the domain yet so I don't want to reveal the actual name). I tried using every excuse I could think of to convince him not to go ahead with this design; "It's too busy and messy looking", "It won't be readable at small sizes", "Using real life images doesn't gel with the text". He kept coming back with small variations on his original concept. Everytime I came up with an excuse I could tell he was getting more annoyed even though I mocked it up on different things to illustrate my point. I done several of my own designs incorporating some of the elements he suggested but in more subtle ways and using a colour that you would associate with our industry without screaming "HEY GUYS LOOK AT OUR NAME, DOESN'T THAT INDICATE WHAT WE SELL? NO? WELL HERE'S AN IMAGE AND A SHAPE JUST INCASE YOU STILL NEED A LITTLE HELP WORKING IT OUT". Nope, I came in this morning and he basically said "You need to put the name inside this real life image, make the type black and put it on an orange background."

I just want to tell him that the design looks unprofessional and tacky and that if I seen it on a website I would probably not buy anything from said website as it doesn't look like a serious business, although going by the way he reacted previously, if I said that it would probably end in me being told to either do it or clear my desk. Is there anything, ANYTHING I can do to change his mind? I have done the design he asked, which might as well have been made in MS Paint, and I would honestly be embarrassed if my name was attached to it.

Great design resource

100 Things Every Designer Needs to Know About People (Voices That Matter) Submitted January 24, 2018 at 11:21AM by xombie_christ http://ift.tt/2DuRhi0