i would use that money to maybe produce shows and perform as much as possible. reading books by Keith Johnstone or Del Close could give you some theory, but nothing will teach you like the stage and performing as much as you can! Watch great improv, it will help you do great improv. Maybe take the team to chicago for a few shows? That will be hugely helpful! Good luck
the poker scene in season 1 was very written but then i let the guys go off and fuck around. i used some of that. I don't generally let people improvise though. That works for shows where you have two cameras that are just sort of following the action. i shoot my show like a movie and it would be all fucked up if folks just said things.
I started to take improv classes with Washington Improv Theater at the exact same time I started going around to open mics in DC to watch and if lucky perform. Took about a month of watching before I really got to get on the microphone at any of the shows. So that month of foundations of improv learning with the great Dave Johnson really influenced my approach to standup. Not that I wanted to get up and improvise but the moments of not being funny on stage was easier to cope with after having learned to relax and build from nothing in class.
The first rule of improvisation is “agree” always agree and say “yes” … when you are improvising this means you are required to agree with whatever your partner has created … so if we’re improvising and I say “freeze I have a gun” and you say “that’s not a gun, it’s your finger” our improvised scene has ground to a halt … now in real life you are obviously not going to agree with everything everyone always says but the “rule of agreement” gets you to at least start from an open minded place … start with a “yes” and see where that takes you … as an improvisor I always find it jarring in real life when I meet someone who’s first answer is “no” …
The second rule of improvisation is to not only say “yes” but “yes and” … you’re supposed to agree and then add something of your own … “if I start a scene and say “it’s so hot in here” and you just say “yeah”, we’re kind of at a standstill … to me, “yes and” means don’t be afraid to contribute, it’s your responsibility to contribute … always make sure you are adding something to the discussion … your initiations are worthwhile …
The next rule is “make statements” which is a positive way of saying don’t ask questions all the time … if we’re in a scene and I say “who are you?” or “where are we?” or “what’s in that box?”, I am putting all of the pressure on you to come up with the answers … in other words, whatever the problem, be part of the solution … don’t just sit around raising questions and putting up obstacles.
When I first started taking improv classes (2003), I never used my own voice once in a scene. I really didn't feel comfortable doing that. I was a distinct character in every improv scene I did until I moved to NYC and started taking UCB classes (2008). So all of that character practice was great, but dropping them was also huge for me because it was easier for my performance style to translate to TV work.