Practice. Conversational style of writing. Audience that is used to long posts with minimal editing (Dealbreaker had shorter articles but his posts grew in length, references added, and the audience grew into that style...old Dealbreaker was hilarious, I seem to remember Matt did the CFA Level 1...he was going to hit the strip club for lulz during the lunch break, didn't but went to a Mexican cafe and got drunk...Dealbreaker 2008-2012 was pure gold, nothing like it today).

I wouldn't try to replicate his style. Lots of people try, but it is like a virgin turning up to a BDSM orgy: you can't hang, don't try, find your own path.

EDIT: wow, that Dealbreaker story was over 10 years old...what have I done with my life.