Gene's method (rolling on a flat surface and letting the reel pull the film) is the method I use, too. And as he mentions you need to cup the film slightly and let the reel do the work (i.e., don't roll it onto the reel but let the reel pull the film.)
I addition, I use the Hewes reels. These are very well made (will last a lifetime) and have two prongs on the spindle that allow you to anchor the film with the sprocket holes. I never rewind the film all the way into the film cassette when I'm done exposing a roll. Instead I leave the tongue hanging out (you can bend it slightly to signify an exposed roll.)
With the tongue out, I cut off the end squarely and attach the film sprockets to the Hewes reel in daylight. Once the film is anchored with the Hewes it will never skip a space on the reel. I roll it on completely in the dark, of course (a Harrison film tent works great.) Getting the film onto the reel correctly (Hewes or generic) is important and starting it in daylight makes it very easy.
The Hewes are made in the UK and are worth every penny, imho.
Here's the Hewes reel compared to a generic made in China reel. And you can see the prongs on the spindle in the other photo of the Hewes by itself.