I have been getting into The Jamil Show on my way to work lately, and I heard him mention that he doesn't rack to secondary anymore, but not why. Is there a benefit to this?

It's not really necessary for most beer styles. The beer will not suffer being on the yeast cake for 2, 3, or 4 weeks. Transferring to secondary allows for more chance of infection plus the extra cleanup. I gave it up years ago.
Good luck and welcome to the Madhouse!

The risk of infection from transfer far outweighs the reward...if there even is any reward.

It makes some people warm and fuzzy, usually because that's how they've always done it. If you start throwing things in your beer (fruit, etc.), or leave it for over a month, then you might think about it, but in general it is a waste of time.

Secondary is for suckers!
Just kidding. I choose to "secondary" in kegs. Works for me. You can even dry hop in them suckers. Just use a surescreen or something similar.
If you are going to be using fruit, you may want to do a secondary. Infection shouldnt be a problem, if you are following sound sanitation practices.

Technically speaking, secondary refers to a second fermentation resulting from the addition of additional fermentables. An example would be racking a beer onto some fruit. Fermentation would take off again while the remaining yeast in suspension digests the sugars in the fruit.

What most folks refer to secondary is simply racking the beer to a bright tank to allow yeast and other junk to settle out in order to clarify the beer. Most of us who have given up "secondary" simply rack to a keg as a bright tank. Drawing off (and sometimes discarding) the first pint or so gets rid of all the settled junk that is going to get into your glass and then you can pour clear beer. For those who bottle, racking the beer to another carboy or bucket serves the same purpose of clearing the beer before bottling.

Wayne

If I'm bottling I'll rack to a secondary (usually my bottling bucket), otherwise it's just straight into the keg. I also leave my beer on the yeast cake for about 2 weeks just to let the yeast to clear up any unwanted compounds of fermentation.

Racking to a secondary isn't necessary but can help with some styles

And transferring to secondary is one other source of oxidation. I only secondary sour beers and fruit beers. And I'm lazy, so there's one less fermentor to clean.