I think you'll eventually run into this scenario in most places. My advice would be create a case from possibly a "velocity" point of view. For example, I spend

I think you'll eventually run into this scenario in most places. My advice would be create a case from possibly a "velocity" point of view. For example, I spend x minutes dealing with this issue on a daily basis which slows me down. It can be solved with this etc. As a team we can move forward and benefit by this etc. Mostly with start ups, it's about delivering the results but not necessarily in the cleanest way. Many start ups accure technical debt which they eventually have to go back and visit. I think best way is to see your technical lead as someone who is meeting his goals that are being set by management and as long as he is meeting them there is no need to change. But if you can help him speed up his goals or help him achieve more then it will interest him.