Andrew Smith is a 3rd-degree BJJ black belt based out of Richmond, VA (Revolution BJJ). He runs BJJ Path, a video tutorial website.
Side to Mount
Getting to the mount can be a daunting task against a savvy opponent. Although side control itself can be among the most dominant positions, sometimes moving to mount is called for, whether in a point-scoring situation or for general positional improvement. We'll go over four different methods to get to the mount position, and take a look at some situational tricks you can use to get the job done.
Classic Knee Drive
Starting on your partner's right side in "head and arm" side control, begin by using shoulder pressure to turn your partner's head to their left. This will allow you to lift your right knee up and across their stomach ("lift" doesn't really do the sneaky slide upward justice, but it's the best one word description for now). The general idea here is to drive your right knee to the ground, but your partner will be able to reach your knee and block using their left hand. Instead of allowing this to happen, flare your right arm out, or walk your right arm upward, ultimately moving their arm away from your knee. Staying as tight as possible, "windshield wiper" your right foot around your partner's hips, taking care not to allow them to snag your foot in half guard.
Once again starting on your partner's right side, start by switching your hips to reverse kesa gatame ("kimura position," if the Japanese terminology doesn't resonate). Throw your left arm over their face, thus obscuring their field of vision. Next up, push your partner's legs away from you, so they want to push back. When they do, "help them" by pulling their knees in closer so that you can then step over their legs with your right foot. It's important that you drag your far (left) knee in close during this process so there isn't extra space for a side control type escape back to guard while you are trying to attain mount.
"Sneaky Mount" is the companion piece to the "hip switch mount" we just covered. The basic mechanics start exactly the same, with a vision-obscuring hip-switch. Remember that once you have switched your hips, you should also strive to isolate the "inside arm" (their right arm). Don't forget to block your partner's far knee any time you're in reverse kesa too, or else you might be kneed in the face at some point during your roll. As a consequence, it is necessary to drop your head low (bury it) so that you can liberate your right hand, so that you can then grab your right foot to guide it across your partner's hips to the other side. Before doing this, be sure to switch your base to a perpendicular one (before stepping over), or else your partner may be able to bridge and roll during the transition (think of your right foot as a "kickstand" here).
Hip Twist Mount
This style of moving to the mount is a good solution when your partner is balling up in a "fetal position" ("fetal guard," or the "running man" position has a place in BJJ defense, no doubt, but it can be frustrating to deal with from the top person's perspective). Take advantage of the position by grabbing the back of their collar with your right hand, and by grabbing their far (left) leg with your right hand. "Kickstand" your left leg out, just like establishing a knee on stomach type position, and then pull their collar toward you. Finally, pull their legs toward you in order to twist their hips in the opposite direction of their shoulders, creating an awful position from the bottom person, and step over to mount.
Hopefully these four methods to get to the mount position will give you ample ideas of how to solve the problem of moving to mount from side control. There are bound to be other problems that these videos and lessons won't address, but you should have enough principle-based theory in order to solve your own problems. Just think about what really makes each of the moves work, and integrate these elements into your own solutions. As always, let me know how these techniques work for you! I'm happy to hear your stories.