Toe hold:
You didn't have his hips stuck/stationary (you were allowing him to spin).
His leg was too straight
You started off well, with your right leg pinning his leg to the ground. Once you let him up and start to spin, he straightened his leg and things got difficult.
At :22 you had his hips pinned again, but you needed to bend at the waist to bend his leg. Again you let pressure off of his free leg and he rolled, pushed on your bum, and got out.
When you're trying to finish the toe hold, think of planting his big toe in his butthole. This illustrates the bent-ness of the leg, the right entry into the toe hold, and the importance of keeping him from spinning (you can't put his toe in his butt if you're facing his bellybutton, for instance).
The guy was able to keep his cool, props to him for that. If he had freaked, he might've tapped earlier on. But because of your mistakes (not trapping the free leg/keeping his hips stationary, not bending his leg) he was able to roll out.
I think you were letting pressure off of his leg to add more torque to the toe hold. Next time, instead, scoot your butt towards his free leg to get a better angle on the toe hold, while maintaining pressure on his free leg to keep him from spinning. Finally, the strength of a toe hold is multiplied exponentially the more the leg is bent. Try it with your training partners; have their leg straight, and then have it bent at 90, and then maximum bentedness. You'll see a big difference, I guarantee it.
Points to work on:
- Pressure on free leg
- Scooting hips to get more pressure on toe hold (rather than shifting your weight)
- Keeping the toe-held leg bent
People who go for leglocks sometimes are so fixated on the lock that they forget about the free leg. If I had to rate it in importance, the leg you're attacking is 51% important, and the free leg is 49% important, and this really shows when you get guys used to defending leg locks.