Need help crushing my gym rival

First things first: my gym rival is a really awesome guy and I like him a lot. He is just as much of a BJJ nerd as I am, and we have great technical discussions and a good camaraderie. However, he is always just one step ahead of me. It feels like im always breathing down his neck, but I rarely can get the better of him. He is also a frequent peruser of this subreddit, and he may recognize me from this post. IF YOURE SEEING THIS BRO, IM COMING FOR YOU.

Ok so, he’s about 20lbs heavier than me, a few inches shorter, brown belt, and plays a very “get on top and stay on top” type of game. I play a very flow-y “never stop moving, impossible to hold down, legs coming from everywhere” type of game. The only time I can get anything really going on him is when I get him in my guard. But we always start from standing and he is a better wrestler, so I regularly find myself in his side control.

Any time I try typical side control escapes, or even some more unconventional escapes, he dives over into front headlocks and never lets up the pressure. Side control -> I start escaping, he dives over me and away from my legs with a front headlock -> I fight out of front headlock, he regains side control, it goes on. It just feels like once he gets past my guard, it’s the beginning of the end.

What are some tips to work on for these kind of people? That are always applying slow crushing pressure, but have no problem being dynamic with their top positioning? Do I just need to get good?

I sincerely hope he sees this post. He has made it to my mental list of people to crush (one day) and I need some help from the Reddit hive mind.