Caleb Pressley On Interviewing Drake + Dream Guest For Sundae Conversation

Recorded: November 21st 2023 | On this weeks episode the boys recap their Thanksgiving weekends along with the football weekend that was. Taylor recaps his time at "The Game", Michigan vs Ohio State. He gets into how it's Michigan vs The World and that everyone on the bus wishes for his downfall. Will had to check him saying that's not the case and that Taylor is just an obnoxious fan. The boys get into what they did for Thanksgiving and tell some hilarious stories from the dinner involving Taylor's grandparents.

Following the intro, we are finally graced with the presence of one, Caleb Pressley. It has been a long time coming for Caleb to come on the bus but we were finally able to make it work his schedule. The guys sparked their friendship from when Caleb used to live in Nashville when they used to all workout together. Apparently Will and Taylor would do the working out but Caleb was there for the vibes. The guys then get into their time at the Notre Dame vs Ohio State game back in September as they share some hilarious stories from the trip.

Following that, Will brings up Caleb's show Sundae Conversation, which is one of the biggest brands for Barstool. Caleb tells some of the best stories of all the guests that he has had on, including what it was like interviewing Drake. He gets into some of his dream guests that he would like to have on in the future as well as his process in preparing for all of the different guests. This episode gives you a glimpse into the creative mind that is Caleb Pressley and how he goes about his business. He really is just another one of the guys who happens to be absolutely hilarious, you guys will definitely have laugh throughout the episode.

0:00 Intro
3:00 Thank you everyone for buying merch
6:13 Titans are in dissarray
15:28 "The Game" recap
21:28 Nebraska's season was a success
29:49 Taylor is all alone on the Michigan train
46:00 College Football Playoff possibilities
51:00 Shittiest Moment
1:01:10 Barstool Survivor
1:04:31 Caleb preview
1:09:40 Twisted Question
1:18:32 CALEB PRESSLEY INTERVIEW STARTS
1:18:37 Caleb is finally on
1:21:12 Will faked Caleb's death
1:26:02 The boys used to workout together
1:28:09 Notre Dame weekend
1:43:26 Sundae Conversation (Best guest, preparation, future guests)
1:53:15 Glenny Balls has the best life
1:55:30 How the business of Sundae Conversation happens
2:02:10 You have to see your friends as much as possible
2:20:12 Does Riggs suck?
2:21:41 His inspiration behind Sundae Convo

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